Synthesis and Characterization of 6-O-Acyl-2-O-.ALPHA.-D-glucopyranosyl-L-ascorbic Acids with a Branched-acyl Chain.
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Accession number;03A0096295
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| Title;Synthesis and Characterization of 6-O-Acyl-2-O-.ALPHA.-D-glucopyranosyl-L-ascorbic Acids with a Branched-acyl Chain. |
| Author;
TAI A
(Okayama Univ., Okayama, Jpn)
KAWASAKI D
(Okayama Univ., Okayama, Jpn)
SASAKI K
(Okayama Univ., Okayama, Jpn)
GOHDA E
(Okayama Univ., Okayama, Jpn)
YAMAMOTO I
(Okayama Univ., Okayama, Jpn)
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Journal Title;Chem Pharm Bull
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Journal Code:G0504A
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ISSN:0009-2363
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VOL.51;NO.2;PAGE.175-180(2003)
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| Figure&Table&Reference;FIG.4, TBL.3, REF.34 |
| Pub. Country;Japan |
| Language;English |
| Abstract;We previously reported the chemical synthesis of a series of novel monoacylated vitamin C derivatives, 6-O-acyl-2-O-.ALPHA.-D-glucopyranosyl-L-ascorbic acids (6-Acyl-AA-2G) possessing a straight-acyl chain of varying length from C4 to C18, as effective skin antioxidants. In this paper, we describe branched type of 6-Acyl-AA-2G derivatives (6-bAcyl-AA-2G) synthesized by use of a 2-branched-chain fatty acid anhydride as an acyl donor. The stability of 6-bAcyl-AA-2G in neutral solution was much higher than that of 6-Acyl-AA-2G, while they were susceptible to enzymatic hydrolysis for exerting vitamin C effect. These branched derivatives as well as 6-Acyl-AA-2G increased the radical scavenging activity against 1,1-diphenyl-2-picrylhydrazyl and the lipophilicity in octanol/water-partitioning systems with increasing length of their acyl group. In addition, the 6-bAcyl-AA-2G derivative with an acyl chain of C12, 6-bDode-AA-2G had the excellent solubility to various solvents, suggesting easy handling in cosmetic use. These characteristics of 6-bAcyl-AA-2G may be available for skin care application as an effective antioxidant. (author abst.) |
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