ChemicalBook > CAS DataBase List > Xanthohumol D

Xanthohumol D

Product Name
Xanthohumol D
CAS No.
274675-25-1
Chemical Name
Xanthohumol D
Synonyms
Xanthohumol D;(E)-1-(2,4-Dihydroxy-3-(2-hydroxy-3-methylbut-3-en-1-yl)-6-methoxyphenyl)-3-(4-hydroxyphenyl)prop-2-en-1-one;2-Propen-1-one,1-[2,4-dihydroxy-3-(2-hydroxy-3-methyl-3-buten-1-yl)-6-methoxyphenyl]-3-(4-hydroxyphenyl)-,(2E)-
CBNumber
CB02520076
Molecular Formula
C21H22O6
Formula Weight
370.4
MOL File
274675-25-1.mol
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Xanthohumol D Property

Boiling point:
624.2±55.0 °C(Predicted)
Density 
1.303±0.06 g/cm3(Predicted)
solubility 
Soluble in Chloroform,Dichloromethane,Ethyl Acetate,DMSO,Acetone,etc.
form 
powder
pka
7.13±0.50(Predicted)
color 
Yellow
InChI
InChI=1S/C21H22O6/c1-12(2)17(24)10-15-18(25)11-19(27-3)20(21(15)26)16(23)9-6-13-4-7-14(22)8-5-13/h4-9,11,17,22,24-26H,1,10H2,2-3H3/b9-6+
InChIKey
IIWLGOCXDBSFCM-RMKNXTFCSA-N
SMILES
C(C1=C(OC)C=C(O)C(CC(O)C(C)=C)=C1O)(=O)/C=C/C1=CC=C(O)C=C1
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Hazard and Precautionary Statements (GHS)

Symbol(GHS)
Signal word
Warning
Hazard statements

H302Harmful if swallowed

H315Causes skin irritation

H319Causes serious eye irritation

H335May cause respiratory irritation

Precautionary statements

P261Avoid breathing dust/fume/gas/mist/vapours/spray.

P305+P351+P338IF IN EYES: Rinse cautiously with water for several minutes. Remove contact lenses, if present and easy to do. Continuerinsing.

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N-Bromosuccinimide Price

Biosynth Carbosynth
Product number
XX178046
Product name
Xanthohumol D
Packaging
2mg
Price
$450
Updated
2021/12/16
Biorbyt Ltd
Product number
orb594575
Product name
Xanthohumol D
Packaging
5mg
Price
$513.4
Updated
2021/12/16
Biorbyt Ltd
Product number
orb594575
Product name
Xanthohumol D
Packaging
10mg
Price
$666.4
Updated
2021/12/16
Biosynth Carbosynth
Product number
XX178046
Product name
Xanthohumol D
Packaging
5mg
Price
$700
Updated
2021/12/16
Biosynth Carbosynth
Product number
XX178046
Product name
Xanthohumol D
Packaging
10mg
Price
$1000
Updated
2021/12/16
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Xanthohumol D Chemical Properties,Usage,Production

Uses

Xanthohumol D, isolated from hops, is an inhibitor of quinone reductase-2 (QR-2) with the IC50 value of 110 μM, and binds to the active site of QR-2. Xanthohumol D shows antiproliferative activity on human cancer cell lines in vitro[1][2].

Definition

ChEBI: Xanthohumol D 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 2-hydroxy-3-methylbut-3-en-1-yl group at position 3'. It has been isolated as a racemate from Humulus lupulus and has been shown to exhibit inhibitory activity against NO production. It has a role as a metabolite and an EC 1.14.13.39 (nitric oxide synthase) inhibitor. It is a member of chalcones, a polyphenol, an aromatic ether and a secondary alcohol.

target

IFN-γ | NO

References

[1] Choi Y, et al. Screening natural products for inhibitors of quinone reductase-2 using ultrafiltration LC-MS. Anal Chem. 2011 Feb 1;83(3):1048-52. DOI:10.1021/ac1028424
[2] Tronina T, et al. Fungal metabolites of xanthohumol with potent antiproliferative activity on human cancer cell lines in vitro. Bioorg Med Chem. 2013 Apr 1;21(7):2001-6. DOI:10.1016/j.bmc.2013.01.026

Xanthohumol D Preparation Products And Raw materials

Raw materials

Preparation Products

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274675-25-1, Xanthohumol DRelated Search:

xanthoangelol 5,4''-DIHYDROXY-6,7,8-TRIMETHOXYFLAVONE 8-PRENYLNARINGENIN Chebulinic acid 10-Gingerol HUMULONE chebulagic acid Hydroxytyrosol Acetate DESMETHYLXANTHOHUMOL 3,4-Dimethoxybenzyl alcohol Hydroxytyrosol Xanthohumol 6-PRENYLNARINGENIN Ellagic acid (4E,6E)-1,7-Diphenyl-4,6-heptadien-3-one Chebulic Acid Xanthohumol B 3,4-Dimethoxybenzoic acid

  • Xanthohumol D
  • 2-Propen-1-one,1-[2,4-dihydroxy-3-(2-hydroxy-3-methyl-3-buten-1-yl)-6-methoxyphenyl]-3-(4-hydroxyphenyl)-,(2E)-
  • (E)-1-(2,4-Dihydroxy-3-(2-hydroxy-3-methylbut-3-en-1-yl)-6-methoxyphenyl)-3-(4-hydroxyphenyl)prop-2-en-1-one
  • 274675-25-1