References of 1,3-Benzodioxole,5,5'-[(1R,3aS,4S,6aS)-tetrahydro-1H,3H-furo[3,4-c]furan-1,4-diyl]bis-
Title: Asarinin
CAS Registry Number: 133-04-0
CAS Name: [1
R-(1a,3aa,4b,6aa)]-5,5¢-(Tetrahydro-1
H,3
H-furo[3,4-
c]furan-1,4-diyl)bis-1,3-benzodioxole
Synonyms: 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
Synonyms: 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°