Daidzein
featured

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

MedKoo CAT#: 562482

CAS#: 486-66-8

Description: Daidzein is an anticancer agent. It acts by preventing hormone-induced cancers and arresting cell cycle at G1.


Chemical Structure

img
Daidzein
CAS# 486-66-8

Theoretical Analysis

MedKoo Cat#: 562482
Name: Daidzein
CAS#: 486-66-8
Chemical Formula: C15H10O4
Exact Mass: 254.0579
Molecular Weight: 254.241
Elemental Analysis: C, 70.86; H, 3.96; O, 25.17

Price and Availability

Size Price Availability Quantity
100.0mg USD 160.0 2 Weeks
500.0mg USD 300.0 2 Weeks
1.0g USD 530.0 2 Weeks
Bulk inquiry

Synonym: Daidzein; Daidzeol; Isoaurostatin;

IUPAC/Chemical Name: 4',7-Dihydroxyisoflavone

InChi Key: ZQSIJRDFPHDXIC-UHFFFAOYSA-N

InChi Code: InChI=1S/C15H10O4/c16-10-3-1-9(2-4-10)13-8-19-14-7-11(17)5-6-12(14)15(13)18/h1-8,16-17H

SMILES Code: O=C1C(C2=CC=C(O)C=C2)=COC3=C1C=CC(O)=C3

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

Product Data:

Biological target: Daidzein is a soy isoflavone, which acts as a PPAR activator.
In vitro activity: This study was undertaken to investigate the anticancer effects of Daidzein on human melanoma cells and also an attempt was made to decipher the underlying mechanisms. The results of MTT assay showed that Daidzein causes significant decrease in the proliferation of the melanoma A-375 cells and showed an IC50 of 18 µM. However, the IC50 of Daidzein was very high against the normal HEMnLP cells, indicative of low cytotoxicity. Flow cytometry showed significant arrest of the A-375 cells at the G0/G1 phase of the cell cycle. Western blot analysis showed that the molecule suppressed the expression cell cycle regulatory proteins such as cyclin D1, CDK4, CDK6 and p27. DAPI and annexin V/PI staining assays showed that Daidzein prompted apoptosis in A-375 melanoma cells which was concomitant with depletion of Bcl-2, increase of Bax and activation of cleavage of caspase-3 and caspase-9. Electron microscopic analysis showed that the molecule led to the development of autophagosomes in A-375 cells, which was also concomitant with increase in the expression of LC3B II and decrease in the expression of p62. Finally, Daidzein also suppressed the phosphorylation of PI3K and AKT, causing deactivation of the PI3K/AKT signalling pathway. In conclusion, daidzein may prove beneficial in the development of melanoma systemic therapy. Reference: BUON. Jan-Feb 2020;25(1):485-490. https://pubmed.ncbi.nlm.nih.gov/32277673/
In vivo activity: A possibility of daidzein-induced long-term neuroprotection was assessed in mice treated with daidzein for 1 month. Ratios of strokeinduced mRNA levels against the contralateral hemisphere showed similar increases in Lxr, Scarb1, Abca1, Apoe, Tsp2, and Gfap mRNA in both vehicle and daidzein-treated groups (Fig. 4A; Table 2). Compared with vehicle treatment, daidzein significantly elevated Abca1, Abcg1, and Apoe mRNAs at 1 month after stroke (Fig. 4B–E). For lipogenic genes, daidzein increased strokeinduced Srebp1 mRNA without affecting Fas and Lpl expression (Table 2). ApoE protein was also significantly increased at this time (Fig. 4F). There was no difference in expression of the cholesterol homeostasis genes in age-matched sham mice treated with vehicle or daidzein for 1 month (data not shown). Because stroke causes atrophy, brain volume representing noninjured tissue, ischemic scar tissue, remaining total ipsilateral tissue, and resorbed tissue (estimated infarct) were analyzed. No differences were found in any of these region volumes (Fig. 4G), confirming that daidzein-induced cholesterol homeostasis genetic program uncouples with neuroprotection. Reference: J Neurosci. 2015 Nov 11; 35(45): 15113–15126. https://www.ncbi.nlm.nih.gov/pmc/articles/PMC4642242/

Solubility Data

Solvent Max Conc. mg/mL Max Conc. mM
Solubility
DMSO 39.0 153.4

Preparing Stock Solutions

The following data is based on the product molecular weight 254.241 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. Guo JM, Xiao BX, Dai DJ, Liu Q, Ma HH. Effects of daidzein on estrogen-receptor-positive and negative pancreatic cancer cells in vitro. World J Gastroenterol. 2004 Mar 15;10(6):860-3. doi: 10.3748/wjg.v10.i6.860. PMID: 15040033; PMCID: PMC4726994. 2. Chu H, Li J, Liu T, Miao N, Zhang W. Anticancer effects of Daidzein against the human melanoma cell lines involves cell cycle arrest, autophagy and deactivation of PI3K/AKT signalling pathways. J BUON. 2020 Jan-Feb;25(1):485-490. PMID: 32277673. 3. Kim E, Woo MS, Qin L, Ma T, Beltran CD, Bao Y, Bailey JA, Corbett D, Ratan RR, Lahiri DK, Cho S. Daidzein Augments Cholesterol Homeostasis via ApoE to Promote Functional Recovery in Chronic Stroke. J Neurosci. 2015 Nov 11;35(45):15113-26. doi: 10.1523/JNEUROSCI.2890-15.2015. PMID: 26558782; PMCID: PMC4642242. 4. Heo HJ, Suh YM, Kim MJ, Choi SJ, Mun NS, Kim HK, Kim E, Kim CJ, Cho HY, Kim YJ, Shin DH. Daidzein activates choline acetyltransferase from MC-IXC cells and improves drug-induced amnesia. Biosci Biotechnol Biochem. 2006 Jan;70(1):107-11. doi: 10.1271/bbb.70.107. PMID: 16428827.
In vitro protocol: 1. Guo JM, Xiao BX, Dai DJ, Liu Q, Ma HH. Effects of daidzein on estrogen-receptor-positive and negative pancreatic cancer cells in vitro. World J Gastroenterol. 2004 Mar 15;10(6):860-3. doi: 10.3748/wjg.v10.i6.860. PMID: 15040033; PMCID: PMC4726994. 2. Chu H, Li J, Liu T, Miao N, Zhang W. Anticancer effects of Daidzein against the human melanoma cell lines involves cell cycle arrest, autophagy and deactivation of PI3K/AKT signalling pathways. J BUON. 2020 Jan-Feb;25(1):485-490. PMID: 32277673.
In vivo protocol: 1. Kim E, Woo MS, Qin L, Ma T, Beltran CD, Bao Y, Bailey JA, Corbett D, Ratan RR, Lahiri DK, Cho S. Daidzein Augments Cholesterol Homeostasis via ApoE to Promote Functional Recovery in Chronic Stroke. J Neurosci. 2015 Nov 11;35(45):15113-26. doi: 10.1523/JNEUROSCI.2890-15.2015. PMID: 26558782; PMCID: PMC4642242. 2. Heo HJ, Suh YM, Kim MJ, Choi SJ, Mun NS, Kim HK, Kim E, Kim CJ, Cho HY, Kim YJ, Shin DH. Daidzein activates choline acetyltransferase from MC-IXC cells and improves drug-induced amnesia. Biosci Biotechnol Biochem. 2006 Jan;70(1):107-11. doi: 10.1271/bbb.70.107. PMID: 16428827.

Molarity Calculator

Calculate the mass, volume, or concentration required for a solution.
=
x
x
g/mol

*When preparing stock solutions always use the batch-specific molecular weight of the product found on the vial label and SDS / CoA (available online).

Reconstitution Calculator

The reconstitution calculator allows you to quickly calculate the volume of a reagent to reconstitute your vial. Simply enter the mass of reagent and the target concentration and the calculator will determine the rest.

=
÷

Dilution Calculator

Calculate the dilution required to prepare a stock solution.
x
=
x

1: Applegate CC, Rowles JL, Ranard KM, Jeon S, Erdman JW. Soy Consumption and the Risk of Prostate Cancer: An Updated Systematic Review and Meta-Analysis. Nutrients. 2018 Jan 4;10(1). pii: E40. doi: 10.3390/nu10010040. Review. PubMed PMID: 29300347; PubMed Central PMCID: PMC5793268.

2: Rienks J, Barbaresko J, Nöthlings U. Association of isoflavone biomarkers with risk of chronic disease and mortality: a systematic review and meta-analysis of observational studies. Nutr Rev. 2017 Aug 1;75(8):616-641. doi: 10.1093/nutrit/nux021. Review. PubMed PMID: 28969363.

3: Probst Y, Guan V, Kent K. A systematic review of food composition tools used for determining dietary polyphenol intake in estimated intake studies. Food Chem. 2018 Jan 1;238:146-152. doi: 10.1016/j.foodchem.2016.11.010. Epub 2016 Nov 3. Review. PubMed PMID: 28867085.

4: Alamolhodaei NS, Tsatsakis AM, Ramezani M, Hayes AW, Karimi G. Resveratrol as MDR reversion molecule in breast cancer: An overview. Food Chem Toxicol. 2017 May;103:223-232. doi: 10.1016/j.fct.2017.03.024. Epub 2017 Mar 15. Review. PubMed PMID: 28315369.

5: Lee NK, Paik HD. Bioconversion Using Lactic Acid Bacteria: Ginsenosides, GABA, and Phenolic Compounds. J Microbiol Biotechnol. 2017 May 28;27(5):869-877. doi: 10.4014/jmb.1612.12005. Review. PubMed PMID: 28297748.

6: Fusi F, Spiga O, Trezza A, Sgaragli G, Saponara S. The surge of flavonoids as novel, fine regulators of cardiovascular Ca(v) channels. Eur J Pharmacol. 2017 Feb 5;796:158-174. doi: 10.1016/j.ejphar.2016.12.033. Epub 2016 Dec 22. Review. PubMed PMID: 28012974.

7: Ahmed T, Javed S, Tariq A, Budzyńska B, D'Onofrio G, Daglia M, Nabavi SF, Nabavi SM. Daidzein and its Effects on Brain. Curr Med Chem. 2017;24(4):365-375. doi: 10.2174/0929867323666161101140214. Review. PubMed PMID: 27804870.

8: Abdi F, Alimoradi Z, Haqi P, Mahdizad F. Effects of phytoestrogens on bone mineral density during the menopause transition: a systematic review of randomized, controlled trials. Climacteric. 2016 Dec;19(6):535-545. Epub 2016 Oct 6. Review. PubMed PMID: 27710141.

9: Zhang Q, Feng H, Qluwakemi B, Wang J, Yao S, Cheng G, Xu H, Qiu H, Zhu L, Yuan M. Phytoestrogens and risk of prostate cancer: an updated meta-analysis of epidemiologic studies. Int J Food Sci Nutr. 2017 Feb;68(1):28-42. doi: 10.1080/09637486.2016.1216525. Epub 2016 Aug 9. Review. PubMed PMID: 27687296.

10: Birru RL, Ahuja V, Vishnu A, Evans RW, Miyamoto Y, Miura K, Usui T, Sekikawa A. The impact of equol-producing status in modifying the effect of soya isoflavones on risk factors for CHD: a systematic review of randomised controlled trials. J Nutr Sci. 2016 Jul 19;5:e30. doi: 10.1017/jns.2016.18. eCollection 2016. Review. PubMed PMID: 27547393; PubMed Central PMCID: PMC4976117.

11: Liu CW, Murray JD. The Role of Flavonoids in Nodulation Host-Range Specificity: An Update. Plants (Basel). 2016 Aug 11;5(3). pii: E33. doi: 10.3390/plants5030033. Review. PubMed PMID: 27529286; PubMed Central PMCID: PMC5039741.

12: Ronis MJ. Effects of soy containing diet and isoflavones on cytochrome P450 enzyme expression and activity. Drug Metab Rev. 2016 Aug;48(3):331-41. doi: 10.1080/03602532.2016.1206562. Epub 2016 Jul 20. Review. PubMed PMID: 27440109; PubMed Central PMCID: PMC5801744.

13: Kruger MC, Wolber FM. Osteoporosis: Modern Paradigms for Last Century's Bones. Nutrients. 2016 Jun 17;8(6). pii: E376. doi: 10.3390/nu8060376. Review. PubMed PMID: 27322315; PubMed Central PMCID: PMC4924217.

14: Zhang M, Wang K, Chen L, Yin B, Song Y. Is phytoestrogen intake associated with decreased risk of prostate cancer? A systematic review of epidemiological studies based on 17,546 cases. Andrology. 2016 Jul;4(4):745-56. doi: 10.1111/andr.12196. Epub 2016 Jun 3. Review. PubMed PMID: 27260185.

15: Tomás-Barberán FA, González-Sarrías A, García-Villalba R, Núñez-Sánchez MA, Selma MV, García-Conesa MT, Espín JC. Urolithins, the rescue of "old" metabolites to understand a "new" concept: Metabotypes as a nexus among phenolic metabolism, microbiota dysbiosis, and host health status. Mol Nutr Food Res. 2017 Jan;61(1). doi: 10.1002/mnfr.201500901. Epub 2016 Jun 20. Review. PubMed PMID: 27158799.

16: Moosavi F, Hosseini R, Saso L, Firuzi O. Modulation of neurotrophic signaling pathways by polyphenols. Drug Des Devel Ther. 2015 Dec 21;10:23-42. doi: 10.2147/DDDT.S96936. eCollection 2016. Review. PubMed PMID: 26730179; PubMed Central PMCID: PMC4694682.

17: Chen F, Wen Q, Jiang J, Li HL, Tan YF, Li YH, Zeng NK. Could the gut microbiota reconcile the oral bioavailability conundrum of traditional herbs? J Ethnopharmacol. 2016 Feb 17;179:253-64. doi: 10.1016/j.jep.2015.12.031. Epub 2015 Dec 23. Review. PubMed PMID: 26723469.

18: Zaheer K, Humayoun Akhtar M. An updated review of dietary isoflavones: Nutrition, processing, bioavailability and impacts on human health. Crit Rev Food Sci Nutr. 2017 Apr 13;57(6):1280-1293. doi: 10.1080/10408398.2014.989958. Review. PubMed PMID: 26565435.

19: Taylor M. Complementary and Alternative Approaches to Menopause. Endocrinol Metab Clin North Am. 2015 Sep;44(3):619-48. doi: 10.1016/j.ecl.2015.05.008. Epub 2015 Jul 9. Review. PubMed PMID: 26316247.

20: Bircsak KM, Aleksunes LM. Interaction of Isoflavones with the BCRP/ABCG2 Drug Transporter. Curr Drug Metab. 2015;16(2):124-40. Review. PubMed PMID: 26179608; PubMed Central PMCID: PMC4713194.

Daidzein

100.0mg / USD 160.0