MedKoo Biosciences, Inc.
Tel:   +1-919-636-5577    Fax:   +1-919-980-4831    Email:   sales@medkoo.com
Search
Login Register
Search
MedKoo Cat#: 146214 | Name: Enterodiol

Description:

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

Enterodiol is a lignan-type phytoestrogen produced in the human gut through the microbial metabolism of plant lignans found in foods like flaxseed, whole grains, and vegetables. It exhibits mild estrogenic and antioxidant activity by binding to estrogen receptors and modulating hormonal balance. The mechanism of enterodiol involves its interaction with estrogen receptors, potentially influencing gene expression and cellular proliferation, especially in hormone-sensitive tissues. Applications of enterodiol are mainly in nutritional and medical research for its potential role in cancer prevention, cardiovascular health, and hormone regulation.

Chemical Structure

Enterodiol
Enterodiol
CAS#80226-00-2

Theoretical Analysis

MedKoo Cat#: 146214

Name: Enterodiol

CAS#: 80226-00-2

Chemical Formula: C18H22O4

Exact Mass: 302.1518

Molecular Weight: 302.37

Elemental Analysis: C, 71.50; H, 7.33; O, 21.16

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.
Bulk Inquiry
Related CAS #
No Data
Synonym
Enterodiol;
IUPAC/Chemical Name
(2R,3R)-2,3-bis(3-hydroxybenzyl)butane-1,4-diol
InChi Key
DWONJCNDULPHLV-HOTGVXAUSA-N
InChi Code
1S/C18H22O4/c19-11-15(7-13-3-1-5-17(21)9-13)16(12-20)8-14-4-2-6-18(22)10-14/h1-6,9-10,15-16,19-22H,7-8,11-12H2/t15-,16-/m0/s1
SMILES Code
OC[C@H](CC1=CC=CC(O)=C1)[C@H](CO)CC2=CC=CC(O)=C2
Appearance
To be determined
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
To be determined
Shelf Life
>2 years if stored properly
Drug Formulation
To be determined
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 302.37 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: Kase BE, Liese AD, Zhang J, Murphy EA, Zhao L, Steck SE. The Development and Evaluation of a Literature-Based Dietary Index for Gut Microbiota. Nutrients. 2024 Apr 3;16(7):1045. doi: 10.3390/nu16071045. PMID: 38613077; PMCID: PMC11013161. 2: Wang LQ. Mammalian phytoestrogens: enterodiol and enterolactone. J Chromatogr B Analyt Technol Biomed Life Sci. 2002 Sep 25;777(1-2):289-309. doi: 10.1016/s1570-0232(02)00281-7. PMID: 12270221. 3: de Athayde Moncorvo Collado A, Salazar PB, Minahk C. Enterodiol is Actively Transported by Rat Liver Cell Membranes. J Membr Biol. 2018 Aug;251(4):593-600. doi: 10.1007/s00232-018-0035-x. Epub 2018 May 4. PMID: 29728709. 4: Corsini E, Dell'Agli M, Facchi A, De Fabiani E, Lucchi L, Boraso MS, Marinovich M, Galli CL. Enterodiol and enterolactone modulate the immune response by acting on nuclear factor-kappaB (NF-kappaB) signaling. J Agric Food Chem. 2010 Jun 9;58(11):6678-84. doi: 10.1021/jf100471n. PMID: 20446732. 5: Shin MK, Jeon YD, Jin JS. Apoptotic effect of enterodiol, the final metabolite of edible lignans, in colorectal cancer cells. J Sci Food Agric. 2019 Mar 30;99(5):2411-2419. doi: 10.1002/jsfa.9448. Epub 2018 Dec 18. PMID: 30357838. 6: Jansen GH, Arts IC, Nielen MW, Müller M, Hollman PC, Keijer J. Uptake and metabolism of enterolactone and enterodiol by human colon epithelial cells. Arch Biochem Biophys. 2005 Mar 1;435(1):74-82. doi: 10.1016/j.abb.2004.12.015. PMID: 15680909. 7: Liu H, Liu J, Wang S, Zeng Z, Li T, Liu Y, Mastriani E, Li QH, Bao HX, Zhou YJ, Wang X, Hu S, Gao S, Qi Y, Shen Z, Wang H, Yu M, Gao T, Johnston RN, Liu SL. Enterolactone has stronger effects than enterodiol on ovarian cancer. J Ovarian Res. 2017 Jul 24;10(1):49. doi: 10.1186/s13048-017-0346-z. PMID: 28738876; PMCID: PMC5525236. 8: Feng J, Shi Z, Ye Z. Effects of metabolites of the lignans enterolactone and enterodiol on osteoblastic differentiation of MG-63 cells. Biol Pharm Bull. 2008 Jun;31(6):1067-70. doi: 10.1248/bpb.31.1067. PMID: 18520031. 9: Rowland I, Faughnan M, Hoey L, Wähälä K, Williamson G, Cassidy A. Bioavailability of phyto-oestrogens. Br J Nutr. 2003 Jun;89 Suppl 1:S45-58. doi: 10.1079/BJN2002796. PMID: 12725656. 10: Zhu J, Cai Z, Song Z, Li Y, Shim YY, Reaney MJT, Lee YY, Wang Y, Zhang N. Bioconversion of lignans in flaxseed cake by fermented tofu microbiota and isolation of Enterococcus faecium strain ZB26 responsible for converting secoisolariciresinol diglucoside to enterodiol. Food Chem. 2024 Nov 1;457:140077. doi: 10.1016/j.foodchem.2024.140077. Epub 2024 Jun 13. PMID: 38905833. 11: Jia M, Ning F, Wen J, Wang X, Chen J, Hu J, Chen X, Liu Z. Secoisolariciresinol diglucoside attenuates neuroinflammation and cognitive impairment in female Alzheimer's disease mice via modulating gut microbiota metabolism and GPER/CREB/BDNF pathway. J Neuroinflammation. 2024 Aug 12;21(1):201. doi: 10.1186/s12974-024-03195-4. PMID: 39135052; PMCID: PMC11320852. 12: Kulling SE, Jacobs E, Pfeiffer E, Metzler M. Studies on the genotoxicity of the mammalian lignans enterolactone and enterodiol and their metabolic precursors at various endpoints in vitro. Mutat Res. 1998 Aug 7;416(1-2):115-24. doi: 10.1016/s1383-5718(98)00082-5. PMID: 9725997. 13: Carreau C, Flouriot G, Bennetau-Pelissero C, Potier M. Enterodiol and enterolactone, two major diet-derived polyphenol metabolites have different impact on ERalpha transcriptional activation in human breast cancer cells. J Steroid Biochem Mol Biol. 2008 May;110(1-2):176-85. doi: 10.1016/j.jsbmb.2008.03.032. Epub 2008 Apr 4. PMID: 18457947. 14: Adlercreutz H, Fotsis T, Heikkinen R, Dwyer JT, Woods M, Goldin BR, Gorbach SL. Excretion of the lignans enterolactone and enterodiol and of equol in omnivorous and vegetarian postmenopausal women and in women with breast cancer. Lancet. 1982 Dec 11;2(8311):1295-9. doi: 10.1016/s0140-6736(82)91507-0. PMID: 6128595. 15: Wang LQ, Meselhy MR, Li Y, Qin GW, Hattori M. Human intestinal bacteria capable of transforming secoisolariciresinol diglucoside to mammalian lignans, enterodiol and enterolactone. Chem Pharm Bull (Tokyo). 2000 Nov;48(11):1606-10. doi: 10.1248/cpb.48.1606. PMID: 11086885. 16: Heinonen S, Nurmi T, Liukkonen K, Poutanen K, Wähälä K, Deyama T, Nishibe S, Adlercreutz H. In vitro metabolism of plant lignans: new precursors of mammalian lignans enterolactone and enterodiol. J Agric Food Chem. 2001 Jul;49(7):3178-86. doi: 10.1021/jf010038a. PMID: 11453749. 17: Plaha NS, Awasthi S, Sharma A, Kaushik N. Distribution, biosynthesis and therapeutic potential of lignans. 3 Biotech. 2022 Oct;12(10):255. doi: 10.1007/s13205-022-03318-9. Epub 2022 Sep 2. PMID: 36065422; PMCID: PMC9440181. 18: Power KA, Saarinen NM, Chen JM, Thompson LU. Mammalian lignans enterolactone and enterodiol, alone and in combination with the isoflavone genistein, do not promote the growth of MCF-7 xenografts in ovariectomized athymic nude mice. Int J Cancer. 2006 Mar 1;118(5):1316-20. doi: 10.1002/ijc.21464. PMID: 16152607. 19: Adlercreutz H. Lignans and human health. Crit Rev Clin Lab Sci. 2007;44(5-6):483-525. doi: 10.1080/10408360701612942. PMID: 17943494. 20: Frankenfeld CL. Cardiometabolic risk factors are associated with high urinary enterolactone concentration, independent of urinary enterodiol concentration and dietary fiber intake in adults. J Nutr. 2014 Sep;144(9):1445-53. doi: 10.3945/jn.114.190512. Epub 2014 Jun 25. PMID: 24966407.

View History

Fluspiperone

Fluspiperone