2922-42-1 Usage
Description
(-)-3-Dehydroshikimic acid, also known as 3-dehydroshikimic acid, is a 4-oxo monocarboxylic acid derived from shikimic acid. It is an off-white powder and serves as a biochemical intermediate in the synthesis of various organic compounds. The acid is formed when the allylic hydroxy group of shikimic acid is oxidized to the corresponding keto group.
Uses
Used in Pharmaceutical Industry:
(-)-3-Dehydroshikimic acid is used as a biochemical intermediate for the synthesis of pro-catechuic acid, which is a key compound in the production of various pharmaceuticals. It plays a crucial role in the development of nontoxic antimicrobial agents, herbicides, and antiparasite drugs.
Used in Chemical Synthesis:
(-)-3-Dehydroshikimic acid is used as a starting material for the synthesis of catechuic acid (1) and ethyl 2,4,5-trihydroxybenzoate (2) from D-glucose-derived β-ketoester. This application is significant in the field of organic chemistry, as it allows for the creation of various compounds with potential applications in different industries.
Used in Research and Development:
(-)-3-Dehydroshikimic acid is used as a research tool to evaluate the shikimate biosynthetic pathway. Understanding this pathway is essential for developing new drugs and compounds with potential applications in various fields, including medicine, agriculture, and environmental science.
Biochem/physiol Actions
Metabolite of the shikimate pathway with a chromophore suitable for continuous spectrophotometric assay. Precursor of aromatic metabolites in microorganisms.
Check Digit Verification of cas no
The CAS Registry Mumber 2922-42-1 includes 7 digits separated into 3 groups by hyphens. The first part of the number,starting from the left, has 4 digits, 2,9,2 and 2 respectively; the second part has 2 digits, 4 and 2 respectively.
Calculate Digit Verification of CAS Registry Number 2922-42:
(6*2)+(5*9)+(4*2)+(3*2)+(2*4)+(1*2)=81
81 % 10 = 1
So 2922-42-1 is a valid CAS Registry Number.
InChI:InChI=1/C7H8O5/c8-4-1-3(7(11)12)2-5(9)6(4)10/h1,5-6,9-10H,2H2,(H,11,12)
2922-42-1Relevant articles and documents
Mechanistic studies on type I and type II dehydroquinase with (6R)- and (6S)-6-fluoro-3-dehydroquinic acids
Parker, Emily J.,Bello, Concepcion Gonzalez,Coggins, John R.,Hawkins, Alastair R.,Abell, Chris
, p. 231 - 234 (2000)
(6R)- and (6S)-6-Fluoro-3-dehydroquinic acids are shown to be substrates for type I and type II dehydroquinases. Their differential reactivity provides insight into details of the reaction mechanism and enables a novel enzyme-substrate imine to be trapped
High shikimate production from quinate with two enzymatic systems of acetic acid bacteria
Adachi, Osao,Ano, Yoshitaka,Toyama, Hirohide,Matsushita, Kazunobu
, p. 2579 - 2582 (2008/02/12)
3-Dehydroshikimate was formed with a yield of 57-77% from quinate via 3-dehydroquinate by two successive enzyme reactions, quinoprotein quinate dehydrogenase (QDH) and 3-dehydroquinate dehydratase, in the cytoplasmic membranes of acetic acid bacteria. 3-Dehydroshikimate was then reduced to shikimate (SKA) with NADP-dependent SKA dehydrogenase (SKDH) from the same organism. When SKDH was coupled with NADP-dependent D-glucose dehydrogenase (GDH) in the presence of excess D-glucose as an NADPH regenerating system, SKDH continued to produce SKA until 3-dehydroshikimate added initially in the reaction mixture was completely converted to SKA. Based on the data presented, a strategy for high SKA production was proposed.
Purification and characterization of membrane-bound quinoprotein quinate dehydrogenase
Adachi, Osao,Yoshihara, Nozomi,Tanasupawat, Somboon,Toyama, Hirohide,Matsushita, Kazunobu
, p. 2115 - 2123 (2007/10/03)
Several bacterial strains carrying quinoprotein quinate dehydrogenase (QDH) were screened through acetic acid bacteria and other bacteria. Strong enzyme activity was found in the membrane fraction of Gluconobacter melanogenus IFO 3294, G. oxydans IFO 3292
