2922-42-1

Basic information

• Product Name: (-)-3-DEHYDROSHIKIMIC ACID
• Synonyms: DHS;5-DEHYDROSHIKIMIC ACID;(-)-3-DEHYDROSHIKIMIC ACID;4,5-DIHYDROXY-3-OXO TRANS;(4(S)-TRANS)-4,5-DIHYDROXY-3-OXO-1-CYCLOHEXENE-1-CARBOXYLIC ACID;DHS, 5-Dehydroshikimic Acid, 1-Cyclohexene-1-carboxylic Acid, 4,5-Dihydroxy-3-oxo trans;(4S)-4β,5α-Dihydroxy-3-oxo-1-cyclohexene-1-carboxylic acid;(4S,5R)-3-Oxo-4,5-dihydroxycyclohexa-1-ene-1-carboxylic acid
• CAS NO: 2922-42-1
• Molecular Formula: C₇H₈O₅
• Molecular Weight: 172.14
• Product Categories: Various Metabolites and Impurities;Metabolites
• Mol File: 2922-42-1.mol

Chemical Properties

• Melting Point: 150-152 °C
• Boiling Point: 405.1°Cat760mmHg
• Flash Point: 213°C
• Appearance: /
• Density: 1.713g/cm³
• Vapor Pressure: 2.99E-08mmHg at 25°C
• Refractive Index: 1.651
• Storage Temp.: -20°C Freezer
• Solubility: Methanol (Slightly), Water (Slightly)
• PKA: 3.03±0.60(Predicted)
• Stability: Temperature Sensitive
• CAS DataBase Reference: (-)-3-DEHYDROSHIKIMIC ACID(CAS DataBase Reference)
• NIST Chemistry Reference: (-)-3-DEHYDROSHIKIMIC ACID(2922-42-1)
• EPA Substance Registry System: (-)-3-DEHYDROSHIKIMIC ACID(2922-42-1)

Safety Data

• Hazard Codes: Xi
• Statements: 36
• Safety Statements: 26
• WGK Germany: 3
• Hazardous Substances Data: 2922-42-1(Hazardous Substances Data)

Usage

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.

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)

Upstream product

• 2280-44-6 D-Glucose 
• 138-08-9 phosphoenolpyruvic acid 
• 110-15-6 succinic acid 
• 138-59-0 shikimic acid 
• 10534-44-8 3-dehydroquinic acid 
• 77-95-2 D-(-)-quinic acid 

Downstream Products

• 84806-48-4 methyl (4S,5R)-4,5-dihydroxy-3-oxo-1-cyclohexene-1-carboxylate 
• 689-31-6 3-oxoadipic acid 
• 138-59-0 shikimic acid 
• 30257-06-8 (2S)-<2-2H>dehydroquinate 
• 30257-06-8 (2R)-<2-2H>dehydroquinate 
• 99-50-3 3,4-Dihydroxybenzoic acid 
• 120-80-9 benzene-1,2-diol 
• 99-14-9 tricarallylic acid 
• 149-91-7 3,4,5-trihydroxybenzoic acid 
• 184105-29-1 dihydrogallic acid 
• 87-66-1 2-hydroxyresorcinol 
• 148694-46-6 (4S,5R)-4,5-Bis-(tert-butyl-dimethyl-silanyloxy)-3-oxo-cyclohex-1-enecarboxylic acid methyl ester 
• 148694-48-8 (4R,5R)-4,5-Dihydroxy-3-methylene-cyclohex-1-enecarboxylic acid methyl ester 
• 148694-50-2 methyl 3-homoshikimate 

Relevant articles and documents

Mechanistic studies on type I and type II dehydroquinase with (6R)- and (6S)-6-fluoro-3-dehydroquinic acids

(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

Catalytic aerobic oxidation of allylic alcohols to carbonyl compounds under mild conditions

A new catalytic aerobic oxidation of alcohols to aldehydes under green conditions was developed (room temperature and pressure, water solution, open vials). The water-soluble platinum(II) tetrasulfophthalocyanine (PtPcS) catalyst showed the best selectivity for carbonyl derivatives, and in particular for α,β-unsaturated alcohols; the reactions are slow.

High shikimate production from quinate with two enzymatic systems of acetic acid bacteria

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.

Creation of a shikimate pathway variant

The competition between the Escherichia coli carbohydrate phosphotransferase system and 3-deoxy-d-arabino-heptulosonate 7-phosphate (DAHP) synthase for phosphoenolpyruvate limits the concentration and yield of natural products microbially synthesized via the shikimate pathway. To circumvent this competition for phosphoenolpyruvate, a shikimate pathway variant has been created. 2-Keto-3-deoxy-6-phosphogalactonate (KDPGal) aldolases encoded by Escherichia coli dgoA and Klebsiella pneumoniae dgoA are subjected to directed evolution. The evolved KDPGal aldolase isozymes exhibit 4-8-fold higher specific activities relative to that for native KDPGal aldolase with respect to catalyzing the condensation of pyruvate and d-erythrose 4-phosphate to produce DAHP. To probe the ability of the created shikimate pathway variant to support microbial growth and metabolism, growth rates and synthesis of 3-dehydroshikimate are examined for E. coli constructs that lack phosphoenolpruvate-based DAHP synthase activity and rely on evolved KDPGal aldolase for biosynthesis of shikimate pathway intermediates and products. Copyright

3-dehydroquinate production by oxidative fermentation and further conversion of 3-dehydroquinate to the intermediates in the shikimate pathway.

3-Dehydroquinate production from quinate by oxidative fermentation with Gluconobacter strains of acetic acid bacteria was analyzed for the first time. In the bacterial membrane, quinate dehydrogenase, a typical quinoprotein containing pyrroloquinoline qui

Purification and characterization of membrane-bound quinoprotein quinate dehydrogenase

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

Hydroaromatic equilibration during biosynthesis of shikimic acid

The expense and limited availability of shikimic acid isolated from plants has impeded utilization of this hydroaromatic as a synthetic starting material. Although recombinant Escherichia coli catalysts have been constructed that synthesize shikimic acid from glucose, the yield, titer, and purity of shikimic acid are reduced by the sizable concentrations of quinic acid and 3-dehydroshikimic acid that are formed as byproducts. The 28.0 g/L of shikimic acid synthesized in 14% yield by E. coli SP1.1/pKD12.138 in 48 h as a 1.6:1.0:0.65 (mol/mol/mol) shikimate/quinate/dehydroshikimate mixture is typical of synthesized product mixtures. Quinic acid formation results from the reduction of 3-dehydroquinic acid catalyzed by aroE-encoded shikimate dehydrogenase. Is quinic acid derived from reduction of 3-dehydroquinic acid prior to synthesis of shikimic acid? Alternatively, does quinic acid result from a microbe-catalyzed equilibration involving transport of initially synthesized shikimic acid back into the cytoplasm and operation of the common pathway of aromatic amino acid biosynthesis in the reverse of its normal biosynthetic direction? E. coli SP1.1/pSC5.214A, a construct incapable of de novo synthesis of shikimic acid, catalyzed the conversion of shikimic acid added to its culture medium into a 1.1:1.0:0.70 molar ratio of shikimate/quinate/dehydroshikimate within 36 h. Further mechanistic insights were afforded by elaborating the relationship between transport of shikimic acid and formation of quinic acid. These experiments indicate that formation of quinic acid during biosynthesis of shikimic acid results from a microbe-catalyzed equilibration of initially synthesized shikimic acid. By apparently repressing shikimate transport, the aforementioned E. coli SP1.1/pKD12.138 synthesized 52 g/L of shikimic acid in 18% yield from glucose as a 14:1.0:3.0 shikimate/quinate/dehydroshikimate mixture.

Benzene-free synthesis of phenol

Heating shikimic acid in near-critical water leads to the formation of phenol. Since shikimic acid can now be obtained by the microbial conversion of glucose, a benzene-freer route to phenol could become an alternative to the industrial Hock oxidation of cumene derived from benzene (see scheme).