sodium (3R)-3,5-dihydroxy-3-methylpentanoate

• ChemBase ID: 153231
• Molecular Formular: C6H11NaO4
• Molecular Mass: 170.13891
• Monoisotopic Mass: 170.05550311
• SMILES: CC(CCO)(CC(=O)[O-])O.[Na+]
• Canonical SMILES: OCCC(CC(=O)[O-])(O)C.[Na+]
• InChI: InChI=1S/C6H12O4.Na/c1-6(10,2-3-7)4-5(8)9;/h7,10H,2-4H2,1H3,(H,8,9);/q;+1/p-1/t6-;/m1./s1
• InChIKey: RIYNLCMADQUBEM-FYZOBXCZSA-M

NAMES AND DATABASE IDS

Names

• IUPAC name: sodium (3R)-3,5-dihydroxy-3-methylpentanoate
• IUPAC Traditional name: sodium (R)-mevalonate
• Synonyms: Sodium (R)-3,5-dihydroxy-3-methylpentanoate; Sodium (R)-3,5-dihydroxy-3-methylvalerate; (R)-Mevalonic acid sodium salt

Database IDs

• CAS Number: 96949-03-0
• MDL Number: MFCD17215922
• PubChem SID: 162247370
• PubChem CID: 71311618

CALCULATED PROPERTIES

• Acid pKa: 4.384681
• H Acceptors: 4
• H Donor: 2
• LogD (pH = 5.5): -2.2391148
• LogD (pH = 7.4): -3.993144
• Log P: -1.0933796
• Molar Refractivity: 45.3485 cm^3
• Polarizability: 13.548565 Å^3
• Polar Surface Area: 80.59 Å^2
• Rotatable Bonds: 4
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Optical Rotation: [α]/D +8.5±0.5°, c = 1 in 1 M NaOH

Safety Information

• European Hazard Symbols: Irritant (Xi)
• German water hazard class: 3
• Risk Statements: 41
• Safety Statements: 26-39
• GHS Pictograms: GHS05
• GHS Signal Word: Danger
• GHS Hazard statements: H318
• GHS Precautionary statements: P280-P305 + P351 + P338
• Storage Temperature: 2-8°C

Product Information

• Purity: ≥96.0% (GC)
• Impurities: ≤10% water; 13.0-14.1% sodium(calc. on dry substance)
• Empirical Formula (Hill Notation): C6H11NaO4

DETAILS

Sigma Aldrich - 41288

Biochem/physiol Actions
Metabolite of the mevalonate pathway, which plays a key role in the biosynthesis of sterols, dolichol, heme and ubiquinone. Of interest for research in the disease areas oncology, autoimmune diseases, artherosclerosis and Alzheimer disease, as well as for inherited deficiencies of mevalonate kinase.