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Genistein information


Genistein
Genistein molecule
Names
IUPAC name
4′,5,7-Trihydroxyisoflavone
Systematic IUPAC name
5,7-Dihydroxy-3-(4-hydroxyphenyl)-4H-1-benzopyran-4-one
Identifiers
CAS Number
  • 446-72-0 checkY
3D model (JSmol)
  • Interactive image
Beilstein Reference
263823
ChEBI
  • CHEBI:28088 checkY
ChEMBL
  • ChEMBL44 checkY
ChemSpider
  • 4444448 checkY
DrugBank
  • DB01645 checkY
ECHA InfoCard 100.006.524 Edit this at Wikidata
EC Number
  • 207-174-9
IUPHAR/BPS
  • 2826
KEGG
  • D11680 checkY
  • C06563
PubChem CID
  • 5280961
UNII
  • DH2M523P0H checkY
CompTox Dashboard (EPA)
  • DTXSID5022308 Edit this at Wikidata
InChI
  • InChI=1S/C15H10O5/c16-9-3-1-8(2-4-9)11-7-20-13-6-10(17)5-12(18)14(13)15(11)19/h1-7,16-18H checkY
    Key: TZBJGXHYKVUXJN-UHFFFAOYSA-N checkY
  • InChI=1/C15H10O5/c16-9-3-1-8(2-4-9)11-7-20-13-6-10(17)5-12(18)14(13)15(11)19/h1-7,16-18H
    Key: TZBJGXHYKVUXJN-UHFFFAOYAH
SMILES
  • Oc1ccc(cc1)C\3=C\Oc2cc(O)cc(O)c2C/3=O
Properties
Chemical formula
C15H10O5
Molar mass 270.240 g·mol−1
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
checkY verify (what is checkY☒N ?)
Infobox references

Genistein (C15H10O5) is a naturally occurring compound that structurally belongs to a class of compounds known as isoflavones. It is described as an angiogenesis inhibitor and a phytoestrogen.[1]

It was first isolated in 1899 from the dyer's broom, Genista tinctoria; hence, the chemical name. The compound structure was established in 1926, when it was found to be identical with that of prunetol. It was chemically synthesized in 1928.[2] It has been shown to be the primary secondary metabolite of the Trifolium species and Glycine max.[3]

  1. ^ Sail, Vibhavari; Hadden, M. Kyle (2012-01-01), Desai, Manoj C. (ed.), Chapter Eighteen - Notch Pathway Modulators as Anticancer Chemotherapeutics, Annual Reports in Medicinal Chemistry, vol. 47, Academic Press, pp. 267–280, doi:10.1016/B978-0-12-396492-2.00018-7, retrieved 2020-09-14
  2. ^ Walter, E. D. (1941). "Genistin (an Isoflavone Glucoside) and its Aglucone, Genistein, from Soybeans". Journal of the American Chemical Society. 63 (12): 3273–76. doi:10.1021/ja01857a013.
  3. ^ Popiołkiewicz, Joanna; Polkowski, Krzysztof; Skierski, Janusz S.; Mazurek, Aleksander P. (November 2005). "In vitro toxicity evaluation in the development of new anticancer drugs—genistein glycosides". Cancer Letters. 229 (1): 67–75. doi:10.1016/j.canlet.2005.01.014. ISSN 0304-3835. PMID 16157220.

and 25 Related for: Genistein information

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Genistein

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Genistein (C15H10O5) is a naturally occurring compound that structurally belongs to a class of compounds known as isoflavones. It is described as an angiogenesis...

Word Count : 4437

Genistin

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to its aglycone form, genistein. It is hydrolyzed by removing the covalently bound glucose to form genistein and that genistein is the form of the compound...

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Mixed inhibition

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known to be regulated by Genistein, an isoflavone that is naturally found in a number of plants. It was first proven that genistein inhibits the activity...

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Isoflavone

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source of isoflavones in human food; the major isoflavones in soybean are genistein and daidzein. The phenylpropanoid pathway begins from the amino acid phenylalanine...

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Styphnolobium japonicum

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aglycones genistein, quercetin and kaempferol. Another analysis found genistein and genistein glycosides including sophorabioside, sophoricoside, genistein-7-diglucoside...

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Sanfilippo syndrome

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disease may be alleviated by an adequate dose of genistein. Despite its reported beneficial properties, genistein also has toxic side effects. Several support...

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Phytoestrogen

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differential effects in a dose-dependent way. The final biological effects of genistein are determined by the balance among these pleiotrophic actions. Phytoestrogens...

Word Count : 3866

Daidzein

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low water solubility. Daidzein and other isoflavone compounds, such as genistein, are present in a number of plants and herbs like kwao krua (Pueraria...

Word Count : 1054

Sophoricoside

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Sophoricoside is an isoflavone Genistein glycoside found in the dried ripe fruit of Styphnolobium japonicum (L.) Schott, a herb used in traditional Chinese...

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Genista tinctoria

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also provides a green colour. It was from this plant that the isoflavone genistein was first isolated in 1899; hence the name of the chemical compound. The...

Word Count : 360

Apios americana

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A. carnea and A. fortunei. However, A. americana had larger levels of genistein than the other two species. The fatty acid content of tubers is approximately...

Word Count : 3761

Pueraria mirifica

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phytoestrogens including deoxymiroestrol, daidzin, daidzein, genistin, genistein, coumestrol, kwakhurin, and mirificine, β-sitosterol, stigmasterol, campesterol...

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Thyroid peroxidase

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and methimazole. In laboratory rats with insufficient iodine intake, genistein has demonstrated inhibition of TPO. Thyroid peroxidase is a frequent epitope...

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Soybean meal

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Most studies of phytoestrogens in soy have identified the isoflavones genistein and daidzein as its principal phytoestrogenic substances. For several...

Word Count : 1148

Isoflavonoid

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backbone (case of isoflavanes, such as equol). Daidzein Equol Flavonoid Genistein Glycitein Homoisoflavonoids, related molecules with a 16-carbon skeleton...

Word Count : 242

Biochanin A

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Other names Biochanin 4′-Methylgenistein olmelin Biochanine A Biochanin-A Genistein 4-methyl ether Identifiers CAS Number 491-80-5 Y 3D model (JSmol) Interactive...

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Paracetamol

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4-Nonylphenylboronic acid AACOCF3 AM-404 Arachidonoyl serotonin BIA 10-2474 Biochanin A Genistein IDFP JNJ-1661010 JNJ-42165279 JZL-195 Kaempferol LY-2183240 MAFP Palmitoylisopropylamide...

Word Count : 12173

Prunus maximowiczii

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and prunasin, the derivatives of which produce prussic acid as well as Genistein can be extracted from P. maximowiczii.  Prunus maximowiczii was originally...

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C21H20O10

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number 68592-14-3) Genistein 5-O-glucoside (CAS number 128508-06-5) Genistein 8-C-glucoside (CAS number 66026-80-0) Genistin (Genistein 7-glucoside, CAS...

Word Count : 391

Caffeine

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Dihydropyridines (e.g., nicardipine, nifedipine, nitrendipine) Furosemide Genistein Ginkgo constituents (e.g., bilobalide, ginkgolides (e.g., ginkgolide A...

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Flemingia vestita

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during August and September. It is rich in bioactive isoflavones such as genistein, daidzein, formononetin and pseudobaptigenin. This juicy tuber is a highly...

Word Count : 902

Edamame

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Phytoestrogens Genistein Genistin Glycitein Glycitin Ononin Daidzein Equol (metabolite) O-DMA (metabolite) Daidzin (leaves) Globulins (proteins) Beta-conglycinin...

Word Count : 1386

Miso soup

Last Update:

Phytoestrogens Genistein Genistin Glycitein Glycitin Ononin Daidzein Equol (metabolite) O-DMA (metabolite) Daidzin (leaves) Globulins (proteins) Beta-conglycinin...

Word Count : 1524

Nitrous oxide

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Dihydropyridines (e.g., nicardipine, nifedipine, nitrendipine) Furosemide Genistein Ginkgo constituents (e.g., bilobalide, ginkgolides (e.g., ginkgolide A...

Word Count : 10073

Nicotinamide

Last Update:

daidzin, ECG, EGCG, epicatechin, equol, formononetin, glabrene, glabridin, genistein, genistin, glycitein, kaempferol, liquiritigenin, mirificin, myricetin...

Word Count : 2425

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