(2S)-7-hydroxy-2-(4-hydroxyphenyl)-3,4-dihydro-2H-1-benzopyran-4-one

• ChemBase ID: 3261
• Molecular Formular: C15H12O4
• Molecular Mass: 256.25338
• Monoisotopic Mass: 256.07355886
• SMILES: Oc1ccc(cc1)[C@@H]1CC(=O)c2ccc(O)cc2O1
• Canonical SMILES: Oc1ccc(cc1)[C@@H]1CC(=O)c2c(O1)cc(cc2)O
• InChI: InChI=1S/C15H12O4/c16-10-3-1-9(2-4-10)14-8-13(18)12-6-5-11(17)7-15(12)19-14/h1-7,14,16-17H,8H2/t14-/m0/s1
• InChIKey: FURUXTVZLHCCNA-AWEZNQCLSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (2S)-7-hydroxy-2-(4-hydroxyphenyl)-3,4-dihydro-2H-1-benzopyran-4-one
• IUPAC Traditional name: (2S)-7-hydroxy-2-(4-hydroxyphenyl)-2,3-dihydro-1-benzopyran-4-one; 5-deoxyflavanone
• Synonyms: 5-Deoxyflavanone; (2S)-7-Hydroxy-2-(4-hydroxyphenyl)-2,3-dihydro-4H-1-benzopyran-4-one; 7,4′-Dihydroxyflavanone; (-)-Liquiritigenin Radix glycyrrhizae; 4',7-Dihydroxyflavanone; Liquiritigenin

Database IDs

• CAS Number: 578-86-9
• MDL Number: MFCD00287289
• Beilstein Number: 359378
• PubChem SID: 46505285; 160966703
• PubChem CID: 114829
• Chemspider ID: 102790
• Wikipedia Title: Liquiritigenin

CALCULATED PROPERTIES

JChem

• Acid pKa: 7.788865
• H Acceptors: 4
• H Donor: 2
• LogD (pH = 5.5): 2.4864612
• LogD (pH = 7.4): 2.340112
• Log P: 2.4886734
• Molar Refractivity: 69.3089 cm^3
• Polarizability: 26.657175 Å^3
• Polar Surface Area: 66.76 Å^2
• Rotatable Bonds: 1
• Lipinski's Rule of Five: true

ALOGPS 2.1

• Log P: 2.79
• LOG S: -3.28
• Solubility (Water): 1.33e-01 g/l

PROPERTIES

Safety Information

• RTECS: DJ2981789
• German water hazard class: 3

Product Information

• Purity: ≥98.0% (HPLC)
• Impurities: ≤7% water
• Empirical Formula (Hill Notation): C15H12O4
• Classification: Rare Genuine Natural Compounds

DETAILS

DrugBank - DB03601

Drug information: experimental

Sigma Aldrich - 78825

Biochem/physiol Actions
Liquiritigenin is a flavanone found in Radix glycyrrhizae and shown to induce apoptosis in SMM-721 cells by disruption of the mitochondrial membrane potential and increased production of reactive oxygen species. 1