JP2017534650A - 有機化合物におけるまたは関連する改善 - Google Patents
有機化合物におけるまたは関連する改善 Download PDFInfo
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- JP2017534650A JP2017534650A JP2017525074A JP2017525074A JP2017534650A JP 2017534650 A JP2017534650 A JP 2017534650A JP 2017525074 A JP2017525074 A JP 2017525074A JP 2017525074 A JP2017525074 A JP 2017525074A JP 2017534650 A JP2017534650 A JP 2017534650A
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- perfume
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- 150000002894 organic compounds Chemical class 0.000 title 1
- 150000001875 compounds Chemical class 0.000 claims abstract description 89
- 239000002304 perfume Substances 0.000 claims abstract description 79
- 239000004615 ingredient Substances 0.000 claims abstract description 47
- 239000000203 mixture Substances 0.000 claims description 89
- 239000003205 fragrance Substances 0.000 claims description 44
- NBBJYMSMWIIQGU-UHFFFAOYSA-N Propionic aldehyde Chemical class CCC=O NBBJYMSMWIIQGU-UHFFFAOYSA-N 0.000 claims description 40
- SDQFDHOLCGWZPU-UHFFFAOYSA-N lilial Chemical compound O=CC(C)CC1=CC=C(C(C)(C)C)C=C1 SDQFDHOLCGWZPU-UHFFFAOYSA-N 0.000 claims description 23
- 241000234269 Liliales Species 0.000 claims description 21
- 150000001299 aldehydes Chemical group 0.000 claims description 19
- 125000003118 aryl group Chemical group 0.000 claims description 11
- 238000000034 method Methods 0.000 claims description 11
- 125000001424 substituent group Chemical group 0.000 claims description 11
- 239000003599 detergent Substances 0.000 claims description 10
- 239000004753 textile Substances 0.000 claims description 9
- 108090000790 Enzymes Proteins 0.000 claims description 8
- 102000004190 Enzymes Human genes 0.000 claims description 8
- 150000001558 benzoic acid derivatives Chemical class 0.000 claims description 7
- 241000700159 Rattus Species 0.000 claims description 6
- KPPVNWGJXFMGAM-UUILKARUSA-N (e)-2-methyl-1-(6-methyl-3,4-dihydro-2h-quinolin-1-yl)but-2-en-1-one Chemical compound CC1=CC=C2N(C(=O)C(/C)=C/C)CCCC2=C1 KPPVNWGJXFMGAM-UUILKARUSA-N 0.000 claims description 5
- 230000015556 catabolic process Effects 0.000 claims description 5
- 238000006731 degradation reaction Methods 0.000 claims description 5
- LOTBYPQQWICYBB-UHFFFAOYSA-N methyl n-hexyl-n-[2-(hexylamino)ethyl]carbamate Chemical compound CCCCCCNCCN(C(=O)OC)CCCCCC LOTBYPQQWICYBB-UHFFFAOYSA-N 0.000 claims description 5
- UKZXPOJABTXLMK-UHFFFAOYSA-N 3-[2-methyl-4-(2-methylpropyl)phenyl]propanal Chemical compound CC(C)CC1=CC=C(CCC=O)C(C)=C1 UKZXPOJABTXLMK-UHFFFAOYSA-N 0.000 claims description 2
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- 101100439662 Arabidopsis thaliana CHR5 gene Proteins 0.000 abstract 1
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- 235000019645 odor Nutrition 0.000 description 38
- 125000005394 methallyl group Chemical group 0.000 description 28
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 27
- 239000002253 acid Substances 0.000 description 21
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 18
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- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 12
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- 238000004140 cleaning Methods 0.000 description 11
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- 125000000217 alkyl group Chemical group 0.000 description 10
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- 229910004298 SiO 2 Inorganic materials 0.000 description 7
- 239000002386 air freshener Substances 0.000 description 7
- 229920001577 copolymer Polymers 0.000 description 7
- 239000002537 cosmetic Substances 0.000 description 7
- 229940088598 enzyme Drugs 0.000 description 7
- 239000002904 solvent Substances 0.000 description 7
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 6
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical class OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 6
- 239000012190 activator Substances 0.000 description 6
- 239000000194 fatty acid Substances 0.000 description 6
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- ZCTQGTTXIYCGGC-UHFFFAOYSA-N Benzyl salicylate Chemical compound OC1=CC=CC=C1C(=O)OCC1=CC=CC=C1 ZCTQGTTXIYCGGC-UHFFFAOYSA-N 0.000 description 5
- IMROMDMJAWUWLK-UHFFFAOYSA-N Ethenol Chemical compound OC=C IMROMDMJAWUWLK-UHFFFAOYSA-N 0.000 description 5
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- 229930195729 fatty acid Natural products 0.000 description 5
- 238000009472 formulation Methods 0.000 description 5
- 239000000499 gel Substances 0.000 description 5
- 229910052742 iron Inorganic materials 0.000 description 5
- 239000010410 layer Substances 0.000 description 5
- 150000003856 quaternary ammonium compounds Chemical class 0.000 description 5
- 229910052707 ruthenium Inorganic materials 0.000 description 5
- HPALAKNZSZLMCH-UHFFFAOYSA-M sodium;chloride;hydrate Chemical compound O.[Na+].[Cl-] HPALAKNZSZLMCH-UHFFFAOYSA-M 0.000 description 5
- 239000002689 soil Substances 0.000 description 5
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- KHWTYGFHPHRQMP-UHFFFAOYSA-N (4-propan-2-ylcyclohexyl)methanol Chemical compound CC(C)C1CCC(CO)CC1 KHWTYGFHPHRQMP-UHFFFAOYSA-N 0.000 description 4
- NEHPIUGJDUWSRR-UHFFFAOYSA-N 1-(4-propan-2-ylcyclohexyl)ethanol Chemical compound CC(C)C1CCC(C(C)O)CC1 NEHPIUGJDUWSRR-UHFFFAOYSA-N 0.000 description 4
- HZAXFHJVJLSVMW-UHFFFAOYSA-N 2-Aminoethan-1-ol Chemical compound NCCO HZAXFHJVJLSVMW-UHFFFAOYSA-N 0.000 description 4
- OHRBQTOZYGEWCJ-UHFFFAOYSA-N 3-(3-propan-2-ylphenyl)butanal Chemical compound CC(C)C1=CC=CC(C(C)CC=O)=C1 OHRBQTOZYGEWCJ-UHFFFAOYSA-N 0.000 description 4
- IKHGUXGNUITLKF-UHFFFAOYSA-N Acetaldehyde Chemical compound CC=O IKHGUXGNUITLKF-UHFFFAOYSA-N 0.000 description 4
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 4
- ZTQSAGDEMFDKMZ-UHFFFAOYSA-N Butyraldehyde Chemical compound CCCC=O ZTQSAGDEMFDKMZ-UHFFFAOYSA-N 0.000 description 4
- CERQOIWHTDAKMF-UHFFFAOYSA-N Methacrylic acid Chemical compound CC(=C)C(O)=O CERQOIWHTDAKMF-UHFFFAOYSA-N 0.000 description 4
- 229920002472 Starch Polymers 0.000 description 4
- IKHGUXGNUITLKF-XPULMUKRSA-N acetaldehyde Chemical compound [14CH]([14CH3])=O IKHGUXGNUITLKF-XPULMUKRSA-N 0.000 description 4
- 230000002378 acidificating effect Effects 0.000 description 4
- 150000001298 alcohols Chemical class 0.000 description 4
- 229910052910 alkali metal silicate Inorganic materials 0.000 description 4
- 125000003342 alkenyl group Chemical group 0.000 description 4
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- 229910017052 cobalt Inorganic materials 0.000 description 4
- 239000010941 cobalt Substances 0.000 description 4
- GUTLYIVDDKVIGB-UHFFFAOYSA-N cobalt atom Chemical compound [Co] GUTLYIVDDKVIGB-UHFFFAOYSA-N 0.000 description 4
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- 239000000975 dye Substances 0.000 description 4
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- 229910052723 transition metal Inorganic materials 0.000 description 4
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- ZFNVDHOSLNRHNN-UHFFFAOYSA-N xi-3-(4-Isopropylphenyl)-2-methylpropanal Chemical compound O=CC(C)CC1=CC=C(C(C)C)C=C1 ZFNVDHOSLNRHNN-UHFFFAOYSA-N 0.000 description 4
- KHQDWCKZXLWDNM-KPKJPENVSA-N (e)-2-ethyl-4-(2,2,3-trimethylcyclopent-3-en-1-yl)but-2-en-1-ol Chemical compound CC\C(CO)=C/CC1CC=C(C)C1(C)C KHQDWCKZXLWDNM-KPKJPENVSA-N 0.000 description 3
- SMZOUWXMTYCWNB-UHFFFAOYSA-N 2-(2-methoxy-5-methylphenyl)ethanamine Chemical compound COC1=CC=C(C)C=C1CCN SMZOUWXMTYCWNB-UHFFFAOYSA-N 0.000 description 3
- NIXOWILDQLNWCW-UHFFFAOYSA-N 2-Propenoic acid Natural products OC(=O)C=C NIXOWILDQLNWCW-UHFFFAOYSA-N 0.000 description 3
- YLIXVKUWWOQREC-UHFFFAOYSA-N 2-methyl-3-[4-(2-methylpropyl)phenyl]propanal Chemical compound CC(C)CC1=CC=C(CC(C)C=O)C=C1 YLIXVKUWWOQREC-UHFFFAOYSA-N 0.000 description 3
- ZDFKSZDMHJHQHS-UHFFFAOYSA-N 2-tert-butylbenzoic acid Chemical compound CC(C)(C)C1=CC=CC=C1C(O)=O ZDFKSZDMHJHQHS-UHFFFAOYSA-N 0.000 description 3
- JFTSYAALCNQOKO-UHFFFAOYSA-N 3-(4-ethylphenyl)-2,2-dimethylpropanal Chemical compound CCC1=CC=C(CC(C)(C)C=O)C=C1 JFTSYAALCNQOKO-UHFFFAOYSA-N 0.000 description 3
- YPZUZOLGGMJZJO-UHFFFAOYSA-N Ambronide Chemical compound C1CC2C(C)(C)CCCC2(C)C2C1(C)OCC2 YPZUZOLGGMJZJO-UHFFFAOYSA-N 0.000 description 3
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical group C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 3
- 241000282472 Canis lupus familiaris Species 0.000 description 3
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Classifications
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C47/00—Compounds having —CHO groups
- C07C47/20—Unsaturated compounds having —CHO groups bound to acyclic carbon atoms
- C07C47/235—Unsaturated compounds having —CHO groups bound to acyclic carbon atoms containing six-membered aromatic rings and other rings
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C47/00—Compounds having —CHO groups
- C07C47/20—Unsaturated compounds having —CHO groups bound to acyclic carbon atoms
- C07C47/235—Unsaturated compounds having —CHO groups bound to acyclic carbon atoms containing six-membered aromatic rings and other rings
- C07C47/238—Unsaturated compounds having —CHO groups bound to acyclic carbon atoms containing six-membered aromatic rings and other rings having unsaturation outside the aromatic rings
-
- C—CHEMISTRY; METALLURGY
- C11—ANIMAL OR VEGETABLE OILS, FATS, FATTY SUBSTANCES OR WAXES; FATTY ACIDS THEREFROM; DETERGENTS; CANDLES
- C11B—PRODUCING, e.g. BY PRESSING RAW MATERIALS OR BY EXTRACTION FROM WASTE MATERIALS, REFINING OR PRESERVING FATS, FATTY SUBSTANCES, e.g. LANOLIN, FATTY OILS OR WAXES; ESSENTIAL OILS; PERFUMES
- C11B9/00—Essential oils; Perfumes
- C11B9/0061—Essential oils; Perfumes compounds containing a six-membered aromatic ring not condensed with another ring
-
- C—CHEMISTRY; METALLURGY
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Abstract
Description
同じく、WO2009027957は、香料パレットからの、既知の香料成分の組み合わせの調合物に帰する解決策を提案する。
R2はHまたはMeであり;および
R3は、C3〜C6分岐、直鎖または環状アルケニル残基である;
により表される化合物を提供する。
本発明の特定の側面において、式I(式中、R1およびR2は上記で定義されるとおりであり、R3は、アリル、2−メチルアリル、2−メチレンブチル、3−メチルブタ−2−エン−1−イル、3−メチルブタ−3−エン−2−イルおよびブタ−2−エン−1−イルからなる群から選択される)により表される化合物を提供する。
本発明のさらなる側面において、式Iにより表される化合物の炭素原子の合計数は、16を超えない。
さらに、本発明の化合物は、特に、実質的で、長続きする匂い特性を生成することができ、それらは、特に、実質的で、長続きするミュゲの匂い特性に寄与することができる。
本発明の化合物は、特に影響力の強い香料成分であり得る。香料成分が及ぼす影響はその匂い値に関与する。匂い値は検出閾値濃度に対する蒸気圧の比率である。
本発明のいくつかの化合物の高い匂い値は、持続可能性についての需要が存在し、影響力の強い香料成分の提供により、パーフューマーが、より低い濃度の物質で望ましいフレグランスを作り出すことを可能にする点で、顕著である。
tert-ブチル安息香酸は、雄性ラットにおいて精巣に影響を引き起すことが知られている(Hunter et al. Food Cosmet. Toxicol. 1965, 3: 289-298; Cagen et al. J. Am. Coll. Toxicol. 1989, 8 (5): 1027-1038)。
芳香族環が、プロパナール側鎖に対するp−位において代謝的に不活性なt−ブチル基で置換されている、Lilialとは対照的に、本発明の化合物は、直鎖または分岐のアルケニル置換基(一般式IのR3)を保持する。このアルケニル置換基は、続くビシナルジオールへの加水分解を伴うヒドロキシル化またはエポキシ化などの脊椎動物におけるさらなる酸化的代謝分解をうけやすい。得られる代謝物は、したがって、p−t−ブチル安息香酸と比較して、異なる物理的性質、例えばより高い水溶性を有し、ならびにしたがって、雄性ラットおよびイヌに対してp−t−ブチル安息香酸の生殖毒性の影響を及ぼさないことが予測される。あるいは、アルケニル置換基は、例えば、アルケニル置換基に作用する記載された代謝ステップがプロパナール側鎖の酸化的分解よりも速く生じる場合に、置換された安息香酸に対するプロパナール側鎖の分解を予防または低減し得る。
本発明は、その別の側面において、アルデヒド官能基を有する置換基に対してアリール環上のオルト位が非置換である、および/またはパラ位においてアルケニル置換基を有する、アリール置換プロパナール着臭剤、特にLilial(商標)の代替としての、香料組成物における上記に定義される化合物の使用を提供する。
本発明のさらに別の側面において、上記で定義された化合物を含む香料組成物を提供する。
本発明のさらに別の側面において、アルデヒド官能基を有する置換基に対してアリール環上のオルト位が非置換である、任意のアリール置換プロパナール着臭剤、特にLilial(商標)を減少した量で有する、または実質的に含まない、上記で定義された化合物を含む香料組成物を提供する。
本発明の化合物は、パーフューマーが達成しようとする特定の嗅覚的効果に応じて任意の量で香料組成物中に存在してもよい。本発明の特定の態様においては、本発明の香料組成物は、前記組成物の0.1〜100重量%の量で上記に定義される化合物を含有してもよい。
好ましくは、香料組成物に採用されてもよい少なくとも一種の追加の香料成分は、3−(4−イソブチル−2−メチルフェニル)プロパナールのような、ミュゲの匂い特性を保有する。
R2はHまたはMeであり;および
R3は、C3〜C6分岐、直鎖または環状アルケニル残基である;
により表される化合物との反応生成物であることが好ましい。
かかる反応により、様々な生成物、例えば対応するイミン、エナミン、ヘミ−アミナールまたはアミナールが得られ得る。
式I
R2はHまたはMeであり;および
R3は、C3〜C6分岐、直鎖または環状アルケニル残基である;
により表される化合物により香りづけられる、ファインフレグランスまたはパーソナルケアもしくは家庭用ケア組成物などの消費者製品を提供する。
便器洗浄剤または化粧室洗浄剤、すなわち水洗便器および男性用小便器を洗浄するための製品であり、これらの製品は好ましくは、粉末、ブロック、錠剤または液体、好ましくはゲルの形態で供給される。界面活性剤などの他の典型的な成分に加えて、これらは一般に、有機酸(例えば、クエン酸および/または乳酸)あるいは、水あかもしくは尿スケール(urine scale)を除去するための硫酸水素ナトリウム、アミド硫酸またはリン酸を含む;
特殊目的のための洗浄製品、例は、ガラスセラミック製のホブ用のもの、ならびにまたカーペット洗浄剤およびシミ抜き剤である。
塗料保存剤、塗料艶出し剤、塗料洗浄剤、洗浄保存剤、洗車用シャンプー、自動車洗浄およびワックス製品、トリム金属用艶出し剤、トリム金属用保護フィルム、プラスチック洗浄剤、タール除去剤、スクリーン洗浄剤、エンジン洗浄剤など。
(a)化粧用スキンケア製品、特に風呂用製品、肌洗浄およびクレンジング製品、スキンケア製品、アイメイク、リップケア製品、ネイルケア製品、デリケートゾーンケア製品、フットケア製品;
(b)特定の効果を有する化粧品、特に日焼け止め剤、日焼け製品、脱色素製品、デオドラント、制汗剤、脱毛剤、シェービング製品、香水;
(c)化粧用デンタルケア製品、特にデンタルおよびオーラルケア製品、トゥースケア製品、義歯用洗浄剤、義歯用接着剤;ならびに
(d)化粧用ヘアケア製品、特にヘアシャンプー、ヘアケア製品、ヘアセッティング製品、整髪製品およびヘアカラー製品。
例えば液体もしくは固体形態いずれかの、洗剤または繊維用仕上げ剤。
エアフレッシュナーおよび部屋用芳香剤は以下を含む:
好ましくは揮発性で通常心地よい香りの化合物を含有し、有利には非常に少量であっても、不快な臭いをマスクすることができる製品。居住エリアのエアフレッシュナーは、特に、天然および合成の精油、例えば松葉油、柑橘油、ユーカリ油、ラベンダー油などを、例えば50重量%までの量で含有する。エアロゾルとしては、それらは、かかる精油より少量の、一例として5重量%未満または2重量%未満を含有する傾向があるが、さらに、例えばアセトアルデヒド(特に、<0.5重量%)、イソプロピルアルコール(特に、<5重量%)、鉱油(特に、<5重量%)、および噴射剤などの化合物を含む。その他の提供形態としては、スティックおよびブロックが含まれる。それらは典型的には、精油を含むゲル濃縮物を用いて生産される。ホルムアルデヒド(保存用)およびクロロフィル(好ましくは<5重量%)、およびさらなる成分を添加することも可能である。しかし、エアフレッシュナーは居住空間に限定されず、自動車、食器棚、食器洗浄機、冷蔵庫または靴用に意図されてもよく、掃除機での使用も可能である。家庭においては(例えば食器棚において)、例えば、臭気改良剤に加えて殺菌剤も使用され、これらは、好ましくはリン酸カルシウム、タルク、ステアリン、および精油などの化合物を含有し、これらの製品は例えば小袋の形態をとる。
ビルダー物質、界面活性剤、酵素、好ましくは有機および/または無機の過酸素化合物、過酸素活性剤などの漂白剤、水混和性有機溶媒、金属イオン封鎖剤、電解質、pH調整剤、増粘剤、ならびに汚れ放出(soil release)活性物質、光学的増白剤、灰色化阻害剤、色移り防止剤、発泡調節剤、および染料などのさらなる補助剤。
界面活性剤は、本発明の消費者製品中に5重量%〜50重量%の量で使用することができる。
水溶性無機ビルダー材料には、アルカリケイ酸塩およびポリリン酸塩、例えば三リン酸ナトリウムが含まれる。結晶性または非晶質アルカリアルミノシリケート、例えば結晶性アルミノケイ酸ナトリウムもまた、水不溶性、水分散性無機ビルダー材料として、例えば50重量%までの量で、用いることができる。アルミノシリケートは典型的には、30μm未満の粒径を有する粒子を含む。
ビルダー物質は、本発明の消費者製品組成物に、60重量%までのレベルで含有させてもよい。
本発明をさらに例証するために役立つ一連の例が以下に続く。
A)2−メチル−4−(2−メチルアリル)フェノール
o−クレゾール(54.1g、0.5mol)を水に懸濁し、KOH(36.5g、0.65mol、1.3等量)を激しい撹拌下で添加した。温度を45℃まで上昇させ、灰黄色溶液を形成し、それをさらに20分間撹拌し、その後10℃まで冷却した。この温度において、3−クロロ−2−メチルプロパ−1−エン(58.9g、0.65mol、1.3等量)を15分間にわたり液滴添加した。得られた混合物を6日間激しく撹拌し、その後トルエン(300ml)で希釈した。有機層を2N NaOH水溶液(各500ml)で3回抽出した。合わされたアルカリ水層にトルエン(300ml)を添加し、氷浴冷却下で濃HCl水溶液(350ml)を添加した。層を分離させ、水層をトルエンでさらに抽出した。合わされた有機層をブラインで洗浄して中性にし、その後MgSO4上で乾燥し、濃縮した。残留物を0.06mbar/76〜83℃において、Vigreuxカラム上で蒸留させ、無色オイルとして2−メチル−4−(2−メチルアリル)フェノール(36.2g、45%、純度92%、残余物はo−アルキル化生成物であった)を単離した。
2−メチル−4−(2−メチルアリル)フェノール(5.0g、30.8mmol)をジクロロメタン(60ml)に溶解し、ピリジン(4.63g、58.6mmol、1.9等量)を添加し、溶液を0℃まで冷却した。その後トリフルオロメタンスルホン酸無水物(ジクロロメタン中1M、32.4ml、32.4mmol、1.05等量)を、滴下漏斗を介して添加し、得られた溶液を3時間撹拌した。その後2N HCl水溶液(10ml)を液滴添加した。水層を分離し、有機層を希NaHCO3水溶液およびブラインで洗浄し、その後MgSO4上で乾燥させ、i.RVで濃縮し、淡黄色オイルとして2−メチル−4−(2−メチルアリル)フェニルトリフルオロメタンスルホナート(8.9g、98%)を得た。続くヘックカップリング反応のために、この生成物(30.2mmol)をジメチルホルムアミド(50ml)に溶解し、エチルアクリラート(5.75g、57.5mmol、1.9等量)に続いてトリエチルアミン(15.0g、148mmol、4.9等量)を添加した。得られた溶液をアルゴンで10分間パージし、その後、ビス(トリフェニルホスフィン)パラジウム(II)ジクロリド(1.06g、1.51mmol、5mol%)を添加し、混合物をアルゴン雰囲気下で80℃において6日間撹拌した。混合物をMTBEで希釈し、水およびブラインで洗浄し、その後MgSO4上で乾燥させ、i.RVで濃縮した。残留物をSiO2上でのFC(ヘキサン/酢酸エチル 19:1で溶出)により精製し、無色オイルとして(E)−エチル3−(2−メチル−4−(2−メチルアリル)フェニル)アクリラート(Rf=0.21、3.9g、53%)を得た。
エチル3−(2−メチル−4−(2−メチルアリル)フェニル)アクリラート(2.0g、8.2mmol)を10℃において、Et2O(40ml)中LiAlH4(0.47g、12.2mmol、1.5等量)の懸濁液に液滴添加した。得られた混合物を、アルゴン雰囲気下で室温において、18時間撹拌した。その後、水(0.47g)を10℃において注意深く添加し、続いて15%NaOH水溶液(0.47ml)を、そして最後に再び水(0.9ml)を添加した。形成した懸濁液を1時間撹拌後、沈殿物を濾別し、濾液を濃縮して無色オイルを得た(1.7g)。このオイル(8.3mmol)をジクロロメタン(5ml)に溶解し、溶液を、ジクロロメタン(25ml)中デス−マーチンペルヨージナン(4.24g、10mmol、1.2等量)の溶液に添加した。混合物を2時間撹拌し、その後MTBEで希釈し、希NaHCO3水溶液、水、およびブラインで洗浄した。MgSO4上で乾燥および濃縮後に得られた残留物をSiO2上でのFC(ヘキサン/酢酸エチル 19:1で溶出)により精製し、無色オイルとして表題化合物を得た(Rf=0.14、0.60g、36%)。
Claims (12)
- 式I
R2はHまたはMeであり;および
R3は、C3〜C6分岐、直鎖または環状アルケニル残基である;
により表される化合物。 - 式I
R2はHまたはMeであり;および
R3は、C3〜C6分岐、直鎖または環状アルケニル残基である;
により表される化合物を放出するのに好適なプロ香料であって、
好ましくは、式Iにより表される化合物のアミナールおよび/またはエナミンである、前記プロ香料。 - 香料成分としての、式Iの化合物および/または請求項2に記載のプロ香料の使用。
- 香料成分が、グリーンの匂い特性を有する、請求項3に記載の化合物および/またはプロ香料の使用。
- 式Iの化合物および/または請求項2に記載のプロ香料を含む香料組成物。
- アルデヒド官能基を有する置換基に対してアリール環上のオルト位が非置換である任意のアリール置換プロパナール着臭剤、特にLilial(商標)を実質的に含まない、請求項5に記載の香料組成物。
- 1種以上の追加のフレグランス成分、特に3−(4−イソブチル−2−メチルフェニル)プロパナールを含む、請求項5または6に記載の香料組成物。
- 少なくとも1種の、請求項1に記載の化合物、請求項2に記載のプロ香料、または請求項5〜7のいずれか一項に記載の香料組成物を含む、パーソナルケアまたは家庭用ケア組成物。
- さらに酵素を含む、請求項8に記載のパーソナルケアまたは家庭用ケア組成物。
- テキスタイル処理製品であることを特徴とする、請求項8または9に記載のパーソナルケアまたは家庭用ケア組成物。
- 洗剤組成物であることを特徴とする、請求項8〜10のいずれか一項に記載のパーソナルケアまたは家庭用ケア組成物。
- グリーンの匂い特性をファインフレグランスまたは消費者製品に付与する方法であって、それに請求項1に記載の化合物および/または請求項2に記載のプロ香料をそれに添加するステップ、およびアルデヒド官能基を含有する置換基に対して環上のオルト位が非置換である、任意のアリール置換アルカナール化合物を前記ファインフレグランスまたは消費者製品から選択的に排除するステップを含み、前記選択的添加または排除は、ラットから単離された肝細胞とインキュベートした場合に、その安息香酸誘導体への酵素的に媒介される分解に対する前記化合物の感受性に基づいており、前記化合物は、それらがその安息香酸誘導体に分解しないことを基準として添加に好適である一方で、前記化合物は、それらがその安息香酸誘導体に分解することを基準として排除される、前記方法。
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EP3218342A1 (en) | 2017-09-20 |
CN107074714A (zh) | 2017-08-18 |
US20170297993A1 (en) | 2017-10-19 |
EP3218342B1 (en) | 2019-03-27 |
JP6491748B2 (ja) | 2019-03-27 |
WO2016074698A1 (en) | 2016-05-19 |
CN107074714B (zh) | 2020-11-06 |
MX2017005862A (es) | 2017-06-26 |
BR112017008533B1 (pt) | 2021-11-23 |
SG11201703026WA (en) | 2017-05-30 |
US10138195B2 (en) | 2018-11-27 |
BR112017008533A2 (pt) | 2017-12-19 |
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