GB2237805A - Diketone extraction - Google Patents
Diketone extraction Download PDFInfo
- Publication number
- GB2237805A GB2237805A GB9024116A GB9024116A GB2237805A GB 2237805 A GB2237805 A GB 2237805A GB 9024116 A GB9024116 A GB 9024116A GB 9024116 A GB9024116 A GB 9024116A GB 2237805 A GB2237805 A GB 2237805A
- Authority
- GB
- United Kingdom
- Prior art keywords
- process according
- diketone
- acid
- acetic acid
- extraction
- 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
Links
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D307/00—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom
- C07D307/77—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom ortho- or peri-condensed with carbocyclic rings or ring systems
- C07D307/78—Benzo [b] furans; Hydrogenated benzo [b] furans
- C07D307/79—Benzo [b] furans; Hydrogenated benzo [b] furans with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached to carbon atoms of the hetero ring
-
- 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
- A61K8/49—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds containing heterocyclic compounds
- A61K8/4973—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds containing heterocyclic compounds with oxygen as the only hetero atom
-
- 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
- A61K8/96—Cosmetics or similar toiletry preparations characterised by the composition containing materials, or derivatives thereof of undetermined constitution
- A61K8/97—Cosmetics or similar toiletry preparations characterised by the composition containing materials, or derivatives thereof of undetermined constitution from algae, fungi, lichens or plants; from derivatives thereof
- A61K8/9783—Angiosperms [Magnoliophyta]
- A61K8/9789—Magnoliopsida [dicotyledons]
-
- 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
Landscapes
- Life Sciences & Earth Sciences (AREA)
- Health & Medical Sciences (AREA)
- Organic Chemistry (AREA)
- Chemical & Material Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- General Health & Medical Sciences (AREA)
- Public Health (AREA)
- Veterinary Medicine (AREA)
- Epidemiology (AREA)
- Birds (AREA)
- Engineering & Computer Science (AREA)
- Biotechnology (AREA)
- Botany (AREA)
- Microbiology (AREA)
- Mycology (AREA)
- Dermatology (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Abstract
A process for the extraction of a diketone, e.g. 'pongamol', comprises the steps of: i) extracting plant material obtained from Pongamia sp. or from Tephrosia sp. with an organic acid, and ii) separating a diketone from the acidic extract so obtained.
Description
METHOD OF EXTRACTION
FIELD OF THE INVENTION
This invention relates to extraction of natural substances from plant materials. The invention particularly relates to extraction of diketones useful for cosmetic applications, from certain plants of species like Ponsamia glabra, P.Pinnata, Tephrosia Durpurea,
T.Hamiltoni, T.flasiformis, T.Voaellii, T.lanceolata.
The invention more particularly concerns a process for directly isolating "pongamol" [1,3-propanedione, 1-(4 methoxy-5-benzofuranyl)-3-phenyl] from the oil obtained from any part of the plant such as shell, bark, root, stem or seed. More specifically, the invention teaches a method of extraction of pongamol from commercial karanja oil, obtained from the seed by crushing, or by solvent extraction of the seed or cake.
BACKGROUND TO THE INVENTION AND PRIOR ART
Pongamol has been isolated from karanja oil by different methods such as molecular distillation of oil (N.V.Bringi, JOTA, (India), [1976), 8(3) 81) which required very high vacuum.
Other earlier researchers have isolated pongamol from karanja oil by a series of steps, usually involving separation from karanjin, followed by alcohol extraction of the oil and further purification.
In the process described in Ind.J.Pharm.(1941), 3, 3, and Proc. of Ind.Acad.Sci., (1942), 15A, 437, the karanja oil is first stored to remove karanjin and extracted with alcohol. The alcohol extract is stored and the separated material is taken up in ether and crystallised from ethanol-acetic acid.
In the process described in J.Ind.Chem.Soc.,
Industrial and News edition tl954], 17 39, dry hydrogen chloride is passed through the alcohol extract of karanja oil, the precipitate is separated and fractionally crystallised.
In the procedure described by R.N. Rhanna and
T.R. Seshadri in Tetrahedron [1963], 19, 223, the oily alcohol extract of the karanja oil, was stored in refrigerator (precipitated karanjin removed) and then chromatrographed over alumina. From the light petroleum eluate, pongamol was isolated by countercurrent distribution between aqueous acetic acid and light petroleum.
The above procedure was modified by R. Aneja,
R.N. Khanna and T. R. Seshadri (J.Chem.Soc., [1963), p.163) by eliminating the chromatographic step, but carrying out repeated partitioning of karanjin-removed-alcohol-extract between light petroleum and aqueous acetic acid.
We have surprisingly found that pongamol can be directly extracted from karanja oil, using concentrated/dilute organic acid, like formic, acetic, propionic and butyric acid, for example, aqueous acetic acid.
DEFINITION OF THE INVENTION
Accordingly, the invention provides a process for the extraction of a diketone which comprises the steps of:
i) extracting plant material obtained from Ponpamia sp. or from Tephrosia sp. with an
organic acid, and
ii) separating a diketone from the acidic
extract so obtained.
DESCRIPTION OF THE INVENTION
In accordance with the process of the invention, plant materials, especially the oils obtained from the shell, bark, root, stem or seed of Ponqamia sp. or of
Tephrosia sp. are extracted with an organic acid, and diketones present in the extracts so obtained, are subsequently separated.
In accordance with a preferred embodiment of the invention, karanja oil is extracted using concentrated or dilute aqueous acetic acid in order to dissolve pongamol present in this starting material.
The extracts, after removal of the acid, are directly of use as enriched pongamol, or can be purified further by crystallisation from solvents, such as methanol or acetic acid.
Most preferably, pongamol can be directly obtained from karanja oil by extraction and in situ crystallisation with concentrated/dilute organic acid, ideally aqueous acetic acid, for example, 30 to 99% w/w, preferably 65 to 85% w/w acetic acid. The crystallisation can be carried out at a temperature of from 0 to 350c, with or without the aid of conventional methods for accelerating crystallisation, such as seeding. Accordingly, karanja oil is stirred with aqueous organic acid at ambient temperature and the aqueous acid layer is separated and kept at ambient temperature to crystallise out pongamol, which is then filtered out and freed of adhering oil and acetic acid solution by washing with solvents, such as methanol and/or hexane.
According to another aspect of the invention, pongamol can be obtained from karanja oil settlings or split karanja oil fatty acids as well as from distilled fatty acid residues.
The invention is now described by way of example.
The following example is intended to illustrate the invention and not to limit it.
EXAMPLES
Example 1
Karanja oil, commercial grade, Sangli Region, Acid value 11.4 (2000g) was stirred with aqueous acetic solution (800 ml glacial acetic acid diluted to 1000 ml) for 1 hr at ambient temperature (25 to 300C). It was then allowed to settle and the aqueous layer separated (912g)
The oil layer was re-extracted with 1000 ml of aqueous acetic acid of the above composition and aqueous layer separated (990g). The combined extracts (1902g) were held at ambient temperature (25-300C) for 3 days and crystals of pongamol were collected by filtration. They were washed with hexane (b.p. 65/700C) 3 x 70 ml and dried in vacuum (N5mm) at ambient temperature.
The pongamol isolated (18g) was homogenous on tlc (hexane:ether:acetic acid 3:1:0.1), had a melting point of from 1260C to 127.50C and UV absorption \ max at 350 nm; the extinction coefficient E was 21,800 and structural confirmation was done by melting point and spectral data.
The oil remaining after the separation of aqueous acid layer can be washed by stirring with water (2 x 200 ml) for 30 minutes followed by settling, then similarly with saturated brine (2 x 500 ml) at 80"C to free acetic acid, and the washed oil recovered (1855 g).
This recovered oil so obtained is of higher quality than raw karanja oil, and can be used for making good quality soap. Hardening of the recovered oil is easier to achieve, as catalyst consumption is lower than that experienced when raw karanja oil is used.
Claims (11)
1. A process for the extraction of a diketone which comprises the steps of:
i) extracting plant material obtained from Ponsamia sp. or from Tephrosia sp. with an
organic acid, and
ii) separating a diketone from the acidic
extract so obtained.
2. A process according to claim 1, in which the diketone is Pongamol.
3. A process according to claim 1 or 2, in which the plant material is chosen from oil derived from shell, bark, root, stem, seed and mixtures thereof.
4. A process according to any of claims 1, 2 or 3, in which the Ponqamia sp. is chosen from P. alabra and
P. pinnata.
5. A process according to claim 1, 2 or 3, in which the
Tephrosia sp. is chosen from T. purpurea, T. Hamiltoni,
T. flasiformis, T. Voqellii, and T. Lanceolata.
6. A process according to any preceding claim, in which the organic acid is aqueous acetic acid.
7. A process according to claim 6, in which the aqueous acetic acid comprises from 65 to 85% w/w acetic acid.
8. A process according to any preceding claim, in which separation of the diketone from the acid extract is accomplished via crystallisation.
9. A process according to claim 8, in which the crystallisation of the diketone isdirectly from the extract.
10. A process according to claim 8, in which the crystallisation of the diketone is achieved from an organic solvent solution following removal of the acid used for extraction.
11. A process according to claim 10, in which the organic solvent is methanol.
Applications Claiming Priority (1)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
GB898925515A GB8925515D0 (en) | 1989-11-10 | 1989-11-10 | Method of extraction |
Publications (3)
Publication Number | Publication Date |
---|---|
GB9024116D0 GB9024116D0 (en) | 1990-12-19 |
GB2237805A true GB2237805A (en) | 1991-05-15 |
GB2237805B GB2237805B (en) | 1992-12-23 |
Family
ID=10666137
Family Applications (2)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
GB898925515A Pending GB8925515D0 (en) | 1989-11-10 | 1989-11-10 | Method of extraction |
GB9024116A Expired - Lifetime GB2237805B (en) | 1989-11-10 | 1990-11-06 | Method of extraction |
Family Applications Before (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
GB898925515A Pending GB8925515D0 (en) | 1989-11-10 | 1989-11-10 | Method of extraction |
Country Status (3)
Country | Link |
---|---|
AU (1) | AU627949B2 (en) |
BR (1) | BR9005696A (en) |
GB (2) | GB8925515D0 (en) |
Cited By (6)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
FR2708198A1 (en) * | 1993-07-28 | 1995-02-03 | Dior Christian Parfums | Cosmetic or pharmaceutical composition, especially dermatological, containing an extract of Tephrosia, in particular Tephrosia purpurea. |
FR2762008A1 (en) * | 1997-04-15 | 1998-10-16 | Fabre Pierre Dermo Cosmetique | Deodorisation of Pongamia oil for use in cosmetics |
EP1217984B1 (en) * | 1999-10-08 | 2004-12-22 | Coty B.V. | Cosmetic preparation of active substances with a synergistically increased radical protection factor |
FR2886155A1 (en) * | 2005-05-27 | 2006-12-01 | Acorane Sarl | Use of Tephrosia purpurea extract for the preparation of a pharmaceutical or dermatological composition to prevent and/or treat stomatodynia |
FR3001150A1 (en) * | 2013-01-24 | 2014-07-25 | Jean-Noel Thorel | ALTERNATIVE PROTECTION SYSTEM AGAINST UV AND FREE RADICALS |
US10245220B2 (en) | 2015-07-22 | 2019-04-02 | Biosynthis | Process for pongamol enrichment of karanja oil |
Family Cites Families (1)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US5093351A (en) * | 1989-01-05 | 1992-03-03 | Du Pont Merck Pharmaceutical Company | Substituted indole, benzofuran and benzothiophene derivatives as 5-lipoxygenase inhibitors |
-
1989
- 1989-11-10 GB GB898925515A patent/GB8925515D0/en active Pending
-
1990
- 1990-11-06 GB GB9024116A patent/GB2237805B/en not_active Expired - Lifetime
- 1990-11-08 AU AU65908/90A patent/AU627949B2/en not_active Expired
- 1990-11-09 BR BR909005696A patent/BR9005696A/en unknown
Cited By (13)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
FR2708198A1 (en) * | 1993-07-28 | 1995-02-03 | Dior Christian Parfums | Cosmetic or pharmaceutical composition, especially dermatological, containing an extract of Tephrosia, in particular Tephrosia purpurea. |
WO1995003780A1 (en) * | 1993-07-28 | 1995-02-09 | Parfums Christian Dior | Cosmetic or pharmaceutical and particularly dermatological composition containing an extract of tephrosia, particularly tephrosia purpurea |
AU684532B2 (en) * | 1993-07-28 | 1997-12-18 | Parfums Christian Dior | Cosmetic or pharmaceutical and particularly dermatological composition containing an extract of tephrosia, particularly tephrosia purpurea |
FR2762008A1 (en) * | 1997-04-15 | 1998-10-16 | Fabre Pierre Dermo Cosmetique | Deodorisation of Pongamia oil for use in cosmetics |
EP1217984B1 (en) * | 1999-10-08 | 2004-12-22 | Coty B.V. | Cosmetic preparation of active substances with a synergistically increased radical protection factor |
AU778851B2 (en) * | 1999-10-08 | 2004-12-23 | Coty Bv | Cosmetic preparation of active substances with a synergistically increased radical protection factor |
US6989150B1 (en) | 1999-10-08 | 2006-01-24 | Coty B.V. | Cosmetic preparation of active substances with a synergistically increased radical protection factor |
FR2886155A1 (en) * | 2005-05-27 | 2006-12-01 | Acorane Sarl | Use of Tephrosia purpurea extract for the preparation of a pharmaceutical or dermatological composition to prevent and/or treat stomatodynia |
FR3001150A1 (en) * | 2013-01-24 | 2014-07-25 | Jean-Noel Thorel | ALTERNATIVE PROTECTION SYSTEM AGAINST UV AND FREE RADICALS |
WO2014114888A2 (en) | 2013-01-24 | 2014-07-31 | THOREL JEAN-NOëL | Alternative system for protection against uv radiation and free radicals |
WO2014114888A3 (en) * | 2013-01-24 | 2014-12-31 | THOREL JEAN-NOëL | Alternative system for protection against uv radiation and free radicals |
US10245220B2 (en) | 2015-07-22 | 2019-04-02 | Biosynthis | Process for pongamol enrichment of karanja oil |
EP3598999A1 (en) | 2015-07-22 | 2020-01-29 | Biosynthis | Method for enriching karanja oil |
Also Published As
Publication number | Publication date |
---|---|
GB8925515D0 (en) | 1989-12-28 |
AU627949B2 (en) | 1992-09-03 |
GB9024116D0 (en) | 1990-12-19 |
BR9005696A (en) | 1991-09-17 |
AU6590890A (en) | 1991-05-16 |
GB2237805B (en) | 1992-12-23 |
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Legal Events
Date | Code | Title | Description |
---|---|---|---|
732E | Amendments to the register in respect of changes of name or changes affecting rights (sect. 32/1977) | ||
PE20 | Patent expired after termination of 20 years |
Expiry date: 20101105 |