(2R)-2-hydroxybutanedioic acid

• ChemBase ID: 102870
• Molecular Formular: C4H6O5
• Molecular Mass: 134.08744
• Monoisotopic Mass: 134.02152329
• SMILES: O[C@H](CC(=O)O)C(=O)O
• Canonical SMILES: OC(=O)C[C@H](C(=O)O)O
• InChI: InChI=1S/C4H6O5/c5-2(4(8)9)1-3(6)7/h2,5H,1H2,(H,6,7)(H,8,9)/t2-/m1/s1
• InChIKey: BJEPYKJPYRNKOW-UWTATZPHSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (2R)-2-hydroxybutanedioic acid
• IUPAC Traditional name: .+-.-malic acid
• Synonyms: D-Hydroxybutanedioic acid; (R)-(+)-2-Hydroxysuccinic acid; D-(+)-MALIC ACID; (2R)-2-Hydroxybutanedioic Acid; D-Malic Acid; (+)-Malic acid; (2R)-2-Hydroxy-butanedioic Acid; (2R)-Malic Acid; (R)-(+)-Malic Acid; (R)-Malic Acid; D-(+)-2-Hydroxysuccinic Acid; D-(+)-Malic Acid; D-(+)-Malic acid; (2R)-2-hydroxybutanedioic acid; (R)-(+)-2-羟基琥珀酸; D-羟基丁二酸; D-(+)-苹果酸

Database IDs

• CAS Number: 636-61-3
• EC Number: 211-262-2
• MDL Number: MFCD00004245
• Beilstein Number: 1723540
• PubChem SID: 24845249; 162088298
• PubChem CID: 92824

CALCULATED PROPERTIES

• Acid pKa: 3.198357
• H Acceptors: 5
• H Donor: 3
• LogD (pH = 5.5): -3.9168313
• LogD (pH = 7.4): -6.814561
• Log P: -1.1136414
• Molar Refractivity: 24.8752 cm^3
• Polarizability: 10.123206 Å^3
• Polar Surface Area: 94.83 Å^2
• Rotatable Bonds: 3
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Apperance: White Crystalline Powder
• Melting Point: 98 - 102°C; 98-102 °C(lit.)
• Optical Rotation: [α]20/D +28.0±2°, c = 5.5% in pyridine
• Hydrophobicity(logP): -1.52

Safety Information

• Storage Condition: Room Temperature (15-30°C)
• RTECS: ON7260000
• European Hazard Symbols: Irritant (Xi)
• German water hazard class: 3
• Risk Statements: 37/38-41
• Safety Statements: 26-36
• GHS Pictograms: GHS05; GHS07
• GHS Signal Word: Danger
• GHS Hazard statements: H315-H318-H335
• GHS Precautionary statements: P261-P280-P305 + P351 + P338
• Personal Protective Equipment: dust mask type N95 (US), Eyeshields, Gloves

Product Information

• Purity: ≥97.0%; ≥97.0% (T); 95%; 98-100%
• Quality: unnatural form
• Linear Formula: HO2CCH2CH(OH)CO2H

DETAILS

MP Biomedicals - 02104835

Crystalline
Purity: 98-100%

Sigma Aldrich - 02300

Other Notes
Tandem Mass Spectrometry data independently generated by Scripps Center for Metabolomics is available to view or download in PDF. 02300.pdf Tested metabolites are featured on Scripps Center for Metabolomics METLIN Metabolite Database. To learn more, visit sigma.com/metlin.

Toronto Research Chemicals - M159500

The naturally occuring isomer is the L-form which has been found in apples and many other fruits and plants. Selective α-amino protecting reagent for amino acid derivatives. Versatile synthon for the preparation of chiral compounds including κ-opioid rece

REFERENCES

• Rindi, G., et al.: Biochem. J., 80, 214 (1961)
• Wolfgang, M., et al.: J. Biol. Chem., 281, 37265 (1961)
• Navarro, D., et al.: Metab. Brain Dis., 23, 115 (1961)