CN111936608A - 麝香味组合物 - Google Patents
麝香味组合物 Download PDFInfo
- Publication number
- CN111936608A CN111936608A CN201980023585.XA CN201980023585A CN111936608A CN 111936608 A CN111936608 A CN 111936608A CN 201980023585 A CN201980023585 A CN 201980023585A CN 111936608 A CN111936608 A CN 111936608A
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- 241000402754 Erythranthe moschata Species 0.000 title claims abstract description 35
- 150000001875 compounds Chemical class 0.000 claims abstract description 97
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- 239000003205 fragrance Substances 0.000 claims description 65
- 239000003795 chemical substances by application Substances 0.000 claims description 18
- 238000000034 method Methods 0.000 claims description 18
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- 239000002537 cosmetic Substances 0.000 claims description 10
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- 230000001965 increasing effect Effects 0.000 claims description 9
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- 150000002170 ethers Chemical class 0.000 claims description 5
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- 150000002576 ketones Chemical class 0.000 claims description 5
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- 239000002262 Schiff base Substances 0.000 claims description 4
- 150000004753 Schiff bases Chemical class 0.000 claims description 4
- 150000001241 acetals Chemical class 0.000 claims description 4
- 230000002708 enhancing effect Effects 0.000 claims description 4
- 150000002825 nitriles Chemical class 0.000 claims description 4
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- 238000002156 mixing Methods 0.000 abstract description 19
- 230000000694 effects Effects 0.000 abstract description 14
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- 238000006467 substitution reaction Methods 0.000 description 4
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- JIYIHILAGIZIMD-CLFYSBASSA-N (4z)-cyclopentadec-4-en-1-one Chemical compound O=C1CCCCCCCCCC\C=C/CC1 JIYIHILAGIZIMD-CLFYSBASSA-N 0.000 description 3
- WSTQLNQRVZNEDV-CSKARUKUSA-N (e)-4-methyldec-3-en-5-ol Chemical compound CCCCCC(O)C(\C)=C\CC WSTQLNQRVZNEDV-CSKARUKUSA-N 0.000 description 3
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- GQBVHGLNSHPKPG-UHFFFAOYSA-N 1-(2-tert-butylcyclohexyl)oxybutan-2-ol Chemical compound CCC(O)COC1CCCCC1C(C)(C)C GQBVHGLNSHPKPG-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
- 239000005711 Benzoic acid Substances 0.000 description 3
- 241001465754 Metazoa Species 0.000 description 3
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- 239000004902 Softening Agent Substances 0.000 description 3
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- 229940088601 alpha-terpineol Drugs 0.000 description 3
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Abstract
本发明提供一种与其它各种香料的调和性优异,并且通过调配而能够创造出特征性香味的效果的麝香味组合物。所述组合物是含有通式(I)所表示的化合物的组合物,所述通式(I)所表示的化合物的E型与通式(I)的Z型的比率为E型/Z型=3/7以上7/3以下。
Description
技术领域
本发明涉及一种麝香味组合物。
背景技术
香味是对产品等产生嗜好性或高级感、安心感、对其效果的期待感等的重要的因素。进一步,有特征的香味赋予识别产品的效果以及吸引顾客的吸引力。特别是麝香的香调被用于以肥皂或化妆品为首的各种调和香料中。
已知氧代环十七碳-10-烯-2-酮或氧代环十七碳-8-烯-2-酮等是赋予麝香的香调的香料原材料。
专利文献1公开了E型:Z型的比率为85:15的氧代环十七碳-10-烯-2-酮(异黄葵内酯(isoambrettolide))的制造。
此外,专利文献2公开了Z型的含有率为99.5%以上的氧代环十七碳-10-烯-2-酮的制造。
此外,专利文献3公开了氧代环十七碳-10-烯-2-酮的制造。
此外,氧代环十七碳-8-烯-2-酮的Z型以CAS编号123-69-3注册。已知该氧代环十七碳-8-烯-2-酮的Z型是在植物性天然香料“麝香梨子油(Ambrette seed oil)”中存在10%左右的天然物。
现有技术文献
专利文献
专利文献1:日本特表2017-517477号公报
专利文献2:日本特开平11-293284号公报
专利文献3:日本特开2016-124868号公报
专利文献4:WO2016/5361号公报
发明内容
本发明所要解决的技术问题
麝香是被广泛使用的重要的香料原材料,但由于是动物性香料,所以动物气息感也较强。特别是盥洗产品等优选具有清洁感的清新的香调。因此,为了提高调香的自由度,希望有降低动物气息感,易于在调和香料中与其它香调调和,并且具有没有缺点的麝香香调的香料组合物。
因此,本发明的目的在于提供一种与其它各种香料的调和性优异,并且通过调配而能够创造出特征性香味的效果的麝香味组合物。
解决技术问题的手段
本发明是含有下述通式(I)所表示的化合物的组合物,其中,所述通式(I)所表示的化合物的E型与所述通式(I)所表示的化合物的Z型的比率为E型/Z型=3/7以上7/3以下。
发明的效果
本发明的组合物具有与其它各种香料的调和性优异,并且通过调配而能够创造出特征性香味的效果的优点。
具体实施方式
在本发明中,通式(I)所表示的化合物从与其它各种香料的调和性优异,并且通过调配而创造出特征性香味的效果的观点出发,E型与Z型的比率为E型/Z型=3/7以上7/3以下、优选为4/6以上7/3以下、更优选为5/5以上7/3以下、进一步优选大于5/5以上且为7/3以下。
含有通式(I)所表示的化合物的本发明的组合物可以通过例如以E型和Z型的比率成为E型/Z型=3/7以上7/3以下的方式,将通式(I)所表示的化合物(以下有时称为“式(I)的化合物”或“化合物(I)”)的E型和Z型混合而获得。
式(I)的化合物的E型可以通过现有公知的方法获得。作为这样的方法,例如,可以举出Facile synthesis of(E)-7-hexadecen-1,16-olide,J.In.Chem.Soc.Vol.83,1179-1180,2006中记载的方法。
式(I)的化合物的Z型,例如可以通过使用了Z选择性催化剂的置换反应(Metathesis reaction)将9-癸烯基-7-辛烯酸酯环化而获得(Highly Active RutheniumMetathesis Catalysts Exhibiting Unprecedented Activity and Z-Selectivity,J.Am.Chem.Soc.135,1276-1279,2013)。
本发明的组合物优选含有通式(I)所表示的化合物以外的香料。在本发明中,从与其它各种香料的调和性优异,并且通过调配而能够创造出特征性香味的效果的观点出发,通式(I)所表示的化合物的含量在组合物中,优选为0.01质量%以上、更优选为0.1质量%以上、更优选为0.3质量%以上、更优选为1质量%以上,而且,优选为99质量%以下、更优选为50质量%以下、进一步优选为25质量%以下。
本发明的组合物含有通式(I)所表示的化合物,通式(I)所表示的化合物的E型与通式(I)所表示的化合物的Z型的比率为E型/Z型=3/7以上7/3以下,因此,与其它各种香料的调和性优异,并且通过调配而能够创造出特征性香味的效果。此外,本发明的组合物可以含有通常使用的其它香料成分或所希望组成的调和香料作为化合物(I)以外的香料。通过含有化合物(I)以外的香料,可以对本发明的组合物赋予例如花香调、花束调、风信子调、天竺葵调、玫瑰调、佛手柑调、兰花调、铃兰调(铃兰)的香气。即,本发明的组合物优选进一步含有通式(I)的化合物以外的香料。
在本发明的组合物中,作为可以与化合物(I)组合使用的其它香料,可以举出醇类、烃类、酚类、酯类、碳酸酯类、醛类、酮类、缩醛类、醚类、羧酸、除化合物(I)以外的内酯类、腈类、席夫碱类、天然精油或天然提取物等的香料成分。
其中,优选为醇类、酯类、醛类、酮类、醚类、碳酸酯类、内酯类、天然精油或天然提取物。
在本说明书中,各香料的“类”是指单一的化合物或2种以上的化合物的混合物。
作为醇类,可以举出脂肪族醇、萜烯类醇、芳香族醇、其它醇等。其中,优选为脂肪族醇。
作为萜烯类醇,可以举出芳樟醇、香茅醇、香叶醇、橙花醇、萜品醇、α-萜品醇、二氢月桂烯醇、法呢醇、橙花叔醇、雪松醇、薄荷醇、冰片、α-松油醇(p-薄荷-1-烯-8-醇(p-menth-1-en-8-ol))等。
作为芳香族醇,可以举出苯乙醇、苄醇、二甲基苄基甲醇、苯乙基二甲基甲醇、苯己醇、Ambrinol(1,2,3,4,4a,5,6,7-八氢-2,5,5-三甲基-萘-2-醇)、Ambrinol 20T(高砂香料工业株式会社商品名、1,2,3,4,4a,5,6,7-八氢-2,5,5-三甲基-萘-2-醇)、Indolene 50BB(IFF公司商品名、7,7-双(1H-吲哚-3-基)-1,1,5-三甲基-1-庚醇)等。
作为脂肪族醇,可以举出顺式-3-己烯醇、1-(2,2,6-三甲基环己基)-3-己醇、Amber Core(花王株式会社商品名、1-(2-叔丁基环己氧基)-2-丁醇)、Sandalmysore Core(花王株式会社商品名、2-甲基-4-(2,2,3-三甲基-3-环戊烯-1-基)-2-丁烯-1-醇)、Magnol(花王株式会社商品名、以乙基降冰片基环己醇为主要成分的混合物)、Undecavertol(Givaudan株式会社商品名、4-甲基-3-癸烯-5-醇)、异冰片基环己醇、Polymeflor(高砂香料工业株式会社商品名、1-(2-甲基-2-丙烯氧基)-2,2,4-三甲基戊烷-3-醇)等。
作为其它的醇,可以举出Florosa(Givaudan公司商品名、化学名:4-甲基-2-(2-甲基丙基)四氢-2H-4-吡喃醇)、癸烯醇等。
作为烃类,可以举出柠檬烯、α-蒎烯、β-蒎烯、松油烯、柏木烯、长叶烯、瓦伦烯、罗勒烯、Ambrotech(花王株式会社商品名、十二氢-3a,6,6,9a-四甲基萘并[2,1-b]呋喃)、Florex(Firmenich Inc.商品名、6-亚乙基八氢-5,8-亚甲基-2H-1-苯并吡喃)、Habanolide(Firmenich Inc.商品名、环十五烯内酯)等。
作为酚类,可以举出愈创木酚、丁香酚、异丁香酚、百里香酚、对甲酚、香兰素、乙基香兰素等。
作为酯类,可以举出脂肪族羧酸酯、芳香族羧酸酯、其它羧酸酯。
作为形成脂肪族羧酸酯的脂肪族羧酸,可以举出碳原子数为1~18的直链及支链羧酸,其中,甲酸、乙酸、丙酸等的碳原子数为1~6的羧酸、特别是乙酸是重要的。作为形成芳香族羧酸酯的芳香族羧酸,可以举出苯甲酸、茴香酸、苯乙酸、肉桂酸、水杨酸、邻氨基苯甲酸等。作为形成脂肪族及芳香族酯的醇,可以举出碳原子数为1~5的直链及支链脂肪族醇以及上述的香料成分醇类。
作为甲酸酯,可以举出甲酸芳樟酯、甲酸香茅酯、甲酸香叶酯等。
作为乙酸酯,可以举出乙酸己酯、乙酸顺式-3-己烯酯、乙酸芳樟酯、乙酸香茅酯、乙酸香叶酯、乙酸橙花酯、乙酸萜品酯、乙酸诺卜酯(nopyl acetate)、乙酸冰片酯、乙酸异冰片酯、乙酰丁香酚、乙酰异丁香酚、乙酸邻叔丁基环己酯、乙酸对叔丁基环己酯、乙酸三环癸烯酯、乙酸苄酯、乙酸苯基乙酯、乙酸苏合香酯(styralyl acetate)、乙酸肉桂酯、乙酸二甲基苄基原酯、乙酸苯乙基苯酯、3-戊基四氢吡喃-4-基乙酸酯、苯乙酸对甲酚酯等。
作为丙酸酯,可以举出丙酸香茅酯、丙酸三环癸烯酯、丙酸烯丙基环己酯、2-环己基丙酸乙酯、丙酸苄酯、丙酸苏合香酯等。
作为丁酸酯,可以举出丁酸香茅酯、正丁酸二甲基苄基原酯、异丁酸三环癸烯酯等。
作为戊酸酯,可以举出戊酸甲酯、戊酸乙酯、戊酸丁酯、戊酸戊酯、戊酸苄酯、戊酸苯基乙酯等;作为己酸酯,可以举出己酸甲酯、己酸乙酯、己酸烯丙酯、己酸里哪酯、己酸香茅酯等。
作为庚酸酯,可以举出庚酸甲酯、庚酸烯丙酯等。
作为壬酸酯,可以举出2-壬烯酸甲酯、2-壬烯酸乙酯、3-壬烯酸乙酯等。
作为苯甲酸酯,可以举出苯甲酸甲酯、苯甲酸苄酯、3,6-二甲基苯甲酸酯等。
作为肉桂酸酯,可以举出肉桂酸甲酯、肉桂酸苄酯、肉桂酸苯乙酯等。
作为水杨酸酯,可以举出水杨酸甲酯、水杨酸正己酯、水杨酸顺式-3-己烯酯、水杨酸环己酯、水杨酸苄酯等。
进一步,作为巴西酸酯,可以举出巴西酸亚乙酯(ethylene brassylate)等。
作为惕格酸酯(Tiglic acid ester),可以举出惕格酸香叶酯、惕格酸1-己酯、惕格酸顺式-3-己烯酯等。
作为茉莉酸酯,可以举出茉莉酸甲酯、二氢茉莉酸甲酯等。
作为缩水甘油酸酯,可以举出2,4-二羟基-乙基甲基苯基缩水甘油酸甲酯、4-甲基苯基乙基缩水甘油酸酯等。
作为邻氨基苯甲酸酯,可以举出邻氨基苯甲酸甲酯、邻氨基苯甲酸乙酯、邻氨基苯甲酸二甲酯等。
进一步,作为其它的酯,可以举出Ethyl Safranate(Givaudan公司商品名、二氢环香叶酸乙酯)、Poirenate(花王株式会社商品名、2-环己基丙酸乙酯)、Fruitate(花王株式会社商品名、三环[5.2.1.02.6]癸烷-2-羧酸乙酯)、茉莉酸甲酯、MDJ(花王株式会社商品名、二氢茉莉酮酸甲酯、(2-戊基-3-氧代环戊基)乙酸甲酯)、水杨酸环己酯(花王株式会社商品名)、I.P.M(肉豆蔻酸异丙酯)等。
作为碳酸酯类,可以举出Liffarome(IFF公司商品名、顺式-3-己烯基甲基碳酸酯)、Jasmacyclat(花王株式会社商品名、甲基环辛基碳酸酯)、Floramat(花王株式会社商品名、乙基-2-叔丁基环乙基碳酸酯)等。
作为醛类,可以举出正辛醛、正壬醛、正癸醛、正十二醛、2-甲基十一醛、10-十一碳烯醛、香茅醛、柠檬醛、羟基香茅醛、Triplal(IFF公司商品名、2,4-二甲基-3-环己烯-1-甲醛)、Cyclovertal(花王株式会社商品名、二甲基-3-环己烯基-1-甲醛)、苯甲醛、苯乙醛、苯丙醛、肉桂醛、二甲基四氢苯甲醛、Bourgeonal(Givaudan公司商品名、3-(4-叔丁基苯基)丙醛)、Lyral(IFF公司商品名、羟基柑青醛)、POLLENAL II(花王株式会社商品名、2-环己基丙醛)、Lilial(Givaudan公司商品名、对叔丁基-α-甲基氢化肉桂醛)、对异丙基-α-甲基氢化肉桂醛、Floralozone(IFF公司商品名、3-(邻-(和对-)乙基苯基)-2,2-二甲基丙醛)、α-戊基肉桂醛、α-己基肉桂醛、胡椒醛、Helional(IFF公司商品名、α-甲基-1,3-苯并二恶唑-5-丙醛)等。
作为酮类,可以举出甲基庚烯酮、二甲基辛烯酮、3-辛酮、己基环戊酮、二氢茉莉酮、Veloutone(Firmenich Inc.商品名、2,2,5-三甲基-5-戊基环戊酮)、Nectaryl(Givaudan公司商品名、2-(2-(4-甲基-3-环己烯-1-基)丙基)环戊酮)、紫罗兰酮、β-紫罗兰酮、甲基紫罗兰酮、甲基紫罗兰酮-G、γ-甲基紫罗兰酮、大马酮(Damascone)、α-大马酮、β-大马酮、δ-大马酮、异大马酮(Symrise公司商品名、1-(2,4,4-三甲基-2-环己基)-反式-2-丁酮)、大马烯酮(Damascenone)、Dynascone(Firmenich Inc.商品名、1-(5,5-二甲基-1-环己烯-1-基)-4-戊烯-1-酮)、鸢尾酮、Cashmeran(IFF公司商品名、1,2,3,5,6,7-六氢-1,1,2,3,3-五甲基-4H-茚-4-酮),Iso E Super(IFF公司商品名、1-(1,2,3,4,5,6,7,8-八氢-2,3,8,8-四甲基-2-萘基-乙烷-1-酮)、Calone(Firmenich Inc.商品名、7-甲基-3,4-二氢-2H-苯并二氧环丙-3-酮)、香芹酮、薄荷酮、l-薄荷酮、乙酰基柏木烯、异长叶烷酮、诺卡酮(nootkatone)、苄基丙酮、覆盆子酮、二苯甲酮、Tonalid(PFW公司商品名、6-乙酰基-1,1,2,4,4,7-六甲基四氢化萘)、β-甲基萘基酮、乙基麦芽酚、樟脑、麝香酮(3-甲基环十五烷酮)、l-麝香酮((R)-3-甲基环十五烷酮)、Muscenone(Firmenich Inc.商品品、3-甲基-5-环十五碳烯-1-酮)、灵猫酮(Civetone)、Globanone(Symrise公司商品名、8-环十六烯酮)、甲基壬基酮、顺式茉莉酮、Florantone T(高砂香料工业株式会社商品名、1-(5,6,7,8-四氢-2-萘基)乙酮)、麝香TM-II(曾田香料株式会社商品名、5-环十六碳烯-1-酮)、麝香Z-4(IFF公司商品名、(Z)-4-环十五碳烯-1-酮)、Veloutone(Firmenich Inc.商品名、2,5,5-三甲基-2-戊基环戊酮)等。其中,从通过与其它香料调配来强调花的甜味的观点出发,优选紫罗兰酮、大马烯酮、Iso E Super、或γ-甲基紫罗兰酮。
作为缩醛类,可以举出乙醛乙基苯基丙基缩醛、柠檬醛二乙缩醛、苯乙醛甘油缩醛、乙酰乙酸乙酯乙二醇缩醛、Boisambrene Forte(花王株式会社商品名)、Troenan(花王株式会社商品名)等。
作为醚类,可以举出乙基芳樟醇、甲基柏木醚、草蒿脑、茴香脑、β-萘基甲基醚、β-萘基乙基醚、柠檬烯氧化物、玫瑰醚、橙花醚、1,8-桉叶素、玫瑰呋喃、Ambroxan(花王株式会社商品名、[3aR-(3aα,5aβ,9aα,9bβ)]十二氢-3a,6,6,9a-四甲基萘[2,1-b]呋喃)、Herbavert(花王株式会社商品名、3,3,5-三甲基环己基乙基醚)、Galaxolide(IFF公司商品名、六甲基六氢环戊苯并吡喃)、苯乙醛二甲缩醛、Boisambrene Forte(花王株式会社商品名、乙氧基甲基环十二烷基醚)等。
作为羧酸类,可以举出苯甲酸、苯乙酸、肉桂酸、氢化肉桂酸、丁酸、2-己酸等。
作为除化合物(I)以外的内酯类,可以举出γ-癸内酯、δ-癸内酯、γ-戊内酯、γ-壬内酯、γ-十一内酯、δ-己内酯、γ-茉莉内酯、威士忌内酯、香豆素、环十五烷内酯、环十六烷内酯、11-氧杂十六烷内酯、丁烯基酞内酯等。
作为腈类,可以举出香叶腈、香茅腈、十二腈等。
作为席夫碱类,可以举出橙花素(Aurantiol)、LIGANTRAL等。
作为天然精油或天然提取物,可以举出橙子、柠檬、酸橙、佛手柑、香草、橘皮、薄荷、留兰香、薰衣草、洋甘菊、迷迭香、桉树、鼠尾草、罗勒、玫瑰、岩玫瑰、天竺葵、茉莉、依兰、茴芹、丁香、姜、肉豆蔻、小豆蔻、雪松、柏树、香根草、广藿香、柠檬草、岩蔷薇、葡萄柚、桉树叶油、花生木油等。
这些其它香料的含量可以根据调和香料的种类、目标的香气的种类以及香气的强度等适当选择,在组合物中其它香料的含量分别优选为0.0001质量%以上、更优选为0.001质量%以上,并且优选为99.99质量%以下、更优选为80质量%以下。此外,其它香料的总含量在组合物中优选为5质量%以上、更优选为50质量%以上,并且优选为99.99质量%以下、更优选为99.95质量%以下。
本发明的组合物作为含有E型和Z型的比率为特定比例的通式(I)所表示的化合物、以及其它香料原材料香基,可以含有其自身不具有气味的油剂。这样的油剂可以使香料成分均匀地混合,容易配合于产品,容易地赋香适度强度的香味。作为所述油剂的例子,可以举出乙二醇、丙二醇、丁二醇、二丙二醇等的多元醇;肉豆蔻酸异丙酯、己二酸二丁酯、癸二酸二乙酯等的酯;液体石蜡、角鲨烷等的烃;聚氧乙烯烷基醚、山梨糖醇酐脂肪酸酯等的表面活性剂等。
其中,从全部香料成分的溶解性的观点出发,作为所述油剂,优选多元醇和酯,更优选二丙二醇和肉豆蔻酸异丙酯。这样的油剂在组合物中的含量优选为0.01质量%以上、更优选为1质量%以上、进一步优选为5质量%以上,并且优选为95质量%以下、更优选为90质量%以下、更优选为80质量%以下。
本发明还提供一种含有本发明的组合物的清洁剂、含有本发明的组合物的化妆品、以及含有本发明的组合物的纤维处理剂。
作为本发明的清洁剂,优选为身体用清洁剂、衣物用清洁剂、硬质表面用清洁剂,更优选为身体用清洁剂、衣物用清洁剂,进一步优选为衣物用清洁剂。
作为身体用清洁剂的例子,可以举出皮肤用清洁剂、毛发用清洁剂、肥皂,优选为皮肤用清洁剂。
作为硬质表面用清洁剂的例子,可以举出多用途清洁剂(All purpose Cleaner)、餐具用清洁剂。
作为本发明的纤维处理剂,优选为柔软剂。
作为本发明的化妆品,优选为香水、乳液、化妆水、防晒霜,更优选为香水。
在本发明的清洁剂中,除了本发明的组合物以外,优选含有阴离子表面活性剂,还可以配合非离子表面活性剂、pH调节剂、粘度调节剂、溶剂、油剂、防腐剂、水等。
在本发明的纤维处理剂中,除了本发明的组合物以外,优选含有阳离子表面活性剂,还可以配合pH调节剂、溶剂、油剂、防腐剂、水等。
在本发明的香料中,除了本发明的组合物以外,可以配合溶剂、水等。
包含E型和Z型的比例为特定比例的通式(I)所表示的化合物的本发明的组合物是麝香味组合物,如上所述,与其它各种香料的调和性优异,并且通过调配而能够创造出特征性香味的效果。因此,如上所述,本发明是将上述组合物作为赋香成分使用的方法,具体地说,是作为组合物、清洁剂、化妆品或纤维处理剂的赋香成分使用的方法。作为所述清洁剂,优选为身体用清洁剂、衣物用清洁剂、硬质表面用清洁剂,更优选为身体用清洁剂、衣物用清洁剂,更优选为衣物用清洁剂。作为所述身体用清洁剂的例子,可以举出皮肤用清洁剂、头发用清洁剂、肥皂,优选为皮肤用清洁剂。作为所述硬质表面用清洁剂的例子,可以举出多用途清洁剂(All purpose Cleaner)、餐具用清洁剂。作为所述化妆品,优选为香水。作为所述纤维处理剂,优选为柔软剂。
在上述使用的方法中,所述组合物相对于清洁剂、化妆品或柔软剂以优选为0.00001质量%以上、更优选为0.0001质量%以上,且优选为0.01质量%以下、更优选为0.001质量%以下的量使用。通过以该量使用,与各种香料的调和性优异,可以赋予通过调配而能够创造出特征性香味的效果的麝香的香气。
在所述使用的方法中,所述组合物相对于香水以优选为0.0001质量%以上、更优选为0.001质量%以上,且优选为0.1质量%以下、更优选为0.01质量%以下的量使用。通过以该量使用,与各种香料的调和性优异,可以赋予通过调配而能够创造出特征性香味的效果的麝香的香气。
在所述使用的方法中,在将所述组合物用作赋香成分的组合物中,也可以含有其自身不具有气味的油剂。关于所述油剂,与在上述组合物中说明的相同。此外,在所述使用的方法中,在将所述组合物作为赋香成分使用的组合物中,除了上述组合物(即,含有E型和Z型的比例为特定比例的通式(I)所表示的化合物)以外,还可以含有通常使用的其它香料成分或所希望组成的调和香料作为其它香料。作为这样的其它香料,与在上述组合物中说明的相同。
在所述使用的方法中,将所述组合物用作赋香成分的清洁剂、化妆品或柔软剂中,也可以含有其自身不具有气味的油剂。关于所述油剂,与在上述组合物中说明的相同。此外,在所述使用的方法中,在将所述组合物作为赋香成分使用的清洁剂、化妆品或柔软剂中,除了E型和Z型的比例为特定比例的通式(I)所表示的化合物以外,还可以含有通常使用的其它香料成分或所希望组成的调和香料作为其它香料。作为这样的其它香料,与在上述组合物中说明的相同。
关于上述实施方式,本发明进一步公开以下的组合物。
<1>一种组合物,其中,所述组合物含有通式(I)所表示的化合物,所述通式(I)所表示的化合物的E型和所述通式(I)所表示的化合物的Z型的比例为E型/Z型=3/7以上7/3以下。
<2>如<1>所述的组合物,其中,所述通式(I)所表示的化合物的E型和所述通式(I)所表示的化合物的Z型的比例为E型/Z型=5/5以上7/3以下。
<3>如<1>或<2>所述的组合物,其中,含有通式(I)所表示的化合物以外的香料,所述通式(I)所表示的化合物的含量为0.01质量%以上25质量%以下。
<4>如<3>所述的组合物,其中,所述通式(I)所表示的化合物以外的香料为烃类、醇类、酚类、醛类、酮类、缩醛类、醚类、酯类、碳酸酯类、除化合物(I)以外的内酯类、羧酸类、腈类、席夫碱类、天然精油和天然提取物中的1种以上。
<5>如<3>或<4>所述的组合物,其中,通式(I)所表示的化合物与所述通式(I)所表示的化合物以外的香料的比率[通式(I)所表示的化合物/所述通式(I)所表示的化合物以外的香料]为1/1000以上、更优选为5/1000以上、更优选为10/1000以上。
<6>如<3>~<5>中任一项所述的组合物,其中,通式(I)所表示的化合物与所述通式(I)所表示的化合物以外的香料的比率[通式(I)所表示的化合物/所述通式(I)所表示的化合物以外的香料]为100/1000以下、更优选为50/1000以下、更优选为25/1000以下。
<7>如<3>~<6>中任一项所述的组合物,其中,所述通式(I)所表示的化合物以外的香料是酯类,更优选为二氢茉莉酮酸甲酯。
<8>如<7>所述的组合物,其中,通式(I)所表示的化合物与所述酯类的香料的比率[通式(I)所表示的化合物/酯类的香料]为1/1000以上、更优选为10/1000以上、更优选为20/1000以上。
<9>如<7>或<8>所述的组合物,其中,通式(I)所表示的化合物与所述酯类的香料的比率[通式(I)所表示的化合物/酯类的香料]为100/1000以下、更优选为50/1000以下、更优选为40/1000以下。
<10>如<3>或<4>所述的组合物,其中,所述通式(I)所表示的化合物以外的香料是醚类,更优选为六甲基六氢环戊苯并吡喃。
<11>如<10>所述的组合物,其中,通式(I)所表示的化合物与所述醚类香料的比率[通式(I)所表示的化合物/醚类的香料]为1/1000以上、更优选为5/1000以上、更优选为10/1000以上。
<12>如<10>或<11>所述的组合物,其中,通式(I)所表示的化合物与所述醚类香料的比率[通式(I)所表示的化合物/醚类的香料]为100/1000以下、更优选为50/1000以下、更优选为25/1000以下。
<13>如<3>或<4>所述的香料组合物,其中,所述通式(I)所表示的化合物以外的香料是醇类,更优选为芳香族醇,更优选为苯乙醇。
<14>如<13>所述的组合物,其中,通式(I)所表示的化合物与所述醇类的香料的比率[通式(I)所表示的化合物/醇类的香料]为1/1000以上、更优选为5/1000以上、更优选为10/1000以上。
<15>如<13>或<14>所述的组合物,其中,通式(I)所表示的化合物与所述醇类的香料的比率[通式(I)所表示的化合物/醇类的香料]为100/1000以下、更优选为50/1000以下、更优选为25/1000以下。
<16>如<3>~<15>中任一项所述的组合物,其中,所述通式(I)所表示的化合物以外的香料是化合物(I)以外的麝香类香料,更优选为选自Galaxolide(IFF公司商品名、六甲基六氢环戊苯并吡喃)、Habanolide(Firmenich Inc.商品名、环十五烯内酯)、l-麝香酮((R)-3-甲基环十五烷酮)、麝香酮(3-甲基环十五烷酮)、麝香TM-II(曾田香料株式会社商品名、5-环十六碳烯-1-酮)以及麝香Z-4(IFF公司商品名、(Z)-4-环十五碳烯-1-酮)中的1种以上。
<17>如<16>所述的组合物,其中,通式(I)所表示的化合物与所述麝香类香料的比率[通式(I)所表示的化合物/麝香类香料]为1/1000以上、更优选为5/1000以上、更优选为10/1000以上。
<18>如<16>或<17>所述的组合物,其中,通式(I)所表示的化合物与上述麝香类香料的比率[通式(I)所表示的化合物/麝香类香料]为100/1000以下、更优选为50/1000以下、更优选为25/1000以下。
<19>一种清洁剂,其中,含有<1>~<18>中任一项所述的组合物。
<20>一种化妆品,其中,含有<1>~<18>中任一项所述的组合物。
<21>一种纤维处理剂,其中,含有<1>~<18>中任一项所述的组合物。
<22>一种将<1>~<18>所述的组合物作为赋香成分使用的方法。
<23>一种将<1>~<18>所述的组合物作为赋香成分的用途。
<24>一种增强整体香味的方法,其中,将<1>~<18>所述的组合物作为赋香成分。
<25>一种将<1>~<18>所述的组合物作为赋香成分用于增强整体香味的用途。
<26>一种增加麝香的柔和性的方法,其中,将<1>~<18>所述的组合物作为赋香成分。
<27>一种将<1>~<18>所述的组合物作为赋香成分用于增加麝香的柔和性的用途。
实施例
以下一并示出在以下的实施例和比较例等中进行的测定方法的详细情况。
[化合物的鉴定]
以下的制造例中得到的各化合物通过利用1H-NMR和气相色谱质谱(GC-MS)分析仪(岛津制作所公司制造、型号:GC-2010)的光谱分析得到的数据与公知文献等公开的化合物数据一致来鉴定化合物。
[香气评价]
由2名具有调香·香料评价工作经验者通过闻香纸法判定香调和强度。将闻香纸(宽6mm长150mm的香料试纸)的前端约5mm浸渍于样品中,并进行评价。
对于香气,备注次要地感受到的香味(副香气)。调和香料的评价将不含有本发明的组合物的样品作为空白,评价从空白起的香调的变化。
实施例中使用的化合物(I)的E型和Z型通过以下的制造例制造。
另外,化合物(I)的E型为(E)-氧代环十七碳-8-烯-2-酮,化合物(I)的Z型为(Z)-氧代环十七碳-8-烯-2-酮。
[制造例1]
E型/Z型的比率为91/9的氧代环十七碳-8-烯-2-酮混合物的合成方法
[制造例1]
(a)9-癸烯基-7-辛烯酸酯的制造
在烧瓶中加入9-癸烯-1-醇(东京化成工业株式会社制造、2.2g、14.0毫摩尔)和7-辛烯酸(Aldrich Company制造、2.0g、14.0毫摩尔),使其溶解于二氯甲烷(30mL)中。接着,在上述烧瓶中添加1-乙基-3(3-二甲基氨基丙基)碳二亚胺盐酸盐(3.2g、16.8毫摩尔)和N,N'-二甲基氨基吡啶(171mg、1.4毫摩尔),在氮气流下,在室温下使其反应3小时。在反应结束液中加入氯化铵水溶液并搅拌后,静置分层抽出水层,用饱和食盐水清洗油层后,加入硫酸钠进行脱水干燥。经过过滤后,从上述油层中馏去二氯甲烷,以100%的粗收率得到了9-癸烯基-7-辛烯酸酯(3.9g、14.0毫摩尔)。
(b)(E)-氧代环十七碳-8-烯-2-酮的制造
在三口烧瓶中加入上述工序(a)中获得的9-癸烯基-7-辛烯酸酯(3.3g、11.8毫摩尔)、二氯甲烷(3L)、以及下述式所示的置换催化剂(商品名“Umicore M2”、Umicore JapanCo.,Ltd.制造、194mg、0.21毫摩尔),在氮气流下加热回流(50℃)24小时后,追加添加130mg(0.14毫摩尔)下述式所示的置换催化剂,进一步持续搅拌5小时。对反应结束液进行气相色谱定量分析,结果氧代环十七碳-8-烯-2-酮包含2.0g(E/Z=70/30,7.9毫摩尔,收率67%)。
从该反应溶液中馏去二氯甲烷,将残余物通过硅胶柱色谱法精制(展开剂为正己烷:乙酸乙酯=95:5),得到0.3g(E)-氧代环十七碳-8-烯-2-酮(E/Z=91/9)。
[制造例2]
E型/Z型的比率为2/98的氧代环十七碳-8-烯-2-酮的混合物的合成方法
在三口烧瓶中加入制造例1(a)中得到的9-癸烯基-7-辛烯酸酯(0.9g、3.2毫摩尔)、二氯甲烷(1.1L)以及下述式所示的置换催化剂(Aldrich Company制造、100mg、0.16毫摩尔),在氮气流下加热回流(50℃)24小时后,追加添加100mg(0.16毫摩尔)下述式所示的置换催化剂,进一步持续搅拌24小时。对反应结束液进行气相色谱定量分析,结果包含0.4g(Z)-氧代环十七碳-8-烯-2-酮(E/Z=2/98、1.6毫摩尔、收率49%)。
从该反应溶液中馏去二氯甲烷,并将残余物通过硅胶柱色谱法精制(展开剂为正己烷:乙酸乙酯=99:1),得到0.3g(Z)-氧代环十七碳-8-烯-2-酮(E/Z=2/98)。
[实施例1~3以及比较例1~4]
使用制造例1中得到的化合物(I)的混合物(其中,E型/Z型=91/9)和制造例2中得到的化合物(I)的混合物(其中,E型/Z型=2/98),调制表1所示的组成的组合物,进行香气评价。香气评价的结果也示于表1中。
[表1]
如上述表1所示,可以确认比较例的组合物具有稍甜的麝香或有清晰的轮廓的湿润的麝香的香气。另一方面,可以确认本发明的组合物与比较例1和4相比,湿润的香味较强、并且具有有类似醛的甜味的麝香的香气。
[实施例4~6以及比较例5~9]
使用制造例1中得到的化合物(I)的混合物(其中,E型/Z型=91/9)和制造例2中得到的化合物(I)的混合物(其中,E型/Z型=2/98),调制表2所示的组成的香水。对得到的香水进行香气评价,其香气评价的结果如表3所示。
[表2]
*表中的数字是重量比。
1)Ambroxan(花王株式会社商品名、[3aR-(3aα,5aβ,9aα,9bβ)]十二氢-3a,6,6,9a-四甲基萘[2,1-b]呋喃)
2)D.P.G:二丙二醇
3)MDJ(花王株式会社商品名、二氢茉莉酮酸甲酯、(2-戊基-3-氧代环戊基)乙酸甲酯)
4)Iso E Super(IFF公司商品名、1-(1,2,3,4,5,6,7,8-八氢-2,3,8,8-四甲基-2-萘基)-乙烷-1-酮)
5)Liffarome(IFF公司商品名、顺式-3-己烯基碳酸酯)
6)Lilial(Givaudan公司商品名、对叔丁基-α-甲基氢化肉桂醛)
7)Veloutone(Firmenich Inc.商品名、2,2,5-三甲基-5-戊基环戊酮)
8)Amber core(花王株式会社商品名、1-(2-叔丁基环己氧基)-2-丁醇)
9)Florosa(Givaudan公司商品名、化学名:4-甲基-2-(2-甲基丙基)四氢-2H-4-吡喃醇)
[表3]
如表3所示,可以确认比较例的香水与不含化合物(I)的空白(比较例5)相比,增加了麝香的甜味,整体协调。另一方面,可以确认本发明的香水与不含化合物(I)的空白(比较例5)相比,增加了麝香的甜味,整体协调,并且通过类似醛的甜味,香味整体变强。
[实施例7~9以及比较例10~14]
使用制造例1中得到的化合物(I)的混合物(其中,E型/Z型=91/9)和制造例2中得到的化合物(I)的混合物(其中,E型/Z型=2/98),调制表4所示的组成的香水。对得到的香水进行香气评价,其香气评价的结果如表5所示。
[表4]
*表中的数字为重量比。
1)Amber Core(花王株式会社商品名、1-(2-叔丁基环己氧基)-2-丁醇)
2)Ambrinol(商品名、1,2,3,4,4a,5,6,7-八氢-2,5,5-三甲基-萘-2-醇)
3)Ambrinol 20T(高砂香料工业株式会社商品名、1,2,3,4,4a,5,6,7-八氢-2,5,5-三甲基-萘-2-醇)
4)Ambrotech(花王株式会社商品名、十二氢-3a,6,6,9a-四甲基萘并[2,1-b]呋喃)
5)Ambroxan(花王株式会社商品名、[3aR-(3aα,5aβ,9aα,9bβ)]十二氢-3a,6,6,9a-四甲基萘[2,1-b]呋喃)
6)Boisambrene Forte(花王株式会社商品名、乙氧基甲基环十二烷基醚)
7)D.P.G:二丙二醇
8)Florantone T(高砂香料工业株式会社商品名、1-(5,6,7,8-四氢-2-萘基)乙酮
9)Florex(Firmenich Inc.商品名、6-亚乙基八氢-5,8-亚甲基-2H-1-苯并吡喃)
10)Galaxolide(IFF公司商品名、六甲基六氢环戊苯并吡喃)
11)Globanone(Symrise公司商品名、8-环十六烯酮)
12)Habanolide(Firmenich Inc.商品名、环十五烯内酯)
13)Indolene 50BB(IFF公司商品名、7,7-双(1H-吲哚-3-基)-1,1,5-三甲基-1-庚醇)
14)l-麝香酮((R)-3-甲基环十五烷酮)
15)麝香酮(3-甲基环十五烷酮)
16)麝香TM-II(曾田香料株式会社商品名、5-环十六碳烯-1-酮)
17)麝香Z-4(IFF公司商品名、(Z)-4-环十五碳烯-1-酮)
18)Polymeflor(高砂香料工业株式会社商品名、1-(2-甲基-2-丙烯氧基)-2,2,4-三甲基戊烷-3-醇)
[表5]
如表5所示,可以确认比较例的香水与不含化合物(I)的空白(比较例10)相比,麝香的甜味增加。另一方面,可以确认本发明的香水与不含化合物(I)的空白相比(比较例10)增加了麝香的甜味,整体协调,并且香味变得立体,产生清洁感。
[实施例10~12以及比较例15~19]
使用制造例1中得到的化合物(I)的混合物(其中,E型/Z型=91/9)和制造例2中得到的化合物(I)的混合物(其中,E型/Z型=2/98),调制表6所示的组成的香水。对得到的香水进行香气评价,其香气评价的结果如表7所示。
[表6]
*表中的数字为重量比。
1)α-松油醇(2-(4-甲基环己-3-烯基)丙烷-2-醇)
2)I.P.M(肉豆蔻酸异丙酯)
3)MDJ(花王株式会社商品名、二氢茉莉酮酸甲酯、(2-戊基-3-氧代环戊基)乙酸甲酯)
4)Triplal(IFF公司商品名、2,4-二甲基-3-环己烯-1-甲醛)
5)Veloutone(Firmenich Inc.商品名、2,5,5-三甲基-2-戊基环戊酮)
[表7]
如表7所示,可以确认比较例的香水与不含化合物(I)的空白(比较例15)相比,麝香的甜味增加。另一方面,可以确认本发明的香水与不含化合物(I)的空白(比较例15)相比,增加了麝香的甜味,玫瑰的香味柔和地扩散,香味整体的分量感增强。
产业上利用的可能性
本发明的组合物具有作为香料有用的麝香调的香气,因此,可以用作香料原材料。此外,本发明的组合物与其它各种香料的调和性优异,可以通过调配而创造出特征性香味的效果,因此,可以作为赋香成分使用。
Claims (10)
2.如权利要求1所述的组合物,其中,
所述通式(I)所表示的化合物的E型和所述通式(I)所表示的化合物的Z型的比率为E型/Z型=5/5以上7/3以下。
3.如权利要求1或2所述的组合物,其中,
含有通式(I)所表示的化合物以外的香料,所述通式(I)所表示的化合物的含量为0.01质量%以上25质量%以下。
4.如权利要求3所述的组合物,其中,
所述通式(I)所表示的化合物以外的香料是烃类、醇类、酚类、醛类、酮类、缩醛类、醚类、酯类、碳酸酯类、除化合物(I)以外的内酯类、羧酸类、腈类、席夫碱类、天然精油和天然提取物中的1种以上。
5.一种清洁剂,其中,
含有权利要求1~4中任一项所述的组合物。
6.一种化妆品,其中,
含有权利要求1~4中任一项所述的组合物。
7.一种纤维处理剂,其中,
含有权利要求1~4中任一项所述的组合物。
8.一种将权利要求1~4中任一项所述的组合物作为赋香成分使用的方法。
9.一种增强整体香味的方法,其中,
将权利要求1~4中任一项所述的组合物作为赋香成分。
10.一种增加麝香的柔和性的方法,其中,
将权利要求1~4中任一项所述的组合物作为赋香成分。
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US3681395A (en) * | 1970-03-11 | 1972-08-01 | Int Flavors & Fragrances Inc | Preparation of ambrettolide |
US5726328A (en) * | 1996-07-09 | 1998-03-10 | V. Mane Fils S.A. | Preparation of cis-isoambrettolides and their use as a fragrance |
CN106661498A (zh) * | 2014-07-07 | 2017-05-10 | 西姆莱斯有限公司 | 不饱和大环麝香化合物的异构体混合物 |
CN106687099A (zh) * | 2014-09-26 | 2017-05-17 | 宝洁公司 | 包含恶臭减少组合物的个人护理组合物 |
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DE69028755T2 (de) * | 1989-10-27 | 1997-06-05 | Firmenich & Cie | Verwendung von ungesättigten macrocyclischen Ketonen sowie Parfumingredienzen |
JP3040449U (ja) | 1997-02-10 | 1997-08-19 | コスモ株式会社 | 合成樹脂製スナップ付きバイアステープ |
EP0908455B1 (de) | 1997-10-09 | 2002-07-10 | Givaudan SA | Macrocyclen |
FR2775285B1 (fr) | 1998-02-20 | 2000-04-14 | Synarome H Fraysse Et Cie | Procede de fabrication de la cis-isoambrettolide et son application |
US9073801B2 (en) | 2011-06-03 | 2015-07-07 | Massachusetts Institute Of Technology | Z-selective ring-closing metathesis reactions |
GB201404468D0 (en) | 2014-03-13 | 2014-04-30 | Givaudan Sa | Process |
JP6794108B2 (ja) | 2014-12-26 | 2020-12-02 | 花王株式会社 | ω−ヒドロキシ脂肪酸エステルおよびその前駆体化合物の製造方法 |
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Publication number | Priority date | Publication date | Assignee | Title |
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US3681395A (en) * | 1970-03-11 | 1972-08-01 | Int Flavors & Fragrances Inc | Preparation of ambrettolide |
US5726328A (en) * | 1996-07-09 | 1998-03-10 | V. Mane Fils S.A. | Preparation of cis-isoambrettolides and their use as a fragrance |
CN106661498A (zh) * | 2014-07-07 | 2017-05-10 | 西姆莱斯有限公司 | 不饱和大环麝香化合物的异构体混合物 |
CN106687099A (zh) * | 2014-09-26 | 2017-05-17 | 宝洁公司 | 包含恶臭减少组合物的个人护理组合物 |
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