EP1581058A4 - Method and composition for the prevention of the auto-oxidation of flavors and fragrances - Google Patents
Method and composition for the prevention of the auto-oxidation of flavors and fragrancesInfo
- Publication number
- EP1581058A4 EP1581058A4 EP02773846A EP02773846A EP1581058A4 EP 1581058 A4 EP1581058 A4 EP 1581058A4 EP 02773846 A EP02773846 A EP 02773846A EP 02773846 A EP02773846 A EP 02773846A EP 1581058 A4 EP1581058 A4 EP 1581058A4
- Authority
- EP
- European Patent Office
- Prior art keywords
- acetate
- oil
- fragrance
- butyl
- tert
- 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.)
- Withdrawn
Links
- 239000000203 mixture Substances 0.000 title claims abstract description 73
- 239000003205 fragrance Substances 0.000 title claims abstract description 54
- 239000000796 flavoring agent Substances 0.000 title claims abstract description 52
- 235000019634 flavors Nutrition 0.000 title claims abstract description 35
- 238000007254 oxidation reaction Methods 0.000 title claims abstract description 20
- 238000000034 method Methods 0.000 title claims description 24
- 230000002265 prevention Effects 0.000 title description 2
- 239000003963 antioxidant agent Substances 0.000 claims abstract description 39
- 230000003078 antioxidant effect Effects 0.000 claims abstract description 32
- 150000001875 compounds Chemical class 0.000 claims abstract description 21
- 235000006708 antioxidants Nutrition 0.000 claims description 38
- -1 carnasol Natural products 0.000 claims description 12
- DOUMFZQKYFQNTF-WUTVXBCWSA-N (R)-rosmarinic acid Chemical compound C([C@H](C(=O)O)OC(=O)\C=C\C=1C=C(O)C(O)=CC=1)C1=CC=C(O)C(O)=C1 DOUMFZQKYFQNTF-WUTVXBCWSA-N 0.000 claims description 10
- 241000207923 Lamiaceae Species 0.000 claims description 10
- 238000004519 manufacturing process Methods 0.000 claims description 10
- 150000002978 peroxides Chemical class 0.000 claims description 10
- 235000019502 Orange oil Nutrition 0.000 claims description 9
- 239000004615 ingredient Substances 0.000 claims description 9
- 239000010502 orange oil Substances 0.000 claims description 9
- QRYRORQUOLYVBU-VBKZILBWSA-N carnosic acid Chemical group CC([C@@H]1CC2)(C)CCC[C@]1(C(O)=O)C1=C2C=C(C(C)C)C(O)=C1O QRYRORQUOLYVBU-VBKZILBWSA-N 0.000 claims description 8
- 235000013305 food Nutrition 0.000 claims description 8
- 229940092258 rosemary extract Drugs 0.000 claims description 7
- 235000020748 rosemary extract Nutrition 0.000 claims description 7
- 239000001233 rosmarinus officinalis l. extract Substances 0.000 claims description 7
- 230000015572 biosynthetic process Effects 0.000 claims description 6
- 239000000284 extract Substances 0.000 claims description 6
- JBWRHBJFAVSAMJ-VBKZILBWSA-N Rosmadial Chemical compound OC=1C(C(C)C)=CC(C=O)=C2C=1OC(=O)[C@@]21CCCC(C)(C)[C@@H]1C=O JBWRHBJFAVSAMJ-VBKZILBWSA-N 0.000 claims description 5
- CEEMRWKKNNEQDT-UHFFFAOYSA-N Rosmanol Natural products CC(C)c1cc2C(OC(=O)C)C3OC(=O)C4(CCCC(C)(C)C34)c2c(OC(=O)C)c1OC(=O)C CEEMRWKKNNEQDT-UHFFFAOYSA-N 0.000 claims description 5
- ZZAFFYPNLYCDEP-HNNXBMFYSA-N Rosmarinsaeure Natural products OC(=O)[C@H](Cc1cccc(O)c1O)OC(=O)C=Cc2ccc(O)c(O)c2 ZZAFFYPNLYCDEP-HNNXBMFYSA-N 0.000 claims description 5
- 235000011194 food seasoning agent Nutrition 0.000 claims description 5
- DOUMFZQKYFQNTF-MRXNPFEDSA-N rosemarinic acid Natural products C([C@H](C(=O)O)OC(=O)C=CC=1C=C(O)C(O)=CC=1)C1=CC=C(O)C(O)=C1 DOUMFZQKYFQNTF-MRXNPFEDSA-N 0.000 claims description 5
- HYGRYNBYOVHMAO-UHFFFAOYSA-N rosmadial Natural products CC(C)c1cc(C=O)c2C3C(CCC(C)(C)C3C=O)C(=O)Oc2c1O HYGRYNBYOVHMAO-UHFFFAOYSA-N 0.000 claims description 5
- LCAZOMIGFDQMNC-FORWCCJISA-N rosmanol Chemical compound C1CCC(C)(C)[C@@H]2[C@H]3[C@@H](O)C(C=C(C(=C4O)O)C(C)C)=C4[C@]21C(=O)O3 LCAZOMIGFDQMNC-FORWCCJISA-N 0.000 claims description 5
- TVHVQJFBWRLYOD-UHFFFAOYSA-N rosmarinic acid Natural products OC(=O)C(Cc1ccc(O)c(O)c1)OC(=Cc2ccc(O)c(O)c2)C=O TVHVQJFBWRLYOD-UHFFFAOYSA-N 0.000 claims description 5
- 239000002537 cosmetic Substances 0.000 claims description 4
- 230000003647 oxidation Effects 0.000 claims description 4
- 230000000087 stabilizing effect Effects 0.000 claims description 4
- 235000013372 meat Nutrition 0.000 claims description 3
- HRHOWZHRCRZVCU-AATRIKPKSA-N (E)-hex-2-enyl acetate Chemical compound CCC\C=C\COC(C)=O HRHOWZHRCRZVCU-AATRIKPKSA-N 0.000 claims 8
- SVTBMSDMJJWYQN-UHFFFAOYSA-N 2-methylpentane-2,4-diol Chemical compound CC(O)CC(C)(C)O SVTBMSDMJJWYQN-UHFFFAOYSA-N 0.000 claims 8
- WRMNZCZEMHIOCP-UHFFFAOYSA-N 2-phenylethanol Chemical compound OCCC1=CC=CC=C1 WRMNZCZEMHIOCP-UHFFFAOYSA-N 0.000 claims 8
- BGTBFNDXYDYBEY-FNORWQNLSA-N 4-(2,6,6-Trimethylcyclohex-1-enyl)but-2-en-4-one Chemical compound C\C=C\C(=O)C1=C(C)CCCC1(C)C BGTBFNDXYDYBEY-FNORWQNLSA-N 0.000 claims 8
- JUWUWIGZUVEFQB-UHFFFAOYSA-N Fenchyl acetate Chemical compound C1CC2C(C)(C)C(OC(=O)C)C1(C)C2 JUWUWIGZUVEFQB-UHFFFAOYSA-N 0.000 claims 8
- QUMXDOLUJCHOAY-UHFFFAOYSA-N alpha-methylbenzyl acetate Natural products CC(=O)OC(C)C1=CC=CC=C1 QUMXDOLUJCHOAY-UHFFFAOYSA-N 0.000 claims 8
- HUMNYLRZRPPJDN-UHFFFAOYSA-N benzaldehyde Chemical compound O=CC1=CC=CC=C1 HUMNYLRZRPPJDN-UHFFFAOYSA-N 0.000 claims 8
- NEHNMFOYXAPHSD-UHFFFAOYSA-N citronellal Chemical compound O=CCC(C)CCC=C(C)C NEHNMFOYXAPHSD-UHFFFAOYSA-N 0.000 claims 8
- QMVPMAAFGQKVCJ-UHFFFAOYSA-N citronellol Chemical compound OCCC(C)CCC=C(C)C QMVPMAAFGQKVCJ-UHFFFAOYSA-N 0.000 claims 8
- SHZIWNPUGXLXDT-UHFFFAOYSA-N ethyl hexanoate Chemical compound CCCCCC(=O)OCC SHZIWNPUGXLXDT-UHFFFAOYSA-N 0.000 claims 8
- ZSIAUFGUXNUGDI-UHFFFAOYSA-N hexan-1-ol Chemical compound CCCCCCO ZSIAUFGUXNUGDI-UHFFFAOYSA-N 0.000 claims 8
- AOGQPLXWSUTHQB-UHFFFAOYSA-N hexyl acetate Chemical compound CCCCCCOC(C)=O AOGQPLXWSUTHQB-UHFFFAOYSA-N 0.000 claims 8
- MLFHJEHSLIIPHL-UHFFFAOYSA-N isoamyl acetate Chemical compound CC(C)CCOC(C)=O MLFHJEHSLIIPHL-UHFFFAOYSA-N 0.000 claims 8
- PHTQWCKDNZKARW-UHFFFAOYSA-N isoamylol Chemical compound CC(C)CCO PHTQWCKDNZKARW-UHFFFAOYSA-N 0.000 claims 8
- XMGQYMWWDOXHJM-UHFFFAOYSA-N limonene Chemical compound CC(=C)C1CCC(C)=CC1 XMGQYMWWDOXHJM-UHFFFAOYSA-N 0.000 claims 8
- OSWPMRLSEDHDFF-UHFFFAOYSA-N methyl salicylate Chemical compound COC(=O)C1=CC=CC=C1O OSWPMRLSEDHDFF-UHFFFAOYSA-N 0.000 claims 8
- NUJGJRNETVAIRJ-UHFFFAOYSA-N octanal Chemical compound CCCCCCCC=O NUJGJRNETVAIRJ-UHFFFAOYSA-N 0.000 claims 8
- HFPZCAJZSCWRBC-UHFFFAOYSA-N p-cymene Chemical compound CC(C)C1=CC=C(C)C=C1 HFPZCAJZSCWRBC-UHFFFAOYSA-N 0.000 claims 8
- MDHYEMXUFSJLGV-UHFFFAOYSA-N phenethyl acetate Chemical compound CC(=O)OCCC1=CC=CC=C1 MDHYEMXUFSJLGV-UHFFFAOYSA-N 0.000 claims 8
- DTGKSKDOIYIVQL-WEDXCCLWSA-N (+)-borneol Chemical compound C1C[C@@]2(C)[C@@H](O)C[C@@H]1C2(C)C DTGKSKDOIYIVQL-WEDXCCLWSA-N 0.000 claims 4
- NOOLISFMXDJSKH-KXUCPTDWSA-N (-)-Menthol Chemical compound CC(C)[C@@H]1CC[C@@H](C)C[C@H]1O NOOLISFMXDJSKH-KXUCPTDWSA-N 0.000 claims 4
- 229930006727 (-)-endo-fenchol Natural products 0.000 claims 4
- REPVLJRCJUVQFA-UHFFFAOYSA-N (-)-isopinocampheol Natural products C1C(O)C(C)C2C(C)(C)C1C2 REPVLJRCJUVQFA-UHFFFAOYSA-N 0.000 claims 4
- 239000001563 (1,5,5-trimethyl-6-bicyclo[2.2.1]heptanyl) acetate Substances 0.000 claims 4
- KJPRLNWUNMBNBZ-QPJJXVBHSA-N (E)-cinnamaldehyde Chemical compound O=C\C=C\C1=CC=CC=C1 KJPRLNWUNMBNBZ-QPJJXVBHSA-N 0.000 claims 4
- OOCCDEMITAIZTP-QPJJXVBHSA-N (E)-cinnamyl alcohol Chemical compound OC\C=C\C1=CC=CC=C1 OOCCDEMITAIZTP-QPJJXVBHSA-N 0.000 claims 4
- QMVPMAAFGQKVCJ-SNVBAGLBSA-N (R)-(+)-citronellol Natural products OCC[C@H](C)CCC=C(C)C QMVPMAAFGQKVCJ-SNVBAGLBSA-N 0.000 claims 4
- DSSYKIVIOFKYAU-XCBNKYQSSA-N (R)-camphor Chemical compound C1C[C@@]2(C)C(=O)C[C@@H]1C2(C)C DSSYKIVIOFKYAU-XCBNKYQSSA-N 0.000 claims 4
- XEJGJTYRUWUFFD-FNORWQNLSA-N (e)-1-(2,6,6-trimethyl-1-cyclohex-3-enyl)but-2-en-1-one Chemical compound C\C=C\C(=O)C1C(C)C=CCC1(C)C XEJGJTYRUWUFFD-FNORWQNLSA-N 0.000 claims 4
- XEJGJTYRUWUFFD-UHFFFAOYSA-N 1-(2,6,6-trimethylcyclohex-3-en-1-yl)but-2-en-1-one Chemical compound CC=CC(=O)C1C(C)C=CCC1(C)C XEJGJTYRUWUFFD-UHFFFAOYSA-N 0.000 claims 4
- PARHMNZPOUVEIQ-UHFFFAOYSA-N 1-(4-hydroxyphenyl)butan-2-one Chemical compound CCC(=O)CC1=CC=C(O)C=C1 PARHMNZPOUVEIQ-UHFFFAOYSA-N 0.000 claims 4
- WNJSKZBEWNVKGU-UHFFFAOYSA-N 2,2-dimethoxyethylbenzene Chemical compound COC(OC)CC1=CC=CC=C1 WNJSKZBEWNVKGU-UHFFFAOYSA-N 0.000 claims 4
- BHQBQWOZHYUVTL-UHFFFAOYSA-N 2-(3-methylbutoxy)ethylbenzene Chemical compound CC(C)CCOCCC1=CC=CC=C1 BHQBQWOZHYUVTL-UHFFFAOYSA-N 0.000 claims 4
- FLUWAIIVLCVEKF-UHFFFAOYSA-N 2-Methyl-1-phenyl-2-propanyl acetate Chemical compound CC(=O)OC(C)(C)CC1=CC=CC=C1 FLUWAIIVLCVEKF-UHFFFAOYSA-N 0.000 claims 4
- HSTMKGFYRGMMOF-UHFFFAOYSA-N 2-butan-2-ylcyclohexan-1-ol Chemical compound CCC(C)C1CCCCC1O HSTMKGFYRGMMOF-UHFFFAOYSA-N 0.000 claims 4
- RIWRBSMFKVOJMN-UHFFFAOYSA-N 2-methyl-1-phenylpropan-2-ol Chemical compound CC(C)(O)CC1=CC=CC=C1 RIWRBSMFKVOJMN-UHFFFAOYSA-N 0.000 claims 4
- FGZXHVORLPLICA-UHFFFAOYSA-N 2-methylundecan-1-ol Chemical compound CCCCCCCCCC(C)CO FGZXHVORLPLICA-UHFFFAOYSA-N 0.000 claims 4
- NFAVNWJJYQAGNB-UHFFFAOYSA-N 2-methylundecanal Chemical compound CCCCCCCCCC(C)C=O NFAVNWJJYQAGNB-UHFFFAOYSA-N 0.000 claims 4
- VNWOJVJCRAHBJJ-UHFFFAOYSA-N 2-pentylcyclopentan-1-one Chemical compound CCCCCC1CCCC1=O VNWOJVJCRAHBJJ-UHFFFAOYSA-N 0.000 claims 4
- DLTWBMHADAJAAZ-UHFFFAOYSA-N 2-tert-butylcyclohexan-1-ol Chemical compound CC(C)(C)C1CCCCC1O DLTWBMHADAJAAZ-UHFFFAOYSA-N 0.000 claims 4
- ZRYDPLOWJSFQAE-UHFFFAOYSA-N 2-tert-butylcyclohexan-1-one Chemical compound CC(C)(C)C1CCCCC1=O ZRYDPLOWJSFQAE-UHFFFAOYSA-N 0.000 claims 4
- BJLRAKFWOUAROE-UHFFFAOYSA-N 2500-83-6 Chemical compound C12C=CCC2C2CC(OC(=O)C)C1C2 BJLRAKFWOUAROE-UHFFFAOYSA-N 0.000 claims 4
- HRXNWQMMTLLJJQ-UHFFFAOYSA-N 3,3,5-trimethylhexan-1-ol Chemical compound CC(C)CC(C)(C)CCO HRXNWQMMTLLJJQ-UHFFFAOYSA-N 0.000 claims 4
- DLHQZZUEERVIGQ-UHFFFAOYSA-N 3,7-dimethyl-3-octanol Chemical compound CCC(C)(O)CCCC(C)C DLHQZZUEERVIGQ-UHFFFAOYSA-N 0.000 claims 4
- GOLORTLGFDVFDW-UHFFFAOYSA-N 3-(1h-benzimidazol-2-yl)-7-(diethylamino)chromen-2-one Chemical compound C1=CC=C2NC(C3=CC4=CC=C(C=C4OC3=O)N(CC)CC)=NC2=C1 GOLORTLGFDVFDW-UHFFFAOYSA-N 0.000 claims 4
- OXYRENDGHPGWKV-UHFFFAOYSA-N 3-methyl-5-phenylpentan-1-ol Chemical compound OCCC(C)CCC1=CC=CC=C1 OXYRENDGHPGWKV-UHFFFAOYSA-N 0.000 claims 4
- MBZRJSQZCBXRGK-UHFFFAOYSA-N 4-tert-Butylcyclohexyl acetate Chemical compound CC(=O)OC1CCC(C(C)(C)C)CC1 MBZRJSQZCBXRGK-UHFFFAOYSA-N 0.000 claims 4
- CCOQPGVQAWPUPE-UHFFFAOYSA-N 4-tert-butylcyclohexan-1-ol Chemical compound CC(C)(C)C1CCC(O)CC1 CCOQPGVQAWPUPE-UHFFFAOYSA-N 0.000 claims 4
- WWJLCYHYLZZXBE-UHFFFAOYSA-N 5-chloro-1,3-dihydroindol-2-one Chemical compound ClC1=CC=C2NC(=O)CC2=C1 WWJLCYHYLZZXBE-UHFFFAOYSA-N 0.000 claims 4
- LJSJTXAZFHYHMM-UHFFFAOYSA-N 7-methyloctyl acetate Chemical compound CC(C)CCCCCCOC(C)=O LJSJTXAZFHYHMM-UHFFFAOYSA-N 0.000 claims 4
- RVOKNSFEAOYULQ-UHFFFAOYSA-N 8-Mercapto-p-menthan-3-one Chemical compound CC1CCC(C(C)(C)S)C(=O)C1 RVOKNSFEAOYULQ-UHFFFAOYSA-N 0.000 claims 4
- QTBSBXVTEAMEQO-UHFFFAOYSA-M Acetate Chemical compound CC([O-])=O QTBSBXVTEAMEQO-UHFFFAOYSA-M 0.000 claims 4
- WTEVQBCEXWBHNA-UHFFFAOYSA-N Citral Natural products CC(C)=CCCC(C)=CC=O WTEVQBCEXWBHNA-UHFFFAOYSA-N 0.000 claims 4
- KBEBGUQPQBELIU-CMDGGOBGSA-N Ethyl cinnamate Chemical compound CCOC(=O)\C=C\C1=CC=CC=C1 KBEBGUQPQBELIU-CMDGGOBGSA-N 0.000 claims 4
- XRHCAGNSDHCHFJ-UHFFFAOYSA-N Ethylene brassylate Chemical compound O=C1CCCCCCCCCCCC(=O)OCCO1 XRHCAGNSDHCHFJ-UHFFFAOYSA-N 0.000 claims 4
- IAIHUHQCLTYTSF-MRTMQBJTSA-N Fenchyl alcohol Chemical compound C1C[C@]2(C)[C@H](O)C(C)(C)[C@H]1C2 IAIHUHQCLTYTSF-MRTMQBJTSA-N 0.000 claims 4
- DUKPKQFHJQGTGU-UHFFFAOYSA-N Hexyl salicylic acid Chemical compound CCCCCCOC(=O)C1=CC=CC=C1O DUKPKQFHJQGTGU-UHFFFAOYSA-N 0.000 claims 4
- KGEKLUUHTZCSIP-UHFFFAOYSA-N Isobornyl acetate Natural products C1CC2(C)C(OC(=O)C)CC1C2(C)C KGEKLUUHTZCSIP-UHFFFAOYSA-N 0.000 claims 4
- 235000019501 Lemon oil Nutrition 0.000 claims 4
- 244000178231 Rosmarinus officinalis Species 0.000 claims 4
- DOOTYTYQINUNNV-UHFFFAOYSA-N Triethyl citrate Chemical compound CCOC(=O)CC(O)(C(=O)OCC)CC(=O)OCC DOOTYTYQINUNNV-UHFFFAOYSA-N 0.000 claims 4
- AXMVYSVVTMKQSL-UHFFFAOYSA-N UNPD142122 Natural products OC1=CC=C(C=CC=O)C=C1O AXMVYSVVTMKQSL-UHFFFAOYSA-N 0.000 claims 4
- 239000001940 [(1R,4S,6R)-1,7,7-trimethyl-6-bicyclo[2.2.1]heptanyl] acetate Substances 0.000 claims 4
- OOCCDEMITAIZTP-UHFFFAOYSA-N allylic benzylic alcohol Natural products OCC=CC1=CC=CC=C1 OOCCDEMITAIZTP-UHFFFAOYSA-N 0.000 claims 4
- 229940062909 amyl salicylate Drugs 0.000 claims 4
- JGQFVRIQXUFPAH-UHFFFAOYSA-N beta-citronellol Natural products OCCC(C)CCCC(C)=C JGQFVRIQXUFPAH-UHFFFAOYSA-N 0.000 claims 4
- POIARNZEYGURDG-FNORWQNLSA-N beta-damascenone Chemical compound C\C=C\C(=O)C1=C(C)C=CCC1(C)C POIARNZEYGURDG-FNORWQNLSA-N 0.000 claims 4
- CKDOCTFBFTVPSN-UHFFFAOYSA-N borneol Natural products C1CC2(C)C(C)CC1C2(C)C CKDOCTFBFTVPSN-UHFFFAOYSA-N 0.000 claims 4
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- KBEBGUQPQBELIU-UHFFFAOYSA-N cinnamic acid ethyl ester Natural products CCOC(=O)C=CC1=CC=CC=C1 KBEBGUQPQBELIU-UHFFFAOYSA-N 0.000 claims 4
- KJPRLNWUNMBNBZ-UHFFFAOYSA-N cinnamic aldehyde Natural products O=CC=CC1=CC=CC=C1 KJPRLNWUNMBNBZ-UHFFFAOYSA-N 0.000 claims 4
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- 239000001279 citrus aurantifolia swingle expressed oil Substances 0.000 claims 4
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- YKFKEYKJGVSEIX-UHFFFAOYSA-N cyclohexanone, 4-(1,1-dimethylethyl)- Chemical compound CC(C)(C)C1CCC(=O)CC1 YKFKEYKJGVSEIX-UHFFFAOYSA-N 0.000 claims 4
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- 239000003921 oil Substances 0.000 claims 4
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- QNGNSVIICDLXHT-UHFFFAOYSA-N para-ethylbenzaldehyde Natural products CCC1=CC=C(C=O)C=C1 QNGNSVIICDLXHT-UHFFFAOYSA-N 0.000 claims 4
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- KWVISVAMQJWJSZ-VKROHFNGSA-N solasodine Chemical compound O([C@@H]1[C@@H]([C@]2(CC[C@@H]3[C@@]4(C)CC[C@H](O)CC4=CC[C@H]3[C@@H]2C1)C)[C@@H]1C)[C@]11CC[C@@H](C)CN1 KWVISVAMQJWJSZ-VKROHFNGSA-N 0.000 claims 4
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- YUVKTUCPWGPBLJ-UHFFFAOYSA-N tert-butyl 2-cyclohexylacetate Chemical compound CC(C)(C)OC(=O)CC1CCCCC1 YUVKTUCPWGPBLJ-UHFFFAOYSA-N 0.000 claims 4
- CXWXQJXEFPUFDZ-UHFFFAOYSA-N tetralin Chemical compound C1=CC=C2CCCCC2=C1 CXWXQJXEFPUFDZ-UHFFFAOYSA-N 0.000 claims 4
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- 239000001069 triethyl citrate Substances 0.000 claims 4
- VMYFZRTXGLUXMZ-UHFFFAOYSA-N triethyl citrate Natural products CCOC(=O)C(O)(C(=O)OCC)C(=O)OCC VMYFZRTXGLUXMZ-UHFFFAOYSA-N 0.000 claims 4
- 235000013769 triethyl citrate Nutrition 0.000 claims 4
- 229930007850 β-damascenone Natural products 0.000 claims 4
- NFLGAXVYCFJBMK-IUCAKERBSA-N (-)-isomenthone Chemical compound CC(C)[C@@H]1CC[C@H](C)CC1=O NFLGAXVYCFJBMK-IUCAKERBSA-N 0.000 claims 3
- NFLGAXVYCFJBMK-UHFFFAOYSA-N isomenthone Natural products CC(C)C1CCC(C)CC1=O NFLGAXVYCFJBMK-UHFFFAOYSA-N 0.000 claims 3
- POIARNZEYGURDG-UHFFFAOYSA-N beta-damascenone Natural products CC=CC(=O)C1=C(C)C=CCC1(C)C POIARNZEYGURDG-UHFFFAOYSA-N 0.000 claims 2
- 125000003903 2-propenyl group Chemical group [H]C([*])([H])C([H])=C([H])[H] 0.000 claims 1
- 239000002253 acid Substances 0.000 claims 1
- FUZZWVXGSFPDMH-UHFFFAOYSA-N hexanoic acid Chemical compound CCCCCC(O)=O FUZZWVXGSFPDMH-UHFFFAOYSA-N 0.000 claims 1
- 239000000463 material Substances 0.000 description 20
- 239000012876 carrier material Substances 0.000 description 4
- 239000000126 substance Substances 0.000 description 4
- 241000196324 Embryophyta Species 0.000 description 3
- 241001529742 Rosmarinus Species 0.000 description 3
- 235000019499 Citrus oil Nutrition 0.000 description 2
- 229920002472 Starch Polymers 0.000 description 2
- 238000006243 chemical reaction Methods 0.000 description 2
- 239000010500 citrus oil Substances 0.000 description 2
- 230000006870 function Effects 0.000 description 2
- 230000001590 oxidative effect Effects 0.000 description 2
- 235000012658 paprika extract Nutrition 0.000 description 2
- 235000019698 starch Nutrition 0.000 description 2
- 239000008107 starch Substances 0.000 description 2
- 206010070834 Sensitisation Diseases 0.000 description 1
- 230000002009 allergenic effect Effects 0.000 description 1
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 1
- 230000003111 delayed effect Effects 0.000 description 1
- 230000002939 deleterious effect Effects 0.000 description 1
- 238000001514 detection method Methods 0.000 description 1
- 238000003113 dilution method Methods 0.000 description 1
- 230000003467 diminishing effect Effects 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 239000003112 inhibitor Substances 0.000 description 1
- 230000002401 inhibitory effect Effects 0.000 description 1
- 239000007788 liquid Substances 0.000 description 1
- 229910052760 oxygen Inorganic materials 0.000 description 1
- 239000001301 oxygen Substances 0.000 description 1
- 238000005057 refrigeration Methods 0.000 description 1
- 230000035945 sensitivity Effects 0.000 description 1
- 230000008313 sensitization Effects 0.000 description 1
- 230000006641 stabilisation Effects 0.000 description 1
- 238000011105 stabilization Methods 0.000 description 1
- 230000002195 synergetic effect Effects 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
- A23—FOODS OR FOODSTUFFS; TREATMENT THEREOF, NOT COVERED BY OTHER CLASSES
- A23L—FOODS, FOODSTUFFS OR NON-ALCOHOLIC BEVERAGES, NOT OTHERWISE PROVIDED FOR; PREPARATION OR TREATMENT THEREOF
- A23L27/00—Spices; Flavouring agents or condiments; Artificial sweetening agents; Table salts; Dietetic salt substitutes; Preparation or treatment thereof
- A23L27/70—Fixation, conservation, or encapsulation of flavouring agents
-
- 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
- A61K8/96—Cosmetics or similar toiletry preparations characterised by the composition containing materials, or derivatives thereof of undetermined constitution
- A61K8/97—Cosmetics or similar toiletry preparations characterised by the composition containing materials, or derivatives thereof of undetermined constitution from algae, fungi, lichens or plants; from derivatives thereof
- A61K8/9783—Angiosperms [Magnoliophyta]
- A61K8/9789—Magnoliopsida [dicotyledons]
-
- C—CHEMISTRY; METALLURGY
- C11—ANIMAL OR VEGETABLE OILS, FATS, FATTY SUBSTANCES OR WAXES; FATTY ACIDS THEREFROM; DETERGENTS; CANDLES
- C11B—PRODUCING, e.g. BY PRESSING RAW MATERIALS OR BY EXTRACTION FROM WASTE MATERIALS, REFINING OR PRESERVING FATS, FATTY SUBSTANCES, e.g. LANOLIN, FATTY OILS OR WAXES; ESSENTIAL OILS; PERFUMES
- C11B9/00—Essential oils; Perfumes
-
- 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
- A61K2800/40—Chemical, physico-chemical or functional or structural properties of particular ingredients
- A61K2800/52—Stabilizers
- A61K2800/522—Antioxidants; Radical scavengers
Definitions
- the invention relates to a method for preventing or diminishing the production of auto-oxidative products, primarily peroxides, in fragrance and flavor (F&F) products.
- Peroxides that are formed in F&F products when the latter auto-oxidize can cause problematic reactions in humans, either of an allergenic or sensitization nature, when the products are utilized in foods, cosmetics and the like. These reactions can be highly disruptive to the life of the sufferer and can have long and short term effects on the health of individuals exposed thereto.
- Antioxidants are known in the industry and function as inhibitory substances that prevent or inhibit oxidative changes in materials in which they are incorporated due to the presence of oxygen or other oxidative pressures therein.
- the antioxidants act as scavengers of any free radicals that form during auto-oxidation, thereby short-circuiting the oxidation process.
- a fragrance or flavor composition comprising a fragrance effective amount of a fragrance compound, a flavor effective amount of a flavor compound or mixture thereof and an amount of a natural antioxidant that is substantially inert with respect to the fragrance compound, flavor compound or mixture thereof in an amount sufficient to substantially stabilize the fragrance or flavor composition against auto-oxidation.
- Another embodiment of the invention comprises a method for stabilizing a fragrance or flavor composition against auto-oxidation, the fragrance or flavor composition comprising a fragrance effective amount of a fragrance compound, a flavor effective amount of a flavor compound or mixture thereof, the method comprising the step of incorporating a stabilizing amount of a natural antioxidant in the composition.
- a still further embodiment of the invention concerns a method of using a fragrance or flavor composition, the fragrance or flavor composition comprising a fragrance effective amount of a fragrance compound, a flavor effective amount of a flavor compound or mixture thereof and an amount of a natural antioxidant that is substantially inert with respect to the fragrance compound, flavor compound or mixture thereof in an amount sufficient to substantially stabilize the fragrance or flavor composition against auto-oxidation, comprising forming a composition containing an effective amount of the composition with a suitable carrier.
- Another embodiment of the invention relates to an article of manufacture comprising a carrier having a fragrance or flavor composition incorporated therein wherein the fragrance or flavor composition comprises a fragrance effective amount of a fragrance compound, a flavor effective amount of a flavor compound or mixture thereof and an amount of a natural antioxidant that is substantially inert with respect to the fragrance compound, flavor compound or mixture thereof in an amount sufficient to substantially stabilize the fragrance or flavor composition against auto-oxidation.
- a final embodiment of the invention concerns articles of manufacture comprising cosmetic products, foods (including prepared foods, meats and the like), seasoning and flavoring blends that include effective amounts of one of the above-described compositions.
- the invention is predicated on the discovery that the utilization as antioxidants the materials found in the Labiatae family of plants, primarily rosemary, effectively inhibit the formation of peroxides when incorporated in F&F materials. Moreover, the antioxidants function effectively without significantly altering the flavor and/or fragrance properties of the F&F materials.
- the antioxidant materials are extracted from the plant and placed in a form which is conducive to introduction into F&F products.
- This invention 1 makes use, but not limited to, the following compounds found in, e.g., rosemary: carnosic acid, carnasol, rosmanol, rosmadial, and rosmarinic acid. With the addition of this extracted material via a carrier material to the finished F&F the onset of oxidation is eliminated or delayed significantly.
- a typical F&F product will have added to it an amount of the rosemary (or other Labiatae extract) in the parts per billion (ppb) or parts per million (ppm) range.
- the amount added will vary depending upon the sensitivity of the F&F material to oxidation.
- the extract is preferably incorporated in the F&F product via a carrier material.
- the carrier material preferably comprises the same material as that to be stabilized.
- the carrier employed would be orange oil.
- the antioxidant material and orange oil would be combined to form masterbatches of known concentrations. Portions of the masterbatches would then be combined with the F&F material to form the finished product having the desired proportions of ingredients.
- the antioxidant material contain more than one of the antioxidant materials found in the plant material inasmuch as the antioxidative materials are found to have a positive synergistic effect on each other if they are present in combination.
- Material desired fIMm earner Citrus Oils 50 to 2000 citrus oil Oleoresin Paprika 500 to 10000 oleoresin paprika Aroma chemicals 10 to 100 aroma chemical Seasoning blends 500 to 2000 starch or oleo, or liquid.
Landscapes
- Life Sciences & Earth Sciences (AREA)
- Health & Medical Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- General Health & Medical Sciences (AREA)
- Public Health (AREA)
- Veterinary Medicine (AREA)
- Engineering & Computer Science (AREA)
- Chemical & Material Sciences (AREA)
- Mycology (AREA)
- Biotechnology (AREA)
- Botany (AREA)
- Birds (AREA)
- Epidemiology (AREA)
- Microbiology (AREA)
- Food Science & Technology (AREA)
- Nutrition Science (AREA)
- Polymers & Plastics (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Oil, Petroleum & Natural Gas (AREA)
- Wood Science & Technology (AREA)
- Organic Chemistry (AREA)
- Fats And Perfumes (AREA)
Abstract
A fragrance or flavor composition comprising a fragrance compound, a flavor compound or mixture thereof and an amount of a natural antioxidant that is inert with respect to the fragrance compound, flavor compound or mixture thereof in an amount sufficient to substantially stabilize the fragrance or flavor composition against auto-oxidation.
Description
Method and Composition for the Prevention of the Auto-oxidation of
Flavors and Fragrances
BACKGROUND OF THE INVENTION Field of the Invention
The invention relates to a method for preventing or diminishing the production of auto-oxidative products, primarily peroxides, in fragrance and flavor (F&F) products. Description of the Prior Art
Peroxides that are formed in F&F products when the latter auto-oxidize can cause problematic reactions in humans, either of an allergenic or sensitization nature, when the products are utilized in foods, cosmetics and the like. These reactions can be highly disruptive to the life of the sufferer and can have long and short term effects on the health of individuals exposed thereto.
Antioxidants are known in the industry and function as inhibitory substances that prevent or inhibit oxidative changes in materials in which they are incorporated due to the presence of oxygen or other oxidative pressures therein. The antioxidants act as scavengers of any free radicals that form during auto-oxidation, thereby short-circuiting the oxidation process.
Heretofore, if materials were to be stabilized against auto-oxidation without the addition of significant odor or taste to the materials to be protected, synthetic antioxidants were required. However, the use of synthetic anti-oxidants has met with disfavor in recent years because of the perceived deleterious effects thereof on the environment. Indeed, some countries have banned the use of synthetic anti-oxidants, particularly in the F&F industry.
It is an object of the present invention to provide a natural auto-oxidative inhibitor that would be acceptable for use around the world as an antioxidant system and which does
not impart a significant odor or flavor profile to the material in which it is incorporated for stabilization purposes.
SUMMARY OF THE INVENTION
The above and other objects are realized by the present invention, one embodiment of which relates to a fragrance or flavor composition comprising a fragrance effective amount of a fragrance compound, a flavor effective amount of a flavor compound or mixture thereof and an amount of a natural antioxidant that is substantially inert with respect to the fragrance compound, flavor compound or mixture thereof in an amount sufficient to substantially stabilize the fragrance or flavor composition against auto-oxidation.
Another embodiment of the invention comprises a method for stabilizing a fragrance or flavor composition against auto-oxidation, the fragrance or flavor composition comprising a fragrance effective amount of a fragrance compound, a flavor effective amount of a flavor compound or mixture thereof, the method comprising the step of incorporating a stabilizing amount of a natural antioxidant in the composition.
A still further embodiment of the invention concerns a method of using a fragrance or flavor composition, the fragrance or flavor composition comprising a fragrance effective amount of a fragrance compound, a flavor effective amount of a flavor compound or mixture thereof and an amount of a natural antioxidant that is substantially inert with respect to the fragrance compound, flavor compound or mixture thereof in an amount sufficient to substantially stabilize the fragrance or flavor composition against auto-oxidation, comprising forming a composition containing an effective amount of the composition with a suitable carrier.
Another embodiment of the invention relates to an article of manufacture comprising a carrier having a fragrance or flavor composition incorporated therein wherein the fragrance or flavor composition comprises a fragrance effective amount of a fragrance compound, a flavor effective amount of a flavor compound or mixture thereof and an amount of a natural antioxidant that is substantially inert with respect to the fragrance compound, flavor compound or mixture thereof in an amount sufficient to substantially stabilize the fragrance or flavor composition against auto-oxidation.
A final embodiment of the invention concerns articles of manufacture comprising cosmetic products, foods (including prepared foods, meats and the like), seasoning and flavoring blends that include effective amounts of one of the above-described compositions.
DETAILED DESCRIPTION OF THE INVENTION
Advantages associated with the present invention include:
1) Enables the storage of materials without or less refrigeration than heretofore.
2) Non-obvious over synthetic anti-oxidants in that latter are prone to be reactive with the products to be stabilized.
The invention is predicated on the discovery that the utilization as antioxidants the materials found in the Labiatae family of plants, primarily rosemary, effectively inhibit the formation of peroxides when incorporated in F&F materials. Moreover, the antioxidants function effectively without significantly altering the flavor and/or fragrance properties of the F&F materials. In a typical operation, the antioxidant materials are extracted from the plant and placed in a form which is conducive to introduction into F&F products. This invention1 makes use, but not limited to, the following compounds found in, e.g., rosemary: carnosic acid, carnasol, rosmanol, rosmadial, and rosmarinic acid. With the addition of this extracted
material via a carrier material to the finished F&F the onset of oxidation is eliminated or delayed significantly. In accordance with this invention, a typical F&F product will have added to it an amount of the rosemary (or other Labiatae extract) in the parts per billion (ppb) or parts per million (ppm) range. The amount added will vary depending upon the sensitivity of the F&F material to oxidation. The extract is preferably incorporated in the F&F product via a carrier material. The carrier material preferably comprises the same material as that to be stabilized. For Example, to protect orange oil the carrier employed would be orange oil. The antioxidant material and orange oil would be combined to form masterbatches of known concentrations. Portions of the masterbatches would then be combined with the F&F material to form the finished product having the desired proportions of ingredients. It will be understood by those skilled in the art that any suitable method for combining the antioxidant with the F&F material may be employed. For purposes of illustrating the invention herein, the direct dilution method will be described. It has been discovered that by adding a carrier material that contains the rosemary extract in predetermined concentrations to a F&F product the latter will be protected against peroxide formation. [Methods for the detection of peroxides include titrametric utilizing the Peroxide value method found on page 198 of the Food Chemical Codex, 4th Edition.]
It is most preferred that the antioxidant material contain more than one of the antioxidant materials found in the plant material inasmuch as the antioxidative materials are found to have a positive synergistic effect on each other if they are present in combination.
Examples
Material desired fIMm) earner Citrus Oils 50 to 2000 citrus oil Oleoresin Paprika 500 to 10000 oleoresin paprika Aroma chemicals 10 to 100 aroma chemical Seasoning blends 500 to 2000 starch or oleo, or liquid.
1. 180 kg of Orange oil had 1.8 kg of orange oil spiked with 5000 ppm of the rosemary extract to give a final value on 50 ppm.
2. 5000 pounds of a seasoning blend had 50 pounds of starch added spiked with 200000 ppm of rosemary extract added.
Claims
1. A fragrance or flavor composition comprising a fragrance effective amount of a fragrance compound, a flavor effective amount of a flavor compound or mixture thereof and an amount of a natural antioxidant that is substantially inert with respect to said fragrance compound, flavor compound or mixture thereof in an amount sufficient to substantially stabilize said fragrance or flavor composition against auto-oxidation.
2. The composition of claim 1 wherein said natural anti-oxidant is present in an amount sufficient to stabilize said composition against auto-oxidation which results in the formation of peroxides.
3. The composition of claim 1 wherein said natural antioxidant is an extract of a member of the family Labiatae or an active antioxidant ingredient thereof.
4. The composition of claim 3 wherein said Labiatae family member is rosemary.
5. The composition of claim 4 wherein said antioxidant ingredient of said rosemary extract is carnosic acid, carnasol, rosmanol, rosmadial, rosmarinic acid or mixtures thereof.
6. The composition of claim 1 wherein said fragrance compound, flavor compound or mixture thereof is citral, p-cymene, borneol, cinnamic alcohol, cinnamic aldehyde, dimethyl benzyl carbinol, 1 -menthol, fenchyl alcohol, phenyl ethyl alcohol, o-tert-butyl cyclohexanol, 2-sec-butyl cyclohexanol, lauryl alcohol, 2-methyl undecanol, hexyl alcohol, citronellol,
dihydro myrcenol, iso-amyl alcohol, tetrahydro linalool, dipropylene glycol, hexylene glycol, p-tert-butyl cyclohexanol, phenyl hexanol, 3,3,5-trimethyl hexanol, cis-trimethyl cyclohexanol, trans-2 -hexanol, bornyl methoxy cyclohexanol, ethylene tridecane dioate, amyl salicylate, dimethyl benzyl carbinyl acetate, fenchyl acetate, n-hexyl salicylate, iso-bornyl acetate, o-tert-butyl cyclohexyl acetate, p-tert-butyl cyclohexyl acetate, phenyl ethyl acetate, tricyclodecenyl acetate, styrallyl acetate, methyl salicylate, allylamyl glycolate, allyl capronate, ethyl capronate, ethyl cinnamate, geranyl acetate, n-hexyl acetate, iso-amyl acetate, iso-nonyl acetate, triethyl citrate, rosephenene, dihydro mycenyl acetate, butyl-2- methyl varerate, trans-2-hexenyl acetate, dl-camphor, coumarin, pentyl cyclopentanone, iso- menthone, p-hydroxy phenyl butanone, 6-acetyl-l,l,3,4,4,6-hexamethyl tetrahydronaphthalene, ionone, p-tert-butyl cyclohexanone, o-tert-butyl cyclohexanone, 1- (2,6,6-trimethyl-l ,3-cyclohexadiene-l -yl)-2-butene-l -one(Damascenone), l-(2,6,6-trimethyl- 2-cyclohexene l-yl)-2-butene-l-one(Damascone .alpha.), l-(2,6,6-trimethyl-l-cyclohexene- 1 -yl)-2-butene- 1 -one(Damascone .beta.), 1 -(2,6,6-trimethyl-3-cyclohexene- 1 -yl)-2-butene- 1 - one (Delta Damascone), Dihydro Floriffone TD), p-mentha-8-thiol-3-one, gamma.- undecalactone, phenyl acetaldehyde dimethylacetal, octyl aldehyde, citronellal, methyl nonyl acetaldehyde, diphenyl oxide, phenyl ethyl isoamyl ether, l,3,4,6,7,8-hexahydro-4,6,6,7,8,8- hexamethyl-cyclopenta-. gamma. -2-benzopyra n (Galaxolide), eucalyptus oil, lavender oil, lime oil, lemon oil, orange oil, grapefruit oil, pineneedle oil, peppermint oil, rosemary oil, spearmint oil, d'limonene, benzaldehyde or mixtures thereof.
7. A method for stabilizing a fragrance or flavor composition against auto-oxidation, said fragrance or flavor composition comprising a fragrance effective amount of a fragrance compound, a flavor effective amount of a flavor compound or mixture thereof, said method
comprising the step of incorporating a stabilizing amount of a natural antioxidant in said composition.
8. The method of claim 7 wherein said natural anti-oxidant is present in an amount sufficient to stabilize said composition against auto-oxidation which results in the formation of peroxides.
9. The method of claim 7 wherein said natural antioxidant is an extract of a member of the family Labiatae or an active antioxidant ingredient thereof.
10. The method of claim 9 wherein said Labiatae family member is rosemary.
11. The method of claim 10 wherein said antioxidant ingredient of said rosemary extract is carnosic acid, carnasol, rosmanol, rosmadial, rosmarinic acid or mixtures thereof.
12. The method of claim 7 wherein said fragrance compound or mixture thereof is citral, p-cymene, borneol, cinnamic alcohol, cinnamic aldehyde, dimethyl benzyl carbinol, 1- menthol, fenchyl alcohol, phenyl ethyl alcohol, o-tert-butyl cyclohexanol, 2-sec-butyl cyclohexanol, lauryl alcohol, 2-methyl undecanol, hexyl alcohol, citronellol, dihydro myrcenol, iso-amyl alcohol, tetrahydro linalool, dipropylene glycol, hexylene glycol, p-tert- butyl cyclohexanol, phenyl hexanol, 3,3,5-trimethyl hexanol, cis-trimethyl cyclohexanol, trans-2-hexanol, bornyl methoxy cyclohexanol, ethylene tridecane dioate, amyl salicylate, dimethyl benzyl carbinyl acetate, fenchyl acetate, n-hexyl salicylate, iso-bornyl acetate, o- tert-butyl cyclohexyl acetate, p-tert-butyl cyclohexyl acetate, phenyl ethyl acetate,
tricyclodecenyl acetate, styrallyl acetate, methyl salicylate, allylamyl glycolate, allyl capronate, ethyl capronate, ethyl cinnamate, geranyl acetate, n-hexyl acetate, iso-amyl acetate, iso-nonyl acetate, triethyl citrate, rosephenene, dihydro mycenyl acetate, butyl-2- methyl varerate, trans-2-hexenyl acetate, dl-camphor, coumarin, pentyl cyclopentanone, iso- menthone, p-hydroxy phenyl butanone, 6-acetyl-l,l,3,4,4,6-hexamefhyl tetrahydronaphthalene, ionone, p-tert-butyl cyclohexanone, o-tert-butyl cyclohexanone, 1- (2,6,6-trimethyl- 1 ,3-cyclohexadiene- 1 -yl)-2-butene- 1 -one(Damascenone), 1 -(2,6,6-trimethyl- 2-cyclohexene l-yl)-2-butene-l-one(Damascone .alpha.), 1 -(2,6,6-trimethyl- l-cyclohexene- 1 -yl)-2-butene- 1 -one(Damascone .beta.), 1 -(2,6,6-trimethyl-3 -cyclohexene-1 -yl)-2-butene- 1 - one (Delta Damascone), Dihydro Floriffone TD), p-mentha-8-thiol-3-one, gamma.- undecalactone, phenyl acetaldehyde dimethylacetal, octyl aldehyde, citronellal, methyl nonyl acetaldehyde, diphenyl oxide, phenyl ethyl isoamyl ether, 1,3 ,4 ,6,7,8-hexahydro-4 ,6,6,7,8,8- hexamethyl-cyclopenta-.gamma.-2-benzopyra n (Galaxolide), eucalyptus oil, lavender oil, lime oil, lemon oil, orange oil, grapefruit oil, pineneedle oil, peppermint oil, rosemary oil, spearmint oil, d'limonene, benzaldehyde or mixtures thereof.
13. A method of using a fragrance or flavor composition, said fragrance or flavor composition comprising a fragrance effective amount of a fragrance compound, a flavor effective amount of a flavor compound or mixture thereof and an amount of a natural antioxidant that is substantially inert with respect to said fragrance compound, flavor compound or mixture thereof in an amount sufficient to substantially stabilize said fragrance or flavor composition against auto-oxidation, comprising forming a composition containing an effective amount of said composition with a suitable carrier.
14. The method of claim 13 wherein said natural anti-oxidant is present in an amount sufficient to stabilize said composition against auto-oxidation which results in the formation of peroxides.
15. The method of claim 13 wherein said natural antioxidant is an extract of a member of the family Labiatae or an active antioxidant ingredient thereof.
16. The method of claim 15 wherein said Labiatae family member is rosemary.
17. The method of claim 16 wherein said antioxidant ingredient of said rosemary extract is carnosic acid, carnasol, rosmanol, rosmadial, rosmarinic acid or mixtures thereof.
18. The method of claim 13 wherein said fragrance compound or mixture thereof is citral, p-cymene, borneol, cinnamic alcohol, cinnamic aldehyde, dimethyl benzyl carbinol, 1- menthol, fenchyl alcohol, phenyl ethyl alcohol, o-tert-butyl cyclohexanol, 2-sec-butyl cyclohexanol, lauryl alcohol, 2-methyl undecanol, hexyl alcohol, citronellol, dihydro myrcenol, iso-amyl alcohol, tetrahydro linalool, dipropylene glycol, hexylene glycol, p-tert- butyl cyclohexanol, phenyl hexanol, 3,3,5-trimethyl hexanol, cis-trimethyl cyclohexanol, trans-2-hexanol, bornyl methoxy cyclohexanol, ethylene tridecane dioate, amyl salicylate, dimethyl benzyl carbinyl acetate, fenchyl acetate, n-hexyl salicylate, iso-bornyl acetate, o- tert-butyl cyclohexyl acetate, p-tert-butyl cyclohexyl acetate, phenyl ethyl acetate, tricyclodecenyl acetate, styrallyl acetate, methyl salicylate, allylamyl glycolate, allyl capronate, ethyl capronate, ethyl cinnamate, geranyl acetate, n-hexyl acetate, iso-amyl acetate, iso-nonyl acetate, triethyl citrate, rosephenene, dihydro mycenyl acetate, butyl-2-
methyl varerate, trans-2-hexenyl acetate, dl-camphor, coumarin, pentyl cyclopentanone, iso- menfhone, p-hydroxy phenyl butanone, 6-acetyl-l,l,3,4,4,6-hexamethyl tetrahydronaphthalene, ionone, p-tert-butyl cyclohexanone, o-tert-butyl cyclohexanone, 1 - (2,6,6-trimethyl-l ,3-cyclohexadiene- 1 -yl)-2-butene-l -one(Damascenone), 1 -(2,6,6-trimethyl- 2-cyclohexene l-yl)-2-butene-l-one(Damascone .alpha.), 1 -(2,6,6-trimethyl- 1-cyclohexene- 1 -yl)-2-butene- 1 -one(Damascone .beta.), 1 -(2,6,6-trimethyl-3-cyclohexene- 1 -yl)-2-butene- 1 - one (Delta Damascone), Dihydro Floriffone TD), p-mentha-8-thiol-3-one, gamma.- undecalactone, phenyl acetaldehyde dimethylacetal, octyl aldehyde, citronellal, methyl nonyl acetaldehyde, diphenyl oxide, phenyl ethyl isoamyl ether, l,3,4,6,7,8-hexahydro-4,6,6,7,8,8- hexamethyl-cyclopenta-.gamma.-2-benzopyra n (Galaxolide), eucalyptus oil, lavender oil, lime oil, lemon oil, orange oil, grapefruit oil, pineneedle oil, peppermint oil, rosemary oil, spearmint oil, d'limonene, benzaldehyde or mixtures thereof.
19. The method of claim 9 wherein said carrier is a food, cosmetic product, prepared food, meat, seasoning or flavoring blend.
20. An article of manufacture comprising a carrier having a fragrance or flavor composition incorporated therein wherein said fragrance or flavor composition comprises a fragrance effective amount of a fragrance compound, a flavor effective amount of a flavor compound or mixture thereof and an amount of a natural antioxidant that is substantially inert with respect to said fragrance compound, flavor compound or mixture thereof in an amount sufficient to substantially stabilize said fragrance or flavor composition against auto- oxidation.
21. The article of manufacture of claim 20 wherein said natural anti-oxidant is present in an amount sufficient to stabilize said composition against auto-oxidation which results in the formation of peroxides.
22. The article of manufacture of claim 20 wherein said natural antioxidant is an extract of a member of the family Labiatae or an active antioxidant ingredient thereof.
23. The article of manufacture of claim 22 wherein said Labiatae family member is rosemary.
24. The article of manufacture of claim 23 wherein said antioxidant ingredient of said rosemary extract is camosic acid, camasol, rosmanol, rosmadial, rosmarinic acid or mixtures thereof.
25. The article of manufacture of claim 20 wherein said fragrance compound or mixture thereof is citral, p-cymene, borneol, cinnamic alcohol, cinnamic aldehyde, dimethyl benzyl carbinol, 1 -menthol, fenchyl alcohol, phenyl ethyl alcohol, o-tert-butyl cyclohexanol, 2-sec- butyl cyclohexanol, lauryl alcohol, 2-methyl undecanol, hexyl alcohol, citronellol, dihydro myrcenol, iso-amyl alcohol, tetrahydro linalool, dipropylene glycol, hexylene glycol, p-tert- butyl cyclohexanol, phenyl hexanol, 3,3,5-trimethyl hexanol, cis-trimethyl cyclohexanol, trans-2-hexanol, bornyl methoxy cyclohexanol, ethylene tridecane dioate, amyl salicylate, dimethyl benzyl carbinyl acetate, fenchyl acetate, n-hexyl salicylate, iso-bornyl acetate, o- tert-butyl cyclohexyl acetate, p-tert-butyl cyclohexyl acetate, phenyl ethyl acetate, tricyclodecenyl acetate, styrallyl acetate, methyl salicylate, allylamyl glycolate, allyl
capronate, ethyl capronate, ethyl cinnamate, geranyl acetate, n-hexyl acetate, iso-amyl acetate, iso-nonyl acetate, triethyl citrate, rosephenene, dihydro mycenyl acetate, butyl-2- methyl varerate, trans-2-hexenyl acetate, dl-camphor, coumarin, pentyl cyclopentanone, iso- menthone, p-hydroxy phenyl butanone, 6-acetyl-l,l,3,4,4,6-hexamethyl tetrahydronaphthalene, ionone, p-tert-butyl cyclohexanone, o-tert-butyl cyclohexanone, 1- (2,6,6-trimethyl-l,3-cyclohexadiene-l-yl)-2-butene-l-one(Damascenone), l-(2,6,6-trimethyl- 2-cyclohexene l-yl)-2-butene-l-one(Damascone .alpha.), 1 -(2,6,6-trimethyl- 1-cyclohexene- 1 -yl)-2-butene- 1 -one(Damascone .beta.), 1 -(2,6,6-trimethyl-3-cyclohexene- 1 -yl)-2-butene- 1 - one (Delta Damascone), Dihydro Floriffone TD), p-mentha-8-thiol-3-one, gamma. - undecalactone, phenyl acetaldehyde dimethylacetal, octyl aldehyde, citronellal, methyl nonyl acetaldehyde, diphenyl oxide, phenyl ethyl isoamyl ether, l,3,4,6,7,8-hexahydro-4,6,6,7,8,8- hexamethyl-cyclopenta-.gamma.-2-benzopyra n (Galaxolide), eucalyptus oil, lavender oil, lime oil, lemon oil, orange oil, grapefruit oil, pineneedle oil, peppermint oil, rosemary oil, spearmint oil, d'limonene, benzaldehyde or mixtures thereof.
26. The article of manufacture of claim 20 wherein said carrier is a food, cosmetic product, prepared food, meat, seasoning or flavoring blend.
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| PCT/US2002/033800 WO2004039160A1 (en) | 2001-10-18 | 2002-10-23 | Method and composition for the prevention of the auto-oxidation of flavors and fragrances |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| EP1581058A1 EP1581058A1 (en) | 2005-10-05 |
| EP1581058A4 true EP1581058A4 (en) | 2006-11-29 |
Family
ID=34311694
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| EP02773846A Withdrawn EP1581058A4 (en) | 2002-10-23 | 2002-10-23 | Method and composition for the prevention of the auto-oxidation of flavors and fragrances |
Country Status (2)
| Country | Link |
|---|---|
| EP (1) | EP1581058A4 (en) |
| AU (1) | AU2002337941A1 (en) |
Citations (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO1993006190A1 (en) * | 1991-09-20 | 1993-04-01 | Norac Technologies Inc. | Antioxidant oleoresin compositions and a process for their production |
| US5431912A (en) * | 1992-10-22 | 1995-07-11 | L'oreal | Cosmetic or dermopharmaceutical composition containing, in combination, a lauroylmethionate of a basic amino acid and at least one polyphenol |
| GB2301520A (en) * | 1995-06-02 | 1996-12-11 | Kalamazoo Holdings Inc | Electrostatic deposition of a liquid food composition |
| WO2000028827A1 (en) * | 1998-11-12 | 2000-05-25 | Kalamazoo Holdings, Inc. | Method for preventing off-flavor development and preserving seasoning flavor in irradiated meat and meat products |
| US6231896B1 (en) * | 2000-09-08 | 2001-05-15 | The Goodyear Tire & Rubber Company | Chewing gum base stabilized with carnosic acid |
-
2002
- 2002-10-23 EP EP02773846A patent/EP1581058A4/en not_active Withdrawn
- 2002-10-23 AU AU2002337941A patent/AU2002337941A1/en not_active Abandoned
Patent Citations (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO1993006190A1 (en) * | 1991-09-20 | 1993-04-01 | Norac Technologies Inc. | Antioxidant oleoresin compositions and a process for their production |
| US5431912A (en) * | 1992-10-22 | 1995-07-11 | L'oreal | Cosmetic or dermopharmaceutical composition containing, in combination, a lauroylmethionate of a basic amino acid and at least one polyphenol |
| GB2301520A (en) * | 1995-06-02 | 1996-12-11 | Kalamazoo Holdings Inc | Electrostatic deposition of a liquid food composition |
| WO2000028827A1 (en) * | 1998-11-12 | 2000-05-25 | Kalamazoo Holdings, Inc. | Method for preventing off-flavor development and preserving seasoning flavor in irradiated meat and meat products |
| US6231896B1 (en) * | 2000-09-08 | 2001-05-15 | The Goodyear Tire & Rubber Company | Chewing gum base stabilized with carnosic acid |
Non-Patent Citations (1)
| Title |
|---|
| See also references of WO2004039160A1 * |
Also Published As
| Publication number | Publication date |
|---|---|
| EP1581058A1 (en) | 2005-10-05 |
| AU2002337941A1 (en) | 2004-05-25 |
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