Merck
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374318

Sigma-Aldrich

Dimethyl (S)-(−)-malate

98%

Synonym(s):
Dimethyl L-malate, Dimethyl (S)-2-hydroxysuccinate
Linear Formula:
CH3O2CCH2CH(OH)CO2CH3
CAS Number:
Molecular Weight:
162.14
Beilstein:
1724363
EC Number:
MDL number:
PubChem Substance ID:
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

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

Packaging

5, 25 g in glass bottle

Signal Word

Danger

Hazard Statements

Hazard Classifications

Eye Dam. 1 - Flam. Liq. 3 - Skin Sens. 1

Storage Class Code

3 - Flammable liquids

WGK

WGK 3

Flash Point(F)

131.0 °F

Flash Point(C)

55 °C

Personal Protective Equipment

dust mask type N95 (US), Eyeshields, Gloves

Certificate of Analysis

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Certificate of Origin

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Falck, J.R. et al.
Tetrahedron Letters, 33, 4893-4893 (1992)
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.
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)
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)
Jason Boehme et al.
American journal of physiology. Heart and circulatory physiology, 311(4), H944-H957 (2016-09-04)
Vascular cell hyperproliferation and metabolic reprogramming contribute to the pathophysiology of pulmonary arterial hypertension (PAH). An important cause of PAH in children with congenital heart disease (CHD) is increased pulmonary blood flow (PBF). To better characterize this disease course we

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