4-Hydroxyestrone
Metabolite of estrone
| IUPAC Name: | (8R,9S,13S,14S)-3,4-Dihydroxy-13-methyl-7,8,9,11,12,14,15,16-octahydro-6H-cyclopenta[a]phenanthren-17-one |
| Other Names: | 4-OHE1 |
| Identifiers | |
| CAS Number | |
| PubChem | 66436 |
| ChemSpider | 59809 |
| SMILES | CC12CCC3C(C1CCC2=O)CCC4=C3C(=C(C=C4)O)O |
| InChI | 1S/C18H22O3/c1-18-7-6-12-11(17(18)8-9-18)3-2-10-4-5-14(20)16(21)15(10)13(12)17/h4-5,12-14,20-21H,2-3,6-9H2,1H3/t12-,13-,14+,17-,18-/m0/s1 |
| InChIKey | YQNWZWMKLDQSAC-ZMSHIADSSA-N |
| StdInChI | |
| StdInChIKey | |
| Properties | |
| Chemical formula | C18H22NO3 |
| Appearance | |
| Density | |
| Melting Point | 255 to 256 °C (491 to 493 °F) |
| Boiling Point | |
| Solubility | |
| Hazards | |
| Main Hazards | |
| Flash Point | |
| Autoignition Temperature | |
4-Hydroxyestrone (4-OHE1) is a metabolite of the estrogen estrone. It is one of the several hydroxylated derivatives of estrone, which include 2-Hydroxyestrone and 16α-Hydroxyestrone.
Biochemistry[edit | edit source]
4-Hydroxyestrone is formed through the hydroxylation of estrone by the enzyme cytochrome P450 1B1 (CYP1B1). This metabolic pathway is part of the estrogen metabolism process, which occurs primarily in the liver and other tissues.
Biological Activity[edit | edit source]
4-Hydroxyestrone has been studied for its potential role in carcinogenesis. It can form catechol estrogens, which may undergo further oxidation to form quinones. These quinones can react with DNA, leading to the formation of DNA adducts and potentially causing mutations that contribute to the development of cancer.
Health Implications[edit | edit source]
The balance between different estrogen metabolites, such as 2-hydroxyestrone and 4-hydroxyestrone, is thought to influence the risk of developing hormone-dependent cancers, such as breast cancer and endometrial cancer. Elevated levels of 4-hydroxyestrone have been associated with an increased risk of these cancers.
Research[edit | edit source]
Ongoing research is focused on understanding the precise mechanisms by which 4-hydroxyestrone and other estrogen metabolites contribute to cancer risk. This includes studies on the role of genetic polymorphisms in enzymes involved in estrogen metabolism and the impact of environmental factors on these metabolic pathways.
See Also[edit | edit source]
References[edit | edit source]
 | This medical article is a stub. You can help WikiMD by expanding it. |
Search WikiMD
Ad.Tired of being Overweight? Try W8MD's physician weight loss program.
Semaglutide (Ozempic / Wegovy and Tirzepatide (Mounjaro / Zepbound) available.
Advertise on WikiMD
|
WikiMD's Wellness Encyclopedia |
| Let Food Be Thy Medicine Medicine Thy Food - Hippocrates |
Translate this page: - East Asian
中文,
日本,
한국어,
South Asian
हिन्दी,
தமிழ்,
తెలుగు,
Urdu,
ಕನ್ನಡ,
Southeast Asian
Indonesian,
Vietnamese,
Thai,
မြန်မာဘာသာ,
বাংলা
European
español,
Deutsch,
français,
Greek,
português do Brasil,
polski,
română,
русский,
Nederlands,
norsk,
svenska,
suomi,
Italian
Middle Eastern & African
عربى,
Turkish,
Persian,
Hebrew,
Afrikaans,
isiZulu,
Kiswahili,
Other
Bulgarian,
Hungarian,
Czech,
Swedish,
മലയാളം,
मराठी,
ਪੰਜਾਬੀ,
ગુજરાતી,
Portuguese,
Ukrainian
Medical Disclaimer: WikiMD is not a substitute for professional medical advice. The information on WikiMD is provided as an information resource only, may be incorrect, outdated or misleading, and is not to be used or relied on for any diagnostic or treatment purposes. Please consult your health care provider before making any healthcare decisions or for guidance about a specific medical condition. WikiMD expressly disclaims responsibility, and shall have no liability, for any damages, loss, injury, or liability whatsoever suffered as a result of your reliance on the information contained in this site. By visiting this site you agree to the foregoing terms and conditions, which may from time to time be changed or supplemented by WikiMD. If you do not agree to the foregoing terms and conditions, you should not enter or use this site. See full disclaimer.
Credits:Most images are courtesy of Wikimedia commons, and templates Wikipedia, licensed under CC BY SA or similar.
Contributors: Prab R. Tumpati, MD
