The structure, stereochemistry and conformation of acacic acid

✍ Scribed by I.P. Varshney; K.M. Shamsuddin; R.E. Beyler

• Book ID: 104236190
• Publisher: Elsevier Science
• Year: 1965
• Tongue: French
• Weight: 389 KB
• Volume: 6
• Category: Article
• ISSN: 0040-4039
• DOI: 10.1016/s0040-4039(01)83995-2

✦ Synopsis

Recently the isolation of a new pentacyclic trlterpenic acid genin, Acacic acid, has been reported from barks, pods -and seeds of a number of Acacias and Albizzias 1,2 . Now on the basis of the transformations shown in Table I the structure of Acacic acid has been fixed as 8,16,21-trihydroxy-olean-12-ene-28-01~ acid (I). Earlier this structure (I) was assigned to acacic acid on the basis of its conversion to a product identified by mixed melting point with 28-nor-B-amyrin (nor-echlnocystenol A)2. It has now been found that this identification was in fact erroneous, but that the structure of acacic acid is nevertheless correctly represented by formula I. This has been arrived at on the basis of the following evidence. The relation of acacic acid to B-amyrin was fixed by formation of the diacetyl methyl ester of sapogenin ItBIt (VI) of Styphnodendron coriaceum3 from acacic acid (I).

* This paper is to be considered as Part XXVIII in our "Saponins and Sapogenins" series.