3-Dehydroshikimic acid

Base Information

• Chemical Name: 3-Dehydroshikimic acid
• CAS No.: 2922-42-1
• Molecular Formula: C7H8 O5
• Molecular Weight: 172.138
• Hs Code.: 2918990090
• European Community (EC) Number: 634-499-7
• Wikipedia: 3-Dehydroshikimic_acid
• Wikidata: Q61014520
• Mol file: 2922-42-1.mol

Synonyms:3-dehydroshikimate;3-dehydroshikimic acid

Chemical Property of 3-Dehydroshikimic acid

Chemical Property:

• Vapor Pressure: 2.99E-08mmHg at 25°C
• Melting Point: 150-152 °C
• Boiling Point: 405.1°Cat760mmHg
• PKA: 3.03±0.60(Predicted)
• Flash Point: 213°C
• PSA: 94.83000
• Density: 1.713g/cm³
• LogP: -1.30800
• Storage Temp.: -20°C Freezer
• Solubility.: Methanol (Slightly), Water (Slightly)
• XLogP3: -0.7
• Hydrogen Bond Donor Count: 2
• Hydrogen Bond Acceptor Count: 5
• Rotatable Bond Count: 0
• Exact Mass: 171.02934832
• Heavy Atom Count: 12
• Complexity: 249

Purity/Quality:

98%,99%, ^*data from raw suppliers

(-)-3-DehydroShikimicAcid ^*data from reagent suppliers

Safty Information:

• Pictogram(s): Xi
• Hazard Codes: Xi
• Statements: 36
• Safety Statements: 26

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: C1C(C(C(=O)C=C1C(=O)[O-])O)O
• Isomeric SMILES: C1[C@H]([C@@H](C(=O)C=C1C(=O)[O-])O)O
• Uses: A metabolite of Shikimic Acid 3-Dehydroshikimic acid is a biochemical intermediate from D-glucose in the synthesis of pro-catechuic acid. 3-Dehydroshikimic acid has been used in a study to describe the synthesis of catechuic acid (1) and ethyl 2,4,5-trihydroxybenzoate (2) from D-glucose-derived β-ketoester. 3-Dehydroshikimic acid has also been used in studies to evaluate the shikimate biosynthetic pathway, in order to develop nontoxic antimicrobial agents, herbicides, and antiparasite drugs.

Technology Process of 3-Dehydroshikimic acid

There total 8 articles about 3-Dehydroshikimic acid which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield: 60.0%

shikimic acid (138-59-0) → (-)-3-dehydroshikimic acid (2922-42-1)

Guidance literature:

With 2,3-dicyano-5,6-dichloro-p-benzoquinone; In tetrahydrofuran; at 65 ℃;

DOI:10.1021/jo00350a101

Reference yield:

D-Glucose (2280-44-6) + phosphoenolpyruvic acid (138-08-9) → shikimic acid (138-59-0) + D-(-)-quinic acid (77-95-2) + (-)-3-dehydroshikimic acid (2922-42-1)

Guidance literature:

With dipotassium hydrogenphosphate; E_. coli SP_1.1; pKD₁₂₁₃₈; citric acid; In water; at 33 ℃; pH=7.0; Further Variations:; Reagents; Enzyme kinetics;

DOI:10.1021/ja0109444

Reference yield:

D-Glucose (2280-44-6) → shikimic acid (138-59-0) + D-(-)-quinic acid (77-95-2) + (-)-3-dehydroshikimic acid (2922-42-1)

Guidance literature:

With E_. coli SP_1.1; pKD₁₂₁₁₂; for 12h; Product distribution; var. time;

DOI:10.1021/ja9830243

upstream raw materials:

D-(-)-quinic acid

3-dehydroquinic acid

shikimic acid

D-Glucose

Downstream raw materials:

3,4-Dihydroxybenzoic acid

3,4,5-trihydroxybenzoic acid

meta-aminobenzoic acid

methyl [3S-(3α,4β,5α)]-3,4,5-trihydroxy-1-cyclohexene-1-carboxylate

Refernces

• 1、 Tonucci, Lucia,Nicastro, Marco,D'Alessandro, Nicola,Bressan, Mario,D'Ambrosio, Primiano,Morvillo, Antonino. "Catalytic aerobic oxidation of allylic alcohols to carbonyl compounds under mild conditions". experimental part. p. 816 - 820. Retrieved 2010/04/23.
• 2、 Ran, Ningqing,Draths,Frost. "Creation of a shikimate pathway variant". . p. 6856 - 6857. Retrieved 2007/10/03.