(2R,3R)-2,3-bis(benzoyloxy)butanedioic acid

• ChemBase ID: 107138
• Molecular Formular: C18H14O8
• Molecular Mass: 358.29896
• Monoisotopic Mass: 358.06886741
• SMILES: OC(=O)[C@H](OC(=O)c1ccccc1)[C@@H](OC(=O)c1ccccc1)C(=O)O
• Canonical SMILES: OC(=O)[C@@H]([C@H](C(=O)O)OC(=O)c1ccccc1)OC(=O)c1ccccc1
• InChI: InChI=1S/C18H14O8/c19-15(20)13(25-17(23)11-7-3-1-4-8-11)14(16(21)22)26-18(24)12-9-5-2-6-10-12/h1-10,13-14H,(H,19,20)(H,21,22)/t13-,14-/m1/s1
• InChIKey: YONLFQNRGZXBBF-ZIAGYGMSSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (2R,3R)-2,3-bis(benzoyloxy)butanedioic acid
• IUPAC Traditional name: (2R,3R)-2,3-bis(benzoyloxy)butanedioic acid
• Synonyms: (2R,3R)-2,3-Bis(benzoyloxy)butanedioic Acid; (-)-Di-O-benzoyl-L-tartaric Acid; (-)-O,O'-Dibenzoyl-(2R,3R)-tartaric Acid; (2R,3R)-2,3-Bis(benzoyloxy)succinic Acid; NSC 118224; NSC 338494; Di-O-benzoyl L-Tartaric Acid; (-)-O,O′-Dibenzoyl-L-tartaric acid; Dibenzoyl-L-tartaric acid; DIBENZOIL-L-TARTARIC ACID; L-Tartaric acid 2,3-dibenzoate; (-)-2,3-Dibenzoyl-L-tartaric acid; (-)-O,O′-二苯甲酰-L-酒石酸; 二苯甲酰基-L-酒石酸; 二苯甲酰基-L-酒石酸; L-(-)-二苯甲酰酒石酸

Database IDs

• CAS Number: 2743-38-6
• EC Number: 241-097-1
• MDL Number: MFCD00003074
• Beilstein Number: 709854
• PubChem SID: 24860364; 162092949; 24861354
• PubChem CID: 75969

CALCULATED PROPERTIES

• Acid pKa: 2.7658303
• H Acceptors: 6
• H Donor: 2
• LogD (pH = 5.5): -0.33519888
• LogD (pH = 7.4): -2.942197
• Log P: 3.1618
• Molar Refractivity: 85.8574 cm^3
• Polarizability: 33.62523 Å^3
• Polar Surface Area: 127.2 Å^2
• Rotatable Bonds: 9
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Solubility: Chloroform; Ethanol; Methanol
• Apperance: White Solid
• Melting Point: 140-144°C; 150-153 °C; 152-155 °C(lit.)
• Optical Rotation: [α]20/D -116°, c = 9 in ethanol; [α]20/D -117±2°, c = 5% in ethanol

Safety Information

• Storage Condition: Refrigerator
• European Hazard Symbols: Irritant (Xi)
• German water hazard class: 3
• Risk Statements: 36
• Safety Statements: 26
• GHS Pictograms: GHS07
• GHS Signal Word: Warning
• GHS Hazard statements: H319
• GHS Precautionary statements: P305 + P351 + P338
• Personal Protective Equipment: dust mask type N95 (US), Eyeshields, Gloves

Product Information

• Purity: ≥99.0% (T); 98%
• Grade: puriss.
• Impurities: ≤1% water
• Linear Formula: [C6H5CO2CH(CO2H)-]2
• Empirical Formula (Hill Notation): C18H14O8

DETAILS

MP Biomedicals - 05202708

MP Biomedicals Rare Chemical collection

Sigma Aldrich - 345849

Packaging
25, 100 g in poly bottle

Toronto Research Chemicals - D417326

Reagent used to produce chiral salts.

REFERENCES

• Rabinowitz, J., et al.: Chem. Res. Toxicol., 22, 1594 (2009)