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Merck
CN

G0897

Genistin

From Glycine max (soybean), ≥95% (HPLC), terminal deoxynucleotidyl transferase (TdT) inhibitor

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:
Molecular Weight:
432.38
Beilstein:
64479
MDL number:
UNSPSC Code:
12352200
PubChem Substance ID:
NACRES:
NA.77
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Product Name

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

biological source

Glycine max (soybean)

Quality Level

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

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Certificates of Analysis (COA)

Lot/Batch Number

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  1. Which document(s) contains shelf-life or expiration date information for a given product?

    If available for a given product, the recommended re-test date or the expiration date can be found on the Certificate of Analysis.

  2. How do I get lot-specific information or a Certificate of Analysis?

    The lot specific COA document can be found by entering the lot number above under the "Documents" section.

  3. How do I find price and availability?

    There are several ways to find pricing and availability for our products. Once you log onto our website, you will find the price and availability displayed on the product detail page. You can contact any of our Customer Sales and Service offices to receive a quote.  USA customers:  1-800-325-3010 or view local office numbers.

  4. What is the Department of Transportation shipping information for this product?

    Transportation information can be found in Section 14 of the product's (M)SDS.To access the shipping information for this material, use the link on the product detail page for the product. 

  5. What is the lambda max for genistin and what is the molar extinction coefficient at that wavelength?

    We have data from our QC labs here at Sigma on one of the Genistin products we offer, G0897. The solvent is 85% ethanol/15% water, and the lambda max is typically 262.0 or 262.5 nm. We measured the molar extinction coefficients at the lambda max for four different lots of G0897 back in the 1990s, and the average value was 39,800 M-1.Genistin is a derivative of Genistein. There is an entry for Genistein in the chemicals encyclopedia published by the Royal Society of Chemistry, with information for Genistin under that heading.According to the chemicals encyclopedia published by the Royal Society of Chemistry, 14th edition, entry #4391, "uv max (85% ethanol) 262.5 nm (a 90.5)".The value of ""a 90.5"" is the same as an E0.1%, or the extinction coefficient for a 1 mg/mL (or 1 gram per Liter) solution.If one multiplies 90.5 (L/g) by the molecular weight of genistin (432.38 g/mole), you get 39,130 M-1. This is pretty close to the value of 39,800 from our data above.

  6. My question is not addressed here, how can I contact Technical Service for assistance?

    Ask a Scientist here.

T Hamakawa et al.
The Journal of neuroscience : the official journal of the Society for Neuroscience, 19(21), 9306-9312 (1999-10-26)
Neurotrophic factors have well established roles in neuronal development and adult synaptic plasticity, but their precise role in synapse formation has yet to be determined. This paper provides the first direct evidence that neurotrophic factors in brain conditioned medium (CM)
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)
Soha M Hamdy et al.
Toxicology and industrial health, 28(8), 746-757 (2011-11-18)
Breast cancer is the second leading cause of cancer death among women and the third most common cancer. In this study, we investigated the chemoprevention efficacy of each of soy genistin, selenium or a combination of them against breast cancer.
Anna Hsu et al.
Experimental biology and medicine (Maywood, N.J.), 235(1), 90-97 (2010-04-21)
Previous studies have suggested that soy isoflavones exert anticarcinogenic effects against prostate cancer. We propose that soy extracts, containing a mixture of soy isoflavones and other bioactive components, would be a more potent chemo-preventive agent than individual soy isoflavones. We
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

Articles

Serotonin is stored in cells and metabolized by MAO, influencing CNS, GI, and platelet functions.

血清素(5-羟色胺)主要存在于三种主要细胞类型中:i)中杻神经系统(CNS)和肠肌间神经丛中的血清素能神经元,ii)胃肠道粘膜中的肠嗜铬细胞,和iii)血小板。血清素的代谢主要通过外部线粒体膜酶单胺氧化酶(MAO)进行,它以两种分子亚型存在,分别称为MAO-A和MAO-B。

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