2-hydroxybutanedioic acid

• ChemBase ID: 102582
• Molecular Formular: C4H6O5
• Molecular Mass: 134.08744
• Monoisotopic Mass: 134.02152329
• SMILES: OC(CC(=O)O)C(=O)O
• Canonical SMILES: OC(=O)CC(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)
• InChIKey: BJEPYKJPYRNKOW-UHFFFAOYSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: 2-hydroxybutanedioic acid
• IUPAC Traditional name: malic acid
• Synonyms: Hydroxy Succinic Acid; Kyselina Jablecna; DL-Hydroxybutanedioic acid; DL-MALIC ACID; 2-Hydroxybutanedioic Acid; Malic Acid; (+/-)-Malic Acid; 2-Hydroxyethane-1,2-dicarboxylic Acid; 2-Hydroxysuccinic Acid; Deoxytetraric Acid; E 296; FDA 2018; Hydroxysuccinic Acid; Musashi-no-Ringosan; NSC 25941; Nanoveson M; Pomalus Acid; R,S(+/-)-Malic Acid; α-Hydroxysuccinic Acid; (R)-(+)-Hydroxysuccinic acid; D-(+)-Malic acid; (±)-Hydroxysuccinic acid; (±)-2-Hydroxysuccinic acid; DL-Malic acid; DL-Malic acid; Malic acid; L-Malic acid; D-Malic acid; (–)-Malic acid; (+)-Malic acid; (S)-Hydroxybutanedioic acid; (R)-Hydroxybutanedioic acid; Malic acid; D-(+)-苹果酸; (±)-2-羟基琥珀酸; DL-羟基丁二酸; DL-苹果酸; DL-苹果酸; 苹果酸

Database IDs

• CAS Number: 617-48-1; 6915-15-7; 636-61-3
• EC Number: 230-022-8; 211-262-2
• MDL Number: MFCD00004245; MFCD00064212
• Beilstein Number: 1723540; 1723539
• Merck Index: 145707
• PubChem SID: 24856486; 24897242; 24896626; 24896573; 24901221; 162089952; 24854408
• PubChem CID: 525
• CHEBI ID: 6650
• CHEMBL: 1455497
• Chemspider ID: 510
• FEMA ID: 2655
• KEGG ID: C00149
• Unique Ingredient Identifier: 817L1N4CKP
• Wikipedia Title: Malic_acid
• Flavis Number: 8.017

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: 558 g/L (at 20 °C) in water; DMSO; Methanol; methanol: soluble0.1 g/mL, clear, colorless; Soluble in acetone, dioxane, water, methanol and ethanol. Insoluble in benzene.
• Apperance: White Solid
• Melting Point: 100-104°C; 129-131 °C; 129-132 °C; 129-133 °C; 130°C; 130-133°C; 131-133 °C(lit.); 131-133°C; 131-133°C
• Boiling Point: 150°C
• Flash Point: 203°C(397°F)
• Auto Ignition Point: 340°C; 644 °F
• Density: 1.60; 1.601 g/ml; 1.609; 1.609 g cm^-3
• Vapor Pressure: < 0.1 mm Hg (20°C); <0.1 mmHg ( 20 °C)
• Vapor Density: 4.6 (vs air)
• Optical Rotation: [α]/D -0.10 to +0.10°; +28 (c=5.5 in pyridine)
• pKa: pK_a1 = 3.40, pK_a2 = 5.20

Safety Information

• Storage Condition: Refrigerator; Room Temperature (15-30°C)
• RTECS: ON7175000; ON7260000
• European Hazard Symbols: X; Irritant (Xi); Harmful (Xn)
• German water hazard class: 3
• Risk Statements: 22-37/38-41; 37/38-41; R:36
• Safety Statements: 26-36/37/39-60; 26-36/39; 26-37/39; S:26
• TSCA Listed: 否; 是
• GHS Pictograms: GHS05; GHS07
• GHS Signal Word: Danger
• GHS Hazard statements: H302-H315-H318-H335; H318-H315-H302-H335; H318-H315-H335
• GHS Precautionary statements: P261-P280-P305 + P351 + P338; P261-P305+P351+P338-P302+P352-P321-P405-P501A
• Personal Protective Equipment: dust mask type N95 (US), Eyeshields, Gloves

Pharmacology Properties

• Allergens: no known allergens

Product Information

• Purity: ≥98% (capillary GC); ≥99%; ≥99.0%; ≥99.0% (T); 98%; 98+%; 99%; 99-100.5% (alkalimetric)
• Grade: Kosher; puriss.; purum; ReagentPlus®; SAJ first grade
• Suitability: complies for identity (IR); meets USP/NF testing specifications
• Ignition Residue: ≤0.1%; ≤0.1% (as SO4)
• Impurities: ≤0.05% maleic acid; ≤0.1% water insoluble matter; ≤1% fumaric acid
• Cation Traces: As: ≤3 mg/kg; Ca: ≤10 mg/kg; Cd: ≤5 mg/kg; Co: ≤5 mg/kg; Cr: ≤5 mg/kg; Cu: ≤5 mg/kg; Fe: ≤5 mg/kg; Hg: ≤1 mg/kg; K: ≤50 mg/kg; Mg: ≤5 mg/kg; Mn: ≤5 mg/kg; Na: ≤50 mg/kg; Ni: ≤5 mg/kg; Pb: ≤2 mg/kg; Pb: ≤5 mg/kg; Zn: ≤5 mg/kg
• Quality: meets analytical specification of FCC, E296
• Linear Formula: HO2CCH2CH(OH)CO2H

DETAILS

MP Biomedicals - 02102234

Crystalline
Purity: 99%

Sigma Aldrich - W265501

Packaging
1 kg in poly bottle
1 sample in glass bottle
5, 10 kg in fiber drum

Sigma Aldrich - 240176

Packaging
50, 250 g in poly bottle
Legal Information
ReagentPlus is a registered trademark of Sigma-Aldrich Co. LLC

Sigma Aldrich - M1210

Packaging
2 kg in poly bottle
500 g in poly bottle
Legal Information
ReagentPlus is a registered trademark of Sigma-Aldrich Co. LLC

Sigma Aldrich - M0875

Packaging
1 kg in poly bottle
100, 500 g in poly bottle

Toronto Research Chemicals - M159510

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)