2-Hydroxyestron

2-Hydroxyestron

Generel
Systematisk navn	( 8R , 9S , 13S , 14S ) -2,3-dihydroxy-13-methyl-7,8,9,11,12,14,15,16-octahydro- 6H - cyclopenta [a]phenanthren-17-on
Forkortelser	2-OHE1
Chem. formel	C18H22O3 _ _ _ _ _
Fysiske egenskaber
Molar masse	286,371 g/ mol
Klassifikation
Reg. CAS nummer	362-06-1
PubChem	440623
Reg. EINECS nummer	636-847-3
SMIL	CC12CCC3C(C1CCC2=O)CCC4=CC(=C(C=C34)O)O
InChI	InChI=1S/C18H22O3/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/h8-9,11-12,14,19-20H,2-7H2,1H3/t11-,12+,14-,18-/m0/s1SWINWPBPEKHUOD-JPVZDGGYSA-N
CHEBI	1156
ChemSpider	389514
Data er baseret på standardbetingelser (25 °C, 100 kPa), medmindre andet er angivet.

2-Hydroxyestron (2-OHE1), også kendt som estra-1,3,5(10)-trien-2,3-diol-17-on , er et naturligt forekommende endogent katekoløstrogen og hovedmetabolitten af østron og østradiol [1] [2] [3] . Det genereres irreversibelt fra østron i leveren og i mindre grad i andre væv via 2-hydroxylering medieret af cytochrom P450-enzymer , primært CYP3A- og CYP1A-underfamilierne [1] [3] . 2-OHE1 er det mest udbredte katekin østrogen i kroppen [3] . Det er ikke signifikant uterotrofisk i bioassays, mens andre hydroxylerede østrogenmetabolitter, herunder 2-hydroxyestradiol, 16α-hydroxyestron, estriol (16α-hydroxyestradiol), 4-hydroxyestradiol, og 4-hydroxyestrone [1] [4] .

Noter

↑ 1 2 3 Oettel, Michael. Østrogener og antiøstrogener I: Fysiologi og virkningsmekanismer for østrogener og antiøstrogener : [ eng. ] / Michael Oettel, Ekkehard Schillinger. - Springer Science & Business Media, 6. december 2012. - S. 227. - ISBN 978-3-642-58616-3 . Arkiveret 15. december 2020 på Wayback Machine
↑ Raquel, David. Integrativ medicin : [ engelsk ] ] . - Elsevier Health Sciences, 2012. - S. 338. - ISBN 1-4377-1793-4 .
↑ 1 2 3 Overgangsalderen : [ eng. ] . - Springer Science & Business Media, 6. december 2012. - S. 64-65. - ISBN 978-1-4612-5525-3 .
↑ Bhavnani BR, Nisker JA, Martin J, Aletebi F, Watson L, Milne JK (2000). "Sammenligning af farmakokinetik af et konjugeret hesteøstrogenpræparat (premarin) og en syntetisk blanding af østrogener (CES) hos postmenopausale kvinder." Journal of the Society for Gynecologic Investigation ]. 7 (3): 175-183. DOI : 10.1016/s1071-5576(00)00049-6 . PMID 10865186 .

Steroide hormoner (endogene)

Hepatosteroider
( lever )

(S-30: Lanostanes )	Lanosterol
(S-27: Cholestans )	Zymosterol → 7-Dehydrodesmosterol → Desmosterol → Kolesterol
Galdesyrer (C-24: Cholaner )	Cholinsyre • Chenodeoxycholsyre • ‎ Deoxycholsyre • ‎ Lithocholsyre • ‎ Glycocholsyre • ‎ Glycochenodeoxycholsyre • ‎ Taurocholsyre • ‎ Taurochenodeoxycholsyre

Gonadosteroider
( gonader )

Gestogener (C-21: Pregnanes )	17α-AC: Epipregnenolon → Epiprogesteron → Epiallopregnandione → Epiallopregnanolon 17-AC: 17-Pregnenolon → 17-Progesteron → 17-Allopregnanedion → 17-Allopregnanolon 17β-AC: Pregnenolon → Progesteron → Allopregnanedion → Allopregnanolon
Androgener (C-19: Androstanes )	17α-OH: Epiandrostenediol → Epitestosteron → 5α-Dihydroepitestosteron → Epiandrostenediol 17-O: Dehydroepiandrosteron → Androstenedion → Androstenedion → Androsteron 17β-OH: Androstenediol → Testosteron → 5α-Dihydrotestosteron → Androstenediol
Østrogener (C-18: Estranes )	17α-OH: Epiestradiol → Epiestriol → Epiestretrol 17-O: Estron → Estradiolon → Estriolon 17β-OH: Østradiol → Estriol → Estetrol

Adrenosteroider
( binyrerne )

Glumerosteroider (C-21: Pregnanes )	Mineralokortikoider 11-Deoxycorticosteron → Corticosteron → 5α-Dihydrocorticosteron → 3α,5α-Tetrahydrocorticosteron Aldosteron → 5α-dihydroaldosteron → 3α,5α-Tetrahydroaldosteron 5α-Dihydrodeoxycorticosteron → 3α,5α-Tetrahydrodeoxycorticosteron Glukokortikoider 11-Deoxycortisol → Cortisol → 5α-Dihydrocortisol → 3α,5α-Tetrahydrocortisol Cortison → 5α-dihydrocortison → 3α,5α-Tetrahydrocortison 5α-Dihydrodeoxycortisol → 3α,5α-Tetrahydrodeoxycortisol
Fascillosteroider (C-19: Androstanes )	11a-hydroxy 17α-OH: 11α-Hydroxyepiandrostanediol → 11α-Hydroxyepiandrostanediol → 5α-dihydro-11α-hydroxyepistosteron → 11α-hydroxyepiandrostanediol 17-O: 11α-hydroxydehydroepiandrosteron → 11α-hydroxyandrostenedion → 11α-hydroxyandrostenedion → 11α-hydroxyandrostenedion 17β-OH: 11α-hydroxyandrostenediol → 11α-hydroxytestosteron → 5α-dihydro-11α-hydroxytestosteron → 11α-hydroxyandrostenediol 11-keto 17α-OH: 11-ketoepiandrostanediol → 11-ketoepistosteron → 5α-dihydro-11-ketoepitestosteron → 11-ketoepiandrostanediol 17-O: 11-ketodehydroepiandrosteron → 11-ketoandrostenedion → 11-ketoandrostenedion → 11-ketoandrostenedion 17β-OH: 11-ketoandrostenediol → 11-ketotestosteron → 5α-dihydro-11-ketotestosteron → 11-ketoandrostenediol 11β-hydroxy 17α-OH: 11β-hydroxyepiandrostanediol → 11β-hydroxyepitaestosteron → 5α-dihydro-11β-hydroxyepitaestosteron → 11β-hydroxyepiandrostanediol 17-O: 11β-hydroxydehydroepiandrosteron → 11β-hydroxyandrostenedion → 11β-hydroxyandrostenedion → 11β-hydroxyandrostenedion 17β-OH: 11β-hydroxyandrostendiol → 11β-hydroxytestosteron → 5α-dihydro-11β-hydroxytestosteron → 11β-hydroxyandrostenediol
Retikulosteroider (C-18: Estranes )	Katekol-østrogener 17α-OH: 2-Hydroxyepiestradiol og 4-Hydroxyepiestradiol 17-O: 2-Hydroxyestron og 4-Hydroxyestron 17β-OH: 2-hydroxyestradiol og 4-hydroxyestradiol Quinon-østrogener 17α-OH: 2,3-quinonepiestradiol og 4,3-quinonepiestradiol 17-O: 2,3-quinonestron og 4,3-quinonestron 17β-OH: 2,3-quinonestradiol og 4,3-quinonestradiol
Medullosteroider	2,3-OH DOPA → Dopamin → Noradrenalin → Adrenalin 3-OH Tryptophan → 5-hydroxytryptophan → Serotonin → N-acetyl-5-hydroxytryptamin → Melatonin 3,4-OH DOPA → Dopamin → Noradrenalin → Adrenalin