(±)-Isoxanthohumol
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| Category | Bioactive by-products |
| Catalog number | BBF-04188 |
| CAS | 521-48-2 |
| Molecular Weight | 354.40 |
| Molecular Formula | C21H22O5 |
| Purity | 96% |
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Description
It is one of many bioactive prenylflavonoids that can be isolated from the hops plant or humulus lupulus L. It has apparent chemotherapeutic prevention activity. It has also shown notable antiviral, antibacterial and antifungal activity.
Specification
| Related CAS | 115116-00-2 (Deleted CAS) 70872-29-6 (S-isomer) |
| Synonyms | 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; 5-Methylsophoraflavanone B; 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, 2,3-dihydro-7-hydroxy-2-(4-hydroxyphenyl)-5-methoxy-8-(3-methyl-2-butenyl)-; Flavanone, 4',7-dihydroxy-5-methoxy-8-(3-methyl-2-butenyl)-; Isoxanthohumol |
| Storage | Store at 2-8°C |
| IUPAC Name | 7-hydroxy-2-(4-hydroxyphenyl)-5-methoxy-8-(3-methylbut-2-enyl)-2,3-dihydrochromen-4-one |
| Canonical SMILES | CC(=CCC1=C2C(=C(C=C1O)OC)C(=O)CC(O2)C3=CC=C(C=C3)O)C |
| 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 |
| InChI Key | YKGCBLWILMDSAV-UHFFFAOYSA-N |
Properties
| Appearance | Pale Yellow Solid |
| Antibiotic Activity Spectrum | Fungi; Viruses |
| Boiling Point | 585.8±50.0°C (Predicted) |
| Melting Point | 183-187°C |
| Density | 1.245±0.06 g/cm3 (Predicted) |
| Solubility | Soluble in DMSO (Slightly), Methanol (Slightly) |
Reference Reading
1. Biotransformation of a major beer prenylflavonoid - isoxanthohumol
Jarosław Popłoński, Tomasz Tronina, Agnieszka Bartmańska Z Naturforsch C J Biosci . 2018 Dec 19;74(1-2):1-7. doi: 10.1515/znc-2018-0101.
Microbial transformations of isoxanthohumol (1), a beer prenylated flavonoid, by 51 fungi were investigated. Many of the tested fungi cultures were capable of effective transformation of 1. Mucor hiemalis and Fusarium oxysporum converted isoxanthohumol (1) into isoxanthohumol 7-O-β-d-glucopyranoside (3) and (2R)-2″-(2″'-hydroxyisopropyl)-dihydrofurano[2″,3″:7,8]-4″,5-hydroxy-5-methoxyflavanone (4), respectively. No product was obtained in the transformation of 1 by Absidia glauca conducted in a phosphate buffer. In the same medium, Beauveria bassiana converted isoxanthohumol (1) to isoxanthohumol 7-O-β-d-4″'-O-methylglucopyranoside (2).
2. Exploration of isoxanthohumol bioconversion from spent hops into 8-prenylnaringenin using resting cells of Eubacterium limosum
Anita Van Landschoot, Willy Verstraete, Sam Possemiers, Tom Van de Wiele, Selin Bolca, Jan L Goeman, Esther Moens AMB Express . 2020 Apr 24;10(1):79. doi: 10.1186/s13568-020-01015-5.
Hops is an almost unique source of the potent phytoestrogen 8-prenylnaringenin (8-PN). As hops contain only low levels of 8-PN, synthesis may be more attractive than extraction. A strain of the Gram-positive Eubacterium limosum was isolated previously for 8-PN production from more abundant precursor isoxanthohumol (IX) from hops. In this study, spent hops, an industrial side stream from the beer industry, was identified as interesting source of IX. Yet, hop-derived compounds are well-known antibacterial agents and the traces of a large variety of different compounds in spent hops interfered with growth and IX conversion. Critical factors to finally enable bacterial 8-PN production from spent hops, using a food and feed grade medium, were evaluated in this research. The use of bacterial resting cells and complex medium at a pH of 7.8-8 best fulfilled the requirements for 8-PN production and generated a solid basis for development of an economic process.
3. Isoxanthohumol, a hop-derived flavonoid, alters the metabolomics profile of mouse feces
Shiho Fujisaka, Yuji Nonaka, Kazuyuki Tobe, Shinya Fukizawa, Norihito Murayama, Mai Yamashita Biosci Microbiota Food Health . 2020;39(3):100-108. doi: 10.12938/bmfh.2019-045.
The aim of this study was to verify the effect of treatment with isoxanthohumol (IX) on the metabolomics profile of mouse feces to explore the host-intestinal bacterial interactions at the molecular level. The fecal contents of several amino acids in the high-fat diet (HFD) + 0.1% IX group (treated with IX mixed in diets for 12 weeks) were significantly lower than in the HFD group. The fecal contents of the secondary bile acid deoxycholic acid (DCA) in the HFD + 180 mg/kg IX group (orally treated with IX for 8 weeks) were significantly lower than in the HFD group; the values in the HFD group were higher than those in the normal diet (ND) group. Administration of IX changed the fecal metabolomics profile. For some metabolites, IX normalized HFD-induced fluctuations.
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Bio Calculators
* Our calculator is based on the following equation:
Concentration (start) x Volume (start) = Concentration (final) x Volume (final)
It is commonly abbreviated as: C1V1 = C2V2
* Total Molecular Weight:
g/mol
Tip: Chemical formula is case sensitive. C22H30N4O √ c22h30n40 ╳
