CN114746071A - 新颖感官化合物 - Google Patents
新颖感官化合物 Download PDFInfo
- Publication number
- CN114746071A CN114746071A CN202080082344.5A CN202080082344A CN114746071A CN 114746071 A CN114746071 A CN 114746071A CN 202080082344 A CN202080082344 A CN 202080082344A CN 114746071 A CN114746071 A CN 114746071A
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- Prior art keywords
- buffers
- hydroxy
- enal
- formulation
- fragrance
- Prior art date
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- 150000001875 compounds Chemical class 0.000 title claims abstract description 43
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- 238000009472 formulation Methods 0.000 claims description 44
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- 239000000872 buffer Substances 0.000 claims description 40
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- 235000019634 flavors Nutrition 0.000 claims description 21
- -1 silicas Polymers 0.000 claims description 19
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- 239000003599 detergent Substances 0.000 claims description 9
- 239000007788 liquid Substances 0.000 claims description 9
- 125000002947 alkylene group Chemical group 0.000 claims description 8
- 239000002304 perfume Substances 0.000 claims description 8
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- 239000004744 fabric Substances 0.000 claims description 7
- 238000000034 method Methods 0.000 claims description 7
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- RAXXELZNTBOGNW-UHFFFAOYSA-N imidazole Natural products C1=CNC=N1 RAXXELZNTBOGNW-UHFFFAOYSA-N 0.000 claims description 6
- SDLDFWVJXIZHCP-UHFFFAOYSA-N OC(CCC(CCC=C(CCC=O)C)C)C Chemical compound OC(CCC(CCC=C(CCC=O)C)C)C SDLDFWVJXIZHCP-UHFFFAOYSA-N 0.000 claims description 5
- OBJGEWZQRFEKQB-UHFFFAOYSA-N OCCCC(CCC=C(CCC=O)C)C Chemical compound OCCCC(CCC=C(CCC=O)C)C OBJGEWZQRFEKQB-UHFFFAOYSA-N 0.000 claims description 5
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- JOSLAGASMJFNLV-UHFFFAOYSA-N 10-hydroxy-4,8-dimethyldec-4-enal Chemical compound OCCC(C)CCC=C(C)CCC=O JOSLAGASMJFNLV-UHFFFAOYSA-N 0.000 claims description 4
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- YGSDEFSMJLZEOE-UHFFFAOYSA-M salicylate Chemical compound OC1=CC=CC=C1C([O-])=O YGSDEFSMJLZEOE-UHFFFAOYSA-M 0.000 description 1
- 229960001860 salicylate Drugs 0.000 description 1
- 150000003839 salts Chemical class 0.000 description 1
- 229920006395 saturated elastomer Polymers 0.000 description 1
- 229910000338 selenium disulfide Inorganic materials 0.000 description 1
- JNMWHTHYDQTDQZ-UHFFFAOYSA-N selenium sulfide Chemical compound S=[Se]=S JNMWHTHYDQTDQZ-UHFFFAOYSA-N 0.000 description 1
- 229960005265 selenium sulfide Drugs 0.000 description 1
- 239000010865 sewage Substances 0.000 description 1
- 238000010898 silica gel chromatography Methods 0.000 description 1
- 235000011888 snacks Nutrition 0.000 description 1
- 239000012279 sodium borohydride Substances 0.000 description 1
- 229910000033 sodium borohydride Inorganic materials 0.000 description 1
- 235000010265 sodium sulphite Nutrition 0.000 description 1
- KWVISVAMQJWJSZ-VKROHFNGSA-N solasodine Chemical compound O([C@@H]1[C@@H]([C@]2(CC[C@@H]3[C@@]4(C)CC[C@H](O)CC4=CC[C@H]3[C@@H]2C1)C)[C@@H]1C)[C@]11CC[C@@H](C)CN1 KWVISVAMQJWJSZ-VKROHFNGSA-N 0.000 description 1
- 239000002904 solvent Substances 0.000 description 1
- 239000007858 starting material Substances 0.000 description 1
- 238000003860 storage Methods 0.000 description 1
- 235000021012 strawberries Nutrition 0.000 description 1
- 235000000346 sugar Nutrition 0.000 description 1
- 150000008163 sugars Chemical class 0.000 description 1
- 239000000271 synthetic detergent Substances 0.000 description 1
- 229940116411 terpineol Drugs 0.000 description 1
- 239000004753 textile Substances 0.000 description 1
- 238000009988 textile finishing Methods 0.000 description 1
- 238000004227 thermal cracking Methods 0.000 description 1
- 150000003573 thiols Chemical class 0.000 description 1
- 239000008377 tooth whitener Substances 0.000 description 1
- 239000000606 toothpaste Substances 0.000 description 1
- 229940034610 toothpaste Drugs 0.000 description 1
- XJPBRODHZKDRCB-UHFFFAOYSA-N trans-alpha-ocimene Natural products CC(=C)CCC=C(C)C=C XJPBRODHZKDRCB-UHFFFAOYSA-N 0.000 description 1
- 239000000341 volatile oil Substances 0.000 description 1
- 238000005406 washing Methods 0.000 description 1
- 239000010457 zeolite Substances 0.000 description 1
- IHPKGUQCSIINRJ-UHFFFAOYSA-N β-ocimene Natural products CC(C)=CCC=C(C)C=C IHPKGUQCSIINRJ-UHFFFAOYSA-N 0.000 description 1
Classifications
-
- 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
- C11D3/16—Organic compounds
- C11D3/20—Organic compounds containing oxygen
- C11D3/2072—Aldehydes-ketones
-
- 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
- A61K8/33—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds containing oxygen
- A61K8/34—Alcohols
- A61K8/342—Alcohols having more than seven atoms in an unbroken chain
-
- 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
- A61K8/33—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds containing oxygen
- A61K8/34—Alcohols
-
- 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
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C47/00—Compounds having —CHO groups
- C07C47/20—Unsaturated compounds having —CHO groups bound to acyclic carbon atoms
- C07C47/26—Unsaturated compounds having —CHO groups bound to acyclic carbon atoms containing hydroxy groups
- C07C47/263—Unsaturated compounds having —CHO groups bound to acyclic carbon atoms containing hydroxy groups acyclic
-
- 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
- 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
-
- 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
- C11D2111/00—Cleaning compositions characterised by the objects to be cleaned; Cleaning compositions characterised by non-standard cleaning or washing processes
- C11D2111/10—Objects to be cleaned
- C11D2111/12—Soft surfaces, e.g. textile
Landscapes
- Chemical & Material Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Veterinary Medicine (AREA)
- Animal Behavior & Ethology (AREA)
- General Health & Medical Sciences (AREA)
- Public Health (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Engineering & Computer Science (AREA)
- Oil, Petroleum & Natural Gas (AREA)
- Wood Science & Technology (AREA)
- Emergency Medicine (AREA)
- Epidemiology (AREA)
- Birds (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Fats And Perfumes (AREA)
- Cosmetics (AREA)
Abstract
本发明涉及新颖化合物及其作为香味材料的用途。
Description
相关申请状态
本申请要求于2019年11月27日提交的美国临时专利申请号62/940,967的优先权，将该临时专利申请的内容通过援引以其整体并入本文。
背景技术
在香味工业中持续需要提供新的化学品，以赋予调香师为香水、古龙水和个人护理产品创造新的香味的能力。本领域技术人员理解分子化学结构中的细微差异可以如何导致在气味、香调(note)和分子特征上的显著差异。这些变化以及在新香味开发中发现和使用新化学品的持续需要使调香师应用新化合物来创造新的香味。
发明内容
本发明提供了新颖化合物及其在增强、改善或改性香水、古龙水、花露水、织物护理产品、个人产品等的香味中的意想不到的有利用途。
更具体地，本发明涉及由以下列出的式I表示的新颖羟基-4,8-二甲基-癸-4-烯醛化合物：
其中R是C1-C3直链或支链的亚烷基。
本发明的另一个实施例涉及由以下列出的式II表示的上述羟基-4,8-二甲基-癸-4-烯醛化合物的子类别：
其中R’是C2或C3直链或支链的亚烷基。
本发明的其他实施例涉及一种香味配制品或香味产品，其包含提供的新颖化合物。
本发明的另一个实施例涉及一种改善、增强或改性香味配制品的方法，该方法包含将嗅觉可接受量的以上提供的新颖化合物添加到该香味配制品的步骤。
通过阅读以下说明，本发明的这些和其他实施例将是显而易见的。
具体实施方式
例如，通过表1中呈现的以下化合物来说明本发明的由式I和II表示的羟基-4,8-二甲基-癸-4-烯醛化合物。
表1
本领域技术人员将认识到，取决于可用的起始材料，本发明的化合物可能具有多种异构体，诸如位置异构体。本文的目的是本文描述的化合物包括异构体混合物以及可以使用本领域技术人员已知的技术分离的单一异构体。合适的技术包括色谱法，诸如高效液相色谱法(被称为HPLC)、以及特别是硅胶色谱法和被称为GC捕集的气相色谱法捕集。然而，商业产品大多以异构体混合物提供。
实例中详述了本发明化合物的制备和分离。除非另行说明，否则材料购自西格玛奥德里奇公司(Sigma-Aldrich Corporation)。
本发明的化合物展现了出人意料地且意想不到地强烈且持久的花香(floral)、甜美多汁(sweetjuicy)、青草香(green)以及水生铃兰(watery lily ofthe valley)的香调。本发明的化合物的用途广泛适用于目前的加香产品，包括香水与古龙水的制备、个人护理产品(诸如香皂、沐浴露、和头发护理产品)、织物护理产品、空气清新剂、以及化妆品制剂的加香。本发明还可用于加香清洁剂，诸如但不限于洗涤剂、洗碗材料、擦洗组合物(scrubbing composition)、窗户清洁物等。
在这些制剂中，本发明的化合物可以单独使用或与其他加香组合物、溶剂、辅助剂等组合使用。也可使用的其他成分的性质与种类是本领域技术人员已知的。许多类型的香味材料可以在本发明中使用，唯一的限制是与所使用的其他组分的相容性。合适的香味材料包括但不限于水果诸如杏仁、苹果、樱桃、葡萄、梨、菠萝、橙子、草莓、树莓；麝香；花香诸如类薰衣草、类玫瑰、类鸢尾、类康乃馨。其他令人愉悦的气味包括衍生自松树、云杉和其他林木气味的草本和林地气味。香味材料还可以衍生自各种油(诸如精油)或衍生自植物材料(诸如薄荷、留兰香等)。
US 4,534,891中提供了一系列合适的香味材料，该文件的内容通过援引如所陈述地以其整体并入。合适的香味材料的另一个来源见于W.A.Poucher于1959年编辑的Perfumes,Cosmetics andSoaps[香水，化妆品和香皂]，第二版中。在该专著中提供的香味材料之中有刺槐、金合欢、素心兰、仙客来、蕨、栀子、山楂、天芥菜、金银花、风信子、茉莉、丁香、百合、木兰、含羞草、水仙、鲜切的干草、橙花、兰花、木犀草、香豌豆、三叶草、晚香玉、香草、紫罗兰、桂竹等。
术语“烷基”意指直链或支链的饱和一价烃，例如，甲基、乙基、丙基、2-丙基、丁基(包括所有异构体形式)、戊基(包括所有异构体形式)、己基(包括所有异构体形式)等。术语“烯基”意指含有至少一个碳-碳双键的直链或支链不饱和脂族烃。术语“亚烷基”是指二价烷基。实例包括-CH2-、-CH2CH2-、-CHCH3-、-CH2CH2CH2-、-CH2(CH3)CH2-、-CH2CH2CH2CH2-等。
如本文所使用的术语“缓冲剂”应被理解为意指但不限于乙酸盐缓冲物、烷基胺缓冲物、氨基乙醇缓冲物、铵缓冲物、精氨酸缓冲物、巴比妥酸盐缓冲物、硼酸盐缓冲物、碳酸盐缓冲物、柠檬酸盐缓冲物、乙二胺缓冲物、葡糖酸盐(葡糖酸内酯)缓冲物、谷氨酸盐缓冲物、甘氨酸缓冲物、甘氨酰基甘氨酸缓冲物、咪唑缓冲物、乳酸盐缓冲物、苹果酸盐缓冲物、磷酸盐缓冲物、吡啶缓冲物、酒石酸盐缓冲物、三羟甲基氨基甲烷缓冲物(tris buffer)、三乙醇胺缓冲物、及其混合物。本发明的缓冲剂保持香味配制品中从约5至约11的希望的pH。
本发明的化合物可以与互补的香味化合物组合使用。如本文所使用的术语“互补的香味化合物”定义为选自由以下组成的组的香味化合物：2-[(4-甲基苯基)亚甲基]-庚醛(Acalea)、异戊基氧基乙酸烯丙酯(烯丙基戊基乙醇酸酯)、4,4,10,10,11,12,12-七甲基-3-氧杂三环[7.3.0.0<2,6>]十二烷(AMBER XTREMETM)、(3,3-二甲基环己基)乙基乙基丙烷-1,3-二酸酯(Applelide)、(E/Z)-1-乙氧基-1-癸烯(Arctical)、2-乙基-4-(2,2,3-三甲基-3-环-戊烯-1-基)-2-丁烯-1-醇(Bacdanol)、2-甲基-3-[(1,7,7-三甲基双环[2.2.1]庚-2-基)氧基]外-1-丙醇(以商品名
出售)、1,2,3,5,6,7-六氢-1,1,2,3,3-五甲基-4H-茚-4-酮(以商品名
出售)、三甲基环戊烯基甲基氧杂二环辛烷(Cassiffix)、1,1-二甲氧基-3,7-二甲基-2,6-辛二烯(柠檬醛DMA)、3,7-二甲基-6-辛烯-1-醇(香茅醇(Citronellol))、3A,4,5,6,7,7A-六氢-4,7-桥亚甲基-1H-茚-5/6-基乙酸酯(以商品名
出售)、3A,4,5,6,7,7A-六氢-4,7-桥亚甲基-1H-茚-5/6-基丙酸酯(以商品名
出售)、3A,4,5,6,7,7A-六氢-4,7-桥亚甲基-1G-茚-5/6-基丁酸酯(Cyclobutanate)、1-(2,6,6-三甲基-3-环己烯-1-基)-2-丁烯-1-酮(DeltaDamascene)、3-(4-乙基苯基)-2,2-二甲基丙腈(Fleuranil)、3-(O/P-乙基苯基)2,2-二甲基丙醛(海风醛(Floralozone))、四氢-4-甲基-2-(2-甲基丙基)-2H-吡喃-4-醇(Floriffol)、1,3,4,6,7,8-六氢-4,6,6,7,8,8-六甲基环戊-γ-2-苯并吡喃(加乐麝香(Galaxolide))、1-(5,5-二甲基-1-环己烯-1-基)戊-4-烯-1-酮(Galbascone)、E/Z-3,7-二甲基-2,6-辛二烯-1-基乙酸酯(乙酸香叶酯(Geranyl Acetate))、α-甲基-1,3-苯并二氧杂环戊二烯-5-丙醛(以商品名
出售)、1-(2,6,6-三甲基-2-环己烯-1-基)-1,6-庚二烯-3-酮(Hexalon)、(Z)-3-己烯基-2-羟基苯甲酸酯(水杨酸顺式-3-己烯酯(Hexenyl Salicylate,CIS-3))、4-(2,6,6-三甲基-2-环己烯-1-基)-3-丁烯-2-酮(α-紫罗兰酮(Iononeα))、1-(1,2,3,4,5,6,7,8-八氢-2,3,8,8-四甲基-2-萘基)-乙-1-酮(以商品名ISO E
出售)、3-氧代-2-戊基环戊烷乙酸甲酯(Kharismal)、2,2,4-三甲基-4-苯基-丁腈(Khusinil)、3,4,5,6,6-五甲基庚-3-烯-2-酮(以商品名
出售)、3/4-(4-羟基-4-甲基-戊基)环己烯-1-甲醛(Lyral)、3-甲基-4-(2,6,6-三甲基-2-环己烯-1-基)-3-丁烯-2-酮(γ-甲基紫罗兰酮(Methyl Iononeγ))、1-(2,6,6-三甲基-2-环己烯-1-基)戊-1-烯-3-酮(α-甲基紫罗兰酮额外(Methyl IononeαExtra)、甲基紫罗兰酮N(MethylIonone N))、3-甲基-4-苯基丁-2-醇(Muguesia)、环十五碳-4-烯-1-酮(Musk Z4)、3,3,4,5,5-五甲基-11,13-二氧杂三环[7.4.0.0<2,6>]十三碳-2(6)-烯(以商品名
出售)、3,7-二甲基-2,6-辛二烯-1-基乙酸酯(橙花醇乙酸酯(NerylAcetate))、3,7-二甲基-1,3,6-辛三烯(罗勒烯(Ocimene))、邻甲苯基乙醇(Peomosa)、3-甲基-5-苯基戊醇(Phenoxanol)、1-甲基-4-(4-甲基-3-戊烯基)环己-3-烯-1-甲醛(Precyclemone B)、4-甲基-8-亚甲基-2-金刚烷醇(Prismantol)、2-乙基-4-(2,2,3-三甲基-3-环戊烯-1-基)-2-丁烯-1-醇(Sanjinol)、2-甲基-4-(2,2,3-三甲基-3-环戊烯-1-基)-2-丁烯-1-醇(Santaliff)、3-[顺式-4-(2-甲基丙基)环己基]丙醛(Starfleur.)、萜品醇、2,4-二甲基-3-环己烯-1-甲醛(以商品名
出售)、十氢-2,6,6,7,8,8-六甲基-2H-茚并[4,5-B]呋喃(Trisamber)、乙酸2-叔丁基环己基酯(Verdox)、(3E)-4-甲基癸-3-烯-5-酮(Veridian)、乙酸4-叔丁基环己基酯(Vertenex)、乙酰基柏木烯(Vertofix)、3,6/4,6-二甲基环己-3-烯-1-甲醛(Vertoliff)和(3Z)-1-[(2-甲基-2-丙烯基)氧基]-3-己烯(Vivaldie)。
术语“香味配制品(fragrance formulation)”、“香味组合物(fragrancecomposition)”、“加香配制品(perfume formulation)”和“加香组合物(perfumecomposition)”含义相同并且是指包括例如醇、醛、酮、酯、醚、内酯、腈、天然油、合成油、和硫醇的化合物的混合物的消费组合物(consumer composition)，将这些化合物混合使得单个组分的组合气味产生令人愉悦或希望的香味。本发明的香味配制品是包含本发明的化合物的消费组合物。进一步地，本发明的香味配制品包含本发明的化合物和如上定义的互补的香味化合物。还进一步地，本发明的香味配制品包含本发明的化合物和如上定义的缓冲剂。
术语“香味产品”意指含有增加香味或掩蔽恶臭的香味成分的消费产品。香味产品可包括例如香水；古龙水；花露水；个人护理产品；清洁产品；条皂；液体皂；沐浴露；泡泡浴液(foam bath)；化妆品制剂；皮肤护理产品诸如霜剂、洗剂和剃须产品；用于洗发、漂洗、调理、漂白、着色、染色和造型的头发护理产品；除臭剂和止汗剂；女性护理产品诸如卫生棉条和女性卫生巾；婴儿护理产品诸如尿布、围嘴和擦拭物；家庭护理产品诸如卫生纸(bathtissue)、化妆纸(facial tissue)、手帕纸(paper handkerchief)或擦手纸(papertowel)；织物产品诸如织物柔软剂和织物清新剂；空气护理产品诸如空气清新剂和香味递送系统；清洁剂和消毒剂诸如洗涤剂、洗碗材料、擦洗组合物、玻璃和金属清洁物(诸如窗户清洁物)、台面清洁物、地面和地毯清洁物、厕所清洁物和漂白添加剂；清洗剂诸如通用、重垢、和手洗或精细织物清洗剂(包括衣物洗涤剂和漂洗添加剂)；牙齿和口腔卫生产品诸如牙膏、牙凝胶、牙线、义齿清洁物、义齿胶粘剂、洁牙剂、牙齿增白剂和漱口剂；健康护理和营养产品以及食物产品诸如小吃和饮料产品。本发明的香味产品是含有本发明的化合物的消费产品。进一步地，本发明的香味产品含有本发明的化合物和如上定义的互补的香味化合物。还进一步地，本发明的香味产品包含本发明的化合物和如上定义的缓冲剂。
短语“改善、增强或改性香味配制品”中的术语“改善”应理解为意指将香味配制品提升至更希望的特征。术语“增强”应理解为意指使香味配制品的效果更好或为该香味配制品提供改善的特征。术语“改性”应理解为意指为香味配制品提供特征的变化。
术语“一个/种(a/an)”应理解为意指一个/种或多个/种。
术语“嗅觉可接受量”应理解为意指香味配制品中化合物的量，其中化合物将贡献其独特的嗅觉特征。然而，香味配制品的嗅觉效果将是香味成分各自效果的总和。因此，本发明的化合物可用于改善或增强香味配制品的芳香特征，或用于改性该配制品中其他成分所贡献的嗅觉反应。该嗅觉可接受量可以取决于许多因素(包括其他成分、它们的相对量和希望的嗅觉效果)而改变。
香味配制品中使用的本发明的化合物的量从约10-8至约70重量百分比、优选地从约10-6至约50重量百分比、更优选地从约10-4至约25重量百分比、并且甚至更优选地从约0.01至约10重量百分比变化。本领域技术人员将能够使用希望量以提供希望的香味效果和强度。除了本发明的化合物之外，其他材料也可以与香味配制品结合使用以包封和/或递送香味。一些众所周知的材料是例如但不限于聚合物；低聚物；其他非聚合物诸如表面活性剂、乳化剂；脂质包括脂肪、蜡和磷脂质；有机油；矿物油；矿脂；天然油；固香剂(perfumefixative)；纤维；淀粉；糖和固体表面材料诸如沸石和二氧化硅。一些优选的聚合物包括聚丙烯酸酯、聚脲、聚氨酯、聚丙烯酰胺、聚酯、聚醚、聚酰胺、聚(丙烯酸酯-共-丙烯酰胺)、淀粉、二氧化硅、明胶和阿拉伯树胶、藻酸盐、壳聚糖、聚交酯、聚(三聚氰胺-甲醛)、聚(脲-甲醛)、或其组合。
当在香味配制品中使用时，这些成分提供额外的香调，以使得香味配制品更合意和引人注意，并增加了感知价值。在这些材料中发现的气味品质有助于美化和增强成品一致性，以及改善该香味中其他材料的性能。
此外，还令人惊讶地发现本发明的化合物提供优越的成分性能、以及在恶臭冲消(malodor counteracting)应用诸如身体汗液、环境气味(诸如黑霉(mold)和白霉(mildew))、浴室等中具有意想不到的优点。本发明的化合物基本上消除了恶臭的感知和/或防止这样的恶臭形成，因此可以与众多的功能性产品一起使用。
本文提供功能性产品的实例以说明本发明的各个方面。但是，它们不旨在限制本发明的范围。功能性产品可以包括例如常规的房间清新剂(或除臭剂)组合物，诸如房间清新剂喷雾剂、气雾剂或其他喷雾剂；香味扩散剂、芯或其他液体系统、或固体，例如香盒和塑料中的蜡烛或蜡碱、香囊或干喷雾剂中的粉末或如在固体凝胶棒中的凝胶；如通过洗衣机应用所应用的衣物除臭剂，诸如应用于洗涤剂、粉末、液体、增白剂或织物柔软剂、织物清新剂、亚麻喷雾剂、壁橱区(closetblock)、壁橱气雾喷雾剂(closet aerosol spray)、或衣物存储区域中或干洗中以克服衣物上残留的溶剂香调；浴室配件诸如擦手纸、卫生纸、卫生巾、湿巾、一次性洗布、一次性尿布和尿布桶除臭剂；清洁物诸如消毒剂和抽水马桶清洁物；化妆品产品诸如止汗剂和除臭剂；呈粉末、气雾、液体或固体形式的一般身体除臭剂；或头发护理产品诸如发胶、调理剂、漂洗剂、头发着色剂和染色剂、烫发剂、脱毛剂、直发剂；理发应用(hair groom application)诸如润发油、霜剂和洗剂；含有成分诸如二硫化硒、煤焦油或水杨酸盐的含药头发护理产品、或洗发剂；或足部护理产品诸如爽足粉、液体或古龙水；须后水和身体乳液；或香皂和合成洗涤剂诸如皂条、液体、泡沫或粉末；气味控制诸如在制造过程期间(诸如纺织整理业和印刷业(油墨和纸))；流出物控制诸如在涉及制浆、畜牧场和肉类处理的工艺中；污水处理；垃圾袋或垃圾处置；或者在产品气味控制中，如在纺织制成品、橡胶制成品或汽车空气清新剂中；农业和宠物护理产品，诸如狗和鸡舍流出物以及家畜和宠物护理产品诸如除臭剂、洗发剂或清洁剂，或动物卫生砂材料；以及在大规模封闭式空气系统诸如礼堂、和地铁以及运输系统中。
因此，可以看到本发明的配制品通常是其中恶臭冲消剂与载体一起存在的配制品，凭借该载体或从该载体可以将该恶臭冲消剂引入到其中存在恶臭的空气空间内，或引入到其上沉积有恶臭的基底。例如，载体可以是气雾推进剂诸如氯氟甲烷，或固体诸如蜡、塑料材料、橡胶、惰性粉末或凝胶。在芯型空气清新剂中，载体是低挥发性的基本上无味的液体。在若干应用中，本发明的配制品含有表面活性剂或消毒剂，而在其他应用中，恶臭冲消剂存在于纤维基底上。在本发明的许多配制品中也存在香味组分，其赋予配制品香味。上述香味材料全部可以使用。
恶臭冲消有效量应理解为意指功能性产品中使用的本发明的恶臭冲消剂减弱给定的恶臭的同时降低气味水平的组合强度的感官有效的量，其中给定的恶臭是存在于空气空间中或已沉积于基底上。所使用的恶臭冲消剂的确切量可以取决于恶臭冲消剂的类型、所使用的载体类型、和所希望的恶臭冲消能力的水平而变化。一般来说，存在的恶臭冲消剂的量是获得希望结果所需要的普通剂量。这样的剂量是本领域技术人员已知的。在优选的实施例中，当与恶臭固体或液体功能性产品例如香皂和洗涤剂结合使用时，本发明的化合物可以以范围从约0.005至约50重量百分比、优选地从约0.01至约20重量百分比、并且更优选地从约0.05至约5重量百分比的量存在，并且当与恶臭的气态功能性产品结合使用时，本发明的化合物可以以范围从约0.1至10mg/立方米空气的量存在。
作为本发明的具体实施例提供以下内容。本发明的其他修改对本领域技术人员将是显而易见的。此类修改应理解为在本发明的范围内。除非另行说明，否则本文所使用的所有百分比是重量百分比，ppm应理解为代表每百万份的份数，L应理解为升，mL应解为毫升，g应理解为克，Kg应理解为千克，mol应理解为摩尔，mmol应理解为毫摩尔，psi应理解为每平方英寸的磅力，并且mmHg应理解为汞(Hg)的毫米数(mm)。如实例中使用的IFF应理解为意指美国纽约州纽约市的国际香精香料公司(International Flavors&Fragrances Inc.)。
实例I：5-(3,3-二甲基环氧乙烷-2-基)3-甲基戊-1-醇(结构1a)的制备
将3,7-二甲基辛-6-烯-1-醇(655g、3.98mol)和碳酸钠(Na2CO3)(150g、1.41mol)的混合物在甲苯(2L)中搅拌并使用冰浴冷却至15℃。在3小时内向该混合物添加过乙酸(CH3COOOH)(乙酸中32％)(994g、4.18mol)同时将温度保持在20℃-25℃。在进料完成后，将反应在25℃下老化另外3小时。使用碳酸钠溶液(10％)(1L)、亚硫酸钠溶液(Na2SO3)(10％)(1L)和盐水溶液(NaCl)(1L)依次洗涤反应混合物以提供粗反应混合物。
实例II：3,7-二甲基辛-7-烯-1,6-二醇(结构1b)的制备
将来自实例I的粗反应混合物装入含有甲苯(1L)的3-L反应烧瓶(装有迪安-斯塔克分水器(Dean-Starktrap))并加热至120℃。将残留的水去除并将反应混合物冷却至室温。添加异丙醇铝(Al(O-i-Pr)3)(70g、0.34mol)并将反应混合物加热至回流(125℃)持续10小时。然后用氢氧化钠溶液(NaOH)(15％)(1.35Kg)将反应混合物淬灭，用氢氧化钠溶液(10％)(1.2Kg)随后用盐水溶液(1L)洗涤。将得到的混合物蒸馏以提供呈透明油状物的、在1mmHg下具有152℃沸点的3,7-二甲基辛-7-烯-1,6-二醇(679g)。
1H NMR(500MHz,CDCl3)δ:4.87(br s,1H),4.77(br s,1H),3.93-4.00(m,1H),3.51-3.68(m,2H),2.75(br s,2H),1.66(s,3H),0.96-1.59(m,7H),0.85(d,J＝6.6Hz,3H)。
实例III：10-羟基-4,8-二甲基癸-4-烯醛(结构1)的制备
将3,7-二甲基辛-7-烯-1,6-二醇(100g、0.58mol)(实例II中获得)置于含有乙基乙烯基醚(CH3CH2OCH＝CH2)(209g、2.9mol)和苯基膦酸(C6H5-PO(OH)2)(1.1g、0.007mol)的1-L高压釜中。将高压釜加热至130℃持续2小时，并且然后加热至150℃持续另外的6小时。通过添加己烷(100mL)对反应混合物进行后处理，并且然后用碳酸氢钠溶液(NaHCO3)(200mL)随后用盐水溶液(200mL)洗涤。将获得的粗产物蒸馏以提供含有(E)-和(Z)-异构体二者、并且在2mmHg下具有195℃的沸点的10-羟基-4,8-二甲基癸-4-烯醛(60g)。
(E)-10-羟基-4,8-二甲基癸-4-烯醛具有以下NMR谱特征：1H NMR(500MHz,CDCl3)δ:9.75(t,J＝2.05Hz,1H),5.15(m,1H),3.67(m,2H),2.52(m,2H),2.33(m,2H),2.00(m,2H),1.62(s,3H),1.58(m,1H),1.37(m,2H),1.21(m,2H),0.91(d,J＝6.6Hz,3H)。
(Z)-10-羟基-4,8-二甲基癸-4-烯醛具有以下NMR谱特征：1H NMR(500MHz,CDCl3)δ:9.78(t,J＝1.93Hz,1H),5.14(m,1H),3.68(m,2H),2.52(m,2H),2.33(m,2H),2.00(m,2H),1.68(s,3H),1.58(m,1H),1.14-1.43(m,4H),0.91(d,J＝6.6Hz,3H)。
实例IV：10,10-二甲氧基-3,7-二甲基癸-1,6-二烯的制备
将4,8-二甲基癸-4,9-二烯醛(600g、3.3mol)、原甲酸三甲酯(CH(OCH3)3)(530g、5.0mol)和甲醇(60mL)的混合物装入配备有机械搅拌器、冷凝器和热电偶的3-L圆底烧瓶。将反应混合物冷却至0℃-10℃并且一次性添加盐酸溶液(37％)(3g、0.03mol)。使反应混合物放热至20℃-30℃并老化1小时。在反应完成后(其通过气相色谱仪样品证实)，用甲醇钠溶液(25％)(20g、0.09mol)将反应混合物淬灭，并用盐水溶液(500mL)洗涤。将得到的混合物蒸馏以提供在8mmHg下具有138℃沸点的10,10-二甲氧基-3,7-二甲基癸-1,6-二烯(655g)。
1H NMR(400MHz,CDCl3)δ:5.68(ddd,J＝17.3,10.1,7.5Hz,1H),5.10-5.17(m,1H),4.86-5.01(m,2H),4.29-4.38(m,1H),3.31(s,6H),1.88-2.23(m,5H),1.63-1.75(m,2H),1.59(s,3H),1.23-1.40(m,2H),0.98(d,J＝6.8Hz,3H)。
实例V：11,11-二甲氧基-4,8-二甲基十一碳-7-烯醛的制备
将10,10-二甲氧基-3,7-二甲基癸-1,6-二烯(1.31Kg、5.8mol)(实例IV中获得)、羰基氢化三(三苯基膦)铑(I)([RhH(CO)(PPh3)3])(在庄信万丰公司(Johnson MattheyInc.)可商购)(4.5g、0.0049mol)、碳酸氢钠(1.5g、0.018mol)和甲苯(300mL)的混合物装入4-L高压釜，加热至100℃并用合成气(1:1的H2:CO比率)加压至400psi。使反应混合物老化8小时。得到的11,11-二甲氧基-4,8-二甲基十一碳-7-烯醛粗产物在下个步骤中直接使用。
1H NMR(500MHz,CDCl3)δ:9.70(t,J＝1.9Hz,约90％的1H),9.55-9.63(m,10％的1H),5.00-5.12(m,1H),4.27(t,J＝5.7Hz,1H),3.18-3.35(m,6H),2.21-2.45(m,2H),1.83-2.06(m,4H),1.50-1.70(m,6H),1.34-1.46(m,2H),1.23-1.34(m,1H),1.08-1.22(m,1H),0.75-1.01(m,3H)。
实例VI：11,11-二甲氧基-4,8-二甲基十一碳-7-烯-1-醇的制备
将硼氢化钠(NaBH4)(20.5g、0.54mol)和异丙醇(CH3CHOHCH3)(800mL)装入配备有加料漏斗、机械搅拌器、冷凝器和热电偶的3-L圆底烧瓶。将混合物加热到70℃并且在2小时内在70℃-75℃下进料11,11-二甲氧基-4,8-二甲基十一碳-7-烯醛(612g、1.56mol)(实例V中获得)。使反应混合物在80℃下老化1小时。在反应完成后(其通过气相色谱仪样品证实)，将反应混合物冷却，用水淬灭，并且用氢氧化钠溶液(10％)(500mL)洗涤、随后用盐水溶液(500mL)洗涤两次。将粗产物蒸馏以提供在6mmHg下具有163℃沸点的11,11-二甲氧基-4,8-二甲基十一碳-7-烯-1-醇(404g)。
1H NMR(500MHz,CDCl3)δ:5.09(t,J＝6.6Hz,1H),4.29(t,J＝5.8Hz,1H),3.50-3.61(m,2H),3.27(s,6H),1.83-2.05(m,4H),1.59-1.71(m,2H),1.56(s,3H),1.42-1.56(m,2H),1.24-1.41(m,3H),1.01-1.23(m,2H),0.84(d,J＝6.6Hz,3H)。
实例VII：11-羟基-4,8-二甲基十一碳-4-烯醛(结构2)的制备
将11,11-二甲氧基-4,8-二甲基十一碳-7(E/Z)-烯-1-醇(260g、1.0mol)(实例VI中获得)、三氟乙酸(CF3CO2H)(14g、0.12mol)(在阿法埃莎公司(Alfa Aesar)可商购)、2-丁酮(CH3C(O)CH2CH3)(650g、9.0mol)和水(36g、2mol)的混合物装入配备有机械搅拌器、冷凝器和热电偶的2-L圆底烧瓶、并且加热以在73℃下温和回流并老化8小时。然后将反应混合物冷却，用水(200mL)淬灭，并且用碳酸氢钠溶液(3％)(200mL)洗涤。使用转膜蒸发(WipedFilm Evaporation)在160℃的柱温度、0.5mmHg下以75g/小时的进料速率纯化得到的混合物，以提供11-羟基-4,8-二甲基十一碳-4-烯醛(155g)。
1H NMR(400MHz,CDCl3)δ:9.60-9.90(m,1H),5.03-5.30(m,1H),4.52-4.60(m,4％的1H),4.35(t,J＝5.7Hz,13％的1H),3.63(t,J＝6.7Hz,2H),3.30-3.33(m,13％的6H),2.45-2.57(m,2H),2.27-2.41(m,2H),1.88-2.15(m,2H),1.62(s,3H),1.26-1.62(m,5H),1.08-1.24(m,2H),0.89(d,J＝6.4Hz,3H)。
实例VIII：12,12-二甲氧基-5,9-二甲基十二碳-8-烯-2-醇的制备
将在四氢呋喃中的甲基氯化镁溶液(CH3MgCl)(3M)(800mL、2.4mol)装入配备有加料漏斗、机械搅拌器、冷凝器和热电偶的火焰干燥的3-L圆底烧瓶，并且冷却至10℃。在3小时内在10℃-15℃下进料11,11-二甲氧基-4,8-二甲基十一碳-7-烯醛(852g、2.16mol)(实例V中获得)。使反应混合物在20℃下老化1小时。在反应完成后(其通过气相色谱仪样品证实)，用含有乙酸(150g、2.5mol)的冰(1L)将反应混合物淬灭，用盐水溶液(600mL)随后用碳酸钠溶液(4％)(400mL)洗涤。将得到的混合物蒸馏以提供在2mmHg下具有166℃沸点的12,12-二甲氧基-5,9-二甲基十二碳-8-烯-2-醇(620g)。
1H NMR(500MHz,CDCl3)δ：5.06-5.13(m,1H),4.30(t,J-5.7Hz,1H),3.61-3.81(m,1H),3.27(s,6H),1.85-2.07(m,4H),1.60-1.71(m,2H),1.56(s,3H),1.00-1.50(m,7H),1.14(d,J＝6.2Hz,3H),0.80-0.88(m,3H)。
实例IX：11-羟基-4,8-二甲基十二碳-4-烯醛(结构3)的制备
将12,12-二甲氧基-5,9-二甲基十二碳-8-烯-2-醇(400g、1.4mol)(实例VIII中获得)、三氟乙酸(20g、0.175mol)、2-丁酮(1Kg、13.9mol)和水(50g、2.8mol)的混合物装入配备有机械搅拌器、冷凝器和热电偶的2-L圆底烧瓶、并且加热以在73℃下温和回流并老化8小时。然后将反应混合物冷却，用水(300mL)淬灭，并且用碳酸氢钠溶液(3％)(300mL)洗涤。使用转膜蒸发(Wiped Film Evaporation)在160℃的柱温度、0.5mmHg下以75g/小时的进料速率纯化得到的混合物，以提供11-羟基-4,8-二甲基十二碳-4-烯醛(316g)。
1H NMR(500MHz,CDCl3)δ：9.61-9.76(m,1H),5.00-5.18(m,1H),4.53-4.62(m,3％的1H),4.27(t,J＝5.7Hz,1％的1H),3.58-3.79(m,1H),3.23-3.27(m,1％的6H),2.37-2.51(m,2H),2.19-2.34(m,2H),1.79-2.00(m,2H),1.55(s,3H),0.97-1.50(m,7H),1.11(d,J＝6.2Hz,3H),0.75-0.86(m,3H)。
实例X：香味评价
对具有不同浓度(10-4％、10-3％、10-2％、0.1％和1％)的上述化合物在不同pH值(2、4、5、6、7、8、9、10、11和12)下的香味特性进行评价，其中使用柠檬酸钠(或钾)、葡糖酸钠(或钾)、乳酸钠(或钾)、柠檬酸、柠檬酸单钠、葡糖酸、葡糖酸内酯或乳酸缓冲物对pH进行调节。在不同pH值下的气味概况报告在表2中。
表2
如上所示，结构1-3在5-11的pH范围内展现了希望的花香和青草香香调。当pH值低于5或高于11时出现异常香调。在具体pH范围内这样的气味概况和有利的特性是意想不到的。
实例XI：类似物
此外，制备了以下类似物。
10-羟基-4,8-二甲基癸醛(结构A)的制备。通过选择性氢化从结构1(实例I-III中获得)制备10-羟基-4,8-二甲基癸醛。
1H NMR(500MHz,CDCl3)δ:9.74(t,J＝1.9Hz,1H),3.58-3.69(m,2H),2.33-2.46(m,2H),1.47-1.76(m,3H),1.15-1.46(m,7H),1.01-1.15(m,2H),0.80-0.90(m,6H)。
9-羟基-3,7-二甲基壬醛(结构B)的制备。通过组合了酯化、热裂解、碱水解和加氢甲酰化的多步骤合成从3,7-二甲基辛烷-1,7-二醇制备9-羟基-3,7-二甲基壬醛。
1H NMR(400MHz,CDCl3)δ:9.71(t,J＝2.2Hz,1H),4.57-4.67(m,8％的1H),3.55-3.70(m,2H),2.30-2.41(m,1H),2.15-2.25(m,1H),1.97-2.07(m,1H),1.48-1.61(m,2H),1.02-1.39(m,8H),0.92(d,J＝6.6Hz,3H),0.85(d,J＝6.6Hz,3H)。
9-羟基-2,5,9-三甲基癸-2-烯醛(结构C)的制备。通过羟醛缩合从羟基香茅醛(在巴斯夫公司(BASF)可商购)制备9-羟基-2,5,9-三甲基癸-2-烯醛。
1H NMR(500MHz,CDCl3)δ:9.31(s,1H),6.42-6.47(m,1H),2.23-2.31(m,1H),2.08-2.18(m,1H),1.65(s,3H),1.57-1.67(m,1H),1.23-1.40(m,5H),1.13(s,6H),1.09-1.20(m,1H),0.86(d,J＝6.6Hz,3H)。
9-羟基-2,5,9-三甲基癸醛(结构D)的制备。通过羟醛缩合随后选择性氢化从羟基香茅醛(在巴斯夫公司可商购)制备9-羟基-2,5,9-三甲基癸醛。
1H NMR(500MHz,CDCl3)δ:9.56-9.58(m,1H),2.17-2.36(m,1H),1.58-1.75(m,1H),1.21-1.42(m,8H),1.17(s,6H),1.07-1.15(m,2H),1.02-1.06(m,3H),0.82-0.86(m,3H)。
11-羟基-4,8-二甲基十一醛(结构E)的制备。通过选择性氢化从结构2(实例IV-VII中获得)制备11-羟基-4,8-二甲基十一醛。
1H NMR(400MHz,CDCl3)δ:9.77(t,J＝1.9Hz,1H),3.63(t,J＝6.7Hz,2H),2.34-2.51(m,2H),1.49-1.78(m,3H),1.21-1.49(m,8H),(m,3H),0.84-0.96(m,6H)。
11-羟基-4,8-二甲基十二醛(结构F)的制备。通过选择性氢化从结构3(实例IV、V、VIII和IX中获得)制备11-羟基-4,8-二甲基十二醛。
1H NMR(600MHz,CDCl3)δ：9.77(t,J＝1.9Hz,1H),3.71-3.81(m,1H),2.37-2.48(m,2H),1.62-1.72(m,1H),1.21-1.54(m,10H),1.16-1.20(m,3H),1.04-1.16(m,3H),0.83-0.91(m,6H)。
10-羟基-4,8-二甲基十一醛(结构G)的制备。通过组合了甲基格氏反应(methylGrignard reaction)、用过乙酸的环氧化反应、环氧化重排为烯丙醇、以及用丁基乙烯基醚的克莱森重排(Claisen rearrangement)的多步骤合成从香茅醛制备10-羟基-4,8-二甲基十一醛。
1H NMR(500MHz,CDCl3)δ:9.68-9.78(m,1H),3.82-3.89(m,1H),2.33-2.45(m,2H),1.47-1.67(m,2H),0.99-1.47(m,13H),0.78-0.92(m,6H)。
11-甲氧基-4,8-二甲基十一碳-4-烯醛(结构H)的制备。通过组合了初始保护步骤以形成环状缩醛、随后的氢化并转化为甲基醚、以及最后的脱保护步骤的多步骤合成从结构2(实例IV-VII中获得)制备11-甲氧基-4,8-二甲基十一碳-4-烯醛。
1H NMR(500MHz,CDCl3)δ:9.73-9.76(m,1H),5.11-5.17(m,1H),3.34(t,J＝6.9Hz,2H),3.32(s,3H),2.45-2.54(m,2H),2.26-2.36(m,2H),1.84-2.17(m,2H),1.45-1.77(m,5H),1.22-1.44(m,3H),1.03-1.21(m,2H),0.81-0.93(m,3H)。
11-甲氧基-4,8-二甲基十一醛(结构I)的制备。通过组合了初始保护步骤以形成环状缩醛、随后的氢化并转化为甲基醚、以及最后的脱保护步骤的多步骤合成从结构2(实例IV-VII中获得)制备11-甲氧基-4,8-二甲基十一醛。
1H NMR(500MHz,CDCl3)δ:9.75(t,J＝1.9Hz,1H),3.33(t,J＝6.6Hz,2H),3.31(s,3H),2.33-2.46(m,2H),1.47-1.71(m,3H),1.17-1.46(m,8H),1.00-1.17(m,3H),0.81-0.89(m,6H)。
当与结构A-I比较时，结构1-3展现了结构A-I中缺少的独特和高度希望的花香、甜美、多汁、青草香和铃兰香调。而且，这样的香调强烈且持久。这样的有利特性是意想不到的。
Claims (18)
1.一种香味配制品，其包含嗅觉可接受量的具有式I的化合物：
和缓冲剂，其中R是C1-C3直链或支链的亚烷基，并且其中该香味配制品具有从5至11的pH范围。
2.如权利要求1所述的香味配制品，其中，该化合物由式II表示：
其中R’是C2或C3直链或支链的亚烷基。
3.如权利要求1所述的香味配制品，其中，该化合物选自由以下组成的组：
10-羟基-4,8-二甲基癸-4-烯醛；
11-羟基-4,8-二甲基十一碳-4-烯醛；
11-羟基-4,8-二甲基十二碳-4-烯醛；
10-羟基-4,8-二甲基十一碳-4-烯醛；以及
其混合物。
4.如权利要求1所述的香味配制品，其中，该嗅觉可接受量是该香味配制品的从约10-6至约50重量百分比。
5.如权利要求1所述的香味配制品，其中，该嗅觉可接受量是该香味配制品的从约10-4至约25重量百分比。
6.如权利要求1所述的香味配制品，其中，该嗅觉可接受量是该香味配制品的从约0.01至约10重量百分比。
7.如权利要求1所述的香味配制品，其进一步包含聚合物。
8.如权利要求7所述的香味配制品，其中，该聚合物选自由以下组成的组：聚丙烯酸酯、聚脲、聚氨酯、聚丙烯酰胺、聚酯、聚醚、聚酰胺、聚(丙烯酸酯-共-丙烯酰胺)、淀粉、二氧化硅、明胶和阿拉伯树胶、藻酸盐、壳聚糖、聚交酯、聚(三聚氰胺-甲醛)、聚(脲-甲醛)及其组合。
9.如权利要求1所述的香味配制品，其中，该缓冲剂选自由以下组成的组：乙酸盐缓冲物、烷基胺缓冲物、氨基乙醇缓冲物、铵缓冲物、精氨酸缓冲物、巴比妥酸盐缓冲物、硼酸盐缓冲物、碳酸盐缓冲物、柠檬酸盐缓冲物、乙二胺缓冲物、葡糖酸盐(葡糖酸内酯)缓冲物、谷氨酸盐缓冲物、甘氨酸缓冲物、甘氨酰基甘氨酸缓冲物、咪唑缓冲物、乳酸盐缓冲物、苹果酸盐缓冲物、磷酸盐缓冲物、吡啶缓冲物、酒石酸盐缓冲物、三羟甲基氨基甲烷缓冲物、三乙醇胺缓冲物、及其混合物。
10.一种改善、增强或改性香味配制品的方法，该方法包括将嗅觉可接受量的具有式I的化合物：
和缓冲剂添加到该香味配制品中的步骤，其中R是C1-C3直链或支链的亚烷基，并且其中该香味配制品具有从5至11的pH范围。
11.如权利要求10所述的方法，其中，该化合物由式II表示：
其中R’是C2或C3直链或支链的亚烷基。
12.如权利要求10所述的方法，其中该化合物选自由以下组成的组：
10-羟基-4,8-二甲基癸-4-烯醛；
11-羟基-4,8-二甲基十一碳-4-烯醛；
11-羟基-4,8-二甲基十二碳-4-烯醛；
10-羟基-4,8-二甲基十一碳-4-烯醛；以及其混合物。
13.一种香味产品，其含有如权利要求1所述的香味配制品。
14.如权利要求13所述的香味产品，其中，该香味产品选自由以下组成的组：香水、古龙水、花露水、个人护理产品、清洁产品、条皂、液体皂、沐浴露、泡泡浴液、化妆品制剂、皮肤护理产品、头发护理产品、除臭剂、止汗剂、女性护理产品、婴儿护理产品、家庭护理产品、织物产品、空气护理产品、香味递送系统、清洁剂、消毒剂、清洗剂、牙齿和口腔卫生产品、健康护理和营养产品以及食物产品。
15.如权利要求14所述的香味产品，其中，该清洁产品选自由以下组成的组：洗涤剂、洗碗材料、擦洗组合物、玻璃清洁物、金属清洁物、台面清洁物、地面清洁物、地毯清洁物、厕所清洁物和漂白添加剂。
16.如权利要求14所述的香味产品，其中，该清洗剂选自由衣物洗涤剂和漂洗添加剂组成的组。
17.一种具有式II的化合物：
其中R’是C2或C3直链或支链的亚烷基。
18.如权利要求17所述的化合物，其选自由以下组成的组：11-羟基-4,8-二甲基十一碳-4-烯醛；11-羟基-4,8-二甲基十二碳-4-烯醛；10-羟基-4,8-二甲基十一碳-4-烯醛；以及其混合物。
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| JPS5291815A (en) * | 1976-01-30 | 1977-08-02 | Taiyo Koryo Kk | Oxyaldehyde compound and its preparation |
| US20190183766A1 (en) * | 2012-12-19 | 2019-06-20 | Colgate-Palmolive Company | Dentifrice Comprising Zinc-Amino Acid Complex |
| CN105283435A (zh) * | 2013-06-10 | 2016-01-27 | 奇华顿股份有限公司 | 有机化合物中或与之相关的改进 |
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