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

MedKoo CAT#: 540211

CAS#: 362-05-0

Description: 2-Hydroxyestradiol is an estradiol metabolite with low affinity for ERs. It decreases release of prostagladin E2, suppresses H202-induced oxidative damage, and inhibits HIF-1α signaling.


Price and Availability

Size
Price

5mg
USD 310
Size
Price

10mg
USD 545
Size
Price

25mg
USD 1100

2-Hydroxyestradiol purity > 98%, is in stock. Current shipping out time is about 2 weeks after order is received. CoA, QC data and MSDS documents are available in one week after order is received.


Chemical Structure

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Theoretical Analysis

MedKoo Cat#: 540211
Name: 2-Hydroxyestradiol
CAS#: 362-05-0
Chemical Formula: C18H24O3
Exact Mass: 288.1725
Molecular Weight: 288.38
Elemental Analysis: C, 74.97; H, 8.39; O, 16.64


Synonym: 2-Hydroxyestradiol; 2-OH-E2; 2-OH-Estradiol

IUPAC/Chemical Name: (8R,9S,13S,14S,17S)-13-methyl-7,8,9,11,12,13,14,15,16,17-decahydro-6H-cyclopenta[a]phenanthrene-2,3,17-triol

InChi Key: DILDHNKDVHLEQB-XSSYPUMDSA-N

InChi Code: InChI=1S/C18H24O3/c1-18-7-6-11-12(14(18)4-5-17(18)21)3-2-10-8-15(19)16(20)9-13(10)11/h8-9,11-12,14,17,19-21H,2-7H2,1H3/t11-,12+,14-,17-,18-/m0/s1

SMILES Code: C[C@@]12[C@@H](O)CC[C@@]1([H])[C@]3([H])CCC4=C(C=C(O)C(O)=C4)[C@@]3([H])CC2


Technical Data

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).

Harmonized System Code:
293490


References

1: Chourasia TK, Pang Y, Thomas P. The catecholestrogen, 2-hydroxyestradiol-17beta, acts as a G protein-coupled estrogen receptor 1 (GPER/GPR30) antagonist to promote the resumption of meiosis in zebrafish oocytes. Biol Reprod. 2015 Mar;92(3):69. doi: 10.1095/biolreprod.114.125674. Epub 2015 Jan 21. PubMed PMID: 25609836.

2: Higuchi A, Oonishi E, Kawakita T, Tsubota K. Evaluation of treatment for dry eye with 2-hydroxyestradiol using a dry eye rat model. Mol Vis. 2016 Apr 30;22:446-53. eCollection 2016. PubMed PMID: 27186071; PubMed Central PMCID: PMC4859160.

3: Babbs RK, Unger EL, Corwin RL. 2-Hydroxyestradiol enhances binge onset in female rats and reduces prefrontal cortical dopamine in male rats. Horm Behav. 2013 Jan;63(1):88-96. doi: 10.1016/j.yhbeh.2012.10.010. Epub 2012 Oct 29. PubMed PMID: 23116652; PubMed Central PMCID: PMC3586335.

4: Samartzis EP, Imesch P, Twiehaus A, Dubey RK, Leeners B. The estrogen metabolites 2-methoxyestradiol and 2-hydroxyestradiol inhibit endometriotic cell proliferation in estrogen-receptor-independent manner. Gynecol Endocrinol. 2016 Jul;32(7):529-33. doi: 10.3109/09513590.2015.1137094. Epub 2016 Jan 22. PubMed PMID: 26800447.

5: Anderson S, Oyama TT, Lindsley JN, Schutzer WE, Beard DR, Gattone VH 2nd, Komers R. 2-Hydroxyestradiol slows progression of experimental polycystic kidney disease. Am J Physiol Renal Physiol. 2012 Mar 1;302(5):F636-45. doi: 10.1152/ajprenal.00265.2011. Epub 2011 Dec 7. PubMed PMID: 22160773; PubMed Central PMCID: PMC3353649.

6: Enríquez J, Velázquez-Cruz R, Parra-Torres A, Gutiérrez-Sagal R, Larrea F. The anti-estrogenic activity of indole-3-carbinol in neonatal rat osteoblasts is associated with the estrogen receptor antagonist 2-hydroxyestradiol. J Endocrinol Invest. 2016 Oct;39(10):1149-58. doi: 10.1007/s40618-016-0494-9. Epub 2016 Jun 16. PubMed PMID: 27312859.

7: Schaufelberger SA, Rosselli M, Barchiesi F, Gillespie DG, Jackson EK, Dubey RK. 2-Methoxyestradiol, an endogenous 17β-estradiol metabolite, inhibits microglial proliferation and activation via an estrogen receptor-independent mechanism. Am J Physiol Endocrinol Metab. 2016 Mar 1;310(5):E313-22. doi: 10.1152/ajpendo.00418.2015. Epub 2016 Jan 5. PubMed PMID: 26732685; PubMed Central PMCID: PMC4773653.

8: Chourasia TK, Joy KP. In vitro effects of 2-hydroxyestradiol-17β on ovarian follicular steroid secretion in the catfish Heteropneustes fossilis and identification of the receptor and signaling mechanisms. Gen Comp Endocrinol. 2012 Feb 1;175(3):500-13. doi: 10.1016/j.ygcen.2011.12.007. Epub 2011 Dec 19. PubMed PMID: 22202599.

9: Babbs RK, Wojnicki FH, Corwin RL. Effect of 2-hydroxyestradiol on binge intake in rats. Physiol Behav. 2011 Jul 6;103(5):508-12. doi: 10.1016/j.physbeh.2011.03.029. Epub 2011 Apr 9. PubMed PMID: 21497615; PubMed Central PMCID: PMC3132134.

10: Hill BJ, Gebre S, Schlicker B, Jordan R, Necessary S. Nongenomic inhibition of coronary constriction by 17ß-estradiol, 2-hydroxyestradiol, and 2-methoxyestradiol. Can J Physiol Pharmacol. 2010 Feb;88(2):147-52. doi: 10.1139/Y09-120. PubMed PMID: 20237589; PubMed Central PMCID: PMC2910413.

11: Van Aswegen CH, Purdy RH, Wittliff JL. Binding of 2-hydroxyestradiol and 4-hydroxyestradiol to estrogen receptors from human breast cancers. J Steroid Biochem. 1989 Apr;32(4):485-92. PubMed PMID: 2542691.

12: Jellinck PH. 4-Hydroxyestradiol is conjugated with thiols primarily at C-2: evidence from regiospecific displacement of tritium by rat liver microsomes or tyrosinase. Steroids. 1988 Mar-Apr;51(3-4):395-409. PubMed PMID: 2851201.

13: Zacharia LC, Piché CA, Fielding RM, Holland KM, Allison SD, Dubey RK, Jackson EK. 2-hydroxyestradiol is a prodrug of 2-methoxyestradiol. J Pharmacol Exp Ther. 2004 Jun;309(3):1093-7. Epub 2004 Feb 10. PubMed PMID: 14872091.

14: Zacharia LC, Jackson EK, Gillespie DG, Dubey RK. Catecholamines abrogate antimitogenic effects of 2-hydroxyestradiol on human aortic vascular smooth muscle cells. Arterioscler Thromb Vasc Biol. 2001 Nov;21(11):1745-50. PubMed PMID: 11701460.

15: Fujii Y, Teranishi M, Ikeda Y, Yamazaki M, Kishida S, Miyabo S. Characterization of antisera to 2-hydroxyestradiol and 4-hydroxyestradiol using 6-(O-carboxymethyl)oxime- and 17-hemisuccinate-bovine serum albumin conjugates and radioimmunoassay. Steroids. 1985 Oct-Nov;46(4-5):857-65. PubMed PMID: 2428137.

16: Parada-Bustamante A, Valencia C, Reuquen P, Diaz P, Rincion-Rodriguez R, Orihuela PA. Role of 2-methoxyestradiol, an Endogenous Estrogen Metabolite, in Health and Disease. Mini Rev Med Chem. 2015;15(5):427-38. Review. PubMed PMID: 25723461.

17: Zacharia LC, Dubey RK, Mi Z, Jackson EK. Methylation of 2-hydroxyestradiol in isolated organs. Hypertension. 2003 Jul;42(1):82-7. Epub 2003 May 27. PubMed PMID: 12771046.

18: Merriam GR, MacLusky NJ, Johnson LA, Naftolin F. 2-hydroxyestradiol-17 alpha and 4-hydroxyestradiol-17 alpha, catechol estrogen analogs with reduced estrogen receptor affinity. Steroids. 1980 Jul;36(1):13-20. PubMed PMID: 7414655.

19: Miura T, Muraoka S, Ogiso T. Inhibition of lipid peroxidation by estradiol and 2-hydroxyestradiol. Steroids. 1996 Jun;61(6):379-83. PubMed PMID: 8776801.

20: Okatani Y, Fishman J. Effects of 2-hydroxyestradiol-17 beta, 2-hydroxyestradiol-17 alpha, and 4-hydroxyestrone on the preovulatory luteinizing hormone surge in the rat: agonist and antagonist actions. Endocrinology. 1984 Sep;115(3):1090-4. PubMed PMID: 6540166.