Acetyloleanolic acid

The reduction of acyl halides with hydrogen to form aldehydes using Pd catalyst is well known as the Rosenmund reduction[756]. Some acyl chlorides give decarbonyiation products rather than aldehydes under Rosenmund conditions. The diene 890 was obtained by decarbonyiation in an attempted Rosenmund reduction of acetyloleanolic acid chloride (889)[757], Rosenmund reduction of sterically hindered acyl chlorides such as diphenyl- and tnpheny-lacetyl chloride (891) gives the decarbonylated products 892[758],... 

Carboxylic esters where R is methyl or ethyl can be cleaved by heating with lithium iodide in refluxing pyridine or a higher boiling amine. " The reaction is useful where a molecule is sensitive to acid and base (so that 10-10 cannot be used) or where it is desired to cleave selectively only one ester group in a molecule containing two or more. For example, refluxing O-acetyloleanolic acid methyl ester... 

Enhancement of the inhibitory activity was found in 3-oxo derivatives of 142 and 210, while either loss of oxygen functionality at C-3 of 210 or oxidation at C-3 of 147 led to the reduction of the activity [22]. Two 3-O-acetyl oleananes, 3-O-acetylerythrodiol (117 68% inhibition at lxlO3 mol ratio compound/TPA 80% cell viability) and acetyloleanolic acid (119 64% inhibition 80% viability), showed remarkable inhibitory effects with preserved higher viabilities of Raji cells than their free alcohols, erythrodiol (130 81% inhibition 50% viability) and 142 (70% inhibition 60% viability) [72]. Under the same assay conditions, betulinic acid (257) exhibited complete inhibition of activation with 80% cell viability [72]. Arjunolic acid triacetate (154 66% inhibition at lxl02 mol ratio compound/TPA) and arjunolic acid triacetate methylester (155 73%)... 

Acetylnaphthalene, 131 Acetyl nitrate, 13-14 O-Acetyloleanolic acid methyl ester, 616... 

Aleuritolic acid (191) from Aleuritus montma, was readily transformed by acid into acetyloleanolic acid. The corresponding ester yielded myricadiol (192) on reduction with lithium aluminium hydride. 

A compound from the seeds of Phytolacca americana, previously believed to be acetyloleanolic acid, has been identified as acetylaleuritolic acid (162), which has also been obtained from Jatropha macrorhiza. It has antitumour activity. The structure of marsformoxide B (163) from Marsdenia formosana has been... 

Chemical studies of numy other species of Randia have shown the presence of triterpenoid acids such as oleanolic add and randialic add. Previous work on the roots of R. siamensis yielded mesembryanthemoidigenic acid, 3-P-acetyloleanolic add, ursolic acid and 3-0-(a-L-arabinosyl)-oleanolic add (Lapikanom et al., 1983 Woo et al., 1984). However, there have been no previous reports of compounds isolated from the fhiit of this plant. 

Contains triterpenoids, including oleanolic acid (ligustrin, 0.7-. 3%), acetyloleanolic... 

Methyl 0-acetyloleanolate refluxed 8 hrs. with excess anhj drous Li-iodide in 2,4,6-collidine under N2, cooled to room temp., and poured on HCl-ice-ether-methylene chloride 0-acetyloleanic acid. Y 90%. F. e. in 2,6-lutidine s. F. Elsinger, J. Schreiber, and A. Eschenmoser, Helv. 43, 113 (1960) method s. E. Taschner and B. Liberek, Roczniki Chem. 30, 323 (1956). 

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