3-Dehydroquinic acid

Base Information

• Chemical Name: 3-Dehydroquinic acid
• CAS No.: 10534-44-8
• Molecular Formula: C7H10 O6
• Molecular Weight: 190.153
• Hs Code.: 2918990090
• UNII: Q8HL497GUU
• DSSTox Substance ID: DTXSID50909453
• Nikkaji Number: J93.942K
• Wikipedia: 3-Dehydroquinic_acid
• Wikidata: Q38224
• Metabolomics Workbench ID: 42098
• Mol file: 10534-44-8.mol

Synonyms:3-dehydroquinate;3-dehydroquinic acid

Chemical Property of 3-Dehydroquinic acid

Chemical Property:

• Vapor Pressure: 1.23E-11mmHg at 25°C
• Melting Point: 195-200 °C
• Boiling Point: 489.6°Cat760mmHg
• PKA: 3.45±0.60(Predicted)
• Flash Point: 264°C
• PSA: 115.06000
• Density: 1.818g/cm³
• LogP: -2.11320
• XLogP3: -2.4
• Hydrogen Bond Donor Count: 4
• Hydrogen Bond Acceptor Count: 6
• Rotatable Bond Count: 1
• Exact Mass: 190.04773803
• Heavy Atom Count: 13
• Complexity: 249

Purity/Quality:

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

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: C1C(C(C(=O)CC1(C(=O)O)O)O)O
• Isomeric SMILES: C1[C@H]([C@@H](C(=O)C[C@]1(C(=O)O)O)O)O
• Uses: 3-Dehydroquinic Acid is applied in development of a synthetic 3-dehydroshikimate biosensor in E.coli for metabolite monitoring and genetic screening.

Technology Process of 3-Dehydroquinic acid

There total 12 articles about 3-Dehydroquinic 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%

D-(-)-quinic acid (77-95-2) → 3-dehydroquinic acid (10534-44-8) + (1S,3R,4R)-1,3,4-Trihydroxy-5-oxo-cyclohexanecarboxylic acid

Guidance literature:

With nitric acid; In water;

Reference yield:

D-Glucose (2280-44-6) + succinic acid (110-15-6) → 3,4,5-trihydroxybenzoic acid (149-91-7) + 3-dehydroquinic acid (10534-44-8) + (-)-3-dehydroshikimic acid (2922-42-1) + 3-deoxy-α-D-arabino-2-heptulopyranosonic acid

Guidance literature:

With E_. coli; PEP carboxykinase; pKL_4.79B plasmid; Further Variations:; Reaction partners; Reagents; Product distribution;

DOI:10.1021/ja992477k

Reference yield:

D-(-)-quinic acid (77-95-2) → 3-dehydroquinic acid (10534-44-8)

Guidance literature:

With nitric acid;

upstream raw materials:

D-(-)-quinic acid

3-deoxy-D-arabino-2-heptulosonic acid 7-phosphate

D-Glucose

succinic acid

Downstream raw materials:

methyl (4S,5R)-4,5-dihydroxy-3-oxo-1-cyclohexene-1-carboxylate

methyl 3-dehydroquinate

4,5-di-O-acetyl-3-deshydroquinate de methyle

4,5-bis-O-trimethylsilyl-3-deshydroshikimate de methyle

Refernces

• 1、 Ran, Ningqing,Draths,Frost. "Creation of a shikimate pathway variant". . p. 6856 - 6857. Retrieved 2004.
• 2、 Adachi, Osao,Tanasupawat, Somboon,Yoshihara, Nozomi,Toyama, Hirohide,Matsushita, Kazunobu. "3-dehydroquinate production by oxidative fermentation and further conversion of 3-dehydroquinate to the intermediates in the shikimate pathway.". . p. 2124 - 2131. Retrieved 2003.
• 3、 Tewari, Yadu B.,Goldberg, Robert N.,Hawkins, Alastair R.,Lamb, Heather K.. "A thermodynamic study of the reactions: {2-dehydro-3-deoxy-D-arabino-heptanoate 7-phosphate(aq) = 3-dehydroquinate(aq) + phosphate(aq)} and {3-dehydroquinate(aq) = 3-dehydroshikimate(aq) + H2O(l)}". . p. 1671 - 1691. Retrieved 2002.
• 4、 Adachi, Osao,Ano, Yoshitaka,Toyama, Hirohide,Matsushita, Kazunobu. "High shikimate production from quinate with two enzymatic systems of acetic acid bacteria". . p. 2579 - 2582. Retrieved 2006.