Xanthohumol Chemical Properties

Melting point:

157-159℃

Boiling point:

576.5±50.0 °C(Predicted)

Density 

1.244

storage temp. 

2-8°C

solubility 

ethanol: soluble10mg/mL

form 

powder

pka

7.59±0.45(Predicted)

color 

Yellow

Stability:

Stable for 2 years from date of purchase as supplied. Solutions in DMSO or ethanol may be stored at -20°C for up to 1 month.

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/b11-7+

InChIKey

ORXQGKIUCDPEAJ-YRNVUSSQSA-N

SMILES

C(C1=C(OC)C=C(O)C(C/C=C(/C)\C)=C1O)(=O)/C=C/C1=CC=C(O)C=C1

LogP

5.172 (est)

Safety Information

Hazard Codes 

N,Xi

Risk Statements 

50/53-43

Safety Statements 

60-61-45-22

RIDADR 

UN 3077 9/PG 3

WGK Germany 

3

RTECS 

UD5574117

HS Code 

29145090

Xanthohumol Usage And Synthesis

Description

Xanthohumol(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.

Chemical Properties

Xanthohumol is a Light yellow to Brown powder to crystal. It can dissolve in ethanol. This compound is a natural prenylated chalcone isolated from the hop plant, H. lupulus. Xanthohumol and its metabolites induce protective detoxification enzymes, at least in part via the nuclear factor erythroid-2-related factor 2 pathway.

Uses

Xanthohumol from hop (Humulus lupulus) has been used:
to treat glioblastoma cells to test its effect on inducing apoptosis
to test its protective effect in renal ischemia/reperfusion (I/R) injury
as 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

Definition

ChEBI: 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-).

Application

Xanthohumol is the prenylated chalcone isolated from the female inflorescences of the hop plant (Humulus lupulus L.), an ingredient of beer, have long been used in traditional medicine. Xanthohumol is one of the bioactive substances, and has been reported that it has various pharmacological activities, including antioxidant, anti-inflammatory, anti-proliferative, and osteogenic effects. 

General Description

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

Biochem/physiol Actions

Xanthohumol induces apoptosis in glioma cancer by modulating microRNA based network. It exhibits anti-inflammatory property by inhibiting janus kinases (JAKs), signal transducer and activator of transcription proteins (STATs). Xanthohumol elicits antiviral functionality against bovine viral diarrhea virus (BVDV) and anti-hepatitis C virus in vitro. It also induces autophagy and has antiplatelet and neuroprotective effects. Xanthohumol also regulates various metabolic processes including the inhibition of triglyceride formation, atherosclerotic plaque and adipogenesis.

storage

Store at +4°C

References

[1] YUKIKO SASAZAWA. Xanthohumol Impairs Autophagosome Maturation through Direct Inhibition of Valosin-Containing Protein[J]. ACS Chemical Biology, 2012, 7 5: 892-900. DOI:10.1021/cb200492h.
[2] ROBERTA VENè. Xanthohumol impairs human prostate cancer cell growth and invasion and diminishes the incidence and progression of advanced tumors in TRAMP mice.[J]. Molecular Medicine, 2012, 18: 1292-1302. DOI:10.2119/molmed.2012.00174.
[3] VIOLETTA KRAJKA-KU?NIAK  Wanda B D Jaros?aw Paluszczak. Xanthohumol induces phase II enzymes via Nrf2 in human hepatocytes in vitro[J]. Toxicology in Vitro, 2013, 27 1: Pages 149-156. DOI:10.1016/j.tiv.2012.10.008.
[4] BIRGIT M. DIETZ  Judy L B. Biological reactive intermediates (BRIs) formed from botanical dietary supplements[J]. Chemico-Biological Interactions, 2011, 192 1: Pages 72-80. DOI:10.1016/j.cbi.2010.10.007.
[5] SOSMITHA GIRISA. Xanthohumol from Hop: Hope for cancer prevention and treatment[J]. IUBMB Life, 2021, 73 8: 1016-1044. DOI:10.1002/iub.2522.

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