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1,3,5(10)-Estratrien-3-ol-17-one

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1,3,5(10)-Estratrien-3-ol-17-one Basic information

Product Name:
1,3,5(10)-Estratrien-3-ol-17-one
CAS:
53-16-7
MF:
C18H22O2
MW:
270.37
EINECS:
200-164-5
Mol File:
53-16-7.mol
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1,3,5(10)-Estratrien-3-ol-17-one Chemical Properties

Melting point:
258-260 °C(lit.)
alpha 
158 º (c=1, dioxane)
Boiling point:
353.48°C (rough estimate)
Density 
1.2360
refractive index 
165 ° (C=1, Dioxane)
Flash point:
9℃
storage temp. 
Refrigerator
pka
pKa 10.77±0.02(H2O)(Approximate)
form 
Crystalline Powder or Crystals
color 
White to almost white
Water Solubility 
0.03 g/L
Merck 
3708
BRN 
1915077
InChIKey
DNXHEGUUPJUMQT-CBZIJGRNSA-N
CAS DataBase Reference
53-16-7(CAS DataBase Reference)
NIST Chemistry Reference
3-Hydroxyestra-1,3,5(10)-trien-17-one(53-16-7)
EPA Substance Registry System
Estrone (53-16-7)
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Safety Information

Hazard Codes 
T,F
Risk Statements 
45-60-61-64-40-63-39/23/24/25-23/24/25-11
Safety Statements 
53-45-36/37-16
RIDADR 
UN1230 - class 3 - PG 2 - Methanol, solution
WGK Germany 
3
RTECS 
KG8575000
HS Code 
29335995
Hazardous Substances Data
53-16-7(Hazardous Substances Data)

MSDS

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1,3,5(10)-Estratrien-3-ol-17-one Usage And Synthesis

Chemical Properties

Crystalline Solid

Chemical Properties

Estrone is an odorless white crystalline powder.

Uses

A metabolite of 17β-Estradiol.

Uses

estrogen

Uses

A metabolite of 17-Estradiol

Definition

ChEBI: A 17-oxo steroid that is estra-1,3,5(10)-triene substituted by an hydroxy group at position 3 and an oxo group at position 17.

brand name

Estrogenic Substance (Wyeth); Theelin (Parkdale).

General Description

Estrone, 3-hydroxyestra-1,3,5(10)-trien-17-one, is less active than estradiol but more active than itsmetabolite, estriol. As the salt of its 3-sulfate ester, estroneis the primary ingredient in conjugated estrogens, USP, andesterified estrogens, USP. Although originally obtainedfrom the urine of pregnant mares (about 10 mg/L), estroneis now prepared synthetically. Estrone itself is not availablein commercial oral formulations, but can be obtained at compounding pharmacies as a topical formulation. Oleoylestrone,the C3 ester of estrone with oleic acid, is in phase IIclinical trials for the treatment of obesity. This acyl estronederivative reduces fat stores by a mechanism not involvingthe ER, although some of the oleoyl-estrone is hydrolyzedto estrone in vivo.

Hazard

A carcinogen (OSHA).

Safety Profile

Confirmed carcinogen with experimental carcinogenic, neoplastigenic, tumorigenic, and teratogenic data. A poison by intraperitoneal and subcutaneous routes. Human reproductive effects by implantation: spermatogenesis and impotence. Mutation data reported. A steroid drug for the treatment of menopause and ovariectomy symptoms. When heated to decomposition it emits acrid smoke and irritating fumes.

Potential Exposure

Synthesized from ergosterol. Used in combination with progestogen as an oral contraceptive.

Shipping

UN3249 Medicine, solid, toxic, n.o.s., Hazard Class: 6.1; Labels: 6.1-Poisonous materials.

Purification Methods

Purify estrone by chromatography on silica gel, eluting with 2:1 hexane/EtOAc and recrystallising from EtOH or Et2O/EtOH. [Danishefsky & Cain J Am Chem Soc 98 4975 1976.] The acetate [901-93-9] crystallises from EtOH with m 125-127o. [Beilstein 8 III 1171.]

Incompatibilities

May react exothermically with reducing agents to generate flammable gaseous hydrogen. Incompatible with oxidizers (chlorates, nitrates, peroxides, permanganates, perchlorates, chlorine, bromine, fluorine, etc.); contact may cause fires or explosions. Keep away from alkaline materials, strong bases, strong acids, oxoacids, and epoxides.

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