Equilenin
Basic information
- CAS
517-09-9- Standard SMILES
C[C@]12CCc3c(ccc4cc(O)ccc34)[C@@H]1CCC2=O- InChIKey
PDRGHUMCVRDZLQ-WMZOPIPTSA-N- Molecular formula
- C18H18O2
- Average molar mass
- 266.3 g/mol
- Monoisotopic mass
- 266.13067981
Overview
Equilenin is a 3-hydroxy steroid that is estrone which carries two double bonds at positions 6 and 8. It is found in the urine of pregnant mare's and extensively used for estrogen replacement therapy in postmenopausal women. It has a role as an antioxidant and a mammalian metabolite. It is a 17-oxo steroid and a 3-hydroxy steroid.
Names & identifiers
- Preferred name
- Equilenin
- IUPAC
- (13S,14S)-3-hydroxy-13-methyl-12,14,15,16-tetrahydro-11H-cyclopenta[a]phenanthren-17-one
- English name
- EQUILENIN
- Molecular formula
- C18H18O2
- Molecular weight
- 266.33
Names & synonyms
EQUILENIN517-09-9Equilenined-Equilenin(+)-Equilenin3-Hydroxyestra-1,3,5,7,9-pentaen-17-one3-Hydroxyestra-1,3,5(10),6,8-pentaen-17-oneW8FTJ17C4JDTXSID2052156CHEBI:34739NSC-9901Estra-1,3,5,7,9-pentaen-17-one, 3-hydroxy-
Show more names
3-hydroxyoestra-1,3,5(10),6,8-pentaen-17-oneE 400Equileninal-EquileninIsoequilenin
RefChem:591014DTXCID7030725208-230-5(13S,14S)-3-hydroxy-13-methyl-12,14,15,16-tetrahydro-11H-cyclopenta[a]phenanthren-17-one3-hydroxy-estra-1,3,5(10),6,8-pentaen-17-oneNSC 9901(13S,14S)-3-Hydroxy-13-methyl-12,13,15,16-tetrahydro-11H-cyclopenta[a]phenanthren-17(14H)-oneEQU
Database identifiers
- CAS
517-09-9- PubChem CID
- 444865
- DTXSID
DTXSID2052156- ChEMBL
CHEMBL225546- ChEBI
Properties
Computed structural properties
- XLogP
- 3.5
- 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
Experimental & physicochemical properties
Chemical ClassesHormone and(or) waste-water effluent contaminant
DrugsPharmaceuticals -> Listed in ZINC15
LipidsLipids -> Sterol Lipids [ST] -> Steroids [ST02] -> C18 steroids (estrogens) and derivatives [ST0201]
Endocrine DisruptorsPotential endocrine disrupting compound
Physicochemical properties
- Melting point
- 258 · 258-259°
- alpha
- 16 · D16 +87° (12.8 mg made up to 1.8 ml in dioxane)
- Boiling point
- 349.54 °C · 349.54°C (rough estimate)
- Density
- 1.1305 · 1.1305 (rough estimate)
- refractive index
- 1.48 · 1.4800 (estimate)
- Flash point
- 2 °C · 2 °C
- storage temp.
- 2 · 2-8°C
- solubility
- DMSO (Slightly), Methanol (Slightly, Heated)
Safety & regulation
Safety information is for reference only and does not replace the supplier’s Safety Data Sheet (SDS), applicable regulations, or professional assessment.
GHS classification
GHS Classification
Warning
H351 (97.5%): Suspected of causing cancer [Warning Carcinogenicity]
P203, P280, P318, P405, and P501 (click each P-code to see the statement)
Aggregated GHS information provided per 40 reports by companies from 3 notifications to the ECHA C&L Inventory.
Hazard information
Hazard Classes and CategoriesCarc. 2 (97.5%)
Toxicology
USGS Health-Based Screening Levels for Evaluating Water-Quality
Equilenin
Hormone and(or) waste-water effluent contaminant
Smith, C.D. and Nowell, L.H., 2024. Health-Based Screening Levels for evaluating water-quality data (3rd ed.). DOI:10.5066/F71C1TWP
Safety data
- wgk
- 2
- ridadr
- UN 1648 3/PG 2
- risk_code
- 11-20/21/22-36-48-40
- Signal word
- Danger
- Symbol(GHS)
- GHS02,GHS07
- hazard_code
- F,Xn
- safety_code
- 16-26-36-36/37
- Hazard statements
- H225-H302-H312-H319-H332
- Precautionary statements
- P210-P280-P305+P351+P338
Chemistry & industry
Applications
UsesEquilenin is a naturally occuring estrogenic steroidal hormone (1,2) isolated from urine of pregnant mares (3). Not found in human urine. Component of conjugated estrogenic hormones. Estrogen. 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.
UsesEstrogenic steroidal hormone isolated from urine of pregnant mares. Occurs naturally in the d-form. Not found in human urine. Component of conjugated estrogenic hormones. Estrogen.
Additional notes
DefinitionChEBI: Equilenin is a 3-hydroxy steroid that is estrone which carries two double bonds at positions 6 and 8. It is found in the urine of pregnant mare's and extensively used for estrogen replacement therapy in postmenopausal women. It has a role as a mammalian metabolite and an antioxidant. It is a 3-hydroxy steroid and a 17-oxo steroid.
Related reactions
0 records
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Compound notes
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