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Epiestradiol (PC000298)

Record Information
Version1.0
Creation date2015-10-09 22:29:43 UTC
Update date2017-01-19 02:36:19 UTC
FoodComEx IDPC000298
FoodDB RecordFDB011524
Chemical Information
NameEpiestradiol
Description17a-estradiol is found in the estrogen patch. The estrogen patch is a delivery system for estradiol used as hormone replacement therapy to treat the symptoms of menopause, such as hot flashes and vaginal dryness, and to prevent osteoporosis. Originally marketed as Vivelle (Novartis), it was discontinued in 2003 and reintroduced in a smaller form as Vivelle-Dot. Although the estrogen is given transdermally rather than in the standard oral tablets, the estrogen patch carries similar risks and benefits as more conventional forms of estrogen-only hormone replacement therapy.
CAS Number57-91-0
Structure
Thumb
MOLSDFPDBSMILESInChI
Synonyms
SynonymSource
(17alpha)-estra-1,3,5(10)-triene-3,17-diolbiospider
α-estradiolbiospider
1,3,5-Estratriene-3,17α-diolbiospider
1,3,5-Estratriene-3,17a-diolbiospider
1,3,5(10)-Estratriene-3,17alpha-diolbiospider
13b-Methyl-1,3,5(10)-gonatriene-3,17a-diolbiospider
17-alpha-Estradiolbiospider
17-Epiestradiolbiospider
17α-Estradiolbiospider
17α-Oestradiolbiospider
17a-EstradiolGenerator
17a-Oestradiolbiospider
17alpha estradiolbiospider
17alpha-Estradiolbiospider
17α-estradiolGenerator
3, 17-Dihydroxyestratrienebiospider
3, 17α-Dihydroxyestra-1,3,5(10)-trienebiospider
3, 17α-Dihydroxyoestra-1,3,5(10)-trienebiospider
3,17-Dihydroxyestratrienebiospider
3,17α-Dihydroxyestra-1,3,5(10)-trienebiospider
3,17α-Dihydroxyoestra-1,3,5(10)-trienebiospider
3,17a-Dihydroxyestra-1,3,5(10)-trienebiospider
3,17a-Dihydroxyoestra-1,3,5(10)-trienebiospider
3,17alpha-Dihydroxy-1,3,5(10)-estratrienebiospider
5A-Estran-3A,17B-diolbiospider
A-estradiolbiospider
Alfatradiolbiospider
Alfatradiol (inn)biospider
Alfatradiol, INNdb_source
Alpha-estradiolbiospider
b-Estradiol (obsol., misleading)db_source
Epiestradioldb_source
Epiestrolbiospider
Estra-1,3,5(10)-triene-3, 17α-diolbiospider
Estra-1,3,5(10)-triene-3,17-diolbiospider
Estra-1,3,5(10)-triene-3,17-diol, (17α)-biospider
Estra-1,3,5(10)-triene-3,17α-diolbiospider
Estra-1,3,5(10)-triene-3,17a-diolbiospider
estra-1,3,5(10)-triene-3,17alpha-diolbiospider
Estra-1,3,5(10)trien-3,17a-diolGenerator
Estra-1,3,5(10)trien-3,17alpha-diolChEBI
Estra-1,3,5(10)trien-3,17α-diolGenerator
Estradiolbiospider
Estradiol-17adb_source
estradiol-17alphabiospider
Estradiol-17αGenerator
Estradiol, 17α-biospider
Oestra-1,3,5(10)-triene-3, 17α-diolbiospider
Oestra-1,3,5(10)-triene-3,17α-diolbiospider
Oestra-1,3,5(10)-triene-3,17a-diolbiospider
Oestradiol-17αbiospider
α-estradiolGenerator
Chemical FormulaC18H24O2
IUPAC name15-methyltetracyclo[8.7.0.0^{2,7}.0^{11,15}]heptadeca-2,4,6-triene-5,14-diol
InChI IdentifierInChI=1S/C18H24O2/c1-18-9-8-14-13-5-3-12(19)10-11(13)2-4-15(14)16(18)6-7-17(18)20/h3,5,10,14-17,19-20H,2,4,6-9H2,1H3
InChI KeyVOXZDWNPVJITMN-UHFFFAOYSA-N
Isomeric SMILESCC12CCC3C(CCC4=C3C=CC(O)=C4)C1CCC2O
Average Molecular Weight272.382
Monoisotopic Molecular Weight272.177630012
Chemical Taxonomy
Description Belongs to the class of organic compounds known as estrogens and derivatives. These are steroids with a structure containing a 3-hydroxylated estrane.
KingdomOrganic compounds
Super ClassLipids and lipid-like molecules
ClassSteroids and steroid derivatives
Sub ClassEstrane steroids
Direct ParentEstrogens and derivatives
Alternative Parents
Substituents
  • Estrogen-skeleton
  • 17-hydroxysteroid
  • Hydroxysteroid
  • 3-hydroxysteroid
  • Phenanthrene
  • Tetralin
  • 1-hydroxy-2-unsubstituted benzenoid
  • Benzenoid
  • Cyclic alcohol
  • Secondary alcohol
  • Organic oxygen compound
  • Hydrocarbon derivative
  • Organooxygen compound
  • Alcohol
  • Aromatic homopolycyclic compound
Molecular FrameworkAromatic homopolycyclic compounds
External Descriptors
Physico-Chemical Properties - Experimental
PropertyValueReference
Experimental logPNot Available
Experimental Water Solubility0.0039 mg/mL at 25 oCYALKOWSKY,SH & DANNENFELSER,RM (1992)
Melting PointMp 223°DFC
Foods of Origin
FoodContent Range AverageReference
FoodReference
Production Data
Production Methodcommercial
Production Method ReferenceNot Available
Production Method Reference FileNot Available
Quantity AvailableProduction upon request, up to 1 g
Delivery TimeNot Available
Storage Formsolid
Storage Conditions-80°C
StabilityNot Available
PurityNot Available
Spectra
Spectral Data Upon RequestNot Available
Provider Information
Contact NameContact InstitutionContact Email
Rosa Vazquez Fresnovazquezf@ualberta.ca
Commercial Vendors
Cayman Chemical 20776
Toronto Research Chemicals E887995