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Key Documents

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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
MDL number:
MFCD00079358
UNSPSC Code:
51111800
PubChem Substance ID:
24895725
NACRES:
NA.77

sterility

non-sterile

Quality Level

100

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_germany

WGK 3

flash_point_f

199.9 °F - closed cup

flash_point_c

93.3 °C - closed cup

ppe

Eyeshields, Gloves, type N95 (US)

Certificados de análisis (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)
Menopause: Biology and Pathobiology (2000)
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
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
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