CA1062904A - Saveurs et aromes contenant un acetaldehyde substitue en alpha, seul ou combine avec une cetone, et methodes pour alterer ou renforcer a l'aide de ces produits les proprietes organoleptiques de produits de consommation - Google Patents

Saveurs et aromes contenant un acetaldehyde substitue en alpha, seul ou combine avec une cetone, et methodes pour alterer ou renforcer a l'aide de ces produits les proprietes organoleptiques de produits de consommation

Info

Publication number: CA1062904A
Authority: CA; Canada
Prior art keywords: trimethyl; beta; composition; cyclohexen; ylacetaldehyde
Prior art date: 1974-09-19
Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.): Expired

Application number

CA234,735A

Other languages

English (en)

Inventor

Alan O. Pittet

Erich M. Klaiber

Manfred H. Vock

Edward J. Shuster

Joaquin Vinals

Anton Van Ouwerkerk

Bernard J. Chant

Arthur L. Liberman

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

International Flavors and Fragrances Inc

Original Assignee

International Flavors and Fragrances Inc

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

1974-09-19

Filing date

1975-09-03

Publication date

1979-09-25

1974-09-19 Priority claimed from US05/507,412 external-priority patent/US3940499A/en

1974-09-19 Priority claimed from US05/507,414 external-priority patent/US3956393A/en

1975-07-24 Priority claimed from US05/598,652 external-priority patent/US4014351A/en

1975-07-24 Priority claimed from US05/598,805 external-priority patent/US4026824A/en

1975-07-24 Priority claimed from US05/598,654 external-priority patent/US3959508A/en

1975-08-04 Priority claimed from US05/601,727 external-priority patent/US4028279A/en

1975-09-03 Application filed by International Flavors and Fragrances Inc filed Critical International Flavors and Fragrances Inc

1979-09-25 Application granted granted Critical

1979-09-25 Publication of CA1062904A publication Critical patent/CA1062904A/fr

Status Expired legal-status Critical Current

Links

239000000203 mixture Substances 0.000 title claims abstract description 356
239000000463 material Substances 0.000 title claims abstract description 53
238000000034 method Methods 0.000 title claims abstract description 43
150000002576 ketones Chemical class 0.000 title claims abstract description 25
230000002708 enhancing effect Effects 0.000 title claims abstract description 8
239000003205 fragrance Substances 0.000 title claims description 44
-1 alpha-substituted acetaldehyde Chemical class 0.000 title description 31
VHTFHZGAMYUZEP-UHFFFAOYSA-N 2,6,6-Trimethyl-1-cyclohexen-1-acetaldehyde Chemical compound CC1=C(CC=O)C(C)(C)CCC1 VHTFHZGAMYUZEP-UHFFFAOYSA-N 0.000 claims abstract description 178
239000002304 perfume Substances 0.000 claims abstract description 93
235000002637 Nicotiana tabacum Nutrition 0.000 claims abstract description 68
239000000796 flavoring agent Substances 0.000 claims abstract description 66
235000019634 flavors Nutrition 0.000 claims abstract description 64
125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims abstract description 21
POIARNZEYGURDG-UHFFFAOYSA-N 1-(2,6,6-trimethylcyclohexa-1,3-dien-1-yl)but-2-en-1-one Chemical compound CC=CC(=O)C1=C(C)C=CCC1(C)C POIARNZEYGURDG-UHFFFAOYSA-N 0.000 claims abstract 12
241000208125 Nicotiana Species 0.000 claims abstract 10
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 81
QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 claims description 49
239000003599 detergent Substances 0.000 claims description 44
239000000344 soap Substances 0.000 claims description 41
RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Natural products CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 claims description 40
238000002360 preparation method Methods 0.000 claims description 39
239000000843 powder Substances 0.000 claims description 37
241000220317 Rosa Species 0.000 claims description 35
ZYTPJAQZYPNGFZ-UHFFFAOYSA-N 1-(6,6-dimethylcyclohexen-1-yl)propan-1-one Chemical compound CCC(=O)C1=CCCCC1(C)C ZYTPJAQZYPNGFZ-UHFFFAOYSA-N 0.000 claims description 33
239000004615 ingredient Substances 0.000 claims description 31
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 27
XPCTZQVDEJYUGT-UHFFFAOYSA-N 3-hydroxy-2-methyl-4-pyrone Chemical compound CC=1OC=CC(=O)C=1O XPCTZQVDEJYUGT-UHFFFAOYSA-N 0.000 claims description 22
239000003921 oil Substances 0.000 claims description 22
XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 claims description 21
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239000002671 adjuvant Substances 0.000 claims description 15
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UZFLPKAIBPNNCA-UHFFFAOYSA-N alpha-ionone Natural products CC(=O)C=CC1C(C)=CCCC1(C)C UZFLPKAIBPNNCA-UHFFFAOYSA-N 0.000 claims description 14
239000011203 carbon fibre reinforced carbon Substances 0.000 claims description 14
125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 13
150000002148 esters Chemical class 0.000 claims description 12
HNAGHMKIPMKKBB-UHFFFAOYSA-N 1-benzylpyrrolidine-3-carboxamide Chemical compound C1C(C(=O)N)CCN1CC1=CC=CC=C1 HNAGHMKIPMKKBB-UHFFFAOYSA-N 0.000 claims description 11
HYMLWHLQFGRFIY-UHFFFAOYSA-N Maltol Natural products CC1OC=CC(=O)C1=O HYMLWHLQFGRFIY-UHFFFAOYSA-N 0.000 claims description 11
OBNCKNCVKJNDBV-UHFFFAOYSA-N butanoic acid ethyl ester Natural products CCCC(=O)OCC OBNCKNCVKJNDBV-UHFFFAOYSA-N 0.000 claims description 11
229940043353 maltol Drugs 0.000 claims description 11
QMMFVYPAHWMCMS-UHFFFAOYSA-N Dimethyl sulfide Chemical compound CSC QMMFVYPAHWMCMS-UHFFFAOYSA-N 0.000 claims description 10
QUKGYYKBILRGFE-UHFFFAOYSA-N benzyl acetate Chemical compound CC(=O)OCC1=CC=CC=C1 QUKGYYKBILRGFE-UHFFFAOYSA-N 0.000 claims description 10
235000013305 food Nutrition 0.000 claims description 10
150000001299 aldehydes Chemical class 0.000 claims description 8
MLFHJEHSLIIPHL-UHFFFAOYSA-N isoamyl acetate Chemical compound CC(C)CCOC(C)=O MLFHJEHSLIIPHL-UHFFFAOYSA-N 0.000 claims description 8
150000001298 alcohols Chemical class 0.000 claims description 7
CREMABGTGYGIQB-UHFFFAOYSA-N carbon carbon Chemical compound C.C CREMABGTGYGIQB-UHFFFAOYSA-N 0.000 claims description 7
BYEVBITUADOIGY-UHFFFAOYSA-N ethyl nonanoate Chemical compound CCCCCCCCC(=O)OCC BYEVBITUADOIGY-UHFFFAOYSA-N 0.000 claims description 6
PQLMXFQTAMDXIZ-UHFFFAOYSA-N isoamyl butyrate Chemical compound CCCC(=O)OCCC(C)C PQLMXFQTAMDXIZ-UHFFFAOYSA-N 0.000 claims description 6
RUVINXPYWBROJD-ONEGZZNKSA-N trans-anethole Chemical compound COC1=CC=C(\C=C\C)C=C1 RUVINXPYWBROJD-ONEGZZNKSA-N 0.000 claims description 6
239000000341 volatile oil Substances 0.000 claims description 6
PHXATPHONSXBIL-UHFFFAOYSA-N xi-gamma-Undecalactone Chemical compound CCCCCCCC1CCC(=O)O1 PHXATPHONSXBIL-UHFFFAOYSA-N 0.000 claims description 6
ICMAFTSLXCXHRK-UHFFFAOYSA-N Ethyl pentanoate Chemical compound CCCCC(=O)OCC ICMAFTSLXCXHRK-UHFFFAOYSA-N 0.000 claims description 5
239000005792 Geraniol Substances 0.000 claims description 5
GLZPCOQZEFWAFX-YFHOEESVSA-N Geraniol Natural products CC(C)=CCC\C(C)=C/CO GLZPCOQZEFWAFX-YFHOEESVSA-N 0.000 claims description 5
229940007550 benzyl acetate Drugs 0.000 claims description 5
229940113087 geraniol Drugs 0.000 claims description 5
MWOOGOJBHIARFG-UHFFFAOYSA-N vanillin Chemical compound COC1=CC(C=O)=CC=C1O MWOOGOJBHIARFG-UHFFFAOYSA-N 0.000 claims description 5
235000012141 vanillin Nutrition 0.000 claims description 5
FGQOOHJZONJGDT-UHFFFAOYSA-N vanillin Natural products COC1=CC(O)=CC(C=O)=C1 FGQOOHJZONJGDT-UHFFFAOYSA-N 0.000 claims description 5
CCRCUPLGCSFEDV-UHFFFAOYSA-N cinnamic acid methyl ester Natural products COC(=O)C=CC1=CC=CC=C1 CCRCUPLGCSFEDV-UHFFFAOYSA-N 0.000 claims description 4
GJRQTCIYDGXPES-UHFFFAOYSA-N iso-butyl acetate Natural products CC(C)COC(C)=O GJRQTCIYDGXPES-UHFFFAOYSA-N 0.000 claims description 4
229940117955 isoamyl acetate Drugs 0.000 claims description 4
FGKJLKRYENPLQH-UHFFFAOYSA-M isocaproate Chemical compound CC(C)CCC([O-])=O FGKJLKRYENPLQH-UHFFFAOYSA-M 0.000 claims description 4
OQAGVSWESNCJJT-UHFFFAOYSA-N isovaleric acid methyl ester Natural products COC(=O)CC(C)C OQAGVSWESNCJJT-UHFFFAOYSA-N 0.000 claims description 4
150000002596 lactones Chemical class 0.000 claims description 4
VAMXMNNIEUEQDV-UHFFFAOYSA-N methyl anthranilate Chemical compound COC(=O)C1=CC=CC=C1N VAMXMNNIEUEQDV-UHFFFAOYSA-N 0.000 claims description 4
CCRCUPLGCSFEDV-BQYQJAHWSA-N methyl trans-cinnamate Chemical compound COC(=O)\C=C\C1=CC=CC=C1 CCRCUPLGCSFEDV-BQYQJAHWSA-N 0.000 claims description 4
150000002825 nitriles Chemical class 0.000 claims description 4
239000001373 (E)-2-methylpent-2-enoic acid Substances 0.000 claims description 3
RRXOQHQFJOQLQR-UHFFFAOYSA-N 1,2,3-trimethoxy-5-prop-1-enylbenzene Chemical compound COC1=CC(C=CC)=CC(OC)=C1OC RRXOQHQFJOQLQR-UHFFFAOYSA-N 0.000 claims description 3
JJYWRQLLQAKNAD-UHFFFAOYSA-N 2-Methyl-2-pentenoic acid Natural products CCC=C(C)C(O)=O JJYWRQLLQAKNAD-UHFFFAOYSA-N 0.000 claims description 3
JJYWRQLLQAKNAD-PLNGDYQASA-N 2-methyl-2-pentenoic acid Chemical compound CC\C=C(\C)C(O)=O JJYWRQLLQAKNAD-PLNGDYQASA-N 0.000 claims description 3
QSJXEFYPDANLFS-UHFFFAOYSA-N Diacetyl Chemical group CC(=O)C(C)=O QSJXEFYPDANLFS-UHFFFAOYSA-N 0.000 claims description 3
RRXOQHQFJOQLQR-AATRIKPKSA-N Isoelemicin Natural products COC1=CC(\C=C\C)=CC(OC)=C1OC RRXOQHQFJOQLQR-AATRIKPKSA-N 0.000 claims description 3
LQKRYVGRPXFFAV-UHFFFAOYSA-N Phenylmethylglycidic ester Chemical compound CCOC(=O)C1OC1(C)C1=CC=CC=C1 LQKRYVGRPXFFAV-UHFFFAOYSA-N 0.000 claims description 3
IKHGUXGNUITLKF-XPULMUKRSA-N acetaldehyde Chemical compound [14CH]([14CH3])=O IKHGUXGNUITLKF-XPULMUKRSA-N 0.000 claims description 3
UZFLPKAIBPNNCA-BQYQJAHWSA-N alpha-ionone Chemical compound CC(=O)\C=C\C1C(C)=CCCC1(C)C UZFLPKAIBPNNCA-BQYQJAHWSA-N 0.000 claims description 3
229940011037 anethole Drugs 0.000 claims description 3
125000004122 cyclic group Chemical group 0.000 claims description 3
PHXATPHONSXBIL-JTQLQIEISA-N gamma-Undecalactone Natural products CCCCCCC[C@H]1CCC(=O)O1 PHXATPHONSXBIL-JTQLQIEISA-N 0.000 claims description 3
229940020436 gamma-undecalactone Drugs 0.000 claims description 3
229940094941 isoamyl butyrate Drugs 0.000 claims description 3
125000004998 naphthylethyl group Chemical group C1(=CC=CC2=CC=CC=C12)CC* 0.000 claims description 3
VWMVAQHMFFZQGD-UHFFFAOYSA-N p-Hydroxybenzyl acetone Natural products CC(=O)CC1=CC=C(O)C=C1 VWMVAQHMFFZQGD-UHFFFAOYSA-N 0.000 claims description 3
RUVINXPYWBROJD-UHFFFAOYSA-N para-methoxyphenyl Natural products COC1=CC=C(C=CC)C=C1 RUVINXPYWBROJD-UHFFFAOYSA-N 0.000 claims description 3
NJGBTKGETPDVIK-UHFFFAOYSA-N raspberry ketone Chemical compound CC(=O)CCC1=CC=C(O)C=C1 NJGBTKGETPDVIK-UHFFFAOYSA-N 0.000 claims description 3
229940102398 methyl anthranilate Drugs 0.000 claims description 2
BPLQKQKXWHCZSS-UHFFFAOYSA-N Elemicin Chemical compound COC1=CC(CC=C)=CC(OC)=C1OC BPLQKQKXWHCZSS-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 abstract description 73
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SFEOKXHPFMOVRM-UHFFFAOYSA-N (+)-(S)-gamma-ionone Natural products CC(=O)C=CC1C(=C)CCCC1(C)C SFEOKXHPFMOVRM-UHFFFAOYSA-N 0.000 abstract description 37
MHAJPDPJQMAIIY-UHFFFAOYSA-N Hydrogen peroxide Chemical compound OO MHAJPDPJQMAIIY-UHFFFAOYSA-N 0.000 abstract description 21
235000015218 chewing gum Nutrition 0.000 abstract description 16
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150000007529 inorganic bases Chemical class 0.000 abstract description 4
XOHTWFPASNAKHB-UHFFFAOYSA-N 2-methyl-1-(6-methylcyclohexen-1-yl)propan-1-one Chemical compound CC(C)C(=O)C1=CCCCC1C XOHTWFPASNAKHB-UHFFFAOYSA-N 0.000 abstract description 3
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238000002474 experimental method Methods 0.000 description 16
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239000002904 solvent Substances 0.000 description 12
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150000002402 hexoses Chemical class 0.000 description 1
229930195733 hydrocarbon Natural products 0.000 description 1
150000002430 hydrocarbons Chemical class 0.000 description 1
239000001257 hydrogen Substances 0.000 description 1
229910052739 hydrogen Inorganic materials 0.000 description 1
125000004435 hydrogen atom Chemical group [H]* 0.000 description 1
XLYOFNOQVPJJNP-UHFFFAOYSA-M hydroxide Chemical compound [OH-] XLYOFNOQVPJJNP-UHFFFAOYSA-M 0.000 description 1
WGCNASOHLSPBMP-UHFFFAOYSA-N hydroxyacetaldehyde Natural products OCC=O WGCNASOHLSPBMP-UHFFFAOYSA-N 0.000 description 1
GFAZHVHNLUBROE-UHFFFAOYSA-N hydroxymethyl propionaldehyde Natural products CCC(=O)CO GFAZHVHNLUBROE-UHFFFAOYSA-N 0.000 description 1
238000011065 in-situ storage Methods 0.000 description 1
150000002499 ionone derivatives Chemical class 0.000 description 1
159000000014 iron salts Chemical class 0.000 description 1
WBJZTOZJJYAKHQ-UHFFFAOYSA-K iron(3+) phosphate Chemical compound [Fe+3].[O-]P([O-])([O-])=O WBJZTOZJJYAKHQ-UHFFFAOYSA-K 0.000 description 1
229910000399 iron(III) phosphate Inorganic materials 0.000 description 1
VRIVJOXICYMTAG-IYEMJOQQSA-L iron(ii) gluconate Chemical compound [Fe+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 VRIVJOXICYMTAG-IYEMJOQQSA-L 0.000 description 1
JXDYKVIHCLTXOP-UHFFFAOYSA-N isatin Chemical compound C1=CC=C2C(=O)C(=O)NC2=C1 JXDYKVIHCLTXOP-UHFFFAOYSA-N 0.000 description 1
239000004310 lactic acid Substances 0.000 description 1
235000014655 lactic acid Nutrition 0.000 description 1
230000002045 lasting effect Effects 0.000 description 1
239000010410 layer Substances 0.000 description 1
239000000787 lecithin Substances 0.000 description 1
235000010445 lecithin Nutrition 0.000 description 1
229940067606 lecithin Drugs 0.000 description 1
150000002632 lipids Chemical class 0.000 description 1
229910052943 magnesium sulfate Inorganic materials 0.000 description 1
235000019341 magnesium sulphate Nutrition 0.000 description 1
238000001819 mass spectrum Methods 0.000 description 1
229940126601 medicinal product Drugs 0.000 description 1
DILOFCBIBDMHAY-UHFFFAOYSA-N methyl 2-(3,4-dimethoxyphenyl)acetate Chemical compound COC(=O)CC1=CC=C(OC)C(OC)=C1 DILOFCBIBDMHAY-UHFFFAOYSA-N 0.000 description 1
HAFFKTJSQPQAPC-UHFFFAOYSA-N methyl 3-phenyloxirane-2-carboxylate Chemical compound COC(=O)C1OC1C1=CC=CC=C1 HAFFKTJSQPQAPC-UHFFFAOYSA-N 0.000 description 1
WBYWAXJHAXSJNI-UHFFFAOYSA-N methyl p-hydroxycinnamate Natural products OC(=O)C=CC1=CC=CC=C1 WBYWAXJHAXSJNI-UHFFFAOYSA-N 0.000 description 1
WQEPLUUGTLDZJY-UHFFFAOYSA-N n-Pentadecanoic acid Natural products CCCCCCCCCCCCCCC(O)=O WQEPLUUGTLDZJY-UHFFFAOYSA-N 0.000 description 1
YKYONYBAUNKHLG-UHFFFAOYSA-N n-Propyl acetate Natural products CCCOC(C)=O YKYONYBAUNKHLG-UHFFFAOYSA-N 0.000 description 1
UUIQMZJEGPQKFD-UHFFFAOYSA-N n-butyric acid methyl ester Natural products CCCC(=O)OC UUIQMZJEGPQKFD-UHFFFAOYSA-N 0.000 description 1
239000000025 natural resin Substances 0.000 description 1
WASNIKZYIWZQIP-AWEZNQCLSA-N nerolidol Natural products CC(=CCCC(=CCC[C@@H](O)C=C)C)C WASNIKZYIWZQIP-AWEZNQCLSA-N 0.000 description 1
230000003472 neutralizing effect Effects 0.000 description 1
SJYNFBVQFBRSIB-UHFFFAOYSA-N norbornadiene Chemical compound C1=CC2C=CC1C2 SJYNFBVQFBRSIB-UHFFFAOYSA-N 0.000 description 1
235000016709 nutrition Nutrition 0.000 description 1
150000007823 ocimene derivatives Chemical class 0.000 description 1
150000007524 organic acids Chemical class 0.000 description 1
235000005985 organic acids Nutrition 0.000 description 1
239000012044 organic layer Substances 0.000 description 1
239000003960 organic solvent Substances 0.000 description 1
150000002924 oxiranes Chemical class 0.000 description 1
239000001301 oxygen Substances 0.000 description 1
229910052760 oxygen Inorganic materials 0.000 description 1
239000005022 packaging material Substances 0.000 description 1
QNGNSVIICDLXHT-UHFFFAOYSA-N para-ethylbenzaldehyde Natural products CCC1=CC=C(C=O)C=C1 QNGNSVIICDLXHT-UHFFFAOYSA-N 0.000 description 1
239000002245 particle Substances 0.000 description 1
239000001814 pectin Substances 0.000 description 1
235000010987 pectin Nutrition 0.000 description 1
229920001277 pectin Polymers 0.000 description 1
LHTVMBMETNGEAN-UHFFFAOYSA-N pent-1-en-1-ol Chemical compound CCCC=CO LHTVMBMETNGEAN-UHFFFAOYSA-N 0.000 description 1
150000002972 pentoses Chemical class 0.000 description 1
238000005502 peroxidation Methods 0.000 description 1
WVDDGKGOMKODPV-ZQBYOMGUSA-N phenyl(114C)methanol Chemical compound O[14CH2]C1=CC=CC=C1 WVDDGKGOMKODPV-ZQBYOMGUSA-N 0.000 description 1
230000000704 physical effect Effects 0.000 description 1
239000004033 plastic Substances 0.000 description 1
229920003023 plastic Polymers 0.000 description 1
239000004014 plasticizer Substances 0.000 description 1
229940114930 potassium stearate Drugs 0.000 description 1
ANBFRLKBEIFNQU-UHFFFAOYSA-M potassium;octadecanoate Chemical compound [K+].CCCCCCCCCCCCCCCCCC([O-])=O ANBFRLKBEIFNQU-UHFFFAOYSA-M 0.000 description 1
239000003755 preservative agent Substances 0.000 description 1
229940090181 propyl acetate Drugs 0.000 description 1
239000000473 propyl gallate Substances 0.000 description 1
235000010388 propyl gallate Nutrition 0.000 description 1
229940075579 propyl gallate Drugs 0.000 description 1
239000012521 purified sample Substances 0.000 description 1
235000020095 red wine Nutrition 0.000 description 1
229960002477 riboflavin Drugs 0.000 description 1
235000019192 riboflavin Nutrition 0.000 description 1
239000002151 riboflavin Substances 0.000 description 1
IOVGROKTTNBUGK-SJCJKPOMSA-N ritodrine Chemical compound N([C@@H](C)[C@H](O)C=1C=CC(O)=CC=1)CCC1=CC=C(O)C=C1 IOVGROKTTNBUGK-SJCJKPOMSA-N 0.000 description 1
CVHZOJJKTDOEJC-UHFFFAOYSA-N saccharin Chemical compound C1=CC=C2C(=O)NS(=O)(=O)C2=C1 CVHZOJJKTDOEJC-UHFFFAOYSA-N 0.000 description 1
229940081974 saccharin Drugs 0.000 description 1
235000019204 saccharin Nutrition 0.000 description 1
239000000901 saccharin and its Na,K and Ca salt Substances 0.000 description 1
239000010671 sandalwood oil Substances 0.000 description 1
239000012047 saturated solution Substances 0.000 description 1
230000001953 sensory effect Effects 0.000 description 1
239000003352 sequestering agent Substances 0.000 description 1
239000000377 silicon dioxide Substances 0.000 description 1
235000020183 skimmed milk Nutrition 0.000 description 1
235000011888 snacks Nutrition 0.000 description 1
GJPYYNMJTJNYTO-UHFFFAOYSA-J sodium aluminium sulfate Chemical compound [Na+].[Al+3].[O-]S([O-])(=O)=O.[O-]S([O-])(=O)=O GJPYYNMJTJNYTO-UHFFFAOYSA-J 0.000 description 1
229910000029 sodium carbonate Inorganic materials 0.000 description 1
UKLNMMHNWFDKNT-UHFFFAOYSA-M sodium chlorite Chemical compound [Na+].[O-]Cl=O UKLNMMHNWFDKNT-UHFFFAOYSA-M 0.000 description 1
229960002218 sodium chlorite Drugs 0.000 description 1
SUKJFIGYRHOWBL-UHFFFAOYSA-N sodium hypochlorite Chemical compound [Na+].Cl[O-] SUKJFIGYRHOWBL-UHFFFAOYSA-N 0.000 description 1
235000014214 soft drink Nutrition 0.000 description 1
239000008247 solid mixture Substances 0.000 description 1
239000001587 sorbitan monostearate Substances 0.000 description 1
235000011076 sorbitan monostearate Nutrition 0.000 description 1
229940035048 sorbitan monostearate Drugs 0.000 description 1
235000014347 soups Nutrition 0.000 description 1
238000001228 spectrum Methods 0.000 description 1
238000005507 spraying Methods 0.000 description 1
238000010561 standard procedure Methods 0.000 description 1
239000012258 stirred mixture Substances 0.000 description 1
239000004575 stone Substances 0.000 description 1
238000006467 substitution reaction Methods 0.000 description 1
229940014800 succinic anhydride Drugs 0.000 description 1
150000008163 sugars Chemical class 0.000 description 1
230000001502 supplementing effect Effects 0.000 description 1
239000000375 suspending agent Substances 0.000 description 1
238000013268 sustained release Methods 0.000 description 1
239000012730 sustained-release form Substances 0.000 description 1
239000003765 sweetening agent Substances 0.000 description 1
229920002994 synthetic fiber Polymers 0.000 description 1
229920003002 synthetic resin Polymers 0.000 description 1
239000000057 synthetic resin Substances 0.000 description 1
239000003760 tallow Substances 0.000 description 1
230000009967 tasteless effect Effects 0.000 description 1
238000012360 testing method Methods 0.000 description 1
VZGDMQKNWNREIO-UHFFFAOYSA-N tetrachloromethane Chemical compound ClC(Cl)(Cl)Cl VZGDMQKNWNREIO-UHFFFAOYSA-N 0.000 description 1
150000003568 thioethers Chemical class 0.000 description 1
230000009974 thixotropic effect Effects 0.000 description 1
UAXOELSVPTZZQG-UHFFFAOYSA-N tiglic acid Natural products CC(C)=C(C)C(O)=O UAXOELSVPTZZQG-UHFFFAOYSA-N 0.000 description 1
XJPBRODHZKDRCB-UHFFFAOYSA-N trans-alpha-ocimene Natural products CC(=C)CCC=C(C)C=C XJPBRODHZKDRCB-UHFFFAOYSA-N 0.000 description 1
HRHOWZHRCRZVCU-UHFFFAOYSA-N trans-hex-2-enyl acetate Natural products CCCC=CCOC(C)=O HRHOWZHRCRZVCU-UHFFFAOYSA-N 0.000 description 1
ZFDIRQKJPRINOQ-UHFFFAOYSA-N transbutenic acid ethyl ester Natural products CCOC(=O)C=CC ZFDIRQKJPRINOQ-UHFFFAOYSA-N 0.000 description 1
QORWJWZARLRLPR-UHFFFAOYSA-H tricalcium bis(phosphate) Chemical compound [Ca+2].[Ca+2].[Ca+2].[O-]P([O-])([O-])=O.[O-]P([O-])([O-])=O QORWJWZARLRLPR-UHFFFAOYSA-H 0.000 description 1
235000019731 tricalcium phosphate Nutrition 0.000 description 1
229940005605 valeric acid Drugs 0.000 description 1
235000015112 vegetable and seed oil Nutrition 0.000 description 1
235000013311 vegetables Nutrition 0.000 description 1
229920001567 vinyl ester resin Polymers 0.000 description 1
229940088594 vitamin Drugs 0.000 description 1
235000013343 vitamin Nutrition 0.000 description 1
239000011782 vitamin Substances 0.000 description 1
229930003231 vitamin Natural products 0.000 description 1
239000001993 wax Substances 0.000 description 1
239000011701 zinc Substances 0.000 description 1
229910052725 zinc Inorganic materials 0.000 description 1
235000016804 zinc Nutrition 0.000 description 1
239000011592 zinc chloride Substances 0.000 description 1
235000005074 zinc chloride Nutrition 0.000 description 1
NWONKYPBYAMBJT-UHFFFAOYSA-L zinc sulfate Chemical compound [Zn+2].[O-]S([O-])(=O)=O NWONKYPBYAMBJT-UHFFFAOYSA-L 0.000 description 1
229960001763 zinc sulfate Drugs 0.000 description 1
229910000368 zinc sulfate Inorganic materials 0.000 description 1

Classifications

- A—HUMAN NECESSITIES
- A23—FOODS OR FOODSTUFFS; TREATMENT THEREOF, NOT COVERED BY OTHER CLASSES
- A23G—COCOA; COCOA PRODUCTS, e.g. CHOCOLATE; SUBSTITUTES FOR COCOA OR COCOA PRODUCTS; CONFECTIONERY; CHEWING GUM; ICE-CREAM; PREPARATION THEREOF
- A23G4/00—Chewing gum
- A23G4/06—Chewing gum characterised by the composition containing organic or inorganic compounds
- A—HUMAN NECESSITIES
- A23—FOODS OR FOODSTUFFS; TREATMENT THEREOF, NOT COVERED BY OTHER CLASSES
- A23G—COCOA; COCOA PRODUCTS, e.g. CHOCOLATE; SUBSTITUTES FOR COCOA OR COCOA PRODUCTS; CONFECTIONERY; CHEWING GUM; ICE-CREAM; PREPARATION THEREOF
- A23G4/00—Chewing gum
- A23G4/06—Chewing gum characterised by the composition containing organic or inorganic compounds
- A23G4/064—Chewing gum characterised by the composition containing organic or inorganic compounds containing inorganic compounds
- 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
- A23L27/20—Synthetic spices, flavouring agents or condiments
- 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
- A23L27/20—Synthetic spices, flavouring agents or condiments
- A23L27/203—Alicyclic compounds
- 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
- A23L27/20—Synthetic spices, flavouring agents or condiments
- A23L27/204—Aromatic compounds
- A—HUMAN NECESSITIES
- A24—TOBACCO; CIGARS; CIGARETTES; SIMULATED SMOKING DEVICES; SMOKERS' REQUISITES
- A24B—MANUFACTURE OR PREPARATION OF TOBACCO FOR SMOKING OR CHEWING; TOBACCO; SNUFF
- A24B15/00—Chemical features or treatment of tobacco; Tobacco substitutes, e.g. in liquid form
- A24B15/18—Treatment of tobacco products or tobacco substitutes
- A24B15/28—Treatment of tobacco products or tobacco substitutes by chemical substances
- A24B15/30—Treatment of tobacco products or tobacco substitutes by chemical substances by organic substances
- A24B15/34—Treatment of tobacco products or tobacco substitutes by chemical substances by organic substances containing a carbocyclic ring other than a six-membered aromatic ring
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C45/00—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds
- C07C45/51—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by pyrolysis, rearrangement or decomposition
- C07C45/54—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by pyrolysis, rearrangement or decomposition of compounds containing doubly bound oxygen atoms, e.g. esters
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D303/00—Compounds containing three-membered rings having one oxygen atom as the only ring hetero atom
- C07D303/02—Compounds containing oxirane rings
- C07D303/12—Compounds containing oxirane rings with hydrocarbon radicals, substituted by singly or doubly bound oxygen atoms
- C07D303/32—Compounds containing oxirane rings with hydrocarbon radicals, substituted by singly or doubly bound oxygen atoms by aldehydo- or ketonic radicals
- 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
- C11B9/0026—Essential oils; Perfumes compounds containing an alicyclic ring not condensed with another ring
- C11B9/0034—Essential oils; Perfumes compounds containing an alicyclic ring not condensed with another ring the ring containing six carbon atoms
- 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
- C11B9/0061—Essential oils; Perfumes compounds containing a six-membered aromatic ring not condensed with another ring
- C—CHEMISTRY; METALLURGY
- C11—ANIMAL OR VEGETABLE OILS, FATS, FATTY SUBSTANCES OR WAXES; FATTY ACIDS THEREFROM; DETERGENTS; CANDLES
- C11D—DETERGENT COMPOSITIONS; USE OF SINGLE SUBSTANCES AS DETERGENTS; SOAP OR SOAP-MAKING; RESIN SOAPS; RECOVERY OF GLYCEROL
- C11D3/00—Other compounding ingredients of detergent compositions covered in group C11D1/00
- C11D3/0005—Other compounding ingredients characterised by their effect
- C11D3/0084—Antioxidants; Free-radical scavengers

Landscapes

Chemical & Material Sciences (AREA)
Organic Chemistry (AREA)
Life Sciences & Earth Sciences (AREA)
Engineering & Computer Science (AREA)
Food Science & Technology (AREA)
Polymers & Plastics (AREA)
Chemical Kinetics & Catalysis (AREA)
Health & Medical Sciences (AREA)
Wood Science & Technology (AREA)
Oil, Petroleum & Natural Gas (AREA)
Nutrition Science (AREA)
Inorganic Chemistry (AREA)
General Health & Medical Sciences (AREA)
Toxicology (AREA)
General Chemical & Material Sciences (AREA)
Biochemistry (AREA)
Fats And Perfumes (AREA)
Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Manufacture Of Tobacco Products (AREA)
Detergent Compositions (AREA)
Confectionery (AREA)
Alcoholic Beverages (AREA)
Cosmetics (AREA)
Seasonings (AREA)
Distillation Of Fermentation Liquor, Processing Of Alcohols, Vinegar And Beer (AREA)

CA234,735A 1974-09-19 1975-09-03 Saveurs et aromes contenant un acetaldehyde substitue en alpha, seul ou combine avec une cetone, et methodes pour alterer ou renforcer a l'aide de ces produits les proprietes organoleptiques de produits de consommation Expired CA1062904A (fr)

Applications Claiming Priority (6)

Application Number	Priority Date	Filing Date	Title
US05/507,412 US3940499A (en)	1974-09-19	1974-09-19	Food or flavor containing 2,6,6-trimethyl-1-cyclohexen-1-ylacetaldehyde
US05/507,414 US3956393A (en)	1974-09-19	1974-09-19	Process for preparing alpha-substituted acetaldehydes
US05/598,652 US4014351A (en)	1974-09-19	1975-07-24	Novel tobacco flavoring and aroma compositions and tobaccos containing alpha-substituted acetaldehyde
US05/598,805 US4026824A (en)	1974-09-19	1975-07-24	2,6,6-Trimethyl-1-cyclohexen-1-ylacetaldehyde fragrance composition
US05/598,654 US3959508A (en)	1974-09-19	1975-07-24	Flavoring compositions containing mixture of 2,2,6-trimethyl-1-cyclohexen-1-ylacetaldehyde and 2,6,6-trimethyl-1-crotonyl-1,3-cyclohexadiene
US05/601,727 US4028279A (en)	1975-08-04	1975-08-04	Novel fragrance compositions containing 2,6,6 trimethyl-1-cyclohexen-1-yl acetaldehyde and phenyl C6 ketone

Publications (1)

Publication Number	Publication Date
CA1062904A true CA1062904A (fr)	1979-09-25

Family

ID=27560078

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
CA234,735A Expired CA1062904A (fr)	1974-09-19	1975-09-03	Saveurs et aromes contenant un acetaldehyde substitue en alpha, seul ou combine avec une cetone, et methodes pour alterer ou renforcer a l'aide de ces produits les proprietes organoleptiques de produits de consommation

Country Status (7)

Country	Link
JP (2)	JPS51125777A (fr)
CA (1)	CA1062904A (fr)
CH (1)	CH621928A5 (fr)
DE (1)	DE2540624C3 (fr)
FR (1)	FR2330333A1 (fr)
GB (1)	GB1530465A (fr)
NL (1)	NL164265C (fr)

Families Citing this family (13)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
FI780439A7 (fi)	1978-01-12	1979-07-13	Unilever Nv	Tvaettmedel
FI780440A7 (fi)	1978-01-12	1979-07-13	Unilever Nv	Detergentkomposition
US4288341A (en)	1978-03-20	1981-09-08	Lever Brothers Company	Detergent product containing deodorant compositions
JPS595109A (ja) *	1982-06-30	1984-01-12	Lion Corp	口腔用組成物
JPH085772B2 (ja) *	1986-02-05	1996-01-24	ライオン株式会社	口腔用組成物
US6150409A (en) *	1998-10-23	2000-11-21	Monell Chemical Senses Center	Adjuvants and methods for raising intracellular calcium ion concentration
DE10348062A1 (de) *	2003-10-16	2005-05-19	Symrise Gmbh & Co. Kg	Kurzkettige Enolester als Riechstoff-Prekursoren
JP2008514573A (ja) *	2004-09-24	2008-05-08	シムライズ・ゲゼルシヤフト・ミツト・ベシユレンクテル・ハフツング・ウント・コンパニー・コマンジツト・ゲゼルシヤフト	口臭に対する作用物質としての芳香物質混合物の使用
WO2006032667A1 (fr) *	2004-09-24	2006-03-30	Symrise Gmbh & Co. Kg	Utilisation de bêta-homocyclocitral comme agent contre la mauvaise haleine
US7902404B2 (en)	2005-09-13	2011-03-08	Takasago International Corporation	Method for producing optically active α-ionone
JP5989301B2 (ja) *	2011-01-12	2016-09-07	キッコーマン株式会社	調味料
CN114947175A (zh) *	2016-11-04	2022-08-30	尼科创业贸易有限公司	可用于模拟烟草香味的组合物
JP7790913B2 (ja) *	2021-10-18	2025-12-23	サンスター株式会社	口腔用組成物、及び金属味と基剤臭とを抑制する方法

1975
- 1975-09-03 CA CA234,735A patent/CA1062904A/fr not_active Expired
- 1975-09-12 DE DE2540624A patent/DE2540624C3/de not_active Expired
- 1975-09-17 NL NL7510914.A patent/NL164265C/xx not_active IP Right Cessation
- 1975-09-17 JP JP11312275A patent/JPS51125777A/ja active Granted
- 1975-09-18 CH CH1213475A patent/CH621928A5/de not_active IP Right Cessation
- 1975-09-18 FR FR7528608A patent/FR2330333A1/fr active Granted
- 1975-09-19 GB GB38490/75A patent/GB1530465A/en not_active Expired
1977
- 1977-07-15 JP JP8554177A patent/JPS5384944A/ja active Granted

Also Published As

Publication number	Publication date
FR2330333B1 (fr)	1978-10-13
NL164265B (nl)	1980-07-15
AU8474075A (en)	1976-11-25
GB1530465A (en)	1978-11-01
CH621928A5 (en)	1981-03-13
DE2540624B2 (de)	1977-12-15
NL164265C (nl)	1980-12-15
JPS51125777A (en)	1976-11-02
DE2540624C3 (de)	1978-08-17
FR2330333A1 (fr)	1977-06-03
DE2540624A1 (de)	1976-04-08
JPS5625215B2 (fr)	1981-06-11
JPS5318590B2 (fr)	1978-06-15
NL7510914A (nl)	1976-03-23
JPS5384944A (en)	1978-07-26

Publication	Publication Date	Title
US4334098A (en)	1982-06-08	Trans,trans-Δ-damascone, mixtures containing major proportions of same, processes for preparing same and organoleptic uses thereof
US4154693A (en)	1979-05-15	1-[3-(Methylthio)butyryl]-2,6,6-trimethyl-cyclohexene or 1,3-cyclohexadiene analog are used in detergent and soap compositions
EP0047572B1 (fr)	1984-07-11	Cétones à chaîne ramifiée, procédé pour la modification, augmentation ou accentuation organoleptique à l'aide de ces cétones et procédé pour la fabrication d'une solution stable en une phase d'hypochlorite de métal alcalin contenant ces cétones
US3959508A (en)	1976-05-25	Flavoring compositions containing mixture of 2,2,6-trimethyl-1-cyclohexen-1-ylacetaldehyde and 2,6,6-trimethyl-1-crotonyl-1,3-cyclohexadiene
US3940499A (en)	1976-02-24	Food or flavor containing 2,6,6-trimethyl-1-cyclohexen-1-ylacetaldehyde
CA1062904A (fr)	1979-09-25	Saveurs et aromes contenant un acetaldehyde substitue en alpha, seul ou combine avec une cetone, et methodes pour alterer ou renforcer a l'aide de ces produits les proprietes organoleptiques de produits de consommation
US4000329A (en)	1976-12-28	Flavoring compositions and foods containing one or more alkyl side chain methyl substituted or unsubstituted 2,2,6-trimethyl-1-cyclohexen-1-vinyl alkanoates
US4515987A (en)	1985-05-07	Process for preparing a methoxybenzaldehyde from the corresponding phenolic benzaldehyde
US4198309A (en)	1980-04-15	Use of trans, trans-Δ-damascone and mixtures containing 80% or more of trans, trans-Δ-damascone in augmenting or enhancing the aroma of a detergent
US4084009A (en)	1978-04-11	Flavoring with a hydroxy cyclohexenone derivative
US4242281A (en)	1980-12-30	Process for preparing 6-hydroxy-2,6-dimethylheptanal and intermediates thereof
US4069828A (en)	1978-01-24	Flavored tobacco article
US4458699A (en)	1984-07-10	Uses of methyl phenyl pentanol derivatives in augmenting or enhancing the aroma or taste of smoking tobacco and smoking tobacco articles
US4324704A (en)	1982-04-13	Process for hydrogenation of damascenone, products produced thereby and organoleptic uses of said products
US4517990A (en)	1985-05-21	3,4,5,6,6-Pentamethyl hexanol-2 and alkyl homologues thereof; process for preparing same and organoleptic uses thereof
EP0012436B1 (fr)	1982-11-24	Procédé d'hydrogénation de dérivés 2,6,6-triméthylcyclohexéniques, composés obtenus selon ce procédé et applications organoleptiques de ces composés
US4209025A (en)	1980-06-24	Process for augmenting or enhancing the flavor of tobacco using 1-(3-methylthio)butyryl)-2,6,6-trimethyl-cyclohexene and the 1,3-cyclohexadiene analog thereof
US4430354A (en)	1984-02-07	Flavoring with heliotropyl methyl carbonate
US4094823A (en)	1978-06-13	Ethyl-2-methyl-3,4-pentadienoate perfume compositions
US4000090A (en)	1976-12-28	Enol esters of an alpha substituted acetaldehyde fragrance compositions
US4048201A (en)	1977-09-13	Novel enol esters
US4448713A (en)	1984-05-15	Branched ketones, organoleptic uses thereof and process for preparing same
US4380674A (en)	1983-04-19	Branched ketones, organoleptic uses thereof and process for preparing same
US4014351A (en)	1977-03-29	Novel tobacco flavoring and aroma compositions and tobaccos containing alpha-substituted acetaldehyde
US4157350A (en)	1979-06-05	Process for preparing 1-(2,6,6-trimethyl-1,3-cyclohexadien-1-yl)-1,3-butanedione and intermediates