EP0409089A2 - 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 PDFInfo
- Publication number
- EP0409089A2 EP0409089A2 EP90113370A EP90113370A EP0409089A2 EP 0409089 A2 EP0409089 A2 EP 0409089A2 EP 90113370 A EP90113370 A EP 90113370A EP 90113370 A EP90113370 A EP 90113370A EP 0409089 A2 EP0409089 A2 EP 0409089A2
- 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.)
- Granted
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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 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.
- 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.
- 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 which 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) was 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) Parts by Weight Sagetone V (1) 100 Sandal mysore core (2) 20 ⁇ - Methyl ionon 100 Pearllide DEP (3) 100 Methyl dihydroxy jasmonate 200 Rose base 100 Galbanum oil 10 Pollenal V (4) 10 Lemon oil 50 Bergamot oil 100 Fruitate (5) 10 800 (1) Sagetone V: Product name of Kao Corp.
- 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)
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 true EP0409089A2 (fr) | 1991-01-23 |
| EP0409089A3 EP0409089A3 (en) | 1991-10-23 |
| EP0409089B1 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 (3)
| 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 |
| EP2502978A1 (fr) * | 2011-03-24 | 2012-09-26 | International Flavors & Fragrances Inc. | Formulation de parfum à haute performance |
| CN102807473A (zh) * | 2012-03-16 | 2012-12-05 | 成都中医药大学 | 广藿香醇的分离纯化方法 |
Families Citing this family (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| 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 |
| 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 |
| 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 |
| GR1011083B (el) * | 2025-04-05 | 2025-11-25 | Θεοδωρος Νικολαου Καλοτινης | Μεθοδος παραγωγης ρεαλιστικων αρωματων με γαστρονομικη προσεγγιση ζαχαροπλαστικης |
Family Cites Families (2)
| 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 |
-
1989
- 1989-07-20 JP JP1188044A patent/JP2562205B2/ja not_active Expired - Fee Related
-
1990
- 1990-07-12 EP EP19900113370 patent/EP0409089B1/fr not_active Expired - Lifetime
- 1990-07-12 DE DE1990615034 patent/DE69015034T2/de not_active Expired - Fee Related
Cited By (4)
| 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 |
| EP2502978A1 (fr) * | 2011-03-24 | 2012-09-26 | International Flavors & Fragrances Inc. | Formulation de parfum à haute performance |
| CN102807473A (zh) * | 2012-03-16 | 2012-12-05 | 成都中医药大学 | 广藿香醇的分离纯化方法 |
| 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 |
Also Published As
| Publication number | Publication date |
|---|---|
| EP0409089B1 (fr) | 1994-12-14 |
| DE69015034T2 (de) | 1995-05-24 |
| DE69015034D1 (de) | 1995-01-26 |
| EP0409089A3 (en) | 1991-10-23 |
| JP2562205B2 (ja) | 1996-12-11 |
| JPH0352834A (ja) | 1991-03-07 |
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