184105-29-1

Basic information

• Product Name: 3-Cyclohexene-1-carboxylic acid, 3,4-dihydroxy-5-oxo-
• CAS NO: 184105-29-1
• Molecular Formula: C7H8O5
• Molecular Weight: 172.138
• Mol File: 184105-29-1.mol
• Article Data: 1

Chemical Properties

• CAS DataBase Reference: 3-Cyclohexene-1-carboxylic acid, 3,4-dihydroxy-5-oxo-(CAS DataBase Reference)
• NIST Chemistry Reference: 3-Cyclohexene-1-carboxylic acid, 3,4-dihydroxy-5-oxo-(184105-29-1)
• EPA Substance Registry System: 3-Cyclohexene-1-carboxylic acid, 3,4-dihydroxy-5-oxo-(184105-29-1)

Safety Data

• Hazardous Substances Data: 184105-29-1(Hazardous Substances Data)

Upstream product

• 149-91-7 3,4,5-trihydroxybenzoic acid 
• 2922-42-1 (-)-3-dehydroshikimic acid 

Relevant articles and documents

Reaction of 3-dehydroshikimic acid with molecular oxygen and hydrogen peroxide: Products, mechanism, and associated antioxidant activity

In the presence of molecular oxygen or hydrogen peroxide, inorganic phosphate catalyzes the conversion of 3-dehydroshikimic acid (DHS) into gallic acid. Other products formed in the reaction of DHS with oxygen include protocatechuic acid, tricarballylic acid, and pyrogallol. With hydrogen peroxide as oxidant, pyrogallol formation is not observed, and smaller amounts of tricarballylic acid are produced. Evidence favoring a mechanism involving phosphate-catalyzed tautomerization of DHS to a reactive enediol intermediate follows from the successful isolation of dihydrogallic acid when oxidant is excluded from phosphate-buffered solutions of DHS. The reductone-like solution chemistry of DHS and the radical quenching reactivity of the phenolics formed from DHS prompted an appraisal of DHS antioxidant activity. Based on two different analyses, DHS was discovered to possess significant antioxidant activity relative to α-tocopherol, gallic acid, propyl gallate, and tert-butylhydroquinone.