Paeoniflorin, a monoterpene glucoside of Chinese Paeony root

✍ Scribed by S. Shibata; N. Aimi; M. Watanabe

• Book ID: 104215035
• Publisher: Elsevier Science
• Year: 1964
• Tongue: French
• Weight: 202 KB
• Volume: 5
• Category: Article
• ISSN: 0040-4039
• DOI: 10.1016/s0040-4039(00)75129-x

✦ Synopsis

PAEONIFI,OFUN (I), obtained from Chinese Paeony root, has been found as being a glucoaide of bensoylated Clo-compound, whose eglycone cannot be obtained by the usual methods due to its instability to acid and resistance to enzymatic hydrolysis. It haa been reported previously (1.2) that monomethyl ether of desbensoyl paeoniflorin (IV) yields on acid hydrolysis &glucose and 2-(2,~dihydroxy-4_methylphenyl)propionic acid (XII). This aromatic acid (XI) was noted aa it retained all the ten carbon atoms of the assumed aglycone part of paeoniflorin which is by no means aromatic. By the action of LiAlH4, paeoniflorin tetraacetate and pentaacetate gave three products, C16H24010~ mp. 186', C16H2409, m.p. 163', and 01&,509, m.P. 267',which were tentatively named product Al (v), A2 (VI) and A3 (VII), respectively. The product Al (desbenaoyl paeoniflorin)(V), gave the aromatic compound (III) on acid hydrolysis,whereas the product A3 (VII) afforded a non-aromatic aglymne, C10H1604, m.p. 223' (VII').