WO2005033323A1 - 1,4−ジヒドロキシ−2−ナフトエ酸の製造法 - Google Patents
1,4−ジヒドロキシ−2−ナフトエ酸の製造法 Download PDFInfo
- Publication number
- WO2005033323A1 WO2005033323A1 PCT/JP2004/014394 JP2004014394W WO2005033323A1 WO 2005033323 A1 WO2005033323 A1 WO 2005033323A1 JP 2004014394 W JP2004014394 W JP 2004014394W WO 2005033323 A1 WO2005033323 A1 WO 2005033323A1
- Authority
- WO
- WIPO (PCT)
- Prior art keywords
- culture
- medium
- carbon source
- producing
- mass
- Prior art date
Links
- 238000000034 method Methods 0.000 title claims abstract description 33
- XBDQKXXYIPTUBI-UHFFFAOYSA-N dimethylselenoniopropionate Natural products CCC(O)=O XBDQKXXYIPTUBI-UHFFFAOYSA-N 0.000 claims abstract description 76
- 241000894006 Bacteria Species 0.000 claims abstract description 43
- 235000019260 propionic acid Nutrition 0.000 claims abstract description 38
- IUVKMZGDUIUOCP-BTNSXGMBSA-N quinbolone Chemical compound O([C@H]1CC[C@H]2[C@H]3[C@@H]([C@]4(C=CC(=O)C=C4CC3)C)CC[C@@]21C)C1=CCCC1 IUVKMZGDUIUOCP-BTNSXGMBSA-N 0.000 claims abstract description 38
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims abstract description 37
- 229910052799 carbon Inorganic materials 0.000 claims abstract description 35
- 238000012258 culturing Methods 0.000 claims abstract description 12
- VOJUXHHACRXLTD-UHFFFAOYSA-N 1,4-dihydroxy-2-naphthoic acid Chemical compound C1=CC=CC2=C(O)C(C(=O)O)=CC(O)=C21 VOJUXHHACRXLTD-UHFFFAOYSA-N 0.000 claims description 40
- 239000000203 mixture Substances 0.000 claims description 29
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims description 22
- 235000013305 food Nutrition 0.000 claims description 21
- 229910001873 dinitrogen Inorganic materials 0.000 claims description 18
- 238000004519 manufacturing process Methods 0.000 claims description 15
- 206010000059 abdominal discomfort Diseases 0.000 claims description 12
- 208000029725 Metabolic bone disease Diseases 0.000 claims description 11
- 208000030136 Marchiafava-Bignami Disease Diseases 0.000 claims description 10
- 239000003795 chemical substances by application Substances 0.000 claims description 10
- 238000003860 storage Methods 0.000 claims description 8
- 239000007789 gas Substances 0.000 claims description 7
- CURLTUGMZLYLDI-UHFFFAOYSA-N Carbon dioxide Chemical compound O=C=O CURLTUGMZLYLDI-UHFFFAOYSA-N 0.000 claims description 6
- 239000004480 active ingredient Substances 0.000 claims description 5
- 208000024891 symptom Diseases 0.000 claims description 5
- 239000003513 alkali Substances 0.000 claims description 4
- 239000003814 drug Substances 0.000 claims description 4
- 239000001569 carbon dioxide Substances 0.000 claims description 3
- 229910002092 carbon dioxide Inorganic materials 0.000 claims description 3
- 230000000069 prophylactic effect Effects 0.000 claims 1
- 229940124597 therapeutic agent Drugs 0.000 claims 1
- 239000001963 growth medium Substances 0.000 abstract description 8
- VOJUXHHACRXLTD-UHFFFAOYSA-M 1,4-dihydroxy-2-naphthoate Chemical compound C1=CC=C2C(O)=CC(C([O-])=O)=C(O)C2=C1 VOJUXHHACRXLTD-UHFFFAOYSA-M 0.000 description 59
- 108010065780 2-amino-4-hydroxy-6-hydroxymethyldihydropteridine pyrophosphokinase Proteins 0.000 description 58
- 108010089355 dihydroneopterin aldolase Proteins 0.000 description 58
- 239000002609 medium Substances 0.000 description 35
- GUBGYTABKSRVRQ-QKKXKWKRSA-N Lactose Natural products OC[C@H]1O[C@@H](O[C@H]2[C@H](O)[C@@H](O)C(O)O[C@@H]2CO)[C@H](O)[C@@H](O)[C@H]1O GUBGYTABKSRVRQ-QKKXKWKRSA-N 0.000 description 32
- 239000008101 lactose Substances 0.000 description 31
- 239000000843 powder Substances 0.000 description 18
- 238000005273 aeration Methods 0.000 description 17
- 108091005804 Peptidases Proteins 0.000 description 15
- 239000004365 Protease Substances 0.000 description 14
- 102100037486 Reverse transcriptase/ribonuclease H Human genes 0.000 description 14
- 235000020183 skimmed milk Nutrition 0.000 description 14
- 150000003839 salts Chemical class 0.000 description 13
- 239000000243 solution Substances 0.000 description 13
- 102000007544 Whey Proteins Human genes 0.000 description 11
- 108010046377 Whey Proteins Proteins 0.000 description 11
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 11
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 10
- 239000000796 flavoring agent Substances 0.000 description 10
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 9
- -1 dartene Substances 0.000 description 9
- 235000019634 flavors Nutrition 0.000 description 9
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 8
- 230000001954 sterilising effect Effects 0.000 description 8
- 238000004659 sterilization and disinfection Methods 0.000 description 8
- 235000013618 yogurt Nutrition 0.000 description 8
- CIWBSHSKHKDKBQ-JLAZNSOCSA-N Ascorbic acid Chemical compound OC[C@H](O)[C@H]1OC(=O)C(O)=C1O CIWBSHSKHKDKBQ-JLAZNSOCSA-N 0.000 description 7
- TYJJADVDDVDEDZ-UHFFFAOYSA-M potassium hydrogencarbonate Chemical compound [K+].OC([O-])=O TYJJADVDDVDEDZ-UHFFFAOYSA-M 0.000 description 7
- 230000017854 proteolysis Effects 0.000 description 7
- PEDCQBHIVMGVHV-UHFFFAOYSA-N Glycerine Chemical compound OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 description 6
- 239000005862 Whey Substances 0.000 description 6
- 235000019658 bitter taste Nutrition 0.000 description 6
- 229940041514 candida albicans extract Drugs 0.000 description 6
- 150000001720 carbohydrates Chemical class 0.000 description 6
- 238000000855 fermentation Methods 0.000 description 6
- 230000004151 fermentation Effects 0.000 description 6
- PPASLZSBLFJQEF-RKJRWTFHSA-M sodium ascorbate Substances [Na+].OC[C@@H](O)[C@H]1OC(=O)C(O)=C1[O-] PPASLZSBLFJQEF-RKJRWTFHSA-M 0.000 description 6
- 235000010378 sodium ascorbate Nutrition 0.000 description 6
- 229960005055 sodium ascorbate Drugs 0.000 description 6
- PPASLZSBLFJQEF-RXSVEWSESA-M sodium-L-ascorbate Chemical compound [Na+].OC[C@H](O)[C@H]1OC(=O)C(O)=C1[O-] PPASLZSBLFJQEF-RXSVEWSESA-M 0.000 description 6
- 238000003756 stirring Methods 0.000 description 6
- 239000012138 yeast extract Substances 0.000 description 6
- WQZGKKKJIJFFOK-GASJEMHNSA-N Glucose Natural products OC[C@H]1OC(O)[C@H](O)[C@@H](O)[C@@H]1O WQZGKKKJIJFFOK-GASJEMHNSA-N 0.000 description 5
- 241000186428 Propionibacterium freudenreichii Species 0.000 description 5
- 240000004808 Saccharomyces cerevisiae Species 0.000 description 5
- 235000014680 Saccharomyces cerevisiae Nutrition 0.000 description 5
- 239000007864 aqueous solution Substances 0.000 description 5
- 239000008103 glucose Substances 0.000 description 5
- 229910052500 inorganic mineral Inorganic materials 0.000 description 5
- 239000011707 mineral Substances 0.000 description 5
- 238000012360 testing method Methods 0.000 description 5
- 235000021119 whey protein Nutrition 0.000 description 5
- GUBGYTABKSRVRQ-XLOQQCSPSA-N Alpha-Lactose Chemical compound O[C@@H]1[C@@H](O)[C@@H](O)[C@@H](CO)O[C@H]1O[C@@H]1[C@@H](CO)O[C@H](O)[C@H](O)[C@H]1O GUBGYTABKSRVRQ-XLOQQCSPSA-N 0.000 description 4
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 4
- 229920002472 Starch Polymers 0.000 description 4
- 239000003463 adsorbent Substances 0.000 description 4
- WQZGKKKJIJFFOK-VFUOTHLCSA-N beta-D-glucose Chemical compound OC[C@H]1O[C@@H](O)[C@H](O)[C@@H](O)[C@@H]1O WQZGKKKJIJFFOK-VFUOTHLCSA-N 0.000 description 4
- 230000000052 comparative effect Effects 0.000 description 4
- 238000010438 heat treatment Methods 0.000 description 4
- JVTAAEKCZFNVCJ-UHFFFAOYSA-N lactic acid Chemical compound CC(O)C(O)=O JVTAAEKCZFNVCJ-UHFFFAOYSA-N 0.000 description 4
- 229910000027 potassium carbonate Inorganic materials 0.000 description 4
- 235000018102 proteins Nutrition 0.000 description 4
- 102000004169 proteins and genes Human genes 0.000 description 4
- 108090000623 proteins and genes Proteins 0.000 description 4
- 239000008107 starch Substances 0.000 description 4
- 235000019698 starch Nutrition 0.000 description 4
- 239000007858 starting material Substances 0.000 description 4
- 229940088594 vitamin Drugs 0.000 description 4
- 229930003231 vitamin Natural products 0.000 description 4
- 235000013343 vitamin Nutrition 0.000 description 4
- 239000011782 vitamin Substances 0.000 description 4
- 108010076119 Caseins Proteins 0.000 description 3
- 102000011632 Caseins Human genes 0.000 description 3
- CIWBSHSKHKDKBQ-DUZGATOHSA-N D-araboascorbic acid Natural products OC[C@@H](O)[C@H]1OC(=O)C(O)=C1O CIWBSHSKHKDKBQ-DUZGATOHSA-N 0.000 description 3
- DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 description 3
- 241001465754 Metazoa Species 0.000 description 3
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 3
- PVNIIMVLHYAWGP-UHFFFAOYSA-N Niacin Chemical compound OC(=O)C1=CC=CN=C1 PVNIIMVLHYAWGP-UHFFFAOYSA-N 0.000 description 3
- MUBZPKHOEPUJKR-UHFFFAOYSA-N Oxalic acid Chemical compound OC(=O)C(O)=O MUBZPKHOEPUJKR-UHFFFAOYSA-N 0.000 description 3
- KRKNYBCHXYNGOX-UHFFFAOYSA-N citric acid Chemical compound OC(=O)CC(O)(C(O)=O)CC(O)=O KRKNYBCHXYNGOX-UHFFFAOYSA-N 0.000 description 3
- 235000008504 concentrate Nutrition 0.000 description 3
- 239000012141 concentrate Substances 0.000 description 3
- 238000000354 decomposition reaction Methods 0.000 description 3
- 230000000694 effects Effects 0.000 description 3
- 235000010350 erythorbic acid Nutrition 0.000 description 3
- 239000004318 erythorbic acid Substances 0.000 description 3
- 238000011156 evaluation Methods 0.000 description 3
- 229940026239 isoascorbic acid Drugs 0.000 description 3
- 235000013336 milk Nutrition 0.000 description 3
- 239000008267 milk Substances 0.000 description 3
- 210000004080 milk Anatomy 0.000 description 3
- 239000003921 oil Substances 0.000 description 3
- 235000019198 oils Nutrition 0.000 description 3
- 150000007524 organic acids Chemical class 0.000 description 3
- 239000000047 product Substances 0.000 description 3
- 239000011734 sodium Substances 0.000 description 3
- 229910052708 sodium Inorganic materials 0.000 description 3
- 235000015112 vegetable and seed oil Nutrition 0.000 description 3
- 150000003722 vitamin derivatives Chemical class 0.000 description 3
- GHOKWGTUZJEAQD-ZETCQYMHSA-N (D)-(+)-Pantothenic acid Chemical compound OCC(C)(C)[C@@H](O)C(=O)NCCC(O)=O GHOKWGTUZJEAQD-ZETCQYMHSA-N 0.000 description 2
- BJEPYKJPYRNKOW-REOHCLBHSA-N (S)-malic acid Chemical compound OC(=O)[C@@H](O)CC(O)=O BJEPYKJPYRNKOW-REOHCLBHSA-N 0.000 description 2
- GVJHHUAWPYXKBD-UHFFFAOYSA-N (±)-α-Tocopherol Chemical compound OC1=C(C)C(C)=C2OC(CCCC(C)CCCC(C)CCCC(C)C)(C)CCC2=C1C GVJHHUAWPYXKBD-UHFFFAOYSA-N 0.000 description 2
- HZAXFHJVJLSVMW-UHFFFAOYSA-N 2-Aminoethan-1-ol Chemical compound NCCO HZAXFHJVJLSVMW-UHFFFAOYSA-N 0.000 description 2
- 241000186426 Acidipropionibacterium acidipropionici Species 0.000 description 2
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 2
- XKRFYHLGVUSROY-UHFFFAOYSA-N Argon Chemical compound [Ar] XKRFYHLGVUSROY-UHFFFAOYSA-N 0.000 description 2
- 102100026189 Beta-galactosidase Human genes 0.000 description 2
- OYPRJOBELJOOCE-UHFFFAOYSA-N Calcium Chemical compound [Ca] OYPRJOBELJOOCE-UHFFFAOYSA-N 0.000 description 2
- FEWJPZIEWOKRBE-JCYAYHJZSA-N Dextrotartaric acid Chemical compound OC(=O)[C@H](O)[C@@H](O)C(O)=O FEWJPZIEWOKRBE-JCYAYHJZSA-N 0.000 description 2
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 2
- 241000196324 Embryophyta Species 0.000 description 2
- VZCYOOQTPOCHFL-OWOJBTEDSA-N Fumaric acid Chemical compound OC(=O)\C=C\C(O)=O VZCYOOQTPOCHFL-OWOJBTEDSA-N 0.000 description 2
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 2
- XEEYBQQBJWHFJM-UHFFFAOYSA-N Iron Chemical compound [Fe] XEEYBQQBJWHFJM-UHFFFAOYSA-N 0.000 description 2
- 108010059881 Lactase Proteins 0.000 description 2
- FYYHWMGAXLPEAU-UHFFFAOYSA-N Magnesium Chemical compound [Mg] FYYHWMGAXLPEAU-UHFFFAOYSA-N 0.000 description 2
- AFVFQIVMOAPDHO-UHFFFAOYSA-N Methanesulfonic acid Chemical compound CS(O)(=O)=O AFVFQIVMOAPDHO-UHFFFAOYSA-N 0.000 description 2
- NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 description 2
- ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical compound [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 description 2
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 2
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 2
- FEWJPZIEWOKRBE-UHFFFAOYSA-N Tartaric acid Natural products [H+].[H+].[O-]C(=O)C(O)C(O)C([O-])=O FEWJPZIEWOKRBE-UHFFFAOYSA-N 0.000 description 2
- HCHKCACWOHOZIP-UHFFFAOYSA-N Zinc Chemical compound [Zn] HCHKCACWOHOZIP-UHFFFAOYSA-N 0.000 description 2
- 238000005377 adsorption chromatography Methods 0.000 description 2
- BJEPYKJPYRNKOW-UHFFFAOYSA-N alpha-hydroxysuccinic acid Natural products OC(=O)C(O)CC(O)=O BJEPYKJPYRNKOW-UHFFFAOYSA-N 0.000 description 2
- WPYMKLBDIGXBTP-UHFFFAOYSA-N benzoic acid Chemical compound OC(=O)C1=CC=CC=C1 WPYMKLBDIGXBTP-UHFFFAOYSA-N 0.000 description 2
- 108010005774 beta-Galactosidase Proteins 0.000 description 2
- 235000013361 beverage Nutrition 0.000 description 2
- 239000011575 calcium Substances 0.000 description 2
- 229910052791 calcium Inorganic materials 0.000 description 2
- 239000001913 cellulose Substances 0.000 description 2
- 229920002678 cellulose Polymers 0.000 description 2
- 230000029087 digestion Effects 0.000 description 2
- 150000002148 esters Chemical class 0.000 description 2
- 238000004401 flow injection analysis Methods 0.000 description 2
- OVBPIULPVIDEAO-LBPRGKRZSA-N folic acid Chemical compound C=1N=C2NC(N)=NC(=O)C2=NC=1CNC1=CC=C(C(=O)N[C@@H](CCC(O)=O)C(O)=O)C=C1 OVBPIULPVIDEAO-LBPRGKRZSA-N 0.000 description 2
- 239000008187 granular material Substances 0.000 description 2
- 229940093915 gynecological organic acid Drugs 0.000 description 2
- 229940116108 lactase Drugs 0.000 description 2
- 239000004310 lactic acid Substances 0.000 description 2
- 235000014655 lactic acid Nutrition 0.000 description 2
- 239000007788 liquid Substances 0.000 description 2
- 239000011777 magnesium Substances 0.000 description 2
- 229910052749 magnesium Inorganic materials 0.000 description 2
- 239000001630 malic acid Substances 0.000 description 2
- 235000011090 malic acid Nutrition 0.000 description 2
- 229940099690 malic acid Drugs 0.000 description 2
- 239000000463 material Substances 0.000 description 2
- 229910052751 metal Inorganic materials 0.000 description 2
- 239000002184 metal Substances 0.000 description 2
- BDAGIHXWWSANSR-UHFFFAOYSA-N methanoic acid Natural products OC=O BDAGIHXWWSANSR-UHFFFAOYSA-N 0.000 description 2
- 229960003512 nicotinic acid Drugs 0.000 description 2
- 235000001968 nicotinic acid Nutrition 0.000 description 2
- 239000011664 nicotinic acid Substances 0.000 description 2
- 229910052757 nitrogen Inorganic materials 0.000 description 2
- 235000005985 organic acids Nutrition 0.000 description 2
- 230000035699 permeability Effects 0.000 description 2
- 229910052700 potassium Inorganic materials 0.000 description 2
- 239000011591 potassium Substances 0.000 description 2
- 238000002360 preparation method Methods 0.000 description 2
- 230000002265 prevention Effects 0.000 description 2
- 229910000029 sodium carbonate Inorganic materials 0.000 description 2
- 239000007787 solid Substances 0.000 description 2
- 239000006228 supernatant Substances 0.000 description 2
- 235000020357 syrup Nutrition 0.000 description 2
- 239000006188 syrup Substances 0.000 description 2
- 239000003826 tablet Substances 0.000 description 2
- 239000011975 tartaric acid Substances 0.000 description 2
- 235000002906 tartaric acid Nutrition 0.000 description 2
- VZCYOOQTPOCHFL-UHFFFAOYSA-N trans-butenedioic acid Natural products OC(=O)C=CC(O)=O VZCYOOQTPOCHFL-UHFFFAOYSA-N 0.000 description 2
- 239000008158 vegetable oil Substances 0.000 description 2
- 238000009423 ventilation Methods 0.000 description 2
- 239000011701 zinc Substances 0.000 description 2
- 229910052725 zinc Inorganic materials 0.000 description 2
- OWEGMIWEEQEYGQ-UHFFFAOYSA-N 100676-05-9 Natural products OC1C(O)C(O)C(CO)OC1OCC1C(O)C(O)C(O)C(OC2C(OC(O)C(O)C2O)CO)O1 OWEGMIWEEQEYGQ-UHFFFAOYSA-N 0.000 description 1
- BMYNFMYTOJXKLE-UHFFFAOYSA-N 3-azaniumyl-2-hydroxypropanoate Chemical compound NCC(O)C(O)=O BMYNFMYTOJXKLE-UHFFFAOYSA-N 0.000 description 1
- OSWFIVFLDKOXQC-UHFFFAOYSA-N 4-(3-methoxyphenyl)aniline Chemical compound COC1=CC=CC(C=2C=CC(N)=CC=2)=C1 OSWFIVFLDKOXQC-UHFFFAOYSA-N 0.000 description 1
- ZCYVEMRRCGMTRW-UHFFFAOYSA-N 7553-56-2 Chemical compound [I] ZCYVEMRRCGMTRW-UHFFFAOYSA-N 0.000 description 1
- 241000186425 Acidipropionibacterium jensenii Species 0.000 description 1
- 241000186335 Acidipropionibacterium thoenii Species 0.000 description 1
- 229920001817 Agar Polymers 0.000 description 1
- 239000005711 Benzoic acid Substances 0.000 description 1
- 208000020084 Bone disease Diseases 0.000 description 1
- GHOKWGTUZJEAQD-UHFFFAOYSA-N Chick antidermatitis factor Natural products OCC(C)(C)C(O)C(=O)NCCC(O)=O GHOKWGTUZJEAQD-UHFFFAOYSA-N 0.000 description 1
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 1
- KRKNYBCHXYNGOX-UHFFFAOYSA-K Citrate Chemical compound [O-]C(=O)CC(O)(CC([O-])=O)C([O-])=O KRKNYBCHXYNGOX-UHFFFAOYSA-K 0.000 description 1
- RYGMFSIKBFXOCR-UHFFFAOYSA-N Copper Chemical compound [Cu] RYGMFSIKBFXOCR-UHFFFAOYSA-N 0.000 description 1
- 241000186427 Cutibacterium acnes Species 0.000 description 1
- 241001464974 Cutibacterium avidum Species 0.000 description 1
- ZZZCUOFIHGPKAK-UHFFFAOYSA-N D-erythro-ascorbic acid Natural products OCC1OC(=O)C(O)=C1O ZZZCUOFIHGPKAK-UHFFFAOYSA-N 0.000 description 1
- 239000004375 Dextrin Substances 0.000 description 1
- 229920001353 Dextrin Polymers 0.000 description 1
- 102000002322 Egg Proteins Human genes 0.000 description 1
- 108010000912 Egg Proteins Proteins 0.000 description 1
- PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 description 1
- 229930091371 Fructose Natural products 0.000 description 1
- 239000005715 Fructose Substances 0.000 description 1
- RFSUNEUAIZKAJO-ARQDHWQXSA-N Fructose Chemical compound OC[C@H]1O[C@](O)(CO)[C@@H](O)[C@@H]1O RFSUNEUAIZKAJO-ARQDHWQXSA-N 0.000 description 1
- 230000005526 G1 to G0 transition Effects 0.000 description 1
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 1
- 102000004407 Lactalbumin Human genes 0.000 description 1
- 108090000942 Lactalbumin Proteins 0.000 description 1
- JVTAAEKCZFNVCJ-UHFFFAOYSA-M Lactate Chemical compound CC(O)C([O-])=O JVTAAEKCZFNVCJ-UHFFFAOYSA-M 0.000 description 1
- 201000010538 Lactose Intolerance Diseases 0.000 description 1
- WHXSMMKQMYFTQS-UHFFFAOYSA-N Lithium Chemical compound [Li] WHXSMMKQMYFTQS-UHFFFAOYSA-N 0.000 description 1
- GUBGYTABKSRVRQ-PICCSMPSSA-N Maltose Natural products O[C@@H]1[C@@H](O)[C@H](O)[C@@H](CO)O[C@@H]1O[C@@H]1[C@@H](CO)OC(O)[C@H](O)[C@H]1O GUBGYTABKSRVRQ-PICCSMPSSA-N 0.000 description 1
- 108010070551 Meat Proteins Proteins 0.000 description 1
- 239000004368 Modified starch Substances 0.000 description 1
- 229920000881 Modified starch Polymers 0.000 description 1
- OVBPIULPVIDEAO-UHFFFAOYSA-N N-Pteroyl-L-glutaminsaeure Natural products C=1N=C2NC(N)=NC(=O)C2=NC=1CNC1=CC=C(C(=O)NC(CCC(O)=O)C(O)=O)C=C1 OVBPIULPVIDEAO-UHFFFAOYSA-N 0.000 description 1
- 241000237502 Ostreidae Species 0.000 description 1
- 235000019482 Palm oil Nutrition 0.000 description 1
- 102000035195 Peptidases Human genes 0.000 description 1
- 239000001888 Peptone Substances 0.000 description 1
- 108010080698 Peptones Proteins 0.000 description 1
- 108010064851 Plant Proteins Proteins 0.000 description 1
- OFOBLEOULBTSOW-UHFFFAOYSA-N Propanedioic acid Natural products OC(=O)CC(O)=O OFOBLEOULBTSOW-UHFFFAOYSA-N 0.000 description 1
- 241001464976 Propionimicrobium lymphophilum Species 0.000 description 1
- 108010009736 Protein Hydrolysates Proteins 0.000 description 1
- 235000019485 Safflower oil Nutrition 0.000 description 1
- BUGBHKTXTAQXES-UHFFFAOYSA-N Selenium Chemical compound [Se] BUGBHKTXTAQXES-UHFFFAOYSA-N 0.000 description 1
- XUIMIQQOPSSXEZ-UHFFFAOYSA-N Silicon Chemical compound [Si] XUIMIQQOPSSXEZ-UHFFFAOYSA-N 0.000 description 1
- 108010073771 Soybean Proteins Proteins 0.000 description 1
- KDYFGRWQOYBRFD-UHFFFAOYSA-N Succinic acid Natural products OC(=O)CCC(O)=O KDYFGRWQOYBRFD-UHFFFAOYSA-N 0.000 description 1
- 229930006000 Sucrose Natural products 0.000 description 1
- CZMRCDWAGMRECN-UGDNZRGBSA-N Sucrose Chemical compound O[C@H]1[C@H](O)[C@@H](CO)O[C@@]1(CO)O[C@@H]1[C@H](O)[C@@H](O)[C@H](O)[C@@H](CO)O1 CZMRCDWAGMRECN-UGDNZRGBSA-N 0.000 description 1
- 229930003268 Vitamin C Natural products 0.000 description 1
- 229930003316 Vitamin D Natural products 0.000 description 1
- QYSXJUFSXHHAJI-XFEUOLMDSA-N Vitamin D3 Natural products C1(/[C@@H]2CC[C@@H]([C@]2(CCC1)C)[C@H](C)CCCC(C)C)=C/C=C1\C[C@@H](O)CCC1=C QYSXJUFSXHHAJI-XFEUOLMDSA-N 0.000 description 1
- 229930003427 Vitamin E Natural products 0.000 description 1
- 229930003448 Vitamin K Natural products 0.000 description 1
- 229920002494 Zein Polymers 0.000 description 1
- 244000273928 Zingiber officinale Species 0.000 description 1
- 235000006886 Zingiber officinale Nutrition 0.000 description 1
- 239000002253 acid Substances 0.000 description 1
- 230000002378 acidificating effect Effects 0.000 description 1
- 150000007513 acids Chemical class 0.000 description 1
- 206010000496 acne Diseases 0.000 description 1
- 239000008272 agar Substances 0.000 description 1
- 229910052783 alkali metal Inorganic materials 0.000 description 1
- 229910000147 aluminium phosphate Inorganic materials 0.000 description 1
- 229910021529 ammonia Inorganic materials 0.000 description 1
- 239000010775 animal oil Substances 0.000 description 1
- 235000021120 animal protein Nutrition 0.000 description 1
- 229910052786 argon Inorganic materials 0.000 description 1
- 235000010323 ascorbic acid Nutrition 0.000 description 1
- 239000011668 ascorbic acid Substances 0.000 description 1
- 229960005070 ascorbic acid Drugs 0.000 description 1
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 1
- 239000002585 base Substances 0.000 description 1
- 235000013527 bean curd Nutrition 0.000 description 1
- SRSXLGNVWSONIS-UHFFFAOYSA-N benzenesulfonic acid Chemical compound OS(=O)(=O)C1=CC=CC=C1 SRSXLGNVWSONIS-UHFFFAOYSA-N 0.000 description 1
- 229940092714 benzenesulfonic acid Drugs 0.000 description 1
- 235000010233 benzoic acid Nutrition 0.000 description 1
- 229960004365 benzoic acid Drugs 0.000 description 1
- SQVRNKJHWKZAKO-UHFFFAOYSA-N beta-N-Acetyl-D-neuraminic acid Natural products CC(=O)NC1C(O)CC(O)(C(O)=O)OC1C(O)C(O)CO SQVRNKJHWKZAKO-UHFFFAOYSA-N 0.000 description 1
- GUBGYTABKSRVRQ-QUYVBRFLSA-N beta-maltose Chemical compound OC[C@H]1O[C@H](O[C@H]2[C@H](O)[C@@H](O)[C@H](O)O[C@@H]2CO)[C@H](O)[C@@H](O)[C@@H]1O GUBGYTABKSRVRQ-QUYVBRFLSA-N 0.000 description 1
- 239000011230 binding agent Substances 0.000 description 1
- 235000015895 biscuits Nutrition 0.000 description 1
- 235000008429 bread Nutrition 0.000 description 1
- KDYFGRWQOYBRFD-NUQCWPJISA-N butanedioic acid Chemical compound O[14C](=O)CC[14C](O)=O KDYFGRWQOYBRFD-NUQCWPJISA-N 0.000 description 1
- 235000014121 butter Nutrition 0.000 description 1
- 239000002775 capsule Substances 0.000 description 1
- 235000014633 carbohydrates Nutrition 0.000 description 1
- 239000005018 casein Substances 0.000 description 1
- BECPQYXYKAMYBN-UHFFFAOYSA-N casein, tech. Chemical compound NCCCCC(C(O)=O)N=C(O)C(CC(O)=O)N=C(O)C(CCC(O)=N)N=C(O)C(CC(C)C)N=C(O)C(CCC(O)=O)N=C(O)C(CC(O)=O)N=C(O)C(CCC(O)=O)N=C(O)C(C(C)O)N=C(O)C(CCC(O)=N)N=C(O)C(CCC(O)=N)N=C(O)C(CCC(O)=N)N=C(O)C(CCC(O)=O)N=C(O)C(CCC(O)=O)N=C(O)C(COP(O)(O)=O)N=C(O)C(CCC(O)=N)N=C(O)C(N)CC1=CC=CC=C1 BECPQYXYKAMYBN-UHFFFAOYSA-N 0.000 description 1
- 235000021240 caseins Nutrition 0.000 description 1
- 238000005119 centrifugation Methods 0.000 description 1
- 235000013351 cheese Nutrition 0.000 description 1
- 238000006243 chemical reaction Methods 0.000 description 1
- 210000000991 chicken egg Anatomy 0.000 description 1
- 239000000460 chlorine Substances 0.000 description 1
- 229910052801 chlorine Inorganic materials 0.000 description 1
- 229960001231 choline Drugs 0.000 description 1
- OEYIOHPDSNJKLS-UHFFFAOYSA-N choline Chemical compound C[N+](C)(C)CCO OEYIOHPDSNJKLS-UHFFFAOYSA-N 0.000 description 1
- 235000015165 citric acid Nutrition 0.000 description 1
- 239000011248 coating agent Substances 0.000 description 1
- 239000003240 coconut oil Substances 0.000 description 1
- 235000019864 coconut oil Nutrition 0.000 description 1
- ACTIUHUUMQJHFO-UPTCCGCDSA-N coenzyme Q10 Chemical compound COC1=C(OC)C(=O)C(C\C=C(/C)CC\C=C(/C)CC\C=C(/C)CC\C=C(/C)CC\C=C(/C)CC\C=C(/C)CC\C=C(/C)CC\C=C(/C)CC\C=C(/C)CCC=C(C)C)=C(C)C1=O ACTIUHUUMQJHFO-UPTCCGCDSA-N 0.000 description 1
- 238000007796 conventional method Methods 0.000 description 1
- 239000010949 copper Substances 0.000 description 1
- 229910052802 copper Inorganic materials 0.000 description 1
- 235000005687 corn oil Nutrition 0.000 description 1
- 239000002285 corn oil Substances 0.000 description 1
- 235000012495 crackers Nutrition 0.000 description 1
- 239000006071 cream Substances 0.000 description 1
- 238000012136 culture method Methods 0.000 description 1
- 235000015140 cultured milk Nutrition 0.000 description 1
- 230000003247 decreasing effect Effects 0.000 description 1
- 238000001514 detection method Methods 0.000 description 1
- 235000019425 dextrin Nutrition 0.000 description 1
- 235000014113 dietary fatty acids Nutrition 0.000 description 1
- 235000013325 dietary fiber Nutrition 0.000 description 1
- 150000002016 disaccharides Chemical class 0.000 description 1
- 239000007884 disintegrant Substances 0.000 description 1
- 239000000284 extract Substances 0.000 description 1
- 239000003925 fat Substances 0.000 description 1
- 239000000194 fatty acid Substances 0.000 description 1
- 229930195729 fatty acid Natural products 0.000 description 1
- 239000012467 final product Substances 0.000 description 1
- 235000021323 fish oil Nutrition 0.000 description 1
- 239000011737 fluorine Substances 0.000 description 1
- 229910052731 fluorine Inorganic materials 0.000 description 1
- 229960000304 folic acid Drugs 0.000 description 1
- 235000019152 folic acid Nutrition 0.000 description 1
- 239000011724 folic acid Substances 0.000 description 1
- 235000013355 food flavoring agent Nutrition 0.000 description 1
- 235000019253 formic acid Nutrition 0.000 description 1
- 235000015203 fruit juice Nutrition 0.000 description 1
- 239000001530 fumaric acid Substances 0.000 description 1
- 235000011087 fumaric acid Nutrition 0.000 description 1
- 235000013376 functional food Nutrition 0.000 description 1
- WIGCFUFOHFEKBI-UHFFFAOYSA-N gamma-tocopherol Natural products CC(C)CCCC(C)CCCC(C)CCCC1CCC2C(C)C(O)C(C)C(C)C2O1 WIGCFUFOHFEKBI-UHFFFAOYSA-N 0.000 description 1
- 239000000499 gel Substances 0.000 description 1
- 235000008397 ginger Nutrition 0.000 description 1
- 125000002791 glucosyl group Chemical group C1([C@H](O)[C@@H](O)[C@H](O)[C@H](O1)CO)* 0.000 description 1
- 239000001307 helium Substances 0.000 description 1
- 229910052734 helium Inorganic materials 0.000 description 1
- SWQJXJOGLNCZEY-UHFFFAOYSA-N helium atom Chemical compound [He] SWQJXJOGLNCZEY-UHFFFAOYSA-N 0.000 description 1
- 238000004128 high performance liquid chromatography Methods 0.000 description 1
- 230000002779 inactivation Effects 0.000 description 1
- 239000012770 industrial material Substances 0.000 description 1
- 239000011261 inert gas Substances 0.000 description 1
- 239000004615 ingredient Substances 0.000 description 1
- 230000000968 intestinal effect Effects 0.000 description 1
- 239000011630 iodine Substances 0.000 description 1
- 229910052740 iodine Inorganic materials 0.000 description 1
- 229910052742 iron Inorganic materials 0.000 description 1
- 235000015110 jellies Nutrition 0.000 description 1
- 239000008274 jelly Substances 0.000 description 1
- 150000002632 lipids Chemical class 0.000 description 1
- 238000004811 liquid chromatography Methods 0.000 description 1
- 229910052744 lithium Inorganic materials 0.000 description 1
- 239000000314 lubricant Substances 0.000 description 1
- VZCYOOQTPOCHFL-UPHRSURJSA-N maleic acid Chemical compound OC(=O)\C=C/C(O)=O VZCYOOQTPOCHFL-UPHRSURJSA-N 0.000 description 1
- 239000011976 maleic acid Substances 0.000 description 1
- WPBNNNQJVZRUHP-UHFFFAOYSA-L manganese(2+);methyl n-[[2-(methoxycarbonylcarbamothioylamino)phenyl]carbamothioyl]carbamate;n-[2-(sulfidocarbothioylamino)ethyl]carbamodithioate Chemical compound [Mn+2].[S-]C(=S)NCCNC([S-])=S.COC(=O)NC(=S)NC1=CC=CC=C1NC(=S)NC(=O)OC WPBNNNQJVZRUHP-UHFFFAOYSA-L 0.000 description 1
- 230000002503 metabolic effect Effects 0.000 description 1
- 229940098779 methanesulfonic acid Drugs 0.000 description 1
- 150000007522 mineralic acids Chemical class 0.000 description 1
- 235000019426 modified starch Nutrition 0.000 description 1
- 230000007935 neutral effect Effects 0.000 description 1
- 230000003472 neutralizing effect Effects 0.000 description 1
- 229920001542 oligosaccharide Polymers 0.000 description 1
- 150000002482 oligosaccharides Chemical class 0.000 description 1
- 235000006408 oxalic acid Nutrition 0.000 description 1
- 229940116315 oxalic acid Drugs 0.000 description 1
- 239000001254 oxidized starch Substances 0.000 description 1
- 235000013808 oxidized starch Nutrition 0.000 description 1
- 239000001301 oxygen Substances 0.000 description 1
- 229910052760 oxygen Inorganic materials 0.000 description 1
- 235000020636 oyster Nutrition 0.000 description 1
- 239000002540 palm oil Substances 0.000 description 1
- 229940055726 pantothenic acid Drugs 0.000 description 1
- 235000019161 pantothenic acid Nutrition 0.000 description 1
- 239000011713 pantothenic acid Substances 0.000 description 1
- 235000019319 peptone Nutrition 0.000 description 1
- 239000008194 pharmaceutical composition Substances 0.000 description 1
- 239000000546 pharmaceutical excipient Substances 0.000 description 1
- 150000003904 phospholipids Chemical class 0.000 description 1
- SHUZOJHMOBOZST-UHFFFAOYSA-N phylloquinone Natural products CC(C)CCCCC(C)CCC(C)CCCC(=CCC1=C(C)C(=O)c2ccccc2C1=O)C SHUZOJHMOBOZST-UHFFFAOYSA-N 0.000 description 1
- 239000000049 pigment Substances 0.000 description 1
- 235000013550 pizza Nutrition 0.000 description 1
- 235000021118 plant-derived protein Nutrition 0.000 description 1
- 229940024999 proteolytic enzymes for treatment of wounds and ulcers Drugs 0.000 description 1
- 238000000746 purification Methods 0.000 description 1
- 238000011002 quantification Methods 0.000 description 1
- IKGXIBQEEMLURG-NVPNHPEKSA-N rutin Chemical compound O[C@@H]1[C@H](O)[C@@H](O)[C@H](C)O[C@H]1OC[C@@H]1[C@@H](O)[C@H](O)[C@@H](O)[C@H](OC=2C(C3=C(O)C=C(O)C=C3OC=2C=2C=C(O)C(O)=CC=2)=O)O1 IKGXIBQEEMLURG-NVPNHPEKSA-N 0.000 description 1
- 235000005713 safflower oil Nutrition 0.000 description 1
- 239000003813 safflower oil Substances 0.000 description 1
- 229910052711 selenium Inorganic materials 0.000 description 1
- 239000011669 selenium Substances 0.000 description 1
- 230000001953 sensory effect Effects 0.000 description 1
- SQVRNKJHWKZAKO-OQPLDHBCSA-N sialic acid Chemical compound CC(=O)N[C@@H]1[C@@H](O)C[C@@](O)(C(O)=O)OC1[C@H](O)[C@H](O)CO SQVRNKJHWKZAKO-OQPLDHBCSA-N 0.000 description 1
- 239000010703 silicon Substances 0.000 description 1
- 229910052710 silicon Inorganic materials 0.000 description 1
- 239000011780 sodium chloride Substances 0.000 description 1
- 239000001488 sodium phosphate Substances 0.000 description 1
- 229910000162 sodium phosphate Inorganic materials 0.000 description 1
- 235000014214 soft drink Nutrition 0.000 description 1
- 239000002904 solvent Substances 0.000 description 1
- 235000019614 sour taste Nutrition 0.000 description 1
- 229940001941 soy protein Drugs 0.000 description 1
- 239000003381 stabilizer Substances 0.000 description 1
- 239000005720 sucrose Substances 0.000 description 1
- 150000005846 sugar alcohols Chemical class 0.000 description 1
- 239000000375 suspending agent Substances 0.000 description 1
- 238000003786 synthesis reaction Methods 0.000 description 1
- 238000010189 synthetic method Methods 0.000 description 1
- 235000019640 taste Nutrition 0.000 description 1
- 230000036962 time dependent Effects 0.000 description 1
- RYFMWSXOAZQYPI-UHFFFAOYSA-K trisodium phosphate Chemical compound [Na+].[Na+].[Na+].[O-]P([O-])([O-])=O RYFMWSXOAZQYPI-UHFFFAOYSA-K 0.000 description 1
- 108010050327 trypticase-soy broth Proteins 0.000 description 1
- 229960004747 ubidecarenone Drugs 0.000 description 1
- 235000019871 vegetable fat Nutrition 0.000 description 1
- 235000019154 vitamin C Nutrition 0.000 description 1
- 239000011718 vitamin C Substances 0.000 description 1
- 239000011710 vitamin D Substances 0.000 description 1
- 235000019166 vitamin D Nutrition 0.000 description 1
- 150000003710 vitamin D derivatives Chemical class 0.000 description 1
- 235000019165 vitamin E Nutrition 0.000 description 1
- 239000011709 vitamin E Substances 0.000 description 1
- 229940046009 vitamin E Drugs 0.000 description 1
- 235000019168 vitamin K Nutrition 0.000 description 1
- 239000011712 vitamin K Substances 0.000 description 1
- 150000003721 vitamin K derivatives Chemical group 0.000 description 1
- 229940046008 vitamin d Drugs 0.000 description 1
- 229940046010 vitamin k Drugs 0.000 description 1
- 235000008939 whole milk Nutrition 0.000 description 1
- 239000005019 zein Substances 0.000 description 1
- 229940093612 zein Drugs 0.000 description 1
- 235000021249 α-casein Nutrition 0.000 description 1
- 235000021247 β-casein Nutrition 0.000 description 1
Classifications
-
- A—HUMAN NECESSITIES
- A23—FOODS OR FOODSTUFFS; TREATMENT THEREOF, NOT COVERED BY OTHER CLASSES
- A23C—DAIRY PRODUCTS, e.g. MILK, BUTTER OR CHEESE; MILK OR CHEESE SUBSTITUTES; MAKING THEREOF
- A23C9/00—Milk preparations; Milk powder or milk powder preparations
- A23C9/12—Fermented milk preparations; Treatment using microorganisms or enzymes
- A23C9/1203—Addition of, or treatment with, enzymes or microorganisms other than lactobacteriaceae
-
- A—HUMAN NECESSITIES
- A23—FOODS OR FOODSTUFFS; TREATMENT THEREOF, NOT COVERED BY OTHER CLASSES
- A23L—FOODS, FOODSTUFFS, OR NON-ALCOHOLIC BEVERAGES, NOT COVERED BY SUBCLASSES A21D OR A23B-A23J; THEIR PREPARATION OR TREATMENT, e.g. COOKING, MODIFICATION OF NUTRITIVE QUALITIES, PHYSICAL TREATMENT; PRESERVATION OF FOODS OR FOODSTUFFS, IN GENERAL
- A23L2/00—Non-alcoholic beverages; Dry compositions or concentrates therefor; Their preparation
- A23L2/52—Adding ingredients
-
- A—HUMAN NECESSITIES
- A23—FOODS OR FOODSTUFFS; TREATMENT THEREOF, NOT COVERED BY OTHER CLASSES
- A23C—DAIRY PRODUCTS, e.g. MILK, BUTTER OR CHEESE; MILK OR CHEESE SUBSTITUTES; MAKING THEREOF
- A23C9/00—Milk preparations; Milk powder or milk powder preparations
- A23C9/12—Fermented milk preparations; Treatment using microorganisms or enzymes
-
- A—HUMAN NECESSITIES
- A23—FOODS OR FOODSTUFFS; TREATMENT THEREOF, NOT COVERED BY OTHER CLASSES
- A23C—DAIRY PRODUCTS, e.g. MILK, BUTTER OR CHEESE; MILK OR CHEESE SUBSTITUTES; MAKING THEREOF
- A23C9/00—Milk preparations; Milk powder or milk powder preparations
- A23C9/12—Fermented milk preparations; Treatment using microorganisms or enzymes
- A23C9/1203—Addition of, or treatment with, enzymes or microorganisms other than lactobacteriaceae
- A23C9/1209—Proteolytic or milk coagulating enzymes, e.g. trypsine
-
- A—HUMAN NECESSITIES
- A23—FOODS OR FOODSTUFFS; TREATMENT THEREOF, NOT COVERED BY OTHER CLASSES
- A23C—DAIRY PRODUCTS, e.g. MILK, BUTTER OR CHEESE; MILK OR CHEESE SUBSTITUTES; MAKING THEREOF
- A23C9/00—Milk preparations; Milk powder or milk powder preparations
- A23C9/20—Dietetic milk products not covered by groups A23C9/12 - A23C9/18
-
- A—HUMAN NECESSITIES
- A23—FOODS OR FOODSTUFFS; TREATMENT THEREOF, NOT COVERED BY OTHER CLASSES
- A23L—FOODS, FOODSTUFFS, OR NON-ALCOHOLIC BEVERAGES, NOT COVERED BY SUBCLASSES A21D OR A23B-A23J; THEIR PREPARATION OR TREATMENT, e.g. COOKING, MODIFICATION OF NUTRITIVE QUALITIES, PHYSICAL TREATMENT; PRESERVATION OF FOODS OR FOODSTUFFS, IN GENERAL
- A23L33/00—Modifying nutritive qualities of foods; Dietetic products; Preparation or treatment thereof
- A23L33/10—Modifying nutritive qualities of foods; Dietetic products; Preparation or treatment thereof using additives
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K31/00—Medicinal preparations containing organic active ingredients
- A61K31/185—Acids; Anhydrides, halides or salts thereof, e.g. sulfur acids, imidic, hydrazonic or hydroximic acids
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K31/00—Medicinal preparations containing organic active ingredients
- A61K31/185—Acids; Anhydrides, halides or salts thereof, e.g. sulfur acids, imidic, hydrazonic or hydroximic acids
- A61K31/19—Carboxylic acids, e.g. valproic acid
- A61K31/192—Carboxylic acids, e.g. valproic acid having aromatic groups, e.g. sulindac, 2-aryl-propionic acids, ethacrynic acid
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P1/00—Drugs for disorders of the alimentary tract or the digestive system
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P19/00—Drugs for skeletal disorders
- A61P19/08—Drugs for skeletal disorders for bone diseases, e.g. rachitism, Paget's disease
-
- C—CHEMISTRY; METALLURGY
- C12—BIOCHEMISTRY; BEER; SPIRITS; WINE; VINEGAR; MICROBIOLOGY; ENZYMOLOGY; MUTATION OR GENETIC ENGINEERING
- C12P—FERMENTATION OR ENZYME-USING PROCESSES TO SYNTHESISE A DESIRED CHEMICAL COMPOUND OR COMPOSITION OR TO SEPARATE OPTICAL ISOMERS FROM A RACEMIC MIXTURE
- C12P7/00—Preparation of oxygen-containing organic compounds
- C12P7/40—Preparation of oxygen-containing organic compounds containing a carboxyl group including Peroxycarboxylic acids
-
- C—CHEMISTRY; METALLURGY
- C12—BIOCHEMISTRY; BEER; SPIRITS; WINE; VINEGAR; MICROBIOLOGY; ENZYMOLOGY; MUTATION OR GENETIC ENGINEERING
- C12P—FERMENTATION OR ENZYME-USING PROCESSES TO SYNTHESISE A DESIRED CHEMICAL COMPOUND OR COMPOSITION OR TO SEPARATE OPTICAL ISOMERS FROM A RACEMIC MIXTURE
- C12P7/00—Preparation of oxygen-containing organic compounds
- C12P7/40—Preparation of oxygen-containing organic compounds containing a carboxyl group including Peroxycarboxylic acids
- C12P7/42—Hydroxy-carboxylic acids
-
- A—HUMAN NECESSITIES
- A23—FOODS OR FOODSTUFFS; TREATMENT THEREOF, NOT COVERED BY OTHER CLASSES
- A23V—INDEXING SCHEME RELATING TO FOODS, FOODSTUFFS OR NON-ALCOHOLIC BEVERAGES AND LACTIC OR PROPIONIC ACID BACTERIA USED IN FOODSTUFFS OR FOOD PREPARATION
- A23V2002/00—Food compositions, function of food ingredients or processes for food or foodstuffs
Definitions
- the present invention relates to a method for producing 1,4-dihydroxy-2-naphthoic acid (hereinafter also referred to as DHNA) at a high concentration using fermentation of propionic acid bacteria, and a technique for improving the flavor of a culture thereof.
- DHNA 1,4-dihydroxy-2-naphthoic acid
- DHNA has conventionally been known to be useful as an industrial material as a dye, a pigment, and a photosensitive material, and various synthetic methods have been developed by organic chemical synthesis methods.
- the present inventors studied alternative DHNA production methods and found that DHNA was produced in large quantities in and out of the cells by propionic acid bacteria, and the DHNA-containing composition collected from this culture, or 1 , 4-Dihydroxy-2-naphthoic acid or its salt has the effect of reducing the abdominal discomfort seen when ingesting milk with lactose intolerance, and that it is useful for the prevention and treatment of metabolic bone disease (Patent Document 1).
- Patent Document 1 4-Dihydroxy-2-naphthoic acid or its salt
- Patent Document 1 International Publication No. WO03Z016544 pamphlet
- the present inventors have conducted intensive studies from various angles to obtain a DHNA-containing composition with reduced bitterness.
- the culture medium was air-ventilated at a certain time during fermentation of propionic acid bacteria. This led to a useful new finding that the concentration of DHNA in the culture was increased. It was also found that the DHNA concentration was increased by adding a carbon source of propionic acid bacteria to the culture after culturing and storing at low temperature under weak alkaline conditions, even though the culturing was completed. .
- the DHNA-containing composition obtained by brute force suppresses bitterness, It was found that the taste was good and that it was useful as a food or drink or pharmaceutical.
- An object of the present invention is to provide a method for producing 1,4-dihydroxy-2 naphthoic acid, which comprises culturing by aeration in a medium.
- the present invention provides a method for culturing a 1,4-dihydroxy-2 naphthoic acid-producing bacterium belonging to a propionic acid bacterium under anaerobic conditions, adding a carbon source to the obtained culture, and culturing the solution at a temperature of 3 to 20 ° under a weak alkali.
- the present invention provides a method for producing 1,4-dihydroxy-2 naphthoic acid, which is stored in C.
- the present invention provides a method for culturing a 1,4-dihydroxy-2 naphthoic acid-producing bacterium belonging to a propionic acid bacterium under an anaerobic condition, and when the carbon source concentration in the medium becomes 3.5% by mass or less,
- a method for producing 1,4-dihydroxy-2 naphthoic acid characterized in that the culture is obtained by aeration, and a carbon source is added to the resulting culture and stored at 3-20 ° C under weak alkaline conditions. Is what you do.
- the present invention also provides a 1,4-dihydroxy-2 naphthoic acid-containing composition obtained as described above.
- the present invention provides a food and beverage for improving abdominal discomfort symptoms, an agent for improving abdominal discomfort symptoms, an agent for preventing and treating metabolic bone diseases, which comprises the 1,4-dihydroxy-2 naphthoic acid-containing composition obtained as described above as an active ingredient. It is intended to provide a food or drink or an agent for preventing or treating metabolic bone disease.
- the present invention also relates to a food and drink for improving abdominal discomfort symptoms, an agent for improving abdominal discomfort symptoms, a food and drink for preventing and treating metabolic bone disease, or a metabolic food or drink, of the 1,4-dihydroxy-2 naphthoic acid-containing composition obtained as described above.
- the present invention also provides use of the composition for the prevention and treatment of bone diseases.
- the present invention also provides administration of an effective amount of the 1,4-dihydroxy-2 naphthoic acid-containing composition obtained as described above. It is intended to provide a method for treating abdominal discomfort or a method for treating metabolic bone disease.
- DHNA can be produced efficiently, and the obtained DHNA-containing composition has a good flavor and is useful as a food, beverage, or pharmaceutical.
- FIG. 1 shows the change in DHNA concentration when the switching time to air rate is changed.
- FIG. 2 shows the change in lactose concentration when the switching time to air rate is changed.
- FIG. 3 shows the timing of switching to the air rate and changes in the number of propionic acid bacteria.
- FIG. 4 shows the concentration of propionic acid when the switching time to the air rate is changed.
- FIG. 5 shows the acetic acid concentration when the switching time to the air rate is changed.
- FIG. 6 shows the DHNA concentration when the flow rate of the air rate was changed.
- the propionic acid bacterium used in the production method of the present invention is not particularly limited as long as it is a DHNA-producing bacterium, and a bacterium belonging to the genus Propio-bataterum is preferred.
- a bacterium belonging to the genus Propio-bataterum is preferred.
- propioninobacterium ' freudenreichii Propio-bacterium 'Tenny (P. thoenii), Propio-batatherimu' P. acidipropionici (P. acidipropionici) ', Propio-batatherimu' P. jensenii '
- Examples include butterium 'Avidum' (P. avidum), propio-bataterum 'Aknes (P.
- P. freudenreich ii IFO 12424 P. freudenreichii ATCC 6207, and P. freudenreichii ET-3 (FERM P-18454) are particularly preferred!
- the medium used in the method of the present invention is preferably a medium containing a carbon source.
- the carbon source refers to a carbon source that can be assimilated by propionic acid bacteria.
- lactose glucose, lactic acid, glycerol, dartene, cellulose and the like can be mentioned, and lactose is particularly preferred.
- the content of the carbon source in the medium before the start of the culture is preferably 418% by mass, more preferably 417% by mass, and particularly preferably 417% by mass.
- a medium containing lactose as a carbon source includes whey powder, power zein, skim milk powder, or whey protein concentration obtained by dialyzing whey to reduce the lactose content.
- a whey protein isolate obtained by further separating the lactose content from the condensate or the lactose content may be mentioned. These can be used as they are or after being treated with protease, and can be used as a carbon source that can be used as a carbon source for assimilating peptone such as yeast extract and trypticase, and propionic acid bacteria such as glucose, lactose, and lactase-treated lactase.
- the medium can be prepared by adding the medium.
- the following is an example of a method for preparing a medium containing a protease-treated skim milk powder as a medium material.
- the skim milk powder is dissolved in water so as to have a concentration of 10 to 20% by mass, and the temperature is adjusted to 47 ° C.
- protease is added at 2.5% by mass of the skim milk powder to decompose the protein in the skim milk solution.
- the protease include proteolytic enzymes derived from animals and plants or bacteria, and can be used regardless of acidity, neutrality, or alkalinity.
- the digestion is performed for 6 hours, the temperature during the digestion is adjusted to 47 ° C and the pH is adjusted to 6.8. To adjust the pH, use a potassium carbonate aqueous solution. When the decomposition by the protease is completed, the skim milk solution is heated to 80 ° C.
- Sterilization conditions are 7 minutes or more at 121 ° C when using an autoclave, and 4 seconds or more at 140 ° C or more when a sterile plate is used.
- the culture medium thus obtained usually contains lactose in an amount of 45% by mass.
- the culture is performed under anaerobic conditions.
- the anaerobic condition can be, for example, one or a combination of two or more of nitrogen gas, helium gas, argon gas, hydrogen gas, and other inert gas. . More specifically, nitrogen gas, carbon dioxide gas, etc. are flowed through the top of the fermenter by aeration on the top surface, stirring is performed, and the medium temperature is adjusted to 33 ° C. When the medium temperature is stabilized at 33 ° C, inoculate a starter for propionic acid bacteria and start cultivation under anaerobic conditions. As the starter, an activated culture solution of propionic acid bacteria, a cell concentrate of the culture solution, and the like can be used.
- the amount to be added to the medium is about 0.05% of the medium in the former case, and about 0.3% in the latter case as a guideline.These amounts can be changed even if necessary as needed. .
- Culture is performed under the conditions of a culture temperature of 20 to 40 ° C and a medium pH of neutral to slightly acidic (preferably pH 5.5 to 7.5).
- a known neutralizing agent such as an aqueous solution of potassium carbonate or an aqueous solution of sodium carbonate can be used.
- the time when the air rate is started is when the carbon source concentration in the culture medium becomes 3.5% by mass or less.
- One guideline is 24 hours before the carbon source of the propionic acid bacterium dies. You. It is more preferable to start the aeration when the carbon source concentration reaches 1.0 to 3.5% by mass, particularly 1.5 to 3.0% by mass.
- propionic acid bacteria By aeration when the carbon source concentration falls below 3.5% by mass, propionic acid bacteria also consume cacaine and propionic acid as a carbon source, and eventually the carbon source almost depletes. .
- the number of propionic acid bacteria in the culture medium at the start of aeration should be 1.OX 10 1G cfu / mL (10.0 log cfu / mL) or more, and 1.4 X 10 1G cfuZmL (10.1 log cfuZmL) or more. preferable. By doing so, the carbon source in the medium can be almost depleted. In the above-mentioned lactose-containing medium and culture conditions, about 48 hours after the start of the culture, the lactose concentration becomes 3.5% by mass or less, and it is time to start the aeration.
- the amount of air supplied by the air rate is preferably an amount that stimulates propionic acid bacteria.
- a specific example on a laboratory scale (1.5 L capacity) is as follows.
- the air supply rate is 2 L or more for Z minutes.
- the amount is preferably 2 LZ minutes to 4 LZ minutes, but can be appropriately adjusted according to the capacity, stirring speed, apparatus and the like. If the amount of dissolved oxygen in the solution becomes unnecessarily high, growth of propionic acid bacteria is stopped, and DHNA production is stopped. Round.
- the culture is usually completed in about 168 hours from the start of the culture.
- Examples of the method of aeration include a method of inserting a porous ventilation tube into a culture medium and sending air over the entire surface of the tube, and a method of sending bubbles using a sparger.
- the DHNA accumulated in the medium and the cells can be stopped for culturing and immediately used for DHNA collection from the culture.
- the end point of the culture is about 3 to 5 days when the number of bacteria reaches the stationary phase and the carbon source in the medium dies.
- the culture may be the culture after the above-described aeration, or may be the culture after the completion of the culture under ordinary anaerobic or microaerobic conditions without passing through the aeration.
- the amount of the carbon source added to the culture is such that the carbon source concentration in the culture is 0.2 to 3.0% by mass, more preferably 0.4 to 2.5% by mass, particularly 0.8 to 2%. It is preferable to set the amount to 2% by mass.
- a base such as potassium carbonate, sodium carbonate or sodium phosphate to adjust the pH of the culture to 7-9, especially 7.5-8.5. Is preferred.
- the storage temperature is 3-20 ° C, particularly 3-15 ° C, and more preferably 5-15 ° C.
- the storage period is preferably 1 to 3 weeks, particularly preferably 1 to 2 weeks.
- the obtained culture is preferably subjected to adsorption chromatography.
- a reversed-phase adsorbent such as activated carbon or a synthetic adsorbent (for example, Diaion HP-20, manufactured by Mitsubishi Iridaku Co., Ltd.) can be widely used.
- the column is filled with the adsorbent and washed with 0.5% (wZv) sodium ascorbate aqueous solution.
- the obtained culture is added to a column (the passing solution is referred to as "pass"), and the water-soluble fraction is removed with a 0.5% (wZv) aqueous sodium ascorbate solution.
- Examples of DHNA salts include pharmaceutically or food acceptable salts.
- Representative salts include monovalent metal salts such as sodium, potassium, and lithium, and magnesium, calcium, and zinc. Examples thereof include polyvalent metal salts, and inorganic or organic amine salts such as ammonia and ethanolamine.
- salt exchange can also be performed by using a reaction known per se.
- the salt examples include salts with inorganic acids (eg, hydrochloric acid, phosphoric acid, hydrobromic acid, sulfuric acid) and organic acids (eg, formic acid, propionic acid, fumaric acid, maleic acid, succinic acid, tartaric acid, citrate) And malic acid, oxalic acid, benzoic acid, methanesulfonic acid and benzenesulfonic acid), but these are only examples, and the present invention is not limited to these salts.
- inorganic acids eg, hydrochloric acid, phosphoric acid, hydrobromic acid, sulfuric acid
- organic acids eg, formic acid, propionic acid, fumaric acid, maleic acid, succinic acid, tartaric acid, citrate
- malic acid oxalic acid
- benzoic acid methanesulfonic acid and benzenesulfonic acid
- DHNA is contained in the culture of the DHNA-producing bacteria (inside and inside or outside of the cells), the culture itself is used without application of adsorption chromatography using a rotary evaporator or the like.
- a composition containing a high concentration of DHNA can be obtained. It is also preferable to separate the cells from the culture by a usual centrifugation method and concentrate the supernatant.
- the composition thus obtained may be used in a liquid state or may be processed into a powder according to the form to be used.
- the DHNA-containing composition obtained by force exerts a high DHNA concentration, suppresses bitterness, and has a good flavor. Therefore, the DHNA-containing composition of the present invention, or DHNA or a salt thereof, can be used in the form of a food or drink or a medicament, for example, by directly administering it as a medicament, or special food such as food for specified health use. By ingesting directly as intended foods or functional foods, or by adding various foods (milk, soft drinks, fermented milk, 1 dart, cheese, bread, biscuit, cracker, pizza crust, etc.), and ingesting it can improve intestinal flora and reduce abdominal discomfort seen when consuming milk. It can prevent and treat metabolic bone disease.
- water, protein, saccharide, lipid, vitamin, and minerals, organic acid, fruit juice, flavor, and the like can be combined as main components.
- whole milk powder, skim milk powder, partially skim milk powder, casein, whey powder, whey protein, whey protein concentrate, whey protein isolate, ⁇ -casein, ⁇ -casein, ⁇ -latatoglobulin, and lactalbumin Animal and plant proteins such as ratatoferrin, soy protein, chicken egg protein, meat protein, etc., and their various hydrolysates, butter, whey minerals, cream, whey, non-protein nitrogen, sialic acid, phospholipids, lactose, etc.
- Animal oils such as fish oil; palm oil, safflower oil, corn oil, Vegetable oils and fats such as seed oil and coconut oil, their fractionated oils, hydrogenated oils, and vegetable oils such as transesterified oils; vitamin ⁇ , vitamin ⁇ , vitamin C, erythorbic acid, vitamin D, vitamin E,
- vitamins such as vitamin K group, vitamin P, vitamin Q, niacin, nicotinic acid, pantothenic acid, piotin, inosit, choline, folic acid; calcium, potassium, magnesium, sodium, chlorine, copper, iron, manganese, zinc, Minerals such as selenium, fluorine, silicon, and iodine; organic acids and organic acids
- Liquid, solid (including granules, powders, tablets, and gels) and semi-solids It may be in any form (including jelly), paste, emulsified, and the like.
- composition according to the present invention or DHNA or a salt thereof When used as a pharmaceutical, it can be administered in various forms. Examples of the form include oral administration by tablets, capsules, granules, powders, syrups and the like. These various products
- the agent can be used in the pharmaceutical formulation technical field such as excipients, binders, disintegrants, lubricants, flavors, flavoring agents, solubilizers, suspending agents, coating agents, etc. in the main agent according to the usual method. It can be formulated using known auxiliaries.
- the quantification of DHNA was performed according to the method described on page 9 of WO03Z016544.
- the lactose concentration was measured by a flow injection analysis method using a lactose electrode (using a flow injection analyzer, Bio Flow Analyzer (trade name) manufactured by Oji Scientific Instruments).
- the number of propionic acid bacteria was measured on a BL agar medium.
- the concentrations of propionic acid and acetic acid were measured by an HPLC method (column: RS pa k KC-811 + pre-column KCG, detection: UV445 nm).
- skim milk powder manufactured by Meiji Dairies Co., Ltd.
- 100 g of water 150 g was dissolved in 100 g of water, and the temperature was adjusted to 47 ° C.
- protease was added, and protein degradation was performed at 47 ° C for 6 hours.
- the pH during protein degradation was adjusted to 6.6-6.8 using potassium carbonate solution.
- the protease was inactivated by heating to 80 ° C and holding for 10 minutes, 7.5 g of brewer's yeast extract was added, and the pH was adjusted to 6.95 using an aqueous potassium carbonate solution.
- the volume of the solution was adjusted to 1500 mL with water, and the solution was placed in a 2 L fermenter to sterilize the medium. Sterilization conditions were 121 ° C for 7 minutes.
- Nitrogen gas was passed through the fermenter, and the temperature of the medium was stabilized at 33 ° C. Then, 0.75 mL of a freeze concentration starter (P. freudenreichii ET-3) was added, and culture was started. During fermentation, the temperature was adjusted to 33 ° C, the pH was adjusted to 6.5, and nitrogen gas was aerated. The pH was adjusted using a 40% (wtZ wt) aqueous potassium carbonate solution. The following five types of culture methods were implemented.
- skim milk powder manufactured by Meiji Dairies Co., Ltd.
- the protein was decomposed at 47 ° C for 3 hours after adding 3.75g of protease to the mixture.
- ⁇ ⁇ was adjusted using an aqueous potassium carbonate solution at 6.6-6.8.
- the protease was inactivated by heating to 80 ° C and holding for 10 minutes, 7.5 g of beer yeast extract and 15 g of lactose were added, and the pH was adjusted to 6.95 using an aqueous potassium carbonate solution. did.
- the volume of the solution was adjusted to 1500 mL with water, and the solution was placed in a 2 L fermenter, and the medium was sterilized (lactose concentration mass: about 6.1%). Sterilization conditions were 121 ° C for 7 minutes.
- Example 2 The DHNA-containing culture obtained in Example 2 was supplemented with sodium ascorbate (1.0%) and lactose (2.0%), and the pH was adjusted to 8.0. As a result of storage at ° C for 2 weeks, the DHNA concentration was 55 ⁇ gZmL. When lactose was replaced with glucose and stored in the same manner, the DHNA concentration increased from the end of the culture.
- the DHNA-containing culture obtained in Example 1 was added to 120 g of plain yogurt (manufactured by Meiji Dairies Co., Ltd.), and the sensory evaluation of the prepared yogurt is shown in Tables 1 and 2.
- the yogurt to which the DHNA-containing culture obtained by the method of the present invention was added had a sour taste as compared with the conventional method in which the DHNA concentration was high (the DHNA-containing culture obtained in Comparative Example was added to plain yogurt). It was confirmed that no bitterness was felt.
- a culture having a DHNA concentration of 48 gZmL was obtained.
- the lactose concentration 72 hours after the start of the culture was about 3.0% by mass, and the number of propionic acid bacteria was 2.9 ⁇ 10 1 G cfu / mL.
- the DHNA-containing culture obtained in Example 5 was added with 1.0% sodium ascorbate and 1.0% lactose to adjust the pH to 8.0, and then adjusted to 10 ° C. As a result of storage for 2 weeks, the DHNA concentration was 60 ⁇ g ZmL.
Landscapes
- Life Sciences & Earth Sciences (AREA)
- Chemical & Material Sciences (AREA)
- Health & Medical Sciences (AREA)
- Engineering & Computer Science (AREA)
- Organic Chemistry (AREA)
- General Health & Medical Sciences (AREA)
- Polymers & Plastics (AREA)
- Food Science & Technology (AREA)
- Microbiology (AREA)
- Zoology (AREA)
- Wood Science & Technology (AREA)
- Public Health (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Pharmacology & Pharmacy (AREA)
- Animal Behavior & Ethology (AREA)
- Medicinal Chemistry (AREA)
- General Chemical & Material Sciences (AREA)
- Veterinary Medicine (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Nutrition Science (AREA)
- Biochemistry (AREA)
- Epidemiology (AREA)
- Genetics & Genomics (AREA)
- General Engineering & Computer Science (AREA)
- Biotechnology (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Physical Education & Sports Medicine (AREA)
- Mycology (AREA)
- Orthopedic Medicine & Surgery (AREA)
- Rheumatology (AREA)
- Preparation Of Compounds By Using Micro-Organisms (AREA)
- Micro-Organisms Or Cultivation Processes Thereof (AREA)
- Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
- Coloring Foods And Improving Nutritive Qualities (AREA)
Abstract
Description
Claims
Priority Applications (10)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
AU2004278620A AU2004278620B2 (en) | 2003-10-01 | 2004-09-30 | Process for producing 1,4-dihydroxy-2-naphthoic acid |
EP12001429.5A EP2463375B1 (en) | 2003-10-01 | 2004-09-30 | Food and beverages for treating abdominal discomfort |
EP12001430.3A EP2463376B1 (en) | 2003-10-01 | 2004-09-30 | Food and beverages for treating metabolic osteopathy |
US10/574,283 US7507563B2 (en) | 2003-10-01 | 2004-09-30 | Process for producing 1, 4-dihydroxy-2-naphthoic acid |
EP04788422.6A EP1669458B1 (en) | 2003-10-01 | 2004-09-30 | Process for producing 1,4-dihydroxy-2-naphthoic acid |
JP2005514449A JP4613132B2 (ja) | 2003-10-01 | 2004-09-30 | 1,4−ジヒドロキシ−2−ナフトエ酸の製造法 |
CA2540507A CA2540507C (en) | 2003-10-01 | 2004-09-30 | Process for producing 1,4-dihydoxy-2-naphthoic acid |
NZ546286A NZ546286A (en) | 2003-10-01 | 2004-09-30 | Process for producing 1,4-dihydroxy-2-naphthoic acid |
KR1020067006133A KR101116244B1 (ko) | 2003-10-01 | 2006-03-29 | 1,4-디히드록시-2-나프토산의 제조법 |
US12/187,065 US8758842B2 (en) | 2003-10-01 | 2008-08-06 | Process for producing 1,4-dihydroxy-2-naphthoic acid |
Applications Claiming Priority (2)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
JP2003-343211 | 2003-10-01 | ||
JP2003343211 | 2003-10-01 |
Publications (1)
Publication Number | Publication Date |
---|---|
WO2005033323A1 true WO2005033323A1 (ja) | 2005-04-14 |
Family
ID=34419286
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
PCT/JP2004/014394 WO2005033323A1 (ja) | 2003-10-01 | 2004-09-30 | 1,4−ジヒドロキシ−2−ナフトエ酸の製造法 |
Country Status (9)
Country | Link |
---|---|
US (2) | US7507563B2 (ja) |
EP (3) | EP2463375B1 (ja) |
JP (1) | JP4613132B2 (ja) |
KR (1) | KR101116244B1 (ja) |
CN (1) | CN100422337C (ja) |
AU (1) | AU2004278620B2 (ja) |
CA (1) | CA2540507C (ja) |
NZ (1) | NZ546286A (ja) |
WO (1) | WO2005033323A1 (ja) |
Cited By (1)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
JP2014196355A (ja) * | 2008-02-29 | 2014-10-16 | 株式会社明治 | 抗アレルギー剤 |
Families Citing this family (5)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
KR20100087078A (ko) * | 2007-11-27 | 2010-08-03 | 메이지뉴교오가부시기가이샤 | 유산균의 생잔성 향상제 및 생잔성 향상 방법, 및 식품 조성물 |
US11179427B2 (en) | 2013-01-21 | 2021-11-23 | Eth Zurich | Baby food composition comprising viable propionic acid-producing bacteria |
WO2016183535A1 (en) | 2015-05-14 | 2016-11-17 | University Of Puerto Rico | Methods for restoring microbiota of newborns |
WO2017117142A1 (en) | 2015-12-28 | 2017-07-06 | New York University | Device and method of restoring microbiota of newborns |
CN111227038B (zh) * | 2018-11-29 | 2023-02-24 | 内蒙古伊利实业集团股份有限公司 | 一种双发酵双蛋白乳饮料及其制备方法 |
Citations (3)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
ES2102332A1 (es) * | 1996-01-03 | 1997-07-16 | Invest Y Desarrollo Agroindust | Procedimiento para la produccion de vitamina b12 a partir de residuos contaminantes de las industrias citricola. |
JP2002540760A (ja) * | 1998-12-18 | 2002-12-03 | デーエスエム・ナムローゼ・フェンノートシャップ | ビタミンb12の改良製造法 |
WO2003016544A1 (fr) * | 2001-08-10 | 2003-02-27 | Meiji Dairies Corporation | Procede d'elaboration d'acide 1,4-dihydroxy-2-naphtoique |
Family Cites Families (3)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
JP3315826B2 (ja) * | 1994-04-26 | 2002-08-19 | 明治乳業株式会社 | ビフィズス菌増殖促進組成物 |
JP3017456B2 (ja) | 1997-05-08 | 2000-03-06 | 明治乳業株式会社 | プロピオン酸菌の高濃度培養方法及び培養物ならびにその加工物 |
CN1764627B (zh) * | 2003-03-26 | 2016-05-25 | 株式会社明治 | 稳定1,4-二羟基-2-萘甲酸的方法 |
-
2004
- 2004-09-30 CN CNB2004800284544A patent/CN100422337C/zh active Active
- 2004-09-30 NZ NZ546286A patent/NZ546286A/en unknown
- 2004-09-30 EP EP12001429.5A patent/EP2463375B1/en not_active Not-in-force
- 2004-09-30 US US10/574,283 patent/US7507563B2/en active Active
- 2004-09-30 EP EP04788422.6A patent/EP1669458B1/en not_active Not-in-force
- 2004-09-30 JP JP2005514449A patent/JP4613132B2/ja not_active Expired - Fee Related
- 2004-09-30 CA CA2540507A patent/CA2540507C/en active Active
- 2004-09-30 EP EP12001430.3A patent/EP2463376B1/en not_active Not-in-force
- 2004-09-30 WO PCT/JP2004/014394 patent/WO2005033323A1/ja active Application Filing
- 2004-09-30 AU AU2004278620A patent/AU2004278620B2/en not_active Ceased
-
2006
- 2006-03-29 KR KR1020067006133A patent/KR101116244B1/ko active IP Right Grant
-
2008
- 2008-08-06 US US12/187,065 patent/US8758842B2/en active Active
Patent Citations (3)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
ES2102332A1 (es) * | 1996-01-03 | 1997-07-16 | Invest Y Desarrollo Agroindust | Procedimiento para la produccion de vitamina b12 a partir de residuos contaminantes de las industrias citricola. |
JP2002540760A (ja) * | 1998-12-18 | 2002-12-03 | デーエスエム・ナムローゼ・フェンノートシャップ | ビタミンb12の改良製造法 |
WO2003016544A1 (fr) * | 2001-08-10 | 2003-02-27 | Meiji Dairies Corporation | Procede d'elaboration d'acide 1,4-dihydroxy-2-naphtoique |
Non-Patent Citations (7)
Title |
---|
HOJO K. ET AL.: "Bifidogenic growth stimulator produced by propionic acid bacteria", MILK SCIENCE, vol. 49, no. 3, 2000, pages 161 - 167, XP008051230 * |
ISAWA K. ET AL.: "Isolation and identification of a new bifidogenic growth stimulator produced by propionibacterium freudenreichii ET-3", BIOSCI. BIOTECHNOL. BIOCHEM., vol. 66, no. 3, 2002, pages 679 - 681, XP008041283 * |
ISHIDA J. ET AL.: "Propion-sankin no kenki oyobi koki baiyo ni yoru bifidobacteria tokuiteki zoshoku sokushin busshitsu no seisan", 2002 NENDO (HEISEI 14 NENDO) JAPAN SOCIETY FOR BIOSCIENCE, BIOTECHNOLOGY, AND AGROCHEMISTRY TAIKAI KOEN YOSHISHU, 2002, pages 8, XP008107772 * |
MIYANO K. ET AL.: "Propion-sankin no roka baiyo oyobi shuki seigyo baiyo ni yoru vitamin B12 no seisan", THE SOCIETY OF CHEMICAL ENGINEERS, JAPAN SHUKI TAIKAI KENKYU HAPPYO KOEN YOSHISHU, vol. 30, no. 1, 1997, pages 316, XP008107770 * |
OKADA Y. ET AL.: "Propion-sankin ni yoru nyusei hakkobutsu seibun no DHNA no DSS choen ni taisuru koensho sayo no kento", DIGESTIVE ORGAN AND IMMUNOLOGY, no. 40, 10 June 2003 (2003-06-10), pages 58 - 60 * |
See also references of EP1669458A4 * |
YE K. ET AL.: "Efficient production of vitamin B12 from propionic acid bacteria under periodic variation of dissolved oxygen concentration", J. FERMENT. BIOENG., vol. 82, no. 5, 1996, pages 484 - 491, XP002105067 * |
Cited By (1)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
JP2014196355A (ja) * | 2008-02-29 | 2014-10-16 | 株式会社明治 | 抗アレルギー剤 |
Also Published As
Publication number | Publication date |
---|---|
JP4613132B2 (ja) | 2011-01-12 |
EP1669458A1 (en) | 2006-06-14 |
EP2463375B1 (en) | 2019-08-21 |
KR20060087594A (ko) | 2006-08-02 |
EP2463375A2 (en) | 2012-06-13 |
CA2540507A1 (en) | 2005-04-14 |
CA2540507C (en) | 2015-09-29 |
US20070066685A1 (en) | 2007-03-22 |
EP2463376A2 (en) | 2012-06-13 |
AU2004278620A1 (en) | 2005-04-14 |
US8758842B2 (en) | 2014-06-24 |
AU2004278620B2 (en) | 2010-07-15 |
US20090232940A1 (en) | 2009-09-17 |
NZ546286A (en) | 2008-10-31 |
KR101116244B1 (ko) | 2012-03-09 |
EP2463376A3 (en) | 2013-01-30 |
EP1669458B1 (en) | 2016-03-16 |
EP1669458A4 (en) | 2011-05-25 |
US7507563B2 (en) | 2009-03-24 |
EP2463375A3 (en) | 2013-01-30 |
EP2463376B1 (en) | 2019-08-28 |
CN100422337C (zh) | 2008-10-01 |
CN1860236A (zh) | 2006-11-08 |
JPWO2005033323A1 (ja) | 2007-11-15 |
Similar Documents
Publication | Publication Date | Title |
---|---|---|
JP2893953B2 (ja) | ビフィドバクテリウム菌の増殖促進剤 | |
Fernández-Garía et al. | The addition of oat fiber and natural alternative sweeteners in the manufacture of plain yogurt | |
US4702923A (en) | Lyophilized kefir yoghurt health food | |
JP4070721B2 (ja) | 1,4−ジヒドロキシ−2−ナフトエ酸の製造法 | |
WO2005099725A1 (ja) | 炎症性腸疾患予防および/または治療剤 | |
US10092605B2 (en) | Food composition, containing Lactococcus strain as active ingredient, for alleviating hangover | |
JP2000210075A (ja) | γ―アミノ酪酸高生産能を有する乳酸菌、及びその乳酸菌を使用したγ―アミノ酪酸高含有発酵食品とその製造法。 | |
US8758842B2 (en) | Process for producing 1,4-dihydroxy-2-naphthoic acid | |
JP2005218390A (ja) | 乳酸菌スターター、並びに豆乳発酵食品の製造方法及び豆乳発酵食品 | |
JPH08322464A (ja) | ビフィドバクテリウム菌を含有するヨーグルト及びその製造法 | |
JP2002058425A (ja) | 共役脂肪酸含有発酵食品及びその製造法 | |
JP2007104977A (ja) | γ−アミノ酪酸含有物の製造方法 | |
JP2008278776A (ja) | ラクトビオン酸含有発酵乳の製造方法 | |
JPH05168432A (ja) | オリゴ糖含有飲食品用素材、該飲食品用素材含有飲食品および該飲食品用素材の製造方法 | |
JP7513336B1 (ja) | γ-アミノ酪酸(GABA)含有粉末の製造方法およびそれを使用した製品 | |
RU2185436C2 (ru) | Консорциум бактерий для приготовления кисломолочных продуктов | |
JP3261571B2 (ja) | ビフィズス菌の生残性改善方法 | |
CN115851520B (zh) | 一种副干酪乳杆菌及其应用 | |
JP7484030B2 (ja) | シクロデキストリンにエクオールが包接された包接体の製造方法 | |
RU2108724C1 (ru) | Композиция для получения кисломолочного продукта детского питания и способ получения кисломолочного продукта | |
KR100225533B1 (ko) | 비피도박테리움 증식 촉진제(Biridobacterium growth promotr) | |
JP4653785B2 (ja) | 1,4−ジヒドロキシ−2−ナフトエ酸の製造法 |
Legal Events
Date | Code | Title | Description |
---|---|---|---|
WWE | Wipo information: entry into national phase |
Ref document number: 200480028454.4 Country of ref document: CN |
|
AK | Designated states |
Kind code of ref document: A1 Designated state(s): AE AG AL AM AT AU AZ BA BB BG BR BW BY BZ CA CH CN CO CR CU CZ DE DK DM DZ EC EE EG ES FI GB GD GE GH GM HR HU ID IL IN IS JP KE KG KP KR KZ LC LK LR LS LT LU LV MA MD MG MK MN MW MX MZ NA NI NO NZ OM PG PH PL PT RO RU SC SD SE SG SK SL SY TJ TM TN TR TT TZ UA UG US UZ VC VN YU ZA ZM ZW |
|
AL | Designated countries for regional patents |
Kind code of ref document: A1 Designated state(s): GM KE LS MW MZ NA SD SL SZ TZ UG ZM ZW AM AZ BY KG KZ MD RU TJ TM AT BE BG CH CY CZ DE DK EE ES FI FR GB GR HU IE IT LU MC NL PL PT RO SE SI SK TR BF BJ CF CG CI CM GA GN GQ GW ML MR NE SN TD TG |
|
121 | Ep: the epo has been informed by wipo that ep was designated in this application | ||
WWE | Wipo information: entry into national phase |
Ref document number: 2005514449 Country of ref document: JP |
|
WWE | Wipo information: entry into national phase |
Ref document number: 2004788422 Country of ref document: EP |
|
WWE | Wipo information: entry into national phase |
Ref document number: 2540507 Country of ref document: CA |
|
WWE | Wipo information: entry into national phase |
Ref document number: 1020067006133 Country of ref document: KR |
|
WWE | Wipo information: entry into national phase |
Ref document number: 2004278620 Country of ref document: AU |
|
WWE | Wipo information: entry into national phase |
Ref document number: 2007066685 Country of ref document: US Ref document number: 546286 Country of ref document: NZ Ref document number: 10574283 Country of ref document: US |
|
WWP | Wipo information: published in national office |
Ref document number: 2004278620 Country of ref document: AU |
|
WWP | Wipo information: published in national office |
Ref document number: 2004788422 Country of ref document: EP |
|
WWP | Wipo information: published in national office |
Ref document number: 1020067006133 Country of ref document: KR |
|
WWP | Wipo information: published in national office |
Ref document number: 10574283 Country of ref document: US |