374318

Dimethyl (S)-(−)-malate

98%

• Synonym(s): Dimethyl (S)-2-hydroxysuccinate, Dimethyl L-malate
• Linear Formula: CH₃O₂CCH₂CH(OH)CO₂CH₃
• CAS Number: 617-55-0
• Molecular Weight: 162.14
• Beilstein/REAXYS Number: 1724363
• EC Number: 432-310-0
• MDL number: MFCD00066215
• UNSPSC Code: 12352108
• PubChem Substance ID: 24863298
• NACRES: NA.22

Properties

• Quality Level: 200
• assay: 98%
• optical activity: [α]20/D −6.5°, neat
• refractive index: n20/D 1.435 (lit.)
• density: 1.223 g/mL at 25 °C (lit.)
• functional group: ester; hydroxyl
• storage temp.: 2-8°C
• SMILES string: COC(=O)C[C@H](O)C(=O)OC
• InChI: 1S/C6H10O5/c1-10-5(8)3-4(7)6(9)11-2/h4,7H,3H2,1-2H3/t4-/m0/s1
• InChI key: YSEKNCXYRGKTBJ-BYPYZUCNSA-N

Description

Application

Dimethyl (S)-(-)-malate may be used as a starting material to synthesize (-)-tulipalin B. The selective reduction of its ester group to alcohol can be accomplished using borane-dimethyl sulfide complex (BMS) in the presence of sodium tetrahydroborate.

This chiral synthon has been used to prepare cytochrome P450 metabolites of arachidonic acid, and cyclic sulfolanes with HIV-1 protease inhibition potential.

Safety Information

• pictograms: GHS02,GHS05,GHS07
• signalword: Danger
• hcodes: H226,H317,H318
• pcodes: P210 - P233 - P240 - P280 - P303 + P361 + P353 - P305 + P351 + P338
• Hazard Classifications: Eye Dam. 1 - Flam. Liq. 3 - Skin Sens. 1
• Storage Class: 3 - Flammable liquids
• wgk_germany: WGK 3
• flash_point_f: 131.0 °F
• flash_point_c: 55 °C
• ppe: Eyeshields, Gloves