Ketohydroxy-Estratriene

HCID 698CAS 53-16-7

Basic information

Standard SMILES
CC12CCC3c4ccc(O)cc4CCC3C1CCC2=O
InChIKey
DNXHEGUUPJUMQT-CBZIJGRNSA-N
Molecular formula
C18H22O2
Average molar mass
270.4 g/mol

Overview

3-hydroxy-13-methyl-7,8,9,11,12,14,15,16-octahydro-6H-cyclopenta[a]phenanthren-17-one is a steroid. It has a role as an estrogen.

Names & identifiers

Preferred name
Ketohydroxy-Estratriene
IUPAC
3-hydroxy-13-methyl-7,8,9,11,12,14,15,16-octahydro-6H-cyclopenta[a]phenanthren-17-one
English name
Estrone
Molecular formula
C18H22O2
Molecular weight
270.37

Names & synonyms

Menformon AE1;Oestrone1187829-63-5FollestrolMestronaqNSC9699Fem-O-GenKetohydroxy-EstratrieneST019426Delta1,3,5(10)-Estratrien-3-ol-17-one3-hydroxy-13-methyl-7,8,9,11,12,14,15,16-octahydro-6H-cyclopenta[a]phenanthren-17-one5-hydroxy-15-methyltetracyclo[8.7.0.0^{2,7}.0^{11,15}]heptadeca-2,4,6-trien-14-one
Show more names
EstronOESTRONE200-164-5EsteroneHiestrone1,3,5(10)-ESTRATRIEN-3-OL-17-ONEESTROL(8R,9S,13S,14S)-3-hydroxy-13-Methyl-7,8,9,11,12,13,15,16-octahydro-6H-cyclopenta[a]phenanthren-17(14H)-oneFOLLICULIN
3-Hydroxy-13-methyl-6,7,8,9,11,12,13,14,15,16-decahydro-17h-cyclopenta[a]phenanthren-17-one5-hydroxy-15-methyltetracyclo[8.7.0.0<2,7>.0<11,15>]heptadeca-2(7),3,5-trien-1 4-oneE(sub 1)FermidynFemestrone inj.NCGC00015423-03Follidrin (tablets)Duogen (Salt/Mix)

Database identifiers

CAS
53-16-7
PubChem CID
698
ChEMBL
CHEMBL756
ChEBI
CHEBI:95131

Properties

Computed structural properties

XLogP
3.1
Topological polar surface area
37.3 Ų
Hydrogen bond donors
1
Hydrogen bond acceptors
2
Rotatable bonds
0
Heavy atoms
20

Physicochemical properties

Melting point
258 · 258-260 °C(lit.)
alpha
158 · 158 º (c=1, dioxane)
Boiling point
353.48 °C · 353.48°C (rough estimate)
Density
1.236 · 1.2360
refractive index
165 ° · 165 ° (C=1, Dioxane)
Flash point
9 ℃ · 9℃

Safety & regulation

Safety data

wgk
3
tsca
TSCA listed
rtecs
KG8575000
ridadr
UN1230 - class 3 - PG 2 - Methanol, solution
hs_code
29335995
risk_code
45-60-61-64-40-63-39/23/24/25-23/24/25-11

Chemistry & industry

Applications · 5 items

DescriptionEstrone is one of the three naturally occurring estrogens, the others being estradiol and estriol. Estrone is synthesized from androstenedione by the aromatase enzyme system in the ovaries and placenta, and is also synthesized from estradiol by 17-hydroxy steroid dehydrogenase in the liver.Serum concentrations of estrone in premenopausal women fluctuate according to the menstrual cycle and becomes the most predominant estrogen in postmenopausal women.The binding affinities of estrone to the estrogen receptors α and β are approximately 60% and 37% relative to estradiol.

UsesEstrone 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.

UsesA metabolite of 17β-Estradiol.

UsesEstrone is a weak form of estrogen and exists as estrone sulphate. Estrone is a luteolytic estrogen produced by the corpus luteum. In the follicle, estrone is synthesized from androstenedione by the action of cytochrome P450 aromatase.Estrone has been used:as medium supplement for hormone based degranulation studies of natural killer cells.as an endocrine disrupting compound for screening bacterial biosensor in toxic water.as medium component for monitoring fatty acid synthase (FASN) activity in breast adenocarcinoma cell lines.

General DescriptionEstrone, 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.

Suppliers50 total

国药集团化学试剂有限公司86-21-63210123 · [email protected]
北京华美互利生物化工010-56205725 · [email protected]
梯希爱(上海)化成工业发展有限公司021-67121386 · [email protected]
上海阿拉丁生化科技股份有限公司400-6206333 13167063860 · [email protected]
T&W GROUP021-61551611 13296011611 · [email protected]

Additional notes

DefinitionChEBI: 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.

Related reactions

14 records

Linked notes

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