This is a pharmaceutical analytical standard with a high potency and can also be used for cell culture, in vitro, and in vivo applications. It is soluble in DMSO and ethanol at approximately 50 mg/mL.
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:
Molecular Weight:
272.38
EC Number:
MDL number:
UNSPSC Code:
41116107
PubChem Substance ID:
NACRES:
NA.24
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grade
analytical standard
Quality Level
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
Signal Word
Danger
Hazard Statements
Precautionary Statements
Hazard Classifications
Aquatic Chronic 1 - Carc. 2 - Lact. - Muta. 2 - Repr. 1A
Storage Class Code
6.1C - Combustible acute toxic Cat.3 / toxic compounds or compounds which causing chronic effects
WGK
WGK 3
Personal Protective Equipment
dust mask type N95 (US), Eyeshields, Gloves
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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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