JP2022517714A - 匂い物質として有用なアセタート化合物 - Google Patents
匂い物質として有用なアセタート化合物 Download PDFInfo
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- JP2022517714A JP2022517714A JP2021526223A JP2021526223A JP2022517714A JP 2022517714 A JP2022517714 A JP 2022517714A JP 2021526223 A JP2021526223 A JP 2021526223A JP 2021526223 A JP2021526223 A JP 2021526223A JP 2022517714 A JP2022517714 A JP 2022517714A
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- JP
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- Prior art keywords
- methyl
- cyclopropyl
- trimethylbicyclo
- carbon
- formula
- 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.)
- Granted
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- 239000003205 fragrance Substances 0.000 title claims abstract description 25
- 150000001242 acetic acid derivatives Chemical class 0.000 title 1
- 239000000203 mixture Substances 0.000 claims abstract description 27
- 150000001875 compounds Chemical class 0.000 claims description 31
- -1 hexa-3-yl Chemical group 0.000 claims description 23
- 125000001559 cyclopropyl group Chemical group [H]C1([H])C([H])([H])C1([H])* 0.000 claims description 21
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 claims description 19
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 19
- 229910052799 carbon Inorganic materials 0.000 claims description 10
- 150000001721 carbon Chemical group 0.000 claims description 9
- 229910052739 hydrogen Inorganic materials 0.000 claims description 6
- 239000001257 hydrogen Substances 0.000 claims description 6
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 5
- 239000011203 carbon fibre reinforced carbon Substances 0.000 claims description 5
- ORWLYMDBVHPWKD-UHFFFAOYSA-N 1,2,2-trimethylbicyclo[3.1.0]hexane Chemical compound C1CC(C)(C)C2(C)C1C2 ORWLYMDBVHPWKD-UHFFFAOYSA-N 0.000 claims 1
- PORLPQOBGIOIEL-PTSYSSFESA-N CC(C(=O)O)C1(CC1C[C@@H]2C[C@@H]3C[C@@]3(C2(C)C)C)C Chemical compound CC(C(=O)O)C1(CC1C[C@@H]2C[C@@H]3C[C@@]3(C2(C)C)C)C PORLPQOBGIOIEL-PTSYSSFESA-N 0.000 claims 1
- 235000008632 Santalum album Nutrition 0.000 abstract description 8
- QTBSBXVTEAMEQO-UHFFFAOYSA-M Acetate Chemical compound CC([O-])=O QTBSBXVTEAMEQO-UHFFFAOYSA-M 0.000 abstract description 3
- 241000221035 Santalaceae Species 0.000 abstract 1
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 8
- UHOVQNZJYSORNB-MZWXYZOWSA-N benzene-d6 Chemical compound [2H]C1=C([2H])C([2H])=C([2H])C([2H])=C1[2H] UHOVQNZJYSORNB-MZWXYZOWSA-N 0.000 description 8
- 240000000513 Santalum album Species 0.000 description 7
- KXKVLQRXCPHEJC-UHFFFAOYSA-N acetic acid trimethyl ester Natural products COC(C)=O KXKVLQRXCPHEJC-UHFFFAOYSA-N 0.000 description 7
- 239000003921 oil Substances 0.000 description 6
- 235000019198 oils Nutrition 0.000 description 6
- 239000002936 woody odorant Substances 0.000 description 5
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- 238000004821 distillation Methods 0.000 description 4
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- ZRSNZINYAWTAHE-UHFFFAOYSA-N p-methoxybenzaldehyde Chemical compound COC1=CC=C(C=O)C=C1 ZRSNZINYAWTAHE-UHFFFAOYSA-N 0.000 description 4
- RNLHVODSMDJCBR-SOFGYWHQSA-N (e)-3-methyl-5-(2,2,3-trimethylcyclopent-3-en-1-yl)pent-4-en-2-ol Chemical compound CC(O)C(C)\C=C\C1CC=C(C)C1(C)C RNLHVODSMDJCBR-SOFGYWHQSA-N 0.000 description 3
- NLZUEZXRPGMBCV-UHFFFAOYSA-N Butylhydroxytoluene Chemical compound CC1=CC(C(C)(C)C)=C(O)C(C(C)(C)C)=C1 NLZUEZXRPGMBCV-UHFFFAOYSA-N 0.000 description 3
- PORLPQOBGIOIEL-UHFFFAOYSA-N CC(C1(C)C(CC2C(C)(C)C(C)(C3)C3C2)C1)C(O)=O Chemical compound CC(C1(C)C(CC2C(C)(C)C(C)(C3)C3C2)C1)C(O)=O PORLPQOBGIOIEL-UHFFFAOYSA-N 0.000 description 3
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 3
- 239000004615 ingredient Substances 0.000 description 3
- 150000002576 ketones Chemical class 0.000 description 3
- 238000000034 method Methods 0.000 description 3
- JYVLIDXNZAXMDK-UHFFFAOYSA-N pentan-2-ol Chemical compound CCCC(C)O JYVLIDXNZAXMDK-UHFFFAOYSA-N 0.000 description 3
- PHXATPHONSXBIL-UHFFFAOYSA-N xi-gamma-Undecalactone Chemical compound CCCCCCCC1CCC(=O)O1 PHXATPHONSXBIL-UHFFFAOYSA-N 0.000 description 3
- CRDAMVZIKSXKFV-GNESMGCMSA-N (2-trans,6-cis)-farnesol Chemical compound CC(C)=CCC\C(C)=C/CC\C(C)=C\CO CRDAMVZIKSXKFV-GNESMGCMSA-N 0.000 description 2
- GLZPCOQZEFWAFX-JXMROGBWSA-N (E)-Geraniol Chemical compound CC(C)=CCC\C(C)=C\CO GLZPCOQZEFWAFX-JXMROGBWSA-N 0.000 description 2
- 238000001644 13C nuclear magnetic resonance spectroscopy Methods 0.000 description 2
- 238000005160 1H NMR spectroscopy Methods 0.000 description 2
- QZFSNJAQFWEXEA-UHFFFAOYSA-N 3,3-dimethyl-5-(2,2,3-trimethylcyclopent-3-en-1-yl)pent-4-en-2-ol Chemical compound CC(O)C(C)(C)C=CC1CC=C(C)C1(C)C QZFSNJAQFWEXEA-UHFFFAOYSA-N 0.000 description 2
- NGYMOTOXXHCHOC-UHFFFAOYSA-N 3-methyl-5-(2,2,3-trimethylcyclopent-3-en-1-yl)pentan-2-ol Chemical compound CC(O)C(C)CCC1CC=C(C)C1(C)C NGYMOTOXXHCHOC-UHFFFAOYSA-N 0.000 description 2
- HIQIXEFWDLTDED-UHFFFAOYSA-N 4-hydroxy-1-piperidin-4-ylpyrrolidin-2-one Chemical compound O=C1CC(O)CN1C1CCNCC1 HIQIXEFWDLTDED-UHFFFAOYSA-N 0.000 description 2
- GHBSPIPJMLAMEP-UHFFFAOYSA-N 6-pentyloxan-2-one Chemical compound CCCCCC1CCCC(=O)O1 GHBSPIPJMLAMEP-UHFFFAOYSA-N 0.000 description 2
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 2
- 241000723438 Cercidiphyllum japonicum Species 0.000 description 2
- FKUPPRZPSYCDRS-UHFFFAOYSA-N Cyclopentadecanolide Chemical compound O=C1CCCCCCCCCCCCCCO1 FKUPPRZPSYCDRS-UHFFFAOYSA-N 0.000 description 2
- GLZPCOQZEFWAFX-UHFFFAOYSA-N Geraniol Chemical compound CC(C)=CCCC(C)=CCO GLZPCOQZEFWAFX-UHFFFAOYSA-N 0.000 description 2
- QIGBRXMKCJKVMJ-UHFFFAOYSA-N Hydroquinone Chemical compound OC1=CC=C(O)C=C1 QIGBRXMKCJKVMJ-UHFFFAOYSA-N 0.000 description 2
- DOOTYTYQINUNNV-UHFFFAOYSA-N Triethyl citrate Chemical compound CCOC(=O)CC(O)(C(=O)OCC)CC(=O)OCC DOOTYTYQINUNNV-UHFFFAOYSA-N 0.000 description 2
- 150000001241 acetals Chemical class 0.000 description 2
- 229940022663 acetate Drugs 0.000 description 2
- WETWJCDKMRHUPV-UHFFFAOYSA-N acetyl chloride Chemical compound CC(Cl)=O WETWJCDKMRHUPV-UHFFFAOYSA-N 0.000 description 2
- 239000012346 acetyl chloride Substances 0.000 description 2
- 230000021736 acetylation Effects 0.000 description 2
- 238000006640 acetylation reaction Methods 0.000 description 2
- 239000002671 adjuvant Substances 0.000 description 2
- 150000001299 aldehydes Chemical class 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
- 239000003963 antioxidant agent Substances 0.000 description 2
- QUKGYYKBILRGFE-UHFFFAOYSA-N benzyl acetate Chemical compound CC(=O)OCC1=CC=CC=C1 QUKGYYKBILRGFE-UHFFFAOYSA-N 0.000 description 2
- 239000012876 carrier material Substances 0.000 description 2
- GUDMZGLFZNLYEY-UHFFFAOYSA-N cyclopropylmethanol Chemical compound OCC1CC1 GUDMZGLFZNLYEY-UHFFFAOYSA-N 0.000 description 2
- IFYYFLINQYPWGJ-UHFFFAOYSA-N gamma-decalactone Chemical compound CCCCCCC1CCC(=O)O1 IFYYFLINQYPWGJ-UHFFFAOYSA-N 0.000 description 2
- FXHGMKSSBGDXIY-UHFFFAOYSA-N heptanal Chemical compound CCCCCCC=O FXHGMKSSBGDXIY-UHFFFAOYSA-N 0.000 description 2
- UFLHIIWVXFIJGU-UHFFFAOYSA-N hex-3-en-1-ol Natural products CCC=CCCO UFLHIIWVXFIJGU-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
- 150000002596 lactones Chemical class 0.000 description 2
- CDOSHBSSFJOMGT-UHFFFAOYSA-N linalool Chemical compound CC(C)=CCCC(C)(O)C=C CDOSHBSSFJOMGT-UHFFFAOYSA-N 0.000 description 2
- 239000000463 material Substances 0.000 description 2
- ZOCHHNOQQHDWHG-UHFFFAOYSA-N n-hexan-3-ol Natural products CCCC(O)CC ZOCHHNOQQHDWHG-UHFFFAOYSA-N 0.000 description 2
- XNGIFLGASWRNHJ-UHFFFAOYSA-N phthalic acid Chemical compound OC(=O)C1=CC=CC=C1C(O)=O XNGIFLGASWRNHJ-UHFFFAOYSA-N 0.000 description 2
- 239000000047 product Substances 0.000 description 2
- 238000000746 purification Methods 0.000 description 2
- CZCBTSFUTPZVKJ-UHFFFAOYSA-N rose oxide Chemical compound CC1CCOC(C=C(C)C)C1 CZCBTSFUTPZVKJ-UHFFFAOYSA-N 0.000 description 2
- 230000001953 sensory effect Effects 0.000 description 2
- VMYFZRTXGLUXMZ-UHFFFAOYSA-N triethyl citrate Natural products CCOC(=O)C(O)(C(=O)OCC)C(=O)OCC VMYFZRTXGLUXMZ-UHFFFAOYSA-N 0.000 description 2
- 239000001069 triethyl citrate Substances 0.000 description 2
- 235000013769 triethyl citrate Nutrition 0.000 description 2
- 239000000341 volatile oil Substances 0.000 description 2
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 2
- GVJHHUAWPYXKBD-IEOSBIPESA-N α-tocopherol Chemical compound OC1=C(C)C(C)=C2O[C@@](CCC[C@H](C)CCC[C@H](C)CCCC(C)C)(C)CCC2=C1C GVJHHUAWPYXKBD-IEOSBIPESA-N 0.000 description 2
- NOOLISFMXDJSKH-UTLUCORTSA-N (+)-Neomenthol Chemical compound CC(C)[C@@H]1CC[C@@H](C)C[C@@H]1O NOOLISFMXDJSKH-UTLUCORTSA-N 0.000 description 1
- ORHSGDMSYGKJJY-SAIIYOCFSA-N (1'r,6's)-2,2,4',7',7'-pentamethylspiro[1,3-dioxane-5,5'-bicyclo[4.1.0]heptane] Chemical compound C12([C@H]3[C@H](C3(C)C)CCC2C)COC(C)(C)OC1 ORHSGDMSYGKJJY-SAIIYOCFSA-N 0.000 description 1
- 239000000260 (2E,6E)-3,7,11-trimethyldodeca-2,6,10-trien-1-ol Substances 0.000 description 1
- AVJMJMPVWWWELJ-DHZHZOJOSA-N (2e)-1-methoxy-3,7-dimethylocta-2,6-diene Chemical compound COC\C=C(/C)CCC=C(C)C AVJMJMPVWWWELJ-DHZHZOJOSA-N 0.000 description 1
- 239000001490 (3R)-3,7-dimethylocta-1,6-dien-3-ol Substances 0.000 description 1
- 239000001724 (4,8-dimethyl-2-propan-2-ylidene-3,3a,4,5,6,8a-hexahydro-1H-azulen-6-yl) acetate Substances 0.000 description 1
- OOCCDEMITAIZTP-QPJJXVBHSA-N (E)-cinnamyl alcohol Chemical compound OC\C=C\C1=CC=CC=C1 OOCCDEMITAIZTP-QPJJXVBHSA-N 0.000 description 1
- QMVPMAAFGQKVCJ-SNVBAGLBSA-N (R)-(+)-citronellol Natural products OCC[C@H](C)CCC=C(C)C QMVPMAAFGQKVCJ-SNVBAGLBSA-N 0.000 description 1
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- 239000000267 (Z)-hex-3-en-1-ol Substances 0.000 description 1
- GTLKSTALFRGBQG-NYYWCZLTSA-N (e)-6-ethyl-3-methyloct-6-en-1-ol Chemical compound CC\C(=C/C)CCC(C)CCO GTLKSTALFRGBQG-NYYWCZLTSA-N 0.000 description 1
- KVDORLFQOZGRPI-CHNJZELVSA-N (z)-hex-3-en-1-ol Chemical compound CC\C=C/CCO.CC\C=C/CCO KVDORLFQOZGRPI-CHNJZELVSA-N 0.000 description 1
- BVDMQAQCEBGIJR-UHFFFAOYSA-N 1-(2,2,6-trimethylcyclohexyl)hexan-3-ol Chemical compound CCCC(O)CCC1C(C)CCCC1(C)C BVDMQAQCEBGIJR-UHFFFAOYSA-N 0.000 description 1
- VPKMGDRERYMTJX-CMDGGOBGSA-N 1-(2,6,6-Trimethyl-2-cyclohexen-1-yl)-1-penten-3-one Chemical compound CCC(=O)\C=C\C1C(C)=CCCC1(C)C VPKMGDRERYMTJX-CMDGGOBGSA-N 0.000 description 1
- IANQTJSKSUMEQM-UHFFFAOYSA-N 1-benzofuran Chemical compound C1=CC=C2OC=CC2=C1 IANQTJSKSUMEQM-UHFFFAOYSA-N 0.000 description 1
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- 239000010656 jasmine oil Substances 0.000 description 1
- 239000000171 lavandula angustifolia l. flower oil Substances 0.000 description 1
- 238000004519 manufacturing process Methods 0.000 description 1
- KVWWIYGFBYDJQC-UHFFFAOYSA-N methyl dihydrojasmonate Chemical compound CCCCCC1C(CC(=O)OC)CCC1=O KVWWIYGFBYDJQC-UHFFFAOYSA-N 0.000 description 1
- 229930014626 natural product Natural products 0.000 description 1
- 230000007935 neutral effect Effects 0.000 description 1
- 229910052757 nitrogen Inorganic materials 0.000 description 1
- 239000012044 organic layer Substances 0.000 description 1
- 229940037201 oris Drugs 0.000 description 1
- WCVRQHFDJLLWFE-UHFFFAOYSA-N pentane-1,2-diol Chemical compound CCCC(O)CO WCVRQHFDJLLWFE-UHFFFAOYSA-N 0.000 description 1
- 239000000546 pharmaceutical excipient Substances 0.000 description 1
- 229940067107 phenylethyl alcohol Drugs 0.000 description 1
- 239000001738 pogostemon cablin oil Substances 0.000 description 1
- 238000002360 preparation method Methods 0.000 description 1
- 238000002953 preparative HPLC Methods 0.000 description 1
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 150000003222 pyridines Chemical class 0.000 description 1
- 239000011541 reaction mixture Substances 0.000 description 1
- 238000010992 reflux Methods 0.000 description 1
- 239000010666 rose oil Substances 0.000 description 1
- 235000019719 rose oil Nutrition 0.000 description 1
- 229930007790 rose oxide Natural products 0.000 description 1
- 239000010671 sandalwood oil Substances 0.000 description 1
- 239000001290 saussurea lappa clarke root oil Substances 0.000 description 1
- 238000000926 separation method Methods 0.000 description 1
- 239000007787 solid Substances 0.000 description 1
- 230000000707 stereoselective effect Effects 0.000 description 1
- 238000003860 storage Methods 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 239000000758 substrate Substances 0.000 description 1
- 238000003786 synthesis reaction Methods 0.000 description 1
- 229940116411 terpineol Drugs 0.000 description 1
- LFSYLMRHJKGLDV-UHFFFAOYSA-N tetradecanolide Natural products O=C1CCCCCCCCCCCCCO1 LFSYLMRHJKGLDV-UHFFFAOYSA-N 0.000 description 1
- 229960001295 tocopherol Drugs 0.000 description 1
- 229930003799 tocopherol Natural products 0.000 description 1
- 235000010384 tocopherol Nutrition 0.000 description 1
- 239000011732 tocopherol Substances 0.000 description 1
- CRDAMVZIKSXKFV-UHFFFAOYSA-N trans-Farnesol Natural products CC(C)=CCCC(C)=CCCC(C)=CCO CRDAMVZIKSXKFV-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
- MWOOGOJBHIARFG-UHFFFAOYSA-N vanillin Chemical compound COC1=CC(C=O)=CC=C1O MWOOGOJBHIARFG-UHFFFAOYSA-N 0.000 description 1
- 235000012141 vanillin Nutrition 0.000 description 1
- 239000011701 zinc Substances 0.000 description 1
- 229910052725 zinc Inorganic materials 0.000 description 1
Classifications
-
- 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
- C11B9/0046—Essential oils; Perfumes compounds containing condensed hydrocarbon rings containing only two condensed rings
- C11B9/0049—Essential oils; Perfumes compounds containing condensed hydrocarbon rings containing only two condensed rings the condensed rings sharing two common C atoms
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C69/00—Esters of carboxylic acids; Esters of carbonic or haloformic acids
- C07C69/02—Esters of acyclic saturated monocarboxylic acids having the carboxyl group bound to an acyclic carbon atom or to hydrogen
- C07C69/12—Acetic acid esters
- C07C69/14—Acetic acid esters of monohydroxylic compounds
-
- 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
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C2601/00—Systems containing only non-condensed rings
- C07C2601/02—Systems containing only non-condensed rings with a three-membered ring
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C2602/00—Systems containing two condensed rings
- C07C2602/02—Systems containing two condensed rings the rings having only two atoms in common
- C07C2602/14—All rings being cycloaliphatic
- C07C2602/18—All rings being cycloaliphatic the ring system containing six carbon atoms
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Life Sciences & Earth Sciences (AREA)
- Engineering & Computer Science (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Oil, Petroleum & Natural Gas (AREA)
- Wood Science & Technology (AREA)
- Fats And Perfumes (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Abstract
Description
R1およびR2はそれらが結合している炭素原子と一緒にシクロプロピルまたは二重結合を形成するか、またはR1およびR2は水素であり;および
R3およびR4はそれらが結合している炭素原子と一緒にシクロプロピルまたは二重結合を形成し、および点線が炭素-炭素結合と一緒に単結合を形成するか;または
R3およびR4は水素であり、および点線が炭素-炭素結合と一緒に二重結合を形成する、
で表される化合物が提供される。
(E)-2-メチル-4-(1,2,2-トリメチルビシクロ[3.1.0]ヘキサン-3-イル)ブタ-2-エン-1-イルアセタート;
(E)-2-メチル-4-(1,2,2-トリメチルビシクロ[3.1.0]ヘキサン-3-イル)ブタ-3-エン-1-イルアセタート,
(E)-2-メチル-4-(2,2,3-トリメチルシクロペンチル)ブタ-3-エン-1-イルアセタート;
(E)-2-メチル-4-(2,2,3-トリメチルシクロペンチル)ブタ-2-エン-1-イルアセタート;
(E)-2-メチル-4-(2,2,3-トリメチルシクロペンタ-3-エン-1-イル)ブタ-3-エン-1-イルアセタート;
(E)-2-メチル-4-(2,2,3-トリメチルシクロペンタ-3-エン-1-イル)ブタ-2-エン-1-イルアセタート;
(1-メチル-2-((2,2,3-トリメチルシクロペンタ-3-エン-1-イル)メチル)シクロプロピル)メチルアセタート;および
(1-メチル-2-((2,2,3-トリメチルシクロペンチル)メチル)シクロプロピル)メチルアセタート
から選択される式(I)で表される化合物である。
本明細書に使用されるとき、「担体材料」は、匂い物質の観点から実際的に中性である材料、すなわち、匂い物質の官能特性を有意に変化させない材料を意味する。
- 精油および抽出物、例として、海狸香、コスタスルート油(costus root oil)、オークモスアブソリュート、ゼラニウム油、ツリーモスアブソリュート、バジル油、果実油、たとえばベルガモット油およびマンダリン油など、ミルテ油、パルマローザ油、パッチュリ油、プチグレン油、ジャスミン油、バラ油、サンダルウッド油、アブサン油、ラベンダー油および/またはイランイラン油;
- エステルおよびラクトン、例として、ベンジルアセタート;セドリルアセタート((1S,6R,8aR)-1,4,4,6-テトラメチルオクタヒドロ-1H-5,8a-メタノアズレン-6-イルアセタート);γ-デカラクトン(6-ペンチルテトラヒドロ-2H-ピラン-2-オン);Helvetolide(登録商標)(2-(1-(3,3-ジメチルシクロヘキシル)エトキシ)-2-メチルプロピルプロピオナート);γ-ウンデカラクトン(5-へプチルオキソラン-2-オン);および/またはベチベリルアセタート((4,8-ジメチル-2-プロパン-2-イリデン-3,3a,4,5,6,8a-ヘキサヒドロ-1H-アズレン-6-イル)アセタート);
- 複素環化合物、例として、イソブチルキノリン(2-イソブチルキノリン)。
1つの特具体的な態様において、式(I)で表される化合物は(1-メチル-2-((1,2,2-トリメチルビシクロ[3.1.0]ヘキサン-3-イル)メチル)シクロプロピル)メチルアセタートであり、および他のウッディ匂い物質が(1-メチル-2-(((1S,3R,5R)-1,2,2-トリメチルビシクロ[3.1.0]ヘキサン-3-イル)メチル)-シクロプロピル)メタノールであり、これは0.05:99.95~99.95:0.05(例として、0.1:99.5~5:95(0.2:99.8;0.3:99.7、0.4:99.6を包含する)の範囲で組み合わせてもよい。
還流冷却器を備えた反応器に、1-メチル-2-[[(1S,3R,5R)-1,2,2-トリメチルビシクロ[3.1.0]ヘキサ-3-イル]メチル]シクロプロパンメタノール)(ジアステレオマーの混合物;異性体1:40.9%;異性体2:53.4%;50g;純度:94.3%;212mmol)、ピリジン(20g;253mmol)、およびトルエン(200g)を窒素下でチャージした。0℃で撹拌した混合物に、塩化アセチル(18g;229mmol)を15分以内に滴加した。結果として生じる反応混合物を20℃まで上昇させ、さらに2時間撹拌した。水を添加した。有機層を分離し、洗浄し(水)、ロータリーエバポレーター蒸留(60℃;10mbar)により濃縮して、90%の(1-メチル-2-(((1S,3R,5R)-1,2,2-トリメチルビシクロ[3.1.0]ヘキサン-3-イル)メチル)シクロプロピル)-メチルアセタートを含有する帯黄色の油58gを得た。
匂い記載:ソフトフルーティーフローラル面(バイオレット/オリス方向)を有する、ソフトな、ウッディ、クリーミー、サンダルウッド特徴
13C NMR (C6D6, 150 MHz): 170.0, 73.2, 45.1, 41.1, 32.4, 31.2, 29.5, 22.8, 22.75, 21.4, 20.3, 19.5, 18.7, 17.4, 17.3, 15.3, 14.0
1.04 (s, 3H), 1.00-0.97 (m, 1H), 0.93 (s, 3H), 0.74 (s, 3H), 0.54-0.47 (m, 3H), 0.06 (dd, J = 7.9, 4.9, 1H), -0.18 (br t, J = 4.5, 1H).
13C NMR (C6D6, 150 MHz): 170.0, 73.2, 44.8, 41.1, 32.2, 31.3, 28.8, 22.8, 22.6, 21.9, 20.2, 19.6, 19.6, 17.2, 16.8, 15.9, 13.9
Claims (10)
- R1とR2および/またはR3とR4はそれらが結合している炭素原子と一緒にシクロプロピルを形成する、請求項1に記載の化合物。
- 化合物が、その立体異性体のいずれか1つの形態であるか、またはそれらの混合物である、(1-メチル-2-((1,2,2-トリメチルビシクロ[3.1.0]ヘキサン-3-イル)メチル)シクロプロピル)-メチルアセタートである、請求項2に記載の化合物。
- 化合物が、(1-メチル-2-(((1S,3R,5R)-1,2,2-トリメチルビシクロ[3.1.0]ヘキサン-3-イル)メチル)シクロプロピル)-メチルアセタートである、請求項3に記載の化合物。
- a)請求項1または2において定義される少なくとも1つの式(I)で表される化合物、および
b)その立体異性体のいずれか1つの形態の[1-メチル-2-[(1,2,2-トリメチルビシクロ[3.1.0]ヘキサ-3-イル)メチル]シクロプロピル]メタノールまたはそれらの混合物、
を含む、またはそれらからなる、フレグランス組成物。 - 式(I)で表される化合物が(1-メチル-2-(((1S,3R,5R)-1,2,2-トリメチルビシクロ[3.1.0]ヘキサン-3-イル)メチル)シクロプロピル)-メチルアセタート(成分a))であり、および成分b)が[1-メチル-2-[((1S,3R,5R)-1,2,2-トリメチルビシクロ[3.1.0]ヘキサ-3-イル)メチル]シクロプロピル]メタノールである、請求項5に記載のフレグランス組成物。
- 成分a)対b)の重量比が0.05:99.95~5:95(a:b)の範囲にあることを特徴とする、請求項5または請求項6に記載のフレグランス組成物。
- 請求項1に定義される式(I)で表される化合物、または請求項5、請求項6または請求項7に定義されるフレグランス組成物、および消費者製品ベースを含む消費者製品。
- 嗅覚許容量の、請求項1に定義される式(I)で表される化合物または請求項3~5のいずれか一項に定義されるフレグランス組成物を添加することによって、消費者製品ベースを改善、増強または改変する方法。
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Citations (3)
Publication number | Priority date | Publication date | Assignee | Title |
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JPS554374A (en) * | 1978-06-26 | 1980-01-12 | Dragoco Gerberding Co Gmbh | Multiisubstituted cyclopentene derivative |
JP2000512663A (ja) * | 1996-02-21 | 2000-09-26 | ジボーダン―ルール(アンテルナシヨナル)ソシエテ アノニム | フレイグランス先駆体 |
WO2015163023A1 (ja) * | 2014-04-21 | 2015-10-29 | 高砂香料工業株式会社 | 新規化合物及び該化合物を含有する香料組成物 |
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CH566113A5 (ja) | 1973-02-09 | 1975-09-15 | Firmenich & Cie | |
EP0801049B1 (en) | 1996-04-09 | 2001-11-21 | Givaudan SA | Cyclopentanebutanol derivatives as odorants |
GB0620556D0 (en) | 2006-10-18 | 2006-11-22 | Givauden Sa | Organic compounds |
US20110311469A1 (en) | 2009-03-24 | 2011-12-22 | Pamingle Herve | Alcohol as sandalwood odorant |
DE102010002104A1 (de) * | 2010-02-18 | 2011-08-18 | Henkel AG & Co. KGaA, 40589 | Parfümzusammensetzung |
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Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
JPS554374A (en) * | 1978-06-26 | 1980-01-12 | Dragoco Gerberding Co Gmbh | Multiisubstituted cyclopentene derivative |
JP2000512663A (ja) * | 1996-02-21 | 2000-09-26 | ジボーダン―ルール(アンテルナシヨナル)ソシエテ アノニム | フレイグランス先駆体 |
WO2015163023A1 (ja) * | 2014-04-21 | 2015-10-29 | 高砂香料工業株式会社 | 新規化合物及び該化合物を含有する香料組成物 |
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