MedKoo Biosciences, Inc.
Tel:   +1-919-636-5577    Fax:   +1-919-980-4831    Email:   sales@medkoo.com
Search
Login Register
Search
MedKoo Cat#: 540154 | Name: Genistin
Featured

Description:

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

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.

Chemical Structure

Genistin
Genistin
CAS#529-59-9

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

Price and Availability

Size Price Availability Quantity
100mg USD 350.00 2 Weeks
200mg USD 550.00 2 Weeks
500mg USD 950.00 2 Weeks
1g USD 1,450.00 2 Weeks
Bulk Inquiry
Buy Now
Add to Cart
Related CAS #
No Data
Synonym
Genistin; Genistine; Genistoside; Genistein glucoside; Genistein 7-glucoside; Glucosyl-7-genistein; NSC 5112; NSC5112; NSC-5112;
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
Appearance
Solid powder
Purity
>97% (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).
HS Tariff Code
2934.99.9001
More Info
Product Data
Product Data
Instruction
View handling instruction
Biological target:
Genistin (Genistine), an isoflavone belonging to the phytoestrogen family, is a potent anti-adipogenic and anti-lipogenic agent. Genistin attenuates cellular growth and promotes apoptotic cell death breast cancer cells through modulation of ERalpha signaling pathway.
In vitro activity:
Genistin and genistein suppress adipocyte-specific proteins and genes, such as peroxisome proliferator-activated receptor γ (PPARγ), CCAAT-enhancer-binding protein α (C/EBPα), and adipocyte binding protein 2 (aP2)/fatty acid-binding protein 4 (FABP4), and lipogenic enzymes such as ATP citrate lyase (ACL), acetyl-CoA carboxylase 1 (ACC1), and fatty acid synthase (FAS). Both isoflavones also activate AMP-activated protein kinase α (AMPKα), an essential factor in adipocyte differentiation, and inhibited sterol regulatory element-binding transcription factor 1c (SREBP-1c). These results indicate that genistin is a potent anti-adipogenic and anti-lipogenic agent. Reference: Molecules. 2020 Apr 27;25(9):2042. https://pubmed.ncbi.nlm.nih.gov/32349444/
In vivo activity:
Furthermore, this study’s results determined that pretreatment with genistin significantly attenuated the cytokines release. As expected, the treatment of genistin dose-dependently protected the rats of I/R injury. In the high dosage group, the levels of inflammatory cytokines were mostly close to the sham rats. Serum IL-6, IL-8, IL-10, and TNF-α concentrations decreased 21.3%, 36.9%, 28.1%, and 44.4%, respectively. Reference: Evid Based Complement Alternat Med. 2016;2016:5381290. https://pubmed.ncbi.nlm.nih.gov/27087823/
Solvent mg/mL mM
Solubility
DMF 16.0 37.00
DMF:PBS (pH 7.2) (1:1) 0.5 1.16
DMSO 66.2 153.03
Note: There can be variations in solubility for the same chemical from different vendors or different batches from the same vendor. The following factors can affect the solubility of the same chemical: solvent used for crystallization, residual solvent content, polymorphism, salt versus free form, degree of hydration, solvent temperature. Please use the solubility data as a reference only. Warming and sonication will facilitate dissolving. Still have questions? Please contact our Technical Support scientists.

Preparing Stock Solutions

The following data is based on the product molecular weight 432.38 Batch specific molecular weights may vary from batch to batch due to the degree of hydration, which will affect the solvent volumes required to prepare stock solutions.

Recalculate based on batch purity %
Concentration / Solvent Volume / Mass 1 mg 5 mg 10 mg
1 mM 1.15 mL 5.76 mL 11.51 mL
5 mM 0.23 mL 1.15 mL 2.3 mL
10 mM 0.12 mL 0.58 mL 1.15 mL
50 mM 0.02 mL 0.12 mL 0.23 mL
Formulation protocol:
1. Choi YR, Shim J, Kim MJ. Genistin: A Novel Potent Anti-Adipogenic and Anti-Lipogenic Agent. Molecules. 2020 Apr 27;25(9):2042. doi: 10.3390/molecules25092042. PMID: 32349444; PMCID: PMC7248826. 2. 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. PMID: 27087823; PMCID: PMC4818796.
In vitro protocol:
1. Choi YR, Shim J, Kim MJ. Genistin: A Novel Potent Anti-Adipogenic and Anti-Lipogenic Agent. Molecules. 2020 Apr 27;25(9):2042. doi: 10.3390/molecules25092042. PMID: 32349444; PMCID: PMC7248826.
In vivo protocol:
1. 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. PMID: 27087823; PMCID: PMC4818796.
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.