MedKoo Biosciences, Inc.
Tel:   +1-919-636-5577    Fax:   +1-919-980-4831    Email:   sales@medkoo.com
Search
Login Register
Search
MedKoo Cat#: 540211 | Name: 2-Hydroxyestradiol
Featured

Description:

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

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.

Chemical Structure

2-Hydroxyestradiol
2-Hydroxyestradiol
CAS#362-05-0

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

Price and Availability

Size Price Availability Quantity
5mg USD 450.00 2 Weeks
10mg USD 850.00 2 Weeks
Bulk Inquiry
Buy Now
Add to Cart
Related CAS #
No Data
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
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).
HS Tariff Code
2934.99.9001
More Info

Preparing Stock Solutions

The following data is based on the product molecular weight 288.38 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: 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.

View History

4-Octyl Itaconate

4-Octyl Itaconate

Featured