(S)-(-)-Methylsuccinic acid

Base Information

• Chemical Name: (S)-(-)-Methylsuccinic acid
• CAS No.: 2174-58-5
• Molecular Formula: C5H8O4
• Molecular Weight: 132.116
• Hs Code.: 2917190090
• European Community (EC) Number: 625-480-4
• DSSTox Substance ID: DTXSID001331129
• Nikkaji Number: J84.153F
• Wikidata: Q27163206
• Mol file: 2174-58-5.mol

Synonyms:2174-58-5;(S)-(-)-Methylsuccinic acid;(S)-2-methylsuccinic acid;(2S)-2-methylbutanedioic acid;(S)-(-)-Pyrotartaric Acid;(S)-methylsuccinic acid;Butanedioic acid, methyl-, (2S)-;(s)-2-methylsuccinicacid;MFCD00192321;methylsuccinate;2-methylbutanedioate;Pyrotartarate;(S)-(-)-MethylsuccinicAcid;Methylbutanedioate;MEZ;(2s)-methylsuccinic acid;(S)-2-methylbutanedioic acid;SCHEMBL791253;CHEBI:91316;(S)-2-Hydroxy-2-methylsuccinate;WXUAQHNMJWJLTG-VKHMYHEASA-N;DTXSID001331129;BCP23566;(S)-(-)-Methylsuccinic acid, 99%;AKOS015840167;DS-12222;CS-0035659;M1227;A815641;J-014264;Q27163206

Chemical Property of (S)-(-)-Methylsuccinic acid

Chemical Property:

• Vapor Pressure: 0.0162mmHg at 25°C
• Melting Point: 110-115 °C(lit.)
• Refractive Index: -15.5 ° (C=2, EtOH)
• Boiling Point: 236.5 °C at 760 mmHg
• PKA: 4.56±0.19(Predicted)
• Flash Point: 111.1 °C
• PSA: 74.60000
• Density: 1.311 g/cm³
• LogP: 0.18180
• Storage Temp.: Keep in dark place,Sealed in dry,Room Temperature
• XLogP3: -0.2
• Hydrogen Bond Donor Count: 2
• Hydrogen Bond Acceptor Count: 4
• Rotatable Bond Count: 3
• Exact Mass: 132.04225873
• Heavy Atom Count: 9
• Complexity: 129

Purity/Quality:

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

(S)-2-MethylsuccinicAcid ^*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
• Isomeric SMILES: C[C@@H](CC(=O)O)C(=O)O

Technology Process of (S)-(-)-Methylsuccinic acid

There total 12 articles about (S)-(-)-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: 81.8%

2-hydroxy-2-methylbutane-1,4-dioic acid (597-44-4,2306-22-1) → L-malic acid (2174-58-5) + (R)-(-)-citramalic acid (6236-10-8,2306-22-1)

Guidance literature:

With formaldehyd; TETRACYCLINE; paraquat dichloride; In water; at 37 ℃; for 69h; Clostridium formicoaceticum, phosphate buffer;

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

Reference yield: 70.0%

phenylmagnesium bromide (1589-82-8) + (S)-methylsuccinic anhydride (6973-20-2) → L-malic acid (2174-58-5) + (S)-2-methyl-4-oxo-5-phenylpentanoic acid

Guidance literature:

With copper(l) iodide; tert-butyl XPhos; In tetrahydrofuran; at -78 ℃; for 6.5h; Reagent/catalyst; Inert atmosphere;

DOI:10.1021/acs.orglett.0c01718

Reference yield: 20.0%

phenylmagnesium bromide (1589-82-8) + (S)-methylsuccinic anhydride (6973-20-2) → L-malic acid (2174-58-5) + (S)-2-methyl-4-oxo-5-phenylpentanoic acid + (S)-3-Methyl-4-oxo-5-phenyl-pentanoic acid

Guidance literature:

With copper(l) iodide; triphenylphosphine; In tetrahydrofuran; at -78 ℃; for 6.5h; Reagent/catalyst; Inert atmosphere;

DOI:10.1021/acs.orglett.0c01718

upstream raw materials:

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

hydrogenchloride

water

methyllycaconitine hydrochloride

Downstream raw materials:

(2S,4R)-4-((tert-butoxycarbonyl)amino)-2-methyl-5-phenylpentanoic acid

(2S,4R)-4-[[2-[(1R,3R)-1-acetoxy-4-methyl-3-[methyl-[(2S,3S)-3-methyl-2-[[(2R)-1-methylpiperidine-2-carbonyl]amino]pentanoyl]amino]pentyl]thiazole-4-carbonyl]amino]-2-methyl-5-phenyl-pentanoic acid

(2S,4R)-4-(2-((1R)-1-acetoxy-3-((2S)-N,3-dimethyl-2-((R)-1-methylpiperidine-2-carboxamido)pentanamido)-4-methylpentyl)thiazole-4-carboxamido)-2-methyl-5-phenylpentanoic acid

Refernces

• 1、 Tang, Hao-Yu,Zhang, Qiang,Gao, Yu-Qi,Zhang, An-Ling,Gao, Jin-Ming. "Miniolins A-C, novel isomeric furanones induced by epigenetic manipulation of Penicillium minioluteum". . p. 2185 - 2190. Retrieved 2015.
• 2、 Zhou, Xuefeng,Fang, Wei,Tan, Suiyi,Lin, Xiuping,Xun, Tianrong,Yang, Bingjie,Liu, Shuwen,Liu, Yonghong. "Aspernigrins with anti-HIV-1 activities from the marine-derived fungus Aspergillus Niger SCSIO Jcsw6F30". . p. 361 - 365. Retrieved 2016.
• 3、 Vishwanatha, Thimmalapura M.,Giepmans, Ben,Goda, Sayed K.,D?mling, Alexander. "Tubulysin Synthesis Featuring Stereoselective Catalysis and Highly Convergent Multicomponent Assembly". supporting information. p. 5396 - 5400. Retrieved 2020/07/08.