Desmethylxanthohumol

Base Information

• Chemical Name: Desmethylxanthohumol
• CAS No.: 115063-39-3
• Molecular Formula: C20H20O5
• Molecular Weight: 340.376
• UNII: 8L48JN7T3E
• DSSTox Substance ID: DTXSID901315295
• Nikkaji Number: J1.068.808F,J3.588.293F
• Wikidata: Q27149540
• Metabolomics Workbench ID: 44476
• ChEMBL ID: CHEMBL466143
• Mol file: 115063-39-3.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 Desmethylxanthohumol

Chemical Property:

• Vapor Pressure: 1.26E-13mmHg at 25°C
• Melting Point: 154-155 °C
• Refractive Index: 1.679
• Boiling Point: 570.7 °C at 760 mmHg
• PKA: 7.35±0.50(Predicted)
• Flash Point: 313 °C
• PSA: 97.99000
• Density: 1.312 g/cm³
• LogP: 3.91380
• XLogP3: 4.7
• Hydrogen Bond Donor Count: 4
• Hydrogen Bond Acceptor Count: 5
• Rotatable Bond Count: 5
• Exact Mass: 340.13107373
• Heavy Atom Count: 25
• Complexity: 500

Purity/Quality:

≥98% ^*data from raw suppliers

Desmethylxanthohumol ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CC(=CCC1=C(C(=C(C=C1O)O)C(=O)C=CC2=CC=C(C=C2)O)O)C
• Isomeric SMILES: CC(=CCC1=C(C(=C(C=C1O)O)C(=O)/C=C/C2=CC=C(C=C2)O)O)C

Technology Process of Desmethylxanthohumol

There total 13 articles about Desmethylxanthohumol 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: 84.0%

(E)-1-(3-prenyl-2,4,6-tris(methoxymethoxy)phenyl)-3-(4-(methoxymethoxy)phenyl)prop-2-en-1-one → desmethylxanthohumol (115063-39-3)

Guidance literature:

With hydrogenchloride; In tetrahydrofuran; methanol; water; at 0 - 50 ℃; for 4h;

DOI:10.1016/j.ejmech.2020.112649

Reference yield: 43.0%

2′,4,4′-trimethoxymethoxy-6′-hydroxy-3′-prenylchalcone (199393-58-3) → desmethylxanthohumol (115063-39-3)

Guidance literature:

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

DOI:10.1016/j.bmc.2008.02.079

Reference yield: 27.0%

2'-hydroxy-4,4',6'-tris(methoxymethoxy)-3'-(3-methyl-2-butenyl)chalcone → desmethylxanthohumol (115063-39-3)

Guidance literature:

In hydrogenchloride; methanol;

upstream raw materials:

2′,4,4′-trimethoxymethoxy-6′-hydroxy-3′-prenylchalcone

5,7,4'-trihydroxy-6-prenylflavanone

2,4,6-trihydroxyacetophenone

4-hydroxy-benzaldehyde

Downstream raw materials:

5,7-Dihydroxy-2-(4-hydroxy-phenyl)-8-(3-methyl-but-2-enyl)-chroman-4-one

isoxanthohumol

5,7,4'-trihydroxy-6-prenylflavanone

4',5-dihydroxy-6'',6''-dimethyl-5'',6''-dihydro-4''H-pyrano[2'',3'':7,8]flavanone

Refernces

• 1、 Zhang, Mengdi,Wang, Zhaoxin,Hao, Siyu,Hao, Lei,Zhang, Xinying,Yu, Peng,Sun, Hua. "Synthesis of natural 3′-Prenylchalconaringenin and biological evaluation of ameliorating non-alcoholic fatty liver disease and metabolic syndrome". . . Retrieved 2020.
• 2、 -. "Remedies". . . Retrieved 2008/06/13.