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WO2001058849A1 - TENSIO-ACTIFS DERIVES D'AMINOACIDES DU TYPE 1-O-Nα-ACETYL-L-AMINOACYL ESTER 3-O-MONOACYL GLYCERIDES ET 1-O-Nα-ACETYL L-AMINOACYL ESTER 2,3-O-DIACYL GLYCERIDES ET LEUR PREPARATION - Google Patents

TENSIO-ACTIFS DERIVES D'AMINOACIDES DU TYPE 1-O-Nα-ACETYL-L-AMINOACYL ESTER 3-O-MONOACYL GLYCERIDES ET 1-O-Nα-ACETYL L-AMINOACYL ESTER 2,3-O-DIACYL GLYCERIDES ET LEUR PREPARATION Download PDF

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Publication number
WO2001058849A1
WO2001058849A1 PCT/ES2001/000040 ES0100040W WO0158849A1 WO 2001058849 A1 WO2001058849 A1 WO 2001058849A1 ES 0100040 W ES0100040 W ES 0100040W WO 0158849 A1 WO0158849 A1 WO 0158849A1
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WO
WIPO (PCT)
Prior art keywords
acetyl
aminoacyl
glycerol
ester
process according
Prior art date
Application number
PCT/ES2001/000040
Other languages
English (en)
Spanish (es)
Inventor
Pere Clapes Saborit
Carmen Moran Badenas
Mª Lourdes PEREZ MUÑOZ
Mª Rosa INFANTE MARTINEZ-PARDO
Original Assignee
Consejo Superior De Investigaciones Cientificas
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 Consejo Superior De Investigaciones Cientificas filed Critical Consejo Superior De Investigaciones Cientificas
Priority to AU2001231770A priority Critical patent/AU2001231770A1/en
Publication of WO2001058849A1 publication Critical patent/WO2001058849A1/fr

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Classifications

    • 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
    • C11D3/48—Medical, disinfecting agents, disinfecting, antibacterial, germicidal or antimicrobial compositions
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K31/00—Medicinal preparations containing organic active ingredients
    • A61K31/21—Esters, e.g. nitroglycerine, selenocyanates
    • A61K31/215—Esters, e.g. nitroglycerine, selenocyanates of carboxylic acids
    • A61K31/22—Esters, e.g. nitroglycerine, selenocyanates of carboxylic acids of acyclic acids, e.g. pravastatin
    • A61K31/223—Esters, e.g. nitroglycerine, selenocyanates of carboxylic acids of acyclic acids, e.g. pravastatin of alpha-aminoacids
    • 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
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C233/00—Carboxylic acid amides
    • C07C233/01—Carboxylic acid amides having carbon atoms of carboxamide groups bound to hydrogen atoms or to acyclic carbon atoms
    • C07C233/45—Carboxylic acid amides having carbon atoms of carboxamide groups bound to hydrogen atoms or to acyclic carbon atoms having the nitrogen atom of at least one of the carboxamide groups bound to a carbon atom of a hydrocarbon radical substituted by carboxyl groups
    • C07C233/46—Carboxylic acid amides having carbon atoms of carboxamide groups bound to hydrogen atoms or to acyclic carbon atoms having the nitrogen atom of at least one of the carboxamide groups bound to a carbon atom of a hydrocarbon radical substituted by carboxyl groups with the substituted hydrocarbon radical bound to the nitrogen atom of the carboxamide group by an acyclic carbon atom
    • C07C233/47—Carboxylic acid amides having carbon atoms of carboxamide groups bound to hydrogen atoms or to acyclic carbon atoms having the nitrogen atom of at least one of the carboxamide groups bound to a carbon atom of a hydrocarbon radical substituted by carboxyl groups with the substituted hydrocarbon radical bound to the nitrogen atom of the carboxamide group by an acyclic carbon atom having the carbon atom of the carboxamide group bound to a hydrogen atom or to a carbon atom of an acyclic saturated carbon skeleton
    • 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
    • C11D1/00—Detergent compositions based essentially on surface-active compounds; Use of these compounds as a detergent
    • C11D1/02—Anionic compounds
    • C11D1/04—Carboxylic acids or salts thereof
    • C11D1/10—Amino carboxylic acids; Imino carboxylic acids; Fatty acid condensates thereof

Definitions

  • Surfactant compounds are amphiphilic organic products composed of a hydrophilic part (-COO ⁇ , -S0 3 , -O-, quaternary ammonium) and a hydrophobic (a fatty chain of 8-18 carbon atoms). These products have an extraordinary interest in their wide and versatile application in preparations with a strong impact in our immediate surroundings (food emulsifiers, cleaning and personal hygiene products, drugs, cosmetics, paints, inks, fiber antistatic agents, etc.). Although today it can be considered that the industrial sectors have adequate surfactants for the functions they must perform, current European regulations require the search and study of new alternatives in which the following requirements converge: safety, multifunctionality, efficiency and competitiveness
  • the object of the present invention is the synthesis of a new family of amino acid-derived surfactants with a mimetic structure to mono acyl glycerides and diacylglycerides.
  • These surfactants consist of a central glycerol skeleton that joins the hydrophobic part formed by one or two fatty chains of variable length to the hydrophilic part formed by an amino acid.
  • These new structures have advantages over the mono and diacylglycerides described above: a) the introduction of an amino acid as a polar part of the surfactant increases the solubility in aqueous medium and b) compounds with antimicrobial activity can be obtained depending on the amino acid present
  • Amino acid derived surfactants are compounds of high interest due to their multifunctionality and safety (Takehara, M. 1989, Colloids and Surfaces, 38: 149; Selve, C, Mansuy, L., Allouch, M., 1992, J Chem. Res. 22: 401). These characteristics have been responsible for the synthesis and study of properties of a wide variety of surfactants of this type, ionic, cationic, non-ionic and amphoteric in nature in recent years (Takehara, M. 1989, Colloids and Surfaces, 38: 149; Sagawa, K., Yokota, H., Ueno, I., Miyosi, T., Takehara, M., XIV IFSCC Congress, 1986).
  • lipase type enzymes In relation to the acylation of glycerol hydroxyl groups, the use of lipase type enzymes has been described (Valivety, R., Gill, IS, Vulfson, EN (1998) J. Surf. Deterg. L 177-185) as catalysts of the esterification reaction.
  • the main novelties of the present invention are the combination in the same molecule of mono-type surfactants and diacylglycerides and surfactants derived from amino acids with minimal protection as well as the use of enzymes as substitutes for conventional chemical catalysts. DESCRIPTION OF THE INVENTION
  • the present invention relates to a new family of amino acid derived surfactants with a glycerol skeleton esterified by one or two fatty acid chains as well as to the methods of synthesis of these compounds.
  • the structural formula of these compounds is indicated (I).
  • Ri is an acetyl group.
  • R may be an optionally substituted, saturated or unsaturated linear or branched chain or an optionally substituted aromatic group.
  • R 3 and ⁇ can be a hydrogen or a preferably long saturated or unsaturated linear chain.
  • X can be: Br “ , Cl “ , HSO 4 " , CH 3 COO “ , CF 3 COO “ , Na + , K +
  • R is preferably a group: amide, hydroxybenzyl, imidazole and carboxyl.
  • R 3 and Rj can be selected from a group of linear chains of 8, 9,10, 12, 14,16 and 18 pure saturated or unsaturated carbon atoms or mixtures thereof.
  • the starting materials can be:
  • the number of alkyl chains (lo 2), the degree of unsaturation, the length thereof and the amino acid present are varied in the molecules which gives rise to compounds with a different behavior in the biological and physicochemical properties of adsorption and self-aggregation . Due to the origin of renewable and safe raw materials, these compounds are expected to be degradable and non-toxic both from a biological and environmental point of view.
  • the use of the acetyl group as a protective group of the amino function makes it possible to avoid possible secondary reactions of the Maillard type, in food applications, without altering the biocompatible nature of the final products obtained.
  • Enzymatic procedure the synthesis via enzyme has been carried out in two stages: a) Condensation reaction of glycerol and the free or esterified carboxyl group of N ⁇ -acetyl-L-amino acid, using hydrolytic enzymes, proteases type catalysts and lipases, in a medium in the absence of solvent and with low aqueous content. b) Acylation reaction of the OOaa (Ac) free alcohol groups with free fatty acids or esters of these acids, using as lipase catalysts. The reaction takes place in a medium in the absence of solvent and with a low aqueous content.
  • the present invention relates to novel surfactant compounds derived from mono and diacylglyceride type amino acids designed to act as surface and antimicrobial agents.
  • the variations in activity will be a function of the number of fatty chains, their length and the amino acid present in the structure.

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  • Chemical & Material Sciences (AREA)
  • Health & Medical Sciences (AREA)
  • Organic Chemistry (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • Epidemiology (AREA)
  • Oil, Petroleum & Natural Gas (AREA)
  • Medicinal Chemistry (AREA)
  • Animal Behavior & Ethology (AREA)
  • General Health & Medical Sciences (AREA)
  • Public Health (AREA)
  • Veterinary Medicine (AREA)
  • Engineering & Computer Science (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Pharmacology & Pharmacy (AREA)
  • Wood Science & Technology (AREA)
  • Dispersion Chemistry (AREA)
  • Emergency Medicine (AREA)
  • Preparation Of Compounds By Using Micro-Organisms (AREA)
  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
  • Mattresses And Other Support Structures For Chairs And Beds (AREA)
  • Invalid Beds And Related Equipment (AREA)

Abstract

La présente invention concerne de nouveaux composés tensio-actifs dérivés d'aminoacides du type mono et diacylglicéride, représentés par la formule générale (I) et conçus pour agir en tant qu'agents de surface à activité antimicrobienne. Les variations d'activité varieront en fonction du nombre de chaînes grasses, de leur longueur et de l'aminoacide présent dans la structure. La purification des produits intermédiaires et finaux s'obtient par extractions liquide-liquide, liquide-solide, par cristallisations, et par chromatographie par échange d'ions et CLHP préparative.
PCT/ES2001/000040 2000-02-11 2001-02-08 TENSIO-ACTIFS DERIVES D'AMINOACIDES DU TYPE 1-O-Nα-ACETYL-L-AMINOACYL ESTER 3-O-MONOACYL GLYCERIDES ET 1-O-Nα-ACETYL L-AMINOACYL ESTER 2,3-O-DIACYL GLYCERIDES ET LEUR PREPARATION WO2001058849A1 (fr)

Priority Applications (1)

Application Number Priority Date Filing Date Title
AU2001231770A AU2001231770A1 (en) 2000-02-11 2001-02-08 Surface active agents derived from 1-o-nalpha-acetyl-l-aminoacyl ester 3-o-monoacyl glycerides and 1-o-nalpha-acetyl l-aminoacyl ester 2,3-o-diacyl glycerides type amino acids and the preparation thereof

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
ESP200000318 2000-02-11
ES200000318U ES1045340Y (es) 2000-02-11 2000-02-11 Cuña elevadora para camas de accionamiento neumatico.

Publications (1)

Publication Number Publication Date
WO2001058849A1 true WO2001058849A1 (fr) 2001-08-16

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PCT/ES2001/000040 WO2001058849A1 (fr) 2000-02-11 2001-02-08 TENSIO-ACTIFS DERIVES D'AMINOACIDES DU TYPE 1-O-Nα-ACETYL-L-AMINOACYL ESTER 3-O-MONOACYL GLYCERIDES ET 1-O-Nα-ACETYL L-AMINOACYL ESTER 2,3-O-DIACYL GLYCERIDES ET LEUR PREPARATION

Country Status (2)

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ES (1) ES1045340Y (fr)
WO (1) WO2001058849A1 (fr)

Cited By (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO2003070735A3 (fr) * 2002-02-19 2004-03-25 Novosom Ag Elements permettant la preparation de liposomes amphoteres

Citations (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO1996021642A1 (fr) * 1995-01-10 1996-07-18 Laboratorios Miret, S.A. Procede de synthese de tensioactifs cationiques derives de la condensation d'acides gras avec des aminoacides dibasiques esterifies, et leur application en tant qu'agents antimicrobiens
ES2130980A1 (es) * 1997-03-10 1999-07-01 Consejo Superior Investigacion Procedimiento enzimatico para la preparacion de lipoaminoacidos del tipo alquil amidas y esteres.

Patent Citations (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO1996021642A1 (fr) * 1995-01-10 1996-07-18 Laboratorios Miret, S.A. Procede de synthese de tensioactifs cationiques derives de la condensation d'acides gras avec des aminoacides dibasiques esterifies, et leur application en tant qu'agents antimicrobiens
ES2130980A1 (es) * 1997-03-10 1999-07-01 Consejo Superior Investigacion Procedimiento enzimatico para la preparacion de lipoaminoacidos del tipo alquil amidas y esteres.

Non-Patent Citations (1)

* Cited by examiner, † Cited by third party
Title
R. VALIVETY ET AL.: "Chemo-enzymic synthesis of amino-acid based surfactants", JOURNAL AMERICAN OIL CHEM. SOC., vol. 74, no. 7, 1997, pages 879 - 886 *

Cited By (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO2003070735A3 (fr) * 2002-02-19 2004-03-25 Novosom Ag Elements permettant la preparation de liposomes amphoteres

Also Published As

Publication number Publication date
ES1045340Y (es) 2001-02-16
ES1045340U (es) 2000-08-16

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