(2E)-3-[4-hydroxy-2-methoxy-5-(2-methylbut-3-en-2-yl)phenyl]-1-(4-hydroxyphenyl)prop-2-en-1-one

• ChemBase ID: 128064
• Molecular Formular: C21H22O4
• Molecular Mass: 338.39698
• Monoisotopic Mass: 338.15180918
• SMILES: CC(C)(C=C)c1c(cc(c(c1)/C=C/C(=O)c1ccc(cc1)O)OC)O
• Canonical SMILES: C=CC(c1cc(/C=C/C(=O)c2ccc(cc2)O)c(cc1O)OC)(C)C
• InChI: InChI=1S/C21H22O4/c1-5-21(2,3)17-12-15(20(25-4)13-19(17)24)8-11-18(23)14-6-9-16(22)10-7-14/h5-13,22,24H,1H2,2-4H3/b11-8+
• InChIKey: KAZSKMJFUPEHHW-DHZHZOJOSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (2E)-3-[4-hydroxy-2-methoxy-5-(2-methylbut-3-en-2-yl)phenyl]-1-(4-hydroxyphenyl)prop-2-en-1-one; 3-[4-hydroxy-2-methoxy-5-(2-methylbut-3-en-2-yl)phenyl]-1-(4-hydroxyphenyl)prop-2-en-1-one
• IUPAC Traditional name: licochalcone A
• Synonyms: Licochalcone a; Licochalcone A; (E)-3-[5-(1,1-Dimethyl-2-propenyl)-4-hydroxy-2-methoxyphenyl]-1-(4-hydroxyphenyl)-2-propen-1-one; 4′,4-Dihydroxy-3-α,α-dimethylallyl-6-methoxychalcone; Licochalcone A

Database IDs

• CAS Number: 58749-22-7
• MDL Number: MFCD01417903
• Beilstein Number: 4534154
• PubChem SID: 162222380
• PubChem CID: 5318998
• Wikipedia Title: Licochalcone_A

CALCULATED PROPERTIES

• Acid pKa: 7.8304925
• H Acceptors: 4
• H Donor: 2
• LogD (pH = 5.5): 4.8091483
• LogD (pH = 7.4): 4.671471
• Log P: 4.8111606
• Molar Refractivity: 100.613 cm^3
• Polarizability: 38.021023 Å^3
• Polar Surface Area: 66.76 Å^2
• Rotatable Bonds: 6
• Lipinski's Rule of Five: true

PROPERTIES

Safety Information

• RTECS: UB8755000
• European Hazard Symbols: Harmful (Xn)
• German water hazard class: 3
• Risk Statements: 20/21/22; R20, R21, R22
• Safety Statements: 36/37; S36
• GHS Pictograms: GHS07
• GHS Signal Word: Warning
• GHS Hazard statements: H302-H312-H332
• GHS Precautionary statements: P280
• Personal Protective Equipment: dust mask type N95 (US), Eyeshields, Gloves
• Storage Temperature: -20°C

Product Information

• Purity: ≥96.0% (HPLC)
• Empirical Formula (Hill Notation): C21H22O4

DETAILS

Sigma Aldrich - 68783

Biochem/physiol Actions
Inhibits vegetative growth of spore-forming bacteria, B. subtilis and other food-contaminating microorganisms.
General description
Licochalcone A is a potent membrane-active agent that transforms normal erythrocytes into echinocytes.1 A novel flavanoid which has demonstrated significant antitumor activity.2