JP2014108970A - 香料組成物 - Google Patents
香料組成物 Download PDFInfo
- Publication number
- JP2014108970A JP2014108970A JP2012262669A JP2012262669A JP2014108970A JP 2014108970 A JP2014108970 A JP 2014108970A JP 2012262669 A JP2012262669 A JP 2012262669A JP 2012262669 A JP2012262669 A JP 2012262669A JP 2014108970 A JP2014108970 A JP 2014108970A
- Authority
- JP
- Japan
- Prior art keywords
- fragrance
- dimethyl
- octen
- examples
- ether
- 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
Links
- 239000000203 mixture Substances 0.000 title claims abstract description 54
- 239000002304 perfume Substances 0.000 title abstract description 14
- 239000003205 fragrance Substances 0.000 claims abstract description 84
- UATRONWBYDQKSQ-UHFFFAOYSA-N 3-methyl-1-(3-methylbut-2-enoxy)but-2-ene Chemical compound CC(C)=CCOCC=C(C)C UATRONWBYDQKSQ-UHFFFAOYSA-N 0.000 claims abstract description 32
- VIZNHPNZAZKEPF-UHFFFAOYSA-N 4,7-dimethyloct-6-en-3-ol Chemical compound CCC(O)C(C)CC=C(C)C VIZNHPNZAZKEPF-UHFFFAOYSA-N 0.000 claims abstract description 31
- FDPIMTJIUBPUKL-UHFFFAOYSA-N pentan-3-one Chemical compound CCC(=O)CC FDPIMTJIUBPUKL-UHFFFAOYSA-N 0.000 claims abstract description 22
- 238000004519 manufacturing process Methods 0.000 claims abstract description 18
- JKXQKGNGJVZKFA-UHFFFAOYSA-N 1-chloro-3-methylbut-2-ene Chemical compound CC(C)=CCCl JKXQKGNGJVZKFA-UHFFFAOYSA-N 0.000 claims abstract description 11
- 238000007259 addition reaction Methods 0.000 claims abstract description 11
- 239000002537 cosmetic Substances 0.000 claims description 9
- 238000006722 reduction reaction Methods 0.000 claims description 6
- 238000006243 chemical reaction Methods 0.000 abstract description 9
- 230000002829 reductive effect Effects 0.000 abstract description 3
- -1 lactone compounds Chemical class 0.000 description 32
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 18
- 150000001875 compounds Chemical class 0.000 description 14
- 150000002148 esters Chemical class 0.000 description 10
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 9
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 9
- 238000011156 evaluation Methods 0.000 description 9
- 238000000034 method Methods 0.000 description 7
- 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 6
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 6
- 239000000796 flavoring agent Substances 0.000 description 6
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- 239000000463 material Substances 0.000 description 6
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- 238000005160 1H NMR spectroscopy Methods 0.000 description 4
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- 150000001299 aldehydes Chemical class 0.000 description 4
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- WEEGYLXZBRQIMU-UHFFFAOYSA-N 1,8-cineole Natural products C1CC2CCC1(C)OC2(C)C WEEGYLXZBRQIMU-UHFFFAOYSA-N 0.000 description 3
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- 241000207199 Citrus Species 0.000 description 3
- LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 3
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- WUOACPNHFRMFPN-UHFFFAOYSA-N alpha-terpineol Chemical compound CC1=CCC(C(C)(C)O)CC1 WUOACPNHFRMFPN-UHFFFAOYSA-N 0.000 description 3
- 238000004440 column chromatography Methods 0.000 description 3
- 150000002170 ethers Chemical class 0.000 description 3
- 229930195733 hydrocarbon Natural products 0.000 description 3
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- 239000004615 ingredient Substances 0.000 description 3
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- 150000002596 lactones Chemical class 0.000 description 3
- 239000012279 sodium borohydride Substances 0.000 description 3
- 229910000033 sodium borohydride Inorganic materials 0.000 description 3
- GRWFGVWFFZKLTI-IUCAKERBSA-N (-)-α-pinene Chemical compound CC1=CC[C@@H]2C(C)(C)[C@H]1C2 GRWFGVWFFZKLTI-IUCAKERBSA-N 0.000 description 2
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- LOKPJYNMYCVCRM-UHFFFAOYSA-N 16-Hexadecanolide Chemical compound O=C1CCCCCCCCCCCCCCCO1 LOKPJYNMYCVCRM-UHFFFAOYSA-N 0.000 description 2
- WRMNZCZEMHIOCP-UHFFFAOYSA-N 2-phenylethanol Chemical compound OCCC1=CC=CC=C1 WRMNZCZEMHIOCP-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
- XMIIGOLPHOKFCH-UHFFFAOYSA-N 3-phenylpropionic acid Chemical compound OC(=O)CCC1=CC=CC=C1 XMIIGOLPHOKFCH-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
- INAXVXBDKKUCGI-UHFFFAOYSA-N 4-hydroxy-2,5-dimethylfuran-3-one Chemical compound CC1OC(C)=C(O)C1=O INAXVXBDKKUCGI-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
- GHBSPIPJMLAMEP-UHFFFAOYSA-N 6-pentyloxan-2-one Chemical compound CCCCCC1CCCC(=O)O1 GHBSPIPJMLAMEP-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
- SCCDQYPEOIRVGX-UHFFFAOYSA-N Acetyleugenol Chemical compound COC1=CC(CC=C)=CC=C1OC(C)=O SCCDQYPEOIRVGX-UHFFFAOYSA-N 0.000 description 2
- 239000005711 Benzoic acid Substances 0.000 description 2
- WVDDGKGOMKODPV-UHFFFAOYSA-N Benzyl alcohol Chemical compound OCC1=CC=CC=C1 WVDDGKGOMKODPV-UHFFFAOYSA-N 0.000 description 2
- ZCTQGTTXIYCGGC-UHFFFAOYSA-N Benzyl salicylate Chemical compound OC1=CC=CC=C1C(=O)OCC1=CC=CC=C1 ZCTQGTTXIYCGGC-UHFFFAOYSA-N 0.000 description 2
- DPUOLQHDNGRHBS-UHFFFAOYSA-N Brassidinsaeure Natural products CCCCCCCCC=CCCCCCCCCCCCC(O)=O DPUOLQHDNGRHBS-UHFFFAOYSA-N 0.000 description 2
- FERIUCNNQQJTOY-UHFFFAOYSA-N Butyric acid Chemical compound CCCC(O)=O FERIUCNNQQJTOY-UHFFFAOYSA-N 0.000 description 2
- DZNVIZQPWLDQHI-UHFFFAOYSA-N Citronellyl formate Chemical compound O=COCCC(C)CCC=C(C)C DZNVIZQPWLDQHI-UHFFFAOYSA-N 0.000 description 2
- FKUPPRZPSYCDRS-UHFFFAOYSA-N Cyclopentadecanolide Chemical compound O=C1CCCCCCCCCCCCCCO1 FKUPPRZPSYCDRS-UHFFFAOYSA-N 0.000 description 2
- ZFMSMUAANRJZFM-UHFFFAOYSA-N Estragole Chemical compound COC1=CC=C(CC=C)C=C1 ZFMSMUAANRJZFM-UHFFFAOYSA-N 0.000 description 2
- 235000010254 Jasminum officinale Nutrition 0.000 description 2
- 240000005385 Jasminum sambac Species 0.000 description 2
- 241000220317 Rosa Species 0.000 description 2
- 239000002262 Schiff base Substances 0.000 description 2
- 150000004753 Schiff bases Chemical class 0.000 description 2
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 2
- KGEKLUUHTZCSIP-HOSYDEDBSA-N [(1s,4s,6r)-1,7,7-trimethyl-6-bicyclo[2.2.1]heptanyl] acetate Chemical compound C1C[C@]2(C)[C@H](OC(=O)C)C[C@H]1C2(C)C KGEKLUUHTZCSIP-HOSYDEDBSA-N 0.000 description 2
- DHKHKXVYLBGOIT-UHFFFAOYSA-N acetaldehyde Diethyl Acetal Natural products CCOC(C)OCC DHKHKXVYLBGOIT-UHFFFAOYSA-N 0.000 description 2
- 150000001241 acetals Chemical class 0.000 description 2
- 150000001242 acetic acid derivatives Chemical class 0.000 description 2
- 239000002253 acid Substances 0.000 description 2
- 150000008044 alkali metal hydroxides Chemical class 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
- 239000003125 aqueous solvent Substances 0.000 description 2
- HUMNYLRZRPPJDN-UHFFFAOYSA-N benzaldehyde Chemical compound O=CC1=CC=CC=C1 HUMNYLRZRPPJDN-UHFFFAOYSA-N 0.000 description 2
- 235000010233 benzoic acid Nutrition 0.000 description 2
- QUKGYYKBILRGFE-UHFFFAOYSA-N benzyl acetate Chemical compound CC(=O)OCC1=CC=CC=C1 QUKGYYKBILRGFE-UHFFFAOYSA-N 0.000 description 2
- SESFRYSPDFLNCH-UHFFFAOYSA-N benzyl benzoate Chemical compound C=1C=CC=CC=1C(=O)OCC1=CC=CC=C1 SESFRYSPDFLNCH-UHFFFAOYSA-N 0.000 description 2
- AKGGYBADQZYZPD-UHFFFAOYSA-N benzylacetone Chemical compound CC(=O)CCC1=CC=CC=C1 AKGGYBADQZYZPD-UHFFFAOYSA-N 0.000 description 2
- SIPUZPBQZHNSDW-UHFFFAOYSA-N bis(2-methylpropyl)aluminum Chemical compound CC(C)C[Al]CC(C)C SIPUZPBQZHNSDW-UHFFFAOYSA-N 0.000 description 2
- 150000001656 butanoic acid esters Chemical class 0.000 description 2
- 150000004649 carbonic acid derivatives Chemical class 0.000 description 2
- 150000001735 carboxylic acids Chemical class 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
- 239000007810 chemical reaction solvent Substances 0.000 description 2
- 229930016911 cinnamic acid Natural products 0.000 description 2
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- NEHNMFOYXAPHSD-UHFFFAOYSA-N citronellal Chemical compound O=CCC(C)CCC=C(C)C NEHNMFOYXAPHSD-UHFFFAOYSA-N 0.000 description 2
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- JOZKFWLRHCDGJA-UHFFFAOYSA-N citronellol acetate Chemical compound CC(=O)OCCC(C)CCC=C(C)C JOZKFWLRHCDGJA-UHFFFAOYSA-N 0.000 description 2
- OSOIQJGOYGSIMF-UHFFFAOYSA-N cyclopentadecanone Chemical compound O=C1CCCCCCCCCCCCCC1 OSOIQJGOYGSIMF-UHFFFAOYSA-N 0.000 description 2
- KSMVZQYAVGTKIV-UHFFFAOYSA-N decanal Chemical compound CCCCCCCCCC=O KSMVZQYAVGTKIV-UHFFFAOYSA-N 0.000 description 2
- 239000002781 deodorant agent Substances 0.000 description 2
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- 238000004821 distillation Methods 0.000 description 2
- HFJRKMMYBMWEAD-UHFFFAOYSA-N dodecanal Chemical compound CCCCCCCCCCCC=O HFJRKMMYBMWEAD-UHFFFAOYSA-N 0.000 description 2
- 230000000694 effects Effects 0.000 description 2
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- PZUDDXJZNSJESK-UHFFFAOYSA-N ethyl 2-cyclohexylpropanoate Chemical compound CCOC(=O)C(C)C1CCCCC1 PZUDDXJZNSJESK-UHFFFAOYSA-N 0.000 description 2
- SHZIWNPUGXLXDT-UHFFFAOYSA-N ethyl hexanoate Chemical compound CCCCCC(=O)OCC SHZIWNPUGXLXDT-UHFFFAOYSA-N 0.000 description 2
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- IFYYFLINQYPWGJ-UHFFFAOYSA-N gamma-decalactone Chemical compound CCCCCCC1CCC(=O)O1 IFYYFLINQYPWGJ-UHFFFAOYSA-N 0.000 description 2
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- 238000001308 synthesis method Methods 0.000 description 2
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Abstract
【解決手段】4,7-ジメチル-6-オクテン-3-オールとジプレニルエーテルとを、97.0/3.0〜99.8/0.2の質量比で含有する香料組成物、当該香料組成物を含む家庭用製品及び香粧品、並びに塩化プレニルとジエチルケトンとの付加反応を行った後、還元反応を行う当該香料組成物の製造方法。
【選択図】なし
Description
本発明の香料組成物は、4,7-ジメチル-6-オクテン-3-オールとジプレニルエーテルを特定の比率で含有する。これにより、4,7-ジメチル-6-オクテン-3-オール及びジプレニルエーテル自身が有する香りとは異なり、フレッシュなフローラル香気を維持したまま、良好なフルーティ感を有する香りとなる。更に意外なことに、4,7-ジメチル-6-オクテン-3-オールとジプレニルエーテルそれぞれが有する香り閾値より香りの閾値が下がるため、香りを認識しやすくなる。
ニトリル類としては、ゲラニルニトリル、シトロネリルニトリル、ドデカンニトリル等が挙げられる。
本発明の香料組成物は、様々な形態の芳香性製品に配合又は適用することができる。その利用分野としては、例えば、香粧品、家庭用製品等がある。
4,7-ジメチル-6-オクテン-3-オールとジプレニルエーテルとを、97.0/3.0〜99.8/0.2、好ましくは99.3/0.7〜99.8/0.2の質量比で含有する香料組成物。
4,7-ジメチル-6-オクテン-3-オールとジプレニルエーテルの合計量が、好ましくは0.01〜99質量%、より好ましくは0.1〜15質量%、更に好ましくは0.3〜5質量%である<1>に記載の香料組成物。
好ましくは<1>又は<2>記載の香料組成物を含む家庭用製品。
好ましくは<1>又は<2>記載の香料組成物を含む香粧品。
塩化プレニルとジエチルケトンとの付加反応を行った後、還元反応を行う<1>記載の香料組成物の製造方法。
付加反応に好ましくは塩基、より好ましくはアルカリ金属の水酸化物、更に好ましくは水酸化ナトリウム、水酸化カリウムから選ばれるいずれか1以上を用いる<5>記載の製造方法。
付加反応に用いる反応溶媒が、好ましくは水性の溶媒である<5>又は<6>に記載の製造方法。
付加反応に用いる塩化プレニルとジエチルケトンの比率が、塩化プレニルに対してジエチルケトンが好ましくは1.5〜10当量、更に好ましくは3〜7当量である<5>〜<7>のいずれか1項に記載の製造方法。
還元反応に用いる還元剤が、好ましくは水素化ホウ素ナトリウム、水素化アルミニウムリチウム、水素化ジイソブチルアルミニウムから選ばれるいずれか1以上である<5>〜<8>のいずれか1項に記載の製造方法。
還元反応に用いる還元剤の量が、好ましくは1〜4当量である<5>〜<9>のいずれかに記載の製造方法
4,7-ジメチル-6-オクテン-3-オールとジプレニルエーテルとを、97.0/3.0〜99.8/0.2、好ましくは99.3/0.7〜99.8/0.2の質量比で含有する組成物の香料としての使用方法。
<12>
4,7-ジメチル-6-オクテン-3-オールとジプレニルエーテルの合計量が、好ましくは0.01〜99質量%、より好ましくは0.1〜15質量%、更に好ましくは0.3〜5質量%である<11>に記載の組成物の香料としての使用方法。
製造例1及び2で得られた各化合物の構造を、核磁気共鳴スペクトル(1H-NMR)により同定した。核磁気共鳴スペクトルは、Varian社製の製品名「Mercury 400」装置を用い、400MHzで、テトラメチルシランを内部標準として測定した。
フラスコに、ジエチルケトン226g、50質量%水酸化ナトリウム水溶液125g、ステアリルトリメチルアンモニウムクロライド1.8gを混合し、70℃まで昇温した。塩化プレニル60gの滴下を3.5時間かけて行い、滴下終了後1時間熟成し、冷却を行った。冷却後、水150gを加えて分層し、反応混合物261gを得た(4,7-ジメチル-6-オクテン-3-オン含有率22質量%、59g)。収率72%。
同様にして更に2回反応を行い、反応混合物計685gを得た(4,7-ジメチル-6-オクテン-3-オンとして合計165g)。
得られた反応混合物からジエチルケトンを留去した後、単蒸留を行い(槽内〜170℃/7kPa)、4,7-ジメチル-6-オクテン-3-オンを91質量%含有する留分を168g得た。留分の一部は中圧カラムクロマトグラフィー(展開溶媒=n-ヘキサン:酢酸エチル=100:0〜99:5)を行い、99%純度の4,7-ジメチル-6-オクテン-3-オンを得た。
残りの蒸留留分は、4,7-ジメチル-6-オクテン-3-オールの製造に用いた。
フラスコに、メタノール20mL、イオン交換水4g、50質量%水酸化ナトリウム水溶液0.2g、水素化ホウ素ナトリウム1.5gを加え、氷浴下攪拌した。攪拌溶液の中に4,7-ジメチル-6-オクテン-3-オン蒸留留分(純度90%)20gをゆっくり滴下した。滴下後氷浴を外し室温にて熟成した。1時間後、6N硫酸を加えてpH4以下にし、その後50質量%水酸化ナトリウムでpH6〜7まで中和した。そのまま常圧でメタノールを蒸発させ、分層後上層を乾燥、ろ過後、エバポレーターにより溶媒を留去し、20gの反応混合物を得た。
得られた反応混合物を中圧カラムクロマトグラフィー(展開溶媒=n-ヘキサン:酢酸エチル=97:3)を行い、11gの4,7-ジメチル-6-オクテン-3-オールを得た。収率82%
また、カラムの残りの部分を更に中圧カラムクロマトグラフィー(展開溶媒=n-ヘキサン:酢酸エチル=99:1)を行い、0.4gのジプレニルエーテルを得た。
1H-NMR(CDCl3, 400MHz), δ1.03(3H, t, J=7.2Hz, Me), 1.05(3H, d, J=6.8Hz, Me), 1.60(3H, s, Me), 1.68(3H, s, Me), 2.00-2.10(1H, m), 2.24-2.34(1H, m, Me), 2.44(1H, q, J=0.72Hz, CH2), 2.48-2.60(1H, m, CH), 4.98-5.08(1H, m, c=CH)
1H-NMR(CDCl3, 400MHz), δ1.67(6H, s, Me×2), 1.74(6H, s, Me×2), 3.93-3.94(4H, d, J=6.8MHz, CH2×2), 5.33-5.37(2H, tt, C=CH×2)
4,7-ジメチル-6-オクテン-3-オール及びジプレニルエーテルを用いて、表1に示す香料組成物を調製し、それぞれの香料組成物の香気を評価した。表中の数値は質量部である(以下同じ)。
匂いの閾値計測にあたっては、Haring, H.G. et al., Journal of Agricultural Food Chemistry, VOL. 20, NO.5, 1972, pp.1018-1021に記載の方法により、4,7-ジメチル-6-オクテン-3-オール、ジプレニルエーテルのいずれか一方のみ、及び両化合物の組み合わせについて、各種濃度の流動パラフィン溶液1点と、ブランクとして流動パラフィンのみ3点の計4点を専門パネルに呈示し、ボトル口の匂い評価を行い、その中から1点匂いの付いているサンプルを挙げさせ、正答率をカウントした。その正答率が62.5%を越えた際のサンプル濃度を検知閾値とした。計測は20〜40代までの匂いの専門パネラー男女17名を対象に行った。
4,7-ジメチル-6-オクテン-3-オール単独、4,7-ジメチル-6-オクテン-3-オールにジプレニルエーテルを質量比99.8/0.2になるように添加したもの、4,7-ジメチル-6-オクテン-3-オールにジプレニルエーテルを質量比99.6/0.4になるように添加したもの、ジプレニルエーテル単独、のそれぞれの2.0〜62.5ppmまでの全6種の濃度の流動パラフィン溶液を調製した。それぞれ50mLずつを100mLのメディアバイアル(マルエム社製)に入れた。また、ブランクとして流動パラフィンのみ50mLを100mLのメディアバイアルに入れたサンプルを調製した。
製造例2で得られた4,7-ジメチル-6-オクテン-3-オールとジプレニルエーテルを用いて、表3に示す組成のシトラスフローラルタイプの洗剤、身体洗浄料用の香料組成物を調製した。
(評価基準)
5:非常に強い
4:強い
3:ふつうに感じられる
2:弱い
1:非常に弱い
Claims (4)
- 4,7-ジメチル-6-オクテン-3-オールとジプレニルエーテルとを、97.0/3.0〜99.8/0.2の質量比で含有する香料組成物。
- 請求項1記載の香料組成物を含む家庭用製品。
- 請求項1記載の香料組成物を含む香粧品。
- 塩化プレニルとジエチルケトンとの付加反応を行った後、還元反応を行う請求項1記載の香料組成物の製造方法。
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CN112321403A (zh) * | 2020-12-02 | 2021-02-05 | 天津市安凯特科技发展有限公司 | 一种二甲基辛烯酮的合成方法 |
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JP7028552B2 (ja) | 2016-11-24 | 2022-03-02 | 花王株式会社 | 温熱具 |
CN112321403A (zh) * | 2020-12-02 | 2021-02-05 | 天津市安凯特科技发展有限公司 | 一种二甲基辛烯酮的合成方法 |
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