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H6012

Sigma-Aldrich

4-Hydroxyestrone

≥90% (HPLC)

Sinónimos:

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

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About This Item

Fórmula empírica (notación de Hill):
C18H22O3
Número de CAS:
3131-23-5
Peso molecular:
286.37
Número MDL:
MFCD00079358
Código UNSPSC:
51111800
ID de la sustancia en PubChem:
24895725
NACRES:
NA.77

esterilidad

non-sterile

Nivel de calidad

100

Ensayo

≥90% (HPLC)

Formulario

powder

solubilidad

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

Condiciones de envío

ambient

temp. de almacenamiento

−20°C

cadena 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

Clave InChI

XQZVQQZZOVBNLU-QDTBLXIISA-N

Acciones bioquímicas o fisiológicas

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.

Código de clase de almacenamiento

11 - Combustible Solids

Clase de riesgo para el agua (WGK)

WGK 3

Punto de inflamabilidad (°F)

199.9 °F - closed cup

Punto de inflamabilidad (°C)

93.3 °C - closed cup

Equipo de protección personal

Eyeshields, Gloves, type N95 (US)

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Certificados de análisis (COA)

Lot/Batch Number
MKCR8450
MKCQ7515
MKCP5846
MKCN3557
MKCG7392

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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
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
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
Y Markushin et al.
The Prostate, 66(14), 1565-1571 (2006-08-09)
Catechol estrogen quinones (CEQ) derived from 4-hydroxyestrone (4-OHE1) and 4-hydroxyestradiol (4-OHE2) react with DNA to form depurinating--N7Gua and--N3Ade adducts. This damage leads to mutations that can initiate breast and prostate cancer. To determine whether this damage occurs in humans, urine
Nikola Getoff et al.
Journal of photochemistry and photobiology. B, Biology, 98(1), 20-24 (2009-11-21)
4-Hydroxyestrone (4-OHE(1)), a typical cancer-inducing metabolite, originating from 17beta-estradiol (17beta-E2), was chosen as a model for the studies. The aim was to get a deeper insight in the mechanisms of its ability to initiate cancer. It was found, that 4-OHE(1)
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