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374318

Sigma-Aldrich

Dimethyl (S)-(−)-malate

98%

Synonym(s):

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

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About This Item

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

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

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

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.

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Danger

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

Certificates of Analysis (COA)

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Falck, J.R. et al.
Tetrahedron Letters, 33, 4893-4893 (1992)
Use of enzymic hydrolysis of dimethyl malates for a short synthesis of tulipalin B and of its enantiomer.
Papageorgiou C and Benezra C.
The Journal of Organic Chemistry, 50(7), 1144-1145 (1985)
Cyclic sulfolanes as novel and high affinity P2 ligands for HIV-1 protease inhibitors.
A K Ghosh et al.
Journal of medicinal chemistry, 36(7), 924-927 (1993-04-02)
Rajesh Gupta et al.
The Journal of biological chemistry, 293(47), 18086-18098 (2018-09-20)
Secreted proteins are important metabolic regulators in both healthy and disease states. Here, we sought to investigate the mechanism by which the secreted protein complement 1q-like-3 (C1ql3) regulates insulin secretion from pancreatic β-cells, a key process affecting whole-body glucose metabolism.
Combination of borane-dimethyl sulfide complex with catalytic sodium tetrahydroborate as a selective reducing agent for a-hydroxy esters. Versatile chiral building block from (s)-(-)-malic acid.
Saito S, et al.
Chemistry Letters (Jpn), 13(8), 1389-1392 (1984)
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