EP0409089B1 - Huile de patchouli parfumée et une composition de parfum comprenant la dite huile de patchouli - Google Patents

Huile de patchouli parfumée et une composition de parfum comprenant la dite huile de patchouli Download PDF

Info

Publication number
EP0409089B1
EP0409089B1 EP19900113370 EP90113370A EP0409089B1 EP 0409089 B1 EP0409089 B1 EP 0409089B1 EP 19900113370 EP19900113370 EP 19900113370 EP 90113370 A EP90113370 A EP 90113370A EP 0409089 B1 EP0409089 B1 EP 0409089B1
Authority
EP
European Patent Office
Prior art keywords
patchouli
patchouli oil
oil
norpatchoulenol
alcohol
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.)
Expired - Lifetime
Application number
EP19900113370
Other languages
German (de)
English (en)
Other versions
EP0409089A3 (en
EP0409089A2 (fr
Inventor
Yoshiaki Fujikura
Hiroaki Uchida
Junji Koshino
Manabu Fujita
Nao Toi
Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)
Kao Corp
Original Assignee
Kao Corp
Priority date (The priority date 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 date listed.)
Filing date
Publication date
Application filed by Kao Corp filed Critical Kao Corp
Publication of EP0409089A2 publication Critical patent/EP0409089A2/fr
Publication of EP0409089A3 publication Critical patent/EP0409089A3/en
Application granted granted Critical
Publication of EP0409089B1 publication Critical patent/EP0409089B1/fr
Anticipated expiration legal-status Critical
Expired - Lifetime legal-status Critical Current

Links

Images

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
    • C11B9/0042—Essential oils; Perfumes compounds containing condensed hydrocarbon 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
    • C11B9/02—Recovery or refining of essential oils from raw materials

Definitions

  • the present invention is directed to a patchouli oil which contains a certain amount of patchouli alcohol having an improved fragrance, and a perfume composition comprising said patchouli alcohol.
  • Patchouli oil is utilized as a fragrance in a wide variety of fields including its use as a perfume for soap.
  • patchouli oil itself has a herbal, spicy, balsamic and woody odor, it cannot be combined into a combination perfume in a large amount, and thus the amount that can be used is limited.
  • patchouli oil which is contained in patchouli oil in amount of about 30% by weight.
  • Patchouli oil has a very interesting odor, namely, it has a camphoraceous, woody, earthy and amber odor. Isolation of patchouli alcohol can be done by distilling patchouli oil to enhance the content of patchouli alcohol and crystallizing it.
  • the ratio of norpatchoulenol to patchouli alcohol in a correctly distilled patchouli oil is about 1:40 (Seifen, ⁇ le, Fette, Wachse, vol. 103, 07.04.77, pages 159-161, F.W. Hefendehl et al., "Die analyticiantechnisch von Patchouliöl").
  • the present invention was accomplished based on the above findings.
  • the present invention is directed to a fragrant patchouli oil which comprises 70 to 99.6% by weight of patchouli alcohol, and 0.4 to 5.0% by weight of norpatchoulenol, wherein the hydrocarbons, which have a nasty top note, have been removed.
  • an essential oil which has a rich, powerful and fresh odor can be obtained by distilling a patchouli oil and by precisely controlling the content of both norpatchoulenol and patchouli alcohol while removing the hydrocarbons which have a nasty top note odor and which are associated with patchouli oil which comprises 70 to 99.6% by weight of patchouli alcohol, and 0.4 to 5.0% by weight of norpatchoulenol.
  • the present invention is also directed to a combination perfume which comprises a perfume base; and a fragrance emitting effective amount of patchouli oil which comprises 70 to 99.6% by weight of patchouli alcohol, and 0.4 to 5.0% by weight of norpatchoulenol.
  • Fig. 1 is the capillary gas chromatography chart of patchouli oil in Example 2.
  • Fig. 2 is the capillary gas chromatography chart of patchouli oil in Comparative Example 3.
  • Horizontal axes in Fig. 1 and Fig. 2 represent retention time (unit:minute) and vertical axes represent strength respectively.
  • A. represents the peak for norpatchoulenol and B. represents the peak for patchouli alcohol.
  • the present inventors have conducted research in order to find a method for increasing the content of patchouli alcohol by means of distillation without recrystallization. Namely, they have studied a method which consists of distilling off the low boiling portion of a patchouli oil by rectification and then distilling the main distillate which includes the patchouli alcohol. By means of this method, the content of patchouli alcohol can be increased up to around 85% by weight.
  • patchouli oil having a high content of patchouli alcohol for example, 85% by weight, does not have a powerful and characteristic odor, and as a result is less attractive for use as a perfume material.
  • the present inventors have made intensive studies in order to improve this less attractive effect and, as a result, found that when a patchouli oil contains a larger proportion of a low boiling point material and the content of patchouli alcohol is lowered a little, the patchouli oil has an excellent fragrance. Namely, the present inventors have found that norpatchoulenol, which has a lower boiling point than that of patchouli alcohol, surprisingly stresses or modifies the odor of patchouli alcohol, the high boiling point material.
  • a sample which contains about 80% by weight of patchouli alcohol and which is well evaluated with respect to odor was fractionated by using preparative liquid chromatography to prepare a sample in which only norpatchoulenol was removed.
  • distillation in order to efficiently remove the nasty top note smell.
  • the theoretical plates of the rectification are five or more, preferably ten or more.
  • the distillation can be conducted under ordinary pressure or reduced pressure. It is unfavorable for product quality to expose patchouli alcohol to heat for a long period of time. Accordingly, distillation under reduced pressure is preferable, generally in the range of from 0.01 to 50 mm Hg; however the pressure is not necessarily limited to this range.
  • the temperature at the top of a distillation column depends upon the number of rectification plates and reduced pressure, it is generally in the range of from 50 to 300°C.
  • One purpose of the present invention is to obtain a patchouli oil comprising 70.0 to 99.6% by weight of patchouli alcohol and 0.40 to 5.0% by weight of norpatchoulenol by means of distillation.
  • a variety of methods for distillation can be used. For example, one method is to fractionate the first main distillate, combining some of the fractions of the first main distillate with the second main distillate. Another method is to distill the patchouli oil to collect a distillate having the same component as the combination of fractions described above in the form of one distillate by controlling the number of plates of the distillation column, the reduced pressure and the distillation temperature.
  • the patchouli oil of the present invention which comprises an increased amount of patchouli alcohol and a certain amount of norpatchoulenol does not have a green or earthy top note, but rather a mild sweet, woody, balsamic and amber-like odor.
  • the patchouli oil of the present invention is better balanced in odor than that of patchouli alcohol itself because it comprises an appropriate amount or norpatchoulenol.
  • a perfume composition of the present invention is very useful as a high-grade fragrance compound material for soaps, cosmetics, perfumes, etc.
  • Respective amounts of patchouli oil (manufactured by T. Hasegawa Co., Ltd., Tokyo, Japan) were distilled off to remove the respective amounts of initial distillates as shown in Table 1 using a distillation column having the number of theoretical plates described in Table 1 under initial distillation conditions (reflux ratio, temperature, pressure).
  • Each patchouli oil obtained was analyzed by capillary gas chromatography to measure the content of patchouli alcohol and norpatchoulenol. Each patchouli oil obtained was also evaluated with respect to its aromaticity. The results are shown in Table 1. Furthermore, as to the patchouli oil of Example 2, its capillary gas chromatography chart is shown in Figure 1.
  • Example 2 Two thousand four hundred and ten (2410) mg of patchouli oil obtained in Example 2 was separated into a 2240 mg portion containing no norpatchoulenol and a 170 mg portion containing norpatchoulenol by using high pressure liquid chromatography (HPLC) packed with Inertsil Prep-SIL (manufactured by Gasukuro Kogyo, Inc.), normal phase column, and 3% ethyl acetate/hexane as eluent.
  • HPLC high pressure liquid chromatography
  • One hundred and forty (140) mg of the remaining portion was combined with the above described 2240 mg of the portion, containing no norpatchoulenol, to obtain 2380 mg of the patchouli oil which has same composition as "patchouli oil” which is obtained by removing only norpatchoulenol from the patchouli oil of Example 2.
  • the patchouli oil obtained was analyzed by capillary gas chromatography to measure the content of patchouli alcohol and norpatchoulenol.
  • the patchouli oil obtained does not have a volumerous and sweet odor.
  • a capillary gas chromatography chart of the patchouli oil is shown in Figure 2.
  • the amount of patchouli oil of the present invention in fragrance compositions is not limited to any range. However, a preferred range of the patchouli alcohol in fragrance compositions is from 1% to 50% by weight based on the total weight of said composition.
  • Example 7 (Example of floral bouquet combination perfume)
  • Floral bouquet perfume compositions having a fresh and rich odor can be obtained by adding 200 parts by weight of the invention composition in Example 1 into the above-mentioned combination perfume.

Landscapes

  • Chemical & Material Sciences (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • Engineering & Computer Science (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Oil, Petroleum & Natural Gas (AREA)
  • Wood Science & Technology (AREA)
  • Organic Chemistry (AREA)
  • Cosmetics (AREA)
  • Fats And Perfumes (AREA)
  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)

Claims (4)

  1. Essence de patchouli parfumée, qui comprend 70 à 99,6% en poids d'alcool de patchouli, et 0,4 à 5,0% en poids de norpatchoulénol, dans laquelle les hydrocarbures, qui ont une note de tête désagréable, ont été éliminés.
  2. Composition de parfum de combinaison, qui comprend une base de parfum et une quantité efficace pour émettre un parfum d'une essence de patchouli suivant la revendication 1.
  3. Composition suivant la revendication 2, dans laquelle cette quantité efficace pour émettre un parfum de cette essence de patchouli est présente en une quantité de 1% à 50% en poids par rapport au poids total de cette composition.
  4. Utililisation d'une essence de patchouli suivant la revendication 1, en tant que parfum.
EP19900113370 1989-07-20 1990-07-12 Huile de patchouli parfumée et une composition de parfum comprenant la dite huile de patchouli Expired - Lifetime EP0409089B1 (fr)

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
JP188044/89 1989-07-20
JP1188044A JP2562205B2 (ja) 1989-07-20 1989-07-20 香気の良いパチュリ油、その製法およびこれを含有する香料組成物

Publications (3)

Publication Number Publication Date
EP0409089A2 EP0409089A2 (fr) 1991-01-23
EP0409089A3 EP0409089A3 (en) 1991-10-23
EP0409089B1 true EP0409089B1 (fr) 1994-12-14

Family

ID=16216703

Family Applications (1)

Application Number Title Priority Date Filing Date
EP19900113370 Expired - Lifetime EP0409089B1 (fr) 1989-07-20 1990-07-12 Huile de patchouli parfumée et une composition de parfum comprenant la dite huile de patchouli

Country Status (3)

Country Link
EP (1) EP0409089B1 (fr)
JP (1) JP2562205B2 (fr)
DE (1) DE69015034T2 (fr)

Cited By (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CN101935591A (zh) * 2010-09-10 2011-01-05 吉水县金海天然香料油科技有限公司 广藿香油精制提取方法
GR1011083B (el) * 2025-04-05 2025-11-25 Θεοδωρος Νικολαου Καλοτινης Μεθοδος παραγωγης ρεαλιστικων αρωματων με γαστρονομικη προσεγγιση ζαχαροπλαστικης

Families Citing this family (6)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
RU2114165C1 (ru) * 1998-03-16 1998-06-27 Закрытое акционерное общество Научно-производственное объединение "Химсинтез" Раствор душистых веществ для парфюмерно-косметической продукции
KR100318630B1 (ko) * 1999-12-30 2001-12-28 박명규 광곽향 추출물 및 그 제조방법과 추출물을 함유한 담배
CN101691323B (zh) * 2009-10-15 2012-04-25 东莞广州中医药大学中医药数理工程研究院 一种广藿香醇的分离纯化方法
US20120245075A1 (en) * 2011-03-24 2012-09-27 Timothy Jay Young High Performance Fragrance Formulation
CN102807473B (zh) * 2012-03-16 2014-07-30 成都华神集团股份有限公司 广藿香醇的分离纯化方法
JP2013241570A (ja) * 2012-04-27 2013-12-05 Takasago Internatl Corp 組成物、及び、それを含有する製品、並びにその組成物で香料組成物の香気特性を改善する方法

Family Cites Families (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
BE788301A (fr) * 1971-09-01 1973-03-01 Roure Bertrand Fils & Justin S Alcool tricyclique
JPS56103125A (en) * 1980-01-04 1981-08-18 Roure Bertrand Dupont Sa Tricyclic compound

Cited By (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CN101935591A (zh) * 2010-09-10 2011-01-05 吉水县金海天然香料油科技有限公司 广藿香油精制提取方法
CN101935591B (zh) * 2010-09-10 2012-05-23 吉水县金海天然香料油科技有限公司 广藿香油精制提取方法
GR1011083B (el) * 2025-04-05 2025-11-25 Θεοδωρος Νικολαου Καλοτινης Μεθοδος παραγωγης ρεαλιστικων αρωματων με γαστρονομικη προσεγγιση ζαχαροπλαστικης

Also Published As

Publication number Publication date
DE69015034T2 (de) 1995-05-24
DE69015034D1 (de) 1995-01-26
EP0409089A3 (en) 1991-10-23
EP0409089A2 (fr) 1991-01-23
JP2562205B2 (ja) 1996-12-11
JPH0352834A (ja) 1991-03-07

Similar Documents

Publication Publication Date Title
AU641016B2 (en) Method of producing eicosapentaenoic acid or the ester derivatives thereof
US4610813A (en) Hydroxylic campholenic aldehyde derivatives, their utilization as perfume ingredients and perfuming compositions containing same
EP0409089B1 (fr) Huile de patchouli parfumée et une composition de parfum comprenant la dite huile de patchouli
JPH0138438B2 (fr)
JPH08319250A (ja) 香 料
EP0694605B1 (fr) Diester cyclique et son utilisation à titre d'ingrédient parfumant
EP0358298A1 (fr) Composition de parfum et méthode
EP0584477B1 (fr) Utilisation d'une cyclopentadécénone à titre d'ingrédient parfumant
EP0504592B1 (fr) Alcool tertiare à sous-structure campholénique et son utilisation à titre d'ingrédient parfumant
US4524019A (en) Spiro-lactone derivatives, their use as perfuming agents, and perfuming composition containing same
EP0581052B1 (fr) Utilisation du tétrahydro-4-méthyl-2-phényl-2H-pyranne en tant qu'ingrédient parfumant
US4519944A (en) Spirolactones as odorants
US4146507A (en) Novel cyclohexene-3-nitriles in perfume compositions
US4904465A (en) Perfuming ingredient, process for its preparation and utilization of said ingredient in perfuming compositions and perfumed products
Anonis Neroli in perfumery
US4197246A (en) Novel norcamphanyl-substituted pyrans, method for their synthesis and use thereof in perfumery
US6242413B1 (en) Bicyclic aldehyde and ketone odorants
US4464280A (en) Organoleptic uses of phenyl ethyl methyl carbonate mixtures
EP0676393B1 (fr) Cétones cycliques nouvelles et leur utilisation en parfumerie
US5512543A (en) Use of optically active isomers of (E)-3,3-dimethyl-5-(2,2,3-trimethyl-3-cyclopenten-1-YL)-4-penten-2-OL as perfuming ingredients
US4795738A (en) Arbozol containing perfume or fragrance compositions
EP0572797B1 (fr) Alcools cycliques non-saturés leur utilisation à titre d'ingrédients parfumants et leurs intermédiaires.
EP0841318B1 (fr) Isomères optiques de dérivés de l'aldéhyde campholénique
US4363754A (en) 4(5)-Acetyl-9,9-dimethyltricyclo-[4,4,0,18,10 ]-undec-1-ene, its preparation and use in perfumery compositions and as an odorant
EP0916650A2 (fr) Nitriles et aldéhydes dérivés du 3-isopropényl-1,2-diméthyl-1-cyclopentanol et leur utilisation en parfumerie

Legal Events

Date Code Title Description
PUAI Public reference made under article 153(3) epc to a published international application that has entered the european phase

Free format text: ORIGINAL CODE: 0009012

AK Designated contracting states

Kind code of ref document: A2

Designated state(s): CH DE FR GB LI NL

PUAL Search report despatched

Free format text: ORIGINAL CODE: 0009013

AK Designated contracting states

Kind code of ref document: A3

Designated state(s): CH DE FR GB LI NL

17P Request for examination filed

Effective date: 19920129

17Q First examination report despatched

Effective date: 19931124

GRAA (expected) grant

Free format text: ORIGINAL CODE: 0009210

AK Designated contracting states

Kind code of ref document: B1

Designated state(s): CH DE FR GB LI NL

REF Corresponds to:

Ref document number: 69015034

Country of ref document: DE

Date of ref document: 19950126

ET Fr: translation filed
PG25 Lapsed in a contracting state [announced via postgrant information from national office to epo]

Ref country code: CH

Effective date: 19950731

Ref country code: LI

Effective date: 19950731

PLBE No opposition filed within time limit

Free format text: ORIGINAL CODE: 0009261

STAA Information on the status of an ep patent application or granted ep patent

Free format text: STATUS: NO OPPOSITION FILED WITHIN TIME LIMIT

26N No opposition filed
PG25 Lapsed in a contracting state [announced via postgrant information from national office to epo]

Ref country code: NL

Effective date: 19960201

REG Reference to a national code

Ref country code: CH

Ref legal event code: PL

NLV4 Nl: lapsed or anulled due to non-payment of the annual fee

Effective date: 19960201

REG Reference to a national code

Ref country code: GB

Ref legal event code: IF02

PGFP Annual fee paid to national office [announced via postgrant information from national office to epo]

Ref country code: DE

Payment date: 20060706

Year of fee payment: 17

PGFP Annual fee paid to national office [announced via postgrant information from national office to epo]

Ref country code: GB

Payment date: 20060712

Year of fee payment: 17

PGFP Annual fee paid to national office [announced via postgrant information from national office to epo]

Ref country code: FR

Payment date: 20060719

Year of fee payment: 17

GBPC Gb: european patent ceased through non-payment of renewal fee

Effective date: 20070712

PG25 Lapsed in a contracting state [announced via postgrant information from national office to epo]

Ref country code: DE

Free format text: LAPSE BECAUSE OF NON-PAYMENT OF DUE FEES

Effective date: 20080201

PG25 Lapsed in a contracting state [announced via postgrant information from national office to epo]

Ref country code: GB

Free format text: LAPSE BECAUSE OF NON-PAYMENT OF DUE FEES

Effective date: 20070712

REG Reference to a national code

Ref country code: FR

Ref legal event code: ST

Effective date: 20080331

PG25 Lapsed in a contracting state [announced via postgrant information from national office to epo]

Ref country code: FR

Free format text: LAPSE BECAUSE OF NON-PAYMENT OF DUE FEES

Effective date: 20070731