(-)-5-Hydroxy-equol

• CAT Number: I020967
• Molecular Formula: C15H14O4
• Molecular Weight: 258.273
• Purity: 98%
• Synonyms: (-)-5-Hydroxy-equol; (-) 5 Hydroxy equol; (-)5Hydroxyequol; (-)-HO-equol; (-) HO equol; (-)HOequol; (S)-5-Hydroxy-equol
• Solubility: Soluble in DMSO
• Appearance: Solid powder
• Storage: Dry, dark and at 0 - 4 C for short term (days to weeks) or -20 C for long term (months to years).
• IUPAC Name: (S)-3-(4-Hydroxyphenyl)chromane-5,7-diol
• InChI: 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
• InChIKey: QUQOSUMQYPIQFW-SNVBAGLBSA-N
• SMILES: OC1=CC(O)=CC2=C1C[C@@H](C3=CC=C(O)C=C3)CO2

(-)-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

Reference

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.
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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.