183254-44-6

Basic information

• Product Name: 1-Cyclohexene-1-carboxylicacid,4-hydroxy-3-oxo-,(S)-(9CI)
• Synonyms: 1-Cyclohexene-1-carboxylicacid,4-hydroxy-3-oxo-,(S)-(9CI)
• CAS NO: 183254-44-6
• Molecular Formula: C7H8O4
• Molecular Weight: 0
• Product Categories: CARBOXYLICACID
• Mol File: 183254-44-6.mol

Chemical Properties

• Appearance: /
• CAS DataBase Reference: 1-Cyclohexene-1-carboxylicacid,4-hydroxy-3-oxo-,(S)-(9CI)(CAS DataBase Reference)
• NIST Chemistry Reference: 1-Cyclohexene-1-carboxylicacid,4-hydroxy-3-oxo-,(S)-(9CI)(183254-44-6)
• EPA Substance Registry System: 1-Cyclohexene-1-carboxylicacid,4-hydroxy-3-oxo-,(S)-(9CI)(183254-44-6)

Safety Data

• Hazardous Substances Data: 183254-44-6(Hazardous Substances Data)

Upstream product

• 94903-42-1 (1R,2R,4R,6R,8S)-8-Hydroxy-4-phenyl-3,5,10-trioxa-tricyclo[6.2.1.0^2,6]undecan-9-one 
• 183134-52-3 methyl (1R,3R,4S)-1,3,4-trihydroxycyclohexane-1-carboxylate 
• 183254-43-5 (1R,3R,4S)-1,3,4-Trihydroxy-cyclohexanecarboxylic acid 
• 77-95-2 D-(-)-quinic acid 
• 156413-12-6 4-Hydroxy-3-oxo-cyclohex-1-enecarboxylic acid methyl ester 
• 183134-50-1 (2R,3aR,5R,7R,7aS)-5-Benzyloxycarbonyloxy-7-hydroxy-2-phenyl-hexahydro-benzo[1,3]dioxole-5-carboxylic acid methyl ester 
• 183134-51-2 (2R,3aR,5S,7aS)-5-Benzyloxycarbonyloxy-2-phenyl-3a,4,5,7a-tetrahydro-benzo[1,3]dioxole-5-carboxylic acid methyl ester 
• 183134-49-8 Carbonic acid benzyl ester (1R,2R,4R,6R,8S)-9-oxo-4-phenyl-3,5,10-trioxa-tricyclo[6.2.1.0^2,6]undec-8-yl ester 
• 183134-53-4 (1R,4S)-1,4-Dihydroxy-3-oxo-cyclohexanecarboxylic acid 

Downstream Products

• 122620-79-5 (3R,4R)-3,4-Dihydroxy-cyclohex-1-enecarboxylic acid 
• 122554-88-5 5-deoxy-shikimic acid 

Relevant articles and documents

Comparison of the substrate specificity of type I and type II dehydroquinases with 5-deoxy- and 4,5-dideoxy-dehydroquinic acid

Syntheses of 5-deoxydehydroquinic acid and 4,5-dideoxydehydroquinic acid from quinic acid are described. These substrate analogues were tested against the mechanistically-distinct type I and type II dehydroquinases. The C-4 hydroxy group of the substrate is shown to be important for imine formation on the type I enzyme but appears not to contribute significantly to specificity on the type II dehydroquinase.

SPECIFITY OF E. COLI SHIKIMATE DEHYDROGENASE TOWARDS ANALOGUES OF 3-DEHYDROSHIKIMIC ACID

Analogues of 3-dehydroshikimic acid which lack the C-4 and C-5 hydroxyl groups have been synthesised and assayed as substrates for shikimate dehydrogenase.The presence of the C-4 hydroxyl group is found to be very important for specificity, whereas the C-5 hydroxyl group is not.The enzyme exhibits enantioselectivity at C-1 and C-4 of the racemic substrate analogues.