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46542

Supelco

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
EC Number:
200-354-8
MDL number:
MFCD00064144
UNSPSC Code:
41116107
PubChem Substance ID:
329757208
NACRES:
NA.24

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

Signal Word

Danger

Hazard Statements

H341,H351,H360F,H362,H410

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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Certificates of Analysis (COA)

Lot/Batch Number
BCCM4656
BCCK0794
BCCJ7405
BCCF6020
BCCF4842

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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
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
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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