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Merck
모든 사진(1)

주요 문서

374318

Sigma-Aldrich

Dimethyl (S)-(−)-malate

98%

동의어(들):

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

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About This Item

Linear Formula:
CH3O2CCH2CH(OH)CO2CH3
CAS Number:
Molecular Weight:
162.14
Beilstein:
1724363
EC Number:
MDL number:
UNSPSC 코드:
12352108
PubChem Substance ID:
NACRES:
NA.22

Quality Level

분석

98%

광학 활성

[α]20/D −6.5°, neat

refractive index

n20/D 1.435 (lit.)

density

1.223 g/mL at 25 °C (lit.)

작용기

ester
hydroxyl

저장 온도

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

애플리케이션

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.

픽토그램

FlameCorrosionExclamation mark

신호어

Danger

유해 및 위험 성명서

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

개인 보호 장비

Eyeshields, Gloves


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문서 라이브러리 방문

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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