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
Show more names
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
- Formal charge
- 0
- Complexity
- 418
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℃
- storage temp.
- room temp
- solubility
- Chloroform (Slightly), Dioxane (Slightly), Ethanol (Slightly), Methanol (Slightly)
- form
- Crystalline Powder or Crystals
- pka
- 10.77 · pKa 10.77±0.02(H2O)(Approximate)
- color
- White to almost white
- Water Solubility
- 0.03 g/L · 0.03 g/L
- Merck
- 3708 · 3708
- BRN
- 1915077 · 1915077
- Henry's Law Constant
- 2.6 · 2.6×104 mol/(m3Pa) at 25℃, HSDB (2015)
- Major Application
- pharmaceuticalpharmaceutical small molecule
- InChI
- 1S/C18H22O2/c1-18-9-8-14-13-5-3-12(19)10-11(13)2-4-15(14)16(18)6-7-17(18)20/h3,5,10,14-16,19H,2,4,6-9H2,1H3/t14-,15-,16+,18+/m1/s1
- InChIKey
- DNXHEGUUPJUMQT-CBZIJGRNSA-N
- SMILES
- C[C@]12CC[C@H]3[C@@H](CCc4cc(O)ccc34)[C@@H]1CCC2=O
- FDA 21 CFR
- 310.545 · 310.545
- CAS DataBase Reference
- 53 · 53-16-7(CAS DataBase Reference)
- EWG's Food Scores
- 3 · 3-6
- FDA UNII
- 2 DI9HA706A · 2DI9HA706A
- Proposition 65 List
- Estrone
- ATC code
- 3 CA07,G03CC04 · G03CA07,G03CC04
- NIST Chemistry Reference
- 3 · 3-Hydroxyestra-1,3,5(10)-trien-17-one(53-16-7)
- EPA Substance Registry System
- Estrone (53-16-7)
- UNSPSC Code
- 41116107 · 41116107
- NACRES
- 24 · NA.24
- Symbol(GHS)
- 8 · GHS08
- Signal word
- Danger
- Hazard statements
- 351 · H351-H360FD-H362
- Precautionary statements
- 202 · P202-P260-P263-P264-P270-P308+P313
- Hazard Codes
- T,F
- Risk Statements
- 45 · 45-60-61-64-40-63-39/23/24/25-23/24/25-11
- Safety Statements
- 53 · 53-45-36/37-16
- RIDADR
- 1230 · UN1230 - class 3 - PG 2 - Methanol, solution
- WGK Germany
- 3 · 3
- RTECS
- 8575000 · KG8575000
- TSCA
- TSCA listed
- HS Code
- 29335995 · 29335995
- Storage Class
- 6.1 D · 6.1D - Non-combustible acute toxic Cat.3toxic hazardous materials or hazardous materials causing chronic effects
- Hazard Classifications
- 2 Lact.Repr · Carc. 2Lact.Repr. 1A
- Hazardous Substances Data
- 53 · 53-16-7(Hazardous Substances Data)
- REACH Registrations
- Active
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
- Signal word
- Danger
- Symbol(GHS)
- GHS08
- hazard_code
- T,F
- safety_code
- 53-45-36/37-16
- Storage Class
- 6.1D - Non-combustible acute toxic Cat.3toxic hazardous materials or hazardous materials causing chronic effects
- Hazard statements
- H351-H360FD-H362
- REACH Registrations
- Active
- Hazard Classifications
- Carc. 2Lact.Repr. 1A
- Precautionary statements
- P202-P260-P263-P264-P270-P308+P313
- Hazardous Substances Data
- 53-16-7(Hazardous Substances Data)
Chemistry & industry
Applications
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.
Upstream & downstream products
Upstream raw materials
Downstream products
Suppliers50 total
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
Linked notes
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