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H6012

Sigma-Aldrich

4-Hydroxyestrone

≥90% (HPLC)

Synonyme(s) :

1,3,5(10)-Estratriene-3,4-diol-17-one

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About This Item

Formule empirique (notation de Hill):
C18H22O3
Numéro CAS:
3131-23-5
Poids moléculaire :
286.37
Numéro MDL:
MFCD00079358
Code UNSPSC :
51111800
ID de substance PubChem :
24895725
Nomenclature NACRES :
NA.77

Stérilité

non-sterile

Niveau de qualité

100

Pureté

≥90% (HPLC)

Forme

powder

Solubilité

methanol: 10 mg/mL, clear, colorless to faintly brownish-yellow

Conditions d'expédition

ambient

Température de stockage

−20°C

Chaîne SMILES 

[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

Clé InChI

XQZVQQZZOVBNLU-QDTBLXIISA-N

Actions biochimiques/physiologiques

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.

Code de la classe de stockage

11 - Combustible Solids

Classe de danger pour l'eau (WGK)

WGK 3

Point d'éclair (°F)

199.9 °F - closed cup

Point d'éclair (°C)

93.3 °C - closed cup

Équipement de protection individuelle

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
Y Chen et al.
Chemical research in toxicology, 13(5), 342-350 (2000-05-17)
Estrogen replacement therapy has been correlated with an increased risk of developing breast or endometrial cancer. 4-Hydroxyequilenin (4-OHEN) is a catechol metabolite of equilenin which is a minor component of the estrogen replacement formulation marketed under the name of Premarin
X Xu et al.
The Journal of clinical endocrinology and metabolism, 84(11), 3914-3918 (1999-11-24)
Endogenous estrogen metabolism may play an important role in the pathogenesis of hormone-related cancers, most notably breast cancer. Despite the importance of estrogen metabolism, little is known about estrogen metabolite profiles during different phases of the menstrual cycle. This study
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