H6012
4-Hydroxyestrone
≥90% (HPLC)
Synonym(s):
1,3,5(10)-Estratriene-3,4-diol-17-one
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About This Item
Empirical Formula (Hill Notation):
C18H22O3
CAS Number:
Molecular Weight:
286.37
NACRES:
NA.77
PubChem Substance ID:
UNSPSC Code:
51111800
MDL number:
sterility
non-sterile
Quality Level
assay
≥90% (HPLC)
form
powder
solubility
methanol: 10 mg/mL, clear, colorless to faintly brownish-yellow
shipped in
ambient
storage temp.
−20°C
SMILES string
[H][C@]12CC[C@]3(C)C(=O)CC[C@@]3([H])[C@]1([H])CCc4c(O)c(O)ccc24
InChI
1S/C18H22O3/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/h4,6,11-12,14,19,21H,2-3,5,7-9H2,1H3/t11-,12-,14+,18+/m1/s1
InChI key
XQZVQQZZOVBNLU-QDTBLXIISA-N
Biochem/physiol Actions
4-Hydroxyestrone is an endogenous estrogen metabolite, which exhibits a strong neuroprotective effect against oxidative damage. It also provides effective protection against kanic acid-induced hippocampal oxidative damage in rats when compared to 17β-estradiol. 4-Hydroxyestrone regulates the angiogenic process during corpus luteum formation. It might be involved in an increased risk of cancer. 4-Hydroxyestrone is found in the early and mid-luteal phases.
Storage Class
11 - Combustible Solids
wgk
WGK 3
flash_point_f
199.9 °F - closed cup
flash_point_c
93.3 °C - closed cup
ppe
Eyeshields, Gloves, type N95 (US)
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Y Markushin et al.
Chemical research in toxicology, 16(9), 1107-1117 (2003-09-16)
Estrogens, including the natural hormones estrone (E(1)) and estradiol (E(2)), are thought to be involved in tumor induction. Catechol estrogen quinones (CEQ) derived from 4-hydroxyestrone (4-OHE(1)) and 4-hydroxyestradiol (4-OHE(2)) react with DNA and form depurinating N7Gua and N3Ade adducts that
X Han et al.
Carcinogenesis, 16(10), 2571-2574 (1995-10-01)
Free radical generation by metabolic redox cycling between catechol estrogens and their quinones and subsequent hydroxyl radical damage to DNA have been proposed to mediate estrogen-induced renal carcinogenesis in the hamster. In this study the content of 8-hydroxy-2'-deoxy-guanosine (8-OHdG), a
Shelley A Gestl et al.
The American journal of pathology, 160(4), 1467-1479 (2002-04-12)
Glucuronidation, mediated by UDP-glucuronosyltransferases (UGTs), affects the actions and disposition of diverse endo- and xenobiotics. In the case of catecholestrogens (CEs), glucuronidation is likely to block their oxidation to quinone estrogens that are the putative mediators of CEs' actions as