(2R,3S)-4-methylidene-5-oxo-2-propyloxolane-3-carboxylic acid

• ChemBase ID: 154725
• Molecular Formular: C9H12O4
• Molecular Mass: 184.18918
• Monoisotopic Mass: 184.07355886
• SMILES: CCC[C@@H]1[C@H](C(=C)C(=O)O1)C(=O)O
• Canonical SMILES: CCC[C@H]1OC(=O)C(=C)[C@@H]1C(=O)O
• InChI: InChI=1S/C9H12O4/c1-3-4-6-7(8(10)11)5(2)9(12)13-6/h6-7H,2-4H2,1H3,(H,10,11)/t6-,7+/m1/s1
• InChIKey: SRQUTZJZABSZRQ-RQJHMYQMSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (2R,3S)-4-methylidene-5-oxo-2-propyloxolane-3-carboxylic acid
• IUPAC Traditional name: (2R,3S)-4-methylidene-5-oxo-2-propyloxolane-3-carboxylic acid
• Synonyms: (2R,3S)-rel-4-Methylene-5-oxo-2-propyltetrahydrofuran-3-carboxylic acid; MB-3

Database IDs

• MDL Number: MFCD08702690
• PubChem SID: 162248863
• PubChem CID: 21579153

CALCULATED PROPERTIES

• Acid pKa: 4.13932
• H Acceptors: 3
• H Donor: 1
• LogD (pH = 5.5): 0.22023793
• LogD (pH = 7.4): -1.4772905
• Log P: 1.5965103
• Molar Refractivity: 44.3157 cm^3
• Polarizability: 17.69615 Å^3
• Polar Surface Area: 63.6 Å^2
• Rotatable Bonds: 3
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Solubility: DMSO: ≥20 mg/mL; H2O: ≥10 mg/mL
• Apperance: white to off-white powder

Safety Information

• German water hazard class: nwg
• GHS Pictograms: GHS07
• GHS Signal Word: Warning
• GHS Hazard statements: H319
• GHS Precautionary statements: P305 + P351 + P338
• Storage Temperature: -20°C

Product Information

• Purity: ≥95% (HPLC)
• Empirical Formula (Hill Notation): C9H12O4

DETAILS

Sigma Aldrich - M2449

Biochem/physiol Actions
MB-3 is a Gcn5 HAT (Histone Acetyltransferase) inhibitor; anti-inflammatory, anti-carcinogenic.