Chemistry of ayurvedic crude drugs—III: Guggulu (resin from Commiphora mukul)-3 long-chain aliphatic tetrols, a new class of naturally occurring lipids
✍ Scribed by V.D. Patil; U.R. Nayak; Sukh Dev
- Book ID
- 104202992
- Publisher
- Elsevier Science
- Year
- 1973
- Tongue
- French
- Weight
- 422 KB
- Volume
- 29
- Category
- Article
- ISSN
- 0040-4020
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✦ Synopsis
Isolation and structure elucidation of two long-chain aliphatic tetrols, now formulated as octadecan-1,2,3&tetrol and eicosan-1,2,3&tetrol, from gum-resin of Commiphoru mukul, is described. There is evidence for the occurrence of nonadecan-1,2,3,Ctetrol, as well, in the resin. This is the hrst reported occurrence of such compounds in nature, though the closely related phytosphingosines (e.g. 2-amino-octadecan-1,3&triol) are well known. *Part II, Tetrahedron 29,341(1973). tCommunication No. 1689, National Chemical Laboratory, Poona.
Sin the earlier communication1 this material has been incorrectly reported as a mixture of long-chain aliphatic triols. This error arose from the diicultv in aettina the correct mol. wt. from mass spectra and, at that timi we considered the fourth oxygen atom to be located as an oxirane ring.
OMass spectra of the free tetrol and the tetra-acetate were not helpful in determining the mol. wt. of the species present. The tetrols always gave highest m/e peak corresponding to M + 1 + and this proved quite confusing in the early stages of the work; mass spectra of the pure tetrols are discussed later. Similarly, the mass spectrum of the tetra-acetate was also not simple to interpret.