Title: Asarinin
CAS Registry Number: 133-04-0
CAS Name: [1R-(1a,3aa,4b,6aa)]-5,5¢-(Tetrahydro-1H,3H-furo[3,4-c]furan-1,4-diyl)bis-1,3-benzodioxole
Additional Names: l-asarinin; (-)-episesamin; xanthoxylin S
Molecular Formula: C20H18O6
Molecular Weight: 354.35
Percent Composition: C 67.79%, H 5.12%, O 27.09%
Literature 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).
Properties: Crystals from alc, mp 121°. [a]D20 -118.6°; [a]D23 -122° (chloroform). Practically insol in water. Freely sol in boiling methanol, alcohol, chloroform, acetone, benzene.
Melting point: mp 121°
Optical Rotation: [a]D20 -118.6°; [a]D23 -122° (chloroform)
Derivative Type: d-Form
Additional Names: Episesamin; (+)-episesamin
Properties: Crystals from ethanol, mp 121.5°. [a]D25 +124° (chloroform).
Melting point: mp 121.5°
Optical Rotation: [a]D25 +124° (chloroform)
Derivative Type: dl-Form
Properties: Crystals, mp 134-135°.
Melting point: mp 134-135°
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