823. Asarinin

Nomenclature

CAS number: 133-04-0
5,5′-[(1R,3aS,4S,6aS)-Tetrahydro-1H,3H-furo[3,4-c]furan-1,4-diyl]bis-1,3-benzodioxole; l-asarinin; ()-episesamin; xanthoxylin S.
C20H18O6; mol wt 354.35.
C 67.79%, H 5.12%, O 27.09%.

Description and references

Naturally occurring l-form isolated from Xanthoxylum clava-herculis L. (X. carolinianum Lam.), Rutaceae; Asarum sieboldi Miguel var. seulensis Nakai, A. blumei Duch., Aristolochiaceae: Colton, Am. J. Pharm. 52, 191 (1880); Eberhardt, ibid. 62, 231 (1890); Gordin, J. Am. Chem. Soc. 28, 1649 (1906); H. Dieterle et al., Arch. Pharm. 269, 384 (1931); Huang-Minlon, Ber. 70, 951 (1937); T. Kaku et al., Keijo J. Med. 9, 1 (1934); C.A. 32, 90901 (1938). Structure: H. Dieterle, K. Schwenger, Arch. Pharm. 277, 33 (1939). Synthesis of dl-form: M. Beroza, M. S. Schechter, J. Am. Chem. Soc. 78, 1242 (1956); K. Freudenberg, E. Fischer, Ber. 89, 1230 (1956); D. R. Stevens, D. A. Whiting, Tetrahedron Lett. 27, 4629 (1986). Diastereoisomeric with sesamin, q.v. Stereochemistry of the d-form: K. Freudenberg, G. S. Sidhu, ibid. 94, 851 (1961). Antitubercular activity: Ramaswamy, Naturwissenschaften 44, 380 (1957).

Chemical structure

Properties

Crystals from alc, mp 121°. [α]D20 118.6°; [α]D23 122° (chloroform). Practically insol in water. Freely sol in boiling methanol, alcohol, chloroform, acetone, benzene.

Derivative

d-Form.

Nomenclature

Episesamin; (+)-episesamin.

Properties

Crystals from ethanol, mp 121.5°. [α]D25 +124° (chloroform).

Derivative

dl-Form.

Properties

Crystals, mp 134-135°.