CAS No 479-98-1 , b-D-Glucopyranoside,(1S,4aR,5S,7aS)-1,4a,5,7a-tetrahydro-5-hydroxy-7-(hydroxymethyl)cyclopenta[c]pyran-1-yl

Title: Aucubin
CAS Registry Number: 479-98-1
CAS Name: [1S-(1a,4aa,5a,7aa)]-1,4a,5,7a-Tetrahydro-5-hydroxy-7-(hydroxymethyl)cyclopenta[c]pyran-1-yl-b-D-glucopyranoside
Synonyms: rhinanthin; aucuboside
Molecular Formula: C15H22O9
Molecular Weight: 346.33
Percent Composition: C 52.02%, H 6.40%, O 41.58%
Literature References: From leaves, roots, stalks and seeds of Aucuba japonica Thunb., Cornaceae; also occurs in 75 different plants: Paris, Chaslot, Ann. Pharm. Fr. 13, 648 (1955). Isoln: Trim, Hill, Biochem. J. 50, 310 (1952); Rombouts, Links, Experientia 12, 78 (1956). Structure: Haegele et al., Tetrahedron Lett. 1961, 110; Birch et al., J. Chem. Soc. 1961, 5194. Abs config: A. Bianco et al., Gazz. Chim. Ital. 106, 725 (1976). Brief review of structural studies: J. M. Bobbitt, K.-P. Segebarth, "The Iridoid Glycosides and Similar Substances" in Cyclopentanoid Terpene Derivatives, W. I. Taylor, A. R. Battersby, Eds. (Marcel Dekker, New York, 1969) pp 25-31.
Properties: Crystals from ethanol + ether, mp 181°. [a]D21 -163.1° (c = 1.6). Soluble in water, alc, methanol; practically insol in chloroform, ether, petr ether. Absorption spectrum: Trim, Hill, loc. cit.
Melting point: mp 181°
Optical Rotation: [a]D21 -163.1° (c = 1.6)