CN1531416A - Cosmetic for skin whitening containing acyl substituted derivatives of glucose or sucrose - Google Patents

Cosmetic for skin whitening containing acyl substituted derivatives of glucose or sucrose Download PDF

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CN1531416A
CN1531416A CNA018215157A CN01821515A CN1531416A CN 1531416 A CN1531416 A CN 1531416A CN A018215157 A CNA018215157 A CN A018215157A CN 01821515 A CN01821515 A CN 01821515A CN 1531416 A CN1531416 A CN 1531416A
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glucose
sucrose
isovalerate
isobutyrate
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CN1229107C (en
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金原灿
金镐正
金清泽
陈戊铉
姜常真
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LG H&H Co Ltd
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LG Household and Health Care Ltd
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    • 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
    • A61Q19/02—Preparations for care of the skin for chemically bleaching or whitening 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
    • A61K8/02—Cosmetics or similar toiletry preparations characterised by special physical form
    • A61K8/0212—Face masks
    • 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
    • A61K8/60—Sugars; Derivatives thereof
    • 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
    • A61Q19/08—Anti-ageing preparations

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Abstract

The present invention relates to cosmetic for skin whitening containing glucose derivatives having 3- 5 of acyl groups and/or sucrose derivatives having 6 -8 of acyl groups as an effective component. Glucose acyl substituted derivatives and sucrose acyl substituted derivatives are easy to synthesize, have no side effects on skin, and have a superior effect to inhibit pigmentation on skin by restraining melanin from being generated. Accordingly, the cosmetic containing the same material is usefully used for skin whitening.

Description

Contain the glucose of acyl substituted or the cosmetic for skin whitening of sucrose derivative
Technical field
The present invention relates to cosmetic for skin whitening; particularly a kind of cosmetic for skin whitening that contains glucose or sucrose acyl derivative; cosmetics provided by the present invention are easy to synthesize, skin are free from side effects, thereby by limiting the pigmentation that melanic generation efficiently suppresses skin.
Background technology
A lot of people want to have the skin of pure white exquisiteness.People's the colour of skin is to be decided by melanic density in the skin and distribution, is subjected to the influence of environment or physiologic factor simultaneously again, such as the ultraviolet in the sunlight, and fatigue, pressure and inherited genetic factors.Melanin is synthetic by following step: at first, tryrosinase acts on a seed amino acid, and tyrosine makes it change into DOPA (DOPA) or DOPA quinone (dopaquinone), and it reacts through non-enzymatic oxidation then.Yet although the melanin synthetic method is open, the details of step, the melanic synthesis mechanism of initiation is also not clear and definite before the tryrosinase effect.
Excessively synthetic in skin when melanin, the colour of skin is with blackening, and chloasma and freckle also will occur.Therefore, melanic synthetic being suppressed in skin, whiteness of skin is possible, in addition, because the too high disease of melanin that ultraviolet or factors such as hormone and heredity cause also can be enhanced such as symptoms such as freckle, chloasma.
Usually, skin-whitening is material for example hydroquinone, ascorbic acid, kojic acid (kojic acid) or the glutathion and cosmetics mixing externals such as essence, ointment by will containing restraint of tyrosinase.But although the whitening effect of hydroquinone is fine, because it is bigger to the zest of skin, its consumption is limited in minimum.And ascorbic acid is oxidized easily, and the cosmetics variable color that causes being mixed with ascorbic acid is spoiled, and kojic acid is same because unstable and be limited consumption.In addition, mercaptan compound for example glutathion or cysteine has a kind of special strange taste, and the absorbability of skin is low.
On the other hand, there is report to show plant extract, good skin whitening function (Fragrance.J., 6,59 (1990)) arranged such as licorice (licorice) extract or Morus alba tree (white mulberry) extract.But because the difference of plant growing region, the diversity of product effect is bigger, thereby is difficult to keep the homogeneity of product.In addition, also insufficient for the check of skin irritation and stability.The kazinol F (Chem.Phar.Bull., 34 (5) 1968 (1986), the Cosmetics ﹠amp that extract in the root of Broussonetiapapyrifera(I)vent (paper mulberry); Toiletries, 101,51 (1995)), the sucrose-4 that extracts in the Euphorbia lathyris (Euphorbia lathyris), 7,8,11,12-five-isovalerate, (Kor.J.Pharmacogn.21 (2): 168-173 (2000)) etc. is also because it is difficult to synthetic and low synthetic ratio and can't commercialization.
Summary of the invention
The objective of the invention is to overcome above-mentioned technological deficiency, provide a kind of easily synthetic, skin is free from side effects, efficiently suppress the cosmetic for skin whitening of the pigmentation of skin by the generation of restriction melanin.
To describe cosmetics provided by the present invention in detail below.
Cosmetic for skin whitening provided by the invention contains a kind of glucose acyl substituted derivant that Chemical formula 1 is represented, sucrose acyl substituted derivant that Chemical formula 2 is represented, and the material of their mixture of being selected from of effective dose.
Chemical formula 1 is:
Figure A0182151500051
In Chemical formula 1, R represents hydrogen atom or has the acyl group of 3-6 carbon.Acyl group is straight chain or side chain, and the acyl group number of replacement is 3-5.
Chemical formula 2 is:
In Chemical formula 2, radicals R is represented hydrogen atom or is had the acyl group of 3-6 carbon.Acyl group is straight chain or side chain, and the number of substituted acyl is 6-8.
The derivant of the derivant of glucose acyl substituted provided by the present invention or sucrose acyl substituted is easy to synthetic and can efficiently suppresses melanic generation, and the ground skin whitening can have no side effect.Therefore, if these materials are joined in cosmetics such as essence, external cream, the facial cream, do not have the highly effective skin of any special side effect and whiten and to realize.
The derivant of the derivant of glucose acyl substituted provided by the invention or sucrose acyl substituted can be according to following reaction equation by conventional known synthetic method preparation (seeing Synthesis, 453 (1986)).
Reaction equation 1:
Figure A0182151500061
In the superincumbent reaction equation 1, radicals R is represented hydrogen atom or is had the acyl group of 3-6 carbon.Acyl group is straight chain or side chain, and the acyl group number of replacement is 3-5.
Reaction equation 2:
In reaction equation 2, radicals R is represented hydrogen atom or is had the acyl group of 3-6 carbon.Acyl group is straight chain or side chain, and the acyl group number of replacement is 6-8.
Understand because of reaction temperature, response time, whether use catalyst that the acyl substituent of different numbers is arranged according to the derivant of the synthetic dextrose plus saccharose acyl substituted of above-mentioned reaction equation.The glucose acyl substituted derivant that contains 3-5 acyl group has efficiently suppressing melanic generation with the sucrose acyl substituted derivant that contains 6-8 acyl group.
When the acylation reaction that generates dextrose plus saccharose acyl substituted derivant carried out, dimethyl formamide, dimethyl sulfoxine or pyrimidine can be used as solvent and use, and wherein pyrimidine is preferred.In addition, anhydrous propanoic acid, anhydrous butanoic acid, anhydrous isopropylformic acid., anhydrous valeric acid, anhydrous isovaleric acid, anhydrous 2 Ethylbutanoic acid, anhydrous caproic acid, perhaps anhydrous 2 methyl valeric acid can be used as the anhydrous carboxylic acid who is used for acylation reaction.
The derivant of the glucose acyl substituted that is made by above-mentioned reaction equation 1 can separated purification be a glucose-1,2,3,4; 6-five-O-isovalerate, glucose-1,2,3; 4-four-O-isovalerate, glucose-1,2,4; 6-four-O-isovalerate, glucose-1,2,3; 6-four-O-isovalerate, glucose-1,3,6-three-O-isovalerate; glucose-1,2,3,4; 6-five-O-isobutyrate, glucose-1,2,3; 4-four-O-isobutyrate, glucose-1,2,4; 6-four-O-isobutyrate, glucose-1,2,3; 6-four-O-isobutyrate, glucose-1,2,3-three-O-isobutyrate etc.This wherein, a kind of α and β type chemical compound, with the glucose-1,2,3,4 that following chemical formula 3 is represented, 6-five-O-isovalerate has efficiently skin-whitening.
Chemical formula 3 is:
In above-mentioned chemical formula 3, radicals R is meant:
Figure A0182151500072
In addition, the derivant by above-mentioned reaction equation 2 synthetic sucrose acyl substituted can separated purification be sucrose-2,3,4,7,8,10; 11,12-eight-O-isovalerate, sucrose-2,4,7,8,10,11; 12-seven-O-isovalerate, sucrose-3,7,8,10,11,12-six-O-isovalerate; sucrose-2,3,4,7,8,10,11; 12-eight-O-isobutyrate, sucrose-2,4,7,8,10,11; 12-seven-O-isobutyrate, sucrose-3,7,8,10,11,12-six-O-isobutyrate etc.
The derivant of such glucose or sucrose acyl substituted can with various cosmetics such as externally-applied ointment, facial cream, gentle skin emulsion (softening lotion), essence, makeup cream (pack), nutritional emulsions mixing such as (nutritiouslotion).The gross weight that the weight of the derivant of glucose provided by the invention and/or sucrose acyl substituted accounts for cosmetics is preferably 0.0001-15%, more preferably is the 0.001-10% that accounts for gross weight.
The description of preferred embodiment
To describe in further detail the present invention with specific embodiments below.Can be with multiple mode changes in modification according to embodiment of the present invention, the present invention is not subjected to the restriction of following specific embodiments.Following specific embodiments only provides for those of ordinary skills understand the present invention better.
Synthetic embodiment 1 (glucose isovalerate derivant synthesis example)
5g (27.8mmol) glucose is placed a pair of neck round-bottomed flask, add the dissolving fully in water-bath of 50ml pyrimidine.Solution maintains 0 ℃, and slowly the normal anhydrous isovaleric acid of Dropwise 5 .5 stirs after 3 hours, and then adds 5.5 normal anhydrous isovaleric acid.Temperature is raised to 25 ℃ of reactions 30 hours.Add 150ml methanol stopped reaction, under reduced pressure solvent is removed fully, add the 300ml chloroform.The product of gained is used hydrochloric acid and the 250ml saturated sodium bicarbonate aqueous solution washed twice of 250ml 1N respectively.Chloroform layer is under reduced pressure drained, and obtains 13.5g grease.Gained grease separates with silica gel column chromatography and purifies (ethyl acetate/hexane 1: 5), obtains 4.5g glucose 1,2 respectively, 3,4,6-five-O-isovalerate (Rf=0.72, productive rate: 27.0%), 0.5g glucose-1,2,3,4-four-O-isovalerate (Rf=0.60, productive rate: 3.5%), 2.3g glucose-1,2,4,6-four-O-isovalerate (Rf=0.65, productive rate: 16.0%), 0.6g glucose-1,2,3,6-four-O-isovalerate (Rf=0.55, productive rate: 4.2%), 1.2g glucose-1,3,6-three-O-isovalerate (Rf=0.43, productive rate: 10.0%).
The glucose isovalerate derivant that obtains is by fast atom bombardment MALDI-MS (Fast AtomBombardment Mass Spectrometry is to call FAB-MS in the following text)) and the 300MHz nuclear magnetic resonance, NMR ( 1H, 13C) (NMR) identify,
Glucose-1,2,3,4,6-five-O-isovalerate
FAB?mass：623.4[M+Na] +
H-NMR(δ，CDCl 3)：6.36(1H，d，J3.71-α-H)，5.72(1H，d，J8.31-β-H)，5.50(1H，t，J10.13-α-H)，5.28(1H，t，J9.53-β-H)，5.06-5.19(4H，m，2，4-α，β-H)，5.06(2H，m，2-α，β-H)4.13-4.17(4H，m，6-α，β-H)，4.10(1H，m，5-α-H)，3.82(1H，m，5-β-H)，2.31-2.13(20H，m，5×CH 2CH(CH 3) 2)，2.13-2.03(5H，m，5×CH 2CH(CH 3) 2)，1.01-O.9(60H，m，4×CH 2CH(CH 3) 2)。
Glucose-1,2,3,4-four-O-isovalerate
FAB?mass：539[M+Na] +
H-NMR(δ，CDCl 3)：6.35(1H，d，J3.61-H)，5.61(1H，d，J9.53-H)，5.20-5.06(2H，m，2，4-H)，3.91(1H，ddd，J10，4.5，2，5-H)，3.79-3.63(2H，m，6-H)，2.30-2.13(8H，m，4×CH 2CH(CH 3) 2)，2.12-2.04(4H，m，4×CH 2CH(CH 3) 2)，1.01-0.9(24H，m，4×CH 2CH(CH 3) 2)
Glucose-1,2,3,6-four-O-isovalerate
FAB?mass：539[M+Na] +
H-NMR (δ, CDCl 3): 6.35 (1H, d, J3.61-H), 5.39 (1H, t, J10,3-H), 5.12 (1H, dd, J10 and 3.5,2-H), 4.61-4.52 (2H, m, 6-H), 3.99 (1H, ddd, J10,4 and 2.5,5-H), 3.60 (1H, t, J10,4-H), 2.32-2.14 (8H, m, 4 * CH 2CH (CH 3) 2), 2.12-2.02 (4H, m, 4 * CH 2CH (CH 3) 2), 1.01-0.9 (24H m, 4 * CH 2CH (CH 3) 2).
Glucose-1,2,4,6-four-O-isovalerate
FAB?mass：539[M+Na] +
H-NMR(δ，CDC l3)：6.33(1H，d，J3.61-H)，5.05-4.99(2H，m，2，4-H)，4.18(1H，dd，J10and3.5，2-H)4.61-4.52(2H，m，6-H)3.99(1H，ddd，J10，4and2.5，5-H)，3.60(1H，t，J10，4-H)2.32-2.14(8H，m，4×CH 2CH(CH 3) 2)2.12-2.02(4H，m，4×CH 2CH(CH 3) 2)1.01-0.9(24H，m，4×CH 2CH(CH 3) 2)
Glucose-1,3,6-three-O-isovalerate
FAB?mass：456[M+Na] +
H-NMR (δ, CDCl 3): 6.35 (1H, d, J3.6,1-H), 5.01 (1H, t, J9.8,3-H), 4.53 (2H, m, 6-H), 3.98 (2H, ddd, J9.8,4 and 2.5,5-H), 3.58 (1H, m, 4-H), 3.60 (1H, t, J9.8,2-H), 2.30-2.13 (8H, m, 4 * CH 2CH (CH 3) 2), 2.12-2.03 (3H, m, 3 * CH 2CH (CH 3) 2), 1.00-0.89 (18H, m, 3 * CH 2CH (CH 3) 2).
Synthetic embodiment 2 (glucose isobutyrate derivant synthesis example)
Except substituting the anhydrous isovaleric acid, synthesize the separation and the 3.5g glucose-1,2 of having purified with synthetic embodiment 1 identical method with anhydrous isopropylformic acid., 3,4,6-five-O-isobutyrate (Rd=0.80, productive rate: 27.5%), 0.4g glucose-1,2,3,4-four-O-isobutyrate (Rf=0.70, productive rate: 27.0%), 2.7g glucose-1,2,4,6-four-O-isobutyrate (Rf=0.68, productive rate: 23.0%), 0.61g glucose 1,2,3,6-four-O-isobutyrate (Rf=0.73, productive rate: 27.0%), 0.59g glucose-1,3,6-three-O-isobutyrate (Rf=0.65, productive rate: 5.0%).
The above-mentioned glucose isobutyrate derivant that obtains uses the method identical with synthesizing embodiment 1 to identify.
Glucose-1,2,3,4,6-five-O-isobutyrate
FAB?mass：558[M+Na] +
H-NMR (δ, CDCl 3): 6.33 (1H, d, J3.71-H), 5.49 (1Ht, J9.5,3-H), 5.13 (1H, t, J9.9,4-H), 5.06 (1H, dd, J9.9 and 3.7,2-H), 4.12 (2H, m, 6-H), 4.06 (1H, m, 5-H), 2.75-2.42 (5H, m, 5 * CH 2(CH 3) 2), 1.29-1.10 (30H, m, 5 * CH (CH 3) 2).
Glucose-1,2,3,4-four-O-isobutyrate
FAB?mass：488[M+Na] +
H-NMR(δ，CDCl 3)：6.35(1H，d，J3.6，1-H)，5.61(1H，t，J9.5，3-H)，5.20-5.06(2H，m，2，4-H)，3.91(1H，ddd，J10，4.5，2，5-H)，3.79-3.63(2H，m，6-H)，2.73-2.40(4H，m，4×CH 2(CH 3) 2)，1.28-1.07(24H，m，4×CH(CH 3) 2)。
Glucose-1,2,3,6-four-O-isobutyrate
FAB?mass：488[M+Na] +
H-NMR (δ, CDCl 3): 6.35 (1H, d, J3.61-H), 5.39 (1H, t, J10,3-H), 5.12 (1H, dd, J10 and 3.5,2-H), 4.61-4.52 (2H, m, 6-H), 3.99 (1H, ddd, J10,4 and 2.5,5-H), 3.60 (1H t, J10,4-H), 2.76-2.40 (4H, m, 4 * CH 2(CH 3) 2), 1.31-1.11 (24H, m, 4 * CH (CH 3) 2).
Glucose-1,2,4,6-four-O-isobutyrate
FAB?mass：488[M+Na] +
H-NMR (δ, CDCl 3): 6.33 (1H, d, J3.6,1-H), 5.05-4.99 (2H, m, 2,4-H), 4.18 (1H, dd, J10 and 3.5,2-H), 4.61-4.52 (2H, m, 6-H), 3.99 (1H, ddd, J10,4 and 2.5, and 5-H) 3.60 (1H, t, J10,4-H), 2.32-2.14 (8H, m, 4 * CH 2CH (CH 3) 2).1.01-0.9(24H，m，4×CH 2CH(CH 3) 2)。
Glucose-1,3,6-three-O-isobutyrate
FAB?mass：418[M+Na] +
H-NMR (δ, CDCl 3): 6.35 (1H, d, J3.6,1-H), 5.01 (1H, t, J9.8,3-H), 4.53 (2H, m, 6-H), 3.98 (2H, ddd, J9.8,4 and 2.5,5-H), 3.58 (1H, m, 4-H), 3.60 (1H, t, J9.8,2-H), 2.30-2.13 (6H, m, 3 * CH 2CH (CH 3) 2), 2.12-2.03 (4H, m, 3 * CH 2CH (CH 3) 2), 1.00-0.89 (18H, m, 3 * CH 2CH (CH 3) 2).
Synthetic embodiment 3 (sucrose isovalerate derivant synthesis example)
Use the cane sugar substitution glucose, whipping temp is changed into 80 ℃, and other technology is identical with synthetic embodiment 1, obtains 12.3g grease.The grease of gained separates with silica gel column chromatography and purify (ethyl acetate/hexane 1: 6) obtains: 2.3g sucrose-2,3,4,7,8,10,11,12-eight-O-isovalerate (Rf=0.83, productive rate: 15.8%), 1.8g sucrose-2,4,7,8,10,11,12-seven-O-isovalerate (Rf=0.70, productive rate: 13.4%), 1.3g sucrose-3,7,8,10,11,12-six-O-isovalerate (Rf=0.62, productive rate: 10.6%).
The above-mentioned sucrose isovalerate derivant that obtains uses the method identical with synthesizing embodiment 1 to identify.
Sucrose-2,3,4,7,8,10,11,12-eight-O-isovalerate
FAB?mass：1014[M+Na] +
H-NMR(δ，CDCl 3)：5.46(1H，m，5-H)，5.42(1H，d，J3.9，7-H)，5.35(1H，t，J8，8-H)，4.83(1H，t，J9.9，2-H)，4.80(1H，m，4-H)，4.51(1H，t，J9.9，3-H)，4.21(2H，m，12-H)，4.13(1H，m，1-H)，4.10(2H，m，11-H)，4.06(1H，m，9-H)，3.95(1H，m，5-H)，2.19-2.10(16H，m，8×CH 2CH(CH 3) 2)，2.02-1.96(8H，m，8×CH 2CH(CH 3) 2)，0.90-0.7(48H，m，4×CH 2CH(CH 3) 2)。
Sucrose-2,4,7,8,10,11,12-seven-O-isovalerate
FAB?mass：953[M+Na] +
H-NMR(δ，CDCl 3)：5.47(1H，m，5-H)，5.43(1H，d，J3.9，7-H)，5.35(1H，t，J8，8-H)，4.83(1H，t，J9.9，2-H)，4.83(1H，m，4-H)，4.51(2H，t，12-H)，4.13(1H，m，1-H)，4.12(2H，m，11-H)，4.08(1H，m，9-H)，3.95(2H，m，10-H)，3.84(1H，t，J9.9，3-H)，2.19-2.10(14H，m，4×CH 2CH(CH 3) 2)，2.02-1.98(7Hm，7×CH 2CH(CH 3) 2)，0.91-0.75(42H，m，7×CH 2CH(CH 3) 2)。
Sucrose-3,7,8,10,11,12-six-O-isovalerate
FAB?mass：869[M+Na] +
H-NMR(δ，CDCl 3)：5.45-5.46(2H，m，5，7-H)，5.42(1H，t，J9.9，8-H)，5.00(1H，t，J8，3-H)，4.51(1H，m，11-H)，4.37(2H，m，12-H)，4.36-4.21(4H，m，10，11，12-H)，4.17(1H，m，9-H)，4.05(1H，d，J3.8，1-H)，3.57(1H，m，4-H)，3.39(1H，t，J9.9，3-H)，2.19-2.10(12H，m，6×CH 2CH(CH 3) 2)，2.02-1.96(7H，m，6×CH 2CH(CH 3) 2)，0.91-0.75(42H，m，6×CH 2CH(CH 3) 2)。
Synthetic embodiment 4 (sucrose acetate isobutyrate ester derivant synthesis example)
Except substituting anhydrous isovaleric acid with anhydrous isopropylformic acid., other technology is identical with synthetic embodiment 3, obtains 12.8g grease.The grease of gained separates with silica gel column chromatography (ethyl acetate/hexane 1: 6) purifies, and obtains 2.0g sucrose-2,3,4,7,8,10,11,12-eight-O-isobutyrate (Rf=0.83, productive rate: 16.8%), 1.5g sucrose-2,4,7,8,10,11,12-seven-O-isobutyrate (Rf=0.70, productive rate: 10.4%), 1.2g sucrose-3,7,8,10,11,12-six-O-isobutyrate (Rf=0.62, productive rate: 10.1%).
The sucrose acetate isobutyrate ester derivant that obtains uses the method identical with synthesizing embodiment 1 to identify.
Sucrose-2,3,4,7,8,10,11,12-eight-O-isovalerate
FAB?mass：925[M+Na] +
H-NMR(δ，CDCl 3)：5.46(1H，m，5-H)，5.39(1H?d，J3.9，7-H)，5.32(1H，t，J8，8-H)，4.82(1H，t，J9.8，2-H)，4.81(1H，m，4-H)，4.53(1H，t，J9.8，3-H)，4.22(2H，m，12-H)，4.12(1H，m，1-H)，4.11(2H，m，11-H)，4.07(1H，m，9-H)，3.95(1H，m，5-H)，2.78-2.41(8H，m，8×CH 2(CH 3) 2)，1.20-1.08(24H，m，8×CH(CH 3) 2)。
Sucrose-2,4,7,8,10,11,12-seven-O-isovalerate
FAB?mass：855[M+Na] +
H-NMR(δ，CDCl 3)：5.49(1H，m，5-H)，5.44(1H，d，J3.9，7-H)，5.34(1H，t，J8，8-H)，4.85(1H，t，J9.9，2-H)，4.82(1H，m，4-H)，4.21(2H，m，12-H)，4.12(1H，m，1-H)，4.10(2H，m，11-H)，4.08(1H，m，9-H)，3.95(2H，m，10-H)，3.82(1H，t，J9.9，3-H)，2.19-2.10(14H，m，7×CH 2CH(CH 3) 2)，2.76-2.40(7H，m，7×CH 2(CH 3) 2)，1.31-1.11(42H，m，7×CH(CH 3) 2)。
Sucrose-7,8,10,11,12-six-O-isovalerate
FAB?mass：785[M+Na] +
H-NMR(δ，CDCl 3)：5.45-5.46(2H，m，5，7-H)，5.42(1H，t，J9.9，8-H)，5.00(1H，t，J8，3-H)，4.51(1H，m，11-H)，4.37(2H，m，12-H)，4.36-4.21(4H，m，10，11，12-H)，4.17(1H，m，9-H)，4.05(1H，d，J3.8，1-H)，3.57(1H，m，4-H)，3.39(1H，t，J9.9，3-H)，2.76-2.40(6H，m，6×CH 2(CH 3) 2)，1.31-1.11(36H，m，6×CH(CH 3) 2)。
Experimental example
Will be according to synthetic embodiment 1-4 synthetic glucose acyl substituted derivant and sucrose acyl substituted derivant and hydroquinone aqueous solution adding B-16 mouse melanoma cell culture fluid (Lotan R.; Lotan D.Cancer Res.40:3345-3350; 1980) in, carry out the test of whitening of cellular level.According to the mixture of synthetic embodiment 1-4 synthetic compound, separate the unification compound of purifying, and the ultimate density of hydroquinone is set according to table 1-4.Said mixture, unification compound and hydroquinone add respectively in the B-16 mouse melanoma cell culture medium to be cultivated 3 days.Cultured cells is handled with insulin and is separated from culture dish.Centrifugal separating cell extracts melanin.
1ml sodium hydroxide solution (concentration is 1N) joins in the above-mentioned extract, and the mixture boiled that obtains 10 minutes is so that dissolving melanin.Then, in the melanic absorptance of 400nm wavelength measurement, draw per unit cell number (10 with spectrophotometer thus 6Cell) the melanic amount that generates in.Melanic amount that the matched group that provides by table 1-4 generates and then calculating suppression ratio.
Separated and each chemical compound of purifying is described below according to synthetic embodiment 1-4:
Glucose-1,2,3,4,6-five-O-isovalerate: Glu-5-iV
Glucose-1,2,3,4-four-O-isovalerate: Glu-4-iV-1
Glucose-1,2,4,6-four-O-isovalerate: Glu-4-iV-2
Glucose-1,2,3,6-four-O-isovalerate: Glu-4-iV-3
Glucose-1,3,6-three-O-isovalerate: Glu-3-iV
Glucose-1,2,3,4,6-five-O-isobutyrate: Glu-5-iB
Glucose-1,2,3,4-four-O-isobutyrate: Glu-4-iB-1
Glucose-1,2,4,6-four-O-isobutyrate: Glu-4-iB-2
Glucose-1,2,3,6-four-O-isobutyrate: Glu-4-iB-3
Glucose-1,3,6-three-O-isobutyrate: Glu-3-iB
Sucrose-2,3,4,7,8,10,11,12-eight-O-isovalerate: Su-8-iV
Sucrose-2,4,7,8,10,11,12-seven-O-isovalerate: Su-7-iV
Sucrose-3,7,8,10,11,12-six-O-isovalerate: Su-6-iV
Sucrose-2,3,4,7,8,10,11,12-eight-O-isobutyrate: Su-8-iB
Sucrose-2,4,7,8,10,11,12-seven-O-isobutyrate: Su-7-iB
Sucrose-3,7,8,10,11,12-six-O-isobutyrate: Su-6-iB
Table 1
Test material Ultimate density (μ g/ml) Generate melanic amount Suppression ratio (%)
Matched group ????0 ????0.047±0.004 ????-
Hydroquinone ????1 ????0.025±0.002 ????46
????5 Exhaust ????-
Glucose isovalerate derivant (synthetic embodiment 1) mixture ????1 ????0.035±0.002 ????25
????5 ????0.029±0.003 ????38
????20 ????0.026±0.004 ????45
????Glu-5-iV ????1 ????0.029±0.002 ????38
????5 ????0.026±0.002 ????45
????20 ????0.015±0.002 ????68
????Glu-4-iV-1 ????1 ????0.034±0.002 ????28
????5 ????0.029±0.003 ????38
????20 ????0.025±0.002 ????47
????Glu-4-iV-2 ????1 ????0.032±0.002 ????32
????5 ????0.024±0.003 ????49
????20 ????0.020±0.002 ????57
????Glu-4-iV-3 ????1 ????0.033±0.002 ????30
????5 ????0.026±0.003 ????45
????20 ????0.022±0.002 ????53
??????Glu-3-iV ????1 ????0.035±0.003 ????25
????5 ????0.027±0.002 ????46
????20 ????0.024±0.004 ????49
Table 2
Test material Ultimate density (μ g/ml) Generate melanic amount Suppression ratio (%)
Matched group ????0 ????0.047±0.004 ????-
Hydroquinone ????1 ????0.025±0.002 ????46
????5 Exhaust ????-
Glucose isobutyrate derivant (synthetic embodiment 2) mixture ????1 ????0.039±0.002 ????17
????5 ????0.030±0.002 ????36
????20 ????0.023±0.004 ????51
????Glu-5-iB ????1 ????0.038±0.003 ????19
????5 ????0.030±0.002 ????36
????20 ????0.022±0.002 ????53
????Glu-4-iB-1 ????1 ????0.037±0.002 ????21
????5 ????0.029±0.003 ????38
????20 ????0.025±0.002 ????47
????Glu-4-iB-2 ????1 ????0.035±0.003 ????25
????5 ????0.030±0.003 ????36
????20 ????0.024±0.002 ????49
????Glu-4-iB-3 ????1 ????0.036±0.003 ????23
????5 ????0.029±0.003 ????38
????20 ????0.022±0.002 ????53
????Glu-3-iB ????1 ????0.038±0.003 ????19
????5 ????0.027±0.002 ????43
????20 ????0.023±0.004 ????51
Table 3
Test material Ultimate density (μ g/ml) The amount of synthesis of melanin Suppression ratio (%)
Matched group ????0 ????0.047±0.003 ????-
Hydroquinone ????1 ????0.025±0.002 ????46
????5 Exhaust ????-
Sucrose isovalerate derivant (synthetic embodiment 3) mixture ????1 ????0.037±0.003 ????21
????5 ????0.030±0.002 ????36
????20 ????0.026±0.004 ????45
????Su-8-iV ????1 ????0.036±0.002 ????23
????5 ????0.028±0.002 ????40
????20 ????0.024±0.002 ????49
????Su-7-iV ????1 ????0.033±0.002 ????30
????5 ????0.026±0.003 ????45
????20 ????0.021±0.002 ????55
????Su-6-iV ????1 ????0.035±0.002 ????25
????5 ????0.028±0.003 ????40
????20 ????0.026±0.002 ????45
Table 4
Test material Ultimate density (μ g/ml) The amount of synthesis of melanin Suppression ratio (%)
Matched group ????0 ????0.047±0.003 ????-
Hydroquinone ????1 ????0.025±0.002 ????46
????5 Exhaust ????-
Sucrose acetate isobutyrate ester derivant (synthetic embodiment 4) mixture ????1 ????0.038±0.003 ????21
????5 ????0.031±0.002 ????34
????20 ????0.025±0.004 ????47
????Su-8-iB ????1 ????0.036±0.002 ????23
????5 ????0.028±0.002 ????40
????20 ????0.024±0.003 ????49
????Su-7-iB ????1 ????0.037±0.002 ????30
????5 ????0.027±0.004 ????45
????20 ????0.023±0.003 ????51
????Su-6-iB ????1 ????0.035±0.003 ????25
????5 ????0.029±0.002 ????38
????20 ????0.027±0.002 ????43
With reference to table 1-4 as can be seen, with respect to matched group, glucose acyl substituted derivant and sucrose acyl substituted derivant can suppress the melanic generation of mouse melanoma cell of cultivating efficiently.Glucose-1,2,3,4 particularly, 6-five-O-isovalerate can suppress melanic generation efficiently.Test on the other hand,, when concentration surpasses 1 μ g/ml, then has serious cellulotoxic side effect, so can't be carried out although hydroquinone also can suppress melanic generation efficiently.On the contrary, still there be not cytotoxicity up to 20 μ g/ml according to the derivant of the derivant of glucose acyl substituted provided by the invention and sucrose acyl substituted when concentration, so be to have to suppress the synthetic ability of melanin efficiently.
The cosmetics of provided interpolation that the trier shows below glucose acyl derivative and sucrose acyl derivative are such as the sedimentary effect of inhibition skin pigment of external cream, facial cream, gentle skin emulsion, nutritional emulsions, makeup cream or essence etc.
Embodiment 1 and reference examples 1
The external cream that composition is as described in Table 5
Table 5
Composition (weight %) Embodiment 1 Reference examples 1
????a ????b ????c ????d ????e
????Glu-5-iV ????1
????Glu-4-iV-2 ????1
????Glu-5-iB ????1
????Su-7-iV ????1
????Su-7-iB ????1
Ethyl sebacate (Diethyl sebacate) ????8 ????8 ????8 ????8 ????8 ????8
Whale oil (Spermaceti) ????5 ????5 ????5 ????5 ????5 ????5
Polyoxyl 10 oleyl ether phosphate (Polyoxyethylene oleylether phosphate) ??6 ??6 ??6 ??6 ??6 ?6
Sodium Benzoate In right amount In right amount In right amount In right amount In right amount In right amount
Vaseline Add to 100 Add to 100 Add to 100 Add to 100 Add to 100 Add to 100
Embodiment 2 and reference examples 2
The facial cream that composition is as described in Table 6
Table 6
Composition (weight %) Embodiment 2 Reference examples 2
????a ????b ????c ????d ????e
????Glu-5-iV ????0.1
????Glu-4-iV-2 ????0.1
????Glu-5-iB ????0.1
????Su-7-iV ????0.1
????Su-7-iB ????0.1
Stearic acid ????1.0 ????1.0 ????1.0 ????1.0 ????1.0 ????1.0
Hexadecanol ????2.0 ????2.0 ????2.0 ????2.0 ????2.0 ????2.0
????PEG-20 ????1.0 ????1.0 ????1.0 ????1.0 ????1.0 ????1.0
Sorbitan monostearate (Sorbitan monostearate) ????1.0 ????1.0 ????1.0 ????1.0 ????1.0 ????1.0
Mineral oil ????10.0 ????10.0 ????10.0 ????10.0 ????10.0 ????10.0
Three monooctyl esters (Trioctanoate) ????5.0 ????5.0 ????5.0 ????5.0 ????5.0 ????5.0
Triethanolamine ????0.5 ????0.5 ????0.5 ????0.5 ????0.5 ????0.5
Carbomer (Carbomer) ????0.2 ????0.2 ????0.2 ????0.2 ????0.2 ????0.2
Glycerol ????5.0 ????5.0 ????5.0 ????5.0 ????5.0 ????5.0
Propylene glycol ????3.0 ????3.0 ????3.0 ????3.0 ????3.0 ????3.0
Antiseptic In right amount In right amount In right amount In right amount In right amount In right amount
Aromatic substance In right amount In right amount In right amount In right amount In right amount In right amount
Water Add to 100 Add to 100 Add to 100 Add to 100 Add to 100 Add to 100
Embodiment 3 and reference examples 3
The gentle skin emulsion that composition is as described in Table 7
Table 7
Composition (weight %) Embodiment 3 Reference examples 3
????a ????b ????c ????d ????e
????Glu-5-iV ????0.1
????Glu-4-iV-2 ????0.1
????Glu-5-iB ????0.1
????Su-7-iV ????0.1
????Su-7-iB ????0.1
Ethanol ????10.0 ????10.0 ????10.0 ????10.0 ????10.0 ????10.0
The hard Oleum Ricini of polyoxyethylene (Polyoxyethylene hardened caster-oil) ????1.0 ????1.0 ????1.0 ????1.0 ????1.0 ????1.0
Methyl butex ????0.2 ????0.2 ????0.2 ????0.2 ????0.2 ????0.2
Glycerol ????5.0 ????5.0 ????5.0 ????5.0 ????5.0 ????5.0
1,3 butylene glycol ????6.0 ????6.0 ????6.0 ????6.0 ????6.0 ????6.0
Aromatic substance In right amount In right amount In right amount In right amount In right amount In right amount
Pigment In right amount In right amount In right amount In right amount In right amount In right amount
Water Add to 100 Add to 100 Add to 100 Add to 100 Add to 100 Add to 100
Embodiment 4 and reference examples 4
The essence that composition is as described in Table 8
Table 8
Composition (weight %) Embodiment 4 Reference examples 4
????a ????b ????c ????d ????e
????Glu-5-iV ????0.5
????Glu-4-iV-2 ????0.5
????Glu-5-iB ????0.5
????Su-7-iV ????0.5
????Su-7-iB ????0.5
Propylene glycol ????10.0 ????10.0 ????10.0 ????10.0 ????10.0 ????10.0
Glycerol ????10.0 ????10.0 ????10.0 ????10.0 ????10.0 ????10.0
Aqueous solution of sodium hyaluronate (1%) (Sodium hyaluronic acid aquous solution) ????5.0 ????5.0 ????5.0 ????5.0 ????5.0 ????5.0
Ethanol ????5.0 ????5.0 ????5.0 ????5.0 ????5.0 ????5.0
The hard Oleum Ricini of polyoxyethylene ????1.0 ????1.0 ????1.0 ????1.0 ????1.0 ????1.0
Methyl butex ????0.1 ????0.1 ????0.1 ????0.1 ????0.1 ????0.1
Carbomer ????0.4 ????0.4 ????0.4 ????0.4 ????0.4 ????0.4
Aromatic substance In right amount In right amount In right amount In right amount In right amount In right amount
Water Add to 100 Add to 100 Add to 100 Add to 100 Add to 100 Add to 100
Embodiment 5 and reference examples 5
The change shape cream that composition is as described in Table 9
Table 9
Composition (weight %) Embodiment 5 Reference examples 5
????a ????b ????c ????d ????e
????Glu-5-iV ????0.1
????Glu-4-iV-2 ????0.1
????Glu-5-iB ????0.1
????Su-7-iV ????0.1
????Su-7-iB ????0.1
Glycerol ????5.0 ????5.0 ????5.0 ????5.0 ????5.0 ????5.0
Propylene glycol ????4.0 ????4.0 ????4.0 ????4.0 ????4.0 ????4.0
Polyvinyl alcohol ????15.0 ????15.0 ????15.0 ????15.0 ????15.0 ????15.0
Ethanol ????8.0 ????8.0 ????8.0 ????8.0 ????8.0 ????8.0
The hard Oleum Ricini of polyoxyethylene ????1.0 ????1.0 ????1.0 ????1.0 ????1.0 ????1.0
Polyoxyl 10 oleyl ether phosphate ????1.0 ????1.0 ????1.0 ????1.0 ????1.0 ????1.0
Methyl butex ????0.2 ????0.2 ????0.2 ????0.2 ????0.2 ????0.2
Aromatic substance In right amount In right amount In right amount In right amount In right amount In right amount
Pigment In right amount In right amount In right amount In right amount In right amount In right amount
Water Add to 100 Add to 100 Add to 100 Add to 100 Add to 100 Add to 100
Embodiment 6 and reference examples 6
The nutritional emulsions that composition is as described in Table 10
Table 10
Composition (weight %) Embodiment 6 Reference examples 6
????a ????b ????c ????d ????e
????Glu-5-iV ????0.01
????Glu-4-iV-2 ????0.01
????Glu-5-iB ??0.01
????Su-7-iV ????0.01
????Su-7-iB ????0.01
The hard Oleum Ricini of polyoxyethylene ????1.0 ????1.0 ????1.0 ????1.0 ????1.0 ????1.0
Methyl butex In right amount In right amount In right amount In right amount In right amount In right amount
Glycerol ????6.0 ????6.0 ????6.0 ????6.0 ????6.0 ????6.0
1,3 butylene glycol ????5.0 ????5.0 ????5.0 ????5.0 ????5.0 ????5.0
Carbomer ????0.2 ????0.2 ????0.2 ????0.2 ????0.2 ????0.2
Triethanolamine ????0.3 ????0.3 ????0.3 ????0.3 ????0.3 ????0.3
Propylene glycol ????5.0 ????5.0 ????5.0 ????5.0 ????5.0 ????5.0
Ethanol ????3.2 ????3.2 ????3.2 ????3.2 ????3.2 ????3.2
Carbomer ????0.1 ????0.1 ????0.1 ????0.1 ????0.1 ????0.1
Pigment In right amount In right amount In right amount In right amount In right amount In right amount
Aromatic substance In right amount In right amount In right amount In right amount In right amount In right amount
Water Add to 100 Add to 100 Add to 100 Add to 100 Add to 100 Add to 100
The measure of merit step is as follows.
At first, adhering to one at everyone forearm of 20 healthy male and women has the two rows aluminium foil in totally six diameter 7mm holes, and accepting power in distance arm 10 centimeters is that 1000 watts cold quartz mercury vapor lamp intensity is 60mJ/cm 2Irradiate light.Illuminated position is cleaned with 70% alcoholic solution at pre-irradiation.,, apply on six pairs of holes that are being divided into two rows for twice every day respectively to back 3 week of irradiation from pre-irradiation 3 days with cosmetics group and the described cosmetics of matched group 1-6 of embodiment 1-6.Pomade is cleaned out after experiment finishes 15 minutes among the embodiment 5.
According to the above embodiments, the pigementation degree is to be judged by bore hole, and the pigementation inhibition degree of cosmetics group and matched group is compared one to one.The result is divided into following three kinds, significant effective A, and effectively B does not have different C, and is listed in the table 11.
Table 11
The test group Embodiment 1 Embodiment 2 Embodiment 3 Embodiment 4 Embodiment 5 Embodiment 6
??A ??B ??C ??A ??B ??C ??A ??B ??C ??A ??B ??C ??A ??B ??C ??A ??B ??C
??A(Glu-5-iV) ??5 ??9 ??6 ??9 ??8 ??7 ??6 ??9 ??5 ??7 ??9 ??4 ??5 ??9 ??6 ??6 ??8 ??6
??B(Glu-4-iV-2) ??2 ??8 ??10 ??3 ??9 ??8 ??6 ??6 ??8 ??3 ??8 ??9 ??3 ??6 ??11 ??3 ??6 ??9
??C(Glu-5-iB) ??1 ??9 ??10 ??3 ??8 ??9 ??5 ??5 ??10 ??3 ??9 ??8 ??5 ??8 ??7 ??6 ??7 ??7
??D(Su-7-iV) ??3 ??5 ??12 ??5 ??8 ??7 ??5 ??7 ??8 ??3 ??9 ??8 ??4 ??8 ??8 ??4 ??7 ??9
??E(Su-7-iB) ??4 ??8 ??8 ??3 ??9 ??8 ??4 ??9 ??7 ??5 ??10 ??5 ??4 ??9 ??7 ??3 ??10 ??7
As described in Table 11; the relative ordinary cosmetics of cosmetics that contains glucose or sucrose acyl derivative as embodiment 1-6 has better skin-whitening effect; in the cosmetics of embodiment 1a-6a; contain glucose-1; 2; 3,4, the cosmetics of 6-five-O-isovalerate (Glu-5-iV) have best skin-whitening effect.
Industrial applicibility
As mentioned above; provided by the present inventionly contain the glucose acyl derivative or the sucrose acyl derivative is easy to synthesize; skin is free from side effects, can suppresses the pigementation of skin by restriction melanin synthesizing efficient, the cosmetics that contain such material can be used to skin-whitening.
The detailed description that the embodiment of the invention provides, those skilled in the art do based on this and modify and replace, and do not exceed spirit of the present invention and protection domain that claim of the present invention is illustrated.

Claims (5)

1. a cosmetic for skin whitening is characterized in that containing the glucose acyl substituted derivant that the following Chemical formula 1 of being selected from of effective dose is represented, a kind of in sucrose acyl substituted derivant that following Chemical formula 2 is represented and their mixture,
Chemical formula 1:
Figure A018215150002C1
In Chemical formula 1, radicals R is represented hydrogen atom or is had the acyl group of 3-6 carbon, and the number of acyl group is 3-5;
Chemical formula 2:
In Chemical formula 2, radicals R is represented hydrogen atom or is had the acyl group of 3-6 carbon, and the number of acyl group is 6-8.
2. cosmetic for skin whitening according to claim 1 is characterized in that: described glucose acyl substituted derivant is a glucose-1,2,3,4,6-five-O-isovalerate.
3. cosmetic for skin whitening according to claim 1 is characterized in that: described glucose acyl substituted derivant is selected from a kind of of following material, glucose-1,2; 3,4-four-O-isovalerate, glucose-1,2; 4,6-four-O-isovalerate, glucose-1,2; 3,6-four-O-isovalerate, glucose-1,3; 6-three-O-isovalerate, glucose-1,2,3; 4,6-five-O-isobutyrate, glucose-1,2; 3,4-four-O-isobutyrate, glucose-1,2; 4,6-four-O-isobutyrate, glucose-1,2; 3,6-four-O-isobutyrate, glucose-1; 3,6-three-O-isobutyrate, and composition thereof.
4. cosmetic for skin whitening according to claim 1 is characterized in that: described sucrose acyl substituted derivant is selected from a kind of of following material, sucrose-2,3,4; 7,8,10,11,12-eight-O-isovalerate; sucrose-2,4,7,8,10; 11,12-seven-O-isovalerate, sucrose-3,7,8; 10,11,12-six-O-isovalerate, sucrose-2,3; 4,7,8,10; 11,12-eight-O-isobutyrate, sucrose-2,4; 7,8,10,11; 12-seven-O-isobutyrate, sucrose-3,7,8; 10,11,12-six-O-isobutyrate, and composition thereof.
5. cosmetic for skin whitening according to claim 1 is characterized in that: be selected from described glucose acyl substituted derivant, a kind of 0.0001-15% that accounts for the cosmetics gross weight in sucrose acyl substituted derivant and their mixture.
CNB018215157A 2000-12-30 2001-12-26 Cosmetic for skin whitening containing acyl substituted derivatives of glucose or sucrose Expired - Fee Related CN1229107C (en)

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JP2004517109A (en) 2004-06-10

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