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H4637

4-Hydroxyestradiol

Name: 4-Hydroxyestradiol
Brand: SIGMA

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

NACRES:

NA.77

PubChem Substance ID:

24895648

UNSPSC Code:

51111800

MDL number:

MFCD00063335

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Properties

storage temp.

−20°C

Quality Level

100

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)

Description

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.

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pictograms

GHS08

signalword

Warning

hcodes

H351

pcodes

P201 - P202 - P280 - P308 + P313 - P405 - P501

Hazard Classifications

Carc. 2

Storage Class

11 - Combustible Solids

wgk

WGK 3

ppe

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

Regulatory Information

涉药品监管产品

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Effects of 17beta-estradiol, and its metabolite, 4-hydroxyestradiol on fertilization, embryo development and oxidative DNA damage in sand dollar (Dendraster excentricus) sperm.

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

N-acetylcysteine blocks formation of cancer-initiating estrogen-DNA adducts in cells.

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

Keratinocyte growth factor is up-regulated by estrogen in the porcine uterine endometrium and functions in trophectoderm cell proliferation and differentiation.

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

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Global Trade Item Number

SKU	GTIN
H4637-5MG	04061833271483
H4637-1MG	04061833795767