FR2503151A1 - Compsns. contg. N-butyryl alpha-aminoacid(s) - for cosmetic, hygienic, therapeutic or agricultural use - Google Patents

Compsns. contg. N-butyryl alpha-aminoacid(s) - for cosmetic, hygienic, therapeutic or agricultural use Download PDF

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Publication number
FR2503151A1
FR2503151A1 FR8106592A FR8106592A FR2503151A1 FR 2503151 A1 FR2503151 A1 FR 2503151A1 FR 8106592 A FR8106592 A FR 8106592A FR 8106592 A FR8106592 A FR 8106592A FR 2503151 A1 FR2503151 A1 FR 2503151A1
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acid
contain
compsns
butyryl
aminoacid
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FR2503151B1 (en
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Priority to FR8106592A priority Critical patent/FR2503151A1/en
Priority to GB8208378A priority patent/GB2097256B/en
Priority to DE3212448A priority patent/DE3212448C2/en
Priority to JP5399982A priority patent/JPS57183703A/en
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Classifications

    • 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
    • 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
    • A61K8/40—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds containing nitrogen
    • A61K8/44—Aminocarboxylic acids or derivatives thereof, e.g. aminocarboxylic acids containing sulfur; Salts; Esters or N-acylated derivatives thereof
    • A61K8/447—Aminocarboxylic acids or derivatives thereof, e.g. aminocarboxylic acids containing sulfur; Salts; Esters or N-acylated derivatives thereof containing sulfur
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61Q—SPECIFIC USE OF COSMETICS OR SIMILAR TOILETRY PREPARATIONS
    • A61Q3/00—Manicure or pedicure preparations
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61Q—SPECIFIC USE OF COSMETICS OR SIMILAR TOILETRY PREPARATIONS
    • A61Q5/00—Preparations for care of the hair

Abstract

A compsn. for cosmetic, hygienic, therapeutic or agricultural use contains as active ingredient at least one N-butyryl alpha-aminoacid or salt of the acid. The N-butyryl cpds. are prepd. from the aminoacids and butyric anhydride. They are generally soluble in a wide variety of polar and non-polar solvents. An aminoacid mixt. obtd. by the complete hydrolysis of a protein may be N-butyrylated. Compsns. pref. contain 0.1-5wt.% of active ingredient. Examples of the use of the compsns. are as follows (1) a cream for skin care may contain butyrylhydroxyproline, butyrylproline, butyrylcystine, butyrylglycine, butyrylcollagenic acid, butyrylcaseinic acid and/or butyrylkeratinic acid; (2) a lotion for nail care may contain butyrylcystine or butyrylmethionine; (3) a toothpaste may contain calcium butyrylcollagenate; (4) compsns. for the agricultural treatment of seeds and roots may contain butyrylproline, copper or zinc butyrylproline, butyrylmethionine, butyrylcystine, butyrylkeratinic acid, copper butyrylkeratinate or copper butyrylcollagenate, and (5) antalgic compsns. may contain butyrylhydroxyproline.

Description

La présente invention concerne de nouveaux derivés d'acides amint soufrés,caractérisés en ce qu'un hydrogène de la fonction amine esremplacé par une chaine grasse,essentiellement butyrique,conduisan ainsi à une structure lipoaminoacide. On entend par acidesaminés soufrés,les structures comportant une fonction carboxylique et une fonction amine,en position alpha;d'origines protéiniques ou non protéiniques,ainsi qu'or ou plusieurs atomes de soufre situés à n': porte quel emplacement dans la molécule. The present invention relates to new sulfur amint acid derivatives, characterized in that a hydrogen of the amine function is replaced by a fatty chain, essentially butyric, thus leading to a lipoamino acid structure. The term “sulfur-containing amino acids” is intended to mean the structures comprising a carboxylic function and an amine function, in the alpha position; of proteinic or non-proteinic origins, as well as gold or more sulfur atoms located at any location in the molecule.

L'acide butyrique étant le premier représentant de la série gravi et le seul hydrosoluble; son acylation aux acides aminés cités,con contrairement aux autres lipoaminoacides connus,à une structure hydrosoluble. Butyric acid being the first representative of the gravitated series and the only water-soluble; its acylation with the cited amino acids, unlike other known lipoamino acids, has a water-soluble structure.

Comparativement aux autres structures lipoaminoacides soufrées comportant des chaines grasses contenant plus de cinq atomes de carbone,les dérivés butyryls présentent les avantages suivants:
I-De comporter une teneur plus élevée d'acide aminé dans la molSzi et,,par voie de conséquence,d'augmenter sensiblement leur activité, 2-D'ètre doué d'un pouvoir de pénétration cutanée plus élevé em ra de la nature de la structure et de l'hydrosolubilité. Compared to other sulfur lipoamino acid structures comprising fatty chains containing more than five carbon atoms, butyryl derivatives have the following advantages:
I-To include a higher content of amino acid in the molSzi and ,, consequently, to significantly increase their activity, 2-To be endowed with a higher skin penetrating power em ra of nature structure and water solubility.

3-D'ètre doués d'un pouvoir acidifiant de nature strictement biolo que, sensiblement superieur.3-To be endowed with an acidifying power of a strictly organic nature that, appreciably superior.

4-De pouvoir conduirà des résultats d'efficacité,identiques aux lipoaminoacides comportant plus de cinq atomes de carbone dans la chaîne grasseFà des teneurs deux ou trois fois moins élevées,en raison de leur nature structurale.4-To be able to lead to efficacy results, identical to lipoamino acids containing more than five carbon atoms in the fatty chain At levels two or three times lower, due to their structural nature.

Pour obtenir des dérivés batyryls d'acides aminés soufrés,on ut lisera préférentiellement l'anhydride butyrique plutot que le chic de butyryle;l'anhydride permettant d'obtenir une acylation totale, sans laisser d'acides aminés libres dans le milieu réactionnel. To obtain batyryl derivatives of sulfur amino acids, we will preferentially read butyric anhydride rather than chicory of butyryl, the anhydride making it possible to obtain total acylation, without leaving free amino acids in the reaction medium.

L'acylation des acides aminés soufrés conduit d'une part à la formation de dérivés acylés et, d'autre part å de l'acide butyriqt selon la réaction:

Figure img00010001

anhydride butyrique acide aminé butyrylaminoacide acide
R=ch ine soufrée butyris
Comme exemples de préparations,citons:: I-Butyrylméthionine
Dans un réacteur placé dans un bain marie,on introduit 45 grs de méthionine (3/IOe de mol) et 50 ml de solution de soude caust- ique à 30.0n coule,goutte à goutte 50 grs d'anhydride butyrique, sous forte agitation;on ajoute la quantité nécessaire de soude pour maintenir le pH entre IO et IO,5.Lorsque l'opération d'acylation est terminée,on porte la température du milieu réactionnel à 700 durant 30 minutes.Après refroidissement,on acidifie par 1' acide chlorhydrique de D=I,I9,jusqutz pH 2.The acylation of sulfur amino acids leads on the one hand to the formation of acylated derivatives and, on the other hand to butyriqt acid according to the reaction:
Figure img00010001

butyric anhydride amino acid butyrylamino acid acid
R = ch ine sulfur butyris
Examples of preparations include: I-Butyrylmethionine
45 gr of methionine (3/10 mol) and 50 ml of caustic soda solution at 30.0n are poured into a reactor placed in a water bath, drop by drop 50 gr of butyric anhydride, with vigorous stirring ; the necessary quantity of sodium hydroxide is added to maintain the pH between 10 and 10, when the acylation operation is complete, the temperature of the reaction medium is brought to 700 for 30 minutes. After cooling, the acidified with 1 ' hydrochloric acid from D = I, I9, up to pH 2.

On s'assure,par formoltitration que le milieu réactionnel ne comporte plus de méthionine libre.La couche surnageante est transferée dans un ballon muni de dispositif pour distillation sous vide,pour éliminer l'eau et l'acide chlorhydrique entrainé.  It is ensured, by formulation that the reaction medium no longer contains free methionine. The supernatant layer is transferred into a flask provided with a device for vacuum distillation, to remove the water and the hydrochloric acid entrained.

Le contenu du ballon est alors traité plusieurs fois par l'éther de pétrole qui entraine l'acide butyrique,par filtration de la masse cristalline qui sera ensuite sechée sous vide.The contents of the flask are then treated several times with petroleum ether which entrains butyric acid, by filtration of the crystalline mass which will then be dried under vacuum.

Poids obtenu 61 grs
Rendement par rapport à
la théorie 92
Analyse: P.X: 2I9-Azote théorique:6,4;Azote trouvé:6,2 -Soufre théorique:I4,6 ; Soufre trouvé: I4r3 - Indice d'acide théorique: 255;Indice d'acide trouve: 257. Weight obtained 61 grs
Performance versus
theory 92
Analysis: PX: 2I9-Theoretical nitrogen: 6.4; Nitrogen found: 6.2 -Theoretical sulfur: I4.6; Sulfur found: I4r3 - Theoretical acid number: 255; The acid number found: 257.

2-Butyrylcystine:
48 grs de cystine ( 4/IOe de mol) sont introduits dans le réacteur;on ajoute 60 ml de solution de soude,et on coule 64 grs d'anhydride butyrique*On procède ensuite comme pour l'exemple I.2-Butyrylcystine:
48 grs of cystine (4/10 mol) are introduced into the reactor; 60 ml of sodium hydroxide solution are added, and 64 grs of butyric anhydride are poured in * We then proceed as for Example I.

Comme solvant d'extraction de l'acide butyrique,on utilise l'éther isopropylique,
Poids obtenu 73 grs
Rendement par rapport à
la théorie 9I
Analyse: P.M :382-Azote théorique:7,3;azote trouvé:7,I - Soufre théorique: 16,8 ; Soufre trouvé: 16,5 - Indice d'acide théorique: 294 ; indice d'acide trouvé: 305 3-Butyrylcystéine:
On réalise la butyrylcystine selon l'exemple 2*Après décantation de la partie surnageante,celle ci est traitée par de l'acide chlorhydrique et de la poudre de zinc,sous agitation, afin d'obtenir une bonne réduction du pont cystinique en groupes sulfhydriles.On élimine ensuite l'acide chlorhydrique par distlllation sous vide.As butyric acid extraction solvent, isopropyl ether is used,
Weight obtained 73 grs
Performance versus
9I theory
Analysis: PM: 382-Theoretical nitrogen: 7.3; nitrogen found: 7, I - Theoretical sulfur: 16.8; Sulfur found: 16.5 - Theoretical acid number: 294; acid number found: 305 3-Butyrylcysteine:
Butyrylcystine is produced according to Example 2 * After decantation of the supernatant, it is treated with hydrochloric acid and zinc powder, with stirring, in order to obtain a good reduction of the cystinic bridge into sulfhydrile groups The hydrochloric acid is then removed by vacuum distillation.

La masse restante est reprise par du méthanol,cui rar filtration, permet de séparer le chlorure de zinc formé.0n élimine le méthanol et on traite la masse cristalline par l'éther isonropylioue,pour éliminer l'acide butyrique. The remaining mass is taken up in methanol, which is filtered, allows the zinc chloride formed to be separated. The methanol is removed and the crystalline mass is treated with isonropyl ether, to remove the butyric acid.

Poids obtenu (à partir de
11 exemple 2 71 grs
Rendement par rapport à
la théorie
Analyse: P.y.: I92 - Azote théorique: 7,3 ; Azote trouvé: 7,I
Soufre théorique: I6,7 ; Soufre trouvé: I6,5 - Indice d'acide théorique: 293 ; Indice d'acide trouvé: 307 -Fonction -SH théoriq
I7,I ; Fonction -SH trouvée par 12 O,I N : I6,8.Weight obtained (from
11 example 2 71 grs
Performance versus
the theory
Analysis: Py: I92 - Theoretical nitrogen: 7.3; Nitrogen found: 7, I
Theoretical sulfur: I6.7; Sulfur found: I6.5 - Theoretical acid number: 293; Acid index found: 307 -Function -SH theoriq
I7, I; -SH function found by 12 O, IN: I6.8.

A titre-de produits industriels nouveaux,l'invention s'étend à toutes compositions destinées à ètre utilisées chez l'homme,l'ani mal ou le végétal,caractérisées en ce qu'elles comportent essenti lement la chaine butyrique combinée à la fonction acylable ND2, d tous acides aminés soufrés protéiniques ou non protéiniques. As new industrial products, the invention extends to all compositions intended to be used in humans, animals or plants, characterized in that they essentially comprise the butyric chain combined with the function acylable ND2, d all sulfur amino acids protein or non-protein.

Comme exemples non limitatifs,citons,pour l'homme,l'intéret bic logique de ce type de structures de lipoaminoacides soufrés,pour l'activation du processus de kératogénèse,dans le traitement des ongles et des cheveux, ainsi que pour les soins de notre revbtemer cutané (kératine du stratum corneum),sous formes liquide ou pateu
Lotions pour les soins des ongles:
a) Butyrylcystine I
Eau 99
b) Butyrylméthionine I
Ethanol I5
Eau qs I00
Lotions pour les soins de la chevelure: :
a) Butyrylcystéine
Ethanol I5
Eau qs 100
b) Butyryméthonine I
Eau 99
Crème pour les soins épidermiques Buttrylcystine
Stéarine 5
Alcool cétylique polyoxy
éthyléné 5
Palmitate d'isopropyle IO
Glycérol IO
Conservateur qs
Eau qs I00
Chez l'animal,pour les soins du pelage:
Butyrylcystine 0,5
Butyrylméthionine 0,5
Propylèneglycol 5
Eau qs IOC
Pour les végétaux,comme activateurs de développement:
a) pour le traitement des racines
Butyryl methionine ou cystine: O,I à I
Bentonite ou kaolin qs I00
b) pour le traitement des feuilles
Butyryl méthionine ou cystine:C,5 à 5
Ean: I000 ml
L'invention s'étend également à toutes compositions destinées à l'usage humain ou destines à ètre appliquées sur l1animal ou le végétal;caractérisées en ce cue les carboxyles libres des structures liposmînoacides soufrées,citées comme exemples,ou toutes autres structures de ce type,peuvent être salifiées tar des bases minérales,organiques ou biologiques ou encore par des métaux considérés comme oligo-éléments.As nonlimiting examples, let us quote, for the man, the logical bic interest of this type of structures of sulfur lipoamino acids, for the activation of the process of keratogenesis, in the treatment of the nails and the hair, as well as for the care of our skin covering (keratin of the stratum corneum), in liquid or pateu forms
Nail care lotions:
a) Butyrylcystine I
Water 99
b) Butyrylmethionine I
Ethanol I5
Water qs I00
Hair care lotions::
a) Butyrylcysteine
Ethanol I5
Water qs 100
b) Butyrymethonin I
Water 99
Cream for epidermal care Buttrylcystine
Stearin 5
Polyoxy cetyl alcohol
ethylene 5
Isopropyl palmitate IO
Glycerol IO
Conservative qs
Water qs I00
In animals, for coat care:
Butyrylcystine 0.5
Butyrylmethionine 0.5
Propylene glycol 5
Water qs IOC
For plants, as development activators:
a) for root treatment
Butyryl methionine or cystine: O, I to I
Bentonite or kaolin qs I00
b) for processing leaves
Butyryl methionine or cystine: C, 5 to 5
Ean: I000 ml
The invention also extends to all compositions intended for human use or intended to be applied to animals or plants; characterized in this regard, the free carboxyls of the liposminoacid sulfur structures, cited as examples, or any other structures of this type. , can be salified by mineral, organic or biological bases or by metals considered as trace elements.

Ces sels pourront ètre facilement obtenus par:
a) neutralisation des carboxyles des butyrylaminoacides soufrés cités,à l'aide des bases minérales comme la soude, la potasse;de bases organiques comme la triéthanolamine,diéthylami- ne,morpholine ou encore par des bases biologiquestcomme les acides aminés basiques comme la lysine,l'arginine,l'ornithine ou des amines biologiques comme la choline,la guanidine etc...These salts can easily be obtained by:
a) neutralization of the carboxyls of the sulfur-containing butyrylamino acids mentioned, using mineral bases such as sodium hydroxide, potassium hydroxide; organic bases such as triethanolamine, diethylamine, morpholine or by biological bases such as basic amino acids such as lysine, arginine, ornithine or biological amines such as choline, guanidine etc ...

b) par traitement à chaud à l'aide d'hydrates ou de carbonates de magnésium,zinc,cuivre,cobalt etc... b) by hot treatment using hydrates or carbonates of magnesium, zinc, copper, cobalt, etc.

Les sels ainsi obtenus pourront ètre utilisés soit en association, soit à la place des butyrylaminoacîdes soufrés,indiqués dans les différentes compositions citées comme exemples.  The salts thus obtained can be used either in combination or in place of the sulfur-containing butyrylaminoacids indicated in the various compositions cited as examples.

Claims (5)

- REVEND I C AT ION S -  - RESELL I C AT ION S -
Figure img00050001
Figure img00050001
 I-Nouveaux dérivés d'acides aminés soufrés,caractérisés en ce qu'ils résultent de la combinaison d'une chaîne butyryle avec les fonctions acylables NH2 des dits acides aminés,conformément à la structure générale: I-New derivatives of sulfur-containing amino acids, characterized in that they result from the combination of a butyryl chain with the acylable NH 2 functions of said amino acids, in accordance with the general structure: Dans laquelle R représente un reste de la chaîne de la méthionine,de la cystine ou de la cystéine, ou encore de tous autres acides aminés protéiniques ou non protéiniquesble soufre pouvant être situé à n'importe quel emplacement de la partie R de la molécule. In which R represents a residue of the chain of methionine, of cystine or of cysteine, or of any other protein or non-protein amino acids sulfur which can be located at any location of the R part of the molecule. 2-Compositions kératogéniques destinées aux soins des ongles, des cheveux et de l'épiderme humain, caractérisées en ce qu'elles comportent des structures selon la revendication I. 2-Keratogenic compositions intended for the care of the nails, the hair and the human epidermis, characterized in that they comprise structures according to claim I. 3-Compositions kératogéniques destinées au traitement du pelage des animaux,caractérîsées en ce qu'elles comportent des structure selon la revendication I. 3-Keratogenic compositions intended for the treatment of the coat of animals, characterized in that they comprise structures according to claim I. 4-Compositions destinées à l'agriculture,comme agents de ferti lisation,caracEtérisées en ce qu'elles comportent des structures selon la revendication I.  4-Compositions intended for agriculture, as fertilizers, characEterized in that they comprise structures according to claim I. 5-Compositions destinées à l'usage humain, animal ou végétal, caractérisées en ce que les structures butyryl aminoacides décrit à la revendication I sont salifiées par des bases organiques,mind rales ou biologiques ou encore par des métaux classés comme oligc éléments,  5-Compositions intended for human, animal or vegetable use, characterized in that the butyryl amino acid structures described in claim I are salified with organic, mental or biological bases or even with metals classified as oligc elements,
FR8106592A 1981-04-02 1981-04-02 Compsns. contg. N-butyryl alpha-aminoacid(s) - for cosmetic, hygienic, therapeutic or agricultural use Granted FR2503151A1 (en)

Priority Applications (5)

Application Number Priority Date Filing Date Title
FR8106592A FR2503151A1 (en) 1981-04-02 1981-04-02 Compsns. contg. N-butyryl alpha-aminoacid(s) - for cosmetic, hygienic, therapeutic or agricultural use
GB8208378A GB2097256B (en) 1981-04-02 1982-03-23 Compositions containing n-butyryl alphaaminoacids
DE3212448A DE3212448C2 (en) 1981-04-02 1982-04-02 Agents containing N-acylates of α-amino acids
JP5399982A JPS57183703A (en) 1981-04-02 1982-04-02 Novel composition for cosmetics, sanitation, treatment or agricultural gardening
US07/940,184 US4859653A (en) 1981-04-02 1986-12-09 Use of compositions of matter containing N-acylates of alpha aminoacids for the treatment of skin

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FR8106592A FR2503151A1 (en) 1981-04-02 1981-04-02 Compsns. contg. N-butyryl alpha-aminoacid(s) - for cosmetic, hygienic, therapeutic or agricultural use

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FR2503151A1 true FR2503151A1 (en) 1982-10-08
FR2503151B1 FR2503151B1 (en) 1984-07-20

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EP0304778A1 (en) * 1987-08-21 1989-03-01 Degussa Aktiengesellschaft Process for the production of N-acylated mercapto-alpha-amino acids
WO1990013538A1 (en) * 1989-05-02 1990-11-15 Aktiebolaget Draco Organic salts of cysteine derivatives
EP0415598A1 (en) * 1989-08-16 1991-03-06 Unilever Plc Cosmetic composition
EP0422765A1 (en) * 1989-08-16 1991-04-17 Unilever Plc Cosmetic composition
EP0440298A1 (en) * 1990-01-30 1991-08-07 Brocades Pharma B.V. Topical preparations for treating human nails
WO1991018594A1 (en) * 1990-06-08 1991-12-12 Aktiebolaget Astra The pharmacological use of certain cystine derivatives
EP0463514A1 (en) * 1990-06-28 1992-01-02 Astra Aktiebolag 3.3'-Dithiobis (propionic acids) and esters thereof
WO1993004669A1 (en) * 1991-08-30 1993-03-18 The Procter & Gamble Company Use of n-acetyl-l-cysteine and derivatives for regulating skin wrinkles and/or skin atrophy
WO1993011104A1 (en) * 1991-11-29 1993-06-10 Ab Astra Organic salts of n, n'-diacetyl cystine
LT4006B (en) 1990-06-08 1996-07-25 Astra Ab The pharmacological use of certain cystine derivatives
FR2731220A1 (en) * 1995-03-03 1996-09-06 Bieurope New alkali metal salts of di:succinyl-L-cystine
US5883126A (en) * 1995-03-14 1999-03-16 Astra Aktiebolag Pharmacological use of certain cystine derivatives
US5889050A (en) * 1991-06-21 1999-03-30 Astra Aktiebolag 3,3'-dithiobis (propionic acids) and esters thereof
FR3050108A1 (en) * 2016-04-13 2017-10-20 Soc La Biochimie Appliquee COSMETIC AND / OR DERMATOLOGICAL COMPOSITION FOR THE COMPACTION OF STRATUM CORNEUM
CN108029863A (en) * 2018-01-19 2018-05-15 广州英赛特生物技术有限公司 The application of butyryl glycine and its derivative in animal feed additive is prepared

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FR2619711B1 (en) * 1987-09-02 1991-01-11 Givaudan La Virotte Cie Ets COSMETIC APPLICATION OF PROLINE DERIVATIVES, HYDROXYPROLINE AND / OR MIXTURE OF AMINO ACIDS RESULTING FROM COLLAGEN HYDROLYSIS
JP2002080321A (en) * 2000-06-20 2002-03-19 Kyowa Hakko Kogyo Co Ltd Cosmetic
JP4841075B2 (en) * 2000-09-22 2011-12-21 旭化成ケミカルズ株式会社 Whitening cosmetics
JP6162579B2 (en) * 2013-11-14 2017-07-12 雪印メグミルク株式会社 New bacteriostatic or antibacterial agent

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FR2158018A1 (en) * 1971-10-28 1973-06-08 Oreal
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Cited By (23)

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