143615-30-9

Basic information

• Product Name: methyl 4-O-acetylshikimate
• CAS NO: 143615-30-9
• Molecular Weight: 230.218
• Mol File: 143615-30-9.mol
• Article Data: 5

Chemical Properties

• CAS DataBase Reference: methyl 4-O-acetylshikimate(CAS DataBase Reference)
• NIST Chemistry Reference: methyl 4-O-acetylshikimate(143615-30-9)
• EPA Substance Registry System: methyl 4-O-acetylshikimate(143615-30-9)

Safety Data

• Hazardous Substances Data: 143615-30-9(Hazardous Substances Data)

Upstream product

• 108-05-4 vinyl acetate 
• 40983-58-2 methyl shikimate 
• 138-59-0 shikimic acid 
• 566202-08-2 2-acetoxycinnamic anhydride 
• 83604-10-8 rac-methyl 5-hydroxycyclohexa-1,3-diene-1-carboxylate 
• 563-63-3 silver(I) acetate 

Relevant articles and documents

Regioselective enzymatic acylation of methyl shikimate. Influence of acyl chain length and solvent polarity on enzyme specificity.

Candida antarctica lipase A (CAL-A) selectively catalyzes the acylation at the secondary C-4 hydroxyl group of methyl shikimate (2), which possesses three secondary hydroxyl groups, the C-3 allylic one being chemically more reactive. The effect both of the acyl group of the acylating agents and of the solvent polarity has been studied. The selectivity of CAL-A is almost complete with acyl donors that possess short chains. However, when acyl donors have longer chains, better results are obtained by C. antarctica lipase B (CAL-B).

Novel enzymatic synthesis of 4-O-cinnamoyl quinic and shikimic acid derivatives

The first direct synthesis of 4-O-cinnamoyl derivatives of quinic and shikimic acids were accomplished by regioselective esterification with Candida antarctica lipase A. For hydrocinnamic esters, enzymatic transesterification with vinyl esters gave excell

AN IMPROVED SYNTHESIS OF (+/-)-METHYL SHIKIMATE THROUGH STEREOSELECTIVE CIS-DIHYDROXYLATION OF (+/-)-METHYL 5β-HYDROXYCYCLOHEXA-1,3-DIENOATE UNDER PREVOST'S REACTION CONDITIONS

A Prevost-type reaction under "wet" conditions upon the O-t-butyl-dimethylsilyl derivative of (+/-)-methyl 5β-hydroxycyclohexa-1,3-dienoate gives (+/-)-methyl 3α-acetoxy-4β-hydroxy-5β-t-butyldimethylsilyloxycyclohexene which may be readily deprotected to afford (+/-)-methyl shikimate in very high yield.Less selectivity is observed in a similar reaction upon the parent alcohol and when this compound is reacted under dry conditions the major product is (+/-)-methyl 4β,5β-epoxy-3β-acetoxycyclohexenoate.An analysis of Prevost reactions with exo and endo methyl 7-oxabicyclohept-5-en-2-oate is also described.