Skip to Content
Merck
All Photos(1)

Documents

H4637

Sigma-Aldrich

4-Hydroxyestradiol

Synonym(s):

1,3,5(10)-Estratriene-3,4,17β-triol

Sign Into View Organizational & Contract Pricing


About This Item

Empirical Formula (Hill Notation):
C18H24O3
CAS Number:
Molecular Weight:
288.38
MDL number:
UNSPSC Code:
51111800
PubChem Substance ID:
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)

Looking for similar products? Visit Product Comparison Guide

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

Signal Word

Warning

Hazard Statements

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)

Search for Certificates of Analysis (COA) by entering the products Lot/Batch Number. Lot and Batch Numbers can be found on a product’s label following the words ‘Lot’ or ‘Batch’.

Already Own This Product?

Find documentation for the products that you have recently purchased in the Document Library.

Visit the Document Library

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
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
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
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

Our team of scientists has experience in all areas of research including Life Science, Material Science, Chemical Synthesis, Chromatography, Analytical and many others.

Contact Technical Service