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569-83-5 molecular structure
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(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 and InChIs

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

Cite this record

CBID:130198 http://www.chembase.cn/molecule-130198.html

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NAMES AND DATABASE IDS

NAMES AND DATABASE IDS

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

DATA SOURCES

DATA SOURCES

All Sources Commercial Sources Non-commercial Sources

CALCULATED PROPERTIES

CALCULATED PROPERTIES

JChem
Acid pKa 7.010896  H Acceptors
H Donor LogD (pH = 5.5) 5.187427 
LogD (pH = 7.4) 4.6460238  Log P 5.2005253 
Molar Refractivity 103.5257 cm3 Polarizability 38.62526 Å3
Polar Surface Area 86.99 Å2 Rotatable Bonds
Lipinski's Rule of Five false 

PROPERTIES

PROPERTIES

Physical Property Safety Information Product Information Bioassay(PubChem)
Solubility
DMSO: soluble25 mg/mL expand Show data source
ethanol: soluble10 mg/mL expand Show data source
Apperance
Orange powder expand Show data source
powder expand Show data source
European Hazard Symbols
Nature polluting Nature polluting (N) expand Show data source
Irritant Irritant (Xi) expand Show data source
UN Number
3077 expand Show data source
MSDS Link
Download expand Show data source
Download expand Show data source
German water hazard class
3 expand Show data source
Hazard Class
9 expand Show data source
Packing Group
3 expand Show data source
Risk Statements
43-50/53 expand Show data source
Safety Statements
22-45-60-61 expand Show data source
GHS Pictograms
GHS07 expand Show data source
GHS09 expand Show data source
GHS Signal Word
Warning expand Show data source
GHS Hazard statements
H317-H400 expand Show data source
GHS Precautionary statements
P273-P280 expand Show data source
Personal Protective Equipment
Eyeshields, Faceshields, Gloves expand Show data source
RID/ADR
UN 3077 9/PG 3 expand Show data source
Storage Temperature
2-8°C expand Show data source
Purity
≥96% (HPLC) expand Show data source
99.0 expand Show data source
Grade
primary reference standard expand Show data source
Empirical Formula (Hill Notation)
C21H22O5 expand Show data source

DETAILS

DETAILS

Wikipedia Wikipedia Sigma Aldrich Sigma Aldrich
Sigma Aldrich - X0379 external link
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 external link
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

REFERENCES

REFERENCES

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PATENTS

PATENTS

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INTERNET

INTERNET

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