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重要文件

374318

Sigma-Aldrich

(S)-(-)-苹果酸二甲酯

98%

同義詞:

(S)-2-羟基琥珀酸二甲酯, L-苹果酸二甲酯

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About This Item

線性公式:
CH3O2CCH2CH(OH)CO2CH3
CAS號碼:
分子量::
162.14
Beilstein:
1724363
EC號碼:
MDL號碼:
分類程式碼代碼:
12352108
PubChem物質ID:
NACRES:
NA.22
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品質等級

化驗

98%

光學活性

[α]20/D −6.5°, neat

折射率

n20/D 1.435 (lit.)

密度

1.223 g/mL at 25 °C (lit.)

官能基

ester
hydroxyl

儲存溫度

2-8°C

SMILES 字串

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 密鑰

YSEKNCXYRGKTBJ-BYPYZUCNSA-N

應用

(S)-(-)-苹果酸二甲酯可作为起始试剂用于合成 (-)-郁金香内酯B。[1]其酯基向醇的选择性还原可通过在四氢硼酸钠的存在下使用硼烷二甲基硫醚络合物(BMS)完成。[2]
该手性合成子已被用于制备花生四烯酸的细胞色素P450代谢产物,[3]以及具有HIV-1蛋白酶抑制潜能的环状的环丁砜。[4]

訊號詞

Danger

危險聲明

危險分類

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

儲存類別代碼

3 - Flammable liquids

水污染物質分類(WGK)

WGK 3

閃點(°F)

131.0 °F

閃點(°C)

55 °C

個人防護裝備

Eyeshields, Gloves


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分析證明 (COA)

Lot/Batch Number

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Falck, J.R. et al.
Tetrahedron Letters, 33, 4893-4893 (1992)
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)
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)

Questions

  1. What is the recommended procedure for diluting Dimethyl (S)-(-)-malate with the catalog number 374318 (CAS 617-55-0)? If it is possible to dilute it in water, how should the required amount be calculated?

    1 answer
    1. The solubility of product number 374318 has not been validated; however, it is expected to be soluble in chloroform, ethanol, methanol, and ethyl acetate. It is unlikely to be soluble in water, though there may be slight solubility at very low concentrations.

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