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H4637

Sigma-Aldrich

4-Hydroxyestradiol

Synonym(s):

1,3,5(10)-Estratriene-3,4,17β-triol

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About This Item

Empirical Formula (Hill Notation):
C18H24O3
CAS Number:
5976-61-4
Molecular Weight:
288.38
MDL number:
MFCD00063335
UNSPSC Code:
51111800
PubChem Substance ID:
24895648
NACRES:
NA.77

storage temp.

−20°C

SMILES string

[H][C@]12CC[C@]3(C)[C@@H](O)CC[C@@]3([H])[C@]1([H])CCc4c(O)c(O)ccc24

InChI

1S/C18H24O3/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/h4,6,11-12,14,16,19-21H,2-3,5,7-9H2,1H3/t11-,12-,14+,16+,18+/m1/s1

InChI key

QOZFCKXEVSGWGS-ZHIYBZGJSA-N

Gene Information

human ... ESR1(2099)
rat ... Ar(24208)

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Biochem/physiol Actions

4-Hydroxyestradiol, an metabolite of estradiol, forms adducts with adenine (N3) and guanine (N7) by depurinating sites in DNA of cultured human breast epithelial cells. This effect may play an important role in malignant transformation of these cells.

Pictograms

Health hazard
GHS08

Signal Word

Warning

Hazard Statements

H351

Hazard Classifications

Carc. 2

Storage Class Code

11 - Combustible Solids

WGK

WGK 3

Personal Protective Equipment

dust mask type N95 (US), Eyeshields, Gloves

Certificates of Analysis (COA)

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Richard Santen et al.
Annals of the New York Academy of Sciences, 1155, 132-140 (2009-03-03)
Long-term exposure to estrogens influences the development of breast cancer in women, but the precise mechanisms involved are not clearly defined. Our working hypothesis is that estrogen modulates this process by two separate processes. One involves the binding of estradiol
Sin-Aye Park et al.
Cancer research, 69(6), 2416-2424 (2009-03-12)
Estrogen is converted by cytochrome P450 1B1 to 4-hydroxyestradiol (4-OHE(2)), a putative carcinogenic metabolite of estrogen. This catechol estrogen metabolite is oxidized further to produce a reactive quinone via semiquinone. Redox cycling between 4-OHE(2) and its quinoid generates reactive oxygen
Wahid Ali Khan et al.
Journal of clinical immunology, 31(1), 22-29 (2010-09-04)
Increased concentrations of estrogen metabolites (catecholestrogens) have been found in rheumatoid arthritis (RA) but the exact patho-etiology remains elusive. The binding of antibodies from the sera of RA patients and control subjects to native and modified DNA was studied by
Susana Lin et al.
Lung cancer (Amsterdam, Netherlands), 75(3), 285-292 (2011-09-17)
Women have a higher risk of lung adenocarcinoma than men, suggesting that estrogen pathway may be involved in the pathogenesis of this cancer. This study was designed to determine whether ERα expression, estrogen levels, and endocrine disruptor exposure would influence
Sin-Aye Park et al.
Free radical research, 46(8), 1051-1057 (2012-05-11)
Excess estrogen stimulates the proliferation of mammary epithelial cells and hence represents a major risk factor for breast cancer. Estrogen is subjected to cytochrome P450-catalysed oxidative metabolism to produce an oncogenic catechol estrogen, 4-hydroxyestradiol (4-OHE₂). 4-OHE₂ undergoes redox cycling during
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