(2E)-1-[2,4-dihydroxy-6-methoxy-3-(3-methylbut-2-en-1-yl)phenyl]-3-(4-hydroxyphenyl)prop-2-en-1-one

• ChemBase ID: 130198
• Molecular Formular: C21H22O5
• Molecular Mass: 354.39638
• Monoisotopic Mass: 354.1467238
• SMILES: O=C(c1c(OC)cc(O)c(c1O)CC=C(C)C)/C=C/c1ccc(O)cc1
• Canonical SMILES: COc1cc(O)c(c(c1C(=O)/C=C/c1ccc(cc1)O)O)CC=C(C)C
• InChI: InChI=1S/C21H22O5/c1-13(2)4-10-16-18(24)12-19(26-3)20(21(16)25)17(23)11-7-14-5-8-15(22)9-6-14/h4-9,11-12,22,24-25H,10H2,1-3H3
• InChIKey: ORXQGKIUCDPEAJ-UHFFFAOYSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (2E)-1-[2,4-dihydroxy-6-methoxy-3-(3-methylbut-2-en-1-yl)phenyl]-3-(4-hydroxyphenyl)prop-2-en-1-one; 1-[2,4-dihydroxy-6-methoxy-3-(3-methylbut-2-en-1-yl)phenyl]-3-(4-hydroxyphenyl)prop-2-en-1-one
• IUPAC Traditional name: xanthohumol; 1-[2,4-dihydroxy-6-methoxy-3-(3-methylbut-2-en-1-yl)phenyl]-3-(4-hydroxyphenyl)prop-2-en-1-one
• Synonyms: Xanthohumol from hop (Humulus lupulus); 2',4,4'-Trihydroxy-6'-methoxy-3'-prenylchalcone; Desmethylxanthohumol; Xanthohumol; (E)-1-[2,4-Dihydroxy-6-methoxy-3-(3-methyl-2-butenyl)phenyl]-3-(4-hydroxyphenyl)propenone; 2′,4,4′-Trihydroxy-6′-methoxy-3′-prenylchalcone; Xanthohumol; 黄腐醇 来源于啤酒花 (Humulus lupulus); (E)-1-[2,4-二羟基-6-甲氧基-3-(3-甲基-2-丁烯基)苯基]-3-(4-羟基苯基)丙烯酮; 2′,4,4′-三羟基-6′-甲氧基-3′-异戊烯基查耳酮; 黄腐醇

Database IDs

• CAS Number: 6754-58-1; 569-83-5
• MDL Number: MFCD00210576
• PubChem SID: 162224482; 24902121
• PubChem CID: 639665
• CHEMBL: 253896
• Chemspider ID: 555077
• Unique Ingredient Identifier: T4467YT1NT
• Wikipedia Title: Xanthohumol

CALCULATED PROPERTIES

• Acid pKa: 7.010896
• H Acceptors: 5
• H Donor: 3
• LogD (pH = 5.5): 5.187427
• LogD (pH = 7.4): 4.6460238
• Log P: 5.2005253
• Molar Refractivity: 103.5257 cm^3
• Polarizability: 38.62526 Å^3
• Polar Surface Area: 86.99 Å^2
• Rotatable Bonds: 6
• Lipinski's Rule of Five: false

PROPERTIES

Physical Property

• Solubility: DMSO: soluble25 mg/mL; ethanol: soluble10 mg/mL
• Apperance: Orange powder; powder

Safety Information

• European Hazard Symbols: Nature polluting (N); Irritant (Xi)
• UN Number: 3077
• German water hazard class: 3
• Hazard Class: 9
• Packing Group: 3
• Risk Statements: 43-50/53
• Safety Statements: 22-45-60-61
• GHS Pictograms: GHS07; GHS09
• GHS Signal Word: Warning
• GHS Hazard statements: H317-H400
• GHS Precautionary statements: P273-P280
• Personal Protective Equipment: Eyeshields, Faceshields, Gloves
• RID/ADR: UN 3077 9/PG 3
• Storage Temperature: 2-8°C

Product Information

• Purity: ≥96% (HPLC); 99.0
• Grade: primary reference standard
• Empirical Formula (Hill Notation): C21H22O5

DETAILS

Sigma Aldrich - X0379

Biochem/physiol Actions
Prenylated flavonoids such as xanthohumol have antiproliferative and cytotoxic effects in human cancer cell lines1. Xanthohumol protected HepG2 cells against benzo[a]pyrene and related carcinogens. It also protected against reactive oxygen species (ROS), not by a direct anti-oxidant effect, but instead mediated by induction of cellular defense mechanisms against oxidative stress.2Xanthohumol inhibits diacylglycerol acetyltransferase (DGAT)3 and human P450 enzymes4. It also inhibits the expression of HIF-1α and VEGF under hypoxic conditions5.
Protocols & Applications
Hops (Humulus lupulus) Plant Profile: bioactives, mechanism of action, references

Sigma Aldrich - 01130595

Application
Reference standard in the analysis of herbal medicinal products.
General description
Produced and qualified by HWI AnalytikExact content by quantitative NMR can be found on the certificate