alpha-Antiarin

Title: a-Antiarin
CAS Registry Number: 23605-05-2
CAS Name: (3b,5b,12b)-3-[(6-Deoxy-b-D-gulopyranosyl)oxy]-5,12,14-trihydroxy-19-oxocard-20(22)-enolide
Molecular Formula: C29H42O11
Molecular Weight: 566.64
Percent Composition: C 61.47%, H 7.47%, O 31.06%
Literature References: From latex (arrow poison) of the upas tree, Antiaris toxicaria Lesch., Moraceae, found in Indonesia: Taylor, Br. J. Pharmacol. 8, 237 (1953). Older literature and isoln: Doebel et al., Helv. Chim. Acta 31, 688 (1948); Dolder et al., ibid. 38, 1364 (1955). Structure of aglycone: Martin, Tamm, ibid. 42, 696 (1959). The sugar portion of a-antiarin is antiarose (D-gulomethylose), while that of the isomeric b-antiarin is L-rhamnose. Structure: Juslén et al., ibid. 45, 2285 (1962). Toxicity: Chen, Henderson, J. Pharmacol. Exp. Ther. 150, 53 (1965).
Properties: Tetrahydrate, crystals (six-sided leaflets) from water. Anhydrous after 3 hrs at 110° in high vac, dec 238-240°. [a]D17 -3.9° (c = 0.905 in methanol). Sol in water, alcohol, slightly in ether. uv max: 305, 217 nm (log e 1.8, 4.08). MLD (anhydr compd) in cats (mg/kg): 0.116 i.v. (Chen, Henderson).
Optical Rotation: [a]D17 -3.9° (c = 0.905 in methanol)
Absorption maximum: uv max: 305, 217 nm (log e 1.8, 4.08)
Toxicity data: MLD (anhydr compd) in cats (mg/kg): 0.116 i.v. (Chen, Henderson)
Derivative Type: Tribenzoate
Molecular Formula: C50H54O14
Molecular Weight: 878.96
Percent Composition: C 68.32%, H 6.19%, O 25.48%
Properties: Needles from methanol, mp 240°. [a]D21 +3.0° (acetone). Practically insol in water, very sparingly sol in methanol, ethanol, ether. Freely sol in acetone, chloroform.
Melting point: mp 240°
Optical Rotation: [a]D21 +3.0° (acetone)
Status: This monograph has been retired and is no longer subject to revision or update.
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