2-hydroxy-3-(propan-2-yl)butanedioic acid

• ChemBase ID: 154521
• Molecular Formular: C7H12O5
• Molecular Mass: 176.16718
• Monoisotopic Mass: 176.06847348
• SMILES: CC(C)C(C(C(=O)O)O)C(=O)O
• Canonical SMILES: CC(C(C(C(=O)O)O)C(=O)O)C
• InChI: InChI=1S/C7H12O5/c1-3(2)4(6(9)10)5(8)7(11)12/h3-5,8H,1-2H3,(H,9,10)(H,11,12)
• InChIKey: RNQHMTFBUSSBJQ-UHFFFAOYSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: 2-hydroxy-3-(propan-2-yl)butanedioic acid
• IUPAC Traditional name: 3-isopropylmalic acid
• Synonyms: 2-Hydroxy-3-isopropylsuccinic acid; 3-Isopropylmalic acid

Database IDs

• CAS Number: 16048-89-8
• MDL Number: MFCD16875410
• PubChem SID: 162248660
• PubChem CID: 36

CALCULATED PROPERTIES

• Acid pKa: 3.6770577
• H Acceptors: 5
• H Donor: 3
• LogD (pH = 5.5): -1.9481872
• LogD (pH = 7.4): -5.033675
• Log P: 0.16093262
• Molar Refractivity: 38.5993 cm^3
• Polarizability: 15.484841 Å^3
• Polar Surface Area: 94.83 Å^2
• Rotatable Bonds: 4
• Lipinski's Rule of Five: true

PROPERTIES

Safety Information

• European Hazard Symbols: Irritant (Xi)
• German water hazard class: 3
• Risk Statements: 36/37/38
• Safety Statements: 26
• GHS Pictograms: GHS07
• GHS Signal Word: Warning
• GHS Hazard statements: H315-H319-H335
• GHS Precautionary statements: P261-P305 + P351 + P338
• Personal Protective Equipment: dust mask type N95 (US), Eyeshields, Gloves

Product Information

• Purity: ≥96.0% (GC)
• Empirical Formula (Hill Notation): C7H12O5

DETAILS

Sigma Aldrich - 02339

Biochem/physiol Actions
3-Isopropylmalate is converted to 2-oxoisocaproate by oxidative decarboxylation catalyzed by 3-Isopropylmalate dehydrogenase. 1
Metabolite in leucine biosynthesis; substrate for different enzymes