1,4-dimethyl (2S,3S)-2,3-dihydroxybutanedioate

• ChemBase ID: 147364
• Molecular Formular: C6H10O6
• Molecular Mass: 178.14
• Monoisotopic Mass: 178.04773804
• SMILES: COC(=O)[C@H]([C@@H](C(=O)OC)O)O
• Canonical SMILES: COC(=O)[C@H]([C@@H](C(=O)OC)O)O
• InChI: InChI=1S/C6H10O6/c1-11-5(9)3(7)4(8)6(10)12-2/h3-4,7-8H,1-2H3/t3-,4-/m0/s1
• InChIKey: PVRATXCXJDHJJN-IMJSIDKUSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: 1,4-dimethyl (2S,3S)-2,3-dihydroxybutanedioate
• IUPAC Traditional name: 1,4-dimethyl (2S,3S)-2,3-dihydroxybutanedioate
• Synonyms: D-(-)-Tartaric acid dimethyl ester; Dimethyl D-tartrate; (-)-Dimethyl D-tartrate; 二甲基 D-酒石酸酯; D-(-)-酒石酸二甲酯

Database IDs

• CAS Number: 13171-64-7
• EC Number: 236-118-6
• MDL Number: MFCD00008445
• Beilstein Number: 1726254
• PubChem SID: 162241552; 24854593
• PubChem CID: 21142

CALCULATED PROPERTIES

• Acid pKa: 11.18821
• H Acceptors: 4
• H Donor: 2
• LogD (pH = 5.5): -1.5370127
• LogD (pH = 7.4): -1.5370824
• Log P: -1.5370117
• Molar Refractivity: 35.7516 cm^3
• Polarizability: 14.854973 Å^3
• Polar Surface Area: 93.06 Å^2
• Rotatable Bonds: 5
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Melting Point: ~58 °C; 57-60 °C (dec.)(lit.)
• Boiling Point: 158 °C/0.2 mmHg(lit.)
• Optical Rotation: [α]20/D -21±1°, c = 1% in H2O; [α]20/D -21°, c = 2.5 in H2O

Safety Information

• German water hazard class: 3
• Personal Protective Equipment: Eyeshields, Gloves, type N95 (US), type P1 (EN143) respirator filter

Product Information

• Purity: ≥99.0% (sum of enantiomers, GC); 99%
• Grade: purum
• Optical Purity: ee: ≥99% (GLC)
• Linear Formula: [-CH(OH)CO2CH3]2

DETAILS

Sigma Aldrich - 242942

Packaging
25 g in glass bottle