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Genistin

analytical standard

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Synonym(s):
4′,5,7-Trihydroxyisoflavone 7-glucoside, Genistein 7-glucoside, Genistein-7-O-β-D-glucopyranoside, Genistoside, NSC 5112
Empirical Formula (Hill Notation):
C21H20O10
CAS Number:
529-59-9
Molecular Weight:
432.38
Beilstein:
64479
MDL number:
MFCD00016883
UNSPSC Code:
85151701
PubChem Substance ID:
329765260
NACRES:
NA.24

grade

analytical standard

Quality Level

100

Assay

≥98.0% (HPLC)

shelf life

limited shelf life, expiry date on the label

technique(s)

HPLC: suitable
gas chromatography (GC): suitable

application(s)

food and beverages

format

neat

storage temp.

2-8°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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General description

Genistin belongs to the class of isoflavone glycosides generally extracted from soybeans.

Application

Genistin has been used as an analytical reference standard for the analysis of genistin in:
  • Legumes by ultra-high performance liquid chromatography coupled to tandem mass spectrometry (UHPLC-MS/MS) with electrospray ionization (ESI) source and multiple reaction monitoring (MRM) detection.

It may be used as an analytical reference standard for the determination of genistin in:
  • Soy-based foods and dietary supplements by LC coupled to absorbance detection and isotope-dilution mass spectrometry (IDMS), equipped with ESI source and selected ion monitoring (SIM) mode.
  • Soy products by colloidal gold-based indirect competitive immunochromatographic assay (ICA).
  • Rainbow trout muscle by QuEChERS (quick, easy, cheap, effective, rugged and safe) extraction and LC-ESI-MS/MS.
  • Soybean flour by matrix solid phase dispersion extraction (MSPD) and LC with ultraviolet-diode array detection (UV-DAD).
  • Soymilk samples by HPLC-UV operating under the gradient elution mode.

Refer to the product′s Certificate of Analysis for more information on a suitable instrument technique. Contact Technical Service for further support.

Biochem/physiol Actions

Selective inhibitor of mammalian terminal deoxynucleotidyl transferase (TdT), with no measurable effect on mammalian or microbial DNA polymerases.

Packaging

Bottomless glass bottle. Contents are inside inserted fused cone.

WGK

WGK 3

Flash Point(F)

Not applicable

Flash Point(C)

Not applicable

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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  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.

Effective clean-up and ultra high-performance liquid chromatography-tandem mass spectrometry for isoflavone determination in legumes.
Vila-Donat P, et al.
Food Chemistry, 174, 487-494 (2015)
Analysis of water-soluble bioactive compounds in commonly consumed soymilk in China.
Li YR, et al.
J. Food Compos. Anal., 46(4), 29-35 (2016)
Liquid chromatography with absorbance detection and with isotope-dilution mass spectrometry for determination of isoflavones in soy standard reference materials.
Phillips MM, et al.
Analytical and Bioanalytical Chemistry, 409(4), 949-960 (2017)
Colloidal gold-based indirect competitive immunochromatographic assay for rapid detection of bioactive isoflavone glycosides daidzin and genistin in soy products.
Sakamoto S, et al.
Food Chemistry, 194, 191-195 (2016)
Isoflavones quantification in rainbow trout muscle by QuEChERS tecnique and liquid chromatography coupled with mass spectrometry.
Merlanti R, et al.
J. Food Compos. Anal., 70(4), 114-124 (2018)
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