11β-Hydroxyandrostenedione
Steroid hormone
| IUPAC Name: | (8R,9S,10R,13S,14S)-10,13-dimethyl-2,6,7,8,9,11,12,14,15,16-decahydro-1H-cyclopenta[a]phenanthrene-3,17-dione |
| Other Names: | 11β-Hydroxyandrost-4-ene-3,17-dione |
| Identifiers | |
| CAS Number | |
| PubChem | 91450 |
| ChemSpider | 82568 |
| SMILES | O=C4C[C@H]3[C@@H](CC[C@]2([C@H]3CC[C@@H]2[C@@H]1CCC(=O)C=C1)C)C4O |
| InChI | |
| InChIKey | |
| StdInChI | 1S/C19H26O3/c1-18-9-7-12(20)10-11(18)2-3-13-14-4-5-16(21)19(14,3)8-6-15(13)17(18)22/h10,13-15,17,22H,2-9H2,1H3/t13-,14-,15-,17-,18-,19-/m0/s1 |
| StdInChIKey | YQHBGGKJXHFGFY-XMUHMHRVSA-N |
| Properties | |
| Chemical formula | C19H26NO3 |
| Appearance | |
| Density | |
| Melting Point | |
| Boiling Point | |
| Solubility | |
| Hazards | |
| Main Hazards | |
| Flash Point | |
| Autoignition Temperature | |
11β-Hydroxyandrostenedione (11β-OHA4) is a steroid hormone and an intermediate in the biosynthesis of corticosteroids such as cortisol and corticosterone. It is produced from androstenedione by the enzyme 11β-hydroxylase in the adrenal cortex.
Biosynthesis[edit | edit source]
11β-Hydroxyandrostenedione is synthesized from androstenedione through the action of the enzyme 11β-hydroxylase (also known as CYP11B1). This enzyme is located in the mitochondria of adrenal cortex cells. The conversion involves the hydroxylation of the 11th carbon of the androstenedione molecule.
Function[edit | edit source]
11β-Hydroxyandrostenedione serves as a precursor for the synthesis of corticosteroids, including cortisol and corticosterone. These hormones are crucial for various physiological processes, including the regulation of metabolism, immune response, and stress response.
Clinical Significance[edit | edit source]
Abnormal levels of 11β-Hydroxyandrostenedione can be indicative of disorders in steroidogenesis, such as congenital adrenal hyperplasia (CAH). In CAH, mutations in the genes encoding steroidogenic enzymes can lead to the accumulation or deficiency of certain steroid intermediates, including 11β-Hydroxyandrostenedione.
See also[edit | edit source]
References[edit | edit source]
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Contributors: Prab R. Tumpati, MD
