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Merck
CN

H6012

4-Hydroxyestrone

≥90% (HPLC)

Synonym(s):

1,3,5(10)-Estratriene-3,4-diol-17-one

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About This Item

Empirical Formula (Hill Notation):
C18H22O3
CAS Number:
3131-23-5
Molecular Weight:
286.37
NACRES:
NA.77
PubChem Substance ID:
24895725
UNSPSC Code:
51111800
MDL number:
MFCD00079358

Key Documents

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Product Name

4-Hydroxyestrone, ≥90% (HPLC)

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

SMILES string

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

InChI key

XQZVQQZZOVBNLU-QDTBLXIISA-N

sterility

non-sterile

assay

≥90% (HPLC)

form

powder

solubility

methanol: 10 mg/mL, clear, colorless to faintly brownish-yellow

shipped in

ambient

storage temp.

−20°C

Quality Level

100

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

WGK 3

flash_point_f

199.9 °F - closed cup

flash_point_c

93.3 °C - closed cup

ppe

Eyeshields, Gloves, type N95 (US)

Regulatory Information

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Certificates of Analysis (COA)

Lot/Batch Number
MKCR8450
MKCQ7515
MKCP5846
MKCN3557
MKCG7392

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Shelley A Gestl et al.
The American journal of pathology, 160(4), 1467-1479 (2002-04-12)
Glucuronidation, mediated by UDP-glucuronosyltransferases (UGTs), affects the actions and disposition of diverse endo- and xenobiotics. In the case of catecholestrogens (CEs), glucuronidation is likely to block their oxidation to quinone estrogens that are the putative mediators of CEs' actions as
X Han et al.
Carcinogenesis, 16(10), 2571-2574 (1995-10-01)
Free radical generation by metabolic redox cycling between catechol estrogens and their quinones and subsequent hydroxyl radical damage to DNA have been proposed to mediate estrogen-induced renal carcinogenesis in the hamster. In this study the content of 8-hydroxy-2'-deoxy-guanosine (8-OHdG), a
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
B T Zhu et al.
Endocrinology, 135(5), 1772-1779 (1994-11-01)
As part of an ongoing investigation of the role of metabolic activation of estrogens in the genesis of cancers such as estrogen-induced renal tumors in hamsters, we have 1) determined steroid-17 beta-oxidoreductase activity of microsomes and cytosol prepared from hamster
K Tabakovic et al.
Chemical research in toxicology, 7(5), 696-701 (1994-09-01)
Reaction of lysine with estrone 3,4-o-quinone gave a complex mixture of products. Six compounds were isolated and identified using spectroscopic techniques. Among the reaction products isolated were 4-hydroxyestrone (2), 3-aminoisoestrone (3), 3-(N-pentyl-5-amino)-isoestrone (4), 1-lysylestrone 3,4-o-iminoquinone (5), and two dimeric products
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