(S)-2-Hydroxy-2-methylsuccinic acid

Base Information

• Chemical Name: (S)-2-Hydroxy-2-methylsuccinic acid
• CAS No.: 6236-09-5
• Molecular Formula: C5H8O5
• Molecular Weight: 148.116
• European Community (EC) Number: 228-350-1
• UNII: B3FC6PA80I
• DSSTox Substance ID: DTXSID901017263
• Nikkaji Number: J73.969C
• Wikidata: Q27104026
• Metabolomics Workbench ID: 51926
• Mol file: 6236-09-5.mol

Synonyms:(S)-2-Hydroxy-2-methylsuccinic acid;6236-09-5;L-citramalic acid;(S)-(+)-Citramalic acid;(S)-Citramalic acid;(2S)-2-hydroxy-2-methylbutanedioic acid;S-citramalic acid;(+)-citramalic acid;(S)-2-methylmalic acid;Citramalic acid, (+)-;B3FC6PA80I;L-alpha-hydroxypyrotartaric acid;(2S)-2-hydroxy-2-methylsuccinic acid;(S)-citramalate;(2S)-2-hydroxy-2-methylbutanedioate;(3S)-citramalic acid;S-alpha-hydroxypyrotartaric acid;(3S)-alpha-hydroxypyrotartaric acid;UNII-B3FC6PA80I;(+)-METHYLMALIC ACID;SCHEMBL1357615;CHEBI:29003;DTXSID901017263;(S)-alpha-Hydroxypyrotartaric acid;2-Hydroxy-2-methylsuccinic acid #;(S)-2-Hydroxy-2-methylsuccinicacid;CITRAMALIC ACID D-FORM [MI];EINECS 228-350-1;SB37977;CS-0435033;Butanedioic acid, 2-hydroxy-2-methyl-, (S)-;C02614;Butanedioic acid, 2-hydroxy-2-methyl-, (2S)-;Q27104026;EF5DE549-7AF1-4D1B-A53A-1E4256301878

Chemical Property of (S)-2-Hydroxy-2-methylsuccinic acid

Chemical Property:

• Appearance/Colour: white fine crystalline powder
• Vapor Pressure: 0.000161mmHg at 25°C
• Melting Point: 109-111 °C(lit. )
• Refractive Index: 1.521
• Boiling Point: 295.2 °C at 760 mmHg
• PKA: 3.65±0.28(Predicted)
• Flash Point: 146.6 °C
• PSA: 94.83000
• Density: 1.513 g/cm³
• LogP: -0.70330
• 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

(S)-(+)-Citramalicacid 95% ^*data from reagent suppliers

Safty Information:

• Pictogram(s): Xi
• Hazard Codes: Xi
• Statements: 36/37/38
• Safety Statements: 26-36

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CC(CC(=O)O)(C(=O)O)O
• Isomeric SMILES: C[C@](CC(=O)O)(C(=O)O)O
• Uses: (+)-Citramalic Acid, is an analog of Malic Acid (M159510) that is produced from the condensation reaction of pyruvate and acetyl CoA catalyzed by (R)-citramalate synthase.

Technology Process of (S)-2-Hydroxy-2-methylsuccinic acid

There total 21 articles about (S)-2-Hydroxy-2-methylsuccinic 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: 96.0%

(R)-4-methyl-4-(trichloromethyl)-2-oxetanone (93239-42-0) → (S)-citramalic acid (6236-09-5,2306-22-1)

Guidance literature:

With sodium hydroxide; In water; 1.) 5 deg C; 2.) room temperature;

Reference yield: 80.0%

(2'R,4'S)-2-<2'-(tert-Butyl)-4'-methyl-1',3'-dioxolan-4'-yl>essigsaeure → (S)-citramalic acid (6236-09-5,2306-22-1)

Guidance literature:

With hydrogenchloride; at 80 ℃; for 19h;

DOI:10.1002/hlca.19850680611

Reference yield: 69.8%

Mesaconic acid (498-24-8,7407-59-2) → (S)-citramalic acid (6236-09-5,2306-22-1)

Guidance literature:

With formaldehyd; TETRACYCLINE; paraquat dichloride; In water; at 37 ℃; for 24h; Clostridium formicoaceticum, phosphate buffer;

DOI:10.1016/S0040-4020(01)85678-7

upstream raw materials:

Mesaconic acid

2-hydroxy-2-methylbutane-1,4-dioic acid

S-(+)-Methyl-γ-iodo-β-carbomethoxy-β-hydroxy-butyrat

<(2S,4S)-2-tert-butyl-4-methyl-5-oxo-1,3-dioxolan-4-yl>acetic acid

Downstream raw materials:

N-(2,3,4,6-tetra-O-benzyl-β-D-glucopyranosyl)-2-[(5S)-5-methyl-4-oxo-2,2-bis(trifluoromethyl)-1,3-dioxolan-5-yl]acetamide

(+)-(S)-2-(2,2,4-trimethyl-1,3-dioxolan-4-ethyl) tosylate

3-phenylpropionic acid (2S)-2-(methyloxiranyl)ethyl ester

(1S,5R)-5-methyl-1-phenethyl-2,7,8-trioxabicyclo[3.2.1]octane

Refernces

• 1、 Gill, Melvyn,Harte, Michael F.,Ten, Abilio. "Pigments of Fungi. LIX - Synthesis of (1S,3S)- and (1R,3R)-austrocortilutein and (1S,3S)-austrocortirubin from citramalic acid". . p. 245 - 256. Retrieved 2007/10/03.
• 2、 Eck, Richard,Simon, Helmut. "Preparation of Both Enantiomers of Malic and Citramalic Acid and Other Hydroxysuccinic Acid Derivatives by Stereospecific Hydrations of cis or trans 2-Butene-1,4-dioic Acids with Resting Cells of Clostridium formicoaceticum". . p. 13641 - 13654. Retrieved 2007/10/02.