(2S,3S)-2,3-bis(4-methylbenzoyloxy)butanedioic acid

• ChemBase ID: 61801
• Molecular Formular: C20H18O8
• Molecular Mass: 386.35212
• Monoisotopic Mass: 386.10016754
• SMILES: C(=O)([C@@H](OC(=O)c1ccc(cc1)C)[C@H](OC(=O)c1ccc(cc1)C)C(=O)O)O
• Canonical SMILES: OC(=O)[C@H]([C@@H](C(=O)O)OC(=O)c1ccc(cc1)C)OC(=O)c1ccc(cc1)C
• InChI: InChI=1S/C20H18O8/c1-11-3-7-13(8-4-11)19(25)27-15(17(21)22)16(18(23)24)28-20(26)14-9-5-12(2)6-10-14/h3-10,15-16H,1-2H3,(H,21,22)(H,23,24)/t15-,16-/m0/s1
• InChIKey: CMIBUZBMZCBCAT-HOTGVXAUSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (2S,3S)-2,3-bis(4-methylbenzoyloxy)butanedioic acid
• IUPAC Traditional name: (2S,3S)-2,3-bis(4-methylbenzoyloxy)butanedioic acid
• Synonyms: (2S,3S)-2,3-Bis((4-methylbenzoyl)oxy)succinic acid; Di-p-toluoyl-D-tartaric acid; Di-p-toluoyl-D-tartaric acid; (+)-O,O′-Di-p-toluoyl-D-tartaric acid; (2S,3S)-(+)-2,3-Bis[(4-methylbenzoyl)oxy]succinic acid; (+)-O,O'-Di-p-toluoyl-D-tartaric acid; (2S,3S)-(+)-2,3-Bis[(4-methylbenzoyl)oxy]butane-1,4-dioic acid; Di-p-toluoyl-D-tartaric acid monohydrate; L-DI-P-TOLULTARTARIC ACID; 二对甲苯酰基-D-酒石酸; (+)-O,O′-二对甲苯酰基-D-酒石酸

Database IDs

• CAS Number: 32634-68-7
• EC Number: 251-132-2
• MDL Number: MFCD00008552; MFCD00149567
• Beilstein Number: 3225584
• PubChem SID: 24867437; 24858275; 162027540
• PubChem CID: 263211

CALCULATED PROPERTIES

• Acid pKa: 2.8210018
• H Acceptors: 6
• H Donor: 2
• LogD (pH = 5.5): 0.7829022
• LogD (pH = 7.4): -1.8656341
• Log P: 4.1886425
• Molar Refractivity: 95.9398 cm^3
• Polarizability: 37.12853 Å^3
• Polar Surface Area: 127.2 Å^2
• Rotatable Bonds: 9
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Melting Point: 169-171 °C(lit.); 169-171°C
• Optical Rotation: [α]19/D +138°, c = 1 in ethanol; [α]20/D +139±2°, c = 1% in ethanol

Safety Information

• Storage Warning: IRRITANT; Irritant
• German water hazard class: 3
• TSCA Listed: true
• Personal Protective Equipment: Eyeshields, Gloves, type N95 (US), type P1 (EN143) respirator filter

Product Information

• Purity: ≥98.0%; 97%; 98%
• Grade: purum
• Linear Formula: [CH3C6H4CO2CH(CO2H)-]2

DETAILS

MP Biomedicals - 05206252

MP Biomedicals Rare Chemical collection

Sigma Aldrich - 302813

Packaging
25, 100 g in poly bottle
5 g in glass bottle

Sigma Aldrich - 43822

Other Notes
Reagent used for the resolution of bases1