| Identification | Back Directory | [Name]
ISOXANTHOHUMOL | [CAS]
521-48-2 | [Synonyms]
ISOXANTHOHUMOL
4',7-DIHYDROXY-5-METHOXY-8-PRENYLFLAVANONE
4',7-Dihydroxy-5-methoxy-8-(3-methyl-2-butenyl)flavanone
2-(4-Hydroxyphenyl)-5-methoxy-7-hydroxy-8-(3-methyl-2-butenyl)-2,3-dihydro-4H-1-benzopyran-4-one
2,3-Dihydro-7-hydroxy-2-(4-hydroxyphenyl)-5-methoxy-8-(3-methyl-2-butenyl)-4H-1-benzopyran-4-one
2,3-Dihydro-7-hydroxy-2-(4-hydroxyphenyl)-5-methoxy-8-(3-methyl-2-buten-1-yl)-4H-1-benzopyran-4-one
4H-1-Benzopyran-4-one, 2,3-dihydro-7-hydroxy-2-(4-hydroxyphenyl)-5-methoxy-8-(3-methyl-2-buten-1-yl)- | [Molecular Formula]
C21H22O5 | [MDL Number]
MFCD00238718 | [MOL File]
521-48-2.mol | [Molecular Weight]
354.4 |
| Chemical Properties | Back Directory | [Melting point ]
183 - 187° | [Boiling point ]
585.8±50.0 °C(Predicted) | [density ]
1.245±0.06 g/cm3(Predicted) | [storage temp. ]
2-8°C | [solubility ]
DMSO (Slightly), Methanol (Slightly) | [form ]
powder | [pka]
7.90±0.40(Predicted) | [color ]
Pale Yellow | [BRN ]
10199264 | [Major Application]
metabolomics
vitamins, nutraceuticals, and natural products | [InChI]
InChI=1S/C21H22O5/c1-12(2)4-9-15-16(23)10-19(25-3)20-17(24)11-18(26-21(15)20)13-5-7-14(22)8-6-13/h4-8,10,18,22-23H,9,11H2,1-3H3 | [InChIKey]
YKGCBLWILMDSAV-UHFFFAOYSA-N | [SMILES]
C1(C2=CC=C(O)C=C2)OC2=C(C/C=C(/C)\C)C(O)=CC(OC)=C2C(=O)C1 |
| Hazard Information | Back Directory | [Description]
Isoxanthohumol is a natural, prenylated chalcone isolated from the hop plant, H. lupulus (hops). It has diverse biological activities, including antiproliferative, anti-inflammatory, and antiviral properties.1 In B16 and A375 melanoma cells, isoxanthohumol inhibits proliferation (IC50s = 22.15 and 22.9 μM in an MTT assay), slows cell division, and induces apoptosis.2 Isoxanthohumol reversibly inhibits Kv1.3 channels with an EC50 value of 7.8 μM in human Jurkat T cells using patch clamp electrophysiology.3 It has strong deterrent properties against the peach potato aphid.4 It has also been used as a marker of beer consumption.5 Isoxanthohumol is metabolized in the liver and intestine to 8-prenylnaringenin (Item No. 17462), a potent phytoestrogen.5 | [Uses]
Isoxanthohumol is a prenylated flavone isolated from hop. A chromane-like cyclic prenylflavonoids for neurological disorder therapy. Isoxanthohumol is a prenylated flavonoid phytoestrogen which is an apoptosis inducer in mature adipocytes | [Definition]
ChEBI: Isoxanthohumol is a member of flavanones. | [IC 50]
HSV-1; HSV-2 | [References]
[1] ANNA KATARZYNA ?O?NIERCZYK. Isoxanthohumol — Biologically active hop flavonoid[J]. Fitoterapia, 2015, 103: Pages 71-82. DOI: 10.1016/j.fitote.2015.03.007
[2] TAMARA KRAJNOVI? . Versatile antitumor potential of isoxanthohumol: Enhancement of paclitaxel activity in vivo[J]. Pharmacological research, 2016, 105: Pages 62-73. DOI: 10.1016/j.phrs.2016.01.011
[3] JUSTYNA G?SIOROWSKA. Inhibition of Kv1.3 Channels in Human Jurkat T Cells by Xanthohumol and Isoxanthohumol.[J]. Journal of Membrane Biology, 2015, 248 4: 705-711. DOI: 10.1007/s00232-015-9782-0
[4] PAOLA QUIFER-RADA . Urinary Isoxanthohumol Is a Specific and Accurate Biomarker of Beer Consumptionce1, 2, 3[J]. Journal of Nutrition, 2014, 144 4: Pages 484-488. DOI: 10.3945/jn.113.185199 |
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