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374318 Sigma-Aldrich

Dimethyl (S)-(−)-malate

98%

Synonym: Dimethyl (S)-2-hydroxysuccinate, Dimethyl L-malate

  • CAS Number 617-55-0

  • Linear Formula CH3O2CCH2CH(OH)CO2CH3

  • Molecular Weight 162.14

  •  Beilstein/REAXYS Number 1724363

  •  EC Number 432-310-0

  •  MDL number MFCD00066215

  •  PubChem Substance ID 24863298

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Properties

Related Categories Asymmetric Synthesis, Chemical Synthesis, Chiral Building Blocks, Esters, Organic Building Blocks More...
InChI Key   YSEKNCXYRGKTBJ-BYPYZUCNSA-N
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.)
storage temp.   2-8°C

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.

Packaging

5, 25 g in glass bottle

Safety & Documentation

Safety Information

Symbol 
Signal word 
Danger
Hazard statements 
Personal Protective Equipment 
RIDADR 
UN 1993C 3 / PGIII
WGK Germany 
3
Flash Point(F) 
131 °F
Flash Point(C) 
55 °C

Documents

Certificate of Analysis

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Protocols & Articles
Peer-Reviewed Papers
15

References

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