4-Hydroxyestradiol
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MedKoo CAT#: 462967

CAS#: 5976-61-4

Description: 4-Hydroxyestradiol is a catechol estrogen and minor metabolite of estrogen. 4-Hydroxyestradiol is formed from estrogen by the cytochrome P450 isoform CYP1B1. Production of 4-hydroxyestradiol is increased in microsomes prepared from human mammary adenocarcinoma and fibroadenoma microsomes compared with microsomes prepared from non-cancerous tissues. 4-Hydroxyestradiol induces renal tumor formation in male hamsters.


Chemical Structure

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4-Hydroxyestradiol
CAS# 5976-61-4

Theoretical Analysis

MedKoo Cat#: 462967
Name: 4-Hydroxyestradiol
CAS#: 5976-61-4
Chemical Formula: C18H24O3
Exact Mass: 288.1725
Molecular Weight: 288.387
Elemental Analysis: C, 74.97; H, 8.39; O, 16.64

Price and Availability

Size Price Availability Quantity
1.0mg USD 270.0 2 Weeks
5.0mg USD 560.0 2 Weeks
10.0mg USD 950.0 2 Weeks
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Synonym: 4-Hydroxy-17β-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-3,4,17-triol

InChi Key: QOZFCKXEVSGWGS-ZHIYBZGJSA-N

InChi Code: InChI=1S/C18H24O3/c1-18-9-8-11-10-4-6-15(19)17(21)13(10)3-2-12(11)14(18)5-7-16(18)20/h4,6,11-12,14,16,19-21H,2-3,5,7-9H2,1H3/t11-,12-,14+,16+,18+/m1/s1

SMILES Code: C[C@]12[C@]([H])([C@]3([C@@]([H])(C4=CC=C(C(O)=C4CC3)O)CC2)[H])CC[C@@H]1O

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

Preparing Stock Solutions

The following data is based on the product molecular weight 288.387 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

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1: Tang Z, Liu ZH, Wang H, Dang Z, Yin H, Zhou Y, Liu Y. Trace determination of eleven natural estrogens and insights from their occurrence in a municipal wastewater treatment plant and river water. Water Res. 2020 Sep 1;182:115976. doi: 10.1016/j.watres.2020.115976. Epub 2020 May 27. PMID: 32622129.

2: Khan WA, Malik A, Khan MWA. Estrogenization of insulin by catecholestrogen produced high affinity autoantibodies and altered the normal function of insulin in type 1 diabetes. Life Sci. 2020 Sep 1;256:117910. doi: 10.1016/j.lfs.2020.117910. Epub 2020 Jun 3. PMID: 32504753.

3: Miao S, Yang F, Wang Y, Shao C, Zava DT, Ding Q, Shi YE. 4-Hydroxy estrogen metabolite, causing genomic instability by attenuating the function of spindle- assembly checkpoint, can serve as a biomarker for breast cancer. Am J Transl Res. 2019 Aug 15;11(8):4992-5007. PMID: 31497216; PMCID: PMC6731443.

4: Baek HS, Kwon YJ, Ye DJ, Cho E, Kwon TU, Chun YJ. CYP1B1 prevents proteasome- mediated XIAP degradation by inducing PKCε activation and phosphorylation of XIAP. Biochim Biophys Acta Mol Cell Res. 2019 Dec;1866(12):118553. doi: 10.1016/j.bbamcr.2019.118553. Epub 2019 Sep 4. PMID: 31493422.

5: Lanxiang W, Bin W, Ge X, Yutang H, Chunjie W, Honghao Z. Long-term exposure of 4-hydroxyestradiol induces the cancer cell characteristics via upregulating CYP1B1 in MCF-10A cells. Toxicol Mech Methods. 2019 Nov;29(9):686-692. doi: 10.1080/15376516.2019.1650146. Epub 2019 Aug 30. PMID: 31364906.

6: Bozzolino C, Vaglio S, Amante E, Alladio E, Gerace E, Salomone A, Vincenti M. Individual and cyclic estrogenic profile in women: Structure and variability of the data. Steroids. 2019 Oct;150:108432. doi: 10.1016/j.steroids.2019.108432. Epub 2019 Jul 4. PMID: 31279660.

7: Mao X, Wang J, Wang Q, Yang L, Li Y, Lin H, Peng Y, Zheng J. Nitidine Chloride-Induced CYP1 Enzyme Inhibition and Alteration of Estradiol Metabolism. Drug Metab Dispos. 2019 Aug;47(8):919-927. doi: 10.1124/dmd.119.086892. Epub 2019 May 30. PMID: 31147316.

8: Tolba MF, Omar HA, Hersi F, Nunes ACF, Noreddin AM. The impact of Catechol-O- methyl transferase knockdown on the cell proliferation of hormone-responsive cancers. Mol Cell Endocrinol. 2019 May 15;488:79-88. doi: 10.1016/j.mce.2019.03.007. Epub 2019 Mar 21. PMID: 30904591.

9: Ozten N, Vega K, Liehr J, Huang X, Horton L, Cavalieri EL, Rogan EG, Bosland MC. Role of Estrogen in Androgen-Induced Prostate Carcinogenesis in NBL Rats. Horm Cancer. 2019 Jun;10(2-3):77-88. doi: 10.1007/s12672-019-00360-7. Epub 2019 Mar 16. PMID: 30877616; PMCID: PMC6545235.

10: Park SA, Lee MH, Na HK, Surh YJ. Correction: 4-Hydroxyestradiol induces mammary epithelial cell transformation through Nrf2-mediated heme oxygenase-1 overexpression. Oncotarget. 2019 Feb 8;10(12):1266. doi: 10.18632/oncotarget.26681. Erratum for: Oncotarget. 2017 Jan 3;8(1):164-178. PMID: 30815229; PMCID: PMC6383815.

11: An D, Song Z, Yi Y, Zhang Q, Liu J, Zhang Y, Zhou J, Zhao G, Cong D, Li N, Lu Y, Chen X, Zhao D. Oroxylin A, a methylated metabolite of baicalein, exhibits a stronger inhibitory effect than baicalein on the CYP1B1-mediated carcinogenic estradiol metabolite formation. Phytother Res. 2019 Apr;33(4):1033-1043. doi: 10.1002/ptr.6297. Epub 2019 Jan 24. PMID: 30680817.

12: Honda L, Becerra-Herrera M, Richter P. Liquid chromatography-time-of-flight high-resolution mass spectrometry study and determination of the dansylated products of estrogens and their hydroxylated metabolites in water and wastewater. Anal Bioanal Chem. 2018 Dec;410(30):7909-7919. doi: 10.1007/s00216-018-1412-0. Epub 2018 Oct 10. PMID: 30306236.

13: Landeros RV, Pastore MB, Magness RR. Effects of the Catechol and Methoxy Metabolites of 17β-Estradiol on Nitric Oxide Production by Ovine Uterine Artery Endothelial Cells. Reprod Sci. 2019 Apr;26(4):459-468. doi: 10.1177/1933719118783265. Epub 2018 Jun 21. PMID: 29929429; PMCID: PMC6728568.

14: Allam RM, Al-Abd AM, Khedr A, Sharaf OA, Nofal SM, Khalifa AE, Mosli HA, Abdel-Naim AB. Fingolimod interrupts the cross talk between estrogen metabolism and sphingolipid metabolism within prostate cancer cells. Toxicol Lett. 2018 Jul;291:77-85. doi: 10.1016/j.toxlet.2018.04.008. Epub 2018 Apr 11. PMID: 29654831.

15: Buchynska LG, Brieieva OV. Sensitivity to 4-hydroxyestradiol and DNA repair efficiency in peripheral blood lymphocytes of endometrial cancer patients. Exp Oncol. 2018 Mar;40(1):68-72. PMID: 29600983.

16: Sawicka E, Piwowar A, Musiala T, Dlugosz A. THE ESTROGENS / CHROMIUM INTERACTION IN THE NITRIC OXIDE GENERATION. Acta Pol Pharm. 2017 May;74(3):785-791. PMID: 29513947.

17: Cirillo F, Pellegrino M, Malivindi R, Rago V, Avino S, Muto L, Dolce V, Vivacqua A, Rigiracciolo DC, De Marco P, Sebastiani A, Abonante S, Nakajima M, Lappano R, Maggiolini M. GPER is involved in the regulation of the estrogen- metabolizing CYP1B1 enzyme in breast cancer. Oncotarget. 2017 Nov 20;8(63):106608-106624. doi: 10.18632/oncotarget.22541. PMID: 29290975; PMCID: PMC5739760.

18: Takeuchi M, Seki M, Furukawa E, Takahashi A, Saito K, Kobayashi M, Ezoe K, Fukui E, Yoshizawa M, Matsumoto H. Improvement of implantation potential in mouse blastocysts derived from IVF by combined treatment with prolactin, epidermal growth factor and 4-hydroxyestradiol. Mol Hum Reprod. 2017 Aug 1;23(8):557-570. doi: 10.1093/molehr/gax035. PMID: 28810691.

19: Sawicka E, Długosz A. The role of 17β-estradiol metabolites in chromium- induced oxidative stress. Adv Clin Exp Med. 2017 Mar-Apr;26(2):215-221. doi: 10.17219/acem/62217. PMID: 28791837.

20: Wang P, Mills LH, Song JH, Yu J, Zhu BT. Lack of Cell Proliferative and Tumorigenic Effects of 4-Hydroxyestradiol in the Anterior Pituitary of Rats: Role of Ultrarapid O-Methylation Catalyzed by Pituitary Membrane-Bound Catechol- O-Methyltransferase. Chem Res Toxicol. 2017 Jul 17;30(7):1448-1462. doi: 10.1021/acs.chemrestox.7b00096. Epub 2017 Jun 15. PMID: 28616971.