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Merck

46542

α-Estradiol

VETRANAL®, analytical standard

Synonym(s):

1,3,5(10)-Estratriene-3,17α-diol, 3,17α-Dihydroxy-1,3,5(10)-estratriene, Epiestradiol

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About This Item

Empirical Formula (Hill Notation):
C18H24O2
CAS Number:
57-91-0
Molecular Weight:
272.38
NACRES:
NA.24
PubChem Substance ID:
329757208
UNSPSC Code:
41116107
EC Number:
200-354-8
MDL number:
MFCD00064144

Key Documents

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grade

analytical standard

Quality Level

200

product line

VETRANAL®

optical activity

[α]/D 52.0 to 56.0°, c = 1 in ethanol

shelf life

limited shelf life, expiry date on the label

technique(s)

HPLC: suitable, gas chromatography (GC): suitable

impurities

≤2.0% water

application(s)

pharmaceutical (small molecule)

format

neat

SMILES string

[H][C@]12CC[C@]3(C)[C@H](O)CC[C@@]3([H])[C@]1([H])CCc4cc(O)ccc24

InChI

1S/C18H24O2/c1-18-9-8-14-13-5-3-12(19)10-11(13)2-4-15(14)16(18)6-7-17(18)20/h3,5,10,14-17,19-20H,2,4,6-9H2,1H3/t14-,15-,16+,17-,18+/m1/s1

InChI key

VOXZDWNPVJITMN-SFFUCWETSA-N

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Application

Refer to the product′s Certificate of Analysis for more information on a suitable instrument technique. Contact Technical Service for further support.

Biochem/physiol Actions

Estradiol (known as alpha Estradiol or 17 alpha Estradiol) is a biologically active estrogen in human breast cancer cells in tissue culture.17-estradiol and its selective receptor, ER-X, are not part of a classical hormone/receptor endocrine system but of a system with important autocrine/paracrine functions in the developing and adult brain. 17-Estradiol may have enormous implications for hormone replacement strategies at the menopause and in the treatment of such neurodegenerative disorders as Alzheimer′s disease and ischemic stroke.

Legal Information

VETRANAL is a registered trademark of Merck KGaA, Darmstadt, Germany

pictograms

Health hazardEnvironment
GHS08,GHS09

signalword

Danger

Hazard Classifications

Aquatic Chronic 1 - Carc. 2 - Lact. - Muta. 2 - Repr. 1A

Storage Class

6.1C - Combustible acute toxic Cat.3 / toxic compounds or compounds which causing chronic effects

wgk

WGK 3

ppe

dust mask type N95 (US), Eyeshields, Gloves

Regulatory Listings

Regulatory Listings are mainly provided for chemical products. Only limited information can be provided here for non-chemical products. No entry means none of the components are listed. It is the user’s obligation to ensure the safe and legal use of the product.

46542-BULK: + 46542-1EA: + 46542-100MG: + 46542-VAR:

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Certificates of Analysis (COA)

Lot/Batch Number
BCCM4656
BCCK0794
BCCJ7405
BCCF6020
BCCF4842

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C Y Cheng et al.
Fertility and sterility, 32(5), 566-570 (1979-11-01)
In modified Tyrode's solution, 17 beta-estradiol at concentrations between 0.1 microgram/ml and 320 nmoles/ml was effective in increasing human spermatozoal forward migration. 17 alpha-Estradiol, although structurally similar to 17 beta-estradiol, had no effect on human spermatozoal motility. DL-Norgestrel at concentrations
J Pitt et al.
Journal of inherited metabolic disease, 25(2), 83-88 (2002-07-18)
Three patients with ketosis had increased excretion of 3-hydroxyglutarate (21.8-37.9 micromol/mmol creatinine; controls 2.3 +/- 1.6), an indicator of glutaryl-CoA dehydrogenase deficiency (GDHD), which normalized when the patients were nonketotic. Clinical assessment of all three patients and enzyme studies in
Cristian G Bologa et al.
Nature chemical biology, 2(4), 207-212 (2006-03-08)
Estrogen is a hormone critical in the development, normal physiology and pathophysiology of numerous human tissues. The effects of estrogen have traditionally been solely ascribed to estrogen receptor alpha (ERalpha) and more recently ERbeta, members of the soluble, nuclear ligand-activated
Edith Bellavance et al.
Journal of medicinal chemistry, 52(23), 7488-7502 (2009-09-24)
17beta-Hydroxysteroid dehydrogenase type 7 (17beta-HSD7) catalyzes the reduction of estrone (E(1)) into estradiol (E(2)) and of dihydrotestosterone (DHT) into 5alpha-androstane-3beta,17beta-diol (3beta-diol), therefore modulating the level of mitogenic estrogens and androgens in humans. By classical and parallel chemistry, we generated several

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