Xanthohumol D Chemical Properties

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

Xanthohumol D Usage And Synthesis

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(274675-25-1)Related Product Information

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• 5,4''-DIHYDROXY-6,7,8-TRIMETHOXYFLAVONE
• 8-PRENYLNARINGENIN
• Chebulinic acid
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• 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