JPS627194B2 - - Google Patents

Info

Publication number: JPS627194B2
Authority: JP; Japan
Prior art keywords: alkyl; dihydro; oxo; carboxylate; furan
Prior art date: 1975-08-04
Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.): Expired

Application number

JP51092742A

Other languages

English (en)

Japanese (ja)

Other versions

JPS5218866A (en

Inventor

Jei Uirusu Buraian

Fuishetsutei Junia Fuinku

Jii Eiraaman Robaato

Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)

FURITSUTSUSHE DOTSUJI ANDO ORUKOTSUTO Inc

Original Assignee

FURITSUTSUSHE DOTSUJI ANDO ORUKOTSUTO Inc

Priority date (The priority date is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the date listed.)

1975-08-04

Filing date

1976-08-03

Publication date

1987-02-16

1976-06-22 Priority claimed from US05/698,742 external-priority patent/US4109662A/en

1976-08-03 Application filed by FURITSUTSUSHE DOTSUJI ANDO ORUKOTSUTO Inc filed Critical FURITSUTSUSHE DOTSUJI ANDO ORUKOTSUTO Inc

1977-02-12 Publication of JPS5218866A publication Critical patent/JPS5218866A/ja

1987-02-16 Publication of JPS627194B2 publication Critical patent/JPS627194B2/ja

Status Granted legal-status Critical Current

Links

239000000203 mixture Substances 0.000 claims description 38
241000208125 Nicotiana Species 0.000 claims description 30
235000002637 Nicotiana tabacum Nutrition 0.000 claims description 30
125000004432 carbon atom Chemical group C* 0.000 claims description 10
125000000217 alkyl group Chemical group 0.000 claims description 9
-1 2,3-dihydro-3(1'-hydroxyethylidene)-2-oxo-5-methyl-furan-4-carboxylate Chemical compound 0.000 claims description 6
125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 6
125000000959 isobutyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])* 0.000 claims description 5
150000007942 carboxylates Chemical class 0.000 claims description 4
150000001875 compounds Chemical class 0.000 claims 2
239000000796 flavoring agent Substances 0.000 description 27
235000019634 flavors Nutrition 0.000 description 20
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 13
235000019264 food flavour enhancer Nutrition 0.000 description 8
YIKYNHJUKRTCJL-UHFFFAOYSA-N Ethyl maltol Chemical compound CCC=1OC=CC(=O)C=1O YIKYNHJUKRTCJL-UHFFFAOYSA-N 0.000 description 7
AHIIYYOECDXXPF-UHFFFAOYSA-N ethyl 4-(1-hydroxyethylidene)-2-methyl-5-oxofuran-3-carboxylate Chemical compound CCOC(=O)C1=C(C)OC(=O)C1=C(C)O AHIIYYOECDXXPF-UHFFFAOYSA-N 0.000 description 7
229940093503 ethyl maltol Drugs 0.000 description 7
235000013355 food flavoring agent Nutrition 0.000 description 7
DNIAPMSPPWPWGF-UHFFFAOYSA-N Propylene glycol Chemical compound CC(O)CO DNIAPMSPPWPWGF-UHFFFAOYSA-N 0.000 description 6
235000019441 ethanol Nutrition 0.000 description 5
FERIUCNNQQJTOY-UHFFFAOYSA-N Butyric acid Chemical compound CCCC(O)=O FERIUCNNQQJTOY-UHFFFAOYSA-N 0.000 description 4
229920003043 Cellulose fiber Polymers 0.000 description 4
125000000740 n-pentyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 4
125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 4
QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 3
WVDDGKGOMKODPV-UHFFFAOYSA-N Benzyl alcohol Chemical compound OCC1=CC=CC=C1 WVDDGKGOMKODPV-UHFFFAOYSA-N 0.000 description 3
RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 3
239000004097 EU approved flavor enhancer Substances 0.000 description 3
KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 3
125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 3
125000004177 diethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 3
125000001972 isopentyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])C([H])([H])* 0.000 description 3
125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 3
239000000047 product Substances 0.000 description 3
239000007787 solid Substances 0.000 description 3
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 3
WRMNZCZEMHIOCP-UHFFFAOYSA-N 2-phenylethanol Chemical compound OCCC1=CC=CC=C1 WRMNZCZEMHIOCP-UHFFFAOYSA-N 0.000 description 2
XPCTZQVDEJYUGT-UHFFFAOYSA-N 3-hydroxy-2-methyl-4-pyrone Chemical compound CC=1OC=CC(=O)C=1O XPCTZQVDEJYUGT-UHFFFAOYSA-N 0.000 description 2
OALYTRUKMRCXNH-UHFFFAOYSA-N 5-pentyloxolan-2-one Chemical compound CCCCCC1CCC(=O)O1 OALYTRUKMRCXNH-UHFFFAOYSA-N 0.000 description 2
ROWKJAVDOGWPAT-UHFFFAOYSA-N Acetoin Chemical compound CC(O)C(C)=O ROWKJAVDOGWPAT-UHFFFAOYSA-N 0.000 description 2
IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 2
XINCECQTMHSORG-UHFFFAOYSA-N Isoamyl isovalerate Chemical compound CC(C)CCOC(=O)CC(C)C XINCECQTMHSORG-UHFFFAOYSA-N 0.000 description 2
229910052799 carbon Inorganic materials 0.000 description 2
235000014171 carbonated beverage Nutrition 0.000 description 2
MMKRHZKQPFCLLS-UHFFFAOYSA-N ethyl myristate Chemical compound CCCCCCCCCCCCCC(=O)OCC MMKRHZKQPFCLLS-UHFFFAOYSA-N 0.000 description 2
230000008020 evaporation Effects 0.000 description 2
238000001704 evaporation Methods 0.000 description 2
239000012530 fluid Substances 0.000 description 2
238000007429 general method Methods 0.000 description 2
125000004051 hexyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 2
239000004615 ingredient Substances 0.000 description 2
MLFHJEHSLIIPHL-UHFFFAOYSA-N isoamyl acetate Chemical compound CC(C)CCOC(C)=O MLFHJEHSLIIPHL-UHFFFAOYSA-N 0.000 description 2
PQLMXFQTAMDXIZ-UHFFFAOYSA-N isoamyl butyrate Chemical compound CCCC(=O)OCCC(C)C PQLMXFQTAMDXIZ-UHFFFAOYSA-N 0.000 description 2
238000004519 manufacturing process Methods 0.000 description 2
ZKHQSQYLKSSYIP-UHFFFAOYSA-N methyl furan-3-carboxylate Chemical compound COC(=O)C=1C=COC=1 ZKHQSQYLKSSYIP-UHFFFAOYSA-N 0.000 description 2
125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 2
239000000779 smoke Substances 0.000 description 2
239000000126 substance Substances 0.000 description 2
238000006467 substitution reaction Methods 0.000 description 2
MWOOGOJBHIARFG-UHFFFAOYSA-N vanillin Chemical compound COC1=CC(C=O)=CC=C1O MWOOGOJBHIARFG-UHFFFAOYSA-N 0.000 description 2
FGQOOHJZONJGDT-UHFFFAOYSA-N vanillin Natural products COC1=CC(O)=CC(C=O)=C1 FGQOOHJZONJGDT-UHFFFAOYSA-N 0.000 description 2
235000012141 vanillin Nutrition 0.000 description 2
HNAGHMKIPMKKBB-UHFFFAOYSA-N 1-benzylpyrrolidine-3-carboxamide Chemical compound C1C(C(=O)N)CCN1CC1=CC=CC=C1 HNAGHMKIPMKKBB-UHFFFAOYSA-N 0.000 description 1
NOPJGNUVWOVEBH-UHFFFAOYSA-N 2-methylcyclopenten-1-ol Chemical compound CC1=C(O)CCC1 NOPJGNUVWOVEBH-UHFFFAOYSA-N 0.000 description 1
INAXVXBDKKUCGI-UHFFFAOYSA-N 4-hydroxy-2,5-dimethylfuran-3-one Chemical compound CC1OC(C)=C(O)C1=O INAXVXBDKKUCGI-UHFFFAOYSA-N 0.000 description 1
SMYLAMXMMOQASZ-UHFFFAOYSA-N 5-methyl-2-oxo-3H-furan-4-carboxylic acid Chemical compound CC1=C(C(O)=O)CC(=O)O1 SMYLAMXMMOQASZ-UHFFFAOYSA-N 0.000 description 1
ZCYVEMRRCGMTRW-UHFFFAOYSA-N 7553-56-2 Chemical compound [I] ZCYVEMRRCGMTRW-UHFFFAOYSA-N 0.000 description 1
229920013683 Celanese Polymers 0.000 description 1
QSJXEFYPDANLFS-UHFFFAOYSA-N Diacetyl Chemical group CC(=O)C(C)=O QSJXEFYPDANLFS-UHFFFAOYSA-N 0.000 description 1
LVGKNOAMLMIIKO-UHFFFAOYSA-N Elaidinsaeure-aethylester Natural products CCCCCCCCC=CCCCCCCCC(=O)OCC LVGKNOAMLMIIKO-UHFFFAOYSA-N 0.000 description 1
235000019501 Lemon oil Nutrition 0.000 description 1
HYMLWHLQFGRFIY-UHFFFAOYSA-N Maltol Natural products CC1OC=CC(=O)C1=O HYMLWHLQFGRFIY-UHFFFAOYSA-N 0.000 description 1
240000008790 Musa x paradisiaca Species 0.000 description 1
235000018290 Musa x paradisiaca Nutrition 0.000 description 1
VONGZNXBKCOUHB-UHFFFAOYSA-N Phenylmethyl butanoate Chemical compound CCCC(=O)OCC1=CC=CC=C1 VONGZNXBKCOUHB-UHFFFAOYSA-N 0.000 description 1
KEAYESYHFKHZAL-UHFFFAOYSA-N Sodium Chemical compound [Na] KEAYESYHFKHZAL-UHFFFAOYSA-N 0.000 description 1
PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 1
244000250129 Trigonella foenum graecum Species 0.000 description 1
235000001484 Trigonella foenum graecum Nutrition 0.000 description 1
235000019445 benzyl alcohol Nutrition 0.000 description 1
OBNCKNCVKJNDBV-UHFFFAOYSA-N butanoic acid ethyl ester Natural products CCCC(=O)OCC OBNCKNCVKJNDBV-UHFFFAOYSA-N 0.000 description 1
NORZZKKLCYMBBF-UHFFFAOYSA-N butyl butyryllactate Chemical compound CCCCOC(=O)C(C)OC(=O)CCC NORZZKKLCYMBBF-UHFFFAOYSA-N 0.000 description 1
235000012174 carbonated soft drink Nutrition 0.000 description 1
235000019506 cigar Nutrition 0.000 description 1
235000019504 cigarettes Nutrition 0.000 description 1
235000008504 concentrate Nutrition 0.000 description 1
239000012141 concentrate Substances 0.000 description 1
238000001816 cooling Methods 0.000 description 1
238000002425 crystallisation Methods 0.000 description 1
230000008025 crystallization Effects 0.000 description 1
239000000539 dimer Substances 0.000 description 1
239000003623 enhancer Substances 0.000 description 1
YHJXBVQTHBBOTN-UHFFFAOYSA-N ethyl 4-(1-hydroxy-3-methylbutylidene)-2-(2-methylpropyl)-5-oxofuran-3-carboxylate Chemical compound CCOC(=O)C1=C(CC(C)C)OC(=O)C1=C(O)CC(C)C YHJXBVQTHBBOTN-UHFFFAOYSA-N 0.000 description 1
XYIBRDXRRQCHLP-UHFFFAOYSA-N ethyl acetoacetate Chemical compound CCOC(=O)CC(C)=O XYIBRDXRRQCHLP-UHFFFAOYSA-N 0.000 description 1
LVGKNOAMLMIIKO-QXMHVHEDSA-N ethyl oleate Chemical compound CCCCCCCC\C=C/CCCCCCCC(=O)OCC LVGKNOAMLMIIKO-QXMHVHEDSA-N 0.000 description 1
229940093471 ethyl oleate Drugs 0.000 description 1
239000000706 filtrate Substances 0.000 description 1
238000009472 formulation Methods 0.000 description 1
239000008369 fruit flavor Substances 0.000 description 1
OALYTRUKMRCXNH-QMMMGPOBSA-N gamma-Nonalactone Natural products CCCCC[C@H]1CCC(=O)O1 OALYTRUKMRCXNH-QMMMGPOBSA-N 0.000 description 1
GFAZHVHNLUBROE-UHFFFAOYSA-N hydroxymethyl propionaldehyde Natural products CCC(=O)CO GFAZHVHNLUBROE-UHFFFAOYSA-N 0.000 description 1
239000005457 ice water Substances 0.000 description 1
229910052740 iodine Inorganic materials 0.000 description 1
239000011630 iodine Substances 0.000 description 1
229940117955 isoamyl acetate Drugs 0.000 description 1
229940094941 isoamyl butyrate Drugs 0.000 description 1
125000004491 isohexyl group Chemical group C(CCC(C)C)* 0.000 description 1
239000010501 lemon oil Substances 0.000 description 1
229940043353 maltol Drugs 0.000 description 1
238000000034 method Methods 0.000 description 1
238000002156 mixing Methods 0.000 description 1
229910052757 nitrogen Inorganic materials 0.000 description 1
239000012299 nitrogen atmosphere Substances 0.000 description 1
VWMVAQHMFFZQGD-UHFFFAOYSA-N p-Hydroxybenzyl acetone Natural products CC(=O)CC1=CC=C(O)C=C1 VWMVAQHMFFZQGD-UHFFFAOYSA-N 0.000 description 1
NJGBTKGETPDVIK-UHFFFAOYSA-N raspberry ketone Chemical compound CC(=O)CCC1=CC=C(O)C=C1 NJGBTKGETPDVIK-UHFFFAOYSA-N 0.000 description 1
239000011541 reaction mixture Substances 0.000 description 1
238000010992 reflux Methods 0.000 description 1
210000003296 saliva Anatomy 0.000 description 1
235000020374 simple syrup Nutrition 0.000 description 1
230000000391 smoking effect Effects 0.000 description 1
WBHQBSYUUJJSRZ-UHFFFAOYSA-M sodium bisulfate Chemical compound [Na+].OS([O-])(=O)=O WBHQBSYUUJJSRZ-UHFFFAOYSA-M 0.000 description 1
229910000342 sodium bisulfate Inorganic materials 0.000 description 1
239000012312 sodium hydride Substances 0.000 description 1
229910000104 sodium hydride Inorganic materials 0.000 description 1
229910052938 sodium sulfate Inorganic materials 0.000 description 1
235000011152 sodium sulphate Nutrition 0.000 description 1
239000002904 solvent Substances 0.000 description 1
239000007921 spray Substances 0.000 description 1
239000007858 starting material Substances 0.000 description 1
229940098465 tincture Drugs 0.000 description 1

Classifications

- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D307/00—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom
- C07D307/02—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom not condensed with other rings
- C07D307/34—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members
- 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
- A23L27/00—Spices; Flavouring agents or condiments; Artificial sweetening agents; Table salts; Dietetic salt substitutes; Preparation or treatment thereof
- A23L27/20—Synthetic spices, flavouring agents or condiments
- A23L27/205—Heterocyclic compounds
- A23L27/2052—Heterocyclic compounds having oxygen or sulfur as the only hetero atoms
- 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
- A23L27/00—Spices; Flavouring agents or condiments; Artificial sweetening agents; Table salts; Dietetic salt substitutes; Preparation or treatment thereof
- A23L27/20—Synthetic spices, flavouring agents or condiments
- A23L27/29—Fruit flavours
- 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
- A23L27/00—Spices; Flavouring agents or condiments; Artificial sweetening agents; Table salts; Dietetic salt substitutes; Preparation or treatment thereof
- A23L27/30—Artificial sweetening agents
- A—HUMAN NECESSITIES
- A24—TOBACCO; CIGARS; CIGARETTES; SIMULATED SMOKING DEVICES; SMOKERS' REQUISITES
- A24B—MANUFACTURE OR PREPARATION OF TOBACCO FOR SMOKING OR CHEWING; TOBACCO; SNUFF
- A24B15/00—Chemical features or treatment of tobacco; Tobacco substitutes, e.g. in liquid form
- A24B15/18—Treatment of tobacco products or tobacco substitutes
- A24B15/28—Treatment of tobacco products or tobacco substitutes by chemical substances
- A24B15/30—Treatment of tobacco products or tobacco substitutes by chemical substances by organic substances
- A24B15/36—Treatment of tobacco products or tobacco substitutes by chemical substances by organic substances containing a heterocyclic ring
- A24B15/40—Treatment of tobacco products or tobacco substitutes by chemical substances by organic substances containing a heterocyclic ring having only oxygen or sulfur as hetero atoms
- A24B15/403—Treatment of tobacco products or tobacco substitutes by chemical substances by organic substances containing a heterocyclic ring having only oxygen or sulfur as hetero atoms having only oxygen as hetero atoms
- A24B15/406—Treatment of tobacco products or tobacco substitutes by chemical substances by organic substances containing a heterocyclic ring having only oxygen or sulfur as hetero atoms having only oxygen as hetero atoms in a five-membered ring
- C—CHEMISTRY; METALLURGY
- C12—BIOCHEMISTRY; BEER; SPIRITS; WINE; VINEGAR; MICROBIOLOGY; ENZYMOLOGY; MUTATION OR GENETIC ENGINEERING
- C12G—WINE; PREPARATION THEREOF; ALCOHOLIC BEVERAGES; PREPARATION OF ALCOHOLIC BEVERAGES NOT PROVIDED FOR IN SUBCLASSES C12C OR C12H
- C12G3/00—Preparation of other alcoholic beverages
- C12G3/04—Preparation of other alcoholic beverages by mixing, e.g. for preparation of liqueurs
- C12G3/06—Preparation of other alcoholic beverages by mixing, e.g. for preparation of liqueurs with flavouring ingredients

Landscapes

Chemical & Material Sciences (AREA)
Organic Chemistry (AREA)
Life Sciences & Earth Sciences (AREA)
Health & Medical Sciences (AREA)
Engineering & Computer Science (AREA)
Nutrition Science (AREA)
Food Science & Technology (AREA)
Polymers & Plastics (AREA)
General Health & Medical Sciences (AREA)
Proteomics, Peptides & Aminoacids (AREA)
Genetics & Genomics (AREA)
Chemical Kinetics & Catalysis (AREA)
Toxicology (AREA)
Biochemistry (AREA)
Bioinformatics & Cheminformatics (AREA)
General Engineering & Computer Science (AREA)
General Chemical & Material Sciences (AREA)
Wood Science & Technology (AREA)
Zoology (AREA)
Seasonings (AREA)
Fats And Perfumes (AREA)
Manufacture Of Tobacco Products (AREA)
Furan Compounds (AREA)
Confectionery (AREA)

JP51092742A 1975-08-04 1976-08-03 Flavor composition Granted JPS5218866A (en)

Applications Claiming Priority (2)

Application Number	Priority Date	Filing Date	Title
US60148275A	1975-08-04	1975-08-04
US05/698,742 US4109662A (en)	1975-08-04	1976-06-22	Flavoring compositions containing alkyl-2,3-dihydro-3(1'-hydroxyalkylidene)-2-oxo-5-alkyl-furan-4-carboxylates

Publications (2)

Publication Number	Publication Date
JPS5218866A JPS5218866A (en)	1977-02-12
JPS627194B2 true JPS627194B2 (de)	1987-02-16

Family

ID=27083870

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
JP51092742A Granted JPS5218866A (en)	1975-08-04	1976-08-03	Flavor composition

Country Status (7)

Country	Link
JP (1)	JPS5218866A (de)
BE (1)	BE870873Q (de)
CA (1)	CA1062269A (de)
CH (1)	CH622685A5 (de)
DE (1)	DE2634509C2 (de)
GB (1)	GB1510060A (de)
NL (1)	NL7608662A (de)

Families Citing this family (1)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
JP4771318B2 (ja) *	2009-02-02	2011-09-14	株式会社吉野工業所	ヒンジ蓋体の射出成形金型

1976
- 1976-07-23 CA CA257,711A patent/CA1062269A/en not_active Expired
- 1976-07-29 GB GB31698/76A patent/GB1510060A/en not_active Expired
- 1976-07-31 DE DE2634509A patent/DE2634509C2/de not_active Expired
- 1976-08-03 JP JP51092742A patent/JPS5218866A/ja active Granted
- 1976-08-04 CH CH997276A patent/CH622685A5/de not_active IP Right Cessation
- 1976-08-04 NL NL7608662A patent/NL7608662A/xx not_active Application Discontinuation
1978
- 1978-09-29 BE BE2057318A patent/BE870873Q/xx not_active IP Right Cessation

Also Published As

Publication number	Publication date
CH622685A5 (en)	1981-04-30
BE870873Q (fr)	1979-01-15
DE2634509A1 (de)	1977-02-17
JPS5218866A (en)	1977-02-12
NL7608662A (nl)	1977-02-08
GB1510060A (en)	1978-05-10
CA1062269A (en)	1979-09-11
DE2634509C2 (de)	1985-09-12

Publication	Publication Date	Title
US3914227A (en)	1975-10-21	Certain cycloalkyl pyrazinyl ketones
US4126708A (en)	1978-11-21	Flavoring with 2-acyl-5-substituted thiatetrahydrofuran-4-ones
US4096158A (en)	1978-06-20	Process for preparing 5-acyl-2-(furfurylthio)dihydro-2,5-dialkyl-3-[2H]furanones
JPS627194B2 (de)	1987-02-16
US4070491A (en)	1978-01-24	2-Alkyl-4-phenyl-dihydropyrans and processes for augmenting the organoleptic properties of foodstuffs and tobacco using one or more of said pyrans
CN114516797B (zh)	2023-09-08	一种甲基环戊烯醇酮薄荷醇碳酸酯香料及其合成方法与应用
US4143173A (en)	1979-03-06	Flavoring with 5-acyl-2-(furfurylthio)dihydro-2,5-dialkyl-3-[2H]furanones
US4234616A (en)	1980-11-18	Flavoring with mixtures of 2,5-dialkyl dihydrofuranones and 2,4,5-trialkyl dihydrofuranones
US4992106A (en)	1991-02-12	Novel oxo-ionol carbonates useful as tobacco flavorants
US4115406A (en)	1978-09-19	2-Alkyl-4-phenyl-dihydropyrans and processes for augmenting the organoleptic properties of foodstuffs and tobacco using one or more of said pyrans
US4827012A (en)	1989-05-02	Oxo-ionol carbonates
US4512352A (en)	1985-04-23	Use of 4-methyl-2-hydroxy-benzaldehyde to improve the flavor characteristics of tobacco
JP2763637B2 (ja)	1998-06-11	タバコ風味剤として有用なオキソ―イオノールカーボネート
JPH0614846B2 (ja)	1994-03-02	ミルク様香気を有する香料添加剤
US4179526A (en)	1979-12-18	Uses of α-substituted alkylidene methionals in foodstuffs and flavors for foodstuffs
US4067344A (en)	1978-01-10	Novel tobacco product comprising one or more thiazolines and process
US4758680A (en)	1988-07-19	Pineapple ketone carbonate derivatives
JPS6343397B2 (de)	1988-08-30
US4154766A (en)	1979-05-15	Alpha-substituted alkylidene methionals and uses thereof in foodstuffs and flavors for foodstuffs
US4937229A (en)	1990-06-26	Pineapple ketone carbonate derivatives
US4382972A (en)	1983-05-10	Flavoring compositions and flavored comestibles containing alkyl 2,3-dihydro-3(1'-hydroxyalkylidene)-2-oxo-5-alkylfuran-4-carboxylates
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