Genistin Chemical Properties

Melting point:

254°C

alpha 

D21 -28° (c = 0.6 in 0.02N NaOH); D26 -21.4° (pyridine)

Boiling point:

256 °C

Density 

1.642±0.06 g/cm3(Predicted)

storage temp. 

2-8°C

solubility 

DMSO: 10 mg/mL

pka

6.12±0.20(Predicted)

form 

Solid

color 

Off-white

biological source

Glycine max (soybean)

Merck 

13,4402

BRN 

64479

Stability:

Stable for 1 year from date of purchase as supplied. Solutions in DMSO may be stored at -20°C for up to 1 week.

InChIKey

ZCOLJUOHXJRHDI-CMWLGVBASA-N

LogP

0.790 (est)

Safety Information

Safety Statements 

22-24/25

WGK Germany 

3

RTECS 

DJ3093000

F 

10

HS Code 

29389090

MSDS

• Language:English Provider:SigmaAldrich

Genistin Usage And Synthesis

Description

Genistin is a natural isoflavone isolated from legumes, including soy and kudzu. It is a phytoestrogen, as it stimulates the growth of estrogen-dependent human breast cancer cells in vivo. Like other isoflavones, genistin promotes the proliferation of bone marrow stromal cells and osteoblasts and suppresses bone turnover. It also increases bone formation in collagen matrix in vivo.

Chemical Properties

White Powder

Uses

A derivative of Genistein. Inhibitor

Uses

An isoflavone glycoside which is an inactive analog of the PTK inhibitor Genistein.

Uses

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

Uses

Glucoside of genistein that inhibits protein tyrosine kinase

Definition

ChEBI: Genistein 7-O-beta-D-glucoside is a 7-hydroxyisoflavones 7-O-beta-D-glucoside. It is functionally related to a genistein. It is a conjugate acid of a genistein 7-O-beta-D-glucoside(1-).

General Description

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

Biochem/physiol Actions

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

Purification Methods

Genistin is repeatedly crystallised from hot 80% EtOH/water and treated with charcoal (Nuchar) until free from saponin. The presence of saponin is detected by adding crystals to conc H2SO4 when the citron yellow colour changes to red, then purple. Pure genistin does not change colour. UV in 85% EtOH has max at 262.5nm. [Walter J Am Chem Soc 63 3273 1941, Beilstein 18 III/IV 2732.]

References

[1] YUKINOBU UCHIYAMA . Selective inhibitors of terminal deoxyribonucleotidyltransferase (TdT): Baicalin and genistin[J]. Biochimica et biophysica acta. General subjects, 2005, 1725 3: Pages 298-304. DOI:10.1016/j.bbagen.2005.06.017
[2] EUN JEONG CHOI  Myeong S L  Taehee Kim. Pro-apoptotic effect and cytotoxicity of genistein and genistin in human ovarian cancer SK-OV-3 cells[J]. Life sciences, 2007, 80 15: Pages 1403-1408. DOI:10.1016/j.lfs.2006.12.031
[3] ALESSANDRA RUSSO . Genistin inhibits UV light-induced plasmid DNA damage and cell growth in human melanoma cells[J]. Journal of Nutritional Biochemistry, 2006, 17 2: Pages 103-108. DOI:10.1016/j.jnutbio.2005.05.011

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