1,4-dimethyl (2S)-2-hydroxybutanedioate

• ChemBase ID: 70268
• Molecular Formular: C6H10O5
• Molecular Mass: 162.1406
• Monoisotopic Mass: 162.05282342
• SMILES: C(=O)([C@H](CC(=O)OC)O)OC
• Canonical SMILES: COC(=O)C[C@@H](C(=O)OC)O
• InChI: InChI=1S/C6H10O5/c1-10-5(8)3-4(7)6(9)11-2/h4,7H,3H2,1-2H3/t4-/m0/s1
• InChIKey: YSEKNCXYRGKTBJ-BYPYZUCNSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: 1,4-dimethyl (2S)-2-hydroxybutanedioate
• IUPAC Traditional name: 1,4-dimethyl (2S)-2-hydroxybutanedioate
• Synonyms: Dimethyl (S)-2-hydroxysuccinate; Dimethyl L-malate; Dimethyl (S)-(-)-malate; Dimethyl L-malate; Dimethyl L-malate; (S)-2-羟基琥珀酸二甲酯; L-苹果酸二甲酯; (S)-(-)-苹果酸二甲酯; (S)-(-)-苹果酸二甲酯; L-苹果酸二甲酯

Database IDs

• CAS Number: 617-55-0
• EC Number: 432-310-0
• MDL Number: MFCD00066215
• Beilstein Number: 1724363
• PubChem SID: 24863298; 24845250; 162035991
• PubChem CID: 10285815

CALCULATED PROPERTIES

• Acid pKa: 12.443835
• H Acceptors: 3
• H Donor: 1
• LogD (pH = 5.5): -0.82185334
• LogD (pH = 7.4): -0.8218572
• Log P: -0.82185334
• Molar Refractivity: 34.4134 cm^3
• Polarizability: 14.136947 Å^3
• Polar Surface Area: 72.83 Å^2
• Rotatable Bonds: 5
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Boiling Point: 104-108 °C/1 mmHg(lit.)
• Flash Point: >113 °C; >235.4 °F
• Density: 1.223 g/mL at 25 °C(lit.); 1.232 g/mL at 20 °C(lit.)
• Refractive Index: n20/D 1.435(lit.); n20/D 1.441
• Optical Rotation: [α]20/D -6.5°, neat; [α]20/D -6.6±0.5°, neat

Safety Information

• Storage Warning: IRRITANT
• European Hazard Symbols: Irritant (Xi)
• German water hazard class: 3
• Risk Statements: 10-41-43
• Safety Statements: 24-26-37/39-43
• TSCA Listed: false
• GHS Pictograms: GHS02; GHS05; GHS07
• GHS Signal Word: Danger
• GHS Hazard statements: H226-H317-H318
• GHS Precautionary statements: P280-P305 + P351 + P338
• Personal Protective Equipment: Eyeshields, Gloves
• Storage Temperature: 2-8°C

Product Information

• Purity: ≥99.0% (sum of enantiomers, GC); 95+%; 98%
• Grade: puriss.
• Linear Formula: CH3O2CCH2CH(OH)CO2CH3
• Empirical Formula (Hill Notation): C6H10O5

DETAILS

Sigma Aldrich - 374318

Packaging
5, 25 g in glass bottle
Application
This chiral synthon has been used to prepare cytochrome P450 metabolites of arachidonic acid,1 and cyclic sulfolanes with HIV-1 protease inhibition potential.2

Sigma Aldrich - 02315

Other Notes
Starting material used for the synthesis of many chiral building blocks1; Selective reduction of the 1-ester group with BH3.SMe22; Diastereoselective alkylation of C-33,4