Tutin

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.
Twistane Tybamate Tylocrebrine Tylophorine Tylosin

Tutin may refer to: