CA2372612A1 - Method for preventing or minimizing biodegradation of a substance - Google Patents
Method for preventing or minimizing biodegradation of a substance Download PDFInfo
- Publication number
- CA2372612A1 CA2372612A1 CA002372612A CA2372612A CA2372612A1 CA 2372612 A1 CA2372612 A1 CA 2372612A1 CA 002372612 A CA002372612 A CA 002372612A CA 2372612 A CA2372612 A CA 2372612A CA 2372612 A1 CA2372612 A1 CA 2372612A1
- Authority
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- Prior art keywords
- compound
- odoriferous
- replaced
- substance
- product obtained
- Prior art date
- 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.)
- Abandoned
Links
- 238000000034 method Methods 0.000 title claims abstract description 47
- 239000000126 substance Substances 0.000 title claims abstract description 40
- 238000006065 biodegradation reaction Methods 0.000 title claims abstract description 13
- 150000001875 compounds Chemical class 0.000 claims abstract description 45
- 230000003287 optical effect Effects 0.000 claims description 36
- 235000019645 odor Nutrition 0.000 claims description 26
- 239000003205 fragrance Substances 0.000 claims description 20
- 239000002781 deodorant agent Substances 0.000 claims description 16
- DHMQDGOQFOQNFH-UHFFFAOYSA-N Glycine Chemical compound NCC(O)=O DHMQDGOQFOQNFH-UHFFFAOYSA-N 0.000 claims description 14
- FBPFZTCFMRRESA-FSIIMWSLSA-N D-Glucitol Natural products OC[C@H](O)[C@H](O)[C@@H](O)[C@H](O)CO FBPFZTCFMRRESA-FSIIMWSLSA-N 0.000 claims description 12
- 244000005700 microbiome Species 0.000 claims description 12
- 239000006210 lotion Substances 0.000 claims description 11
- 239000004471 Glycine Substances 0.000 claims description 7
- ZGUQGPFMMTZGBQ-UHFFFAOYSA-N [Al].[Al].[Zr] Chemical compound [Al].[Al].[Zr] ZGUQGPFMMTZGBQ-UHFFFAOYSA-N 0.000 claims description 7
- 229960002248 meradimate Drugs 0.000 claims description 7
- 150000003751 zinc Chemical class 0.000 claims description 7
- FBPFZTCFMRRESA-KVTDHHQDSA-N D-Mannitol Chemical compound OC[C@@H](O)[C@@H](O)[C@H](O)[C@H](O)CO FBPFZTCFMRRESA-KVTDHHQDSA-N 0.000 claims description 6
- FBPFZTCFMRRESA-JGWLITMVSA-N D-glucitol Chemical compound OC[C@H](O)[C@@H](O)[C@H](O)[C@H](O)CO FBPFZTCFMRRESA-JGWLITMVSA-N 0.000 claims description 6
- 235000010356 sorbitol Nutrition 0.000 claims description 6
- 229960002920 sorbitol Drugs 0.000 claims description 6
- QNAYBMKLOCPYGJ-UWTATZPHSA-N D-alanine Chemical compound C[C@@H](N)C(O)=O QNAYBMKLOCPYGJ-UWTATZPHSA-N 0.000 claims description 5
- QNAYBMKLOCPYGJ-UHFFFAOYSA-N D-alpha-Ala Natural products CC([NH3+])C([O-])=O QNAYBMKLOCPYGJ-UHFFFAOYSA-N 0.000 claims description 5
- 229940024606 amino acid Drugs 0.000 claims description 5
- 150000001413 amino acids Chemical class 0.000 claims description 5
- NOOLISFMXDJSKH-AEJSXWLSSA-N (+)-menthol Chemical compound CC(C)[C@H]1CC[C@H](C)C[C@@H]1O NOOLISFMXDJSKH-AEJSXWLSSA-N 0.000 claims description 4
- NEHNMFOYXAPHSD-JTQLQIEISA-N (S)-(-)-Citronellal Chemical compound O=CC[C@@H](C)CCC=C(C)C NEHNMFOYXAPHSD-JTQLQIEISA-N 0.000 claims description 4
- WHUUTDBJXJRKMK-GSVOUGTGSA-N D-glutamic acid Chemical compound OC(=O)[C@H](N)CCC(O)=O WHUUTDBJXJRKMK-GSVOUGTGSA-N 0.000 claims description 4
- JVTAAEKCZFNVCJ-REOHCLBHSA-N L-lactic acid Chemical compound C[C@H](O)C(O)=O JVTAAEKCZFNVCJ-REOHCLBHSA-N 0.000 claims description 4
- 239000003906 humectant Substances 0.000 claims description 4
- 239000002304 perfume Substances 0.000 claims description 4
- 241001465754 Metazoa Species 0.000 claims description 3
- 239000006096 absorbing agent Substances 0.000 claims description 3
- YCNZFPXXIWEFCF-UHFFFAOYSA-N alumane;sodium Chemical compound [Na].[AlH3] YCNZFPXXIWEFCF-UHFFFAOYSA-N 0.000 claims description 3
- 230000001166 anti-perspirative effect Effects 0.000 claims description 3
- 239000003213 antiperspirant Substances 0.000 claims description 3
- 239000010985 leather Substances 0.000 claims description 3
- 235000010355 mannitol Nutrition 0.000 claims description 3
- 238000009877 rendering Methods 0.000 claims description 3
- 235000012121 (S)-(-)-citronellal Nutrition 0.000 claims description 2
- 229930182843 D-Lactic acid Natural products 0.000 claims description 2
- RGHNJXZEOKUKBD-SQOUGZDYSA-N D-gluconic acid Chemical compound OC[C@@H](O)[C@@H](O)[C@H](O)[C@@H](O)C(O)=O RGHNJXZEOKUKBD-SQOUGZDYSA-N 0.000 claims description 2
- RGHNJXZEOKUKBD-UHFFFAOYSA-N D-gluconic acid Natural products OCC(O)C(O)C(O)C(O)C(O)=O RGHNJXZEOKUKBD-UHFFFAOYSA-N 0.000 claims description 2
- 229930182847 D-glutamic acid Natural products 0.000 claims description 2
- JVTAAEKCZFNVCJ-UWTATZPHSA-N D-lactic acid Chemical compound C[C@@H](O)C(O)=O JVTAAEKCZFNVCJ-UWTATZPHSA-N 0.000 claims description 2
- 241000238631 Hexapoda Species 0.000 claims description 2
- WHUUTDBJXJRKMK-VKHMYHEASA-N L-Glutamic acid Natural products OC(=O)[C@@H](N)CCC(O)=O WHUUTDBJXJRKMK-VKHMYHEASA-N 0.000 claims description 2
- RGHNJXZEOKUKBD-KLVWXMOXSA-N L-gluconic acid Chemical compound OC[C@H](O)[C@H](O)[C@@H](O)[C@H](O)C(O)=O RGHNJXZEOKUKBD-KLVWXMOXSA-N 0.000 claims description 2
- FBPFZTCFMRRESA-BXKVDMCESA-N L-mannitol Chemical group OC[C@H](O)[C@H](O)[C@@H](O)[C@@H](O)CO FBPFZTCFMRRESA-BXKVDMCESA-N 0.000 claims description 2
- 229930182842 L-mannitol Natural products 0.000 claims description 2
- 239000005667 attractant Substances 0.000 claims description 2
- 235000009508 confectionery Nutrition 0.000 claims description 2
- 229940022769 d- lactic acid Drugs 0.000 claims description 2
- 229950006191 gluconic acid Drugs 0.000 claims description 2
- 235000012208 gluconic acid Nutrition 0.000 claims description 2
- 229960002989 glutamic acid Drugs 0.000 claims description 2
- 239000002324 mouth wash Substances 0.000 claims description 2
- 239000004033 plastic Substances 0.000 claims description 2
- 229920003023 plastic Polymers 0.000 claims description 2
- 239000000843 powder Substances 0.000 claims description 2
- 235000019505 tobacco product Nutrition 0.000 claims description 2
- 238000011282 treatment Methods 0.000 claims description 2
- CDOSHBSSFJOMGT-SNVBAGLBSA-N (S)-linalool Chemical compound CC(C)=CCC[C@](C)(O)C=C CDOSHBSSFJOMGT-SNVBAGLBSA-N 0.000 claims 2
- 229960003849 (+)- linalool Drugs 0.000 claims 1
- KIACQSKGWSUCSG-RZFWHQLPSA-L (2R)-2-amino-4-methylsulfanylbutanoic acid cobalt(2+) 2-oxopropane-1,1-disulfonate Chemical group N[C@H](CCSC)C(=O)O.C(C)(=O)C(S(=O)(=O)[O-])S(=O)(=O)[O-].[Co+2] KIACQSKGWSUCSG-RZFWHQLPSA-L 0.000 claims 1
- KIACQSKGWSUCSG-FHNDMYTFSA-L (2S)-2-amino-4-methylsulfanylbutanoic acid cobalt(2+) 2-oxopropane-1,1-disulfonate Chemical compound N[C@@H](CCSC)C(=O)O.C(C)(=O)C(S(=O)(=O)[O-])S(=O)(=O)[O-].[Co+2] KIACQSKGWSUCSG-FHNDMYTFSA-L 0.000 claims 1
- 150000008574 D-amino acids Chemical class 0.000 claims 1
- 235000013334 alcoholic beverage Nutrition 0.000 claims 1
- 230000001476 alcoholic effect Effects 0.000 claims 1
- 239000003795 chemical substances by application Substances 0.000 claims 1
- 239000006071 cream Substances 0.000 claims 1
- 238000005108 dry cleaning Methods 0.000 claims 1
- 210000004400 mucous membrane Anatomy 0.000 claims 1
- 235000019520 non-alcoholic beverage Nutrition 0.000 claims 1
- 239000005871 repellent Substances 0.000 claims 1
- 230000002940 repellent Effects 0.000 claims 1
- 239000002453 shampoo Substances 0.000 claims 1
- NOOLISFMXDJSKH-KXUCPTDWSA-N (-)-Menthol Chemical compound CC(C)[C@@H]1CC[C@@H](C)C[C@H]1O NOOLISFMXDJSKH-KXUCPTDWSA-N 0.000 description 12
- NOOLISFMXDJSKH-UHFFFAOYSA-N DL-menthol Natural products CC(C)C1CCC(C)CC1O NOOLISFMXDJSKH-UHFFFAOYSA-N 0.000 description 9
- 102000004190 Enzymes Human genes 0.000 description 8
- 108090000790 Enzymes Proteins 0.000 description 8
- 229940041616 menthol Drugs 0.000 description 8
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 6
- 238000006243 chemical reaction Methods 0.000 description 6
- QNAYBMKLOCPYGJ-REOHCLBHSA-N L-alanine Chemical compound C[C@H](N)C(O)=O QNAYBMKLOCPYGJ-REOHCLBHSA-N 0.000 description 5
- 229960003767 alanine Drugs 0.000 description 5
- 230000006870 function Effects 0.000 description 5
- 239000004480 active ingredient Substances 0.000 description 4
- 235000004279 alanine Nutrition 0.000 description 4
- 235000001014 amino acid Nutrition 0.000 description 4
- 239000004615 ingredient Substances 0.000 description 4
- 230000000813 microbial effect Effects 0.000 description 4
- 229930014626 natural product Natural products 0.000 description 4
- 230000008786 sensory perception of smell Effects 0.000 description 4
- FFEARJCKVFRZRR-BYPYZUCNSA-N L-methionine Chemical compound CSCC[C@H](N)C(O)=O FFEARJCKVFRZRR-BYPYZUCNSA-N 0.000 description 3
- 238000006911 enzymatic reaction Methods 0.000 description 3
- 239000000463 material Substances 0.000 description 3
- 229960004452 methionine Drugs 0.000 description 3
- 210000002569 neuron Anatomy 0.000 description 3
- 239000000243 solution Substances 0.000 description 3
- GAMIYQSIKAOVTG-UHFFFAOYSA-L zinc;2-aminopentanedioate Chemical compound [Zn+2].[O-]C(=O)C(N)CCC([O-])=O GAMIYQSIKAOVTG-UHFFFAOYSA-L 0.000 description 3
- NEHNMFOYXAPHSD-SNVBAGLBSA-N (+)-Citronellal Chemical compound O=CC[C@H](C)CCC=C(C)C NEHNMFOYXAPHSD-SNVBAGLBSA-N 0.000 description 2
- XMGQYMWWDOXHJM-JTQLQIEISA-N (+)-α-limonene Chemical compound CC(=C)[C@@H]1CCC(C)=CC1 XMGQYMWWDOXHJM-JTQLQIEISA-N 0.000 description 2
- NFLGAXVYCFJBMK-BDAKNGLRSA-N (-)-menthone Chemical compound CC(C)[C@@H]1CC[C@@H](C)CC1=O NFLGAXVYCFJBMK-BDAKNGLRSA-N 0.000 description 2
- XMGQYMWWDOXHJM-SNVBAGLBSA-N (-)-α-limonene Chemical compound CC(=C)[C@H]1CCC(C)=CC1 XMGQYMWWDOXHJM-SNVBAGLBSA-N 0.000 description 2
- 239000011358 absorbing material Substances 0.000 description 2
- RWZYAGGXGHYGMB-UHFFFAOYSA-N anthranilic acid Chemical compound NC1=CC=CC=C1C(O)=O RWZYAGGXGHYGMB-UHFFFAOYSA-N 0.000 description 2
- 235000014633 carbohydrates Nutrition 0.000 description 2
- 150000001720 carbohydrates Chemical class 0.000 description 2
- 125000004432 carbon atom Chemical group C* 0.000 description 2
- 230000015556 catabolic process Effects 0.000 description 2
- 230000002354 daily effect Effects 0.000 description 2
- 238000006731 degradation reaction Methods 0.000 description 2
- 239000003974 emollient agent Substances 0.000 description 2
- 230000002045 lasting effect Effects 0.000 description 2
- 230000000873 masking effect Effects 0.000 description 2
- SOXAGEOHPCXXIO-DVOMOZLQSA-N menthyl anthranilate Chemical compound CC(C)[C@@H]1CC[C@@H](C)C[C@H]1OC(=O)C1=CC=CC=C1N SOXAGEOHPCXXIO-DVOMOZLQSA-N 0.000 description 2
- 229930182817 methionine Natural products 0.000 description 2
- 230000003020 moisturizing effect Effects 0.000 description 2
- 150000002894 organic compounds Chemical class 0.000 description 2
- 238000006467 substitution reaction Methods 0.000 description 2
- 229940099369 (+)- limonene Drugs 0.000 description 1
- 229960003595 (-)- limonene Drugs 0.000 description 1
- CXOYSEKQQVCMOU-UHFFFAOYSA-N (1-methyl-4-propan-2-ylcyclohexyl) 2-aminobenzoate Chemical compound C(C=1C(N)=CC=CC1)(=O)OC1(CCC(CC1)C(C)C)C CXOYSEKQQVCMOU-UHFFFAOYSA-N 0.000 description 1
- -1 (1R)-(-)-Menthyl Acetate (1S)-(+)-Menthyl Acetate Chemical compound 0.000 description 1
- 235000011976 (R)-(+)-citronellal Nutrition 0.000 description 1
- HBAQYPYDRFILMT-UHFFFAOYSA-N 8-[3-(1-cyclopropylpyrazol-4-yl)-1H-pyrazolo[4,3-d]pyrimidin-5-yl]-3-methyl-3,8-diazabicyclo[3.2.1]octan-2-one Chemical class C1(CC1)N1N=CC(=C1)C1=NNC2=C1N=C(N=C2)N1C2C(N(CC1CC2)C)=O HBAQYPYDRFILMT-UHFFFAOYSA-N 0.000 description 1
- 241000894006 Bacteria Species 0.000 description 1
- 102000005367 Carboxypeptidases Human genes 0.000 description 1
- 108010006303 Carboxypeptidases Proteins 0.000 description 1
- FFEARJCKVFRZRR-SCSAIBSYSA-N D-methionine Chemical compound CSCC[C@@H](N)C(O)=O FFEARJCKVFRZRR-SCSAIBSYSA-N 0.000 description 1
- 229930182818 D-methionine Natural products 0.000 description 1
- 206010013786 Dry skin Diseases 0.000 description 1
- 206010022998 Irritability Diseases 0.000 description 1
- FFEARJCKVFRZRR-UHFFFAOYSA-N L-Methionine Natural products CSCCC(N)C(O)=O FFEARJCKVFRZRR-UHFFFAOYSA-N 0.000 description 1
- 229930195722 L-methionine Natural products 0.000 description 1
- 239000004909 Moisturizer Substances 0.000 description 1
- 206010042496 Sunburn Diseases 0.000 description 1
- WHMDKBIGKVEYHS-IYEMJOQQSA-L Zinc gluconate Chemical compound [Zn+2].OC[C@@H](O)[C@@H](O)[C@H](O)[C@@H](O)C([O-])=O.OC[C@@H](O)[C@@H](O)[C@H](O)[C@@H](O)C([O-])=O WHMDKBIGKVEYHS-IYEMJOQQSA-L 0.000 description 1
- YAKZEVHORUHNLS-UHFFFAOYSA-K aluminum;sodium;2-hydroxypropanoate;chloride;hydroxide;hydrate Chemical compound O.[OH-].[Na+].[Al+3].[Cl-].CC(O)C([O-])=O YAKZEVHORUHNLS-UHFFFAOYSA-K 0.000 description 1
- 235000013361 beverage Nutrition 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- 229910052799 carbon Inorganic materials 0.000 description 1
- 210000004027 cell Anatomy 0.000 description 1
- 239000003153 chemical reaction reagent Substances 0.000 description 1
- 235000019504 cigarettes Nutrition 0.000 description 1
- 239000011248 coating agent Substances 0.000 description 1
- 238000000576 coating method Methods 0.000 description 1
- HOUREKNWYKCGJZ-UHFFFAOYSA-L cobalt(2+);2-oxopropane-1,1-disulfonate Chemical compound [Co+2].CC(=O)C(S([O-])(=O)=O)S([O-])(=O)=O HOUREKNWYKCGJZ-UHFFFAOYSA-L 0.000 description 1
- 238000011109 contamination Methods 0.000 description 1
- 239000002537 cosmetic Substances 0.000 description 1
- 239000000551 dentifrice Substances 0.000 description 1
- 230000037336 dry skin Effects 0.000 description 1
- 239000000975 dye Substances 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 230000002255 enzymatic effect Effects 0.000 description 1
- 230000032050 esterification Effects 0.000 description 1
- 238000005886 esterification reaction Methods 0.000 description 1
- 230000003203 everyday effect Effects 0.000 description 1
- 239000011152 fibreglass Substances 0.000 description 1
- 235000013305 food Nutrition 0.000 description 1
- 239000000499 gel Substances 0.000 description 1
- 239000011521 glass Substances 0.000 description 1
- 230000007062 hydrolysis Effects 0.000 description 1
- 238000006460 hydrolysis reaction Methods 0.000 description 1
- 238000011065 in-situ storage Methods 0.000 description 1
- 230000000977 initiatory effect Effects 0.000 description 1
- 239000003446 ligand Substances 0.000 description 1
- 238000004519 manufacturing process Methods 0.000 description 1
- 239000000203 mixture Substances 0.000 description 1
- 230000001333 moisturizer Effects 0.000 description 1
- 239000003973 paint Substances 0.000 description 1
- 238000002360 preparation method Methods 0.000 description 1
- 235000018102 proteins Nutrition 0.000 description 1
- 102000004169 proteins and genes Human genes 0.000 description 1
- 108090000623 proteins and genes Proteins 0.000 description 1
- 230000035807 sensation Effects 0.000 description 1
- 235000019615 sensations Nutrition 0.000 description 1
- 238000004904 shortening Methods 0.000 description 1
- 244000005714 skin microbiome Species 0.000 description 1
- 239000000344 soap Substances 0.000 description 1
- 239000000600 sorbitol Substances 0.000 description 1
- 241000894007 species Species 0.000 description 1
- 150000005846 sugar alcohols Chemical class 0.000 description 1
- 230000002459 sustained effect Effects 0.000 description 1
- 238000003786 synthesis reaction Methods 0.000 description 1
- 230000026683 transduction Effects 0.000 description 1
- 238000010361 transduction Methods 0.000 description 1
- 230000001052 transient effect Effects 0.000 description 1
- 229920002554 vinyl polymer Polymers 0.000 description 1
- 239000002023 wood Substances 0.000 description 1
- 229960000306 zinc gluconate Drugs 0.000 description 1
- 235000011478 zinc gluconate Nutrition 0.000 description 1
- 239000011670 zinc gluconate Substances 0.000 description 1
Classifications
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61Q—SPECIFIC USE OF COSMETICS OR SIMILAR TOILETRY PREPARATIONS
- A61Q13/00—Formulations or additives for perfume preparations
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K8/00—Cosmetics or similar toiletry preparations
- A61K8/18—Cosmetics or similar toiletry preparations characterised by the composition
- A61K8/30—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds
- A61K8/33—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds containing oxygen
- A61K8/34—Alcohols
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K8/00—Cosmetics or similar toiletry preparations
- A61K8/18—Cosmetics or similar toiletry preparations characterised by the composition
- A61K8/30—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds
- A61K8/33—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds containing oxygen
- A61K8/34—Alcohols
- A61K8/345—Alcohols containing more than one hydroxy group
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K8/00—Cosmetics or similar toiletry preparations
- A61K8/18—Cosmetics or similar toiletry preparations characterised by the composition
- A61K8/30—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds
- A61K8/33—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds containing oxygen
- A61K8/36—Carboxylic acids; Salts or anhydrides thereof
- A61K8/365—Hydroxycarboxylic acids; Ketocarboxylic acids
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K8/00—Cosmetics or similar toiletry preparations
- A61K8/18—Cosmetics or similar toiletry preparations characterised by the composition
- A61K8/30—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds
- A61K8/40—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds containing nitrogen
- A61K8/44—Aminocarboxylic acids or derivatives thereof, e.g. aminocarboxylic acids containing sulfur; Salts; Esters or N-acylated derivatives thereof
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K8/00—Cosmetics or similar toiletry preparations
- A61K8/18—Cosmetics or similar toiletry preparations characterised by the composition
- A61K8/30—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds
- A61K8/40—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds containing nitrogen
- A61K8/44—Aminocarboxylic acids or derivatives thereof, e.g. aminocarboxylic acids containing sulfur; Salts; Esters or N-acylated derivatives thereof
- A61K8/445—Aminocarboxylic acids or derivatives thereof, e.g. aminocarboxylic acids containing sulfur; Salts; Esters or N-acylated derivatives thereof aromatic, i.e. the carboxylic acid directly linked to the aromatic ring
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K8/00—Cosmetics or similar toiletry preparations
- A61K8/18—Cosmetics or similar toiletry preparations characterised by the composition
- A61K8/30—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds
- A61K8/40—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds containing nitrogen
- A61K8/44—Aminocarboxylic acids or derivatives thereof, e.g. aminocarboxylic acids containing sulfur; Salts; Esters or N-acylated derivatives thereof
- A61K8/447—Aminocarboxylic acids or derivatives thereof, e.g. aminocarboxylic acids containing sulfur; Salts; Esters or N-acylated derivatives thereof containing sulfur
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61L—METHODS OR APPARATUS FOR STERILISING MATERIALS OR OBJECTS IN GENERAL; DISINFECTION, STERILISATION OR DEODORISATION OF AIR; CHEMICAL ASPECTS OF BANDAGES, DRESSINGS, ABSORBENT PADS OR SURGICAL ARTICLES; MATERIALS FOR BANDAGES, DRESSINGS, ABSORBENT PADS OR SURGICAL ARTICLES
- A61L9/00—Disinfection, sterilisation or deodorisation of air
- A61L9/01—Deodorant compositions
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61Q—SPECIFIC USE OF COSMETICS OR SIMILAR TOILETRY PREPARATIONS
- A61Q15/00—Anti-perspirants or body deodorants
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61Q—SPECIFIC USE OF COSMETICS OR SIMILAR TOILETRY PREPARATIONS
- A61Q17/00—Barrier preparations; Preparations brought into direct contact with the skin for affording protection against external influences, e.g. sunlight, X-rays or other harmful rays, corrosive materials, bacteria or insect stings
- A61Q17/04—Topical preparations for affording protection against sunlight or other radiation; Topical sun tanning preparations
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61Q—SPECIFIC USE OF COSMETICS OR SIMILAR TOILETRY PREPARATIONS
- A61Q19/00—Preparations for care of the skin
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K2800/00—Properties of cosmetic compositions or active ingredients thereof or formulation aids used therein and process related aspects
- A61K2800/70—Biological properties of the composition as a whole
Landscapes
- Health & Medical Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- Veterinary Medicine (AREA)
- Animal Behavior & Ethology (AREA)
- General Health & Medical Sciences (AREA)
- Public Health (AREA)
- Epidemiology (AREA)
- Birds (AREA)
- Emergency Medicine (AREA)
- Dermatology (AREA)
- Fats And Perfumes (AREA)
- Cosmetics (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Confectionery (AREA)
- Emulsifying, Dispersing, Foam-Producing Or Wetting Agents (AREA)
- Solid-Sorbent Or Filter-Aiding Compositions (AREA)
Abstract
There is disclosed a method for preventing or minimizing biodegradation of a substance which normally contains a biodegradable compound which comprises replacing the compound with a corresponding lesser biodegradable compound providing the same desired functionality.
Description
Patent Application for METHOD FOR PREVENTING OR MINIMIZING
BIODEGRADATION OF A SUBSTANCE
Background of the Invention This invention relates to the extension of the useful lifetimes of biodegradable products by substituting lesser biodegradable ingredients having the same required functional characteristics such as odor. The practice of the invention relates to identifying such lesser biodegradable substances and substituting them, in existing or planned products, for those substances more subject to degradation.
Many substances lose functional lifetimes ?oecause of their vulnerability to microbial degradation. In a number of instances, substances with lesser biodegradability are substituted, such as polyvinyl for canvas, or fiberglass for wood. In these instances, the knowledge of the resistance of the selected substance to microbial decay is a factor in guiding the selection. Even though the immediate cost of the substitute is higher, the reduced biodegradability makes the substitution economical over the lifecycle of the product. There are, however, many instances in which there is no knowledge of longer lasting substitutes. These include instances in which other, perhaps initially more expensive, substances offer the same required functionality, but their greater resistance to biodegradation is unknown, as is, hence, their possible overall economic benefit. In other instances, in which unnatural optical isomers, stereoisomers, constitutional isomers, or other forms of the substances exist, useful lifetimes of the products can be extended by virtue of the relative nonbiodegradability of the unnatural or less common forms or substances. Lesser biodegradability is conferred by the fact that biodegrading bacteria, not having had long exposure to these substances, have not evolved the capability to metabolize them.
One aspect of this invention relates to a method for preventing or minimizing biodegradation of a substance which normally contains a naturally occurring optical isomer (or enantiomer, or optical stereoisomer). More particularly, this aspect of the invention relates to a process for rendering a fragrant substance, or surface, either bearing microorganisms or subject to deliberate or accidental contamination with microorganisms, odoriferous, e.g., fragrant, for an extended period of time.
Next to sight, the sense of smell is reported to be that sense most widely appreciated. It plays an important role in our everyday lives. For this reason, the fragrance industry has grown to its present enormous size. Commercially sold fragrances are based on natural products and synthetic ones. The latter have become of increasing importance as the science of chemistry has become more inventive. Natural fragrances have also been synthesized. However, many of the most pleasant, or otherwise desired odors are highly transient, requiring frequent re-applications, or disappearing after periods shorter than desired for the intended uses.
Fragrant or odoriferous preparations generally consist of two functional components: the odor-producing compound or material, and a vehicle which serves as a carrier for the fragrant molecules. Such vehicles have served their purpose when the fragrance has been adequately disseminated. These vehicles are generally short-chain organic compounds which then evaporate quite quickly. This leaves the generally longer-chain fragrant molecules in situ in the desired locations from which they, in turn, volatilize, although somewhat more slowly.
The sustained volatilization of these fragrant molecules achieves the desired effect by contacting the olfactories of the target persons or animals in the affected area.
While the fragrant compound applied to the site will ultimately be completely exhausted through volatilization, the full potential of this effective time is seldom, if ever, realized. This is because many fragrant molecules are biodegradable and they are generally applied to areas rich in microorganisms. An application is to skin, which is well known to be heavily laden with microorganisms. However, all other common surfaces are also heavily populated with microorganisms.
The interests of economy and personal appearance require that perfumes, for example, be applied sparingly. The biodegradability of the organic fragrance molecules results in the microbial populations attacking these molecules, metabolizing them and rendering the remains non-fragrant, less fragrant, or even of an undesirable odor. The otherwise expected useful time of the application of the product is thus effectively reduced.
In recent years, there has been a continuing replacement of natural fragrances with chemically synthesized molecules. Some are identical to natural fragrances, but are made synthetically more cheaply than can otherwise be obtained. Others are novel compounds, but these are also generally biodegradable. Both types of products suffer the same fate as described above for the natural fragrances.
Summary Of The Invention In the broadest aspect of this invention, there is provided a method for preventing or minimizing biodegradation of a substance which normally contains a biodegradable compound, which process comprises replacing the biodegradable compound with a corresponding lesser biodegradable compound providing the same desired functionality.
In accordance with one aspect of this invention, there is provided a method for preventing or minimizing biodegradation of a substance which normally contains a naturally occurring optical isomer, which process comprises replacing the naturally occurring optical isomer with the corresponding unnatural optical isomer.
Examples of such substances include fragrances, substances which contain fragrances, and nonfragrant substances which contain optical isomer(s), such as body lotions, soaps, deodorants, and dyes and paints.
In a preferred embodiment of this invention, there is provided a process for prolonging emanation of odors) from a substance or surface containing one or more odoriferous optically isomeric compounds and which substance or surface also contains or becomes contaminated with microorganisms, which process comprises selecting (an) unnatural optical isomers) of the compounds) to prevent or delay biodegradation of the odoriferous compound(s).
More generally, it has now been found that a functional substance or compound may retain the desired function for an extended period of time by substituting its non-naturally occurring optical stereoisomer, or an uncommon isomer or lesser biodegradable substance possessing the same functionality. The resulting substance will remain functional for a longer period of time than if the more naturally occurring form or the naturally occurring uncommon form or substance had been applied. This is because the non-naturally occurring form or the naturally occurring uncommon form or substance is non-biodegradable, or is of greatly reduced biodegradability since the microbial enzymes necessary to the biodegradation process can cope only with the more commonly occurring form or substance.
Detailed Description Of The Invention Some of the organic molecules synthesized for fragrance purposes, and some of the natural fragrance molecules which can be synthesized have structures which contain carbon atoms bonded to four different atomic groups. The four atomic groups can assume one of two opposite configurations about their central carbon atom.
For the purpose of chemical reactions, these configurations behave identically. Although little used as fragrances, amino acids and carbohydrates are -important examples of chirality, the occurrence of optical stereoisomers of the same molecule, and serve to illustrate the point. Virtually all amino acids in nature are of the optically stereoisomeric form designated "left handed", while natural carbohydrates occur almost exclusively in the optically stereoisomeric form called "right handed". (These common designations derive from their mirror images which demonstrate the chemical identity, and non-superimposability of the two forms of the same molecule.) The reason for the natural preference of one optical stereoisomer over its opposite form is unknown, but all known life forms follow this preference in their consumption and production of chiral organic compounds.
Some natural chemicals used in perfumery, and which have optical isomers, are listed in Table 1.
Table 1. Some Fragrances and their optical Isomers NATURAL OPTICAL ISOMER UNNATURAL OR LESS COMMON
NATURAL OPTICAL ISOMER
(1R, 2S, 5R) - (-) -Menthol (1S, 2R, 5S) - (+) -Menthol (R)-(+)-Citronellal (S)-(-)-Citronellal (+)-Limonene (-)-Limonene (-)-Menthone Three stereoisomers (1R)-(-)-Menthyl Acetate (1S)-(+)-Menthyl Acetate The strong preference, or specificity, for natural optical isomers displayed by biological entities is because virtually all biological reactions are conducted _ g _ through the participation of enzymes. From the time life originated, its first enzymes have consistently passed on their optical isomeric specificity to all life forms evolved down through the eons. Enzymes, being templates which position molecules for specific reactions, do distinguish between optical isomers of the same molecule.
Not being able to fit physically to the other optical isomer of the reactive molecular species, an enzyme cannot induce the reaction with the unnatural optical isomer.
The sense of smell has been attributed to enzymatic reactions: "Olfactory transduction begins with the binding of an odorant ligand to a protein receptor of the olfactory neuron cell surface, initiating a cascade of enzymatic reactions... "(Breer, H., Semin. Cell Bio1 5, 25, 1994; Sheppard, G.M., Neuron 13, 771, 1994, cited by Zhao, H. et a1, Science, 279, 237, 1998). A fundamental characteristic of enzymatic reactions is their specificity for the molecule they catalyze into reaction.
"Perhaps the most striking aspect of the specificity of enzymes is their ability to select between enantiomorphous compounds. This may be termed stereochemical specificity. For example, carboxypeptidase, which catalyzes the hydrolysis of carbobenzoxyglycyl-L-phenalalanine, has no measurable action on carbobenzoxyglycyl-D-phenalalanine. ...These examples of stereochemical specificity involve an absolute discrimination between enantiomorphs." (General Biochemistry, Fruton and Simmonds, eds, 3rd printing, p.
277, John Wiley & Sons, Inc., NY, 1960). A number of fragrant or odoriferous compounds are natural optical isomers. It would be expected that the unnatural enantiomers of these compounds would not trigger the sense of smell, because their molecules would not fit the protein (enzyme) receptor encountered. Since the enzyme receptors have evolved to fit with natural products only, the unnatural optical isomer would not fit, and, therefore, no odor-sensing reaction would be expected to occur with the neuron. However, the inventors have found that both the naturally occurring optical stereoisomer and the non-naturally occurring optical stereoisomer have the same odor, which demonstrates the core of this invention.
The odoriferous compounds used in the practice of the fragrance-prolonging aspect of this invention may be used in perfumes, eau de colognes, powders, mouth washes, dentifrices, confections, deodorants for personal and area uses, douches, hair applications, simulated odors for various products (such as leather odors for plastic upholstery), tobacco products, insect and animal repellants and attractants, and the wide variety of other products and uses for fragrances, masking odors, artificial odors, or other scents including those used in foodstuffs, beverages and the like.
EXAMPLE 1 - Menthol as a Fragrance The naturally-occurring optical isomer of menthol (1R,2S,5R)-(-) is used as a fragrance in a variety of products, such as perfumes, gums, and cigarettes. Both the natural and the unnatural (1S,2R,5S)-(+) optical isomer of menthol were obtained in 99o purity. A O.OO1M
solution of each enantiomer was prepared in reagent grade acetone. The solutions were allowed to equilibrate at room temperature for approximately one hour. Twenty drops of each solution were pipetted into separate glass Petri dishes. All glassware was clean. The acetone was then allowed to evaporate at room temperature. Human subjects then smelled the two Petri dishes separately and recorded any sensations. The subjects had been instructed to determine the presence of odor in the Petri dishes, and, if odor emanated from each, to determine whether the odors were the same or different. The test was performed twice on each of six human subjects, three female and three male. Each subject was given freshly prepared Petri dish servings to smell, and each immediately recorded his or her impressions without communicating with the other subjects.
All six subjects found that the unnatural form of menthol had odor. Moreover, all six found the odor of the unnatural form to be the same as that of the natural form. These results constitute evidence that the sense of smell is not enzymatic as heretofore believed by the scientific community. This unexpected finding constitutes the essential basis of the innovation claimed herein.
EXAMPLE 2 - Odor Absorber/Deodorant Objectionable odors may be absorbed by a variety of chemicals. Such chemicals may be added to an odoriferous material, or sprayed onto surfaces. This example relates to the use of zinc glutamate as an odor absorber. Zinc glutamate is normally used in the form of zinc salt of L-glutamic acid for this purpose. However, this form of the compound is readily biodegraded by microorganisms that are generally abundant in the treatment area. In this embodiment of the invention, the zinc salt of D-glutamic acid is substituted for the normal form, with the result that the odor-absorbing material, and, hence, odor removal function, lasts considerably longer than when the natural form of zinc glutamate is used.
Other chemicals with the deodorant function include zinc gluconate and sodium aluminum chlorohydroxy lactate.
D-gluconic acid and D-lactic acid are natural products, which are readily biodegradable. The use of their unnatural optical isomers, the zinc salt of L-gluconic acid and the sodium aluminum salt of L-lactic acid, instead of the natural products will result in the odor absorbing material lasting considerably longer.
EXAMPLE 3 - Humectant Besides their application in food, pharmaceutical and other industries, D-glucitol (i.e., sorbitol) and D-mannitol, the naturally occurring sugar alcohol, are commonly used as humectants (water-attracting/binding) as well as emollient ingredients in many cosmetic products, for example, in body lotions and sunblock. A
moisturizing lotion, in which D-glucitol is provided as a humectant and emollient, is applied to the skin daily or twice daily, especially by persons with dry skin. The lotion is spread over the skin, where it comes into contact with the coating of microorganisms normally covering the skin. These microorganisms quickly biodegrade D-glucitol, reducing the length of time over which the moisturizing product is effective, requiring more frequent applications. In this example, L-glucitol, the unnatural optical isomer, is used instead of D-glucitol. The skin microorganisms cannot appreciably biodegrade the L-glucitol, thereby permitting the moisturizer product to remain effective for a longer period of time.
In a related example, L-mannitol is used instead of D-mannitol based on the same concept, and producing the same result.
EXAMPLE 4 - Underarm Deodorant/Antiperspirant Deodorants operate by absorbing odors, reducing perspiration at the skin surface or masking malodors with other odors. Popular underarm deodorants consist of hard gels in the forms of sticks or bars which are applied under the arm where they leave a film of their material.
A paramount feature of such deodorants is the length of time the application retains its effectiveness. The underarm harbors many microorganisms which biodegrade the organic ingredients of the deodorant, thereby significantly reducing the lifetime of the product. A
widely used stick applicator deodorant/antiperspirant contains cobalt acetylmethionate as its principal active ingredient. Methionine is optically active. This example of the invention substitutes the unnatural optical isomer of methionine (D-methionine) for the natural isomer (L-methionine), thereby extending the lifetime of this key ingredient, and hence the effectiveness of the product.
EXAMPLE 5 - Sunblock Lotion Menthyl anthranilate is frequently used as the active ingredient in sunblock lotions applied to the body to prevent excessive sunburn by absorbing the ultraviolet rays of the sun. This compound is prepared from menthol by its esterification with anthranilic acid. The enantomeric form of the menthol used is carried into the product. Currently, the naturally occurring enantiomer of menthol (1-menthol) is used, or, in the case of synthetic menthol, the racemic mixture (1- and d-menthol in equal quantities) produced by the synthesis is used.
L-menthyl anthranilate, made from 1-menthol, is biodegradable. Skin bacteria biodegrade the 1-menthyl anthranilate, significantly shortening the lifetime of the sunblock lotion. In this example, the unnatural enantiomer of menthol (d-menthol) is used to make the menthyl anthranilate used in the sunblock lotion. Being lesser biodegradable, the d-menthyl anthranilate provides the sunblock lotion with a longer useful lifetime than does the normally used 1- or dl-menthyl anthranilate.
EXAMPLE 6 - Substitution of Lesser Biodegradable Compound with Same Functionality This example illustrates the broad application of this invention beyond the concept of using a lesser biodegradable isomer of a compound. In this case, a completely different compound, but with the same functionality and with lesser biodegradability, is substituted for the normally used compound. A widely used stick deodorant has aluminum zirconium tetrachlorohydrex glycine as its active ingredient. This compound is biodegradable. However, since glycine is not optically active, there is no enantiomeric, lesser biodegradable form of that amino acid to substitute for it. However, the function of the glycine is to neutralize the active ingredient in order to prevent or reduce its irritability to the skin of the user. Another amino acid, in this case alanine, will serve the same function if used in place of glycine. Alanine does have optical isomers L-alanine and D-alanine. According to the teachings of this invention, the lesser biodegradable enantiomer of alanine (D-alanine) is used to make aluminum zirconium tetrachlorohydrex alanine. This compound provides the deodorant product with the same functionality as did the aluminum zirconium tetrachlorohydrex glycine, but being less biodegradable, provides longer useful life for the product.
BIODEGRADATION OF A SUBSTANCE
Background of the Invention This invention relates to the extension of the useful lifetimes of biodegradable products by substituting lesser biodegradable ingredients having the same required functional characteristics such as odor. The practice of the invention relates to identifying such lesser biodegradable substances and substituting them, in existing or planned products, for those substances more subject to degradation.
Many substances lose functional lifetimes ?oecause of their vulnerability to microbial degradation. In a number of instances, substances with lesser biodegradability are substituted, such as polyvinyl for canvas, or fiberglass for wood. In these instances, the knowledge of the resistance of the selected substance to microbial decay is a factor in guiding the selection. Even though the immediate cost of the substitute is higher, the reduced biodegradability makes the substitution economical over the lifecycle of the product. There are, however, many instances in which there is no knowledge of longer lasting substitutes. These include instances in which other, perhaps initially more expensive, substances offer the same required functionality, but their greater resistance to biodegradation is unknown, as is, hence, their possible overall economic benefit. In other instances, in which unnatural optical isomers, stereoisomers, constitutional isomers, or other forms of the substances exist, useful lifetimes of the products can be extended by virtue of the relative nonbiodegradability of the unnatural or less common forms or substances. Lesser biodegradability is conferred by the fact that biodegrading bacteria, not having had long exposure to these substances, have not evolved the capability to metabolize them.
One aspect of this invention relates to a method for preventing or minimizing biodegradation of a substance which normally contains a naturally occurring optical isomer (or enantiomer, or optical stereoisomer). More particularly, this aspect of the invention relates to a process for rendering a fragrant substance, or surface, either bearing microorganisms or subject to deliberate or accidental contamination with microorganisms, odoriferous, e.g., fragrant, for an extended period of time.
Next to sight, the sense of smell is reported to be that sense most widely appreciated. It plays an important role in our everyday lives. For this reason, the fragrance industry has grown to its present enormous size. Commercially sold fragrances are based on natural products and synthetic ones. The latter have become of increasing importance as the science of chemistry has become more inventive. Natural fragrances have also been synthesized. However, many of the most pleasant, or otherwise desired odors are highly transient, requiring frequent re-applications, or disappearing after periods shorter than desired for the intended uses.
Fragrant or odoriferous preparations generally consist of two functional components: the odor-producing compound or material, and a vehicle which serves as a carrier for the fragrant molecules. Such vehicles have served their purpose when the fragrance has been adequately disseminated. These vehicles are generally short-chain organic compounds which then evaporate quite quickly. This leaves the generally longer-chain fragrant molecules in situ in the desired locations from which they, in turn, volatilize, although somewhat more slowly.
The sustained volatilization of these fragrant molecules achieves the desired effect by contacting the olfactories of the target persons or animals in the affected area.
While the fragrant compound applied to the site will ultimately be completely exhausted through volatilization, the full potential of this effective time is seldom, if ever, realized. This is because many fragrant molecules are biodegradable and they are generally applied to areas rich in microorganisms. An application is to skin, which is well known to be heavily laden with microorganisms. However, all other common surfaces are also heavily populated with microorganisms.
The interests of economy and personal appearance require that perfumes, for example, be applied sparingly. The biodegradability of the organic fragrance molecules results in the microbial populations attacking these molecules, metabolizing them and rendering the remains non-fragrant, less fragrant, or even of an undesirable odor. The otherwise expected useful time of the application of the product is thus effectively reduced.
In recent years, there has been a continuing replacement of natural fragrances with chemically synthesized molecules. Some are identical to natural fragrances, but are made synthetically more cheaply than can otherwise be obtained. Others are novel compounds, but these are also generally biodegradable. Both types of products suffer the same fate as described above for the natural fragrances.
Summary Of The Invention In the broadest aspect of this invention, there is provided a method for preventing or minimizing biodegradation of a substance which normally contains a biodegradable compound, which process comprises replacing the biodegradable compound with a corresponding lesser biodegradable compound providing the same desired functionality.
In accordance with one aspect of this invention, there is provided a method for preventing or minimizing biodegradation of a substance which normally contains a naturally occurring optical isomer, which process comprises replacing the naturally occurring optical isomer with the corresponding unnatural optical isomer.
Examples of such substances include fragrances, substances which contain fragrances, and nonfragrant substances which contain optical isomer(s), such as body lotions, soaps, deodorants, and dyes and paints.
In a preferred embodiment of this invention, there is provided a process for prolonging emanation of odors) from a substance or surface containing one or more odoriferous optically isomeric compounds and which substance or surface also contains or becomes contaminated with microorganisms, which process comprises selecting (an) unnatural optical isomers) of the compounds) to prevent or delay biodegradation of the odoriferous compound(s).
More generally, it has now been found that a functional substance or compound may retain the desired function for an extended period of time by substituting its non-naturally occurring optical stereoisomer, or an uncommon isomer or lesser biodegradable substance possessing the same functionality. The resulting substance will remain functional for a longer period of time than if the more naturally occurring form or the naturally occurring uncommon form or substance had been applied. This is because the non-naturally occurring form or the naturally occurring uncommon form or substance is non-biodegradable, or is of greatly reduced biodegradability since the microbial enzymes necessary to the biodegradation process can cope only with the more commonly occurring form or substance.
Detailed Description Of The Invention Some of the organic molecules synthesized for fragrance purposes, and some of the natural fragrance molecules which can be synthesized have structures which contain carbon atoms bonded to four different atomic groups. The four atomic groups can assume one of two opposite configurations about their central carbon atom.
For the purpose of chemical reactions, these configurations behave identically. Although little used as fragrances, amino acids and carbohydrates are -important examples of chirality, the occurrence of optical stereoisomers of the same molecule, and serve to illustrate the point. Virtually all amino acids in nature are of the optically stereoisomeric form designated "left handed", while natural carbohydrates occur almost exclusively in the optically stereoisomeric form called "right handed". (These common designations derive from their mirror images which demonstrate the chemical identity, and non-superimposability of the two forms of the same molecule.) The reason for the natural preference of one optical stereoisomer over its opposite form is unknown, but all known life forms follow this preference in their consumption and production of chiral organic compounds.
Some natural chemicals used in perfumery, and which have optical isomers, are listed in Table 1.
Table 1. Some Fragrances and their optical Isomers NATURAL OPTICAL ISOMER UNNATURAL OR LESS COMMON
NATURAL OPTICAL ISOMER
(1R, 2S, 5R) - (-) -Menthol (1S, 2R, 5S) - (+) -Menthol (R)-(+)-Citronellal (S)-(-)-Citronellal (+)-Limonene (-)-Limonene (-)-Menthone Three stereoisomers (1R)-(-)-Menthyl Acetate (1S)-(+)-Menthyl Acetate The strong preference, or specificity, for natural optical isomers displayed by biological entities is because virtually all biological reactions are conducted _ g _ through the participation of enzymes. From the time life originated, its first enzymes have consistently passed on their optical isomeric specificity to all life forms evolved down through the eons. Enzymes, being templates which position molecules for specific reactions, do distinguish between optical isomers of the same molecule.
Not being able to fit physically to the other optical isomer of the reactive molecular species, an enzyme cannot induce the reaction with the unnatural optical isomer.
The sense of smell has been attributed to enzymatic reactions: "Olfactory transduction begins with the binding of an odorant ligand to a protein receptor of the olfactory neuron cell surface, initiating a cascade of enzymatic reactions... "(Breer, H., Semin. Cell Bio1 5, 25, 1994; Sheppard, G.M., Neuron 13, 771, 1994, cited by Zhao, H. et a1, Science, 279, 237, 1998). A fundamental characteristic of enzymatic reactions is their specificity for the molecule they catalyze into reaction.
"Perhaps the most striking aspect of the specificity of enzymes is their ability to select between enantiomorphous compounds. This may be termed stereochemical specificity. For example, carboxypeptidase, which catalyzes the hydrolysis of carbobenzoxyglycyl-L-phenalalanine, has no measurable action on carbobenzoxyglycyl-D-phenalalanine. ...These examples of stereochemical specificity involve an absolute discrimination between enantiomorphs." (General Biochemistry, Fruton and Simmonds, eds, 3rd printing, p.
277, John Wiley & Sons, Inc., NY, 1960). A number of fragrant or odoriferous compounds are natural optical isomers. It would be expected that the unnatural enantiomers of these compounds would not trigger the sense of smell, because their molecules would not fit the protein (enzyme) receptor encountered. Since the enzyme receptors have evolved to fit with natural products only, the unnatural optical isomer would not fit, and, therefore, no odor-sensing reaction would be expected to occur with the neuron. However, the inventors have found that both the naturally occurring optical stereoisomer and the non-naturally occurring optical stereoisomer have the same odor, which demonstrates the core of this invention.
The odoriferous compounds used in the practice of the fragrance-prolonging aspect of this invention may be used in perfumes, eau de colognes, powders, mouth washes, dentifrices, confections, deodorants for personal and area uses, douches, hair applications, simulated odors for various products (such as leather odors for plastic upholstery), tobacco products, insect and animal repellants and attractants, and the wide variety of other products and uses for fragrances, masking odors, artificial odors, or other scents including those used in foodstuffs, beverages and the like.
EXAMPLE 1 - Menthol as a Fragrance The naturally-occurring optical isomer of menthol (1R,2S,5R)-(-) is used as a fragrance in a variety of products, such as perfumes, gums, and cigarettes. Both the natural and the unnatural (1S,2R,5S)-(+) optical isomer of menthol were obtained in 99o purity. A O.OO1M
solution of each enantiomer was prepared in reagent grade acetone. The solutions were allowed to equilibrate at room temperature for approximately one hour. Twenty drops of each solution were pipetted into separate glass Petri dishes. All glassware was clean. The acetone was then allowed to evaporate at room temperature. Human subjects then smelled the two Petri dishes separately and recorded any sensations. The subjects had been instructed to determine the presence of odor in the Petri dishes, and, if odor emanated from each, to determine whether the odors were the same or different. The test was performed twice on each of six human subjects, three female and three male. Each subject was given freshly prepared Petri dish servings to smell, and each immediately recorded his or her impressions without communicating with the other subjects.
All six subjects found that the unnatural form of menthol had odor. Moreover, all six found the odor of the unnatural form to be the same as that of the natural form. These results constitute evidence that the sense of smell is not enzymatic as heretofore believed by the scientific community. This unexpected finding constitutes the essential basis of the innovation claimed herein.
EXAMPLE 2 - Odor Absorber/Deodorant Objectionable odors may be absorbed by a variety of chemicals. Such chemicals may be added to an odoriferous material, or sprayed onto surfaces. This example relates to the use of zinc glutamate as an odor absorber. Zinc glutamate is normally used in the form of zinc salt of L-glutamic acid for this purpose. However, this form of the compound is readily biodegraded by microorganisms that are generally abundant in the treatment area. In this embodiment of the invention, the zinc salt of D-glutamic acid is substituted for the normal form, with the result that the odor-absorbing material, and, hence, odor removal function, lasts considerably longer than when the natural form of zinc glutamate is used.
Other chemicals with the deodorant function include zinc gluconate and sodium aluminum chlorohydroxy lactate.
D-gluconic acid and D-lactic acid are natural products, which are readily biodegradable. The use of their unnatural optical isomers, the zinc salt of L-gluconic acid and the sodium aluminum salt of L-lactic acid, instead of the natural products will result in the odor absorbing material lasting considerably longer.
EXAMPLE 3 - Humectant Besides their application in food, pharmaceutical and other industries, D-glucitol (i.e., sorbitol) and D-mannitol, the naturally occurring sugar alcohol, are commonly used as humectants (water-attracting/binding) as well as emollient ingredients in many cosmetic products, for example, in body lotions and sunblock. A
moisturizing lotion, in which D-glucitol is provided as a humectant and emollient, is applied to the skin daily or twice daily, especially by persons with dry skin. The lotion is spread over the skin, where it comes into contact with the coating of microorganisms normally covering the skin. These microorganisms quickly biodegrade D-glucitol, reducing the length of time over which the moisturizing product is effective, requiring more frequent applications. In this example, L-glucitol, the unnatural optical isomer, is used instead of D-glucitol. The skin microorganisms cannot appreciably biodegrade the L-glucitol, thereby permitting the moisturizer product to remain effective for a longer period of time.
In a related example, L-mannitol is used instead of D-mannitol based on the same concept, and producing the same result.
EXAMPLE 4 - Underarm Deodorant/Antiperspirant Deodorants operate by absorbing odors, reducing perspiration at the skin surface or masking malodors with other odors. Popular underarm deodorants consist of hard gels in the forms of sticks or bars which are applied under the arm where they leave a film of their material.
A paramount feature of such deodorants is the length of time the application retains its effectiveness. The underarm harbors many microorganisms which biodegrade the organic ingredients of the deodorant, thereby significantly reducing the lifetime of the product. A
widely used stick applicator deodorant/antiperspirant contains cobalt acetylmethionate as its principal active ingredient. Methionine is optically active. This example of the invention substitutes the unnatural optical isomer of methionine (D-methionine) for the natural isomer (L-methionine), thereby extending the lifetime of this key ingredient, and hence the effectiveness of the product.
EXAMPLE 5 - Sunblock Lotion Menthyl anthranilate is frequently used as the active ingredient in sunblock lotions applied to the body to prevent excessive sunburn by absorbing the ultraviolet rays of the sun. This compound is prepared from menthol by its esterification with anthranilic acid. The enantomeric form of the menthol used is carried into the product. Currently, the naturally occurring enantiomer of menthol (1-menthol) is used, or, in the case of synthetic menthol, the racemic mixture (1- and d-menthol in equal quantities) produced by the synthesis is used.
L-menthyl anthranilate, made from 1-menthol, is biodegradable. Skin bacteria biodegrade the 1-menthyl anthranilate, significantly shortening the lifetime of the sunblock lotion. In this example, the unnatural enantiomer of menthol (d-menthol) is used to make the menthyl anthranilate used in the sunblock lotion. Being lesser biodegradable, the d-menthyl anthranilate provides the sunblock lotion with a longer useful lifetime than does the normally used 1- or dl-menthyl anthranilate.
EXAMPLE 6 - Substitution of Lesser Biodegradable Compound with Same Functionality This example illustrates the broad application of this invention beyond the concept of using a lesser biodegradable isomer of a compound. In this case, a completely different compound, but with the same functionality and with lesser biodegradability, is substituted for the normally used compound. A widely used stick deodorant has aluminum zirconium tetrachlorohydrex glycine as its active ingredient. This compound is biodegradable. However, since glycine is not optically active, there is no enantiomeric, lesser biodegradable form of that amino acid to substitute for it. However, the function of the glycine is to neutralize the active ingredient in order to prevent or reduce its irritability to the skin of the user. Another amino acid, in this case alanine, will serve the same function if used in place of glycine. Alanine does have optical isomers L-alanine and D-alanine. According to the teachings of this invention, the lesser biodegradable enantiomer of alanine (D-alanine) is used to make aluminum zirconium tetrachlorohydrex alanine. This compound provides the deodorant product with the same functionality as did the aluminum zirconium tetrachlorohydrex glycine, but being less biodegradable, provides longer useful life for the product.
Claims (34)
1. A method for preventing or minimizing biodegradation of a substance which normally contains a biodegradable compound which comprises replacing the compound with a corresponding lesser biodegradable compound providing the same desired functionality.
2. A method according to claim 1 wherein said compound is an odor absorber and/or a deodorant.
3. A method according to claim 2 wherein the zinc salt of L-glutamic acid is replaced with the zinc salt of D-glutamic acid.
4. A method according to claim 2 wherein the zinc salt of D-gluconic acid is replaced with the zinc salt of L-gluconic acid.
5. A method according to claim 2 wherein the sodium aluminum salt of D-lactic acid is replaced with the sodium aluminum salt of L-lactic acid.
6. A method according to claim 1 wherein said compound is a humectant.
7. A method according to claim 6 wherein D-glucitol is replaced with L-glucitol.
8. A method according to claim 6 wherein D-mannitol is replaced with L-mannitol.
9. A method according to claim 1 wherein said compound is an underarm deodorant and/or antiperspirant.
10. A method according to claim 9 wherein cobalt acetylmethionate (L-methionine) is replaced with cobalt acetylmethionate (D-methionine).
11. A method according to claim 9 wherein aluminum zirconium tetrachlorohydrex glycine is replaced with aluminum zirconium tetrachlorohydrex complex with any unnatural amino acid (D-amino acid), such as D-alanine.
12. A method according to claim 1 wherein said compound is a sun block agent.
13. A method according to claim 12 wherein 1- or dl-menthyl anthranilate is replaced with d-menthyl anthranilate.
14. A method according to claim 1 wherein the compound being replaced is replaced with a lesser biodegradable compound which is not an isomer of the biodegradable compound which is being replaced.
15. A method according to claim 14 wherein aluminum zirconium tetrachlorohydrex glycine in a deodorant is replaced with aluminum zirconium tetrachlorohydrex D-alanine.
16. A method for preventing or minimizing biodegradation of a substance which normally contains a naturally occurring optical isomer which comprises replacing the naturally occurring optical isomer with the corresponding unnatural optical isomer.
17. A process for prolonging emanation of odor from a substance or surface containing one or more odoriferous optically isomeric compounds which process comprises selecting an unnatural optical isomer of the compound(s) for use in or on the substance or surface to prevent or delay biodegradation of the fragrance by microorganisms present on, or accidentally or deliberately contacting the substance or surface.
18. A process for rendering a substance or surface odoriferous for an extended period of time which comprises selecting an odoriferous compound which can exist in the form of optical stereoisomers, one being naturally occurring and the other being non-naturally occurring and applying to said substance or surface said non-naturally occurring optical stereoisomer to prevent or delay biodegradation of the odoriferous compound.
19. A process according to claim 18 wherein said surface is human skin, hair or mucosal tissue.
20. A process according to claim 18 wherein said odoriferous compound is a fragrance.
21. A process according to claim 18 in which the substance incorporating the odoriferous compound are selected from the group consisting of perfumes, eau de colognes, powders, mouth washes, dentrifices, confections, deodorants for personal and area uses, incenses, candles, shaving creams and lotions, body lotions, shampoos, laundry and dry cleaning products, dish cleansers, furniture and leather treatments, douches, hair applications, simulated odors for various products (such as leather odors for plastic upholstery), tobacco products, household and personal cleansers, insect and animal repellents and attractants, foodstuffs, and alcoholic and non-alcoholic beverages.
22. A process according to claim 18 wherein said odoriferous compound is (1S,2R,5S)-(+)-menthol.
23. A process according to claim 18 wherein said odoriferous compound is (S)-(-)-citronellal.
24. A process according to claim 18 wherein said odoriferous compound is (+)-linalool.
25. A process according to claim 18 wherein said odoriferous compound is (1S)-(+)-methyl acetate.
26. An odoriferous product obtained by the process of claim 17.
27. An odoriferous product obtained by the process of claim 18.
28. An odoriferous product obtained by the process of claim 19.
29. An odoriferous product obtained by the process of claim 20.
30. An odoriferous product obtained by the process of claim 21.
31. An odoriferous product obtained by the process of claim 22.
32. An odoriferous product obtained by the process of claim 23.
33. An odoriferous product obtained by the process of claim 24.
34. An odoriferous product obtained by the process of claim 25.
Applications Claiming Priority (5)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
US09/305,739 | 1999-05-06 | ||
US09/305,739 US6585964B1 (en) | 1999-05-06 | 1999-05-06 | Method for preventing or minimizing biodegradation of a substance |
US44144099A | 1999-11-17 | 1999-11-17 | |
US09/441,440 | 1999-11-17 | ||
PCT/US2000/008881 WO2000068369A1 (en) | 1999-05-06 | 2000-04-04 | Method for preventing or minimizing biodegradation of a substance |
Publications (1)
Publication Number | Publication Date |
---|---|
CA2372612A1 true CA2372612A1 (en) | 2000-11-16 |
Family
ID=26974757
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
CA002372612A Abandoned CA2372612A1 (en) | 1999-05-06 | 2000-04-04 | Method for preventing or minimizing biodegradation of a substance |
Country Status (5)
Country | Link |
---|---|
EP (1) | EP1173558A4 (en) |
JP (1) | JP2003519246A (en) |
AU (1) | AU4068400A (en) |
CA (1) | CA2372612A1 (en) |
WO (1) | WO2000068369A1 (en) |
Families Citing this family (7)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US7326409B2 (en) | 2003-12-12 | 2008-02-05 | L'oreal S.A. | Deodorant cosmetic composition comprising a combination of zinc pidolate and an antiperspirant aluminum salt |
FR2863488B1 (en) * | 2003-12-12 | 2006-05-12 | Oreal | COSMETIC DEODORANT COMPOSITION COMPRISING THE ASSOCIATION OF ZINC GLUCONATE AND A SINGLE ANTI-TRANSPIRANT ALUMINUM SALT |
FR2863489B1 (en) * | 2003-12-12 | 2006-05-12 | Oreal | COSMETIC DEODORANT COMPOSITION COMPRISING THE ASSOCIATION OF ZINC PIDOLATE AND ANTI-TRANPIRANT ALUMINUM SALT |
US7332154B2 (en) | 2003-12-12 | 2008-02-19 | L'oreal S.A. | Deodorant cosmetic composition comprising a combination of zinc gluconate and an antiperspirant aluminum salt |
JP2011256137A (en) * | 2010-06-09 | 2011-12-22 | Shiseido Co Ltd | Agent suppressing decrease in preservative ability in amino acid-containing composition |
JP6639767B2 (en) * | 2013-10-07 | 2020-02-05 | 小林製薬株式会社 | Deodorizing device and deodorizing method |
JP7011894B2 (en) * | 2017-02-10 | 2022-02-10 | アサヒビール株式会社 | Alcoholic beverages and their manufacturing methods |
Family Cites Families (7)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
JPS57158724A (en) * | 1981-03-26 | 1982-09-30 | Shiseido Co Ltd | Antimicrobial composition |
JPH0728213A (en) * | 1993-05-14 | 1995-01-31 | Konica Corp | Solid processing agent for silver halide color photographic sensitive material |
JPH092999A (en) * | 1995-06-16 | 1997-01-07 | Taki Chem Co Ltd | Production of aluminum lactate crystal |
JP3528072B2 (en) * | 1995-10-13 | 2004-05-17 | 高砂香料工業株式会社 | Fragrance composition containing (4R) -cis-4-methyl-2-substituted tetrahydro-2H-pyran derivative and method for improving fragrance using (4R) -cis-4-methyl-2-substituted tetrahydro-2H-pyran derivative |
EP0884045A1 (en) * | 1997-06-06 | 1998-12-16 | Pfizer Products Inc. | Self-tanning dihydroxyacetone formulations having improved stability and providing enhanced delivery |
US5902572A (en) * | 1997-06-23 | 1999-05-11 | Procter & Gamble Company | Anhydrous gel deodorant compositions |
GB9715751D0 (en) * | 1997-07-26 | 1997-10-01 | Ciba Geigy Ag | Formulations |
-
2000
- 2000-04-04 CA CA002372612A patent/CA2372612A1/en not_active Abandoned
- 2000-04-04 AU AU40684/00A patent/AU4068400A/en not_active Abandoned
- 2000-04-04 WO PCT/US2000/008881 patent/WO2000068369A1/en active Application Filing
- 2000-04-04 EP EP00920094A patent/EP1173558A4/en not_active Withdrawn
- 2000-04-04 JP JP2000616336A patent/JP2003519246A/en active Pending
Also Published As
Publication number | Publication date |
---|---|
EP1173558A1 (en) | 2002-01-23 |
EP1173558A4 (en) | 2002-07-24 |
JP2003519246A (en) | 2003-06-17 |
WO2000068369A1 (en) | 2000-11-16 |
AU4068400A (en) | 2000-11-21 |
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EEER | Examination request | ||
FZDE | Discontinued |