(2S)-5-hydroxy-7-methoxy-2-phenyl-3,4-dihydro-2H-1-benzopyran-4-one

• ChemBase ID: 156826
• Molecular Formular: C16H14O4
• Molecular Mass: 270.27996
• Monoisotopic Mass: 270.08920893
• SMILES: COc1cc(c2c(c1)O[C@@H](CC2=O)c1ccccc1)O
• Canonical SMILES: COc1cc2O[C@@H](CC(=O)c2c(c1)O)c1ccccc1
• InChI: InChI=1S/C16H14O4/c1-19-11-7-12(17)16-13(18)9-14(20-15(16)8-11)10-5-3-2-4-6-10/h2-8,14,17H,9H2,1H3/t14-/m0/s1
• InChIKey: ORJDDOBAOGKRJV-AWEZNQCLSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (2S)-5-hydroxy-7-methoxy-2-phenyl-3,4-dihydro-2H-1-benzopyran-4-one
• IUPAC Traditional name: pinostrobin
• Synonyms: 5-Hydroxy-7-methoxyflavanone; (S)-2,3-Dihydro-5-hydroxy-7-methoxy-2-phenyl-4H-1-benzopyran-4-one; Pinostrobin

Database IDs

• CAS Number: 480-37-5
• EC Number: 207-548-1
• MDL Number: MFCD06858342
• Beilstein Number: 270230
• PubChem SID: 162250963; 24887567
• PubChem CID: 73201

CALCULATED PROPERTIES

• Acid pKa: 8.690532
• H Acceptors: 4
• H Donor: 1
• LogD (pH = 5.5): 3.2842896
• LogD (pH = 7.4): 3.2630508
• Log P: 3.2845674
• Molar Refractivity: 73.7912 cm^3
• Polarizability: 28.569202 Å^3
• Polar Surface Area: 55.76 Å^2
• Rotatable Bonds: 2
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Apperance: Powder

Safety Information

• European Hazard Symbols: Irritant (Xi)
• German water hazard class: 3
• Risk Statements: 36/37/38
• Safety Statements: 26-36
• 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: ≥99.0% (TLC); 98.5
• Empirical Formula (Hill Notation): C16H14O4

DETAILS

Sigma Aldrich - 80614

Biochem/physiol Actions
Elicits intense apoptotic response from cultured leukemia cells in vitro.1 Strongly inhibits the Ca2+ signals involved in the control of G2/M phase cell cycle progression in Saccharomyces cerevisiae.2 Shows potent antiviral effect against herpes simplex virus-1.3
Other Notes
Tandem Mass Spectrometry data independently generated by Scripps Center for Metabolomics is available to view or download in PDF. 80614.pdf Tested metabolites are featured on Scripps Center for Metabolomics METLIN Metabolite Database. To learn more, visit sigma.com/metlin.