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MedKoo Cat#: 540183 | Name: Glycitein
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Description:

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

Glycitein is found in soy and red clover. It exhibits a variety of biological activities, including increasing Nrf2-related antioxidative signaling, preventing invasion in glioma cells destabilizing amyloid-β aggregates and preventing fibril assembly, and inhibiting osteoclast generation.

Chemical Structure

Glycitein
Glycitein
CAS#40957-83-3

Theoretical Analysis

MedKoo Cat#: 540183

Name: Glycitein

CAS#: 40957-83-3

Chemical Formula: C16H12O5

Exact Mass: 284.0685

Molecular Weight: 284.27

Elemental Analysis: C, 67.60; H, 4.26; O, 28.14

Price and Availability

Size Price Availability Quantity
10mg USD 285.00 2 Weeks
25mg USD 550.00 2 Weeks
50mg USD 850.00 2 Weeks
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Related CAS #
No Data
Synonym
Glycitein; Q-100465; Q100465; Q 100465
IUPAC/Chemical Name
7-hydroxy-3-(4-hydroxyphenyl)-6-methoxy-4H-chromen-4-one
InChi Key
DXYUAIFZCFRPTH-UHFFFAOYSA-N
InChi Code
InChI=1S/C16H12O5/c1-20-15-6-11-14(7-13(15)18)21-8-12(16(11)19)9-2-4-10(17)5-3-9/h2-8,17-18H,1H3
SMILES Code
O=C1C(C2=CC=C(O)C=C2)=COC3=CC(O)=C(OC)C=C13
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).
HS Tariff Code
2934.99.9001
More Info
Product Data
Product Data
Instruction
View handling instruction
Biological target:
Glycitein is a soybean (yellow cultivar) isoflavonoid; used in combination with other isoflavonoids such as genistein and daidzein to study apoptosis and anti-oxidation processes.
In vitro activity:
The apoptotic SK-N-SH cell per-centage was 21% relative at 100 nM dosage of rotenone. Glycitein at 5 μM treatment reduced the rotenone-induced apoptosis to 13%. At 10 μM dosage of the glycitein, the apoptosis decreased to 5.7% (Fig. 6A). The western blot analysis showed that glycitein treatment caused a decrease in a rotenone triggered upregulation of Bax and caspase-3 expression (Fig. 6B). Reference: Acta Biochim Pol. 2022 Jun 12;69(2):447-452. https://pubmed.ncbi.nlm.nih.gov/35691030/
In vivo activity:
Figure 2A demonstrates that the levels of ROS in the C. elegans CL2006 fed with glycitein for 36 h were reduced (control 100 ± 23%, glycitein 68.9 ± 7 %, n = 3, p = 0.05). These results suggest the decreased Aβ toxicity by glycitein might be, in part, a consequence of its antioxidative action. Reference: BMC Neurosci. 2005 Aug 25;6:54. https://pubmed.ncbi.nlm.nih.gov/16122394/
Solvent mg/mL mM
Solubility
DMSO 27.2 95.57
DMF 0.5 1.76
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 284.27 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. Dong N, Yang Z. Glycitein exerts neuroprotective effects in Rotenone-triggered oxidative stress and apoptotic cell death in the cellular model of Parkinson's disease. Acta Biochim Pol. 2022 Jun 12;69(2):447-452. doi: 10.18388/abp.2020_5963. PMID: 35691030. 2. Zhang B, Su JP, Bai Y, Li J, Liu YH. Inhibitory effects of O-methylated isoflavone glycitein on human breast cancer SKBR-3 cells. Int J Clin Exp Pathol. 2015 Jul 1;8(7):7809-17. PMID: 26339345; PMCID: PMC4555673. 3. Gutierrez-Zepeda A, Santell R, Wu Z, Brown M, Wu Y, Khan I, Link CD, Zhao B, Luo Y. Soy isoflavone glycitein protects against beta amyloid-induced toxicity and oxidative stress in transgenic Caenorhabditis elegans. BMC Neurosci. 2005 Aug 25;6:54. doi: 10.1186/1471-2202-6-54. PMID: 16122394; PMCID: PMC1215487. 4. Pan W, Ikeda K, Takebe M, Yamori Y. Genistein, daidzein and glycitein inhibit growth and DNA synthesis of aortic smooth muscle cells from stroke-prone spontaneously hypertensive rats. J Nutr. 2001 Apr;131(4):1154-8. doi: 10.1093/jn/131.4.1154. PMID: 11285318.
In vitro protocol:
1. Dong N, Yang Z. Glycitein exerts neuroprotective effects in Rotenone-triggered oxidative stress and apoptotic cell death in the cellular model of Parkinson's disease. Acta Biochim Pol. 2022 Jun 12;69(2):447-452. doi: 10.18388/abp.2020_5963. PMID: 35691030. 2. Zhang B, Su JP, Bai Y, Li J, Liu YH. Inhibitory effects of O-methylated isoflavone glycitein on human breast cancer SKBR-3 cells. Int J Clin Exp Pathol. 2015 Jul 1;8(7):7809-17. PMID: 26339345; PMCID: PMC4555673.
In vivo protocol:
1. Gutierrez-Zepeda A, Santell R, Wu Z, Brown M, Wu Y, Khan I, Link CD, Zhao B, Luo Y. Soy isoflavone glycitein protects against beta amyloid-induced toxicity and oxidative stress in transgenic Caenorhabditis elegans. BMC Neurosci. 2005 Aug 25;6:54. doi: 10.1186/1471-2202-6-54. PMID: 16122394; PMCID: PMC1215487. 2. Pan W, Ikeda K, Takebe M, Yamori Y. Genistein, daidzein and glycitein inhibit growth and DNA synthesis of aortic smooth muscle cells from stroke-prone spontaneously hypertensive rats. J Nutr. 2001 Apr;131(4):1154-8. doi: 10.1093/jn/131.4.1154. PMID: 11285318.
1: Zhang B, Su JP, Bai Y, Li J, Liu YH. Inhibitory effects of O-methylated isoflavone glycitein on human breast cancer SKBR-3 cells. Int J Clin Exp Pathol. 2015 Jul 1;8(7):7809-17. eCollection 2015. PubMed PMID: 26339345; PubMed Central PMCID: PMC4555673. 2: Hu YJ, Gao KG, Zheng CT, Wu ZJ, Yang XF, Wang L, Ma XY, Zhou AG, Jiang ZJ. Effect of dietary supplementation with glycitein during late pregnancy and lactation on antioxidative indices and performance of primiparous sows. J Anim Sci. 2015 May;93(5):2246-54. doi: 10.2527/jas.2014-7767. Erratum in: J Anim Sci. 2015 Jun;93(6):3226. PubMed PMID: 26020321. 3: Artigot MP, Baes M, Daydé J, Berger M. Expression of flavonoid 6-hydroxylase candidate genes in normal and mutant soybean genotypes for glycitein content. Mol Biol Rep. 2013 Jul;40(7):4361-9. doi: 10.1007/s11033-013-2526-2. Epub 2013 May 22. PubMed PMID: 23695494. 4: Shinkaruk S, Durand M, Lamothe V, Carpaye A, Martinet A, Chantre P, Vergne S, Nogues X, Moore N, Bennetau-Pelissero C. Bioavailability of glycitein relatively to other soy isoflavones in healthy young Caucasian men. Food Chem. 2012 Dec 1;135(3):1104-11. doi: 10.1016/j.foodchem.2012.03.135. Epub 2012 May 22. PubMed PMID: 22953831. 5: Roh C. Microbial transformation of bioactive compounds and production of ortho-dihydroxyisoflavones and glycitein from natural fermented soybean paste. Biomolecules. 2014 Dec 12;4(4):1093-101. doi: 10.3390/biom4041093. PubMed PMID: 25513748; PubMed Central PMCID: PMC4279171. 6: Winzer M, Rauner M, Pietschmann P. Glycitein decreases the generation of murine osteoclasts and increases apoptosis. Wien Med Wochenschr. 2010 Sep;160(17-18):446-51. doi: 10.1007/s10354-010-0811-4. Epub 2010 Aug 16. PubMed PMID: 20714813. 7: Shimoda K, Hamada H. Synthesis of beta-maltooligosaccharides of glycitein and daidzein and their anti-oxidant and anti-allergic activities. Molecules. 2010 Jul 29;15(8):5153-61. doi: 10.3390/molecules15085153. PubMed PMID: 20714292. 8: Lee EJ, Kim SY, Hyun JW, Min SW, Kim DH, Kim HS. Glycitein inhibits glioma cell invasion through down-regulation of MMP-3 and MMP-9 gene expression. Chem Biol Interact. 2010 Apr 15;185(1):18-24. doi: 10.1016/j.cbi.2010.02.037. Epub 2010 Feb 25. PubMed PMID: 20188714. 9: Kang KA, Zhang R, Piao MJ, Lee KH, Kim BJ, Kim SY, Kim HS, Kim DH, You HJ, Hyun JW. Inhibitory effects of glycitein on hydrogen peroxide induced cell damage by scavenging reactive oxygen species and inhibiting c-Jun N-terminal kinase. Free Radic Res. 2007 Jun;41(6):720-9. PubMed PMID: 17516245. 10: Gutierrez-Zepeda A, Santell R, Wu Z, Brown M, Wu Y, Khan I, Link CD, Zhao B, Luo Y. Soy isoflavone glycitein protects against beta amyloid-induced toxicity and oxidative stress in transgenic Caenorhabditis elegans. BMC Neurosci. 2005 Aug 25;6:54. PubMed PMID: 16122394; PubMed Central PMCID: PMC1215487. 11: Kim JH, Park DK, Lee CH, Yoon DY. A new isoflavone glycitein 7-O-beta-D-glucoside 4''-O-methylate, isolated from Cordyceps militaris grown on germinated soybeans extract, inhibits EGF-induced mucus hypersecretion in the human lung mucoepidermoid cells. Phytother Res. 2012 Dec;26(12):1807-12. doi: 10.1002/ptr.4655. Epub 2012 Mar 9. PubMed PMID: 22407817. 12: Simons AL, Renouf M, Hendrich S, Murphy PA. Metabolism of glycitein (7,4'-dihydroxy-6-methoxy-isoflavone) by human gut microflora. J Agric Food Chem. 2005 Nov 2;53(22):8519-25. PubMed PMID: 16248547. 13: Shinkaruk S, Lamothe V, Schmitter JM, Fructus A, Sauvant P, Vergne S, Degueil M, Babin P, Bennetau B, Bennetau-Pelissero C. Synthesis of haptens and conjugates for ELISA of glycitein: development and validation of an immunological test. J Agric Food Chem. 2008 Aug 27;56(16):6809-17. doi: 10.1021/jf800663s. Epub 2008 Jul 23. PubMed PMID: 18646854. 14: Clubbs EA, Bomser JA. Basal cell induced differentiation of noncancerous prostate epithelial cells (RWPE-1) by glycitein. Nutr Cancer. 2009;61(3):390-6. doi: 10.1080/01635580802582728. PubMed PMID: 19373613. 15: Song TT, Hendrich S, Murphy PA. Estrogenic activity of glycitein, a soy isoflavone. J Agric Food Chem. 1999 Apr;47(4):1607-10. Erratum in: J Agric Food Chem 2002 Apr 10;50(8):2470. PubMed PMID: 10564025. 16: Lee SO, Renouf M, Ye Z, Murphy PA, Hendrich S. Isoflavone glycitein diminished plasma cholesterol in female golden Syrian hamsters. J Agric Food Chem. 2007 Dec 26;55(26):11063-7. Epub 2007 Nov 27. PubMed PMID: 18038972. 17: Boltovets P, Shinkaruk S, Bennetau-Pelissero C, Bennetau B, Snopok B. The effect of low pH on the glycitein-BSA conjugate interaction with specific antiserum: competitive inhibition study using surface plasmon resonance technique. Talanta. 2011 May 15;84(3):867-73. doi: 10.1016/j.talanta.2011.02.008. Epub 2011 Feb 19. PubMed PMID: 21482295. 18: Hur H, Rafii F. Biotransformation of the isoflavonoids biochanin A, formononetin, and glycitein by Eubacterium limosum. FEMS Microbiol Lett. 2000 Nov 1;192(1):21-5. PubMed PMID: 11040423. 19: Zhang Y, Wang GJ, Song TT, Murphy PA, Hendrich S. Urinary disposition of the soybean isoflavones daidzein, genistein and glycitein differs among humans with moderate fecal isoflavone degradation activity. J Nutr. 1999 May;129(5):957-62. Erratum in: J Nutr 2001 Jan;131(1):147-8. PubMed PMID: 10222386. 20: Klus K, Barz W. Formation of polyhydroxylated isoflavones from the soybean seed isoflavones daidzein and glycitein by bacteria isolated from tempe. Arch Microbiol. 1995 Dec;164(6):428-34. PubMed PMID: 8588745.

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