773. Arbutin

Nomenclature

CAS number: 497-76-7
4-Hydroxyphenyl-β-d-glucopyranoside; hydroquinone-β-d-glucopyranoside; hydroquinone glucose; arbutoside; ursin.
C12H16O7; mol wt 272.25.
C 52.94%, H 5.92%, O 41.14%.

Description and references

Naturally occurring glycoside of hydroquinone, q.v., found in the bark and leaves of various plants, usually occurring together with methylarbutin. Principal antibacterial constituent of the traditional medicine, uva ursi, q.v. Isoln from bearberry leaves (Arctostaphylos uva-ursi Spreng., Ericaceae): A. Kawalier, Ann. 82, 241 (1852); from leaves of blueberry, cranberry, and pear (Pyrus communis L., Rosaceae): G. Urban, M. Rogowski, Arch. Exp. Pathol. Pharmakol. 211, 194 (1950). Synthesis: C. Mannich, Arch. Pharm. 250, 547 (1912); A. Robertson, R. B. Waters, J. Chem. Soc. 1930, 2729. Production by plant cell culture: S. Inomata et al., Appl. Microbiol. Biotechnol. 36, 315 (1991). Physical properties: E. Lindpainter, Arch. Pharm. 277, 398 (1940). Determn in drug prepns: L. Kraus, Pharmazie 19, 41 (1964); E. Kenndler et al., J. Chromatogr. 514, 383 (1990). Inhibition of human melanin synthesis in vitro: K. Maeda, M. Fukuda, J. Pharmacol. Exp. Ther. 276, 765 (1996). Review of human exposure: P. J. Deisinger et al., J. Toxicol. Environ. Health 47, 31-46 (1996).

Chemical structure

Properties

Occurs as the monohydrate. Colorless elongated prisms from moist ethyl acetate, mp 199° after sintering at 163-164° (Robertson, Waters). Also reported as unstable form, mp 165°; stable form, mp 199.5-200° (Lindpaintner). [α]D20 60.3° (in water). Sol in water and in alc.

Derivative

Methylarbutin.

Nomenclature

CAS number: 6032-32-2
4-Methoxyphenyl-β-d-glucopyranoside; methylarbutoside.
C13H18O7; mol wt 286.28.
C 54.54%, H 6.34%, O 39.12%.

Properties

Crystallizes from water as the monohydrate, mp 158-160°; solidifies and melts again at 175° (Mannich). Also reported as unstable form, mp 160.5°; stable form, mp 176° (Lindpaintner). [α]D20 60.66° (in water). Sol in hot water or alcohol; slightly sol in ether.

Use

In cosmetics as skin lightening agent.