Xanthohumol

Base Information

• Chemical Name: Xanthohumol
• CAS No.: 6754-58-1
• Molecular Formula: C₂₁H₂₂O₅
• Molecular Weight: 354.403
• Hs Code.: 29145090
• European Community (EC) Number: 614-078-4
• UNII: T4467YT1NT
• DSSTox Substance ID: DTXSID00893171
• Nikkaji Number: J1.438.271B,J17.881K
• Wikipedia: Xanthohumol
• Wikidata: Q408088,Q27166535
• NCI Thesaurus Code: C121950
• Metabolomics Workbench ID: 26770
• ChEMBL ID: CHEMBL253896
• Mol file: 6754-58-1.mol

Synonyms:(2E)-1-(2,4-dihydroxy-6-methoxy-3-(3-methyl-2-buten-1-yl)phenyl)-3-(4-hydroxyphenyl)-2-propen-1-one;(2E)-3-(4-hydroxyphenyl)-1-(2,4,6-trihydroxy-3-(3-methyl-2-buten-1-yl)phenyl)-2-propen-1-one;1-(2,4-dihydroxy-6-methoxy-3-(3-methyl-2-butenyl)phenyl)-3-(4-hydroxyphenyl)-2-propen-1-one;2,4,4',6-tetrahydroxy-3-(3,3-dimethylallyl)chalcone;desmethylxanthohumol;Xantho-Flav;XanthoFlav;xanthohumol

Chemical Property of Xanthohumol

Chemical Property:

• Appearance/Colour: Orange powder
• Vapor Pressure: 6.82E-14mmHg at 25°C
• Melting Point: 157-159oC
• Refractive Index: 1.641
• Boiling Point: 576.5 °C at 760 mmHg
• PKA: 7.59±0.45(Predicted)
• Flash Point: 203.4 °C
• PSA: 86.99000
• Density: 1.244 g/cm³
• LogP: 4.21680
• Storage Temp.: 2-8°C
• Solubility.: ethanol: soluble10mg/mL
• XLogP3: 5.1
• Hydrogen Bond Donor Count: 3
• Hydrogen Bond Acceptor Count: 5
• Rotatable Bond Count: 6
• Exact Mass: 354.14672380
• Heavy Atom Count: 26
• Complexity: 515

Purity/Quality:

99% ^*data from raw suppliers

Xanthohumol ^*data from reagent suppliers

Safty Information:

• Pictogram(s): N
• Hazard Codes: N,Xi
• Statements: 50/53-43
• Safety Statements: 60-61-45-22

MSDS Files:

SDS file from LookChem

Total 1 MSDS from other Authors

Useful:

• Canonical SMILES: CC(=CCC1=C(C(=C(C=C1O)OC)C(=O)C=CC2=CC=C(C=C2)O)O)C
• Isomeric SMILES: CC(=CCC1=C(C(=C(C=C1O)OC)C(=O)/C=C/C2=CC=C(C=C2)O)O)C
• Recent ClinicalTrials: Xanthohumol Metabolism and Signature
• Description: Xanthohumol (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)1. Impairs prostate cancer cell growth and proliferation2. Cell permeable.
• Uses: Xanthohumol 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) 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 Reference standard in the analysis of herbal medicinal products.

Technology Process of Xanthohumol

There total 23 articles about Xanthohumol which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield: 98.0%

isoxanthohumol (521-48-2,70872-29-6) → xanthohumol (569-83-5,6754-58-1)

Guidance literature:

With sodium thioethylate; In N,N-dimethyl-formamide;

DOI:10.1016/j.tet.2006.04.060

Reference yield: 64.0%

2′,4,4′-trimethoxymethoxy-6′-methoxy-3′-prenylchalcone → xanthohumol (569-83-5,6754-58-1)

Guidance literature:

With hydrogenchloride; In methanol; for 0.25h; Heating;

DOI:10.1016/j.bmc.2008.02.079

Reference yield: 50.0%

2',4',4-trihydroxy-6'methoxy-3-(3-methylbut-2-en-1-yloxy)chalcone → xanthohumol (569-83-5,6754-58-1)

Guidance literature:

With hydrogenchloride; In methanol; water; for 0.5h; Inert atmosphere; Reflux;

DOI:10.1021/jm5016507

upstream raw materials:

isoxanthohumol

1-{2,4-bis(methoxymethoxy)-6-[(3-methylbut-2-en-1-yl)oxy]phenyl}ethanone

1-[6-hydroxy-2,4-bis(methoxymethoxy)-3-(3-methylbut-2-en-1-yl)phenyl]ethanone

3,5-dihydroxyphenol

Downstream raw materials:

sophoraflavanone B

6-prenylnaringenin

(E)-1-(2,4-dihydroxy-3-(2-hydroxy-3-methylbutyl-3-en-1-yl)-6-methoxyphenyl)-3-(4 -hydroxyphenyl)prop-2-en-1-one

Refernces

• 1、 Han, Pei-Pei,Liu, Ke-Xiong,Su, Liang,Wang, Qiu-An. "Synthesis and Antiproliferative Activity of Prenylated Chalcone Mannich Base Derivatives". . p. 425 - 431. Retrieved 2021/05/29.
• 2、 Yao, Juan,Zhang, Baoxin,Ge, Chunpo,Peng, Shoujiao,Fang, Jianguo. "Xanthohumol, a polyphenol chalcone present in hops, activating nrf2 enzymes to confer protection against oxidative damage in pc12 cells". . p. 1521 - 1531. Retrieved 2015/03/05.