Xanthohumol

Product Name: Xanthohumol
CAS No.: 6754-58-1
Chemical Name: Xanthohumol
Synonyms: XanthohuMo;XANTHOHUMOL;Xantho-Flav;Xanthohumol-RM;prop-2-en-1-one;Xantho Flav-Pure;Xanthohumol, >99%;Xanthohumol 99.8%;Xanthohumol Standard;Xanthohumol (6CI, 7CI)
CBNumber: CB5128899
Molecular Formula: C21H22O5
Formula Weight: 354.4
MOL File: 6754-58-1.mol

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Xanthohumol Property

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)

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Safety

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

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Hazard and Precautionary Statements (GHS)

Symbol(GHS)

Signal word

Warning

Hazard statements

H317May cause an allergic skin reaction

H400Very toxic to aquatic life

Precautionary statements

P273Avoid release to the environment.

P280Wear protective gloves/protective clothing/eye protection/face protection.

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N-Bromosuccinimide Price

Sigma-Aldrich

Product number: X0379
Product name: Xanthohumol from hop (Humulus lupulus)
Purity: ≥96% (HPLC)
Packaging: 5mg
Price: $354
Updated: 2024/03/01

Sigma-Aldrich

Product number: 01130595
Product name: Xanthohumol
Purity: primary reference standard
Packaging: 10mg
Price: $1120
Updated: 2024/03/01

TCI Chemical

Product number: X0068
Product name: Xanthohumol
Purity: >97.0%(HPLC)
Packaging: 25mg
Price: $904
Updated: 2024/03/01

Cayman Chemical

Product number: 15399
Product name: Xanthohumol
Purity: ≥98%
Packaging: 1mg
Price: $25
Updated: 2024/03/01

Cayman Chemical

Product number: 15399
Product name: Xanthohumol
Purity: ≥98%
Packaging: 5mg
Price: $75
Updated: 2024/03/01

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Xanthohumol Chemical Properties,Usage,Production

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.

Xanthohumol Preparation Products And Raw materials

Raw materials

Preparation Products

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View Lastest Price from Xanthohumol manufacturers

Changsha Staherb Natural Ingredients Co., Ltd.

Product: XANTHOHUMOL 6754-58-1
Price: US $0.00/KG
Min. Order: 1KG
Purity: ≥98% HPLC
Supply Ability: 1000KG
Release date: 2022-11-30

Changsha Staherb Natural Ingredients Co., Ltd.

Product: Xanthohumol Hops Extract 6754-58-1
Price: US $0.00/kg
Min. Order: 1kg
Purity: 3%-99% HPLC
Supply Ability: 1000kg
Release date: 2023-01-13

Hebei Zhuanglai Chemical Trading Co Ltd

Product: Xanthohumol 6754-58-1
Price: US $150.00/kg
Min. Order: 1kg
Purity: 99%
Supply Ability: 500kg
Release date: 2024-12-11

6754-58-1, XanthohumolRelated Search:

(+/-)-Naringenin XANTHOHUMOL xanthoangelol HUMULONE LUPULONE ISOXANTHOHUMOL 4',5-DIHYDROXY-7-METHOXYFLAVONE 8-PRENYLNARINGENIN 2-(3,4-Dihydroxyphenyl)-8-(2-O-beta-L-galactopyranosyl-beta-D-glucopyranosyl)-5,7-dihydroxy-4H-1-Benzopyran-4-one Quercetin-7-O-β-D-glucopyranoside MOSLOFLAVONE Naringenin Xanthohumol D Xanthohumol B Xanthohumol L Xanthohumol I Xanthiazone 2'-HYDROXY-4',6'-DIMETHOXYACETOPHENONE

XANTHOHUMOL

XANTHOHUMOL, HUMULUS LU PULUS

2',4',4-TRIHYDROXY-6'-METHOXY-3'-PRENYLCHALCONE

(2E)-1-[2,4-Dihydroxy-6-methoxy-3-(3-methyl-2-buten-1-yl)phenyl]-3-(4-hydroxyphenyl)-2-propen-1-one

XanthohuMo

Xanthohumol from hop (Humulus lupulus)

1-(2,4-Dihydroxy-6-methoxy-3-(3-methylbut-2-en-1-yl)phenyl)-3-(4-hydroxyphenyl)prop-2-en-1-one

2-Propen-1-one,1-[2,4-dihydroxy-6-Methoxy-3-(3-Methyl-2-buten-1-yl)phenyl]-3-(4-hydroxyphenyl)-,(2E)-

Xanthohumol, >99%

Humulus Lupulus Extract Xanthohumol 6754-58-1 HPLC 95% 98% Yellow Powder

large stock Xanthohumol 6754-58-1

1-(2,4-Dihydroxy-6-methoxy-3-(3-methylbut-2-en-1-yl)

prop-2-en-1-one

Xantho Flav-Pure

Xantho-Flav

1-[2,4-Dihydroxy-6-methoxy-3-(3-methyl-but-2-enyl)-phenyl]-3-(4-hydroxy-phenyl)-propenone

Hops Flower Extract (Standard)

Xanthohumol Standard

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

(E)-1-[2,4-Dihydroxy-6-methoxy-3-(3-methyl-2-butenyl)phenyl]-3-(4-hydroxyphenyl)propenone

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

Xanthohumol ex. Hop (Humulus Lupulus), 94%

Xanthohumol Hops Extract

Xanthohumol (6CI, 7CI)

Xanthohumol 99.8%

Xanthohumol-RM

6754-58-1

Flavaniods

standard material,plant extracts

SiChem