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H6012

Sigma-Aldrich

4-Hydroxyestrone

≥90% (HPLC)

Sinônimo(s):

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

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About This Item

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

esterilidade

non-sterile

Ensaio

≥90% (HPLC)

forma

powder

solubilidade

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

Condições de expedição

ambient

temperatura de armazenamento

−20°C

cadeia de caracteres 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

chave InChI

XQZVQQZZOVBNLU-QDTBLXIISA-N

Ações bioquímicas/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 classe de armazenamento

11 - Combustible Solids

Classe de risco de água (WGK)

WGK 3

Ponto de fulgor (°F)

199.9 °F - closed cup

Ponto de fulgor (°C)

93.3 °C - closed cup

Equipamento de proteção individual

Eyeshields, Gloves, type N95 (US)

Certificados de análise (COA)

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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)
Z Cheng et al.
Toxicological sciences : an official journal of the Society of Toxicology, 45(1), 52-57 (1998-12-16)
Catechol estrogens are major estrogen metabolites in mammals and are the most potent naturally occurring inhibitors of catecholamine metabolism. These estrogen compounds have been implicated in carcinogenic activity and the 4/2-hydroxyestradiol concentration has been shown to be elevated in neoplastic
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 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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