JP5930347B2 - 賦香成分としての新規なアルデヒド - Google Patents
賦香成分としての新規なアルデヒド Download PDFInfo
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- JP5930347B2 JP5930347B2 JP2014547833A JP2014547833A JP5930347B2 JP 5930347 B2 JP5930347 B2 JP 5930347B2 JP 2014547833 A JP2014547833 A JP 2014547833A JP 2014547833 A JP2014547833 A JP 2014547833A JP 5930347 B2 JP5930347 B2 JP 5930347B2
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- JP
- Japan
- Prior art keywords
- perfume
- methyl
- methylene
- decadienal
- product
- 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.)
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- 239000003205 fragrance Substances 0.000 claims description 31
- 239000002304 perfume Substances 0.000 claims description 31
- 241000755716 Convallaria Species 0.000 claims description 10
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- 238000000034 method Methods 0.000 claims description 9
- 239000000463 material Substances 0.000 claims description 8
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- KXAIVACSXVMJTH-XYOKQWHBSA-N (4e)-4-methyl-8-methylidenedeca-4,9-dienal Chemical compound O=CCCC(/C)=C/CCC(=C)C=C KXAIVACSXVMJTH-XYOKQWHBSA-N 0.000 claims description 5
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- 239000001738 pogostemon cablin oil Substances 0.000 description 1
- 229920000642 polymer Polymers 0.000 description 1
- 229920002689 polyvinyl acetate Polymers 0.000 description 1
- 239000011118 polyvinyl acetate Substances 0.000 description 1
- 229920002451 polyvinyl alcohol Polymers 0.000 description 1
- 239000000843 powder Substances 0.000 description 1
- 230000002028 premature Effects 0.000 description 1
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 102000004169 proteins and genes Human genes 0.000 description 1
- 108090000623 proteins and genes Proteins 0.000 description 1
- NJGBTKGETPDVIK-UHFFFAOYSA-N raspberry ketone Chemical compound CC(=O)CCC1=CC=C(O)C=C1 NJGBTKGETPDVIK-UHFFFAOYSA-N 0.000 description 1
- 239000012429 reaction media Substances 0.000 description 1
- 239000011541 reaction mixture Substances 0.000 description 1
- 230000004044 response Effects 0.000 description 1
- UOGMZEGKCNHMBF-UHFFFAOYSA-N scentenal Chemical compound C12CC(C=O)CC2C2CC(OC)C1C2 UOGMZEGKCNHMBF-UHFFFAOYSA-N 0.000 description 1
- PUZPDOWCWNUUKD-UHFFFAOYSA-M sodium fluoride Chemical compound [F-].[Na+] PUZPDOWCWNUUKD-UHFFFAOYSA-M 0.000 description 1
- PDEFQWNXOUGDJR-UHFFFAOYSA-M sodium;2,2-dichloropropanoate Chemical compound [Na+].CC(Cl)(Cl)C([O-])=O PDEFQWNXOUGDJR-UHFFFAOYSA-M 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
- 230000003595 spectral effect Effects 0.000 description 1
- 238000001694 spray drying Methods 0.000 description 1
- 239000007858 starting material Substances 0.000 description 1
- 229910052717 sulfur Inorganic materials 0.000 description 1
- 239000011593 sulfur Substances 0.000 description 1
- 239000004094 surface-active agent Substances 0.000 description 1
- 235000007586 terpenes Nutrition 0.000 description 1
- NPFVOOAXDOBMCE-UHFFFAOYSA-N trans-3-hexenyl acetate Natural products CCC=CCCOC(C)=O NPFVOOAXDOBMCE-UHFFFAOYSA-N 0.000 description 1
- BJIOGJUNALELMI-UHFFFAOYSA-N trans-isoeugenol Natural products COC1=CC(C=CC)=CC=C1O BJIOGJUNALELMI-UHFFFAOYSA-N 0.000 description 1
- 235000013769 triethyl citrate Nutrition 0.000 description 1
- 150000004043 trisaccharides Chemical class 0.000 description 1
- KMPQYAYAQWNLME-UHFFFAOYSA-N undecanal Chemical compound CCCCCCCCCCC=O KMPQYAYAQWNLME-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
- FGQOOHJZONJGDT-UHFFFAOYSA-N vanillin Natural products COC1=CC(O)=CC(C=O)=C1 FGQOOHJZONJGDT-UHFFFAOYSA-N 0.000 description 1
- 235000012141 vanillin Nutrition 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
- C11B9/0007—Aliphatic compounds
- C11B9/0015—Aliphatic compounds containing oxygen as the only heteroatom
-
- 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
-
- 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
- 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
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61Q—SPECIFIC USE OF COSMETICS OR SIMILAR TOILETRY PREPARATIONS
- A61Q15/00—Anti-perspirants or body deodorants
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61Q—SPECIFIC USE OF COSMETICS OR SIMILAR TOILETRY PREPARATIONS
- A61Q19/00—Preparations for care of the skin
- A61Q19/10—Washing or bathing preparations
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61Q—SPECIFIC USE OF COSMETICS OR SIMILAR TOILETRY PREPARATIONS
- A61Q5/00—Preparations for care of the hair
- A61Q5/02—Preparations for cleaning the hair
Landscapes
- Life Sciences & Earth Sciences (AREA)
- Health & Medical Sciences (AREA)
- Chemical & Material Sciences (AREA)
- General Health & Medical Sciences (AREA)
- Veterinary Medicine (AREA)
- Public Health (AREA)
- Animal Behavior & Ethology (AREA)
- Engineering & Computer Science (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Oil, Petroleum & Natural Gas (AREA)
- Wood Science & Technology (AREA)
- Organic Chemistry (AREA)
- Epidemiology (AREA)
- Birds (AREA)
- Emergency Medicine (AREA)
- Fats And Perfumes (AREA)
- Cosmetics (AREA)
- Detergent Compositions (AREA)
- Dermatology (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Description
4−メチル−8−メチレン−4,9−デカジエナールは、例えばUS3872172に記載されているように、様々な文献に基本的にβ−シネンサール(オレンジオイルの公知の成分)の合成における中間体として記載されている公知の生成物である。
我々は、驚いたことに、下記式の4−メチル−8−メチレン−4,9−デカジエナール
i) 賦香成分として、少なくとも一つの上記記載の本発明の化合物;
ii) 香料担体および香料基剤からなる群より選ばれる少なくとも一つの成分;および
iii)場合により、少なくとも一つの香料補助剤
を含む賦香組成物である。
そこで、
i)賦香成分として少なくとも一つの上記で定義した式(I)の化合物、および
ii)消費者製品香料基剤
を含む賦香消費者製品もまた本発明の対象の一つである。
賦香組成物の製造
下記成分を混合することにより、草本系・フローラル・アルデヒドタイプの柔軟剤用の賦香組成物を製造した。
重量部 成分
300 オクチルアセテート
100 カルビノールアセテート
50 シクラノールアセテート
180 テルペニルアセテート
600 ベルジルアセテート
1000 イソボルニルアセテート
10 アルデヒドC10
750 ヘキシルシンナミックアルデヒド
70 アルデヒドMNA
10 アルデヒドsupra
50 アリルアミルグリコレート
20 10%*エチルカプロエート
50 Cetalox(R)1)
20 ラズベリーケトン
20 エチルシンナメート
500 CoranolTM2)
20 デルタダマスコン
200 ジヒドロミルセノール
200 4−シクロヘキシル−2−メチル−2−ブタノール
500 (1−エトキシエトキシ)シクロドデカン
400 Florol(R)3)
450 Hedione(R)4)
40 1,3−ベンゾジオキソール−5−カルバルデヒド
50 Hivernal(R)5)
500 Iso E(R)6) Super
50 イソオイゲノール
20 3,7−ジメチル−2/3,6−ノナジエンニトリル
100 Lilyflore(R)7)
20 1−(2,2,3,6−テトラメチル−シクロヘキシル−3−ヘキサノール
20 クリスタルモス(Cristal moss)
20 Myrrhone(R)8)
20 50%**(6R)−ペルヒドロ−3,6−ジメチル−ベンゾ[b]フラン−2−オン
50 Neobutenone(R)9)
100 Nirvanol(R)10)
30 トランス−1−(2,2,6−トリメチル−1−シクロヘキシル−3−ヘキサノール
100 3−メトキシ−7,7−ジメチル−10−メチレン−ビシクロ[4.3.1]デカン
200 パチュリオイル
300 オレンジ精油
50 1−メチル−4−(4−メチル−3−ペンテニル)−3−シクロヘキセン−1−カルボアルデヒド
400 ベルジルプロピアネート
150 イソボルニルプロピアネート
400 ローズワーディアオイル(Rose Wardia oil)
80 シス−3−ヘキセニルサリチレート
100 Salicynile(R)11)
900 Sclareolate(R)12)
80 テルピノレン
50 2,4−ジメチル−3−シクロヘキセン−1−カルボキシアルデヒド
50 γウンデカラクトン
20 バニリン
300 2−tert−ブチル−1−シクロヘキシルアセテート
9700
**イソプロピルミリステート中
1) ドデカヒドロ−3a,6,6,9a−テトラメチル−ナフト[2,1−b]フラン;製造元:Firmenich SA、スイス国ジュネーブ
2) 4−シクロヘキシル−2−メチル−2−ブタノール;製造元:Firmenich SA、スイス国ジュネーブ
3) テトラヒドロ−2−イソブチル−4−メチル−4(2H)−ピラノール;製造元:Firmenich SA、スイス国ジュネーブ
4) メチルジヒドロジャスモネート;製造元:Firmenich SA、スイス国ジュネーブ
5) 3−(3,3/1,1−ジメチル−5−インダニル)プロパナール;製造元:Firmenich SA、スイス国ジュネーブ
6) 1−(オクタヒドロ−2,3,8,8−テトラメチル−2−ナフタレニル)−1−エタノン;製造元:International Flavors&Fragrances、米国
7) (2,5−ジメチル−2,3−ジヒドロ−1H−インデン−2−イル)メタノール;製造元:Firmenich SA、スイス国ジュネーブ
8) 4−(2,2,C−3,T−6−テトラメチル−R−1−シクロヘキシル)−3−ブテン−2−オン;製造元:Firmenich SA、スイス国ジュネーブ
9) 1−(5,5−ジメチル−1−シクロヘキセン−1−イル)−4−ペンテン−1−オン;製造元:Firmenich SA、スイス国ジュネーブ
10) 3,3−ジメチル−5−(2,2,3−トリメチル−3−シクロペンテン−1−イル)−4−ペンテン−2−オール;製造元:Firmenich SA、スイス国ジュネーブ
11) (2Z)−2−フェニル−2−ヘキセンニトリル;製造元:Firmenich SA、スイス国ジュネーブ
12) プロピル(S)−2−(1,1−ジメチルプロポキシ)プロパノエート;製造元:Firmenich SA、スイス国ジュネーブ
賦香組成物の製造
下記成分を混合することにより、スズランタイプの粉末洗剤用の賦香組成物を製造した。
重量部 成分
60 シス−3−ヘキセニルアセテート
200 シンナミックアルコール
80 10%*アルデヒドC10
60 10%*アルデヒドC11 lenique
80 10%*アルデヒドC9
40 メチルアントラニレート
40 カモミールエステル
500 カルビノールミュゲ (Carbinol Muguet)
100 フェニルエチルシンナメート
1400 シトロネロール
500 CoranolTM1)
40 2−メチル−4−(2,2,3−トリメチル−3−シクロペンテン−1−イル)−4−ペンテン−1−オール
200 ゼラニウムオイル
900 Hedione(R)2)
400 ヒドロキシシトロネラール
80 10%*インドール
1200 ジャスミンオイル
500 Lilyflore(R)3)
1000 リナロール
500 フェネチロール
440 フェニルヘキサノール
400 Scentenal(R)4)
80 (2,2−ジメトキシエチル)ベンゼン
200 イランオイル
9000
**イソプロピルミリステート中
1) 4−シクロヘキシル−2−メチル−2−ブタノール;製造元:Firmenich SA、スイス国ジュネーブ
2) メチルジヒドロジャスモネート;製造元:Firmenich SA、スイス国ジュネーブ
3) (2,5−ジメチル−2,3−ジヒドロ−1H−インデン−2−イル)メタノール;製造元:Firmenich SA、スイス国ジュネーブ
4) 8(9)−メトキシ−トリシクロ[5.2.1.0.(2,6)]デカン−3(4)−カルボアルデヒド;製造元:Firmenich SA、スイス国ジュネーブ
Claims (9)
- 賦香組成物または賦香された物品に有効量の4−メチル−8−メチレン−4,9−デカジエナールを、その立体異性体のいずれか一つの形または(4−E)ジアステレオマーを少なくとも80%w/w含むジアステレオマー(4−E)および(4−Z)の混合物の形で添加することを含む、賦香組成物または賦香された物品に香気特性を付与、または賦香組成物または賦香された物品の香気特性を増進、向上または改良する方法。
- 4−メチル−8−メチレン−4,9−デカジエナールが、(4−E)ジアステレオマーを少なくとも80%w/w含むジアステレオマー(4−E)および(4−Z)の混合物の形で使用されることを特徴とする請求項1記載の方法。
- (E)−4−メチル−8−メチレン−4,9−デカジエナールを使用することを特徴とする、請求項1記載の方法。
- アルデヒド系および/またはスズランの香調を付与するために4−メチル−8−メチレン−4,9−デカジエナールを添加することを特徴とする請求項1記載の方法。
- i)4−メチル−8−メチレン−4,9−デカジエナールを、その立体異性体のいずれか一つの形で、または(4−E)ジアステレオマーを少なくとも80%w/w含むジアステレオマー(4−E)および(4−Z)の混合物の形で;
ii)香料担体及び香料基材からなる群から選ばれる少なくとも一つの成分;および
iii)場合により、少なくとも一つの香料補助剤
を含む賦香組成物。 - 香料基材が、草本系のアルデヒド、またはスズランの特徴を有することを特徴とする請求項5記載の賦香組成物。
- i)4−メチル−8−メチレン−4,9−デカジエナールを、その立体異性体のいずれか一つの形で、または(4−E)ジアステレオマーを少なくとも80%w/w含むジアステレオマー(4−E)および(4−Z)の混合物の形で;および
ii)消費者製品香料基剤
を含む賦香消費者製品。 - 消費者製品香料基剤が香水、繊維ケア製品、ボディケア製品、空間ケア製品または家庭用ケア製品であることを特徴とする、請求項7記載の賦香消費者製品。
- 消費者製品香料基剤が、ファインパフューム、コロン、アフターシェイブローション、液体または固形洗剤、繊維柔軟剤、繊維消臭剤、アイロンがけ用の水、紙、漂白剤、シャンプー、着色剤、ヘアスプレー、バニッシングクリーム、消臭剤または制汗剤、賦香された石鹸、シャワー用またはバス用のムース、オイルもしくはジェル、衛生用品、エアフレッシュナー、「すぐに使える」粉末状エアフレッシュナー、ふきん、食器用洗剤、または硬質表面用洗剤であることを特徴とする請求項7記載の賦香消費者製品。
Applications Claiming Priority (3)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
EP11194414 | 2011-12-20 | ||
EP11194414.6 | 2011-12-20 | ||
PCT/EP2012/074703 WO2013092240A1 (en) | 2011-12-20 | 2012-12-06 | New aldehyde as perfuming ingredient |
Publications (2)
Publication Number | Publication Date |
---|---|
JP2015509116A JP2015509116A (ja) | 2015-03-26 |
JP5930347B2 true JP5930347B2 (ja) | 2016-06-08 |
Family
ID=47291024
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
JP2014547833A Expired - Fee Related JP5930347B2 (ja) | 2011-12-20 | 2012-12-06 | 賦香成分としての新規なアルデヒド |
Country Status (6)
Country | Link |
---|---|
US (1) | US9187708B2 (ja) |
EP (1) | EP2794829B1 (ja) |
JP (1) | JP5930347B2 (ja) |
CN (1) | CN103998588A (ja) |
IN (1) | IN2014CN04013A (ja) |
WO (1) | WO2013092240A1 (ja) |
Families Citing this family (5)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
WO2017055458A1 (en) * | 2015-10-01 | 2017-04-06 | Firmenich Sa | Vetiver odorant |
US20190343977A1 (en) * | 2016-11-18 | 2019-11-14 | Firmenich Sa | Use of volatile compositions to limit or eliminate perception of fecal malodour |
WO2018091686A1 (en) * | 2016-11-18 | 2018-05-24 | Firmenich Sa | Use of volatile compositions to limit or eliminate perception of fecal malodour |
CN112566890A (zh) * | 2018-10-30 | 2021-03-26 | 弗门尼舍有限公司 | 作为加香成分的环氧基醚化合物 |
GB202115380D0 (en) * | 2021-10-26 | 2021-12-08 | Givaudan Sa | Organic compounds |
Family Cites Families (9)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
CH514528A (de) | 1967-07-07 | 1971-10-31 | Givaudan & Cie Sa | Verfahren zur Herstellung von Aldehyden |
CH491843A (fr) * | 1967-12-14 | 1970-06-15 | Firmenich & Cie | Procédé de préparation d'aldéhydes non saturés |
US3965198A (en) * | 1974-01-25 | 1976-06-22 | Givaudan Corporation | 4-Methylene-5-hexen-1-ol |
GB2048253B (en) * | 1979-03-22 | 1983-08-03 | Bush Boake Allen Ltd | 4,8-dimethyl-4,9-decanedienal and its use un perfumery |
NL8402579A (nl) * | 1984-08-23 | 1986-03-17 | Naarden International Nv | Parfumcomposities en geparfumeerde produkten, die een of meer 4,7-alkadienalen als grondstof bevatten. |
JP4110490B2 (ja) * | 1998-03-30 | 2008-07-02 | 曽田香料株式会社 | β−シネンサールの製造法 |
CN101083975B (zh) * | 2004-12-20 | 2010-12-01 | 昭和电工株式会社 | 毛发处理剂和烫发方法 |
CA2675426A1 (en) * | 2007-02-15 | 2008-08-21 | The Procter & Gamble Company | Benefit agent delivery compositions |
JP5156272B2 (ja) * | 2007-06-15 | 2013-03-06 | 大洋香料株式会社 | 新規香料成分及び香料組成物 |
-
2012
- 2012-12-06 US US14/367,218 patent/US9187708B2/en active Active
- 2012-12-06 EP EP12795485.7A patent/EP2794829B1/en active Active
- 2012-12-06 CN CN201280062848.6A patent/CN103998588A/zh active Pending
- 2012-12-06 JP JP2014547833A patent/JP5930347B2/ja not_active Expired - Fee Related
- 2012-12-06 WO PCT/EP2012/074703 patent/WO2013092240A1/en active Application Filing
-
2014
- 2014-05-28 IN IN4013CHN2014 patent/IN2014CN04013A/en unknown
Also Published As
Publication number | Publication date |
---|---|
EP2794829B1 (en) | 2015-09-16 |
US9187708B2 (en) | 2015-11-17 |
WO2013092240A1 (en) | 2013-06-27 |
US20150005213A1 (en) | 2015-01-01 |
IN2014CN04013A (ja) | 2015-10-23 |
JP2015509116A (ja) | 2015-03-26 |
CN103998588A (zh) | 2014-08-20 |
EP2794829A1 (en) | 2014-10-29 |
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