JPH0368851B2 - - Google Patents

Info

Publication number: JPH0368851B2
Authority: JP; Japan
Prior art keywords: cis; alkyl group; acid; formula; aroma
Prior art date: 1983-07-27
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 - Lifetime

Application number

JP58135686A

Other languages

English (en)

Japanese (ja)

Other versions

JPS6028950A (ja

Inventor

Akemichi Furuhata

Ken Oonishi

Kunio Kojo

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.)

T Hasegawa Co Ltd

Original Assignee

T Hasegawa Co Ltd

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.)

1983-07-27

Filing date

1983-07-27

Publication date

1991-10-30

1983-07-27 Application filed by T Hasegawa Co Ltd filed Critical T Hasegawa Co Ltd

1983-07-27 Priority to JP58135686A priority Critical patent/JPS6028950A/ja

1985-02-14 Publication of JPS6028950A publication Critical patent/JPS6028950A/ja

1991-10-30 Publication of JPH0368851B2 publication Critical patent/JPH0368851B2/ja

Status Granted legal-status Critical Current

Links

150000001875 compounds Chemical class 0.000 claims description 26
125000000217 alkyl group Chemical group 0.000 claims description 21
239000002253 acid Substances 0.000 claims description 20
150000007513 acids Chemical class 0.000 claims description 14
238000004519 manufacturing process Methods 0.000 claims description 7
125000006273 (C1-C3) alkyl group Chemical group 0.000 claims description 6
125000004169 (C1-C6) alkyl group Chemical group 0.000 claims description 6
238000006317 isomerization reaction Methods 0.000 claims description 4
-1 Organic Reactions Chemical class 0.000 description 31
239000000796 flavoring agent Substances 0.000 description 27
239000000203 mixture Substances 0.000 description 27
235000019634 flavors Nutrition 0.000 description 26
239000003205 fragrance Substances 0.000 description 19
RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 17
238000006243 chemical reaction Methods 0.000 description 11
239000003795 chemical substances by application Substances 0.000 description 11
YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 9
GNOIPBMMFNIUFM-UHFFFAOYSA-N hexamethylphosphoric triamide Chemical compound CN(C)P(=O)(N(C)C)N(C)C GNOIPBMMFNIUFM-UHFFFAOYSA-N 0.000 description 9
VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 9
238000005481 NMR spectroscopy Methods 0.000 description 8
239000002537 cosmetic Substances 0.000 description 8
230000002688 persistence Effects 0.000 description 8
XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 6
MUBZPKHOEPUJKR-UHFFFAOYSA-N Oxalic acid Chemical compound OC(=O)C(O)=O MUBZPKHOEPUJKR-UHFFFAOYSA-N 0.000 description 6
QUKGYYKBILRGFE-UHFFFAOYSA-N benzyl acetate Chemical compound CC(=O)OCC1=CC=CC=C1 QUKGYYKBILRGFE-UHFFFAOYSA-N 0.000 description 6
238000009835 boiling Methods 0.000 description 6
UAOMVDZJSHZZME-UHFFFAOYSA-N diisopropylamine Chemical compound CC(C)NC(C)C UAOMVDZJSHZZME-UHFFFAOYSA-N 0.000 description 6
235000013305 food Nutrition 0.000 description 6
CDOSHBSSFJOMGT-UHFFFAOYSA-N linalool Chemical compound CC(C)=CCCC(C)(O)C=C CDOSHBSSFJOMGT-UHFFFAOYSA-N 0.000 description 6
230000005923 long-lasting effect Effects 0.000 description 6
UNWHQJYQXFOWLI-PLNGDYQASA-N (z)-2,5-dimethylhex-3-enoic acid Chemical compound CC(C)\C=C/C(C)C(O)=O UNWHQJYQXFOWLI-PLNGDYQASA-N 0.000 description 5
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 5
239000012300 argon atmosphere Substances 0.000 description 5
239000002585 base Substances 0.000 description 5
239000003599 detergent Substances 0.000 description 5
239000003814 drug Substances 0.000 description 5
238000002156 mixing Methods 0.000 description 5
230000002085 persistent effect Effects 0.000 description 5
NIONDZDPPYHYKY-SNAWJCMRSA-N (2E)-hexenoic acid Chemical compound CCC\C=C\C(O)=O NIONDZDPPYHYKY-SNAWJCMRSA-N 0.000 description 4
WRMNZCZEMHIOCP-UHFFFAOYSA-N 2-phenylethanol Chemical compound OCCC1=CC=CC=C1 WRMNZCZEMHIOCP-UHFFFAOYSA-N 0.000 description 4
WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 4
239000004480 active ingredient Substances 0.000 description 4
150000001339 alkali metal compounds Chemical class 0.000 description 4
QMVPMAAFGQKVCJ-UHFFFAOYSA-N citronellol Chemical compound OCCC(C)CCC=C(C)C QMVPMAAFGQKVCJ-UHFFFAOYSA-N 0.000 description 4
MLFHJEHSLIIPHL-UHFFFAOYSA-N isoamyl acetate Chemical compound CC(C)CCOC(C)=O MLFHJEHSLIIPHL-UHFFFAOYSA-N 0.000 description 4
125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 4
239000003960 organic solvent Substances 0.000 description 4
239000000047 product Substances 0.000 description 4
239000000341 volatile oil Substances 0.000 description 4
239000001490 (3R)-3,7-dimethylocta-1,6-dien-3-ol Substances 0.000 description 3
CDOSHBSSFJOMGT-JTQLQIEISA-N (R)-linalool Natural products CC(C)=CCC[C@@](C)(O)C=C CDOSHBSSFJOMGT-JTQLQIEISA-N 0.000 description 3
HNAGHMKIPMKKBB-UHFFFAOYSA-N 1-benzylpyrrolidine-3-carboxamide Chemical compound C1C(C(=O)N)CCN1CC1=CC=CC=C1 HNAGHMKIPMKKBB-UHFFFAOYSA-N 0.000 description 3
244000099147 Ananas comosus Species 0.000 description 3
235000007119 Ananas comosus Nutrition 0.000 description 3
WVDDGKGOMKODPV-UHFFFAOYSA-N Benzyl alcohol Chemical compound OCC1=CC=CC=C1 WVDDGKGOMKODPV-UHFFFAOYSA-N 0.000 description 3
VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 3
229940007550 benzyl acetate Drugs 0.000 description 3
235000013361 beverage Nutrition 0.000 description 3
OBNCKNCVKJNDBV-UHFFFAOYSA-N butanoic acid ethyl ester Natural products CCCC(=O)OCC OBNCKNCVKJNDBV-UHFFFAOYSA-N 0.000 description 3
239000003054 catalyst Substances 0.000 description 3
235000009508 confectionery Nutrition 0.000 description 3
239000004615 ingredient Substances 0.000 description 3
229930007744 linalool Natural products 0.000 description 3
125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 3
SATCULPHIDQDRE-UHFFFAOYSA-N piperonal Chemical compound O=CC1=CC=C2OCOC2=C1 SATCULPHIDQDRE-UHFFFAOYSA-N 0.000 description 3
235000014347 soups Nutrition 0.000 description 3
OOCCDEMITAIZTP-QPJJXVBHSA-N (E)-cinnamyl alcohol Chemical compound OC\C=C\C1=CC=CC=C1 OOCCDEMITAIZTP-QPJJXVBHSA-N 0.000 description 2
QMVPMAAFGQKVCJ-SNVBAGLBSA-N (R)-(+)-citronellol Natural products OCC[C@H](C)CCC=C(C)C QMVPMAAFGQKVCJ-SNVBAGLBSA-N 0.000 description 2
XTQLWNAWEPKOLB-PLNGDYQASA-N (z)-2-methylhex-3-enoic acid Chemical compound CC\C=C/C(C)C(O)=O XTQLWNAWEPKOLB-PLNGDYQASA-N 0.000 description 2
WTMAHJABDOHPDJ-HYXAFXHYSA-N 2-n-Propyl-3-pentenoic acid Chemical compound CCCC(C(O)=O)\C=C/C WTMAHJABDOHPDJ-HYXAFXHYSA-N 0.000 description 2
UBLAMKHIFZBBSS-UHFFFAOYSA-N 3-Methylbutyl pentanoate Chemical compound CCCCC(=O)OCCC(C)C UBLAMKHIFZBBSS-UHFFFAOYSA-N 0.000 description 2
XPCTZQVDEJYUGT-UHFFFAOYSA-N 3-hydroxy-2-methyl-4-pyrone Chemical compound CC=1OC=CC(=O)C=1O XPCTZQVDEJYUGT-UHFFFAOYSA-N 0.000 description 2
OALYTRUKMRCXNH-UHFFFAOYSA-N 5-pentyloxolan-2-one Chemical compound CCCCCC1CCC(=O)O1 OALYTRUKMRCXNH-UHFFFAOYSA-N 0.000 description 2
XKRFYHLGVUSROY-UHFFFAOYSA-N Argon Chemical compound [Ar] XKRFYHLGVUSROY-UHFFFAOYSA-N 0.000 description 2
240000007436 Cananga odorata Species 0.000 description 2
235000005979 Citrus limon Nutrition 0.000 description 2
244000131522 Citrus pyriformis Species 0.000 description 2
240000000560 Citrus x paradisi Species 0.000 description 2
XTHFKEDIFFGKHM-UHFFFAOYSA-N Dimethoxyethane Chemical compound COCCOC XTHFKEDIFFGKHM-UHFFFAOYSA-N 0.000 description 2
GLZPCOQZEFWAFX-UHFFFAOYSA-N Geraniol Chemical compound CC(C)=CCCC(C)=CCO GLZPCOQZEFWAFX-UHFFFAOYSA-N 0.000 description 2
OFOBLEOULBTSOW-UHFFFAOYSA-N Malonic acid Chemical compound OC(=O)CC(O)=O OFOBLEOULBTSOW-UHFFFAOYSA-N 0.000 description 2
244000070406 Malus silvestris Species 0.000 description 2
LRHPLDYGYMQRHN-UHFFFAOYSA-N N-Butanol Chemical compound CCCCO LRHPLDYGYMQRHN-UHFFFAOYSA-N 0.000 description 2
MZRVEZGGRBJDDB-UHFFFAOYSA-N N-Butyllithium Chemical compound [Li]CCCC MZRVEZGGRBJDDB-UHFFFAOYSA-N 0.000 description 2
241000234479 Narcissus Species 0.000 description 2
JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 2
244000269722 Thea sinensis Species 0.000 description 2
OOCCDEMITAIZTP-UHFFFAOYSA-N allylic benzylic alcohol Natural products OCC=CC1=CC=CC=C1 OOCCDEMITAIZTP-UHFFFAOYSA-N 0.000 description 2
IGODOXYLBBXFDW-UHFFFAOYSA-N alpha-Terpinyl acetate Chemical compound CC(=O)OC(C)(C)C1CCC(C)=CC1 IGODOXYLBBXFDW-UHFFFAOYSA-N 0.000 description 2
WUOACPNHFRMFPN-UHFFFAOYSA-N alpha-terpineol Chemical compound CC1=CCC(C(C)(C)O)CC1 WUOACPNHFRMFPN-UHFFFAOYSA-N 0.000 description 2
235000019568 aromas Nutrition 0.000 description 2
HUMNYLRZRPPJDN-UHFFFAOYSA-N benzaldehyde Chemical compound O=CC1=CC=CC=C1 HUMNYLRZRPPJDN-UHFFFAOYSA-N 0.000 description 2
JGQFVRIQXUFPAH-UHFFFAOYSA-N beta-citronellol Natural products OCCC(C)CCCC(C)=C JGQFVRIQXUFPAH-UHFFFAOYSA-N 0.000 description 2
XUPYJHCZDLZNFP-UHFFFAOYSA-N butyl butanoate Chemical compound CCCCOC(=O)CCC XUPYJHCZDLZNFP-UHFFFAOYSA-N 0.000 description 2
235000000484 citronellol Nutrition 0.000 description 2
SQIFACVGCPWBQZ-UHFFFAOYSA-N delta-terpineol Natural products CC(C)(O)C1CCC(=C)CC1 SQIFACVGCPWBQZ-UHFFFAOYSA-N 0.000 description 2
229940043279 diisopropylamine Drugs 0.000 description 2
235000019441 ethanol Nutrition 0.000 description 2
125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 2
SHZIWNPUGXLXDT-UHFFFAOYSA-N ethyl hexanoate Chemical compound CCCCCC(=O)OCC SHZIWNPUGXLXDT-UHFFFAOYSA-N 0.000 description 2
PPXUHEORWJQRHJ-UHFFFAOYSA-N ethyl isovalerate Chemical compound CCOC(=O)CC(C)C PPXUHEORWJQRHJ-UHFFFAOYSA-N 0.000 description 2
FKRCODPIKNYEAC-UHFFFAOYSA-N ethyl propionate Chemical compound CCOC(=O)CC FKRCODPIKNYEAC-UHFFFAOYSA-N 0.000 description 2
RRAFCDWBNXTKKO-UHFFFAOYSA-N eugenol Chemical compound COC1=CC(CC=C)=CC=C1O RRAFCDWBNXTKKO-UHFFFAOYSA-N 0.000 description 2
229940117955 isoamyl acetate Drugs 0.000 description 2
XAOGXQMKWQFZEM-UHFFFAOYSA-N isoamyl propanoate Chemical compound CCC(=O)OCCC(C)C XAOGXQMKWQFZEM-UHFFFAOYSA-N 0.000 description 2
PHTQWCKDNZKARW-UHFFFAOYSA-N isoamylol Chemical compound CC(C)CCO PHTQWCKDNZKARW-UHFFFAOYSA-N 0.000 description 2
UWKAYLJWKGQEPM-LBPRGKRZSA-N linalyl acetate Chemical compound CC(C)=CCC[C@](C)(C=C)OC(C)=O UWKAYLJWKGQEPM-LBPRGKRZSA-N 0.000 description 2
QCYIFDAFIXZTQO-UHFFFAOYSA-N lithium;diphenylmethylbenzene Chemical compound [Li+].C1=CC=CC=C1[C-](C=1C=CC=CC=1)C1=CC=CC=C1 QCYIFDAFIXZTQO-UHFFFAOYSA-N 0.000 description 2
OVEHNNQXLPJPPL-UHFFFAOYSA-N lithium;n-propan-2-ylpropan-2-amine Chemical compound [Li].CC(C)NC(C)C OVEHNNQXLPJPPL-UHFFFAOYSA-N 0.000 description 2
239000012299 nitrogen atmosphere Substances 0.000 description 2
239000003921 oil Substances 0.000 description 2
235000019198 oils Nutrition 0.000 description 2
235000006408 oxalic acid Nutrition 0.000 description 2
ZRSNZINYAWTAHE-UHFFFAOYSA-N p-methoxybenzaldehyde Chemical compound COC1=CC=C(C=O)C=C1 ZRSNZINYAWTAHE-UHFFFAOYSA-N 0.000 description 2
CFNJLPHOBMVMNS-UHFFFAOYSA-N pentyl butyrate Chemical compound CCCCCOC(=O)CCC CFNJLPHOBMVMNS-UHFFFAOYSA-N 0.000 description 2
239000000825 pharmaceutical preparation Substances 0.000 description 2
229940127557 pharmaceutical product Drugs 0.000 description 2
MDHYEMXUFSJLGV-UHFFFAOYSA-N phenethyl acetate Chemical compound CC(=O)OCCC1=CC=CC=C1 MDHYEMXUFSJLGV-UHFFFAOYSA-N 0.000 description 2
229940067107 phenylethyl alcohol Drugs 0.000 description 2
125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 2
NDVLTYZPCACLMA-UHFFFAOYSA-N silver oxide Chemical compound [O-2].[Ag+].[Ag+] NDVLTYZPCACLMA-UHFFFAOYSA-N 0.000 description 2
229940116411 terpineol Drugs 0.000 description 2
YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 2
MWOOGOJBHIARFG-UHFFFAOYSA-N vanillin Chemical compound COC1=CC(C=O)=CC=C1O MWOOGOJBHIARFG-UHFFFAOYSA-N 0.000 description 2
FGQOOHJZONJGDT-UHFFFAOYSA-N vanillin Natural products COC1=CC(O)=CC(C=O)=C1 FGQOOHJZONJGDT-UHFFFAOYSA-N 0.000 description 2
235000012141 vanillin Nutrition 0.000 description 2
PHXATPHONSXBIL-UHFFFAOYSA-N xi-gamma-Undecalactone Chemical compound CCCCCCCC1CCC(=O)O1 PHXATPHONSXBIL-UHFFFAOYSA-N 0.000 description 2
PSQYTAPXSHCGMF-BQYQJAHWSA-N β-ionone Chemical compound CC(=O)\C=C\C1=C(C)CCCC1(C)C PSQYTAPXSHCGMF-BQYQJAHWSA-N 0.000 description 2
SFEOKXHPFMOVRM-UHFFFAOYSA-N (+)-(S)-gamma-ionone Natural products CC(=O)C=CC1C(=C)CCCC1(C)C SFEOKXHPFMOVRM-UHFFFAOYSA-N 0.000 description 1
SDOFMBGMRVAJNF-KVTDHHQDSA-N (2r,3r,4r,5r)-6-aminohexane-1,2,3,4,5-pentol Chemical compound NC[C@@H](O)[C@@H](O)[C@H](O)[C@H](O)CO SDOFMBGMRVAJNF-KVTDHHQDSA-N 0.000 description 1
WJTCHBVEUFDSIK-NWDGAFQWSA-N (2r,5s)-1-benzyl-2,5-dimethylpiperazine Chemical compound C[C@@H]1CN[C@@H](C)CN1CC1=CC=CC=C1 WJTCHBVEUFDSIK-NWDGAFQWSA-N 0.000 description 1
YURNCBVQZBJDAJ-AATRIKPKSA-N (E)-hept-2-enoic acid Chemical compound CCCC\C=C\C(O)=O YURNCBVQZBJDAJ-AATRIKPKSA-N 0.000 description 1
ZCHHRLHTBGRGOT-SNAWJCMRSA-N (E)-hex-2-en-1-ol Chemical compound CCC\C=C\CO ZCHHRLHTBGRGOT-SNAWJCMRSA-N 0.000 description 1
HRHOWZHRCRZVCU-AATRIKPKSA-N (E)-hex-2-enyl acetate Chemical compound CCC\C=C\COC(C)=O HRHOWZHRCRZVCU-AATRIKPKSA-N 0.000 description 1
239000001602 (E)-hex-3-enoic acid Substances 0.000 description 1
XTQLWNAWEPKOLB-SNAWJCMRSA-N (e)-2-methylhex-3-enoic acid Chemical compound CC\C=C\C(C)C(O)=O XTQLWNAWEPKOLB-SNAWJCMRSA-N 0.000 description 1
CIBMDQOEVWDTDT-ARJAWSKDSA-N (z)-5-methylhex-3-enoic acid Chemical compound CC(C)\C=C/CC(O)=O CIBMDQOEVWDTDT-ARJAWSKDSA-N 0.000 description 1
ZBPYTVBKHKUNHG-SREVYHEPSA-N (z)-non-3-enoic acid Chemical compound CCCCC\C=C/CC(O)=O ZBPYTVBKHKUNHG-SREVYHEPSA-N 0.000 description 1
HFZLSTDPRQSZCQ-UHFFFAOYSA-N 1-pyrrolidin-3-ylpyrrolidine Chemical compound C1CCCN1C1CNCC1 HFZLSTDPRQSZCQ-UHFFFAOYSA-N 0.000 description 1
XYHKNCXZYYTLRG-UHFFFAOYSA-N 1h-imidazole-2-carbaldehyde Chemical compound O=CC1=NC=CN1 XYHKNCXZYYTLRG-UHFFFAOYSA-N 0.000 description 1
LTMRRSWNXVJMBA-UHFFFAOYSA-L 2,2-diethylpropanedioate Chemical compound CCC(CC)(C([O-])=O)C([O-])=O LTMRRSWNXVJMBA-UHFFFAOYSA-L 0.000 description 1
RCSBILYQLVXLJG-UHFFFAOYSA-N 2-Propenyl hexanoate Chemical compound CCCCCC(=O)OCC=C RCSBILYQLVXLJG-UHFFFAOYSA-N 0.000 description 1
SKLXPNZDCBPHCS-UHFFFAOYSA-N 2-phenylpropyl butyrate Chemical compound CCCC(=O)OCC(C)C1=CC=CC=C1 SKLXPNZDCBPHCS-UHFFFAOYSA-N 0.000 description 1
CPVUNKGURQKKKX-UHFFFAOYSA-N 3-Decenoic acid Natural products CCCCCCC=CCC(O)=O CPVUNKGURQKKKX-UHFFFAOYSA-N 0.000 description 1
GWYFCOCPABKNJV-UHFFFAOYSA-M 3-Methylbutanoic acid Natural products CC(C)CC([O-])=O GWYFCOCPABKNJV-UHFFFAOYSA-M 0.000 description 1
CPVUNKGURQKKKX-FPLPWBNLSA-N 3Z-decenoic acid Chemical compound CCCCCC\C=C/CC(O)=O CPVUNKGURQKKKX-FPLPWBNLSA-N 0.000 description 1
MSHFRERJPWKJFX-UHFFFAOYSA-N 4-Methoxybenzyl alcohol Chemical compound COC1=CC=C(CO)C=C1 MSHFRERJPWKJFX-UHFFFAOYSA-N 0.000 description 1
239000004215 Carbon black (E152) Substances 0.000 description 1
NPBVQXIMTZKSBA-UHFFFAOYSA-N Chavibetol Natural products COC1=CC=C(CC=C)C=C1O NPBVQXIMTZKSBA-UHFFFAOYSA-N 0.000 description 1
XXHDAWYDNSXJQM-UHFFFAOYSA-N Chloride-3-Hexenoic acid Natural products CCC=CCC(O)=O XXHDAWYDNSXJQM-UHFFFAOYSA-N 0.000 description 1
WTEVQBCEXWBHNA-UHFFFAOYSA-N Citral Natural products CC(C)=CCCC(C)=CC=O WTEVQBCEXWBHNA-UHFFFAOYSA-N 0.000 description 1
241000207199 Citrus Species 0.000 description 1
235000008733 Citrus aurantifolia Nutrition 0.000 description 1
240000007154 Coffea arabica Species 0.000 description 1
240000006497 Dianthus caryophyllus Species 0.000 description 1
235000009355 Dianthus caryophyllus Nutrition 0.000 description 1
239000004278 EU approved seasoning Substances 0.000 description 1
ICMAFTSLXCXHRK-UHFFFAOYSA-N Ethyl pentanoate Chemical compound CCCCC(=O)OCC ICMAFTSLXCXHRK-UHFFFAOYSA-N 0.000 description 1
239000005770 Eugenol Substances 0.000 description 1
235000016623 Fragaria vesca Nutrition 0.000 description 1
240000009088 Fragaria x ananassa Species 0.000 description 1
235000011363 Fragaria x ananassa Nutrition 0.000 description 1
239000005792 Geraniol Substances 0.000 description 1
GLZPCOQZEFWAFX-YFHOEESVSA-N Geraniol Natural products CC(C)=CCC\C(C)=C/CO GLZPCOQZEFWAFX-YFHOEESVSA-N 0.000 description 1
241000208152 Geranium Species 0.000 description 1
244000178870 Lavandula angustifolia Species 0.000 description 1
235000010663 Lavandula angustifolia Nutrition 0.000 description 1
235000019501 Lemon oil Nutrition 0.000 description 1
HYMLWHLQFGRFIY-UHFFFAOYSA-N Maltol Natural products CC1OC=CC(=O)C1=O HYMLWHLQFGRFIY-UHFFFAOYSA-N 0.000 description 1
AMQJEAYHLZJPGS-UHFFFAOYSA-N N-Pentanol Chemical compound CCCCCO AMQJEAYHLZJPGS-UHFFFAOYSA-N 0.000 description 1
UVMRYBDEERADNV-UHFFFAOYSA-N Pseudoeugenol Natural products COC1=CC(C(C)=C)=CC=C1O UVMRYBDEERADNV-UHFFFAOYSA-N 0.000 description 1
235000006468 Thea sinensis Nutrition 0.000 description 1
235000009470 Theobroma cacao Nutrition 0.000 description 1
244000299461 Theobroma cacao Species 0.000 description 1
235000011941 Tilia x europaea Nutrition 0.000 description 1
240000006909 Tilia x europaea Species 0.000 description 1
CDJJKTLOZJAGIZ-UHFFFAOYSA-N Tolylacetate Chemical compound CC(=O)OC1=CC=C(C)C=C1 CDJJKTLOZJAGIZ-UHFFFAOYSA-N 0.000 description 1
235000013334 alcoholic beverage Nutrition 0.000 description 1
150000001299 aldehydes Chemical class 0.000 description 1
YIYBQIKDCADOSF-UHFFFAOYSA-N alpha-Butylen-alpha-carbonsaeure Natural products CCC=CC(O)=O YIYBQIKDCADOSF-UHFFFAOYSA-N 0.000 description 1
QUMXDOLUJCHOAY-UHFFFAOYSA-N alpha-methylbenzyl acetate Natural products CC(=O)OC(C)C1=CC=CC=C1 QUMXDOLUJCHOAY-UHFFFAOYSA-N 0.000 description 1
229940062909 amyl salicylate Drugs 0.000 description 1
235000021016 apples Nutrition 0.000 description 1
229910052786 argon Inorganic materials 0.000 description 1
125000003118 aryl group Chemical group 0.000 description 1
235000019445 benzyl alcohol Nutrition 0.000 description 1
GWYFCOCPABKNJV-UHFFFAOYSA-N beta-methyl-butyric acid Natural products CC(C)CC(O)=O GWYFCOCPABKNJV-UHFFFAOYSA-N 0.000 description 1
230000015572 biosynthetic process Effects 0.000 description 1
235000020279 black tea Nutrition 0.000 description 1
235000008429 bread Nutrition 0.000 description 1
XAPCMTMQBXLDBB-UHFFFAOYSA-N butanoic acid hexyl ester Natural products CCCCCCOC(=O)CCC XAPCMTMQBXLDBB-UHFFFAOYSA-N 0.000 description 1
125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
235000014171 carbonated beverage Nutrition 0.000 description 1
239000010627 cedar oil Substances 0.000 description 1
239000007795 chemical reaction product Substances 0.000 description 1
235000015218 chewing gum Nutrition 0.000 description 1
KRVSOGSZCMJSLX-UHFFFAOYSA-L chromic acid Substances O[Cr](O)(=O)=O KRVSOGSZCMJSLX-UHFFFAOYSA-L 0.000 description 1
WJSDHUCWMSHDCR-VMPITWQZSA-N cinnamyl acetate Natural products CC(=O)OC\C=C\C1=CC=CC=C1 WJSDHUCWMSHDCR-VMPITWQZSA-N 0.000 description 1
IWPOSDLLFZKGOW-WAYWQWQTSA-N cis-beta-octenoic acid Chemical compound CCCC\C=C/CC(O)=O IWPOSDLLFZKGOW-WAYWQWQTSA-N 0.000 description 1
229940043350 citral Drugs 0.000 description 1
239000001926 citrus aurantium l. subsp. bergamia wright et arn. oil Substances 0.000 description 1
235000020971 citrus fruits Nutrition 0.000 description 1
239000001071 citrus reticulata blanco var. mandarin Substances 0.000 description 1
235000016213 coffee Nutrition 0.000 description 1
235000013353 coffee beverage Nutrition 0.000 description 1
230000000052 comparative effect Effects 0.000 description 1
230000005494 condensation Effects 0.000 description 1
238000006482 condensation reaction Methods 0.000 description 1
239000006071 cream Substances 0.000 description 1
229940019836 cyclamen aldehyde Drugs 0.000 description 1
238000006114 decarboxylation reaction Methods 0.000 description 1
230000001877 deodorizing effect Effects 0.000 description 1
239000000645 desinfectant Substances 0.000 description 1
235000011850 desserts Nutrition 0.000 description 1
238000004821 distillation Methods 0.000 description 1
229940079593 drug Drugs 0.000 description 1
235000013399 edible fruits Nutrition 0.000 description 1
230000000694 effects Effects 0.000 description 1
239000003623 enhancer Substances 0.000 description 1
NYNCZOLNVTXTTP-UHFFFAOYSA-N ethyl 2-(1,3-dioxoisoindol-2-yl)acetate Chemical compound C1=CC=C2C(=O)N(CC(=O)OCC)C(=O)C2=C1 NYNCZOLNVTXTTP-UHFFFAOYSA-N 0.000 description 1
229960002217 eugenol Drugs 0.000 description 1
235000013355 food flavoring agent Nutrition 0.000 description 1
235000011194 food seasoning agent Nutrition 0.000 description 1
235000015203 fruit juice Nutrition 0.000 description 1
AWJWCTOOIBYHON-UHFFFAOYSA-N furo[3,4-b]pyrazine-5,7-dione Chemical compound C1=CN=C2C(=O)OC(=O)C2=N1 AWJWCTOOIBYHON-UHFFFAOYSA-N 0.000 description 1
OALYTRUKMRCXNH-QMMMGPOBSA-N gamma-Nonalactone Natural products CCCCC[C@H]1CCC(=O)O1 OALYTRUKMRCXNH-QMMMGPOBSA-N 0.000 description 1
PHXATPHONSXBIL-JTQLQIEISA-N gamma-Undecalactone Natural products CCCCCCC[C@H]1CCC(=O)O1 PHXATPHONSXBIL-JTQLQIEISA-N 0.000 description 1
229940020436 gamma-undecalactone Drugs 0.000 description 1
239000007789 gas Substances 0.000 description 1
WTEVQBCEXWBHNA-JXMROGBWSA-N geranial Chemical compound CC(C)=CCC\C(C)=C\C=O WTEVQBCEXWBHNA-JXMROGBWSA-N 0.000 description 1
229940113087 geraniol Drugs 0.000 description 1
239000010648 geranium oil Substances 0.000 description 1
235000019717 geranium oil Nutrition 0.000 description 1
125000003187 heptyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
125000004051 hexyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
229930195733 hydrocarbon Natural products 0.000 description 1
150000002430 hydrocarbons Chemical class 0.000 description 1
WPFVBOQKRVRMJB-UHFFFAOYSA-N hydroxycitronellal Chemical compound O=CCC(C)CCCC(C)(C)O WPFVBOQKRVRMJB-UHFFFAOYSA-N 0.000 description 1
235000015243 ice cream Nutrition 0.000 description 1
239000011261 inert gas Substances 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
150000002576 ketones Chemical class 0.000 description 1
239000000171 lavandula angustifolia l. flower oil Substances 0.000 description 1
239000001102 lavandula vera Substances 0.000 description 1
235000018219 lavender Nutrition 0.000 description 1
239000010501 lemon oil Substances 0.000 description 1
239000004571 lime Substances 0.000 description 1
UWKAYLJWKGQEPM-UHFFFAOYSA-N linalool acetate Natural products CC(C)=CCCC(C)(C=C)OC(C)=O UWKAYLJWKGQEPM-UHFFFAOYSA-N 0.000 description 1
229940043353 maltol Drugs 0.000 description 1
239000000463 material Substances 0.000 description 1
238000000034 method Methods 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
DVSDBMFJEQPWNO-UHFFFAOYSA-N methyllithium Chemical compound C[Li] DVSDBMFJEQPWNO-UHFFFAOYSA-N 0.000 description 1
235000020124 milk-based beverage Nutrition 0.000 description 1
125000001400 nonyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
YYZUSRORWSJGET-UHFFFAOYSA-N octanoic acid ethyl ester Natural products CCCCCCCC(=O)OCC YYZUSRORWSJGET-UHFFFAOYSA-N 0.000 description 1
125000002347 octyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
238000006053 organic reaction Methods 0.000 description 1
239000007800 oxidant agent Substances 0.000 description 1
230000001590 oxidative effect Effects 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
125000001147 pentyl group Chemical group C(CCCC)* 0.000 description 1
235000021018 plums Nutrition 0.000 description 1
UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 1
239000002994 raw material Substances 0.000 description 1
239000002453 shampoo Substances 0.000 description 1
229910001923 silver oxide Inorganic materials 0.000 description 1
235000011888 snacks Nutrition 0.000 description 1
238000003756 stirring Methods 0.000 description 1
125000001424 substituent group Chemical group 0.000 description 1
238000003786 synthesis reaction Methods 0.000 description 1
239000012438 synthetic essential oil Substances 0.000 description 1
235000013616 tea Nutrition 0.000 description 1
229940034610 toothpaste Drugs 0.000 description 1
239000000606 toothpaste Substances 0.000 description 1
IWPOSDLLFZKGOW-AATRIKPKSA-N trans-beta-octenoic acid Chemical compound CCCC\C=C\CC(O)=O IWPOSDLLFZKGOW-AATRIKPKSA-N 0.000 description 1
XXHDAWYDNSXJQM-ONEGZZNKSA-N trans-hex-3-enoic acid Chemical compound CC\C=C\CC(O)=O XXHDAWYDNSXJQM-ONEGZZNKSA-N 0.000 description 1
YIYBQIKDCADOSF-ONEGZZNKSA-N trans-pent-2-enoic acid Chemical compound CC\C=C\C(O)=O YIYBQIKDCADOSF-ONEGZZNKSA-N 0.000 description 1
AAAQKTZKLRYKHR-UHFFFAOYSA-N triphenylmethane Chemical compound C1=CC=CC=C1C(C=1C=CC=CC=1)C1=CC=CC=C1 AAAQKTZKLRYKHR-UHFFFAOYSA-N 0.000 description 1
ZFNVDHOSLNRHNN-UHFFFAOYSA-N xi-3-(4-Isopropylphenyl)-2-methylpropanal Chemical compound O=CC(C)CC1=CC=C(C(C)C)C=C1 ZFNVDHOSLNRHNN-UHFFFAOYSA-N 0.000 description 1

Classifications

- Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y02—TECHNOLOGIES OR APPLICATIONS FOR MITIGATION OR ADAPTATION AGAINST CLIMATE CHANGE
- Y02P—CLIMATE CHANGE MITIGATION TECHNOLOGIES IN THE PRODUCTION OR PROCESSING OF GOODS
- Y02P20/00—Technologies relating to chemical industry
- Y02P20/50—Improvements relating to the production of bulk chemicals
- Y02P20/52—Improvements relating to the production of bulk chemicals using catalysts, e.g. selective catalysts

Landscapes

Seasonings (AREA)
Cosmetics (AREA)
Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
Fats And Perfumes (AREA)

JP58135686A 1983-07-27 1983-07-27 シス−３−アルケン酸類、その製法および利用 Granted JPS6028950A (ja)

Priority Applications (1)

Application Number	Priority Date	Filing Date	Title
JP58135686A JPS6028950A (ja)	1983-07-27	1983-07-27	シス−３−アルケン酸類、その製法および利用

Applications Claiming Priority (1)

Application Number	Priority Date	Filing Date	Title
JP58135686A JPS6028950A (ja)	1983-07-27	1983-07-27	シス−３−アルケン酸類、その製法および利用

Publications (2)

Publication Number	Publication Date
JPS6028950A JPS6028950A (ja)	1985-02-14
JPH0368851B2 true JPH0368851B2 (lt)	1991-10-30

Family

ID=15157539

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
JP58135686A Granted JPS6028950A (ja)	1983-07-27	1983-07-27	シス−３−アルケン酸類、その製法および利用

Country Status (1)

Country	Link
JP (1)	JPS6028950A (lt)

Families Citing this family (4)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
US5410016A (en) *	1990-10-15	1995-04-25	Board Of Regents, The University Of Texas System	Photopolymerizable biodegradable hydrogels as tissue contacting materials and controlled-release carriers
US5626863A (en) *	1992-02-28	1997-05-06	Board Of Regents, The University Of Texas System	Photopolymerizable biodegradable hydrogels as tissue contacting materials and controlled-release carriers
NZ249770A (en)	1992-02-28	1996-09-25	Univ Texas	Biodegradable, polymerisable, substantially water soluble macromer comprising at least one water soluble region, at least one degradable region and at least two free radical polymerisable regions separated by at least one degradable region
JP4920290B2 (ja) *	2006-04-18	2012-04-18	富士フレーバー株式会社	２，３−ジヒドロ−２，３，５−トリメチル−６−（１−メチル−２−ブテニル）−４−ｈ−ピラン−４−オンの製造方法およびそれに用いる中間体

1983
- 1983-07-27 JP JP58135686A patent/JPS6028950A/ja active Granted

Non-Patent Citations (1)

* Cited by examiner, † Cited by third party
Title
CHEMICAL ABSTRACTS=1978 *

Also Published As

Publication number	Publication date
JPS6028950A (ja)	1985-02-14

Publication	Publication Date	Title
JPS6028950A (ja)	1985-02-14	シス−３−アルケン酸類、その製法および利用
JPH02282339A (ja)	1990-11-19	ケトン類およびアルコール類
JPH07119434B2 (ja)	1995-12-20	香料組成物
KR20100037598A (ko)	2010-04-09	6,8,10-운데카트리엔-3 또는 4-온 및 향료 조성물
JP2741091B2 (ja)	1998-04-15	８―メチル―４（ｚ）―ノネン誘導体
JP2794331B2 (ja)	1998-09-03	３，７―デカジエン―５―オリド類
JPH083094A (ja)	1996-01-09	シクロヘキセン誘導体
JP3635178B2 (ja)	2005-04-06	香料組成物
JP3635182B2 (ja)	2005-04-06	香料組成物
JP7232087B2 (ja)	2023-03-02	２－アルキリデン－メチルシクロヘキサノン系化合物からなる新規な香料
JPH0358984A (ja)	1991-03-14	持続性香気香味賦与及至改良補強剤
JPH0259564A (ja)	1990-02-28	（ｒ）‐（‐）‐２‐デセン‐５‐オリドの製法
JP2727253B2 (ja)	1998-03-11	２，６―ジメチル―５―ヘプテン―４―オリド
JPH05255690A (ja)	1993-10-05	持続性香気香味賦与乃至変調剤
JP2816775B2 (ja)	1998-10-27	香料組成物
JPS6050194B2 (ja)	1985-11-07	ジヒドロピラン誘導体、その製法及び利用
JP2818511B2 (ja)	1998-10-30	テトラヒドロフルフリル３−メルカプトプロピオネートおよび香料組成物
JPS62292778A (ja)	1987-12-19	４，７，７，１１−テトラメチル−１２−オキサ−ビシクロ（９，４，０）−４，８，１３−ペンタデカトリエン
JPH0457658B2 (lt)	1992-09-14
JPH0469133B2 (lt)	1992-11-05
JPH02196740A (ja)	1990-08-03	脂肪族ケトン類および脂肪族アルコール類
JP3583176B2 (ja)	2004-10-27	光学活性４−ヒドロキシ−１−ｐ−メンテン類
JPS62292739A (ja)	1987-12-19	フムレン誘導体
JPS6081164A (ja)	1985-05-09	α−もしくはβ−モノシクロホモフアルネシル酸の製法
JPS60149574A (ja)	1985-08-07	２−アルコキシ−４−エチル−３−メチル−２−ブテン−４，１−オリド類