Browse > Article
http://dx.doi.org/10.5012/bkcs.2003.24.8.1169

Synthesis of L-Ascorbic Acid Derivative Including 3-Aminopropane Phosphoric Acid as a Novel Whitening Agent  

Kang, Hak-Hee (Department of Chemical Engineering, College of Engineering, Hanyang University)
Oh, Seong-Geun (Department of Chemical Engineering, College of Engineering, Hanyang University)
Publication Information
Abstract
A stable derivative of L-ascorbic acid, 2-O-[(3-aminopropyl)phosphinooxy]-L-ascorbic acid (LAAP), was synthesized in moderate yield and its chemical stability and effects on melanin synthesis were investigated. LAscorbic acid was decomposed completely within about 1 hour, while 93% of LAAP remained even after 10 days. Treatment of L-ascorbic acid and LAAP decreased melanin content in normal human melanocytes to 33.8% and 49.1% of control at 2 mM, respectively. Considering chemical instability of L-ascorbic acid, LAAP is a much better whitening agent.
Keywords
2-O-[(3-Aminopropyl)phosphinooxy]-L-ascorbic acid (LAAP); Whitening agent;
Citations & Related Records
Times Cited By KSCI : 1  (Citation Analysis)
Times Cited By Web Of Science : 2  (Related Records In Web of Science)
Times Cited By SCOPUS : 2
연도 인용수 순위
1 Kim, D. H.; Hwang, J. S.; Baek, H. S.; Kim, K.-J.; Lee, B. G.;Chang, I. S.; Kang, H. H.; Lee, O. S. Chem. Pharm. Bull. 2003,51, 113.   DOI   ScienceOn
2 Kim, K.-J.; Kim, D. H.; Hong, J. E.; Chang, I. S.; Kang, H. H. J.Am. Oil Chem. Soc. 2001, 78, 441.   DOI   ScienceOn
3 Tomita, Y.; Hariu, A.; Mizuno, C.; Seiji, M. J. Invest. Dermatol.1980, 75, 379.   DOI   ScienceOn
4 Hearing, V. J.; Ekel, T. M. Biochem. J. 1976, 157, 549.
5 Edwards, S. M.; Donnelly, T. A.; Sayre, R. M.; Rheins, L. A.Photodermatol. Photoimmunol. Photomed. 1994, 10, 111.
6 Hwang, S-H.; Han, Y-S.; Choy, J-H. Bull. Korean Chem. Soc.2001, 22, 1019.
7 Jernow, J.; Blount, J.; Oliveto, E.; Perrota, A.; Rosen, P.; Toome,V. Tetrahedron 1979, 35, 1483.   DOI   ScienceOn
8 Lee, O. S.; Byon, Y. H.; Lee, B. S.; Hong, J. E.; Ko, J. S.; Cho, Y. K.; Lee, H. US Patent 5723645, 1998.
9 Kong, B.; Ueom, J.; Kim, I.; Lim, D.; Kang, J.; Lee, K. Bull.Korean Chem. Soc. 2002, 23, 1773.   DOI   ScienceOn
10 Davies, M. B.; Austin, J.; Partridge, D. A. Vitamine C: ItsChemistry and Biochemistry; The Royal Society of Chemistry:Cambridge, U. K., 1991.
11 Halliwell, B.; Gutteridge, J. M. C. Free Radicals in Biology andMedicine, 3rd Ed.; Oxford University Press: Oxford, U. K.,1988.
12 Kameyama, K.; Sakai, C.; Kondoh, S. J. Am. Acad. Dermatol.1996, 34, 29.   DOI   ScienceOn
13 Colven, R. M.; Pinnell, S. R. Clin. Dermatol. 1996, 14, 227.   DOI   ScienceOn
14 Aberdam, E.; Roméro, C.; Ortonne, J. P. J. Cell Sci. 1993, 106,1015.