Title: Sesamin
CAS Registry Number: 607-80-7
CAS Name: 5,5¢-(Tetrahydro-1H,3H-furo[3,4-c]furan-1,4-diyl)bis-1,3-benzodioxole
Additional Names: tetrahydro-1,4-bis[3,4-(methylenedioxy)phenyl]-1H,3H-furo[3,4-c]furan; 2,6-bis(3,4-methylenedioxyphenyl)-3,7-dioxabicyclo[3.3.0]octane
Molecular Formula: C20H18O6
Molecular Weight: 354.35
Percent Composition: C 67.79%, H 5.12%, O 27.09%
Literature References: Isolated from the bark of various Fagara species; from sesame oil: Bertram et al., Biochem. Z. 197, 1 (1928); from fruit of Piper lowong Blume, Piperaceae: Peinemann, Arch. Pharm. 234, 238 (1896). Structure: Cohen, Rec. Trav. Chim. 57, 653 (1938). Synthesis of dl-form: Beroza, Schechter, J. Am. Chem. Soc. 78, 1242 (1956); Freudenberg, Naturwissenschaften 43, 16 (1956). Identity of dl-form with fagarol: Carnmalm, Acta Chem. Scand. 9, 1111 (1955); identity of d-form with pseudocubebin: idem, ibid. 10, 134 (1956). Stereochemistry of the d-isomer: Freudenberg, Sidhu, Ber. 94, 851 (1961); Becker, Beroza, Tetrahedron Lett. 1962, 157. Review: Budowski, J. Am. Oil Chem. Soc. 41, 280 (1964).
Derivative Type: d-Form
Properties: Needles from ethanol, mp 122-123°. [a]D20 +64.5° (c = 1.75 in chloroform).
Melting point: mp 122-123°
Optical Rotation: [a]D20 +64.5° (c = 1.75 in chloroform)
Derivative Type: dl-Form
Properties: Crystals from ethanol, mp 125-126°. Freely sol in chloroform, benzene, acetic acid, acetone. Practically insol in water, alkaline solns and hydrochloric acid.
Melting point: mp 125-126°
Use: Insecticide synergist. |