| Identification | More | [Name]
Dimethyl malate | [CAS]
617-55-0 | [Synonyms]
DIMETHYL L-(-)-MALATE
DIMETHYL L-MALATE
DIMETHYL (S)-2-HYDROXYSUCCINATE
DIMETHYL (S)-(-)-MALATE
L-(-)-APPLE ACID DIMETHYL ESTER
L-DIMETHYLMALATE
L-(-)-MALIC ACID DIMETHYL ESTER
L-MALIC ACID DIMETHYL ESTER
(S)-DIMETHYL HYDROXYBUTANEDIOATE
(S)-DIMETHYL HYDROXYSUCCINATE
(S)-(-)-DIMETHYL MALATE
Dimethyl L-malate (LDMM)
2-Hydroxybutanedioic acid dimethyl ester
Dimethyl malate
Dimethyl (S)-2-hydroxysuccinate, Dimethyl L-malate
(2S)-2-Hydroxybutanedioic acid dimethyl ester
(2S)-2-Hydroxysuccinic acid dimethyl ester
(S)-2-Hydroxybutanedioic acid dimethyl ester
(S)-Hydroxysuccinic acid dimethyl ester | [EINECS(EC#)]
432-310-0 | [Molecular Formula]
C6H10O5 | [MDL Number]
MFCD00066215 | [Molecular Weight]
162.14 | [MOL File]
617-55-0.mol |
| Chemical Properties | Back Directory | [Appearance]
Colourless Oil | [Boiling point ]
104-108 °C1 mm Hg(lit.) | [density ]
1.232 g/mL at 20 °C(lit.)
| [refractive index ]
n20/D 1.441
| [Fp ]
>230 °F
| [storage temp. ]
2-8°C
| [solubility ]
Chloroform (Sparingly), Methanol (Slightly) | [form ]
Liquid | [pka]
11.72±0.20(Predicted) | [color ]
Colorless to pale yellow | [Optical Rotation]
[α]20/D 6.5°, neat | [BRN ]
1724363 | [InChIKey]
YSEKNCXYRGKTBJ-BYPYZUCNSA-N | [LogP]
-0.830 (est) | [CAS DataBase Reference]
617-55-0(CAS DataBase Reference) | [EPA Substance Registry System]
617-55-0(EPA Substance) |
| Safety Data | Back Directory | [Hazard Codes ]
Xi | [Risk Statements ]
R36/37/38:Irritating to eyes, respiratory system and skin . | [Safety Statements ]
S26:In case of contact with eyes, rinse immediately with plenty of water and seek medical advice .
S36:Wear suitable protective clothing . | [RIDADR ]
1993 | [WGK Germany ]
3
| [F ]
10-21 | [HazardClass ]
3 | [PackingGroup ]
Ⅲ | [HS Code ]
29181990 |
| Hazard Information | Back Directory | [Chemical Properties]
Colourless Oil | [Uses]
This chiral synthon has been used to prepare cytochrome P450 metabolites of arachidonic acid, and cyclic sulfolanes with HIV-1 protease inhibition potential. | [Synthesis]
Thionyl chloride (117 g, 0.98 mol) was slowly added dropwise to a methanol (400 mL) solution of L-malic acid (59.9 g, 0.45 mol) in an ice-water bath. After the dropwise addition, the reaction mixture was stirred at room temperature (25 °C) for overnight reaction. The progress of the reaction was monitored by thin layer chromatography (TLC, unfolding agent ratio ethyl acetate: methanol = 10:1). After completion of the reaction, the solvent was evaporated under reduced pressure. Saturated sodium bicarbonate solution (200 mL) was added to the residue and the aqueous phase was extracted with ethyl acetate (3 x 150 mL). The organic phases were combined, washed sequentially with water (3×80 mL), saturated saline (3×80 mL) and dried over anhydrous sodium sulfate. The solvent was removed by concentration under reduced pressure to give dimethyl L-malate as a light yellow oil in 98% yield (71.5 g, 0.44 mol). | [References]
[1] Bioorganic and medicinal chemistry, 2002, vol. 10, # 6, p. 1829 - 1839
[2] Organic Letters, 2009, vol. 11, # 5, p. 1135 - 1137
[3] RSC Advances, 2016, vol. 6, # 27, p. 22737 - 22748
[4] Tetrahedron, 1992, vol. 48, # 30, p. 6325 - 6334
[5] Tetrahedron Letters, 2003, vol. 44, # 16, p. 3391 - 3395 |
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