(2S)-2-hydroxybutanedioic acid

• ChemBase ID: 102583
• 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-/m0/s1
• InChIKey: BJEPYKJPYRNKOW-REOHCLBHSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (2S)-2-hydroxybutanedioic acid
• IUPAC Traditional name: (-)-malic acid
• Synonyms: (S)-2-hydroxysuccinic acid; (2S)-2-hydroxybutanedioic acid; (2S)-2-Hydroxybutanedioic Acid; (-)-(S)-Malic Acid; (-)-Hydroxysuccinic Acid; (-)-L-Malic Acid; (-)-Malic Acid; (2S)-2-Hydroxy-succinic Acid; (2S)-Malic Acid; (S)-Malic Acid; Apple Acid; L-(-)-Malic Acid; L-Apple Acid; L-Malic Acid; NSC 9232; S-(-)-Malic Acid; S-2-Hydroxybutanedioic Acid; L-(-)-Malic Acid; L-Hydroxysuccinic acid; L-Hydroxybutanedioic acid; L-MALIC ACID FREE ACID; L-(-)-Malic acid; L-MALIC ACID; L-MALIC ACID, α20D-23.5(C=5.6 PYRIDINE); (S)-(-)-2-Hydroxysuccinic acid; (S)-(-)-Hydroxysuccinic acid; (S)-(-)-Hydrosuccinic acid; (S)-(-)-2-羟基琥珀酸; L-羟基丁二酸; L-苹果酸; L-(-)-苹果酸

Database IDs

• CAS Number: 97-67-6
• EC Number: 202-601-5
• MDL Number: MFCD00064213; MFCD00063990
• Beilstein Number: 1723541
• Merck Index: 145707
• PubChem SID: 24845248; 24897161; 24897010; 24847101; 24896463; 162089277
• PubChem CID: 222656

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

• Solubility: H2O: soluble0.5 M at 20 °C, clear, colorless; Soluble in acetone, dioxane, water, methanol and ethanol. Insoluble in benzene
• Melting Point: 100-106°C; 101 - 103°C; 101-103 °C(lit.); 101-107°C; 103-106 °C
• Flash Point: 220°C(428°F)
• Density: 1.60
• Optical Rotation: [α]20/D -27°, c = 5.5 in pyridine; [α]20/D -30±2°, c = 5.5% in pyridine; -27 (c=5.5 in pyridine)
• Hydrophobicity(logP): -1.52
• pKa: (1) 3.46, (2) 5.10

Safety Information

• Storage Condition: Room Temperature (15-30°C)
• RTECS: ON7175000
• European Hazard Symbols: Irritant (Xi)
• German water hazard class: 3
• Risk Statements: 36/37/38
• Safety Statements: 26; 26-37-60
• TSCA Listed: 是
• GHS Pictograms: GHS07
• GHS Signal Word: Warning
• GHS Hazard statements: H315-H319-H335
• GHS Precautionary statements: P261-P305 + P351 + P338; P261-P305+P351+P338-P302+P352-P321-P405-P501A
• Personal Protective Equipment: dust mask type N95 (US), Eyeshields, Gloves

Product Information

• Purity: ≥95%; ≥99%; ≥99.0%; ≥99.0% (T); 95%; 95-100% (enzymatic); 97%; 99%
• Grade: purum; ReagentPlus®; SAJ special grade
• Optical Purity: ee: 99% (GLC)
• Suitability: suitable for cell culture; suitable for insect cell culture
• Ignition Residue: ≤0.1% (as SO4)
• Impurities: ≤0.01% Phosphorus (P); ≤0.1% Insoluble matter; ≤0.3% water
• Cation Traces: Al: ≤0.0005%; Ca: ≤0.0005%; Cu: ≤0.0005%; Fe: ≤0.0005%; Fe: ≤10 mg/kg; K: ≤0.005%; Mg: ≤0.0005%; Na: ≤0.005%; NH4+: ≤0.05%; Pb: ≤0.001%; Zn: ≤0.0005%
• Antion Traces: chloride (Cl-): ≤0.05%; sulfate (SO42-): ≤0.05%
• Ash: <0.1%
• Linear Formula: HO2CCH2CH(OH)CO2H

DETAILS

MP Biomedicals - 02194700

Cell Culture Reagent
Crystalline
Free Acid
Purity: 99%

MP Biomedicals - 05214207

MP Biomedicals Rare Chemical collection

MP Biomedicals - 02102237

Crystalline
Free Acid
Purity: 99%

Sigma Aldrich - M7397

Biochem/physiol Actions
A TCA (Krebs cycle) intermediate and partner in the malic acid aspartate shuttle.

Sigma Aldrich - 112577

Packaging
25, 100 g in poly bottle
Application
Selective α-amino protecting reagent for amino acid derivatives.1 Versatile synthon for the preparation of chiral compounds including κ-opioid receptor agonists,2 1α,25-dihydroxyvitamin D3 analogue,3 and phoslactomycin B.4

Sigma Aldrich - 02288

Legal Information
ReagentPlus is a registered trademark of Sigma-Aldrich Co. LLC

Sigma Aldrich - 02290

Other Notes
Preparation of (S) 2-acetoxysuccinyl chloride1; Preparation of 1-mono-methyl malate2,3; Preparation of hydroxysuccinimide derivatives4; Stereoselective α-alkylation via dioxolanone5

Toronto Research Chemicals - M159505

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)
• Resolving agent for chiral amines; see, for example: Org. Synth. Coll., 2, 506 (1943).