17alpha-Estradiol

Names

[ CAS No. ]:
57-91-0

[ Name ]:
17alpha-Estradiol

[Synonym ]:
α-Estradiol
a-Estradiol
Oestra-1,3,5(10)-triene-3,17α-diol
alfatradiol
MFCD00064144
(17a)-Estra-1,3,5(10)-triene-3,17-diol
3,17α-Dihydroxyestra-1,3,5(10)-triene
Estra-1,3,5(10)-triene-3,17-diol, (17α)-
trans-4-Hydroxycrotonic acid
Epiestradiol
Epiestrol
Estra-1,3,5(10)-triene-3,17a-diol
3,17-α-Dihydroxyoestra-1,3,5(10)-triene
(17α)-Estra-1,3,5(10)-triene-3,17-diol
3,17a-Dihydroxyestra-1,3,5(10)-triene
Oestradiol-17a
3,17a-Dihydroxyoestra-1,3,5(10)-triene
Oestra-1,3,5(10)-triene-3,17a-diol
17-Epiestradiol
17α-Oestradiol
3,17α-Dihydroxyoestra-1,3,5(10)-triene
17a-Estradiol
17α-Estradiol
17α estradiol
Oestradiol-17α
(8R,9S,13S,14S,17R)-13-methyl-6,7,8,9,11,12,14,15,16,17-decahydrocyclopenta[a]phenanthrene-3,17-diol
Epiestradial
Estradiol, 17α-
EINECS 200-023-8
13b-Methyl-1,3,5(10)-gonatriene-3,17a-diol
17a-Oestradiol
17alpha-Estradiol
3,17-Dihydroxyestratriene
Estradiol-17alpha

Biological Activity

[Description]:

Alpha-Estradiol is a weak estrogen and a 5α-reductase inhibitor which is used as a topical medication in the treatment of androgenic alopecia.

[Related Catalog]:

Signaling Pathways >> Metabolic Enzyme/Protease >> 5 alpha Reductase

Natural Products >> Steroids

Research Areas >> Inflammation/Immunology

[Target]

Human Endogenous Metabolite

[In Vitro]

Alpha-Estradiol (17 alpha-Estradiol) is a 5α-reductase inhibitor, and inhibits testosterone metabolism catalyzed by 5 alpha-reductase[1]. Alpha-Estradiol (17 Alpha-estradiol, 10 μM) attenuates LPS-induced inflammatory markers in both C57BL/6J male and female mouse embryonic fibroblast (MEF) cells, primary pre-adipocytes and differentiated 3T3-L1 adipocytes in an ERα-dependent manner, and such effects are through decreased NFκB-p65 and increased ERα protein expression[2].

[In Vivo]

Alpha-Estradiol (17-alpha-estradiol, 0.01, 0.1, 1 μg) significantly reduces the percentage of central avascular/total retina area of the mouse pups. Alpha-Estradiol (1 μg) markedly decreasesmalondialdehyde (MDA) levels on postnatal days (PND) 9, 13, and 17 in retinas of hyperoxia-exposed pups. Alpha-Estradiol (1 μg) also decreases the number of NADPH-oxidase-positive cells, NADPH oxidase concentration and activity in retinas of the pups. In the 1.0-μg Alpha-Estradiol-treated pups, VEGF retinal concentrations are high on PND 9 but lower on PND 14 and 17. The best effect in retinas of 1.0-μg Alpha-Estradiol-treated pups is partly reversed by ICI182780 on PND 14 and 17[3].

[Cell Assay]

Mouse embryonic fibroblast (MEF) cells are treated for the indicated time with Alpha-Estradiol (17 α-E2) or 17 β-E2 at 10 μM concentration. Inflammation is induced by LPS at a concentration of 10 ng/mL either alone or in combination with the respective estrogen[2].

[Animal admin]

Newborn mice are randomLy assigned to six groups according to the kind of treatment: room air with vehicle injection (control, group 1), hyperoxia with vehicle injection (control, group 2), hyperoxia with 0.01 μg Alpha-Estradiol injection (group 3), hyperoxia with 0.1 μg Alpha-Estradiol injection (group 4), hyperoxia with 1.0 μg Alpha-Estradiol injection (group 5), and hyperoxia with 1.0 μg Alpha-Estradiol and 10.0 μg ICI182780 injection (antagonist of estrogen receptor α and β) (group 6). The pups receive daily subcutaneous injections of either Alpha-Estradiol in vehicle [dissolved in ethanol and diluted in 0.05 mL/mouse of phosphate-buffered saline (PBS)] or vehicle alone from postnatal days (PND) 7-16. On PND 7, the pups in the hyperoxia and Alpha-Estradiol-treatment groups are exposed to hyperoxia (75 ± 2 % O2) for 5 days (PND 7-12) and then returned to normoxia (room air) for 5 days, along with the nursing mothers, whereas pups in the normoxia group are kept in normoxia from PND 7-17. The pups are humanely euthanized on PND 9, 13 (14), and 17[3].

[References]

[1]. Schriefers H, et al. Inhibition of testosterone metabolism by 17-alpha-estradiol in rat liver slices. Arzneimittelforschung. 1991 Nov;41(11):1186-9.

[2]. Santos RS, et al. The effects of 17 alpha-estradiol to inhibit inflammation in vitro. Biol Sex Differ. 2017 Sep 6;8:30.

[3]. Zhang HB, et al. 17-Alpha-estradiol ameliorating oxygen-induced retinopathy in a murine model. Jpn J Ophthalmol. 2012 Jul;56(4):407-15.

[Related Small Molecules]

Chemical & Physical Properties

[ Density]:
1.2±0.1 g/cm3

[ Boiling Point ]:
445.9±45.0 °C at 760 mmHg

[ Melting Point ]:
176-180ºC(lit.)

[ Molecular Formula ]:
C₁₈H₂₄O₂

[ Molecular Weight ]:
272.382

[ Flash Point ]:
209.6±23.3 °C

[ Exact Mass ]:
272.177643

[ PSA ]:
40.46000

[ LogP ]:
4.13

[ Vapour Pressure ]:
0.0±1.1 mmHg at 25°C

[ Index of Refraction ]:
1.599

[ Storage condition ]:
0-6°C

[ Water Solubility ]:
ethanol: 50 mg/mL, clear, colorless

MSDS

Click to get detail MSDS

Toxicological Information

CHEMICAL IDENTIFICATION

RTECS NUMBER :: KG3750000

CHEMICAL NAME :: 17-alpha-Estradiol

CAS REGISTRY NUMBER :: 57-91-0

BEILSTEIN REFERENCE NO. :: 2698044

LAST UPDATED :: 199803

DATA ITEMS CITED :: 2

MOLECULAR FORMULA :: C18-H24-O2

MOLECULAR WEIGHT :: 272.42

WISWESSER LINE NOTATION :: L E5 B666TTT&J E1 FQ OQ 17-ALPHA

HEALTH HAZARD DATA

ACUTE TOXICITY DATA

TYPE OF TEST :: TDLo - Lowest published toxic dose

ROUTE OF EXPOSURE :: Intramuscular

SPECIES OBSERVED :: Rodent - guinea pig

DOSE/DURATION :: 3 mg/kg

TOXIC EFFECTS :: Tumorigenic - equivocal tumorigenic agent by RTECS criteria Reproductive - Tumorigenic effects - uterine tumors

MUTATION DATA

TYPE OF TEST :: DNA inhibition

TEST SYSTEM :: Human Cells - not otherwise specified

DOSE/DURATION :: 100 mg/L

REFERENCE :: JTEHD6 Journal of Toxicology and Environmental Health. (Hemisphere Pub., 1025 Vermont Ave., NW, Washington, DC 20005) V.1- 1975/76- Volume(issue)/page/year: 10,143,1982

Safety Information

[ Symbol ]:

GHS08

[ Signal Word ]:
Warning

[ Hazard Statements ]:
H351

[ Precautionary Statements ]:
P281

[ Personal Protective Equipment ]:
dust mask type N95 (US);Eyeshields;Gloves

[ Hazard Codes ]:
Xn: Harmful;

[ Risk Phrases ]:
R40;R48

[ Safety Phrases ]:
53-45-24/25-22

[ RIDADR ]:
UN 2811

[ WGK Germany ]:
3

[ RTECS ]:
KG3750000

Synthetic Route

Click to get detail synthetic route

Precursor & DownStream

Precursor

DownStream

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