KR20090113260A - 활성 알데히드 및 케톤의 평형 유동 혼합물로부터의 제어 방출 - Google Patents
활성 알데히드 및 케톤의 평형 유동 혼합물로부터의 제어 방출 Download PDFInfo
- Publication number
- KR20090113260A KR20090113260A KR1020097014238A KR20097014238A KR20090113260A KR 20090113260 A KR20090113260 A KR 20090113260A KR 1020097014238 A KR1020097014238 A KR 1020097014238A KR 20097014238 A KR20097014238 A KR 20097014238A KR 20090113260 A KR20090113260 A KR 20090113260A
- Authority
- KR
- South Korea
- Prior art keywords
- group
- formula
- diamine
- optionally substituted
- derivative
- 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.)
- Ceased
Links
- 239000000203 mixture Substances 0.000 title claims abstract description 157
- 150000001299 aldehydes Chemical class 0.000 title claims abstract description 118
- 150000002576 ketones Chemical class 0.000 title claims abstract description 96
- 238000013270 controlled release Methods 0.000 title claims description 9
- 150000001875 compounds Chemical class 0.000 claims abstract description 48
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims abstract description 38
- 125000003118 aryl group Chemical group 0.000 claims abstract description 28
- 239000003205 fragrance Substances 0.000 claims description 90
- 239000000047 product Substances 0.000 claims description 48
- 239000002585 base Substances 0.000 claims description 46
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 35
- 239000002304 perfume Substances 0.000 claims description 34
- -1 iminomethylene Chemical group 0.000 claims description 32
- 239000000796 flavoring agent Substances 0.000 claims description 25
- 235000019634 flavors Nutrition 0.000 claims description 25
- 230000000694 effects Effects 0.000 claims description 24
- 150000001412 amines Chemical class 0.000 claims description 23
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 23
- 125000003342 alkenyl group Chemical group 0.000 claims description 19
- 239000007788 liquid Substances 0.000 claims description 18
- 125000000217 alkyl group Chemical group 0.000 claims description 16
- 238000000034 method Methods 0.000 claims description 16
- AVXURJPOCDRRFD-UHFFFAOYSA-N Hydroxylamine Chemical compound ON AVXURJPOCDRRFD-UHFFFAOYSA-N 0.000 claims description 13
- 241000607479 Yersinia pestis Species 0.000 claims description 12
- 239000002386 air freshener Substances 0.000 claims description 11
- 125000004178 (C1-C4) alkyl group Chemical group 0.000 claims description 10
- 239000004615 ingredient Substances 0.000 claims description 10
- 239000005871 repellent Substances 0.000 claims description 10
- 230000002940 repellent Effects 0.000 claims description 10
- 239000007787 solid Substances 0.000 claims description 10
- 125000006273 (C1-C3) alkyl group Chemical group 0.000 claims description 9
- 239000005667 attractant Substances 0.000 claims description 9
- 239000003599 detergent Substances 0.000 claims description 9
- 239000000835 fiber Substances 0.000 claims description 9
- 125000002485 formyl group Chemical group [H]C(*)=O 0.000 claims description 9
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims description 8
- 150000007854 aminals Chemical class 0.000 claims description 7
- 238000002360 preparation method Methods 0.000 claims description 7
- GLUUGHFHXGJENI-UHFFFAOYSA-N Piperazine Chemical compound C1CNCCN1 GLUUGHFHXGJENI-UHFFFAOYSA-N 0.000 claims description 6
- 150000003934 aromatic aldehydes Chemical class 0.000 claims description 6
- 230000031902 chemoattractant activity Effects 0.000 claims description 6
- RXLUOFXICZSZIB-UHFFFAOYSA-N n,n'-dibenzylpropane-1,3-diamine Chemical compound C=1C=CC=CC=1CNCCCNCC1=CC=CC=C1 RXLUOFXICZSZIB-UHFFFAOYSA-N 0.000 claims description 6
- 230000001166 anti-perspirative effect Effects 0.000 claims description 5
- 239000003213 antiperspirant Substances 0.000 claims description 5
- 239000002781 deodorant agent Substances 0.000 claims description 5
- SJBYIGXWWGSEES-UHFFFAOYSA-N 1-n,2-n-dibenzylcyclohexane-1,2-diamine Chemical compound C=1C=CC=CC=1CNC1CCCCC1NCC1=CC=CC=C1 SJBYIGXWWGSEES-UHFFFAOYSA-N 0.000 claims description 4
- 239000002537 cosmetic Substances 0.000 claims description 4
- FKJLUBFUVIGVQS-UHFFFAOYSA-N n,n'-bis[(4-ethylphenyl)methyl]ethane-1,2-diamine Chemical compound C1=CC(CC)=CC=C1CNCCNCC1=CC=C(CC)C=C1 FKJLUBFUVIGVQS-UHFFFAOYSA-N 0.000 claims description 4
- AVHNOBYTCDKTEV-UHFFFAOYSA-N n,n'-bis[(4-methoxyphenyl)methyl]ethane-1,2-diamine Chemical compound C1=CC(OC)=CC=C1CNCCNCC1=CC=C(OC)C=C1 AVHNOBYTCDKTEV-UHFFFAOYSA-N 0.000 claims description 4
- CKCCOVSHDQOTNC-UHFFFAOYSA-N n,n'-bis[[4-(dimethylamino)phenyl]methyl]ethane-1,2-diamine Chemical compound C1=CC(N(C)C)=CC=C1CNCCNCC1=CC=C(N(C)C)C=C1 CKCCOVSHDQOTNC-UHFFFAOYSA-N 0.000 claims description 4
- UCVBNHJQXVIAEU-UHFFFAOYSA-N n,n'-bis[[4-(dimethylamino)phenyl]methyl]propane-1,3-diamine Chemical compound C1=CC(N(C)C)=CC=C1CNCCCNCC1=CC=C(N(C)C)C=C1 UCVBNHJQXVIAEU-UHFFFAOYSA-N 0.000 claims description 4
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 4
- 239000004753 textile Substances 0.000 claims description 4
- 125000006702 (C1-C18) alkyl group Chemical group 0.000 claims description 3
- 125000004169 (C1-C6) alkyl group Chemical group 0.000 claims description 3
- QAOWNCQODCNURD-UHFFFAOYSA-L Sulfate Chemical group [O-]S([O-])(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-L 0.000 claims description 3
- 229910001413 alkali metal ion Inorganic materials 0.000 claims description 3
- 125000000118 dimethyl group Chemical group [H]C([H])([H])* 0.000 claims description 3
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 3
- 125000005843 halogen group Chemical group 0.000 claims description 3
- 239000000077 insect repellent Substances 0.000 claims description 3
- 238000010409 ironing Methods 0.000 claims description 3
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 3
- QVGJBXLXNGAZPZ-UHFFFAOYSA-N n,n'-bis[(4-methoxyphenyl)methyl]propane-1,3-diamine Chemical compound C1=CC(OC)=CC=C1CNCCCNCC1=CC=C(OC)C=C1 QVGJBXLXNGAZPZ-UHFFFAOYSA-N 0.000 claims description 3
- MBHFHLMJDQZVTL-UHFFFAOYSA-N 1,2,3-tribenzylimidazolidine Chemical compound C=1C=CC=CC=1CC(N(CC1)CC=2C=CC=CC=2)N1CC1=CC=CC=C1 MBHFHLMJDQZVTL-UHFFFAOYSA-N 0.000 claims description 2
- SUZXCMFTAFNBCZ-UHFFFAOYSA-N 1,3-dibenzyl-2-(2-phenylethenyl)imidazolidine Chemical compound C=1C=CC=CC=1CN(C1C=CC=2C=CC=CC=2)CCN1CC1=CC=CC=C1 SUZXCMFTAFNBCZ-UHFFFAOYSA-N 0.000 claims description 2
- ZJVDSVMMDFKVJR-UHFFFAOYSA-N 1,3-dibenzyl-2-hexylimidazolidine Chemical compound C1CN(CC=2C=CC=CC=2)C(CCCCCC)N1CC1=CC=CC=C1 ZJVDSVMMDFKVJR-UHFFFAOYSA-N 0.000 claims description 2
- FQUYSHZXSKYCSY-UHFFFAOYSA-N 1,4-diazepane Chemical compound C1CNCCNC1 FQUYSHZXSKYCSY-UHFFFAOYSA-N 0.000 claims description 2
- 241000195940 Bryophyta Species 0.000 claims description 2
- BYTKQYBUDUPJFC-UHFFFAOYSA-N N,N'-dibenzylethane-1,2-diamine Chemical compound C=1C=CC=CC=1CNCCNCC1=CC=CC=C1.C=1C=CC=CC=1CNCCNCC1=CC=CC=C1 BYTKQYBUDUPJFC-UHFFFAOYSA-N 0.000 claims description 2
- 125000002777 acetyl group Chemical group [H]C([H])([H])C(*)=O 0.000 claims description 2
- 125000003545 alkoxy group Chemical group 0.000 claims description 2
- 239000007844 bleaching agent Substances 0.000 claims description 2
- 125000004177 diethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 2
- 239000006210 lotion Substances 0.000 claims description 2
- 235000011929 mousse Nutrition 0.000 claims description 2
- QEUWNGJNPLRKLR-UHFFFAOYSA-N n,n'-dibenzyl-1,2-diphenylethane-1,2-diamine Chemical compound C=1C=CC=CC=1CNC(C=1C=CC=CC=1)C(C=1C=CC=CC=1)NCC1=CC=CC=C1 QEUWNGJNPLRKLR-UHFFFAOYSA-N 0.000 claims description 2
- 239000000344 soap Substances 0.000 claims description 2
- 125000006592 (C2-C3) alkenyl group Chemical group 0.000 claims 1
- 150000008365 aromatic ketones Chemical class 0.000 claims 1
- 150000004985 diamines Chemical class 0.000 abstract description 77
- 239000012530 fluid Substances 0.000 abstract description 11
- 238000002156 mixing Methods 0.000 abstract description 6
- WGQKYBSKWIADBV-UHFFFAOYSA-N benzylamine Chemical group NCC1=CC=CC=C1 WGQKYBSKWIADBV-UHFFFAOYSA-N 0.000 abstract 1
- 239000000306 component Substances 0.000 description 42
- HUMNYLRZRPPJDN-UHFFFAOYSA-N benzaldehyde Chemical compound O=CC1=CC=CC=C1 HUMNYLRZRPPJDN-UHFFFAOYSA-N 0.000 description 40
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 39
- 239000000243 solution Substances 0.000 description 39
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 33
- 230000015572 biosynthetic process Effects 0.000 description 33
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 30
- QNGNSVIICDLXHT-UHFFFAOYSA-N para-ethylbenzaldehyde Natural products CCC1=CC=C(C=O)C=C1 QNGNSVIICDLXHT-UHFFFAOYSA-N 0.000 description 30
- 238000006243 chemical reaction Methods 0.000 description 24
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 18
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 18
- 239000002904 solvent Substances 0.000 description 18
- 238000003786 synthesis reaction Methods 0.000 description 18
- 239000000126 substance Substances 0.000 description 15
- 239000000523 sample Substances 0.000 description 14
- 239000011734 sodium Substances 0.000 description 14
- 230000002441 reversible effect Effects 0.000 description 13
- HYBBIBNJHNGZAN-UHFFFAOYSA-N furfural Chemical compound O=CC1=CC=CO1 HYBBIBNJHNGZAN-UHFFFAOYSA-N 0.000 description 11
- 229910052757 nitrogen Inorganic materials 0.000 description 11
- 239000002979 fabric softener Substances 0.000 description 10
- 239000000499 gel Substances 0.000 description 10
- 230000007062 hydrolysis Effects 0.000 description 10
- 238000006460 hydrolysis reaction Methods 0.000 description 10
- 239000002453 shampoo Substances 0.000 description 10
- 150000001413 amino acids Chemical class 0.000 description 9
- 239000002609 medium Substances 0.000 description 9
- 238000003756 stirring Methods 0.000 description 9
- 238000001704 evaporation Methods 0.000 description 8
- 230000008020 evaporation Effects 0.000 description 8
- ZRSNZINYAWTAHE-UHFFFAOYSA-N p-methoxybenzaldehyde Chemical compound COC1=CC=C(C=O)C=C1 ZRSNZINYAWTAHE-UHFFFAOYSA-N 0.000 description 8
- 239000013074 reference sample Substances 0.000 description 8
- 238000005070 sampling Methods 0.000 description 8
- GNKZMNRKLCTJAY-UHFFFAOYSA-N 4'-Methylacetophenone Chemical compound CC(=O)C1=CC=C(C)C=C1 GNKZMNRKLCTJAY-UHFFFAOYSA-N 0.000 description 7
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 7
- 239000000654 additive Substances 0.000 description 7
- 150000001491 aromatic compounds Chemical class 0.000 description 7
- 239000010410 layer Substances 0.000 description 7
- 239000011541 reaction mixture Substances 0.000 description 7
- 239000004094 surface-active agent Substances 0.000 description 7
- 239000003039 volatile agent Substances 0.000 description 7
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 6
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 6
- 229920000742 Cotton Polymers 0.000 description 6
- YZCKVEUIGOORGS-OUBTZVSYSA-N Deuterium Chemical compound [2H] YZCKVEUIGOORGS-OUBTZVSYSA-N 0.000 description 6
- 238000005481 NMR spectroscopy Methods 0.000 description 6
- 239000004480 active ingredient Substances 0.000 description 6
- 238000007792 addition Methods 0.000 description 6
- AKGGYBADQZYZPD-UHFFFAOYSA-N benzylacetone Chemical compound CC(=O)CCC1=CC=CC=C1 AKGGYBADQZYZPD-UHFFFAOYSA-N 0.000 description 6
- NEHNMFOYXAPHSD-UHFFFAOYSA-N citronellal Chemical compound O=CCC(C)CCC=C(C)C NEHNMFOYXAPHSD-UHFFFAOYSA-N 0.000 description 6
- 238000001035 drying Methods 0.000 description 6
- 239000002243 precursor Substances 0.000 description 6
- 239000011550 stock solution Substances 0.000 description 6
- XFNJVJPLKCPIBV-UHFFFAOYSA-N trimethylenediamine Chemical compound NCCCN XFNJVJPLKCPIBV-UHFFFAOYSA-N 0.000 description 6
- 238000005160 1H NMR spectroscopy Methods 0.000 description 5
- WTPYRCJDOZVZON-UHFFFAOYSA-N 3,5,5-Trimethylhexanal Chemical compound O=CCC(C)CC(C)(C)C WTPYRCJDOZVZON-UHFFFAOYSA-N 0.000 description 5
- QMXBURPYNWBMJR-UHFFFAOYSA-N 6-methoxy-2,6-dimethylheptanal Chemical compound COC(C)(C)CCCC(C)C=O QMXBURPYNWBMJR-UHFFFAOYSA-N 0.000 description 5
- 230000008901 benefit Effects 0.000 description 5
- JUHORIMYRDESRB-UHFFFAOYSA-N benzathine Chemical compound C=1C=CC=CC=1CNCCNCC1=CC=CC=C1 JUHORIMYRDESRB-UHFFFAOYSA-N 0.000 description 5
- 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 description 5
- 238000004140 cleaning Methods 0.000 description 5
- 229910052805 deuterium Inorganic materials 0.000 description 5
- 238000004817 gas chromatography Methods 0.000 description 5
- 238000010438 heat treatment Methods 0.000 description 5
- 230000001976 improved effect Effects 0.000 description 5
- 230000001965 increasing effect Effects 0.000 description 5
- KVKFRMCSXWQSNT-UHFFFAOYSA-N n,n'-dimethylethane-1,2-diamine Chemical compound CNCCNC KVKFRMCSXWQSNT-UHFFFAOYSA-N 0.000 description 5
- 125000001424 substituent group Chemical group 0.000 description 5
- SJBYIGXWWGSEES-WOJBJXKFSA-N (1r,2r)-1-n,2-n-dibenzylcyclohexane-1,2-diamine Chemical compound N([C@@H]1CCCC[C@H]1NCC=1C=CC=CC=1)CC1=CC=CC=C1 SJBYIGXWWGSEES-WOJBJXKFSA-N 0.000 description 4
- SSJXIUAHEKJCMH-PHDIDXHHSA-N (1r,2r)-cyclohexane-1,2-diamine Chemical compound N[C@@H]1CCCC[C@H]1N SSJXIUAHEKJCMH-PHDIDXHHSA-N 0.000 description 4
- SSJXIUAHEKJCMH-OLQVQODUSA-N (1s,2r)-cyclohexane-1,2-diamine Chemical compound N[C@H]1CCCC[C@H]1N SSJXIUAHEKJCMH-OLQVQODUSA-N 0.000 description 4
- 239000002671 adjuvant Substances 0.000 description 4
- 239000000872 buffer Substances 0.000 description 4
- 150000001728 carbonyl compounds Chemical class 0.000 description 4
- 230000008859 change Effects 0.000 description 4
- KSMVZQYAVGTKIV-UHFFFAOYSA-N decanal Chemical compound CCCCCCCCCC=O KSMVZQYAVGTKIV-UHFFFAOYSA-N 0.000 description 4
- 238000000605 extraction Methods 0.000 description 4
- 238000009472 formulation Methods 0.000 description 4
- CATSNJVOTSVZJV-UHFFFAOYSA-N heptan-2-one Chemical compound CCCCCC(C)=O CATSNJVOTSVZJV-UHFFFAOYSA-N 0.000 description 4
- 239000000463 material Substances 0.000 description 4
- 238000005406 washing Methods 0.000 description 4
- VNWOJVJCRAHBJJ-UHFFFAOYSA-N 2-pentylcyclopentan-1-one Chemical compound CCCCCC1CCCC1=O VNWOJVJCRAHBJJ-UHFFFAOYSA-N 0.000 description 3
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 3
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 3
- PIICEJLVQHRZGT-UHFFFAOYSA-N Ethylenediamine Chemical compound NCCN PIICEJLVQHRZGT-UHFFFAOYSA-N 0.000 description 3
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical class [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 3
- 239000012736 aqueous medium Substances 0.000 description 3
- 239000000969 carrier Substances 0.000 description 3
- 230000015556 catabolic process Effects 0.000 description 3
- 235000000983 citronellal Nutrition 0.000 description 3
- 229930003633 citronellal Natural products 0.000 description 3
- 238000006731 degradation reaction Methods 0.000 description 3
- 230000008021 deposition Effects 0.000 description 3
- 238000002474 experimental method Methods 0.000 description 3
- 239000004744 fabric Substances 0.000 description 3
- 238000002347 injection Methods 0.000 description 3
- 239000007924 injection Substances 0.000 description 3
- 230000005923 long-lasting effect Effects 0.000 description 3
- 125000004433 nitrogen atom Chemical group N* 0.000 description 3
- 235000019645 odor Nutrition 0.000 description 3
- 239000012044 organic layer Substances 0.000 description 3
- 230000002688 persistence Effects 0.000 description 3
- 238000000935 solvent evaporation Methods 0.000 description 3
- 238000003860 storage Methods 0.000 description 3
- 239000008399 tap water Substances 0.000 description 3
- 235000020679 tap water Nutrition 0.000 description 3
- 238000012360 testing method Methods 0.000 description 3
- NEHNMFOYXAPHSD-SNVBAGLBSA-N (+)-Citronellal Chemical compound O=CC[C@H](C)CCC=C(C)C NEHNMFOYXAPHSD-SNVBAGLBSA-N 0.000 description 2
- 125000000008 (C1-C10) alkyl group Chemical group 0.000 description 2
- KJPRLNWUNMBNBZ-QPJJXVBHSA-N (E)-cinnamaldehyde Chemical compound O=C\C=C\C1=CC=CC=C1 KJPRLNWUNMBNBZ-QPJJXVBHSA-N 0.000 description 2
- AYFJNMWCQAJEON-UHFFFAOYSA-N 1,3-dibenzyl-2-phenyl-1,3-diazinane Chemical compound C=1C=CC=CC=1CN(C1C=2C=CC=CC=2)CCCN1CC1=CC=CC=C1 AYFJNMWCQAJEON-UHFFFAOYSA-N 0.000 description 2
- DXIWBWIDAYBUDF-UHFFFAOYSA-N 1-(3,3-dimethylcyclohexyl)ethanone Chemical compound CC(=O)C1CCCC(C)(C)C1 DXIWBWIDAYBUDF-UHFFFAOYSA-N 0.000 description 2
- MZZRKEIUNOYYDF-UHFFFAOYSA-N 2,4-dimethylcyclohex-3-ene-1-carbaldehyde Chemical compound CC1C=C(C)CCC1C=O MZZRKEIUNOYYDF-UHFFFAOYSA-N 0.000 description 2
- NFAVNWJJYQAGNB-UHFFFAOYSA-N 2-methylundecanal Chemical compound CCCCCCCCCC(C)C=O NFAVNWJJYQAGNB-UHFFFAOYSA-N 0.000 description 2
- GTJOHISYCKPIMT-UHFFFAOYSA-N 2-methylundecane Chemical compound CCCCCCCCCC(C)C GTJOHISYCKPIMT-UHFFFAOYSA-N 0.000 description 2
- ALHUZKCOMYUFRB-UHFFFAOYSA-N 3-methylcyclopentadecan-1-one Chemical compound CC1CCCCCCCCCCCCC(=O)C1 ALHUZKCOMYUFRB-UHFFFAOYSA-N 0.000 description 2
- MYHGOWDLVRDUFA-UHFFFAOYSA-N 3-phenylbutanal Chemical compound O=CCC(C)C1=CC=CC=C1 MYHGOWDLVRDUFA-UHFFFAOYSA-N 0.000 description 2
- WKQWDIFHKYWRTA-UHFFFAOYSA-N 4,7-dimethyloct-6-en-3-one Chemical compound CCC(=O)C(C)CC=C(C)C WKQWDIFHKYWRTA-UHFFFAOYSA-N 0.000 description 2
- DCSKAMGZSIRJAQ-UHFFFAOYSA-N 4-(2-methylbutan-2-yl)cyclohexan-1-one Chemical compound CCC(C)(C)C1CCC(=O)CC1 DCSKAMGZSIRJAQ-UHFFFAOYSA-N 0.000 description 2
- BGNGWHSBYQYVRX-UHFFFAOYSA-N 4-(dimethylamino)benzaldehyde Chemical compound CN(C)C1=CC=C(C=O)C=C1 BGNGWHSBYQYVRX-UHFFFAOYSA-N 0.000 description 2
- NTPLXRHDUXRPNE-UHFFFAOYSA-N 4-methoxyacetophenone Chemical compound COC1=CC=C(C(C)=O)C=C1 NTPLXRHDUXRPNE-UHFFFAOYSA-N 0.000 description 2
- JHJCHCSUEGPIGE-UHFFFAOYSA-N 7,8-Dihydro-alpha-ionone Chemical compound CC(=O)CCC1C(C)=CCCC1(C)C JHJCHCSUEGPIGE-UHFFFAOYSA-N 0.000 description 2
- KWOLFJPFCHCOCG-UHFFFAOYSA-N Acetophenone Chemical compound CC(=O)C1=CC=CC=C1 KWOLFJPFCHCOCG-UHFFFAOYSA-N 0.000 description 2
- UXVMQQNJUSDDNG-UHFFFAOYSA-L Calcium chloride Chemical compound [Cl-].[Cl-].[Ca+2] UXVMQQNJUSDDNG-UHFFFAOYSA-L 0.000 description 2
- FPVVYTCTZKCSOJ-UHFFFAOYSA-N Ethylene glycol distearate Chemical compound CCCCCCCCCCCCCCCCCC(=O)OCCOC(=O)CCCCCCCCCCCCCCCCC FPVVYTCTZKCSOJ-UHFFFAOYSA-N 0.000 description 2
- OAKJQQAXSVQMHS-UHFFFAOYSA-N Hydrazine Chemical compound NN OAKJQQAXSVQMHS-UHFFFAOYSA-N 0.000 description 2
- ATUOYWHBWRKTHZ-UHFFFAOYSA-N Propane Chemical compound CCC ATUOYWHBWRKTHZ-UHFFFAOYSA-N 0.000 description 2
- BQCADISMDOOEFD-UHFFFAOYSA-N Silver Chemical compound [Ag] BQCADISMDOOEFD-UHFFFAOYSA-N 0.000 description 2
- 230000002378 acidificating effect Effects 0.000 description 2
- 238000004458 analytical method Methods 0.000 description 2
- 239000012062 aqueous buffer Substances 0.000 description 2
- 239000007864 aqueous solution Substances 0.000 description 2
- FZJUFJKVIYFBSY-UHFFFAOYSA-N bourgeonal Chemical compound CC(C)(C)C1=CC=C(CCC=O)C=C1 FZJUFJKVIYFBSY-UHFFFAOYSA-N 0.000 description 2
- 239000001110 calcium chloride Substances 0.000 description 2
- 229910001628 calcium chloride Inorganic materials 0.000 description 2
- 238000004364 calculation method Methods 0.000 description 2
- 239000012482 calibration solution Substances 0.000 description 2
- SWUIQEBPZIHZQS-UHFFFAOYSA-N calone Chemical compound O1CC(=O)COC2=CC(C)=CC=C21 SWUIQEBPZIHZQS-UHFFFAOYSA-N 0.000 description 2
- DSSYKIVIOFKYAU-UHFFFAOYSA-N camphor Chemical compound C1CC2(C)C(=O)CC1C2(C)C DSSYKIVIOFKYAU-UHFFFAOYSA-N 0.000 description 2
- 229930008380 camphor Natural products 0.000 description 2
- ULDHMXUKGWMISQ-UHFFFAOYSA-N carvone Chemical compound CC(=C)C1CC=C(C)C(=O)C1 ULDHMXUKGWMISQ-UHFFFAOYSA-N 0.000 description 2
- 239000003795 chemical substances by application Substances 0.000 description 2
- KJPRLNWUNMBNBZ-UHFFFAOYSA-N cinnamic aldehyde Natural products O=CC=CC1=CC=CC=C1 KJPRLNWUNMBNBZ-UHFFFAOYSA-N 0.000 description 2
- WTWBUQJHJGUZCY-UHFFFAOYSA-N cuminaldehyde Chemical compound CC(C)C1=CC=C(C=O)C=C1 WTWBUQJHJGUZCY-UHFFFAOYSA-N 0.000 description 2
- OSOIQJGOYGSIMF-UHFFFAOYSA-N cyclopentadecanone Chemical compound O=C1CCCCCCCCCCCCCC1 OSOIQJGOYGSIMF-UHFFFAOYSA-N 0.000 description 2
- 238000000354 decomposition reaction Methods 0.000 description 2
- 239000008367 deionised water Substances 0.000 description 2
- 229910021641 deionized water Inorganic materials 0.000 description 2
- 238000003795 desorption Methods 0.000 description 2
- FLKPEMZONWLCSK-UHFFFAOYSA-N diethyl phthalate Chemical compound CCOC(=O)C1=CC=CC=C1C(=O)OCC FLKPEMZONWLCSK-UHFFFAOYSA-N 0.000 description 2
- 239000000839 emulsion Substances 0.000 description 2
- 238000005538 encapsulation Methods 0.000 description 2
- 238000011067 equilibration Methods 0.000 description 2
- CBOQJANXLMLOSS-UHFFFAOYSA-N ethyl vanillin Chemical compound CCOC1=CC(C=O)=CC=C1O CBOQJANXLMLOSS-UHFFFAOYSA-N 0.000 description 2
- 239000007789 gas Substances 0.000 description 2
- 239000008266 hair spray Substances 0.000 description 2
- BXWNKGSJHAJOGX-UHFFFAOYSA-N hexadecan-1-ol Chemical compound CCCCCCCCCCCCCCCCO BXWNKGSJHAJOGX-UHFFFAOYSA-N 0.000 description 2
- WPFVBOQKRVRMJB-UHFFFAOYSA-N hydroxycitronellal Chemical compound O=CCC(C)CCCC(C)(C)O WPFVBOQKRVRMJB-UHFFFAOYSA-N 0.000 description 2
- 150000002466 imines Chemical class 0.000 description 2
- 229930002839 ionone Natural products 0.000 description 2
- SDQFDHOLCGWZPU-UHFFFAOYSA-N lilial Chemical compound O=CC(C)CC1=CC=C(C(C)(C)C)C=C1 SDQFDHOLCGWZPU-UHFFFAOYSA-N 0.000 description 2
- XMGQYMWWDOXHJM-UHFFFAOYSA-N limonene Chemical compound CC(=C)C1CCC(C)=CC1 XMGQYMWWDOXHJM-UHFFFAOYSA-N 0.000 description 2
- 238000004519 manufacturing process Methods 0.000 description 2
- 230000007246 mechanism Effects 0.000 description 2
- KVWWIYGFBYDJQC-UHFFFAOYSA-N methyl dihydrojasmonate Chemical compound CCCCCC1C(CC(=O)OC)CCC1=O KVWWIYGFBYDJQC-UHFFFAOYSA-N 0.000 description 2
- 230000009965 odorless effect Effects 0.000 description 2
- PKZJLOCLABXVMC-UHFFFAOYSA-N ortho-Methoxybenzaldehyde Natural products COC1=CC=CC=C1C=O PKZJLOCLABXVMC-UHFFFAOYSA-N 0.000 description 2
- 125000004430 oxygen atom Chemical group O* 0.000 description 2
- FXLOVSHXALFLKQ-UHFFFAOYSA-N p-tolualdehyde Chemical compound CC1=CC=C(C=O)C=C1 FXLOVSHXALFLKQ-UHFFFAOYSA-N 0.000 description 2
- DTUQWGWMVIHBKE-UHFFFAOYSA-N phenylacetaldehyde Chemical compound O=CCC1=CC=CC=C1 DTUQWGWMVIHBKE-UHFFFAOYSA-N 0.000 description 2
- RHPBLLCTOLJFPH-UHFFFAOYSA-N piperidin-2-ylmethanamine Chemical compound NCC1CCCCN1 RHPBLLCTOLJFPH-UHFFFAOYSA-N 0.000 description 2
- SATCULPHIDQDRE-UHFFFAOYSA-N piperonal Chemical compound O=CC1=CC=C2OCOC2=C1 SATCULPHIDQDRE-UHFFFAOYSA-N 0.000 description 2
- 230000008092 positive effect Effects 0.000 description 2
- 239000000843 powder Substances 0.000 description 2
- 230000008569 process Effects 0.000 description 2
- 230000002035 prolonged effect Effects 0.000 description 2
- 239000002994 raw material Substances 0.000 description 2
- 239000012925 reference material Substances 0.000 description 2
- SMQUZDBALVYZAC-UHFFFAOYSA-N salicylaldehyde Chemical compound OC1=CC=CC=C1C=O SMQUZDBALVYZAC-UHFFFAOYSA-N 0.000 description 2
- 229920006395 saturated elastomer Polymers 0.000 description 2
- 229910052709 silver Inorganic materials 0.000 description 2
- 239000004332 silver Substances 0.000 description 2
- 239000007858 starting material Substances 0.000 description 2
- UHEPJGULSIKKTP-UHFFFAOYSA-N sulcatone Chemical compound CC(C)=CCCC(C)=O UHEPJGULSIKKTP-UHFFFAOYSA-N 0.000 description 2
- 235000007586 terpenes Nutrition 0.000 description 2
- MWOOGOJBHIARFG-UHFFFAOYSA-N vanillin Chemical compound COC1=CC(C=O)=CC=C1O MWOOGOJBHIARFG-UHFFFAOYSA-N 0.000 description 2
- NFLGAXVYCFJBMK-RKDXNWHRSA-N (+)-isomenthone Natural products CC(C)[C@H]1CC[C@@H](C)CC1=O NFLGAXVYCFJBMK-RKDXNWHRSA-N 0.000 description 1
- GEQHKFFSPGPGLN-PHDIDXHHSA-N (1r,3r)-cyclohexane-1,3-diamine Chemical compound N[C@@H]1CCC[C@@H](N)C1 GEQHKFFSPGPGLN-PHDIDXHHSA-N 0.000 description 1
- GEQHKFFSPGPGLN-OLQVQODUSA-N (1r,3s)-cyclohexane-1,3-diamine Chemical compound N[C@H]1CCC[C@@H](N)C1 GEQHKFFSPGPGLN-OLQVQODUSA-N 0.000 description 1
- SJBYIGXWWGSEES-BGYRXZFFSA-N (1s,2r)-1-n,2-n-dibenzylcyclohexane-1,2-diamine Chemical group N([C@H]1CCCC[C@H]1NCC=1C=CC=CC=1)CC1=CC=CC=C1 SJBYIGXWWGSEES-BGYRXZFFSA-N 0.000 description 1
- JZQKTMZYLHNFPL-BLHCBFLLSA-N (2E,4E)-deca-2,4-dienal Chemical compound CCCCC\C=C\C=C\C=O JZQKTMZYLHNFPL-BLHCBFLLSA-N 0.000 description 1
- HZYHMHHBBBSGHB-UHFFFAOYSA-N (2E,6E)-2,6-Nonadienal Natural products CCC=CCCC=CC=O HZYHMHHBBBSGHB-UHFFFAOYSA-N 0.000 description 1
- XTJLXXCARCJVPJ-TWTPFVCWSA-N (2e,4e)-hepta-2,4-diene Chemical compound CC\C=C\C=C\C XTJLXXCARCJVPJ-TWTPFVCWSA-N 0.000 description 1
- ZHHYXNZJDGDGPJ-BSWSSELBSA-N (2e,4e)-nona-2,4-dienal Chemical compound CCCC\C=C\C=C\C=O ZHHYXNZJDGDGPJ-BSWSSELBSA-N 0.000 description 1
- HZYHMHHBBBSGHB-DYWGDJMRSA-N (2e,6e)-nona-2,6-dienal Chemical compound CC\C=C\CC\C=C\C=O HZYHMHHBBBSGHB-DYWGDJMRSA-N 0.000 description 1
- CIXAYNMKFFQEFU-UHFFFAOYSA-N (4-Methylphenyl)acetaldehyde Chemical compound CC1=CC=C(CC=O)C=C1 CIXAYNMKFFQEFU-UHFFFAOYSA-N 0.000 description 1
- MMLYERLRGHVBEK-XYOKQWHBSA-N (4e)-5,9-dimethyldeca-4,8-dienal Chemical compound CC(C)=CCC\C(C)=C\CCC=O MMLYERLRGHVBEK-XYOKQWHBSA-N 0.000 description 1
- 235000011976 (R)-(+)-citronellal Nutrition 0.000 description 1
- DSSYKIVIOFKYAU-XCBNKYQSSA-N (R)-camphor Chemical compound C1C[C@@]2(C)C(=O)C[C@@H]1C2(C)C DSSYKIVIOFKYAU-XCBNKYQSSA-N 0.000 description 1
- NELDPSDYTZADSA-AATRIKPKSA-N (e)-1-(2,4,4-trimethylcyclohex-2-en-1-yl)but-2-en-1-one Chemical compound C\C=C\C(=O)C1CCC(C)(C)C=C1C NELDPSDYTZADSA-AATRIKPKSA-N 0.000 description 1
- XHOFTJRCBBQRFB-UXBLZVDNSA-N (e)-2,5,6-trimethylhept-4-enal Chemical compound CC(C)C(\C)=C\CC(C)C=O XHOFTJRCBBQRFB-UXBLZVDNSA-N 0.000 description 1
- YJRODKCOICMRBO-BQYQJAHWSA-N (e)-4-(2,2,6-trimethylcyclohexyl)but-3-en-2-one Chemical compound CC1CCCC(C)(C)C1\C=C\C(C)=O YJRODKCOICMRBO-BQYQJAHWSA-N 0.000 description 1
- DYLIWHYUXAJDOJ-OWOJBTEDSA-N (e)-4-(6-aminopurin-9-yl)but-2-en-1-ol Chemical compound NC1=NC=NC2=C1N=CN2C\C=C\CO DYLIWHYUXAJDOJ-OWOJBTEDSA-N 0.000 description 1
- VVGOCOMZRGWHPI-ONEGZZNKSA-N (e)-hept-4-enal Chemical compound CC\C=C\CCC=O VVGOCOMZRGWHPI-ONEGZZNKSA-N 0.000 description 1
- RTNPCOBSXBGDMO-ONEGZZNKSA-N (e)-non-6-enal Chemical compound CC\C=C\CCCCC=O RTNPCOBSXBGDMO-ONEGZZNKSA-N 0.000 description 1
- YGFGZTXGYTUXBA-UHFFFAOYSA-N (±)-2,6-dimethyl-5-heptenal Chemical compound O=CC(C)CCC=C(C)C YGFGZTXGYTUXBA-UHFFFAOYSA-N 0.000 description 1
- PONXTPCRRASWKW-UHFFFAOYSA-N 1,2-diphenylethane-1,2-diamine Chemical compound C=1C=CC=CC=1C(N)C(N)C1=CC=CC=C1 PONXTPCRRASWKW-UHFFFAOYSA-N 0.000 description 1
- DKYBVKMIZODYKL-UHFFFAOYSA-N 1,3-diazinane Chemical compound C1CNCNC1 DKYBVKMIZODYKL-UHFFFAOYSA-N 0.000 description 1
- JXPIQUCRBAHFGW-UHFFFAOYSA-N 1,3-dibenzyl-2-(3-phenylpropyl)imidazolidine Chemical compound C=1C=CC=CC=1CCCC(N(CC1)CC=2C=CC=CC=2)N1CC1=CC=CC=C1 JXPIQUCRBAHFGW-UHFFFAOYSA-N 0.000 description 1
- BMPLVANMUHQVEW-UHFFFAOYSA-N 1,3-dibenzyl-2-phenyl-3a,4,5,6,7,7a-hexahydro-2h-benzimidazole Chemical compound C=1C=CC=CC=1CN(C1C=2C=CC=CC=2)C2CCCCC2N1CC1=CC=CC=C1 BMPLVANMUHQVEW-UHFFFAOYSA-N 0.000 description 1
- DBFSGTXNKFBZCH-UHFFFAOYSA-N 1,3-dibenzyl-2-phenylimidazolidine Chemical compound C=1C=CC=CC=1CN(C1C=2C=CC=CC=2)CCN1CC1=CC=CC=C1 DBFSGTXNKFBZCH-UHFFFAOYSA-N 0.000 description 1
- QISTUHYRFABJSG-UHFFFAOYSA-N 1,3-dimethyl-2-phenylimidazolidine Chemical compound CN1CCN(C)C1C1=CC=CC=C1 QISTUHYRFABJSG-UHFFFAOYSA-N 0.000 description 1
- SPPWGCYEYAMHDT-UHFFFAOYSA-N 1,4-di(propan-2-yl)benzene Chemical compound CC(C)C1=CC=C(C(C)C)C=C1 SPPWGCYEYAMHDT-UHFFFAOYSA-N 0.000 description 1
- CHOOCIQDWNAXQQ-UHFFFAOYSA-N 1,5,5-trimethylcyclohexene Chemical compound CC1=CCCC(C)(C)C1 CHOOCIQDWNAXQQ-UHFFFAOYSA-N 0.000 description 1
- 239000001686 1,7,7-trimethylbicyclo[2.2.1]heptan-2-one Substances 0.000 description 1
- HSDSKVWQTONQBJ-UHFFFAOYSA-N 1-(2,4-dimethylphenyl)ethanone Chemical compound CC(=O)C1=CC=C(C)C=C1C HSDSKVWQTONQBJ-UHFFFAOYSA-N 0.000 description 1
- HDBXAQWZWHUVNC-UHFFFAOYSA-N 1-(2-methylpropyl)-4-propan-2-ylbenzene Chemical compound CC(C)CC1=CC=C(C(C)C)C=C1 HDBXAQWZWHUVNC-UHFFFAOYSA-N 0.000 description 1
- KJJMTKOKFXURKM-UHFFFAOYSA-N 1-(3,5,6-trimethylcyclohex-3-en-1-yl)ethanone Chemical compound CC1C=C(C)CC(C(C)=O)C1C KJJMTKOKFXURKM-UHFFFAOYSA-N 0.000 description 1
- OEVIJAZJVZDBQL-UHFFFAOYSA-N 1-(5,5-dimethylcyclohexen-1-yl)pent-4-en-1-one Chemical compound CC1(C)CCC=C(C(=O)CCC=C)C1 OEVIJAZJVZDBQL-UHFFFAOYSA-N 0.000 description 1
- HXKKHQJGJAFBHI-UHFFFAOYSA-N 1-aminopropan-2-ol Chemical compound CC(O)CN HXKKHQJGJAFBHI-UHFFFAOYSA-N 0.000 description 1
- VUIWFNRBSGUSIN-UHFFFAOYSA-N 1-methyl-4-(4-methylpent-3-enyl)cyclohex-3-ene-1-carbaldehyde Chemical compound CC(C)=CCCC1=CCC(C)(C=O)CC1 VUIWFNRBSGUSIN-UHFFFAOYSA-N 0.000 description 1
- TVPNGVPSNXPYLT-UHFFFAOYSA-N 1-phenylimidazolidine Chemical compound C1NCCN1C1=CC=CC=C1 TVPNGVPSNXPYLT-UHFFFAOYSA-N 0.000 description 1
- PUKWIVZFEZFVAT-UHFFFAOYSA-N 2,2,5-trimethyl-5-pentylcyclopentan-1-one Chemical compound CCCCCC1(C)CCC(C)(C)C1=O PUKWIVZFEZFVAT-UHFFFAOYSA-N 0.000 description 1
- CTLDWNVYXLHMAS-UHFFFAOYSA-N 2,4,4,7-tetramethyloct-6-en-3-one Chemical compound CC(C)C(=O)C(C)(C)CC=C(C)C CTLDWNVYXLHMAS-UHFFFAOYSA-N 0.000 description 1
- OVSKIKFHRZPJSS-UHFFFAOYSA-N 2,4-D Chemical compound OC(=O)COC1=CC=C(Cl)C=C1Cl OVSKIKFHRZPJSS-UHFFFAOYSA-N 0.000 description 1
- ZHHYXNZJDGDGPJ-UHFFFAOYSA-N 2,4-Nonadienal Natural products CCCCC=CC=CC=O ZHHYXNZJDGDGPJ-UHFFFAOYSA-N 0.000 description 1
- NYOHMJCUHOBGBN-UHFFFAOYSA-N 2,4-ditert-butylcyclohexan-1-one Chemical compound CC(C)(C)C1CCC(=O)C(C(C)(C)C)C1 NYOHMJCUHOBGBN-UHFFFAOYSA-N 0.000 description 1
- ZACLMVYBDSHRDN-UHFFFAOYSA-N 2,6,6-trimethylcycloheptan-1-one Chemical compound CC1CCCC(C)(C)CC1=O ZACLMVYBDSHRDN-UHFFFAOYSA-N 0.000 description 1
- MZPDTOMKQCMETI-UHFFFAOYSA-N 2,6-dimethylocta-2,6-diene Chemical compound CC=C(C)CCC=C(C)C MZPDTOMKQCMETI-UHFFFAOYSA-N 0.000 description 1
- JNRATHVXQNNAQX-UHFFFAOYSA-N 2-(4-methylidenecyclohexyl)propanal Chemical compound O=CC(C)C1CCC(=C)CC1 JNRATHVXQNNAQX-UHFFFAOYSA-N 0.000 description 1
- RVOWBRZFIAABEJ-UHFFFAOYSA-N 2-(4-methylpentoxy)acetaldehyde Chemical compound CC(C)CCCOCC=O RVOWBRZFIAABEJ-UHFFFAOYSA-N 0.000 description 1
- BSAIUMLZVGUGKX-UHFFFAOYSA-N 2-Nonenal Natural products CCCCCCC=CC=O BSAIUMLZVGUGKX-UHFFFAOYSA-N 0.000 description 1
- CJPNOLIZCWDHJK-UHFFFAOYSA-N 2-Pentadecanone Chemical compound CCCCCCCCCCCCCC(C)=O CJPNOLIZCWDHJK-UHFFFAOYSA-N 0.000 description 1
- GUUHFMWKWLOQMM-UHFFFAOYSA-N 2-benzylideneoctanal Chemical compound CCCCCCC(C=O)=CC1=CC=CC=C1 GUUHFMWKWLOQMM-UHFFFAOYSA-N 0.000 description 1
- RQXTZKGDMNIWJF-UHFFFAOYSA-N 2-butan-2-ylcyclohexan-1-one Chemical compound CCC(C)C1CCCCC1=O RQXTZKGDMNIWJF-UHFFFAOYSA-N 0.000 description 1
- JTHVYOIHZNYRCC-UHFFFAOYSA-N 2-hexylcyclopentan-1-one Chemical compound CCCCCCC1CCCC1=O JTHVYOIHZNYRCC-UHFFFAOYSA-N 0.000 description 1
- CFAKWWQIUFSQFU-UHFFFAOYSA-N 2-hydroxy-3-methylcyclopent-2-en-1-one Chemical compound CC1=C(O)C(=O)CC1 CFAKWWQIUFSQFU-UHFFFAOYSA-N 0.000 description 1
- 239000001431 2-methylbenzaldehyde Substances 0.000 description 1
- LBICMZLDYMBIGA-UHFFFAOYSA-N 2-methyldecanal Chemical compound CCCCCCCCC(C)C=O LBICMZLDYMBIGA-UHFFFAOYSA-N 0.000 description 1
- CCHAJZURXPPHJU-UHFFFAOYSA-N 2-naphthalen-1-ylacetaldehyde Chemical compound C1=CC=C2C(CC=O)=CC=CC2=C1 CCHAJZURXPPHJU-UHFFFAOYSA-N 0.000 description 1
- BSAIUMLZVGUGKX-FPLPWBNLSA-N 2-nonenal Chemical compound CCCCCC\C=C/C=O BSAIUMLZVGUGKX-FPLPWBNLSA-N 0.000 description 1
- LVBXEMGDVWVTGY-SREVYHEPSA-N 2-octenal Chemical compound CCCCC\C=C/C=O LVBXEMGDVWVTGY-SREVYHEPSA-N 0.000 description 1
- XFFILAFLGDUMBF-UHFFFAOYSA-N 2-phenoxyacetaldehyde Chemical compound O=CCOC1=CC=CC=C1 XFFILAFLGDUMBF-UHFFFAOYSA-N 0.000 description 1
- IQVAERDLDAZARL-UHFFFAOYSA-N 2-phenylpropanal Chemical compound O=CC(C)C1=CC=CC=C1 IQVAERDLDAZARL-UHFFFAOYSA-N 0.000 description 1
- XBJWSCVUINDBFF-UHFFFAOYSA-N 2-propyloctanal Chemical compound CCCCCCC(C=O)CCC XBJWSCVUINDBFF-UHFFFAOYSA-N 0.000 description 1
- JZQKTMZYLHNFPL-UHFFFAOYSA-N 2-trans-4-trans-decadienal Natural products CCCCCC=CC=CC=O JZQKTMZYLHNFPL-UHFFFAOYSA-N 0.000 description 1
- IXIYWQIFBRZMNR-UHFFFAOYSA-N 3,4,5,6,6-pentamethylhept-3-en-2-one Chemical compound CC(C)(C)C(C)C(C)=C(C)C(C)=O IXIYWQIFBRZMNR-UHFFFAOYSA-N 0.000 description 1
- DEMWVPUIZCCHPT-UHFFFAOYSA-N 3,5,6-trimethylcyclohex-3-ene-1-carbaldehyde Chemical compound CC1C=C(C)CC(C=O)C1C DEMWVPUIZCCHPT-UHFFFAOYSA-N 0.000 description 1
- ZHDQGHCZWWDMRS-UHFFFAOYSA-N 3,5-dimethylcyclohex-3-ene-1-carbaldehyde Chemical compound CC1CC(C=O)CC(C)=C1 ZHDQGHCZWWDMRS-UHFFFAOYSA-N 0.000 description 1
- OLXLPKQCGWYRFQ-UHFFFAOYSA-N 3-(4-hydroxy-4-methylpentyl)cyclohex-3-ene-1-carbaldehyde Chemical compound CC(C)(O)CCCC1=CCCC(C=O)C1 OLXLPKQCGWYRFQ-UHFFFAOYSA-N 0.000 description 1
- DDFGFKGJBOILQZ-UHFFFAOYSA-N 3-(6,6-dimethyl-4-bicyclo[3.1.1]hept-3-enyl)propanal Chemical compound C1C2C(C)(C)C1CC=C2CCC=O DDFGFKGJBOILQZ-UHFFFAOYSA-N 0.000 description 1
- DFJMIMVMOIFPQG-UHFFFAOYSA-N 3-methyl-5-phenylpentanal Chemical compound O=CCC(C)CCC1=CC=CC=C1 DFJMIMVMOIFPQG-UHFFFAOYSA-N 0.000 description 1
- YGCZTXZTJXYWCO-UHFFFAOYSA-N 3-phenylpropanal Chemical compound O=CCCC1=CC=CC=C1 YGCZTXZTJXYWCO-UHFFFAOYSA-N 0.000 description 1
- VUNCLQCPKWLBRY-UHFFFAOYSA-N 4,6,6-trimethylbicyclo[3.1.1]heptane-3-carbaldehyde Chemical compound C1C(C=O)C(C)C2C(C)(C)C1C2 VUNCLQCPKWLBRY-UHFFFAOYSA-N 0.000 description 1
- MQBIZQLCHSZBOI-UHFFFAOYSA-N 4-(4-Methyl-3-pentenyl)-3-cyclohexene-1-carboxaldehyde Chemical compound CC(C)=CCCC1=CCC(C=O)CC1 MQBIZQLCHSZBOI-UHFFFAOYSA-N 0.000 description 1
- ORMHZBNNECIKOH-UHFFFAOYSA-N 4-(4-hydroxy-4-methylpentyl)cyclohex-3-ene-1-carbaldehyde Chemical compound CC(C)(O)CCCC1=CCC(C=O)CC1 ORMHZBNNECIKOH-UHFFFAOYSA-N 0.000 description 1
- OSBLKUABEAVZCX-UHFFFAOYSA-N 4-(4-methoxyphenyl)butane-1,3-diamine Chemical compound COC1=CC=C(CC(CCN)N)C=C1 OSBLKUABEAVZCX-UHFFFAOYSA-N 0.000 description 1
- 125000004860 4-ethylphenyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1*)C([H])([H])C([H])([H])[H] 0.000 description 1
- HIQIXEFWDLTDED-UHFFFAOYSA-N 4-hydroxy-1-piperidin-4-ylpyrrolidin-2-one Chemical compound O=C1CC(O)CN1C1CCNCC1 HIQIXEFWDLTDED-UHFFFAOYSA-N 0.000 description 1
- 125000004203 4-hydroxyphenyl group Chemical group [H]OC1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 1
- AANMVENRNJYEMK-UHFFFAOYSA-N 4-propan-2-ylcyclohex-2-en-1-one Chemical compound CC(C)C1CCC(=O)C=C1 AANMVENRNJYEMK-UHFFFAOYSA-N 0.000 description 1
- PCYRHVCROYSFSX-UHFFFAOYSA-N 5-(2-methylpropyl)-1,3-benzodioxole Chemical compound CC(C)CC1=CC=C2OCOC2=C1 PCYRHVCROYSFSX-UHFFFAOYSA-N 0.000 description 1
- PSBKJPTZCVYXSD-UHFFFAOYSA-N 5-methylheptan-3-one Chemical compound CCC(C)CC(=O)CC PSBKJPTZCVYXSD-UHFFFAOYSA-N 0.000 description 1
- HBAQYPYDRFILMT-UHFFFAOYSA-N 8-[3-(1-cyclopropylpyrazol-4-yl)-1H-pyrazolo[4,3-d]pyrimidin-5-yl]-3-methyl-3,8-diazabicyclo[3.2.1]octan-2-one Chemical class C1(CC1)N1N=CC(=C1)C1=NNC2=C1N=C(N=C2)N1C2C(N(CC1CC2)C)=O HBAQYPYDRFILMT-UHFFFAOYSA-N 0.000 description 1
- JRKLRIAIMIKGHT-UHFFFAOYSA-N 8-bromoquinoline-4-carbaldehyde Chemical compound C1=CN=C2C(Br)=CC=CC2=C1C=O JRKLRIAIMIKGHT-UHFFFAOYSA-N 0.000 description 1
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Natural products CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 1
- 0 CC(C)(C(*)**)C(*)(*)C(C)(C)C(*)N* Chemical compound CC(C)(C(*)**)C(*)(*)C(C)(C)C(*)N* 0.000 description 1
- 239000005973 Carvone Substances 0.000 description 1
- VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 1
- 241000723346 Cinnamomum camphora Species 0.000 description 1
- WTEVQBCEXWBHNA-UHFFFAOYSA-N Citral Natural products CC(C)=CCCC(C)=CC=O WTEVQBCEXWBHNA-UHFFFAOYSA-N 0.000 description 1
- OMPIYDSYGYKWSG-UHFFFAOYSA-N Citronensaeure-alpha-aethylester Natural products CCOC(=O)CC(O)(C(O)=O)CC(O)=O OMPIYDSYGYKWSG-UHFFFAOYSA-N 0.000 description 1
- 108090000790 Enzymes Proteins 0.000 description 1
- 102000004190 Enzymes Human genes 0.000 description 1
- GMEONFUTDYJSNV-UHFFFAOYSA-N Ethyl levulinate Chemical compound CCOC(=O)CCC(C)=O GMEONFUTDYJSNV-UHFFFAOYSA-N 0.000 description 1
- GLZPCOQZEFWAFX-UHFFFAOYSA-N Geraniol Chemical compound CC(C)=CCCC(C)=CCO GLZPCOQZEFWAFX-UHFFFAOYSA-N 0.000 description 1
- CPELXLSAUQHCOX-UHFFFAOYSA-N Hydrogen bromide Chemical class Br CPELXLSAUQHCOX-UHFFFAOYSA-N 0.000 description 1
- DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 description 1
- WRYCSMQKUKOKBP-UHFFFAOYSA-N Imidazolidine Chemical compound C1CNCN1 WRYCSMQKUKOKBP-UHFFFAOYSA-N 0.000 description 1
- 238000000023 Kugelrohr distillation Methods 0.000 description 1
- 241000234269 Liliales Species 0.000 description 1
- NFLGAXVYCFJBMK-UHFFFAOYSA-N Menthone Chemical compound CC(C)C1CCC(C)CC1=O NFLGAXVYCFJBMK-UHFFFAOYSA-N 0.000 description 1
- ALHUZKCOMYUFRB-OAHLLOKOSA-N Muscone Chemical compound C[C@@H]1CCCCCCCCCCCCC(=O)C1 ALHUZKCOMYUFRB-OAHLLOKOSA-N 0.000 description 1
- 241000282372 Panthera onca Species 0.000 description 1
- 241000209504 Poaceae Species 0.000 description 1
- 229910004298 SiO 2 Inorganic materials 0.000 description 1
- DOOTYTYQINUNNV-UHFFFAOYSA-N Triethyl citrate Chemical compound CCOC(=O)CC(O)(C(=O)OCC)CC(=O)OCC DOOTYTYQINUNNV-UHFFFAOYSA-N 0.000 description 1
- AXMVYSVVTMKQSL-UHFFFAOYSA-N UNPD142122 Natural products OC1=CC=C(C=CC=O)C=C1O AXMVYSVVTMKQSL-UHFFFAOYSA-N 0.000 description 1
- LMETVDMCIJNNKH-UHFFFAOYSA-N [(3,7-Dimethyl-6-octenyl)oxy]acetaldehyde Chemical compound CC(C)=CCCC(C)CCOCC=O LMETVDMCIJNNKH-UHFFFAOYSA-N 0.000 description 1
- IKHGUXGNUITLKF-XPULMUKRSA-N acetaldehyde Chemical compound [14CH]([14CH3])=O IKHGUXGNUITLKF-XPULMUKRSA-N 0.000 description 1
- 150000001242 acetic acid derivatives Chemical class 0.000 description 1
- 230000009471 action Effects 0.000 description 1
- 239000013543 active substance Substances 0.000 description 1
- 150000003998 acyclic ketones Chemical class 0.000 description 1
- 230000000996 additive effect Effects 0.000 description 1
- 150000001298 alcohols Chemical class 0.000 description 1
- PFSTYGCNVAVZBK-JQGMZEBDSA-N alpha-Sinensal Chemical compound O=CC(/C)=C/CCC(/C)=C/C\C=C(/C)C=C PFSTYGCNVAVZBK-JQGMZEBDSA-N 0.000 description 1
- OGCGGWYLHSJRFY-UHFFFAOYSA-N alpha-campholenaldehyde Chemical compound CC1=CCC(CC=O)C1(C)C OGCGGWYLHSJRFY-UHFFFAOYSA-N 0.000 description 1
- 125000003277 amino group Chemical group 0.000 description 1
- 239000003963 antioxidant agent Substances 0.000 description 1
- 230000003078 antioxidant effect Effects 0.000 description 1
- 235000019568 aromas Nutrition 0.000 description 1
- 150000004982 aromatic amines Chemical class 0.000 description 1
- 238000011914 asymmetric synthesis Methods 0.000 description 1
- 230000009286 beneficial effect Effects 0.000 description 1
- WPYMKLBDIGXBTP-UHFFFAOYSA-N benzoic acid Chemical compound OC(=O)C1=CC=CC=C1 WPYMKLBDIGXBTP-UHFFFAOYSA-N 0.000 description 1
- 229960000846 camphor Drugs 0.000 description 1
- 125000004432 carbon atom Chemical group C* 0.000 description 1
- 229960000541 cetyl alcohol Drugs 0.000 description 1
- 239000007795 chemical reaction product Substances 0.000 description 1
- 239000003153 chemical reaction reagent Substances 0.000 description 1
- 238000004587 chromatography analysis Methods 0.000 description 1
- 229940117916 cinnamic aldehyde Drugs 0.000 description 1
- 229940043350 citral Drugs 0.000 description 1
- 238000003776 cleavage reaction Methods 0.000 description 1
- 238000006482 condensation reaction Methods 0.000 description 1
- 238000001816 cooling Methods 0.000 description 1
- 230000008878 coupling Effects 0.000 description 1
- 238000010168 coupling process Methods 0.000 description 1
- 238000005859 coupling reaction Methods 0.000 description 1
- 239000006071 cream Substances 0.000 description 1
- 125000004122 cyclic group Chemical group 0.000 description 1
- 150000003997 cyclic ketones Chemical class 0.000 description 1
- YKFKEYKJGVSEIX-UHFFFAOYSA-N cyclohexanone, 4-(1,1-dimethylethyl)- Chemical compound CC(C)(C)C1CCC(=O)CC1 YKFKEYKJGVSEIX-UHFFFAOYSA-N 0.000 description 1
- 230000005595 deprotonation Effects 0.000 description 1
- 238000010537 deprotonation reaction Methods 0.000 description 1
- XXJWXESWEXIICW-UHFFFAOYSA-N diethylene glycol monoethyl ether Chemical compound CCOCCOCCO XXJWXESWEXIICW-UHFFFAOYSA-N 0.000 description 1
- SZXQTJUDPRGNJN-UHFFFAOYSA-N dipropylene glycol Chemical compound OCCCOCCCO SZXQTJUDPRGNJN-UHFFFAOYSA-N 0.000 description 1
- 239000002612 dispersion medium Substances 0.000 description 1
- 238000010494 dissociation reaction Methods 0.000 description 1
- 230000005593 dissociations Effects 0.000 description 1
- WSDISUOETYTPRL-UHFFFAOYSA-N dmdm hydantoin Chemical compound CC1(C)N(CO)C(=O)N(CO)C1=O WSDISUOETYTPRL-UHFFFAOYSA-N 0.000 description 1
- 239000003995 emulsifying agent Substances 0.000 description 1
- 230000001804 emulsifying effect Effects 0.000 description 1
- 230000002708 enhancing effect Effects 0.000 description 1
- 230000007613 environmental effect Effects 0.000 description 1
- 150000002148 esters Chemical class 0.000 description 1
- 150000002170 ethers Chemical class 0.000 description 1
- 229940057975 ethyl citrate Drugs 0.000 description 1
- LYCAIKOWRPUZTN-UHFFFAOYSA-N ethylene glycol Natural products OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 1
- 238000011156 evaluation Methods 0.000 description 1
- 230000002349 favourable effect Effects 0.000 description 1
- 238000001914 filtration Methods 0.000 description 1
- 238000004508 fractional distillation Methods 0.000 description 1
- 125000000524 functional group Chemical group 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
- 239000011521 glass Substances 0.000 description 1
- 150000002391 heterocyclic compounds Chemical class 0.000 description 1
- 150000002429 hydrazines Chemical class 0.000 description 1
- 150000007857 hydrazones Chemical class 0.000 description 1
- 229930195733 hydrocarbon Natural products 0.000 description 1
- 150000003840 hydrochlorides Chemical class 0.000 description 1
- WGCNASOHLSPBMP-UHFFFAOYSA-N hydroxyacetaldehyde Natural products OCC=O WGCNASOHLSPBMP-UHFFFAOYSA-N 0.000 description 1
- 238000010952 in-situ formation Methods 0.000 description 1
- 238000010348 incorporation Methods 0.000 description 1
- 230000006698 induction Effects 0.000 description 1
- 230000001939 inductive effect Effects 0.000 description 1
- 239000000543 intermediate Substances 0.000 description 1
- 150000002499 ionone derivatives Chemical class 0.000 description 1
- 235000000396 iron Nutrition 0.000 description 1
- YJSUCBQWLKRPDL-UHFFFAOYSA-N isocyclocitral Chemical compound CC1CC(C)=CC(C)C1C=O YJSUCBQWLKRPDL-UHFFFAOYSA-N 0.000 description 1
- 125000000468 ketone group Chemical group 0.000 description 1
- 150000002596 lactones Chemical class 0.000 description 1
- 235000001510 limonene Nutrition 0.000 description 1
- 229940087305 limonene Drugs 0.000 description 1
- 239000007791 liquid phase Substances 0.000 description 1
- 230000007774 longterm Effects 0.000 description 1
- 238000005259 measurement Methods 0.000 description 1
- 229930007503 menthone Natural products 0.000 description 1
- NOUUUQMKVOUUNR-UHFFFAOYSA-N n,n'-diphenylethane-1,2-diamine Chemical compound C=1C=CC=CC=1NCCNC1=CC=CC=C1 NOUUUQMKVOUUNR-UHFFFAOYSA-N 0.000 description 1
- 230000007935 neutral effect Effects 0.000 description 1
- 150000002825 nitriles Chemical class 0.000 description 1
- QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 description 1
- QPOZUISHEWOWQL-UHFFFAOYSA-N non-8-enal Chemical compound C=CCCCCCCC=O QPOZUISHEWOWQL-UHFFFAOYSA-N 0.000 description 1
- GTDQGKWDWVUKTI-UHFFFAOYSA-N o-aminoacetophenone Chemical compound CC(=O)C1=CC=CC=C1N GTDQGKWDWVUKTI-UHFFFAOYSA-N 0.000 description 1
- 239000003921 oil Substances 0.000 description 1
- 238000006362 organocatalysis Methods 0.000 description 1
- 229910052760 oxygen Inorganic materials 0.000 description 1
- VWMVAQHMFFZQGD-UHFFFAOYSA-N p-Hydroxybenzyl acetone Natural products CC(=O)CC1=CC=C(O)C=C1 VWMVAQHMFFZQGD-UHFFFAOYSA-N 0.000 description 1
- NODGRWCMFMEGJH-UHFFFAOYSA-N p-ethylacetophenone Chemical compound CCC1=CC=C(C(C)=O)C=C1 NODGRWCMFMEGJH-UHFFFAOYSA-N 0.000 description 1
- JTJMJGYZQZDUJJ-UHFFFAOYSA-N phencyclidine Chemical class C1CCCCN1C1(C=2C=CC=CC=2)CCCCC1 JTJMJGYZQZDUJJ-UHFFFAOYSA-N 0.000 description 1
- 229940100595 phenylacetaldehyde Drugs 0.000 description 1
- 229930006728 pinane Natural products 0.000 description 1
- XOKSLPVRUOBDEW-UHFFFAOYSA-N pinane of uncertain configuration Natural products CC1CCC2C(C)(C)C1C2 XOKSLPVRUOBDEW-UHFFFAOYSA-N 0.000 description 1
- 229920000136 polysorbate Polymers 0.000 description 1
- 230000002028 premature Effects 0.000 description 1
- 239000003755 preservative agent Substances 0.000 description 1
- 230000002335 preservative effect Effects 0.000 description 1
- 150000003141 primary amines Chemical class 0.000 description 1
- 239000001294 propane Substances 0.000 description 1
- 235000010232 propyl p-hydroxybenzoate Nutrition 0.000 description 1
- 229960003415 propylparaben Drugs 0.000 description 1
- QELSKZZBTMNZEB-UHFFFAOYSA-N propylparaben Chemical compound CCCOC(=O)C1=CC=C(O)C=C1 QELSKZZBTMNZEB-UHFFFAOYSA-N 0.000 description 1
- 108090000623 proteins and genes Proteins 0.000 description 1
- 230000005588 protonation Effects 0.000 description 1
- 238000000746 purification Methods 0.000 description 1
- NJGBTKGETPDVIK-UHFFFAOYSA-N raspberry ketone Chemical compound CC(=O)CCC1=CC=C(O)C=C1 NJGBTKGETPDVIK-UHFFFAOYSA-N 0.000 description 1
- 230000009257 reactivity Effects 0.000 description 1
- 230000009467 reduction Effects 0.000 description 1
- 230000008929 regeneration Effects 0.000 description 1
- 238000011069 regeneration method Methods 0.000 description 1
- 238000011160 research Methods 0.000 description 1
- 239000008237 rinsing water Substances 0.000 description 1
- UOGMZEGKCNHMBF-UHFFFAOYSA-N scentenal Chemical compound C12CC(C=O)CC2C2CC(OC)C1C2 UOGMZEGKCNHMBF-UHFFFAOYSA-N 0.000 description 1
- 230000007017 scission Effects 0.000 description 1
- ZJMWRROPUADPEA-UHFFFAOYSA-N sec-butylbenzene Chemical compound CCC(C)C1=CC=CC=C1 ZJMWRROPUADPEA-UHFFFAOYSA-N 0.000 description 1
- 150000003335 secondary amines Chemical class 0.000 description 1
- 230000001953 sensory effect Effects 0.000 description 1
- 229910052708 sodium Inorganic materials 0.000 description 1
- 229940057950 sodium laureth sulfate Drugs 0.000 description 1
- SXHLENDCVBIJFO-UHFFFAOYSA-M sodium;2-[2-(2-dodecoxyethoxy)ethoxy]ethyl sulfate Chemical compound [Na+].CCCCCCCCCCCCOCCOCCOCCOS([O-])(=O)=O SXHLENDCVBIJFO-UHFFFAOYSA-M 0.000 description 1
- IXMINYBUNCWGER-UHFFFAOYSA-M sodium;4-propoxycarbonylphenolate Chemical compound [Na+].CCCOC(=O)C1=CC=C([O-])C=C1 IXMINYBUNCWGER-UHFFFAOYSA-M 0.000 description 1
- 241000894007 species Species 0.000 description 1
- 230000003595 spectral effect Effects 0.000 description 1
- 230000002269 spontaneous effect Effects 0.000 description 1
- 230000006641 stabilisation Effects 0.000 description 1
- 238000011105 stabilization Methods 0.000 description 1
- 238000006467 substitution reaction Methods 0.000 description 1
- 239000000758 substrate Substances 0.000 description 1
- OHEFFKYYKJVVOX-UHFFFAOYSA-N sulcatol Natural products CC(O)CCC=C(C)C OHEFFKYYKJVVOX-UHFFFAOYSA-N 0.000 description 1
- 238000004381 surface treatment Methods 0.000 description 1
- 239000000725 suspension Substances 0.000 description 1
- 230000002195 synergetic effect Effects 0.000 description 1
- 239000012209 synthetic fiber Substances 0.000 description 1
- 229920002994 synthetic fiber Polymers 0.000 description 1
- LMBFAGIMSUYTBN-MPZNNTNKSA-N teixobactin Chemical compound C([C@H](C(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@@H](CO)C(=O)N[C@H](CCC(N)=O)C(=O)N[C@H]([C@@H](C)CC)C(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@@H](CO)C(=O)N[C@H]1C(N[C@@H](C)C(=O)N[C@@H](C[C@@H]2NC(=N)NC2)C(=O)N[C@H](C(=O)O[C@H]1C)[C@@H](C)CC)=O)NC)C1=CC=CC=C1 LMBFAGIMSUYTBN-MPZNNTNKSA-N 0.000 description 1
- 150000003505 terpenes Chemical class 0.000 description 1
- LVBXEMGDVWVTGY-UHFFFAOYSA-N trans-2-octenal Natural products CCCCCC=CC=O LVBXEMGDVWVTGY-UHFFFAOYSA-N 0.000 description 1
- DKZBBWMURDFHNE-UHFFFAOYSA-N trans-coniferylaldehyde Natural products COC1=CC(C=CC=O)=CC=C1O DKZBBWMURDFHNE-UHFFFAOYSA-N 0.000 description 1
- VVGOCOMZRGWHPI-UHFFFAOYSA-N trans-hept-4-enal Natural products CCC=CCCC=O VVGOCOMZRGWHPI-UHFFFAOYSA-N 0.000 description 1
- JREYOWJEWZVAOR-UHFFFAOYSA-N triazanium;[3-methylbut-3-enoxy(oxido)phosphoryl] phosphate Chemical compound [NH4+].[NH4+].[NH4+].CC(=C)CCOP([O-])(=O)OP([O-])([O-])=O JREYOWJEWZVAOR-UHFFFAOYSA-N 0.000 description 1
- 235000013769 triethyl citrate Nutrition 0.000 description 1
- NBSLHMOSERBUOV-UHFFFAOYSA-N undecan-4-one Chemical compound CCCCCCCC(=O)CCC NBSLHMOSERBUOV-UHFFFAOYSA-N 0.000 description 1
- FGQOOHJZONJGDT-UHFFFAOYSA-N vanillin Natural products COC1=CC(O)=CC(C=O)=C1 FGQOOHJZONJGDT-UHFFFAOYSA-N 0.000 description 1
- 235000012141 vanillin Nutrition 0.000 description 1
- 239000000341 volatile oil Substances 0.000 description 1
Images
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D239/00—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings
- C07D239/02—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings
- C07D239/24—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings having three or more double bonds between ring members or between ring members and non-ring members
- C07D239/28—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings having three or more double bonds between ring members or between ring members and non-ring members with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, directly attached to ring carbon atoms
- C07D239/32—One oxygen, sulfur or nitrogen atom
- C07D239/38—One sulfur atom
- C07D239/40—One sulfur atom as doubly bound sulfur atom or as unsubstituted mercapto radical
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D239/00—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings
- C07D239/02—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings
- C07D239/04—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings having no double bonds between ring members or between ring members and non-ring members
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K8/00—Cosmetics or similar toiletry preparations
- A61K8/18—Cosmetics or similar toiletry preparations characterised by the composition
- A61K8/30—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds
- A61K8/40—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds containing nitrogen
- A61K8/41—Amines
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K8/00—Cosmetics or similar toiletry preparations
- A61K8/18—Cosmetics or similar toiletry preparations characterised by the composition
- A61K8/30—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds
- A61K8/49—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds containing heterocyclic compounds
- A61K8/494—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds containing heterocyclic compounds with more than one nitrogen as the only hetero atom
-
- 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
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D233/00—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings
- C07D233/02—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings having no double bonds between ring members or between ring members and non-ring members
-
- 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
- C11B9/0007—Aliphatic compounds
- C11B9/0015—Aliphatic compounds containing oxygen as the only heteroatom
-
- 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
- C11B9/0042—Essential oils; Perfumes compounds containing condensed hydrocarbon rings
-
- 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
- C11D3/50—Perfumes
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61Q—SPECIFIC USE OF COSMETICS OR SIMILAR TOILETRY PREPARATIONS
- A61Q15/00—Anti-perspirants or body deodorants
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61Q—SPECIFIC USE OF COSMETICS OR SIMILAR TOILETRY PREPARATIONS
- A61Q5/00—Preparations for care of the hair
- A61Q5/02—Preparations for cleaning the hair
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Life Sciences & Earth Sciences (AREA)
- Health & Medical Sciences (AREA)
- Oil, Petroleum & Natural Gas (AREA)
- Engineering & Computer Science (AREA)
- Wood Science & Technology (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Public Health (AREA)
- Veterinary Medicine (AREA)
- General Health & Medical Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- Epidemiology (AREA)
- Birds (AREA)
- Fats And Perfumes (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Detergent Compositions (AREA)
- Agricultural Chemicals And Associated Chemicals (AREA)
- Cosmetics (AREA)
Applications Claiming Priority (5)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| EP07101370 | 2007-01-30 | ||
| EP07101370.0 | 2007-01-30 | ||
| EP07116890.0 | 2007-09-21 | ||
| EP07116890 | 2007-09-21 | ||
| PCT/IB2008/050289 WO2008093272A2 (en) | 2007-01-30 | 2008-01-28 | Controlled release of active aldehydes and ketones from equilibrated dynamic mixtures |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| KR20090113260A true KR20090113260A (ko) | 2009-10-29 |
Family
ID=39564236
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| KR1020097014238A Ceased KR20090113260A (ko) | 2007-01-30 | 2008-01-28 | 활성 알데히드 및 케톤의 평형 유동 혼합물로부터의 제어 방출 |
Country Status (10)
| Country | Link |
|---|---|
| US (1) | US20100098650A1 (https=) |
| EP (1) | EP2114899B1 (https=) |
| JP (1) | JP5453112B2 (https=) |
| KR (1) | KR20090113260A (https=) |
| AT (1) | ATE482203T1 (https=) |
| BR (1) | BRPI0807022B1 (https=) |
| DE (1) | DE602008002711D1 (https=) |
| MX (1) | MX2009007714A (https=) |
| PL (1) | PL2114899T3 (https=) |
| WO (1) | WO2008093272A2 (https=) |
Families Citing this family (12)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO2010029462A1 (en) * | 2008-09-12 | 2010-03-18 | Firmenich Sa | Divinyl ether derivatives capable of releasing active aldehydes and ketones and methods of use for perfuming surfaces |
| CN102170858A (zh) * | 2008-10-21 | 2011-08-31 | 弗门尼舍有限公司 | 加香组合物及其应用 |
| ES2767877T3 (es) | 2009-06-19 | 2020-06-18 | Firmenich & Cie | Composiciones para contrarrestar el mal olor y procedimiento para su uso para contrarrestar el mal olor del sudor |
| JP5911480B2 (ja) | 2010-06-10 | 2016-04-27 | フイルメニツヒ ソシエテ アノニムＦｉｒｍｅｎｉｃｈ Ｓａ | 香料組成物及びそれらの使用 |
| CN103459573B (zh) * | 2011-04-13 | 2015-11-25 | 弗门尼舍有限公司 | 用于控制加香醛和酮的释放的平衡动态混合物 |
| WO2013060691A2 (en) | 2011-10-27 | 2013-05-02 | Firmenich Sa | Perfuming compositions and uses thereof |
| CN104125847B (zh) | 2011-11-04 | 2017-09-08 | 弗门尼舍有限公司 | 加香组合物及其用途 |
| WO2016074118A1 (en) | 2014-11-10 | 2016-05-19 | Givaudan Sa | Improvements in or relating to organic compounds |
| RU2662196C1 (ru) * | 2014-11-10 | 2018-07-24 | Живодан Са | Усовершенствование органических соединений или усовершенствование, относящееся к органическим соединениям |
| EP3533786A1 (en) | 2018-03-02 | 2019-09-04 | Givaudan SA | Thioether precursors for fragrant ketones and aldehydes |
| EP4034073A1 (en) * | 2019-12-20 | 2022-08-03 | Firmenich SA | Pro-perfume compositions |
| CN115926893B (zh) * | 2021-10-20 | 2024-06-25 | 中国科学院化学研究所 | 一种可循环利用的清洗剂及其制备方法与应用 |
Family Cites Families (10)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPS58141225A (ja) * | 1982-02-16 | 1983-08-22 | Takasago Corp | 芳香材用樹脂組成物 |
| EP0571677A1 (en) * | 1992-05-29 | 1993-12-01 | Unilever Plc | Aqueous parfume oil microemulsions |
| US6096704A (en) * | 1997-03-21 | 2000-08-01 | Bryant, Jr.; Lonnie Liddell | Pro-fragrance compound |
| EP0971021A1 (en) * | 1998-07-10 | 2000-01-12 | The Procter & Gamble Company | Process for producing particles of amine reaction product |
| EP0971027A1 (en) * | 1998-07-10 | 2000-01-12 | The Procter & Gamble Company | Amine reaction compounds comprising one or more active ingredient |
| US6790815B1 (en) * | 1998-07-10 | 2004-09-14 | Procter & Gamble Company | Amine reaction compounds comprising one or more active ingredient |
| EP0971025A1 (en) * | 1998-07-10 | 2000-01-12 | The Procter & Gamble Company | Amine reaction compounds comprising one or more active ingredient |
| US7129204B2 (en) * | 2000-06-02 | 2006-10-31 | Quest International Services B.V. | Perfumes |
| MX2007001265A (es) * | 2004-08-05 | 2007-09-14 | Firmenich & Cie | Uso de mezclas dinamicas para una liberacion controlada de fragancias. |
| DE102005062175A1 (de) * | 2005-12-23 | 2007-06-28 | Henkel Kgaa | Cyclische Aminale als Duftstoffe |
-
2008
- 2008-01-28 PL PL08702535T patent/PL2114899T3/pl unknown
- 2008-01-28 WO PCT/IB2008/050289 patent/WO2008093272A2/en not_active Ceased
- 2008-01-28 AT AT08702535T patent/ATE482203T1/de not_active IP Right Cessation
- 2008-01-28 US US12/523,964 patent/US20100098650A1/en not_active Abandoned
- 2008-01-28 JP JP2009547787A patent/JP5453112B2/ja not_active Expired - Fee Related
- 2008-01-28 DE DE602008002711T patent/DE602008002711D1/de active Active
- 2008-01-28 EP EP08702535A patent/EP2114899B1/en active Active
- 2008-01-28 BR BRPI0807022A patent/BRPI0807022B1/pt not_active IP Right Cessation
- 2008-01-28 KR KR1020097014238A patent/KR20090113260A/ko not_active Ceased
- 2008-01-28 MX MX2009007714A patent/MX2009007714A/es active IP Right Grant
Also Published As
| Publication number | Publication date |
|---|---|
| BRPI0807022B1 (pt) | 2016-06-14 |
| US20100098650A1 (en) | 2010-04-22 |
| JP2010516804A (ja) | 2010-05-20 |
| DE602008002711D1 (de) | 2010-11-04 |
| BRPI0807022A2 (pt) | 2015-06-16 |
| EP2114899A2 (en) | 2009-11-11 |
| WO2008093272A2 (en) | 2008-08-07 |
| WO2008093272A3 (en) | 2008-10-09 |
| EP2114899B1 (en) | 2010-09-22 |
| MX2009007714A (es) | 2009-12-14 |
| JP5453112B2 (ja) | 2014-03-26 |
| PL2114899T3 (pl) | 2011-02-28 |
| ATE482203T1 (de) | 2010-10-15 |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| KR20090113260A (ko) | 활성 알데히드 및 케톤의 평형 유동 혼합물로부터의 제어 방출 | |
| CN101679290B (zh) | 能释放活性醛或酮的3元至7元1,3-二氮杂-4-氧代-杂环衍生物 | |
| KR20090024701A (ko) | 향료 화합물 | |
| US8124578B2 (en) | Use of dynamic mixtures for a controlled release of fragrances | |
| CN102149664A (zh) | 能释放活性醛和活性酮的二乙烯基醚衍生物及用于给表面加香的方法 | |
| US10508252B2 (en) | Photolabile acetal and ketal compounds for the controlled release of active volatile carbonyl compounds | |
| EP2697347B1 (en) | Equilibrated dynamic mixtures to control the release of perfuming aldehydes and ketones | |
| CN101605765B (zh) | 活性醛和酮从平衡的动态混合物中的受控释放 | |
| US20100226875A1 (en) | Controlled release of active compounds from dynamic mixtures | |
| JP2016513101A (ja) | フローラルなにおい物質としてのピラン |
Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| PA0105 | International application |
Patent event date: 20090708 Patent event code: PA01051R01D Comment text: International Patent Application |
|
| PG1501 | Laying open of application | ||
| A201 | Request for examination | ||
| PA0201 | Request for examination |
Patent event code: PA02012R01D Patent event date: 20121203 Comment text: Request for Examination of Application |
|
| E902 | Notification of reason for refusal | ||
| PE0902 | Notice of grounds for rejection |
Comment text: Notification of reason for refusal Patent event date: 20140120 Patent event code: PE09021S01D |
|
| E601 | Decision to refuse application | ||
| PE0601 | Decision on rejection of patent |
Patent event date: 20140627 Comment text: Decision to Refuse Application Patent event code: PE06012S01D Patent event date: 20140120 Comment text: Notification of reason for refusal Patent event code: PE06011S01I |