6785-34-8Relevant articles and documents
Study on the bile salt, sodium scymnol sulfate, from Lamna distropis. III. The structures of a new sodium scymnol sulfate and new anhydroscymnols
Ishida,Kinoshita,Natsuyama,Nukaya,Tsuji,Nagasawa,Kosuge
, p. 864 - 868 (1992)
Two sodium scymnol sulfates, 1 and 2, were isolated by two steps of chromatography from the bile of Lamna ditropis. Compound 2 was identified as (24R,25S)-(+)-3α,7α,12α,24,26-pentahydroxy-5β-cholestan-27-yl sodium sulfate and the structure of 1 was determined to be (24R,25R)-(+)-3α,7α,12α,24,26-pentahydroxy-5β-cholestan-27-yl sodium sulfate, based on the spectral data and chemical transformations. Based on the physical data, the structures of two new anhydroscymnols, 3 and 4, prepared from 1 by alkaline degradation with aqueous potassium hydroxide, were established as (24R,25R)-(+)-24,26-epoxy-5β-cholestane-3α,7α,12α,27-tetrol and (24R)-(+)-26,27-epoxy-5β-cholestane-3α,7α,12α,24-tetrol, respectively. The other shark bile constituents were also analyzed, and the hydrolysis of the sulfate ester function of 1 and 2 was examined.
On the Synthesis of Scymnol
Amiet, R. Gary,Kalafatis, Nicole,Macrides, Theodore
, p. 1347 - 1354 (2007/10/02)
Reinvestigation of a reported synthesis of scymnol (5β-cholestane-3α,7α,12α,24,26,27-hexol) has cast doubt on the success of that synthetic route.A modified synthetic pathway has been developed and scymnol, racemic at C24, has been unequivocally prepared from cholic acid.Extensive proton and 13C n.m.r. spectroscopy has been used to confirm the strcuture of the product.A new, simple method of desulfation of natural scymnol sulfate has been developed.
Comparative studies of 'bile salts'. 14. Isolation from shark bile and partial synthesis of scymnol.
BRIDGWATER,BRIGGS,HASLEWOOD
, p. 285 - 290 (2007/10/10)
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