3-carboxy-2,3-dideoxy-1-hydroxypropan-1,2,3-tricarboxylic acid

Base Information

• Chemical Name: 3-carboxy-2,3-dideoxy-1-hydroxypropan-1,2,3-tricarboxylic acid
• CAS No.: 320-77-4
• Molecular Formula: C6H8 O7
• Molecular Weight: 192.125
• European Community (EC) Number: 206-282-3
• NSC Number: 203797
• UNII: 9RW6G5D4MQ
• DSSTox Substance ID: DTXSID60861871
• Nikkaji Number: J95.796H
• Wikipedia: Isocitric_acid
• Wikidata: Q288927
• Metabolomics Workbench ID: 142389
• ChEMBL ID: CHEMBL539669
• Mol file: 320-77-4.mol

Synonyms:Isocitricacid (8CI); 1-Hydroxy-1,2,3-propanetricarboxylic acid

Chemical Property of 3-carboxy-2,3-dideoxy-1-hydroxypropan-1,2,3-tricarboxylic acid

Chemical Property:

• Vapor Pressure: 1.3E-05mmHg at 25°C
• Boiling Point: 329.6°C at 760 mmHg
• Flash Point: 167.4°C
• Density: 1.751g/cm³
• XLogP3: -1.8
• Hydrogen Bond Donor Count: 4
• Hydrogen Bond Acceptor Count: 7
• Rotatable Bond Count: 5
• Exact Mass: 192.02700259
• Heavy Atom Count: 13
• Complexity: 233

Purity/Quality:

99%, ^*data from raw suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Chemical Classes: Other Classes -> Organic Acids
• Canonical SMILES: C(C(C(C(=O)O)O)C(=O)O)C(=O)O

Technology Process of 3-carboxy-2,3-dideoxy-1-hydroxypropan-1,2,3-tricarboxylic acid

There total 34 articles about 3-carboxy-2,3-dideoxy-1-hydroxypropan-1,2,3-tricarboxylic 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: 100.0%

α-ketoglutaric acid (328-50-7) + carbon dioxide (124-38-9,18923-20-1) → 1-hydroxy-propane-1,2,3-tricarboxylic acid (320-77-4)

Guidance literature:

With methyl viologen radical cation; isocitrate dehydrogenase; In water; electrochemical reaction: glassy carbon cathode, -0.95 V vs SCE, tris buffer, NaHCO₃;

DOI:10.1021/ja00188a093

Reference yield:

di-isocitric acid lactone + dl-alloisocitric acid lactone + trans-acotinic acid (4023-65-8) → dl-alloisocitric acid + 1-hydroxy-propane-1,2,3-tricarboxylic acid (320-77-4)

Guidance literature:

In water;

Reference yield:

β-D-glucose (492-61-5) + L-valine (72-18-4,25609-85-2,7004-03-7,921-10-8) → 1-hydroxy-propane-1,2,3-tricarboxylic acid (320-77-4) + 2-methylisocitric acid + citric acid (77-92-9,906507-37-7)

Guidance literature:

With Saccharomycopsis lipolytica; In water; at 26 ℃; for 120h; Product distribution; also in n-hexadecane medium; catabolism of amino acids by S_. lipolytica;

upstream raw materials:

cis-aconitic acid

D-Glucose

β-D-glucose

L-valine

Downstream raw materials:

(2RS,3SR)-5-oxotetrahydrofuran-2,3-dicarboxylic acid

oxalosuccinic acid

α-ketoglutaric acid

Refernces

• 1、 Sugimura, Kenji,Kuwabata, Susumu,Yoneyama, Hiroshi. "Electrochemical Fixation of Carbon Dioxide in Oxoglutaric Acid Using an Enzyme as an Electrocatalyst". . p. 2361 - 2362. Retrieved 1989.
• 2、 Mandler, Daniel,Wilner, Itamar. "Photochemical Fixation of Carbon Dioxide: Enzymic Photosynthesis of Malic, Aspartic, Isocitric, and Formic Acids in Artificial Media". . p. 997 - 1004. Retrieved 2007/10/02.