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MedKoo Cat#: 573544 | Name: Equol
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Description:

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

Equol is a non-steroidal Estrogen generated when soybean products are metabolized by certain bacteria in the intestines. Equol is an antagonist of dihydrotestosterone and has implications for prostate cancer and other androgen-mediated pathologies.

Chemical Structure

Equol
Equol
CAS#531-95-3 (S-isomer)

Theoretical Analysis

MedKoo Cat#: 573544

Name: Equol

CAS#: 531-95-3 (S-isomer)

Chemical Formula: C15H14O3

Exact Mass: 242.0943

Molecular Weight: 242.27

Elemental Analysis: C, 74.36; H, 5.82; O, 19.81

Price and Availability

Size Price Availability Quantity
100mg USD 450.00 2 Weeks
250mg USD 850.00 2 Weeks
500mg USD 1,250.00 2 Weeks
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Related CAS #
531-95-3 (S-isomer) 221054-79-1 (R-isomer) 94105-90-5 (racemic)
Synonym
(-)-(S)-Equol; (-)-Equol; (3S)-Equol; (S)-Equol; S-Equol; Equol; AUS 131; AUS131; AUS-131;
IUPAC/Chemical Name
(S)-3,4-Dihydro-3-(4-hydroxyphenyl)-2H-1-benzopyran-7-ol
InChi Key
ADFCQWZHKCXPAJ-GFCCVEGCSA-N
InChi Code
1S/C15H14O3/c16-13-4-1-10(2-5-13)12-7-11-3-6-14(17)8-15(11)18-9-12/h1-6,8,12,16-17H,7,9H2/t12-/m1/s1
SMILES Code
C1[C@H](c2ccc(cc2)O)Cc2ccc(cc2O1)O
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
>3 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:
(-)-(S)-Equol is a high affinity ligand for estrogen receptor β with a Ki of 0.73 nM.
In vitro activity:
This study investigated the effects of S-Equol on OA progress in which rat primary chondrocytes were treated with sodium nitroprusside (SNP) to mimic OA progress with or without the co-addition of S-Equol for the evaluation of S-Equol's efficacy on OA. Results showed treatment of 0.8 mM SNP caused cell death, and increased oxidative stress (NO and H2O2), apoptosis, and proteoglycan loss. Furthermore, the expressions of MMPs of MMP-2, MMP-3, MMP-9, and MMP-13 and p53 were increased. The addition of 30 μM S-Equol could lessen those caused by SNP. Moreover, S-Equol activates the PI3K/Akt pathway, which is an upstream regulation of p53 and NO production and is associated with apoptosis and matrix degradation. As a pretreatment of phosphoinositide 3-kinases (PI3K) inhibitor, all S-Equol protective functions against SNP decrease or disappear. In conclusion, through PI3K/Akt activation, S-Equol can protect chondrocytes against SNP-induced matrix degradation and apoptosis, which are commonly found in OA, suggesting S-Equol is a potential for OA prevention. Reference: Int J Mol Sci. 2021 Jul; 22(13): 7054. https://www.ncbi.nlm.nih.gov/pmc/articles/PMC8268809/
In vivo activity:
Electrophysiological recordings indicated that exogenous S-equol alters cortical neuronal physiology. This study found that entorhinal cortex neurons are hyperexcitable in TMEV-infected mice, and exogenous application of microbial-derived S-equol ameliorated this TMEV-induced hyperexcitability. Reference: Epilepsia. 2021 Jul 2. doi: 10.1111/epi.16979. https://pubmed.ncbi.nlm.nih.gov/34212377/
Solvent mg/mL mM
Solubility
DMSO 48.1 198.37
DMF 15.0 61.91
Ethanol 30.7 126.88
Ethanol:PBS (pH 7.2) (1:10) 0.1 0.41
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 242.27 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. Huang LW, Huang TC, Hu YC, Hsieh BS, Cheng HL, Chiu PR, Chang KL. S-Equol Protects Chondrocytes against Sodium Nitroprusside-Caused Matrix Loss and Apoptosis through Activating PI3K/Akt Pathway. Int J Mol Sci. 2021 Jun 30;22(13):7054. doi: 10.3390/ijms22137054. PMID: 34209006; PMCID: PMC8268809. 2. Johnson SL, Park HY, Vattem DA, Grammas P, Ma H, Seeram NP. Equol, a Blood-Brain Barrier Permeable Gut Microbial Metabolite of Dietary Isoflavone Daidzein, Exhibits Neuroprotective Effects against Neurotoxins Induced Toxicity in Human Neuroblastoma SH-SY5Y Cells and Caenorhabditis elegans. Plant Foods Hum Nutr. 2020 Dec;75(4):512-517. doi: 10.1007/s11130-020-00840-0. PMID: 32761299. 3. Gallucci A, Patel DC, Thai K, Trinh J, Gude R, Shukla D, Campbell SL. Gut metabolite S-equol ameliorates hyperexcitability in entorhinal cortex neurons following Theiler murine encephalomyelitis virus-induced acute seizures. Epilepsia. 2021 Jul 2. doi: 10.1111/epi.16979. Epub ahead of print. PMID: 34212377. 4. McLaurin KA, Bertrand SJ, Illenberger JM, Harrod SB, Mactutus CF, Booze RM. S-Equol mitigates motivational deficits and dysregulation associated with HIV-1. Sci Rep. 2021 Jun 4;11(1):11870. doi: 10.1038/s41598-021-91240-0. PMID: 34088932; PMCID: PMC8178385.
In vitro protocol:
1. Huang LW, Huang TC, Hu YC, Hsieh BS, Cheng HL, Chiu PR, Chang KL. S-Equol Protects Chondrocytes against Sodium Nitroprusside-Caused Matrix Loss and Apoptosis through Activating PI3K/Akt Pathway. Int J Mol Sci. 2021 Jun 30;22(13):7054. doi: 10.3390/ijms22137054. PMID: 34209006; PMCID: PMC8268809. 2. Johnson SL, Park HY, Vattem DA, Grammas P, Ma H, Seeram NP. Equol, a Blood-Brain Barrier Permeable Gut Microbial Metabolite of Dietary Isoflavone Daidzein, Exhibits Neuroprotective Effects against Neurotoxins Induced Toxicity in Human Neuroblastoma SH-SY5Y Cells and Caenorhabditis elegans. Plant Foods Hum Nutr. 2020 Dec;75(4):512-517. doi: 10.1007/s11130-020-00840-0. PMID: 32761299.
In vivo protocol:
1. Gallucci A, Patel DC, Thai K, Trinh J, Gude R, Shukla D, Campbell SL. Gut metabolite S-equol ameliorates hyperexcitability in entorhinal cortex neurons following Theiler murine encephalomyelitis virus-induced acute seizures. Epilepsia. 2021 Jul 2. doi: 10.1111/epi.16979. Epub ahead of print. PMID: 34212377. 2. McLaurin KA, Bertrand SJ, Illenberger JM, Harrod SB, Mactutus CF, Booze RM. S-Equol mitigates motivational deficits and dysregulation associated with HIV-1. Sci Rep. 2021 Jun 4;11(1):11870. doi: 10.1038/s41598-021-91240-0. PMID: 34088932; PMCID: PMC8178385.
1: Mahalingam S, Gao L, Gonnering M, Helferich W, Flaws JA. Equol inhibits growth, induces atresia, and inhibits steroidogenesis of mouse antral follicles in vitro. Toxicol Appl Pharmacol. 2016 Mar 15;295:47-55. doi: 10.1016/j.taap.2016.02.009. PubMed PMID: 26876617; PubMed Central PMCID: PMC4779678. 2: Hazim S, Curtis PJ, Schär MY, Ostertag LM, Kay CD, Minihane AM, Cassidy A. Acute benefits of the microbial-derived isoflavone metabolite equol on arterial stiffness in men prospectively recruited according to equol producer phenotype: a double-blind randomized controlled trial. Am J Clin Nutr. 2016 Mar;103(3):694-702. doi: 10.3945/ajcn.115.125690. PubMed PMID: 26843154; PubMed Central PMCID: PMC4763500. 3: Pawlowski JW, Martin BR, McCabe GP, McCabe L, Jackson GS, Peacock M, Barnes S, Weaver CM. Impact of equol-producing capacity and soy-isoflavone profiles of supplements on bone calcium retention in postmenopausal women: a randomized crossover trial. Am J Clin Nutr. 2015 Sep;102(3):695-703. doi: 10.3945/ajcn.114.093906. PubMed PMID: 26245807; PubMed Central PMCID: PMC4548170. 4: Yang ZP, Zhao Y, Huang F, Chen J, Yao YH, Li J, Wu XN. Equol inhibits proliferation of human gastric carcinoma cells via modulating Akt pathway. World J Gastroenterol. 2015 Sep 28;21(36):10385-99. doi: 10.3748/wjg.v21.i36.10385. PubMed PMID: 26420965; PubMed Central PMCID: PMC4579885. 5: Liu ZM, Ho SC, Chen YM, Xie YJ, Huang ZG, Ling WH. Research protocol: effect of natural S-equol on blood pressure and vascular function--a six-month randomized controlled trial among equol non-producers of postmenopausal women with prehypertension or untreated stage 1 hypertension. BMC Complement Altern Med. 2016 Mar 1;16:89. doi: 10.1186/s12906-016-1065-5. PubMed PMID: 26928904; PubMed Central PMCID: PMC4772692. 6: Loutchanwoot P, Srivilai P, Jarry H. The influence of equol on the hypothalamic-pituitary-thyroid axis and hepatic lipid metabolic parameters in adult male rats. Life Sci. 2015 May 1;128:1-7. doi: 10.1016/j.lfs.2015.02.002. PubMed PMID: 25744395. 7: Pažoureková S, Lucová M, Nosál R, Drábiková K, Harmatha J, Šmidrkal J, Jančinová V. Equol Effectively Inhibits Toxic Activity of Human Neutrophils without Influencing Their Viability. Pharmacology. 2016;97(3-4):138-45. doi: 10.1159/000443177. PubMed PMID: 26745858. 8: Lee PG, Kim J, Kim EJ, Jung E, Pandey BP, Kim BG. P212A Mutant of Dihydrodaidzein Reductase Enhances (S)-Equol Production and Enantioselectivity in a Recombinant Escherichia coli Whole-Cell Reaction System. Appl Environ Microbiol. 2016 Jan 22;82(7):1992-2002. doi: 10.1128/AEM.03584-15. PubMed PMID: 26801575; PubMed Central PMCID: PMC4807523. 9: de la Parra C, Borrero-Garcia LD, Cruz-Collazo A, Schneider RJ, Dharmawardhane S. Equol, an isoflavone metabolite, regulates cancer cell viability and protein synthesis initiation via c-Myc and eIF4G. J Biol Chem. 2015 Mar 6;290(10):6047-57. doi: 10.1074/jbc.M114.617415. PubMed PMID: 25593313; PubMed Central PMCID: PMC4358247. 10: Acharjee S, Zhou JR, Elajami TK, Welty FK. Effect of soy nuts and equol status on blood pressure, lipids and inflammation in postmenopausal women stratified by metabolic syndrome status. Metabolism. 2015 Feb;64(2):236-43. doi: 10.1016/j.metabol.2014.09.005. PubMed PMID: 25441251. 11: Redruello B, Guadamuro L, Cuesta I, Álvarez-Buylla JR, Mayo B, Delgado S. A novel UHPLC method for the rapid and simultaneous determination of daidzein, genistein and equol in human urine. J Chromatogr B Analyt Technol Biomed Life Sci. 2015 Nov 15;1005:1-8. doi: 10.1016/j.jchromb.2015.09.029. PubMed PMID: 26444491. 12: Taghizadeh B, Ghavami L, Nikoofar A, Goliaei B. Equol as a potent radiosensitizer in estrogen receptor-positive and -negative human breast cancer cell lines. Breast Cancer. 2015 Jul;22(4):382-90. doi: 10.1007/s12282-013-0492-0. PubMed PMID: 24014377. 13: Ohkura Y, Obayashi S, Yamada K, Yamada M, Kubota T. S-equol Partially Restored Endothelial Nitric Oxide Production in Isoflavone-deficient Ovariectomized Rats. J Cardiovasc Pharmacol. 2015 May;65(5):500-7. doi: 10.1097/FJC.0000000000000220. PubMed PMID: 25636070. 14: Kim EY, Shin JY, Park YJ, Kim AK. Equol induces mitochondria-mediated apoptosis of human cervical cancer cells. Anticancer Res. 2014 Sep;34(9):4985-92. PubMed PMID: 25202081. 15: Rui X, Xu X, Wu H, Li W, Chen X, Jiang M, Dong M. A survey of equol contents in Chinese stinky tofu with emphasis on the effects of cooking methods. Int J Food Sci Nutr. 2014 Sep;65(6):667-72. doi: 10.3109/09637486.2014.908171. PubMed PMID: 24720564. 16: Newton KM, Reed SD, Uchiyama S, Qu C, Ueno T, Iwashita S, Gunderson G, Fuller S, Lampe JW. A cross-sectional study of equol producer status and self-reported vasomotor symptoms. Menopause. 2015 May;22(5):489-95. doi: 10.1097/GME.0000000000000363. PubMed PMID: 25380274. 17: Yu W, Deng X, Ma Z, Wang Y. Equol protects PC12 neuronal cells against hypoxia/reoxygenation injury in vitro by reducing reactive oxygen species production. Nan Fang Yi Ke Da Xue Xue Bao. 2016 Jan;36(1):1-7. PubMed PMID: 26806730. 18: Utian WH, Jones M, Setchell KD. S-equol: a potential nonhormonal agent for menopause-related symptom relief. J Womens Health (Larchmt). 2015 Mar;24(3):200-8. doi: 10.1089/jwh.2014.5006. PubMed PMID: 25692726. 19: Gou Z, Jiang S, Zheng C, Tian Z, Lin X. Equol Inhibits LPS-Induced Oxidative Stress and Enhances the Immune Response in Chicken HD11 Macrophages. Cell Physiol Biochem. 2015;36(2):611-21. PubMed PMID: 25997976. 20: Brown NM, Galandi SL, Summer SS, Zhao X, Heubi JE, King EC, Setchell KD. S-(-)equol production is developmentally regulated and related to early diet composition. Nutr Res. 2014 May;34(5):401-9. doi: 10.1016/j.nutres.2014.03.005. PubMed PMID: 24916553; PubMed Central PMCID: PMC5027651.