Xanthohumol

HCID 639665CAS 6754-58-1
Substructure searchFind similar structures

Basic information

Standard SMILES
COc1cc(O)c(CC=C(C)C)c(O)c1C(=O)/C=C/c1ccc(O)cc1
InChIKey
ORXQGKIUCDPEAJ-YRNVUSSQSA-N
Molecular formula
C21H22O5
Average molar mass
354.4 g/mol
Monoisotopic mass
354.1467238

Overview

Xanthohumol is a member of the class of chalcones that is trans-chalcone substituted by hydroxy groups at positions 4, 2' and 4', a methoxy group at position 6' and a prenyl group at position 3'. Isolated from Humulus lupulus, it induces apoptosis in human malignant glioblastoma cells. It has a role as an antiviral agent, a metabolite, an antineoplastic agent, an EC 2.3.1.20 (diacylglycerol O-acyltransferase) inhibitor, an anti-HIV-1 agent and an apoptosis inducer. It is a member of chalcones, a polyphenol and an aromatic ether. It is a conjugate acid of a xanthohumol(1-).

Names & identifiers

Preferred name
Xanthohumol
IUPAC
(E)-1-[2,4-dihydroxy-6-methoxy-3-(3-methylbut-2-enyl)phenyl]-3-(4-hydroxyphenyl)prop-2-en-1-one
English name
Xanthohumol
Molecular formula
C21H22O5
Molecular weight
354.4

Names & synonyms

Xanthohumol6754-58-1Xantho-flav(E)-1-[2,4-dihydroxy-6-methoxy-3-(3-methylbut-2-enyl)phenyl]-3-(4-hydroxyphenyl)prop-2-en-1-oneDTXSID00893171T4467YT1NT(2E)-1-[2,4-dihydroxy-6-methoxy-3-(3-methylbut-2-en-1-yl)phenyl]-3-(4-hydroxyphenyl)prop-2-en-1-oneCHEBI:663311-(2,4-Dihydroxy-6-methoxy-3-(3-methyl-2-butenyl)phenyl)-3-(4-hydroxyphenyl)-2-propen-1-one2-Propen-1-one, 1-(2,4-hydroxy-6-methoxy-3-(3-methyl-2-butenyl)phenyl)-3-(4-hydroxyphenyl)-, (E)-(2E)-1-(2,4-DIHYDROXY-6-METHOXY-3-(3-METHYL-2-BUTEN-1-YL)PHENYL)-3-(4-HYDROXYPHENYL)-2-PROPEN-1-ONE(E)-1-(2,4-dihydroxy-6-methoxy-3-(3-methylbut-2-enyl)phenyl)-3-(4-hydroxyphenyl)prop-2-en-1-one
Show more names
prop-2-en-1-oneXanthohuMoXanthohumol-RMXantho Flav-PureXanthohumol, >99%Xanthohumol 99.8%Xanthohumol StandardXanthohumol (6CI, 7CI)
XanthoFlav(2E)-1-(2,4-Dihydroxy-6-methoxy-3-(3-methylbut-2-en-1-yl)phenyl)-3-(4-hydroxyphenyl)prop-2-en-1-oneRefChem:195131DTXCID6013231103'-(3,3-Dimethyl allyl)-2',4',4-trihydroxy-6'-methoxychalcone614-078-4(E/Z)-XanthohumolMFCD00210576

Database identifiers

CAS
6754-58-1
PubChem CID
639665
DTXSID
DTXSID00893171
ChEMBL
CHEMBL253896
ChEBI
CHEBI:66331
UNII
T4467YT1NT
EC Number
614-078-4
Nikkaji
J1.438.271B、J17.881K

Properties

Computed structural properties

XLogP
5.1
Topological polar surface area
87 Ų
Hydrogen bond donors
3
Hydrogen bond acceptors
5
Rotatable bonds
6
Heavy atoms
26

Experimental & physicochemical properties

LipidsPolyketides [PK] -> Flavonoids [PK12] -> Chalcones and dihydrochalcones [PK1212]
Melting Point172 °C
Physical DescriptionSolid

Physicochemical properties

Melting point
157 · 157-159℃
Boiling point
576.5 · 576.5±50.0 °C(Predicted)
Density
1.244 · 1.244
storage temp.
2 · 2-8°C
solubility
10 mg/mL · ethanol: soluble10mg/mL
form
powder

Safety & regulation

GHS classification

GHS Classification · 5 items

This chemical does not meet GHS hazard criteria for 4.2% (4 of 96) of reports.

Warning

H317 (95.8%): May cause an allergic skin reaction [Warning Sensitization, Skin]

P261, P272, P273, P280, P302+P352, P321, P333+P317, P362+P364, P391, and P501 (click each P-code to see the statement)

Aggregated GHS information provided per 96 reports by companies from 3 notifications to the ECHA C&L Inventory. Each notification may be associated with multiple companies.

Hazard information

Hazard Classes and CategoriesSkin Sens. 1 (95.8%)

Safety data

PPE
Eyeshields, Faceshields, Gloves
wgk
3
rtecs
UD5574117
ridadr
UN 3077 9/PG 3
hs_code
29145090
risk_code
50/53-43

Chemistry & industry

Pharmacology

MeSH Pharmacological Classification · 2 items

Substances that inhibit or prevent the proliferation of NEOPLASMS.

Agents and endogenous substances that antagonize or inhibit the development of new blood vessels.

Cellular LocationsMembrane
Applications · 3 items

DescriptionXanthohumol(XH, 6754-58-1) binds to the N-terminal domain of valosin-containing protein (VCP), an essential protein for autophagosome maturation. Xanthohumol inhibits the function of VCP thereby impairing autophagosome maturation and resulting in accumulation of the microtubule-associated protein 1 light chain 3-II (LC3-II) Impairs prostate cancer cell growth and proliferation Cell permeable.

UsesXanthohumol from hop (Humulus lupulus) has been used:to treat glioblastoma cells to test its effect on inducing apoptosisto test its protective effect in renal ischemia/reperfusion (I/R) injuryas a component of Dulbecco′s modified Eagle medium (DMEM) to test its antiviral activity in Huh7.5 cells infected with hepatitis C virus cell culture (HCVcc) system

General DescriptionXanthohumol (XN), a prenylated chalcone present in Hop (Humulus lupulus), has been found to possess prominent activities against aging, diabetes, inflammation, microbial infection, and cancer.

Suppliers50 total

梯希爱(上海)化成工业发展有限公司021-67121386 · [email protected]
成都普瑞法科技开发有限公司+86-028-82633397 18982077548 · [email protected]
山西玉宁生物科技有限公司13623677056
南京普怡生物科技有限公司13814510036 · [email protected]
合肥翰刚医药科技有限公司+8618062405514 · [email protected]
Additional notes · 1 item

DefinitionChEBI: Xanthohumol is a member of the class of chalcones that is trans-chalcone substituted by hydroxy groups at positions 4, 2' and 4', a methoxy group at position 6' and a prenyl group at position 3'. Isolated from Humulus lupulus, it induces apoptosis in human malignant glioblastoma cells. It has a role as a metabolite, an apoptosis inducer, an antineoplastic agent, an antiviral agent, an EC 2.3.1.20 (diacylglycerol O-acyltransferase) inhibitor and an anti-HIV-1 agent. It is a member of chalcones, a polyphenol and an aromatic ether. It is a conjugate acid of a xanthohumol(1-).

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