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KR-102961382-B1 - Ascorbic acid derivatives or their salts and their cosmetics

KR102961382B1KR 102961382 B1KR102961382 B1KR 102961382B1KR-102961382-B1

Abstract

The present invention provides a novel ascorbic acid derivative or salt thereof that possesses excellent original functions of ascorbic acid, such as whitening, collagen production promotion, and moisturizing effects, while remaining stable even during long-term storage and having minimal discoloration, change in odor, or decrease in activity, wherein one of the hydrogens in the hydroxyl groups at the 2nd or 3rd positions of ascorbic acid is substituted with RO- CH2 - CH( OH ) -CH2- , RO-CH2-CH( CH2OH )-, R-CH(CH2OH)-, R-CH(OH) -CH2- (R is H, an alkyl group, an alkenyl group, or a phenyl group), HO-C( CH3 ) 2 - CH2- , or HO- CH2 -C( CH3 ) 2- , and provides a cosmetic composition containing the same.

Inventors

  • 요시오카 마사토
  • 혼다 타스쿠
  • 이토 마사히로
  • 이와키 노부야스
  • 토미야마 아이
  • 스즈키 사키

Assignees

  • 세이와 카세이 콤파니 리미티드

Dates

Publication Date
20260508
Application Date
20230616
Priority Date
20221125

Claims (8)

  1. Ascorbic acid derivative or salt thereof characterized by being represented by the following general formula (I). [During the meal, R1 and R2 are H, an alkyl group having 1 to 22 carbon atoms, an alkenyl group having 2 to 22 carbon atoms, a benzyl group, R3 -O- CH2 -CH(OH) -CH2- , R3 -O- CH2 -CH( CH2OH )-, R3 -CH( CH2OH )-, R3 -CH(OH) -CH2- , HO-C( CH3 ) 2 - CH2- or HO- CH2 -C( CH3 ) 2- , and R3 is H, an alkyl group having 1 to 22 carbon atoms, an alkenyl group having 2 to 22 carbon atoms, or a phenyl group. However, at least one of R1 and R2 is HO-C( CH3 ) 2 - CH2- or HO- CH2 -C( CH3 ) 2- .
  2. In claim 1, An ascorbic acid derivative or salt thereof, characterized in that, in the above general formula (I), one of R1 or R2 is HO-C( CH3 ) 2 - CH2- or HO- CH2 -C( CH3 ) 2- , and the other of R1 or R2 is an alkyl group having 2 to 20 carbon atoms or a branched alkylglyceryl group having 6 to 20 carbon atoms.
  3. In claim 1, An ascorbic acid derivative or salt thereof, characterized in that, in the above general formula (I), one of R1 or R2 is HO-C( CH3 ) 2 - CH2- or HO- CH2 -C( CH3 ) 2- and the other of R1 or R2 is a benzyl group.
  4. In claim 1, An ascorbic acid derivative or salt thereof, characterized in that, in the above general formula (I), one of R1 or R2 is HO-C( CH3 ) 2 - CH2- or HO - CH2 -C( CH3 ) 2- , and the other of R1 or R2 is R3 -O- CH2 -CH(OH) -CH2- or R3 -O- CH2 -CH( CH2OH )-.
  5. In claim 1, An ascorbic acid derivative or salt thereof, characterized in that, in the above general formula (I), one of R1 or R2 is HO-C( CH3 ) 2 - CH2- or HO- CH2 -C( CH3 ) 2- and the other of R1 or R2 is H, alkyl or alkenyl, and the sum of the carbon numbers of R1 and R2 is 8 or less, or the other of R1 or R2 is R3 -O- CH2 -CH(OH) -CH2- , R3 -O- CH2 -CH( CH2OH )-, HO-C( CH3 ) 2 - CH2- or HO- CH2 -C( CH3 ) 2- and the number of carbon numbers of R3 is 4 or less.
  6. In claim 1, An ascorbic acid derivative or salt thereof, characterized in that, in the above general formula (I), one of R1 or R2 is HO-C( CH3 ) 2 - CH2- or HO- CH2 -C( CH3 ) 2- , and the other of R1 or R2 is R3 -CH( CH2OH )- or R3 -CH(OH) -CH2- .
  7. A cosmetic composition characterized by incorporating an ascorbic acid derivative or a salt thereof as described in any one of claims 1 to 6.
  8. A cosmetic composition characterized by incorporating 1 to 20 weight% of an ascorbic acid derivative or salt thereof described in any one of claims 1 to 6.

Description

Ascorbic acid derivatives or their salts and their cosmetics The present invention relates to an ascorbic acid derivative or a salt thereof that is suitably used as a raw material for cosmetics, and also relates to a cosmetic formulation incorporating said ascorbic acid derivative or a salt thereof. Ascorbic acid is known as a safe and useful antioxidant and a compound with excellent whitening properties, but on the other hand, it is unstable against light, heat, and oxidation, which has hindered its use in the cosmetics field. Therefore, various ascorbic acid derivatives or salts thereof have been proposed as having improved stability over time compared to ascorbic acid, and formulations for external skin preparations for whitening (Patent Document 1, Patent Document 2) or formulations for cosmetics (Patent Document 3) have been proposed. However, most of the aforementioned ascorbic acid derivatives and their salts have problems such as discoloration or odor generation over time, so their stability over time is still insufficient, and furthermore, the duration of activity in vivo is short-term, so improvement is desired. The inventors have proposed an ascorbic acid derivative that solves these problems (Patent Document 4), but further improvement is desired. Hereinafter, HO-C( CH3 ) 2 - CH2- or HO-CH2 - C( CH3 ) 2- is represented as a "hydroxyisobutyl group". Furthermore, hydroxyisobutylascorbic acid refers to ascorbic acid in which a hydroxyisobutyl group is bonded to one or more of the oxygen atoms of each hydroxyl group. The ascorbic acid derivative of the present invention is hydroxyisobutylascorbic acid, wherein a hydroxyisobutyl group is bonded to the 2nd and/or 3rd positions. Specific examples of ascorbic acid derivatives represented by general formula (I) include compounds shown below, but the scope of the present invention is not limited to those shown below. In addition, in the following examples, Glyceryl represents HOCH 2 -CH(OH)-CH 2 - or HOCH 2 -CH(CH 2 OH) -, An alkylglyceryl group represents RO- CH2 -CH(OH) CH2- or RO- CH2 -CH( CH2OH )- (R indicates an alkyl group), and A hydroxyalkyl group refers to a 1-alkyl-2-hydroxyethyl group represented as R-CH(OH) -CH2- (R indicates an alkyl group), and A hydroxyalkenyl group refers to a 1-alkenyl- 2 -hydroxyethyl group represented as R-CH(OH)-CH2- (R indicates an alkenyl group), and The term "alkyl group" refers to methyl, ethyl, propyl, isopropyl, butyl, isobutyl, pentyl, hexyl, ethylhexyl, heptyl, octyl, nonyl, decyl, undecyl, dodecyl, tridecyl, tetradecyl, pentadecyl, hexadecyl, heptadecyl, octadecyl, nonadecyl, eicosyl, behenyl, etc. The alkenyl group refers to the vinyl group, allyl group, butenyl group, isobutenyl group, crottyl group, octenyl group, decenyl group, dodecenyl group, etc. (1) 3-O-hydroxyisobutylascorbic acid, 3-O-hydroxyisobutyl-2-O-alkylascorbic acid, e.g., 3-O-hydroxyisobutyl-2-O-ethylascorbic acid, 3-O-hydroxyisobutyl-2-O-butylascorbic acid, 3-O-hydroxyisobutyl-2-O-hexylascorbic acid, 3-O-hydroxyisobutyl-2-O-octylascorbic acid, 3-O-hydroxyisobutyl-2-O-decylascorbic acid, 3-O-hydroxyisobutyl-2-O-ethylhexylascorbic acid, 3-O-hydroxyisobutyl-2-O-dodecylascorbic acid, 3-O-hydroxyisobutyl-2-O-tetradecylascorbic acid, 3-O-hydroxyisobutyl-2-O-hexadecylascorbic acid; 3-O-hydroxyisobutyl-2-O-alkenylascorbic acid, e.g., 3-O-hydroxyisobutyl-2-O-allylascorbic acid, 3-O-hydroxyisobutyl-2-O-octenylascorbic acid, 3-O-hydroxyisobutyl-2-O-dodecenylascorbic acid; 3-O-hydroxyisobutyl-2-O-glyceryl ascorbic acid; 3-O-hydroxyisobutyl-2-O-alkylglyceryl ascorbic acid, e.g., 3-O-hydroxyisobutyl-2-O-butylglyceryl ascorbic acid, 3-O-hydroxyisobutyl-2-O-ethylhexylglyceryl ascorbic acid, 3-O-hydroxyisobutyl-2-O-dodecylglyceryl ascorbic acid; 3-O-hydroxyisobutyl-2-O-alkenylglyceryl ascorbic acid, e.g., 3-O-hydroxyisobutyl-2-O-dodecenylglyceryl ascorbic acid; 3-O-hydroxyisobutyl-2-O-phenylglyceryl ascorbic acid; 3-O-hydroxyisobutyl-2-O-benzylascorbic acid; 3-O-hydroxyisobutyl-2-O-(2-hydroxyalkyl)ascorbic acid, e.g., 3-O-hydroxyisobutyl-2-O-(2-hydroxypropyl)ascorbic acid, 3-O-hydroxyisobutyl-2-O-(2-hydroxydecyl)ascorbic acid, 3-O-hydroxyisobutyl-2-O-(2-hydroxyhexadecyl)ascorbic acid, 3-O-hydroxyisobutyl-2-O-(2-hydroxyethylbenzene)ascorbic acid; 3-O-hydroxyisobutyl-2-O-(1-alkyl-2-hydroxyethyl)ascorbic acid, e.g., 3-O-hydroxyisobutyl-2-O-(1-methyl-2-hydroxyethyl)ascorbic acid, 3-O-hydroxyisobutyl-2-O-(1-ethyl-2-hydroxyethyl)ascorbic acid, 3-O-hydroxyisobutyl-2-O-(1-octyl-2-hydroxyethyl)ascorbic acid, 3-O-hydroxyisobutyl-2-O-(1-tetradecyl-2-hydroxyethyl)ascorbic acid, 3-O-hydroxyisobutyl-2-O-(1-phenyl-2-hydroxyethyl)ascorbic acid. (2) 2-O-hydroxyisobutylascorbic acid, 2-O-hydroxyisobutyl-3-O-alkylascorbic acid, e.g., 2-O-hydroxyisobutyl-3-O-ethylascorbic acid, 2-O-hydroxyisobutyl-3-O-butylascorbic acid, 2-O-hydroxyisobutyl-3-O-hexylascorbic acid, 2-O-hydroxyisobutyl-3-O-octylascorbic acid, 2-O-hydroxyisobutyl-3-O-decylascorbic acid, 2-O-hydroxyisobutyl-3-O-eth