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G0897

Sigma-Aldrich

Genistin

from Glycine max (soybean), ≥95% (HPLC)

Synonym(s):

4′,5,7-Trihydroxyisoflavone 7-glucoside, Genistein 7-glucoside, Genistein-7-O-β-D-glucopyranoside, Genistoside, NSC 5112

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About This Item

Empirical Formula (Hill Notation):
C21H20O10
CAS Number:
529-59-9
Molecular Weight:
432.38
Beilstein:
64479
MDL number:
MFCD00016883
UNSPSC Code:
12352200
PubChem Substance ID:
24895028
NACRES:
NA.77

biological source

Glycine max (soybean)

Quality Level

200

Assay

≥95% (HPLC)

solubility

DMSO: 10 mg/mL

storage temp.

−20°C

SMILES string

OC[C@H]1O[C@@H](Oc2cc(O)c3C(=O)C(=COc3c2)c4ccc(O)cc4)[C@H](O)[C@@H](O)[C@@H]1O

InChI

1S/C21H20O10/c22-7-15-18(26)19(27)20(28)21(31-15)30-11-5-13(24)16-14(6-11)29-8-12(17(16)25)9-1-3-10(23)4-2-9/h1-6,8,15,18-24,26-28H,7H2/t15-,18-,19+,20-,21-/m1/s1

InChI key

ZCOLJUOHXJRHDI-CMWLGVBASA-N

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Application

Genistin has been used for immune reactivity against influenza viruses in vitro and as an internal standard in isoflavones quantification.

Biochem/physiol Actions

Inactive analog of genistein; useful as a negative control for genistein and other tyrosine kinase inhibitors.
Selective inhibitor of mammalian terminal deoxynucleotidyl transferase (TdT), with no measurable effect on mammalian or microbial DNA polymerases.

Features and Benefits

This compound is featured on the Dopamine and Norepinephrine Metabolism and Histamine Synthesis and Metabolism pages of the Handbook of Receptor Classification and Signal Transduction. To browse other handbook pages, click here.

Storage Class Code

11 - Combustible Solids

WGK

WGK 3

Flash Point(F)

Not applicable

Flash Point(C)

Not applicable

Personal Protective Equipment

dust mask type N95 (US), Eyeshields, Gloves

Certificates of Analysis (COA)

Search for Certificates of Analysis (COA) by entering the products Lot/Batch Number. Lot and Batch Numbers can be found on a product’s label following the words ‘Lot’ or ‘Batch’.

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Genistein, Soybean A cell-permeable, reversible, substrate competitive inhibitor of protein tyrosine kinases, including autophosphorylation of epidermal growth factor receptor kinase (IC₅₀ = 2.6 µM).

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345834

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Soy saponins meditate the progression of colon cancer in rats by inhibiting the activity of beta-glucuronidase and the number of aberrant crypt foci but not cyclooxygenase-2 activity.
Guo YW, et al.
ISRN Oncology, 2013 (2013)
Bo Yuan et al.
Journal of agricultural and food chemistry, 60(6), 1428-1436 (2012-01-20)
The chemical forms in which isoflavones appear in food or supplements seem to play an important role in their absorption efficiency. However, the influence of the chemical form of isoflavones on their plasma disposition has never been reported, although the
Amélia P Rauter et al.
Phytotherapy research : PTR, 24 Suppl 2, S133-S138 (2010-03-24)
The antihyperglycaemic effect of eight standard flavonoids, previously identified in the ethanol extract of the claimed antidiabetic plant Genista tenera, was evaluated on streptozotocin (STZ)-induced diabetic Wistar rats. The aglycones apigenin, chrysoeriol and genistein, the monoglucosides apigenin 7-O-glucoside, luteolin 7-O-glucoside
Bishnu Prasad Pandey et al.
Enzyme and microbial technology, 48(4-5), 386-392 (2011-11-25)
Screening of cytochrome P450 monoxygenases responsible for the regiospecific hydroxylation of flavones, isoflavones and chalcones was attempted using a P450 library constructed from Streptomyces avermitilis MA4680, Bacillus and Nocardia farcinica IFM10152 strains. As electron transfer redox partners with the P450s
A C M Boon et al.
Scandinavian journal of immunology, 55(1), 24-32 (2002-02-14)
In vitro studies have demonstrated positive effects of bioactive compounds on several functions of the immune system. In the present study, 25 of such compounds were tested for their immune modulating properties on influenza virus specific human B- and T-cell
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