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

• ChemBase ID: 69820
• Molecular Formular: C18H14O8
• Molecular Mass: 358.29896
• Monoisotopic Mass: 358.06886741
• SMILES: C(=O)([C@@H](OC(=O)c1ccccc1)[C@H](OC(=O)c1ccccc1)C(=O)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-/m0/s1
• InChIKey: YONLFQNRGZXBBF-KBPBESRZSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (2S,3S)-2,3-bis(benzoyloxy)butanedioic acid
• IUPAC Traditional name: (2S,3S)-2,3-bis(benzoyloxy)butanedioic acid
• Synonyms: DIBENZOYL-D-TARTARIC ACID; (+)-O,O′-Dibenzoyl-D-tartaric acid; D-Tartaric acid 2,3-dibenzoate; (+)-2,3-Dibenzoyl-D-tartaric acid; (2S,3S)-2,3-Bis(benzoyloxy)butanedioic Acid; (+)-Di-O-benzoyl-D-tartaric Acid; (+)-O,O'-Dibenzoyl-(2S,3S)-tartaric Acid; (2S,3S)-2,3-Bis(benzoyloxy)succinic Acid; NSC 97424; Di-O-benzoyl D-Tartaric Acid; (+)-Dibenzoyl-D-tartaric acid; (+)-Dibenzoyl-D-tartaric acid, anhydrous; (+)-O,O′-二苯甲酰-D-酒石酸; 二苯甲酰基-D-酒石酸; D-(+)-二苯甲酰酒石酸; (+)-二苯甲酰基-D-酒石酸,无水

Database IDs

• CAS Number: 17026-42-5
• EC Number: 241-097-1
• MDL Number: MFCD00063222
• Beilstein Number: 2227343
• PubChem SID: 162035545; 24860082; 24849748
• PubChem CID: 1550213

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: 140-145°C; 150-155 °C; 154-156 °C(lit.); 154-156°C
• Optical Rotation: [α]20/D +117±2°, c = 5% in ethanol; [α]28/D +116°, c = 9 in ethanol; +120 (c=5 in methanol)

Safety Information

• Storage Condition: Refrigerator
• Storage Warning: Hygroscopic; IRRITANT
• European Hazard Symbols: Irritant (Xi)
• German water hazard class: 3
• Risk Statements: 36
• Safety Statements: 26; 26-36
• TSCA Listed: false; 是
• GHS Pictograms: GHS07
• GHS Signal Word: Warning
• GHS Hazard statements: H319
• GHS Precautionary statements: P280-P264-P305+P351+P338-P337+P313; P305 + P351 + P338
• Personal Protective Equipment: dust mask type N95 (US), Eyeshields, Gloves

Product Information

• Purity: ≥98%; ≥99.0% (T); 95+%; 99%
• Impurities: ≤1% water
• Linear Formula: [C6H5CO2CH(CO2H)]2

DETAILS

MP Biomedicals - 05202689

MP Biomedicals Rare Chemical collection

Sigma Aldrich - 163449

Packaging
10, 50 g in poly bottle
Application
Reagent for chiral resolution of amino compounds.1,2

Sigma Aldrich - 33610

Other Notes
Reagent for the resolution of bases1,2,3
Packaging
50, 250 g in poly bottle

Toronto Research Chemicals - D417325

Reagent used to produce chiral salts.

REFERENCES

• An, J., et al.: J. Med. Chem., 52, 2667 (2009)