Synonyms

1,3,5(10)-ESTRATRIEN-3-OL-17-ONE

1,3,5[10]-ESTRATRIENE-3-OL-17-ONE

1,3,5-ESTRATRIEN-3-OL-17-ONE

3beta-hydroxyestra-1,3,5(10)-trien-17-one

3-HYDROXY-1,3,5[10]-ESTRATRIEN-17-ONE

3-HYDROXY-ESTRA-1,3,5(10)-TRIEN-17-ONE

beta-estrone

DELTA1,3,5(10)-ESTRATRIEN-3-OL-17-ONE

DESTRONE

E 1

ESTROL

ESTRONE

FOLLICULIN

KESTRONE

OESTRIN

OESTRONE

OESTRONE (E1)

(8R,13S)-3-Hydroxy-13-methyl-6,7,8,9,11,12,13,14,15,16-decahydro-cyclopenta[a]phenanthren-17-one

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

1,3,5-Oestratrien-3-ol-17-one

CAS:53-16-7

MF:C18H22O2

MW:270.37

EINECS:200-164-5

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

Hazard Codes

Risk Statements 

Safety Statements 

RIDADR 

UN1230 - class 3 - PG 2 - Methanol, solution

WGK Germany 

RTECS 

KG8575000

HS Code 

29335995

Hazardous Substances Data

Chemical Properties

Crystalline Solid

Chemical Properties

Estrone is an odorless white crystalline powder.

Originator

Estrone,Abbott

Uses

Estrone is a metabolite of 17β-Estradiol (E888000).
During the metabolism, it is in rapid equilibrium with Estriol (E888960) and 17β-Estradiol (E888000) (1).
Causes the feminization of male fish at human and animal waste sites (2).
This compound is a contaminant of emerging concern (CECs).
Drinking water contaminant candidate list 3 (CCL 3) compound as per United States Environmental Protection Agency (EPA), environmental, and food contaminants.

Uses

A metabolite of 17β-Estradiol.

Uses

estrogen

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.

Manufacturing Process

1-Vinyl-1,2,3,4-tetrahydronaphthalene-1,6-diol reacts with 2- methylcyclopentane-1,3-dione in the presence of Triton B in tert-butanol gives a good yield of δ1,3,5(10),9(11)-8,14-secoestratetraen-3-ol-14,17-dione, melting point 124°-126°C (from methanol).
δ1,3,5(10),9(11)-8,14-Secoestratetraen-3-ol-14,17-dione under influence of hydrochloric acid in tetrahydrofurane cyclises into δ1,3,5(10),8,14-estrapentaen- 3-ol-17-one, melting point 216°-218°C.
δ1,3,5(10),8,14-Estrapentaen-3-ol-17-one is converted to d,l-8-dehydroestrone by selective hydrogenation with hydrogen, melting point 251°-254°C (from methanol). Exhaustive hydrogenation of δ1,3,5(10),8,14-estrapentaen-3-ol-17- one give d,l-8-isoestrone.
d,l-8-Isoestrone in the presence of hydrochloric acid in tetrahydrofurane isomerizes into d,l-9(11)-dehydroestrone, melting point 262°-265°C (from alcohol).
Hydrogenation of d,l-9(11)-dehydroestrone in tetrahydrofuran in the presence of Pd/CaCO3 yields the estrone, melting point 251°-252°C (from acetone).

Brand name

Estrogenic Substance (Wyeth); Theelin (Parkdale).

Therapeutic Function

Estrogen

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.

Raw materials

Preparation Products