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 PDFInfo
- 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
- Authority
- WO
- WIPO (PCT)
- Prior art keywords
- acetyl
- aminoacyl
- glycerol
- ester
- process according
- Prior art date
Links
- 239000004094 surface-active agent Substances 0.000 title claims abstract description 19
- 150000001413 amino acids Chemical class 0.000 title claims abstract description 18
- 238000002360 preparation method Methods 0.000 title claims abstract description 12
- 150000002148 esters Chemical class 0.000 title claims description 12
- 150000001875 compounds Chemical class 0.000 claims abstract description 17
- 238000004128 high performance liquid chromatography Methods 0.000 claims abstract description 6
- 239000004599 antimicrobial Substances 0.000 claims abstract description 3
- 230000000694 effects Effects 0.000 claims abstract description 3
- 238000000746 purification Methods 0.000 claims abstract description 3
- 125000005456 glyceride group Chemical group 0.000 claims abstract 3
- PEDCQBHIVMGVHV-UHFFFAOYSA-N glycerol Substances OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 claims description 60
- 238000000034 method Methods 0.000 claims description 28
- 229940024606 amino acid Drugs 0.000 claims description 20
- 235000001014 amino acid Nutrition 0.000 claims description 19
- 230000015572 biosynthetic process Effects 0.000 claims description 13
- 229920006395 saturated elastomer Polymers 0.000 claims description 10
- 239000000126 substance Substances 0.000 claims description 10
- 108090000790 Enzymes Proteins 0.000 claims description 9
- 102000004190 Enzymes Human genes 0.000 claims description 9
- -1 N-acetyl amino Chemical class 0.000 claims description 8
- 125000004432 carbon atom Chemical group C* 0.000 claims description 8
- 230000002255 enzymatic effect Effects 0.000 claims description 8
- 239000000203 mixture Substances 0.000 claims description 8
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 8
- 238000005917 acylation reaction Methods 0.000 claims description 7
- 235000014113 dietary fatty acids Nutrition 0.000 claims description 7
- 229930195729 fatty acid Natural products 0.000 claims description 7
- 239000000194 fatty acid Substances 0.000 claims description 7
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 claims description 6
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 claims description 6
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 6
- RAXXELZNTBOGNW-UHFFFAOYSA-N imidazole Natural products C1=CNC=N1 RAXXELZNTBOGNW-UHFFFAOYSA-N 0.000 claims description 6
- 108090001060 Lipase Proteins 0.000 claims description 5
- 239000004367 Lipase Substances 0.000 claims description 5
- 102000004882 Lipase Human genes 0.000 claims description 5
- 125000002777 acetyl group Chemical group [H]C([H])([H])C(*)=O 0.000 claims description 5
- 238000006243 chemical reaction Methods 0.000 claims description 5
- 150000004665 fatty acids Chemical class 0.000 claims description 5
- 235000019421 lipase Nutrition 0.000 claims description 5
- 239000002904 solvent Substances 0.000 claims description 5
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims description 4
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims description 3
- 102000035195 Peptidases Human genes 0.000 claims description 3
- 108091005804 Peptidases Proteins 0.000 claims description 3
- 239000004365 Protease Substances 0.000 claims description 3
- 230000010933 acylation Effects 0.000 claims description 3
- 230000003301 hydrolyzing effect Effects 0.000 claims description 3
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 claims description 3
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 2
- 150000001408 amides Chemical class 0.000 claims description 2
- 125000003118 aryl group Chemical group 0.000 claims description 2
- 229910052739 hydrogen Inorganic materials 0.000 claims description 2
- 239000001257 hydrogen Substances 0.000 claims description 2
- 125000006289 hydroxybenzyl group Chemical group 0.000 claims description 2
- 125000006239 protecting group Chemical group 0.000 claims description 2
- 239000007858 starting material Substances 0.000 claims description 2
- ZDXPYRJPNDTMRX-VKHMYHEASA-N L-glutamine Chemical compound OC(=O)[C@@H](N)CCC(N)=O ZDXPYRJPNDTMRX-VKHMYHEASA-N 0.000 claims 2
- 238000001311 chemical methods and process Methods 0.000 claims 2
- 238000009833 condensation Methods 0.000 claims 2
- 230000005494 condensation Effects 0.000 claims 2
- ZDXPYRJPNDTMRX-UHFFFAOYSA-N glutamine Natural products OC(=O)C(N)CCC(N)=O ZDXPYRJPNDTMRX-UHFFFAOYSA-N 0.000 claims 2
- DCXYFEDJOCDNAF-UHFFFAOYSA-N Asparagine Natural products OC(=O)C(N)CC(N)=O DCXYFEDJOCDNAF-UHFFFAOYSA-N 0.000 claims 1
- DCXYFEDJOCDNAF-REOHCLBHSA-N L-asparagine Chemical compound OC(=O)[C@@H](N)CC(N)=O DCXYFEDJOCDNAF-REOHCLBHSA-N 0.000 claims 1
- HNDVDQJCIGZPNO-YFKPBYRVSA-N L-histidine Chemical compound OC(=O)[C@@H](N)CC1=CN=CN1 HNDVDQJCIGZPNO-YFKPBYRVSA-N 0.000 claims 1
- OUYCCCASQSFEME-QMMMGPOBSA-N L-tyrosine Chemical compound OC(=O)[C@@H](N)CC1=CC=C(O)C=C1 OUYCCCASQSFEME-QMMMGPOBSA-N 0.000 claims 1
- 108010048733 Lipozyme Proteins 0.000 claims 1
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 claims 1
- 238000004458 analytical method Methods 0.000 claims 1
- 229960001230 asparagine Drugs 0.000 claims 1
- 235000009582 asparagine Nutrition 0.000 claims 1
- 239000011942 biocatalyst Substances 0.000 claims 1
- 238000006555 catalytic reaction Methods 0.000 claims 1
- 239000007809 chemical reaction catalyst Substances 0.000 claims 1
- 239000003480 eluent Substances 0.000 claims 1
- HNDVDQJCIGZPNO-UHFFFAOYSA-N histidine Natural products OC(=O)C(N)CC1=CN=CN1 HNDVDQJCIGZPNO-UHFFFAOYSA-N 0.000 claims 1
- FCCDDURTIIUXBY-UHFFFAOYSA-N lipoamide Chemical compound NC(=O)CCCCC1CCSS1 FCCDDURTIIUXBY-UHFFFAOYSA-N 0.000 claims 1
- 238000002156 mixing Methods 0.000 claims 1
- 125000005480 straight-chain fatty acid group Chemical group 0.000 claims 1
- OUYCCCASQSFEME-UHFFFAOYSA-N tyrosine Natural products OC(=O)C(N)CC1=CC=C(O)C=C1 OUYCCCASQSFEME-UHFFFAOYSA-N 0.000 claims 1
- 239000007788 liquid Substances 0.000 abstract description 6
- 238000002425 crystallisation Methods 0.000 abstract description 3
- 230000008025 crystallization Effects 0.000 abstract description 3
- 239000007787 solid Substances 0.000 abstract description 3
- 238000000605 extraction Methods 0.000 abstract description 2
- 238000004255 ion exchange chromatography Methods 0.000 abstract description 2
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 9
- 238000003786 synthesis reaction Methods 0.000 description 9
- 239000000047 product Substances 0.000 description 8
- 239000003054 catalyst Substances 0.000 description 7
- 239000002609 medium Substances 0.000 description 6
- 239000012429 reaction media Substances 0.000 description 4
- 239000000084 colloidal system Substances 0.000 description 3
- 238000005886 esterification reaction Methods 0.000 description 3
- 235000013305 food Nutrition 0.000 description 3
- 238000003756 stirring Methods 0.000 description 3
- VHYFNPMBLIVWCW-UHFFFAOYSA-N 4-Dimethylaminopyridine Chemical compound CN(C)C1=CC=NC=C1 VHYFNPMBLIVWCW-UHFFFAOYSA-N 0.000 description 2
- 239000002253 acid Substances 0.000 description 2
- 150000007513 acids Chemical class 0.000 description 2
- 239000003795 chemical substances by application Substances 0.000 description 2
- KRKNYBCHXYNGOX-UHFFFAOYSA-N citric acid Substances OC(=O)CC(O)(C(O)=O)CC(O)=O KRKNYBCHXYNGOX-UHFFFAOYSA-N 0.000 description 2
- POULHZVOKOAJMA-UHFFFAOYSA-N dodecanoic acid Chemical compound CCCCCCCCCCCC(O)=O POULHZVOKOAJMA-UHFFFAOYSA-N 0.000 description 2
- 238000010828 elution Methods 0.000 description 2
- 239000003995 emulsifying agent Substances 0.000 description 2
- 150000002313 glycerolipids Chemical class 0.000 description 2
- 230000002209 hydrophobic effect Effects 0.000 description 2
- 239000000543 intermediate Substances 0.000 description 2
- JVTAAEKCZFNVCJ-UHFFFAOYSA-N lactic acid Chemical compound CC(O)C(O)=O JVTAAEKCZFNVCJ-UHFFFAOYSA-N 0.000 description 2
- 150000002632 lipids Chemical class 0.000 description 2
- 238000004811 liquid chromatography Methods 0.000 description 2
- VNWKTOKETHGBQD-UHFFFAOYSA-N methane Chemical compound C VNWKTOKETHGBQD-UHFFFAOYSA-N 0.000 description 2
- 238000002953 preparative HPLC Methods 0.000 description 2
- 239000011541 reaction mixture Substances 0.000 description 2
- CNDHHGUSRIZDSL-UHFFFAOYSA-N 1-chlorooctane Chemical compound CCCCCCCCCl CNDHHGUSRIZDSL-UHFFFAOYSA-N 0.000 description 1
- 229960000549 4-dimethylaminophenol Drugs 0.000 description 1
- PXRKCOCTEMYUEG-UHFFFAOYSA-N 5-aminoisoindole-1,3-dione Chemical compound NC1=CC=C2C(=O)NC(=O)C2=C1 PXRKCOCTEMYUEG-UHFFFAOYSA-N 0.000 description 1
- 239000004475 Arginine Substances 0.000 description 1
- CKLJMWTZIZZHCS-REOHCLBHSA-N L-aspartic acid Chemical compound OC(=O)[C@@H](N)CC(O)=O CKLJMWTZIZZHCS-REOHCLBHSA-N 0.000 description 1
- 239000005639 Lauric acid Substances 0.000 description 1
- 238000003820 Medium-pressure liquid chromatography Methods 0.000 description 1
- OTCCIMWXFLJLIA-BYPYZUCNSA-N N-acetyl-L-aspartic acid Chemical compound CC(=O)N[C@H](C(O)=O)CC(O)=O OTCCIMWXFLJLIA-BYPYZUCNSA-N 0.000 description 1
- 238000005481 NMR spectroscopy Methods 0.000 description 1
- 108010084311 Novozyme 435 Proteins 0.000 description 1
- 238000004220 aggregation Methods 0.000 description 1
- 125000003158 alcohol group Chemical group 0.000 description 1
- 125000000217 alkyl group Chemical group 0.000 description 1
- 125000000266 alpha-aminoacyl group Chemical group 0.000 description 1
- 150000003862 amino acid derivatives Chemical class 0.000 description 1
- 230000000845 anti-microbial effect Effects 0.000 description 1
- 239000002216 antistatic agent Substances 0.000 description 1
- 239000012736 aqueous medium Substances 0.000 description 1
- ODKSFYDXXFIFQN-UHFFFAOYSA-N arginine Natural products OC(=O)C(N)CCCNC(N)=N ODKSFYDXXFIFQN-UHFFFAOYSA-N 0.000 description 1
- 229960005261 aspartic acid Drugs 0.000 description 1
- 235000003704 aspartic acid Nutrition 0.000 description 1
- 125000001584 benzyloxycarbonyl group Chemical group C(=O)(OCC1=CC=CC=C1)* 0.000 description 1
- OQFSQFPPLPISGP-UHFFFAOYSA-N beta-carboxyaspartic acid Natural products OC(=O)C(N)C(C(O)=O)C(O)=O OQFSQFPPLPISGP-UHFFFAOYSA-N 0.000 description 1
- 229910052799 carbon Inorganic materials 0.000 description 1
- 230000003197 catalytic effect Effects 0.000 description 1
- 125000002091 cationic group Chemical group 0.000 description 1
- 238000004587 chromatography analysis Methods 0.000 description 1
- 238000004140 cleaning Methods 0.000 description 1
- 238000006482 condensation reaction Methods 0.000 description 1
- 239000002537 cosmetic Substances 0.000 description 1
- 239000003814 drug Substances 0.000 description 1
- 229940079593 drug Drugs 0.000 description 1
- 239000000839 emulsion Substances 0.000 description 1
- 238000005516 engineering process Methods 0.000 description 1
- 230000007613 environmental effect Effects 0.000 description 1
- 230000032050 esterification Effects 0.000 description 1
- 238000001704 evaporation Methods 0.000 description 1
- 230000008020 evaporation Effects 0.000 description 1
- 239000000835 fiber Substances 0.000 description 1
- 239000000706 filtrate Substances 0.000 description 1
- 239000012467 final product Substances 0.000 description 1
- 235000003084 food emulsifier Nutrition 0.000 description 1
- 238000009472 formulation Methods 0.000 description 1
- 235000021588 free fatty acids Nutrition 0.000 description 1
- 238000004108 freeze drying Methods 0.000 description 1
- 125000005908 glyceryl ester group Chemical group 0.000 description 1
- 238000000265 homogenisation Methods 0.000 description 1
- 239000000976 ink Substances 0.000 description 1
- 239000004310 lactic acid Substances 0.000 description 1
- 238000003760 magnetic stirring Methods 0.000 description 1
- 238000004949 mass spectrometry Methods 0.000 description 1
- 239000012528 membrane Substances 0.000 description 1
- 150000002759 monoacylglycerols Chemical class 0.000 description 1
- PSHKMPUSSFXUIA-UHFFFAOYSA-N n,n-dimethylpyridin-2-amine Chemical compound CN(C)C1=CC=CC=N1 PSHKMPUSSFXUIA-UHFFFAOYSA-N 0.000 description 1
- 231100000252 nontoxic Toxicity 0.000 description 1
- 230000003000 nontoxic effect Effects 0.000 description 1
- 150000007524 organic acids Chemical class 0.000 description 1
- 235000005985 organic acids Nutrition 0.000 description 1
- 150000007530 organic bases Chemical group 0.000 description 1
- 230000008520 organization Effects 0.000 description 1
- 239000003973 paint Substances 0.000 description 1
- 238000010647 peptide synthesis reaction Methods 0.000 description 1
- UYWQUFXKFGHYNT-UHFFFAOYSA-N phenylmethyl ester of formic acid Natural products O=COCC1=CC=CC=C1 UYWQUFXKFGHYNT-UHFFFAOYSA-N 0.000 description 1
- 150000003904 phospholipids Chemical class 0.000 description 1
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 description 1
- 125000001453 quaternary ammonium group Chemical group 0.000 description 1
- 239000002994 raw material Substances 0.000 description 1
- 238000010517 secondary reaction Methods 0.000 description 1
- 238000000638 solvent extraction Methods 0.000 description 1
- 238000001179 sorption measurement Methods 0.000 description 1
- 150000003626 triacylglycerols Chemical class 0.000 description 1
- 239000012610 weak anion exchange resin Substances 0.000 description 1
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)
- Pharmacology & Pharmacy (AREA)
- General Health & Medical Sciences (AREA)
- Wood Science & Technology (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Veterinary Medicine (AREA)
- Medicinal Chemistry (AREA)
- Engineering & Computer Science (AREA)
- Epidemiology (AREA)
- Animal Behavior & Ethology (AREA)
- Oil, Petroleum & Natural Gas (AREA)
- Public Health (AREA)
- Emergency Medicine (AREA)
- Dispersion Chemistry (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Preparation Of Compounds By Using Micro-Organisms (AREA)
- Mattresses And Other Support Structures For Chairs And Beds (AREA)
- Invalid Beds And Related Equipment (AREA)
Abstract
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 |
---|---|---|---|
ES200000318U ES1045340Y (es) | 2000-02-11 | 2000-02-11 | Cuña elevadora para camas de accionamiento neumatico. |
ESP200000318 | 2000-02-11 |
Publications (1)
Publication Number | Publication Date |
---|---|
WO2001058849A1 true WO2001058849A1 (fr) | 2001-08-16 |
Family
ID=8492263
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
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)
Country | Link |
---|---|
ES (1) | ES1045340Y (fr) |
WO (1) | WO2001058849A1 (fr) |
Cited By (1)
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)
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. |
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2000
- 2000-02-11 ES ES200000318U patent/ES1045340Y/es not_active Expired - Fee Related
-
2001
- 2001-02-08 WO PCT/ES2001/000040 patent/WO2001058849A1/fr active Application Filing
Patent Citations (2)
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 |
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