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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

signalword

Warning

hcodes

H351

Hazard Classifications

Carc. 2

Storage Class

11 - Combustible Solids

wgk_germany

WGK 3

ppe

Eyeshields, Gloves, type P3 (EN 143) respirator cartridges

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Muhammad Zahid et al.
Free radical biology & medicine, 49(3), 392-400 (2010-05-18)
Catechol estrogens, especially 4-hydroxylated metabolites of 17beta-estradiol (E(2)), are responsible for estrogen-induced carcinogenesis. 4-Hydroxyestradiol (4-OHE(2)), a major metabolite of E(2) formed preferentially by cytochrome P-450 1B1, is oxidized to E(2)-3,4-quinone, which can react with DNA to yield the depurinating adducts
Mary Ann Rempel et al.
The Science of the total environment, 407(7), 2209-2215 (2009-01-28)
Oxidative compounds have been demonstrated to decrease the fertilization capability and viability of offspring of treated spermatozoa. As estrogen and its hydroxylated metabolites readily undergo redox cycling, this study was undertaken to determine if estrogens and other oxidants could damage
Philip S Crooke et al.
Cancer epidemiology, biomarkers & prevention : a publication of the American Association for Cancer Research, cosponsored by the American Society of Preventive Oncology, 20(7), 1502-1515 (2011-05-26)
Current models of breast cancer risk prediction do not directly reflect mammary estrogen metabolism or genetic variability in exposure to carcinogenic estrogen metabolites. We developed a model that simulates the kinetic effect of genetic variants of the enzymes CYP1A1, CYP1B1
H Ka et al.
Endocrinology, 142(6), 2303-2310 (2001-05-18)
Keratinocyte growth factor (KGF) is expressed by uterine endometrial epithelial cells during the estrous cycle and during pregnancy in pigs, whereas KGF receptor is expressed in conceptus trophectoderm and endometrial epithelia. In particular, KGF expression in the endometrium is highest
Sibele I Meireles et al.
Cancer prevention research (Philadelphia, Pa.), 3(6), 707-717 (2010-06-03)
Lung cancer is the leading cause of cancer deaths in the United States, surpassing breast cancer as the primary cause of cancer-related mortality in women. The goal of the present study was to identify early molecular changes in the lung
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