Title: Tutin
CAS Registry Number: 2571-22-4
CAS Name: (1aS,1bS,2S,2¢R,5R,6S,6aR,7aR,8S)-Hexahydro-1b,6-dihydroxy-6a-methyl-8-(1-methylethenyl)spiro[2,5-methano-7H-oxireno[3,4]cyclopent[1,2-d]oxepin-7,2¢-oxiran]-3(2H)-one
Molecular Formula: C15H18O6
Molecular Weight: 294.30
Percent Composition: C 61.22%, H 6.16%, O 32.62%
Literature References: Poisonous constituent of Coriaria ruscifolia L. or C. japonica A. Gray, (tutu) Coriariaceae. Naturally occurring form is (+)-tutin. Isoln: Easterfield, Aston, J. Chem. Soc. 79, 125 (1901). Structure: Johns, Markham, ibid. 1961, 3006; Craven, Nature 197, 1193 (1963); Mackay, Mathieson, Tetrahedron Lett. 1963, 1399. Absolute configuration: Okuda, Yoshida, ibid. 1965, 2137. Biosynthesis: A. Corbella et al., Chem. Commun. 1969, 634. NMR analysis: J. W. Blunt et al., Aust. J. Chem. 32, 1339 (1979). Stereospecific synthesis: K. Watamatsu et al., Tetrahedron 42, 5551 (1986). Determn in toxic honey: J. L. Love et al., N.Z. J. Technol. 2, 179 (1986). Effect on central nervous system: D. R. Curtis et al., Brain Res. 63, 419 (1973); A. Nistri et al., Lancet 1, 996 (1974). Toxicity data: C. H. Jarboe et al., J. Med. Chem. 11, 729 (1968).
Properties: White, odorless crystals. mp 209-212°; also reported as mp 204-205° (Wakamatsu). [a]D20 +9.25° (alc); [a]D17 +13.9° (c = 0.75, methanol). Sol in water, alcohol, ether. LD50 i.p. in female mice: 3.0 mg/kg (Jarboe).
Melting point: mp 209-212°; mp 204-205° (Wakamatsu)
Optical Rotation: [a]D20 +9.25° (alc); [a]D17 +13.9° (c = 0.75, methanol)
Toxicity data: LD50 i.p. in female mice: 3.0 mg/kg (Jarboe)
Derivative Type: Diacetate
Molecular Formula: C19H22O8
Molecular Weight: 378.37
Percent Composition: C 60.31%, H 5.86%, O 33.83%
Properties: Crystals from ethanol-water, mp 197-201°.
Melting point: mp 197-201°
CAUTION: Poisoning from ingestion of C. ruscifolia has been reported and is due to presence of tutin. Symptoms include giddiness, stupor, coma, delirium, convulsions. |