Citramalic acid

Base Information

• Chemical Name: Citramalic acid
• CAS No.: 597-44-4
• Deprecated CAS: 2306-22-1
• Molecular Formula: C5H8O5
• Molecular Weight: 148.116
• European Community (EC) Number: 209-901-5,625-268-1
• NSC Number: 80648
• UNII: FGC721P65H
• DSSTox Substance ID: DTXSID40862265
• Nikkaji Number: J7.390C
• Wikipedia: Citramalic_acid
• Wikidata: Q27098121
• Metabolomics Workbench ID: 165470
• Mol file: 597-44-4.mol

Synonyms:alpha-methylmalate;citramalate;citramalate, (+-)-isomer;citramalate, (R)-isomer;citramalate, (S)-isomer;citramalic acid

Chemical Property of Citramalic acid

Chemical Property:

• Boiling Point: 295.2°Cat760mmHg
• Flash Point: 146.6°C
• Density: 1.513g/cm³
• XLogP3: -0.9
• Hydrogen Bond Donor Count: 3
• Hydrogen Bond Acceptor Count: 5
• Rotatable Bond Count: 3
• Exact Mass: 148.03717335
• Heavy Atom Count: 10
• Complexity: 163

Purity/Quality:

99% ^*data from raw suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CC(CC(=O)O)(C(=O)O)O

Technology Process of Citramalic acid

There total 21 articles about Citramalic 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: 5.0%

4-(β-hydroxyethyl)-4-methyl-1,3-dioxane (2018-45-3) → 2-hydroxy-2-methylbutane-1,4-dioic acid (597-44-4,2306-22-1) + meglutol (503-49-1) + oxalic acid (144-62-7,97993-78-7)

Guidance literature:

With nitric acid; 1. adding, 7 h; 50-60 deg C, 1 h;

DOI:10.1007/BF00474057

Reference yield:

2-Methoxy-4-methylphenol (93-51-6) → citraconic acid (498-23-7,7407-59-2) + 2-methylbutanedioic acid (498-21-5,636-60-2) + 2-hydroxy-2-methylbutane-1,4-dioic acid (597-44-4,2306-22-1) + malonic acid (141-82-2) + 3-methylhexa-2,4 dienedioic acid (31659-59-3,76799-85-4,116672-65-2,17110-47-3) + oxalic acid (144-62-7,97993-78-7)

Guidance literature:

With sodium hydroxide; oxygen; at 45 ℃; for 1.5h; under 63755.1 Torr; Product distribution; Mechanism; var. temp., time, O₂ pressure, conc. and amount of NaOH, different amounts of creosol;

DOI:10.1007/BF00909659

Reference yield:

3-methylhexa-2,4 dienedioic acid (31659-59-3,76799-85-4,116672-65-2,17110-47-3) → citraconic acid (498-23-7,7407-59-2) + 2-methylbutanedioic acid (498-21-5,636-60-2) + 2-hydroxy-2-methylbutane-1,4-dioic acid (597-44-4,2306-22-1) + 2-hydroxy-2-methylpropanedioic acid (595-48-2)

Guidance literature:

With sodium hydroxide; dihydrogen peroxide; at 90 ℃; for 4h; Product distribution; var. conc. of H₂O₂ and NaOH, var. time;

DOI:10.1007/BF00909659

upstream raw materials:

3-methylbutyric acid

potassium cyanide

ethyl acetoacetate

2-chloromethyl-2-hydroxy-succinic acid dimethyl ester

Downstream raw materials:

(S)-citramalic acid

citraconic acid anhydride

(R)-(-)-citramalic acid

L-malic acid

Refernces

• 1、 -. "Method for preparing hydroxy dibasic acid by catalyzing oxidation of acetyl acid raw material". Paragraph 0028-0084. . Retrieved 2021/06/09.
• 2、 Yerabolu, Jayasudhan Reddy,Liotta, Charles L,Krishnamurthy, Ramanarayanan. "Anchimeric-Assisted Spontaneous Hydrolysis of Cyanohydrins Under Ambient Conditions: Implications for Cyanide-Initiated Selective Transformations". supporting information. p. 8756 - 8765. Retrieved 2017/06/30.