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MedKoo Cat#: 565571 | Name: (-)-5-Hydroxy-equol

Description:

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

(-)-5-Hydroxy-equol is a natural microbial metabolite of isoflavone genistein, increasing the lifespan and improving the thermal and oxidative stress tolerance of c. elegans

Chemical Structure

(-)-5-Hydroxy-equol
(-)-5-Hydroxy-equol
CAS#276669-86-4 (S-isomer)

Theoretical Analysis

MedKoo Cat#: 565571

Name: (-)-5-Hydroxy-equol

CAS#: 276669-86-4 (S-isomer)

Chemical Formula: C15H14O4

Exact Mass: 258.0892

Molecular Weight: 258.27

Elemental Analysis: C, 69.76; H, 5.46; O, 24.78

Price and Availability

This product is currently not in stock but may be available through custom synthesis. To ensure cost efficiency, the minimum order quantity is 1 gram. The estimated lead time is 2 to 4 months, with pricing dependent on the complexity of the synthesis (typically high for intricate chemistries). Quotes for quantities below 1 gram will not be provided. To request a quote, please click the button below. Note: If this product becomes available in stock in the future, pricing will be listed accordingly.
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Related CAS #
276669-86-4 (S-isomer) 2765078-84-8 (R-isomer)
Synonym
(-)-5-Hydroxy-equol; (-) 5 Hydroxy equol; (-)5Hydroxyequol; (-)-HO-equol; (-) HO equol; (-)HOequol; (S)-5-Hydroxy-equol
IUPAC/Chemical Name
(S)-3-(4-Hydroxyphenyl)chromane-5,7-diol
InChi Key
QUQOSUMQYPIQFW-SNVBAGLBSA-N
InChi Code
InChI=1S/C15H14O4/c16-11-3-1-9(2-4-11)10-5-13-14(18)6-12(17)7-15(13)19-8-10/h1-4,6-7,10,16-18H,5,8H2/t10-/m1/s1
SMILES Code
OC1=CC(O)=CC2=C1C[C@@H](C3=CC=C(O)C=C3)CO2
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
>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

Preparing Stock Solutions

The following data is based on the product molecular weight 258.27 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
1: Gao L, Wang KX, Zhang NN, Li JQ, Qin XM, Wang XL. (1)H Nuclear Magnetic Resonance Based Metabolomics Approach Reveals the Metabolic Mechanism of (-)-5-Hydroxy-equol against Hepatocellular Carcinoma Cells in Vitro. J Proteome Res. 2018 May 4;17(5):1833-1843. doi: 10.1021/acs.jproteome.7b00853. Epub 2018 Apr 10. PubMed PMID: 29589762. 2: Lee PG, Kim J, Kim EJ, Lee SH, Choi KY, Kazlauskas RJ, Kim BG. Biosynthesis of (-)-5-Hydroxy-equol and 5-Hydroxy-dehydroequol from Soy Isoflavone, Genistein Using Microbial Whole Cell Bioconversion. ACS Chem Biol. 2017 Nov 17;12(11):2883-2890. doi: 10.1021/acschembio.7b00624. Epub 2017 Oct 23. PubMed PMID: 28985044. 3: Gaya P, Sánchez-Jiménez A, Peirotén Á, Medina M, Landete JM. Incomplete metabolism of phytoestrogens by gut microbiota from children under the age of three. Int J Food Sci Nutr. 2018 May;69(3):334-343. doi: 10.1080/09637486.2017.1353955. Epub 2017 Jul 20. PubMed PMID: 28728453. 4: Schröder C, Matthies A, Engst W, Blaut M, Braune A. Identification and expression of genes involved in the conversion of daidzein and genistein by the equol-forming bacterium Slackia isoflavoniconvertens. Appl Environ Microbiol. 2013 Jun;79(11):3494-502. doi: 10.1128/AEM.03693-12. Epub 2013 Mar 29. PubMed PMID: 23542626; PubMed Central PMCID: PMC3648055. 5: Matthies A, Loh G, Blaut M, Braune A. Daidzein and genistein are converted to equol and 5-hydroxy-equol by human intestinal Slackia isoflavoniconvertens in gnotobiotic rats. J Nutr. 2012 Jan;142(1):40-6. doi: 10.3945/jn.111.148247. Epub 2011 Nov 23. PubMed PMID: 22113864. 6: Matthies A, Blaut M, Braune A. Isolation of a human intestinal bacterium capable of daidzein and genistein conversion. Appl Environ Microbiol. 2009 Mar;75(6):1740-4. doi: 10.1128/AEM.01795-08. Epub 2009 Jan 9. PubMed PMID: 19139227; PubMed Central PMCID: PMC2655447. 7: Matthies A, Clavel T, Gütschow M, Engst W, Haller D, Blaut M, Braune A. Conversion of daidzein and genistein by an anaerobic bacterium newly isolated from the mouse intestine. Appl Environ Microbiol. 2008 Aug;74(15):4847-52. doi: 10.1128/AEM.00555-08. Epub 2008 Jun 6. PubMed PMID: 18539813; PubMed Central PMCID: PMC2519357.