WO2005000866A1 - Cyclopentaperhydro-phenathrene 3-beta-carboxylic acid salts useful as emulsifier - Google Patents
Cyclopentaperhydro-phenathrene 3-beta-carboxylic acid salts useful as emulsifier Download PDFInfo
- Publication number
- WO2005000866A1 WO2005000866A1 PCT/EP2004/006615 EP2004006615W WO2005000866A1 WO 2005000866 A1 WO2005000866 A1 WO 2005000866A1 EP 2004006615 W EP2004006615 W EP 2004006615W WO 2005000866 A1 WO2005000866 A1 WO 2005000866A1
- Authority
- WO
- WIPO (PCT)
- Prior art keywords
- stigmast
- acid
- dien
- methyl
- reaction
- Prior art date
Links
- 0 CC(CC1)(CCC1O)C(CC*1C2CCC(*)C1)C2C#CC* Chemical compound CC(CC1)(CCC1O)C(CC*1C2CCC(*)C1)C2C#CC* 0.000 description 5
Classifications
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K8/00—Cosmetics or similar toiletry preparations
- A61K8/02—Cosmetics or similar toiletry preparations characterised by special physical form
- A61K8/04—Dispersions; Emulsions
- A61K8/06—Emulsions
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K8/00—Cosmetics or similar toiletry preparations
- A61K8/02—Cosmetics or similar toiletry preparations characterised by special physical form
- A61K8/04—Dispersions; Emulsions
- A61K8/06—Emulsions
- A61K8/062—Oil-in-water emulsions
-
- 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
- A61K8/63—Steroids; Derivatives thereof
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K9/00—Medicinal preparations characterised by special physical form
- A61K9/10—Dispersions; Emulsions
- A61K9/107—Emulsions ; Emulsion preconcentrates; Micelles
-
- 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
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07J—STEROIDS
- C07J9/00—Normal steroids containing carbon, hydrogen, halogen or oxygen substituted in position 17 beta by a chain of more than two carbon atoms, e.g. cholane, cholestane, coprostane
Definitions
- the present invention concerns new cyclopentaperhydrophenanthrene 3- ⁇ -carboxylic acid salts , suitable for the preparation of oil/water emulsions that are particularly stable and highly compatible with dermatological-cosmetic use.
- the invention also concerns the process for preparing these salts, the base emulsifier prepared with them, the oil/water emulsion obtained with this base emulsifier and the products for dermatological, cosmetic and pharmaceutical use formed with this emulsion.
- the field of the invention is that of the preparation of emulsions for use in cosmetics, pharmaceutics and the like (for example creams, cleansing milks, body-lotions, etc..) . These preparations set themselves apart for the coexistence of an aqueous phase and an oleous phase in a dispersion made stable with the use of emulsifiers.
- the preparation of conventional emulsifiers is distinguished in that it foresees the use of synthetic reactants which, by their very nature and by the formation of sub-products, give the end product undesired effects, like sensitisation of the skin and irritation.
- the main purpose of the present invention is that of providing a new emulsifier and the relative emulsion which, unlike conventional ones, offers better properties of compatibility with the skin, without therefore giving rise to undesired phenomena or harmful secondary effects.
- those obtained according to the invention offer the advantage of being highly compatible with dermatological and pharamaceutical use, due to the absence o,f formation of harmful secondary derivatives, a consequence of the natural origin of the raw material used.
- the invention shall now be described with reference to non- limiting- examples of cyclopentaperhydrophenathrene 3- ⁇ - carboxylic acid salts, of the process for preparing these salts, of the base emulsifier prepared with them, of the oil/water emulsion obtained with this base emulsifier and of the products for dermatological, cosmetic and pharmaceutical use, all according to the present invention.
- the starting product for preparing the salts of the invention consists of cyclopentaperhydrophenathrene 3- ⁇ -ols of natural origin (hereafter CPPF3 ⁇ ols) , preferably of plant origin (sitosterols) .
- CPPF3 ⁇ ols of animal origin like for example cholesterol and lanosterol, can also be used for the purposes of the invention.
- CPPF3 ⁇ ols of plant origin are used: ⁇ -sitosterol-stigmast-4- methyl-7, 24-dien-3- ⁇ -ol , ⁇ -sitosterol-stigmast-6-en-3- ⁇ -ol and ⁇ -sitosterol-stigmast-5-en-3- ⁇ -ol .
- CPPF3 ⁇ ols are subjected to semi-esterification reaction with cyclic anhydrides, in particular maleic anhydride, succinic anhydride and glutaric anhydride.
- the reaction is carried out in a mineral oil environment with protonic catalysis, at a temperature of about 70 °C, until the characteristic free acidity of each type of acid corresponding to the starting anhydride is reached.
- the carboxylic acid thus obtained is subjected to neutralisation reaction with nitrogen-substituted bases.
- bases consisting of triethanolamine, 2- aminomethylamino-1, 3-propanediol and arginine can be used.
- the product of the neutralisation reaction is a primary emulsifier consisting of CPPF3 ⁇ -carboxylic acid salt.
- a coemulsifier having thickening properties generally consisting of glyceride monoesters, in particular glycerylmonostearate, is added to the primary emulsifier described above.
- the base emulsifier of the invention is obtained by mixing at their melting points.
- emulsions can be in fluid or cream form, by addition to the base emulsifier of excipients and water. With such emulsions products for cosmetic use can be obtained in the form of creams or milks .
- the acid is obtained by reaction of the sitosterol corresponding with maleic anhydride, according to the following reaction scheme:
- the stigmast-4-methyl-7, 24-dien-3- ⁇ -semisuccinic acid of example 1 was made to react with 2-aminomethylamino-l, 3- propanediol, according to the following reaction scheme: C H, - C K - C H ⁇ OH NH OH i CH,MH,
- the stigmast-4-methyl-7, 24-dien-3- ⁇ -semimaleic acid of example 2 was made to react with 2-aminomethylamino-l, 3- propanediol, according to the following reaction scheme:
- a solution is prepared formed from 21g of dissolved soya sitosterols, at a temperature of 70 °C, in 20g of light Vaseline oil. 5g of maleic anhydride and 0.5g of methanesulfonic acid are added to the solution thus prepared. The solution is mixed for about Ih at 70°C. By cooling a yellow-coloured solid substance is obtained, corresponding to the_ semiester of sitosterol. This substance is used as such in a paraffinic mixture, to be neutralised with the selected base and • to thus constitute the emulsifier used in the cosmetic preparation. PREPARATION OF THE EMULSION A milk and a cream for cosmetic use were prepared with the emulsifier obtained in the previous example.
Landscapes
- Health & Medical Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- Chemical & Material Sciences (AREA)
- General Health & Medical Sciences (AREA)
- Public Health (AREA)
- Animal Behavior & Ethology (AREA)
- Veterinary Medicine (AREA)
- Epidemiology (AREA)
- Birds (AREA)
- Dispersion Chemistry (AREA)
- Organic Chemistry (AREA)
- Oil, Petroleum & Natural Gas (AREA)
- Medicinal Chemistry (AREA)
- Pharmacology & Pharmacy (AREA)
- Dermatology (AREA)
- Cosmetics (AREA)
- Steroid Compounds (AREA)
Applications Claiming Priority (2)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
IT001322A ITMI20031322A1 (it) | 2003-06-27 | 2003-06-27 | Sali degli acidi di ciclopentaperidrofenantrene 3-beta-carbossilici, procedimento per la preparazione di questi sali, emulsionante di base preparato con gli stessi, emulsione olio/acqua ottenuta con questo emulsionante di base e preparati per l'impie |
ITMI2003A001322 | 2003-06-27 |
Publications (1)
Publication Number | Publication Date |
---|---|
WO2005000866A1 true WO2005000866A1 (en) | 2005-01-06 |
Family
ID=30131318
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
PCT/EP2004/006615 WO2005000866A1 (en) | 2003-06-27 | 2004-06-18 | Cyclopentaperhydro-phenathrene 3-beta-carboxylic acid salts useful as emulsifier |
Country Status (2)
Country | Link |
---|---|
IT (1) | ITMI20031322A1 (it) |
WO (1) | WO2005000866A1 (it) |
Cited By (2)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US6734277B2 (en) | 2002-05-09 | 2004-05-11 | General Electric Company | Method of enhancing pit replication in optical disks |
WO2023147640A1 (en) * | 2022-02-07 | 2023-08-10 | GERVÁSIO ALVES DA SILVA, Társis | Preparation of novel triterpene alcohol derivatives with enhanced bioavailability for cancer, inflammation and pain treatment |
Citations (4)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
JPS58223436A (ja) * | 1982-02-10 | 1983-12-26 | Shiseido Co Ltd | 乳化組成物 |
WO1985004578A1 (en) * | 1984-04-12 | 1985-10-24 | The Liposome Company, Inc. | Steroidal liposomes |
EP0554897A2 (en) * | 1992-02-05 | 1993-08-11 | Kao Corporation | Novel sterol derivative, process for producing the same and dermatologic external preparation |
WO1999015547A1 (en) * | 1997-09-09 | 1999-04-01 | Raisio Benecol Ltd. | Use of organic acid esters in food products |
-
2003
- 2003-06-27 IT IT001322A patent/ITMI20031322A1/it unknown
-
2004
- 2004-06-18 WO PCT/EP2004/006615 patent/WO2005000866A1/en active Application Filing
Patent Citations (4)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
JPS58223436A (ja) * | 1982-02-10 | 1983-12-26 | Shiseido Co Ltd | 乳化組成物 |
WO1985004578A1 (en) * | 1984-04-12 | 1985-10-24 | The Liposome Company, Inc. | Steroidal liposomes |
EP0554897A2 (en) * | 1992-02-05 | 1993-08-11 | Kao Corporation | Novel sterol derivative, process for producing the same and dermatologic external preparation |
WO1999015547A1 (en) * | 1997-09-09 | 1999-04-01 | Raisio Benecol Ltd. | Use of organic acid esters in food products |
Non-Patent Citations (1)
Title |
---|
PATENT ABSTRACTS OF JAPAN vol. 0080, no. 71 (C - 217) 3 April 1984 (1984-04-03) * |
Cited By (2)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US6734277B2 (en) | 2002-05-09 | 2004-05-11 | General Electric Company | Method of enhancing pit replication in optical disks |
WO2023147640A1 (en) * | 2022-02-07 | 2023-08-10 | GERVÁSIO ALVES DA SILVA, Társis | Preparation of novel triterpene alcohol derivatives with enhanced bioavailability for cancer, inflammation and pain treatment |
Also Published As
Publication number | Publication date |
---|---|
ITMI20031322A1 (it) | 2004-12-28 |
ITMI20031322A0 (it) | 2003-06-27 |
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