JPS59112909A - Cosmetic containing fat soluble elastin peptide - Google Patents

Abstract

PURPOSE:A cosmetic containing fat-soluble elastin peptide, showing fully emollient effect or specific lubrication filling effect of moisture absorption, expected further to have beautifying effect on the skin. CONSTITUTION:A cosmetic containing fat soluble elastin peptide shown by the formula (R is fatty carboxylic acid residue; R' is alkyl). The compound shown by the formula has good solubility in fats and oils such as oil base useful as a cosmetic, and can be blended with an oily cosmetic. The compound shown by the formula, for example, is obtained by treating elastin peptide prepared by an acid or alkali treatment or enzymatic hydrolysis treatment of ligament or vascular wall with a fatty carboxylic acid ester, etc.

Description

DETAILED DESCRIPTION OF THE INVENTION This invention provides a decomposition product of naelastin protein, which is insoluble in fats and oils, obtained by acid or alkali or enzymatic decomposition treatment from protein fibers or blood vessel walls constituting mammalian skin tissue. n in the originally obtained general formula [1] is 2 to 30
The fat-soluble elastin peptide of the present invention has good solubility in fats such as oil haze used in cosmetics.

Numerous studies have been conducted to apply elastin fibers to cosmetics. Alternatively, it is known to use elastin peptides that are soluble in water by treatment with alkali and enzymatic decomposition such as proteinase.
,M., ,Davis H,F.

and Adair G, S, (Biochem.

J, -1 Yuyu 11-21) 1955, 1, (Kell
er S., and Mandl, J., (Eioche
m, Mediains -5,842~84'7)1
971), [Publication Patent Publication: 1972-72832),
(Public Patent Publication: 1984-105238).

One of the uses of water-soluble elastin peptides obtained from the Nishin ligament and blood vessel walls is in cosmetics. However, since all conventional elastin peptides are water-soluble when incorporated into cosmetics,
Oil-based cosmetic bases, such as olive oil, castor oil, coconut oil, various other vegetable oils, liquid paraffin, petrolatum, mineral oils such as ceresin, isopropyl myristate, isopropyl palmitate, octyldodecyl myristate, etc. Fatty acid esters have the disadvantage that they are rarely soluble. In other words, traditionally methyl,
It was only slightly soluble in lower alcohols such as ethyl or propyl alcohol. Therefore, since polyols such as polyethylene glycol, propylene glycol, and butylene glycol are soluble, it is necessary to use the above-mentioned polyols in advance when using them in oil-based cosmetics. , was restricted. In other words, when used in oil-based cosmetics,
Furthermore, using surfactants etc.

There were drawbacks such as a decrease in the emollient effect or unique moisturizing and slippery filling effect inherent to stinbebutide.

Therefore, the present inventors continued their research on elastin peptides that are soluble in oil bases, which are often used in cosmetics, and as a result, they succeeded in obtaining fat-soluble elastin peptides as described below. .

A method for producing fat-soluble elastin peptide (hereinafter abbreviated as OEP for convenience) according to the present invention is, for example, by decomposing the peptide from ligament or blood vessel walls using conventional methods, alkali, or enzymes. For the obtained elastin peptide, an aliphatic carboxylic acid ester or the like can be used, and the formula thereof is as follows.

In the formula, R is an aliphatic or aromatic carboxylic acid residue, and R'
represents an alkyl group, and X represents chlorine or bromine.

H2N ((! He ON +()nOHCOOH
+ ROOX + N ao HR' As mentioned above. The acylation method in the production of gp is as follows:
5chotten-E aum in other substances
It can be carried out according to the a m n reaction 〇 [Production method] Using the blood vessel wall or ligament, the elastin peptide contained in this tissue is treated with alkali and acid, and then boiled (heated) oxalic acid. A solution of elastin peptide extracted by a treatment method such as an alkaline ice-melting method containing alcohol or an elastase digestion method is prepared by adding a dilute alkaline solution to a solution of elastin peptide having a pH of 9.5 to 12.0. Then, about 60% of carboxylic acid halide is added dropwise at a temperature of 40 to 90°C with stirring over a period of about 30 minutes to 18 hours, and after the dropwise addition is completed, the mixture is further stirred at the same temperature for several hours. Next, the pH was adjusted to 4.0 or less with a dilute sulfuric acid solution, and the crude product after filtering to remove unreacted elastin peptide and solvent was dispersed in water, stirred warmly, and added for extraction. After this, purified OKP is obtained by recrystallization.

The novel acylated elastin peptide compound thus obtained is a pale yellow to pale yellowish brown crystalline substance that is sparingly soluble or insoluble in water, but is insoluble in various organic solvents and conventional elastin peptides. It is highly soluble in various vegetable oils, mineral oils, and various fatty acid esters, and can also be dissolved in higher fatty acid esters such as stearic acid and valmitic acid.

[Confirmation of physical properties]

Comparing the ogp obtained according to the above-mentioned production method, for example, an elastin peptide-acyl stearate compound and a known elastin peptide, it was found that in the Biillet reaction, both of them produced a reddish-purple color. ~Exhibits a bluish-purple color. Looking at the ultraviolet absorption spectrum (alcohol solution), it is as shown in Figure 1,
Although no particularly significant ultraviolet absorption is observed between the two, they differ from conventional elastin peptides in that they exhibit a broad shoulder over a wide range of 250 to 280 nm.

On the other hand, regarding stability, the browning phenomenon is suppressed in all acyl compounds under sunlight irradiation and heating conditions, compared to elastin peptides made into low-molecular-weight molecules. In other words, with conventional low-molecular elastin peptides,
If exposed to sunlight or heat for a long time, browning will progress, so the stability of products after they are incorporated into cosmetics, etc.
Although sufficient consideration was required, this is because glycine and alanine, the main constituent amino acids of elastin peptide, become nitrogen glycosides under the influence of sugars, ultraviolet rays, and heat, and then undergo Amatoli rearrangement. Wake up, Ami7
- It is believed that browning progresses when the carbonyl reaction is completed.

It has been found that in the OEP according to the present invention, such coloring tendency is significantly improved. Moreover, as can be understood from its chemical structure, the advantage of OEF is that it has excellent emulsifying and dispersing properties because it has the requirements as a surfactant. Therefore, it has become easy to use in creams, emulsions, etc. The solubility of OEF according to the present invention is as shown in Table 1. In Table 1, OEF is a compound obtained using stearic acid and lauric acid according to the above-mentioned production method. However, in production, if any other aliphatic carboxylic acid ester or aromatic carboxylic acid ester is selected and produced, any of them can be converted into OEF. All of these can be done by using the conventionally known 5chotten, -Baumamn reaction, and there is no need to limit the conditions.
It is not necessary to use particularly purified OKP, but when the molecular weight is large, the fatty acid will bind only to the N-terminus of the polypeptide, and for this reason, the produced OKP
Since it is also insoluble in organic solvents and water, it is better to set the upper limit of the molecular weight of the elastin peptide to a polypeptide of about 30,000 to a dipeptide of about 200 as the lower limit.

On the other hand, for hair applications such as hair coloring, if the purpose is to absorb it into the hair itself, it is optimal if the obtained OEP has a molecular weight of about 400 to 600. Therefore, for use in cosmetic formulations, tripeptides or tetrapeptides are advantageously used as the elastin peptides used in the production of OEP. Furthermore, when applying cosmetics to the skin to exhibit film properties on the epidermis, the optimal molecular weight of OEP is 10,000 to 30,000.

[Table 1] (Solubility) Furthermore, in the above-mentioned OEP manufacturing method, stearic acid and lauric acid were used as aliphatic carboxylic acid esters, but this was carried out using lower fatty acids and aromatic carboxylic acid esters. Although the solubility in oils and fats decreases when
Because it is highly soluble in ethanol, it is advantageous in formulations such as lotions and hair tonics that contain high amounts of ethanol.

〔safety〕

Regarding OKP according to the present invention, the safety of the compound obtained using stearic acid and lauric acid shown in the manufacturing method was determined in accordance with the FDA (Federal Food, Drug, and Cosmetic Act). , skin-secondary irritation,
Tests were conducted on ocular mucosal irritation, phototoxicity, contact allergies, etc., and no toxic effects were observed in any of the tests, confirming that the product is highly safe.
There is no concern about safety when applied externally to the skin. The LD50 value obtained by oral administration to mice (male) was 5ooO■/kq or more.

Next, two to three formulation examples will be shown regarding the addition of OEP according to the present invention to cosmetics.

[Prescription example]

(1) OK F-containing emulsion elastin peptide - stearic acid compound (OEP) -
＠・・・・−・・・・・・・・・・・l O, 0% carboxy polymer・・・・・・・・・ 0.2g
Ri Serin...Fist...Fighting e-book...2 1.0 Ethanol・ll11@Φ...
...1・----7,0 Setanol Fist...S...
・・Φ・・・・・・ 0021.3-Butylene glycol... 260 isopropyl myristic acid e@・
・・・ 0.5 Fragrance and preservatives・・・・・・・・・・・・
... Add an appropriate amount of purified water, total amount...100
%.

(OE P) ・・１・φ・・■−・・・・−−−−
7.0% octyldodecyl monooleate, 8.0 glycerin monooleate, 9.0 lanolin,
・・Koma・・11 tube・・・・・・・・・・113.0
Setanol @ @ Ba Mo @ Il ◆ II building ll5s ◆ Volume S $
Book 12.0 Stearic acid...Reference...Cloudy...
... 1.5 Liquid paraffin...Φ・-・・Φ
... 8.0 Ceresin...--e・l・
1...2.0 Fragrances and preservatives...
...... Total amount with appropriate amount of purified water...10
Set to 0%.

(a) OE P-containing hair rinse elastin peptide-propionic acid compound (OE P)
......1■...e...12. Q%
Polyvinyl pyrrolidone・・・・・・ 1.8 Water-soluble lanolin・・・・・・・・・・・・ 1.5
Detox acid 2 boot lium ・In the middle of the fist...
・・−0,25 ethanol・・−0・・III・・
@bone-・0・e・5.0 Fragrance and preservative...
・・・・・・・・・・The whole amount with appropriate purified ice...
...Set as 100%.

On the other hand, when looking at the tyrosinase activity suppressing effect of OEP according to the present invention, it was found that it suppresses tyrosinase activity and has the ability to suppress melanin production, similar to conventional water-soluble elastin peptides. This is advantageous for cosmetics since it is expected to have a skin whitening effect. Table 2 shows that a test solution (liquid A) was prepared using each sample, 2Qi was poured into a petri dish, cooled and solidified, and a 0.5% tyrosinase solution was poured over it. ℃
The agar was left in a constant temperature bath for a predetermined period of time, and the degree of blackening of the agar surface was observed, and the presence or absence of the inhibitory effect on chinase activity and the production of melanin pigment (blackening) was examined. Table] (Tyrosinase activity inhibition effect)

[Brief explanation of the drawing]

Figure 1 shows the elastin peptide-stearic acid compound (
This figure shows the ultraviolet absorption spectra of OE P), elastin peptide, and stearic acid. A is elastin peptide (average molecular weight 1500) - acyl stearate compound B is elastin peptide (average molecular weight 1500) C is stearic acid Patent Applicant Figure 1

Claims (1)

[Scope of Claims] A cosmetic composition containing a fat-soluble elastin peptide represented by the general formula (1) of elastin peptide (wherein R represents an aliphatic carboxylic acid residue and R' represents an alkyl group).