Genistin
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    WARNING: This product is for research use only, not for human or veterinary use.

MedKoo CAT#: 540154

CAS#: 529-59-9

Description: Genistin is a selective estrogen receptor modulator (SERM) found in soy. It is the less active glycoside analog of genistein. It acts as a phytoestrogen, induces cell cycle arrest and apoptosis in ovarian cancer cells, improves bone density and strength, and decreases myosin light chain kinase levels.


Price and Availability

Size
Price

500mg
USD 450
5g
USD 2450
Size
Price

1g
USD 650
Size
Price

2g
USD 1050

Genistin, purity > 98%, is in stock. Current shipping out time is about 2 weeks after order is received. CoA, QC data and MSDS documents are available in one week after order is received.


Chemical Structure

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Theoretical Analysis

MedKoo Cat#: 540154
Name: Genistin
CAS#: 529-59-9
Chemical Formula: C21H20O10
Exact Mass: 432.1056
Molecular Weight: 432.38
Elemental Analysis: C, 58.34; H, 4.66; O, 37.00


Synonym: Genistein glucoside; CS-4240; CS 4240;CS4240; NSC 5112; NSC5112; NSC-5112; Genistin

IUPAC/Chemical Name: 5-hydroxy-3-(4-hydroxyphenyl)-7-(((2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)tetrahydro-2H-pyran-2-yl)oxy)-4H-chromen-4-one

InChi Key: ZCOLJUOHXJRHDI-CMWLGVBASA-N

InChi Code: 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

SMILES Code: O=C1C(C2=CC=C(O)C=C2)=COC3=C1C(O)=CC(O[C@@H]4O[C@H](CO)[C@@H](O)[C@H](O)[C@H]4O)=C3


Technical Data

Appearance:
Solid powder

Purity:
>98% (or refer to the Certificate of Analysis)

Shipping Condition:
Shipped under ambient temperature as non-hazardous chemical. This product is stable enough for a few weeks during ordinary shipping and time spent in Customs.

Storage Condition:
Dry, dark and at 0 - 4 C for short term (days to weeks) or -20 C for long term (months to years).

Solubility:
Soluble in DMSO

Shelf Life:
>2 years if stored properly

Drug Formulation:
This drug may be formulated in DMSO

Stock Solution Storage:
0 - 4 C for short term (days to weeks), or -20 C for long term (months).

Harmonized System Code:
293490


References

1: Xiong YJ, Chen DP, Lv BC, Liu FF, Wang L, Lin Y. The characteristics of genistin-induced inhibitory effects on intestinal motility. Arch Pharm Res. 2013 Mar;36(3):345-52. doi: 10.1007/s12272-013-0053-2. Epub 2013 Feb 23. PubMed PMID: 23435915.

2: Hamdy SM, Latif AK, Drees EA, Soliman SM. Prevention of rat breast cancer by genistin and selenium. Toxicol Ind Health. 2012 Sep;28(8):746-57. doi: 10.1177/0748233711422732. Epub 2011 Nov 16. PubMed PMID: 22089659.

3: Gu M, Zheng AB, Jin J, Cui Y, Zhang N, Che ZP, Wang Y, Zhan J, Tu WJ. Cardioprotective Effects of Genistin in Rat Myocardial Ischemia-Reperfusion Injury Studies by Regulation of P2X7/NF-κB Pathway. Evid Based Complement Alternat Med. 2016;2016:5381290. doi: 10.1155/2016/5381290. Epub 2016 Mar 20. PubMed PMID: 27087823; PubMed Central PMCID: PMC4818796.

4: Sakamoto S, Yusakul G, Pongkitwitoon B, Paudel MK, Tanaka H, Morimoto S. Simultaneous determination of soy isoflavone glycosides, daidzin and genistin by monoclonal antibody-based highly sensitive indirect competitive enzyme-linked immunosorbent assay. Food Chem. 2015 Feb 15;169:127-33. doi: 10.1016/j.foodchem.2014.08.004. Epub 2014 Aug 9. PubMed PMID: 25236207.

5: Wong RW, Rabie AB. Effect of genistin on bone formation. Front Biosci (Elite Ed). 2010 Jan 1;2:764-70. PubMed PMID: 20036920.

6: Cao J, Echelberger R, Liu M, Sluzas E, McCaffrey K, Buckley B, Patisaul HB. Soy but not bisphenol A (BPA) or the phytoestrogen genistin alters developmental weight gain and food intake in pregnant rats and their offspring. Reprod Toxicol. 2015 Dec;58:282-94. doi: 10.1016/j.reprotox.2015.07.077. Epub 2015 Jul 26. PubMed PMID: 26216788; PubMed Central PMCID: PMC4690759.

7: Hooshmand S, Juma S, Arjmandi BH. Combination of genistin and fructooligosaccharides prevents bone loss in ovarian hormone deficiency. J Med Food. 2010 Apr;13(2):320-5. doi: 10.1089/jmf.2009.0059. PubMed PMID: 20132047.

8: Fahmi R, Khodaiyan F, Pourahmad R, Emam-Djomeh Z. Effect of ultrasound assisted extraction upon the Genistin and Daidzin contents of resultant soymilk. J Food Sci Technol. 2014 Oct;51(10):2857-61. doi: 10.1007/s13197-012-0744-6. Epub 2012 Jun 9. PubMed PMID: 25328238; PubMed Central PMCID: PMC4190193.

9: Park CU, Jeong MK, Park MH, Yeu J, Park MS, Kim MJ, Ahn SM, Chang PS, Lee J. Formation of succinyl genistin and succinyl daidzin by Bacillus species. J Food Sci. 2010 Jan-Feb;75(1):C128-33. doi: 10.1111/j.1750-3841.2009.01453.x. Erratum in: J Food Sci. 2010 Apr;75(3):viii. PubMed PMID: 20492143.

10: You J, Jiang D. [Effect of genistin on proliferative vitreoretinopathy]. Zhong Nan Da Xue Xue Bao Yi Xue Ban. 2010 Jul;35(7):749-53. doi: 10.3969/j.issn.1672-7347.2010.07.017. Chinese. PubMed PMID: 20693719.

11: Park DJ, Lee YS, Choi YL. Characterization of a cold-active β-glucosidase from Paenibacillus xylanilyticus KJ-03 capable of hydrolyzing isoflavones daidzin and genistin. Protein J. 2013 Oct;32(7):579-84. doi: 10.1007/s10930-013-9520-3. PubMed PMID: 24141566.

12: Xu Z, Wu Q, Godber JS. Stabilities of daidzin, glycitin, genistin, and generation of derivatives during heating. J Agric Food Chem. 2002 Dec 4;50(25):7402-6. PubMed PMID: 12452666.

13: Andlauer W, Kolb J, Fürst P. Phloridzin improves absorption of genistin in isolated rat small intestine. Clin Nutr. 2004 Oct;23(5):989-95. PubMed PMID: 15380887.

14: Sakamoto S, Yusakul G, Pongkitwitoon B, Tanaka H, Morimoto S. Colloidal gold-based indirect competitive immunochromatographic assay for rapid detection of bioactive isoflavone glycosides daidzin and genistin in soy products. Food Chem. 2016 Mar 1;194:191-5. doi: 10.1016/j.foodchem.2015.08.002. Epub 2015 Aug 4. PubMed PMID: 26471543.

15: Chung MJ, Kang AY, Lee KM, Oh E, Jun HJ, Kim SY, Auh JH, Moon TW, Lee SJ, Park KH. Water-soluble genistin glycoside isoflavones up-regulate antioxidant metallothionein expression and scavenge free radicals. J Agric Food Chem. 2006 May 31;54(11):3819-26. PubMed PMID: 16719502.

16: Yamaguchi M, Gao YH. Anabolic effect of genistein and genistin on bone metabolism in the femoral-metaphyseal tissues of elderly rats: the genistein effect is enhanced by zinc. Mol Cell Biochem. 1998 Jan;178(1-2):377-82. PubMed PMID: 9546622.

17: Zou P, Xing L, Tang Q, Liu R, Hao W. Comparative evaluation of the teratogenicity of genistein and genistin using rat whole embryo culture and limbud micromass culture methods. Food Chem Toxicol. 2012 Aug;50(8):2831-6. doi: 10.1016/j.fct.2012.05.009. Epub 2012 May 14. PubMed PMID: 22617716.

18: Andlauer W, Kolb J, Fürst P. Absorption and metabolism of genistin in the isolated rat small intestine. FEBS Lett. 2000 Jun 16;475(2):127-30. PubMed PMID: 10858502.

19: Chiang CM, Wang DS, Chang TS. Improving Free Radical Scavenging Activity of Soy Isoflavone Glycosides Daidzin and Genistin by 3'-Hydroxylation Using Recombinant Escherichia coli. Molecules. 2016 Dec 15;21(12). pii: E1723. PubMed PMID: 27983702.

20: Yuan B, Zhen H, Jin Y, Xu L, Jiang X, Sun S, Li C, Xu H. Absorption and plasma disposition of genistin differ from those of genistein in healthy women. J Agric Food Chem. 2012 Feb 15;60(6):1428-36. doi: 10.1021/jf204421c. Epub 2012 Feb 3. PubMed PMID: 22256777.