ChemicalBook > CAS DataBase List > ISOXANTHOHUMOL

ISOXANTHOHUMOL

Product Name: ISOXANTHOHUMOL
CAS No.: 521-48-2
Chemical Name: ISOXANTHOHUMOL
Synonyms: ISOXANTHOHUMOL;(±)-Isoxanthohumol;Isoxanthohumol, 10 mM in DMSO;4',7-DIHYDROXY-5-METHOXY-8-PRENYLFLAVANONE;4',7-Dihydroxy-5-methoxy-8-(3-methyl-2-butenyl)flavanone;7-Hydroxy-2-(4-hydroxyphenyl)-5-methoxy-8-(3-methylbut-2-en-1-yl)chroman-4-one;2,3-Dihydro-7-hydroxy-2-(4-hydroxyphenyl)-5-methoxy-8-(3-methyl-2-butenyl)-4H-1-benzopyran-4-one;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-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)-
CBNumber: CB4150547
Molecular Formula: C21H22O5
Formula Weight: 354.4
MOL File: 521-48-2.mol

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ISOXANTHOHUMOL Property

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
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

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Safety

WGK Germany: 3

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Hazard and Precautionary Statements (GHS)

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N-Bromosuccinimide Price

Sigma-Aldrich

Product number: SMB00389
Product name: Isoxanthohumol
Purity: ≥99% (HPLC)
Packaging: 1mg
Price: $123
Updated: 2025/07/31

Sigma-Aldrich

Product number: 55423
Product name: Isoxanthohumol
Purity: analytical standard
Packaging: 5mg
Price: $513
Updated: 2022/05/15

Cayman Chemical

Product number: 23233
Product name: Isoxanthohumol
Purity: ≥98%
Packaging: 500μg
Price: $35
Updated: 2024/03/01

Cayman Chemical

Product number: 23233
Product name: Isoxanthohumol
Purity: ≥98%
Packaging: 1mg
Price: $63
Updated: 2024/03/01

Cayman Chemical

Product number: 23233
Product name: Isoxanthohumol
Purity: ≥98%
Packaging: 5mg
Price: $245
Updated: 2024/03/01

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ISOXANTHOHUMOL Chemical Properties,Usage,Production

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. 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. Isoxanthohumol reversibly inhibits K_v1.3 channels with an EC₅₀ value of 7.8 μM in human Jurkat T cells using patch clamp electrophysiology. It has strong deterrent properties against the peach potato aphid. It has also been used as a marker of beer consumption. Isoxanthohumol is metabolized in the liver and intestine to 8-prenylnaringenin , a potent phytoestrogen.

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

ISOXANTHOHUMOL Preparation Products And Raw materials

Raw materials

Preparation Products

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521-48-2, ISOXANTHOHUMOLRelated Search:

ISOPIMPINELLIN 2-(3-Methoxy-4-hydroxyphenyl)-6-α-D-glucopyranosyl-5,7-dihydroxy-4H-1-benzopyran-4-one (+/-)-8-PRENYLNARINGENIN ISOXANTHOHUMOL(NEW)(PRIMARY STANDARD) ISOXANTHOHUMOL(NEW)(P) Isoxanthohumol【Helichrysum】

ISOXANTHOHUMOL

4',7-DIHYDROXY-5-METHOXY-8-PRENYLFLAVANONE

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

4',7-Dihydroxy-5-methoxy-8-(3-methyl-2-butenyl)flavanone

4H-1-Benzopyran-4-one, 2,3-dihydro-7-hydroxy-2-(4-hydroxyphenyl)-5-methoxy-8-(3-methyl-2-buten-1-yl)-

Isoxanthohumol, 10 mM in DMSO

(±)-Isoxanthohumol

7-Hydroxy-2-(4-hydroxyphenyl)-5-methoxy-8-(3-methylbut-2-en-1-yl)chroman-4-one

521-48-2