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

• ChemBase ID: 74450
• Molecular Formular: C6H10O6
• Molecular Mass: 178.14
• Monoisotopic Mass: 178.04773804
• SMILES: O(C(=O)[C@@H]([C@@H](C(=O)OC)O)O)C
• 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+
• InChIKey: PVRATXCXJDHJJN-ZXZARUISSA-N

NAMES AND DATABASE IDS

Names

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

Database IDs

• CAS Number: 608-68-4
• EC Number: 210-166-8
• MDL Number: MFCD00064437
• Beilstein Number: 1726256
• PubChem SID: 162039369
• PubChem CID: 6992168

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: 56-61°C; 57-60°C
• Boiling Point: 158°C/11mm; 163°C/23mm
• Flash Point: >113°C; >170°C(338°F)
• Density: 1.238; 1.30
• Optical Rotation: +21 (c=1 in water)

Safety Information

• Storage Warning: Irritant
• TSCA Listed: 是

Product Information

• Purity: 99%

REFERENCES

• Has been used in Sharpless epoxidation of allylic alcohols; see tert-Butyl hydroperoxide, A13926.
• Cyclic ketals formed with dimethyl tartrate as the diol component undergo highly selective bromination: Angew. Chem. Int. Ed., 25, 259 (1986).