Basic information
- CAS
57-91-0- Standard SMILES
C[C@]12CC[C@@H]3c4ccc(O)cc4CC[C@H]3[C@@H]1CC[C@H]2O- InChIKey
VOXZDWNPVJITMN-SFFUCWETSA-N- Molecular formula
- C18H24O2
- Average molar mass
- 272.4 g/mol
- Monoisotopic mass
- 272.17763
Overview
17alpha-estradiol is an estradiol that is estra-1,3,5(10)-triene substituted by hydroxy groups at positions 3 and 17 (the 17alpha stereoisomer). It has a role as a geroprotector and an estrogen. It is an estradiol, a 17alpha-hydroxy steroid and a 3-hydroxy steroid.
Names & identifiers
- Preferred name
- alpha-Estradiol
- IUPAC
- (8R,9S,13S,14S,17R)-13-methyl-6,7,8,9,11,12,14,15,16,17-decahydrocyclopenta[a]phenanthrene-3,17-diol
- English name
- Estradiol
- Molecular formula
- C18H24O2
- Molecular weight
- 272.39
Names & synonyms
17alpha-Estradiol57-91-0alpha-EstradiolAlfatradiol17a-estradiol17-alpha-EstradiolEstradiol-17alpha3,17-DihydroxyestratrieneEpiestrol17-Epiestradiol(8R,9S,13S,14S,17R)-13-methyl-6,7,8,9,11,12,14,15,16,17-decahydrocyclopenta[a]phenanthrene-3,17-diolDTXSID8022377
Show more names
α-EstradiolBETA-ESTRADIOL17B-ESTRADIOLB-ESTRADIOL17α-estradiolEPIESTRADIOL
ESTRADIOL, ALPHA-3VQ38D63M7DTXCID702377Oestra-1,3,5(10)-triene-3,17alpha-diolCHEBI:171603,17alpha-Dihydroxyestra-1,3,5(10)-triene3,17alpha-Dihydroxyoestra-1,3,5(10)-trienealfatradiolum
Database identifiers
- CAS
57-91-0- PubChem CID
- 68570
- DTXSID
DTXSID8022377- ChEMBL
CHEMBL286452- ChEBI
Properties
Computed structural properties
- XLogP
- 4
- Topological polar surface area
- 40.5 Ų
- Hydrogen bond donors
- 2
- Hydrogen bond acceptors
- 2
- Rotatable bonds
- 0
- Heavy atoms
- 20
- Formal charge
- 0
- Complexity
- 382
Experimental & physicochemical properties
Chemical ClassesHormone
LipidsLipids -> Sterol Lipids [ST] -> Steroids [ST02] -> C18 steroids (estrogens) and derivatives [ST0201]
SpringerMaterials PropertiesAngular frequency
Solubility0.0039 mg/mL
Endocrine DisruptorsPotential endocrine disrupting compound
Melting Point216 - 219 °C
Physical DescriptionSolid
Collision Cross Section174.8 Ų [M-H]- [CCS Type: DT; Buffer gas: N2; Ionization: ESI-; Dataset: TOXCAST; Source Identifier: DTXSID8022377]
Physicochemical properties
- Melting point
- 176 · 176-180 °C(lit.)
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
This chemical does not meet GHS hazard criteria for 1.9% (3 of 154) of reports.
Danger
H350 (11.7%): May cause cancer [Danger Carcinogenicity]
P203, P260, P263, P264, P270, P280, P318, P319, P405, and P501 (click each P-code to see the statement)
Aggregated GHS information provided per 154 reports by companies from 8 notifications to the ECHA C&L Inventory. Each notification may be associated with multiple companies.
Hazard information
Regulatory InformationEstra-1,3,5(10)-triene-3,17-diol, (17.alpha.)-: Does not have an individual approval but may be used under an appropriate group standard
Hazard Classes and CategoriesCarc. 1A (11.7%)
Toxicology
Carcinogen ClassificationNo indication of carcinogenicity to humans (not listed by IARC).
USGS Health-Based Screening Levels for Evaluating Water-Quality
17-alpha-Estradiol
Hormone
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
- F
- 8-10
- PPE
- dust mask type N95 (US), Eyeshields, Gloves
- wgk
- 3
- rtecs
- KG3750000
Chemistry & industry
Pharmacology
Mechanism of Action
MITO-4509 is an orally-administered drug candidate that shows neuro-protective activity and reductions in beta-amyloid in animal models of Alzheimer's disease, and is well tolerated in a completed human Phase I trial. In addition to Alzheimer's disease, MITO-4509 shows potential for use in Parkinson's disease, Friedreich's ataxia, retinitis pigmentosa, and mild cognitive impairment ("MCI" is often considered a precursor to Alzheimer's disease).
MeSH Pharmacological Classification
Drugs used to treat or prevent skin disorders or for the routine care of skin.
Drugs that inhibit 3-OXO-5-ALPHA-STEROID 4-DEHYDROGENASE. They are commonly used to reduce the production of DIHYDROTESTOSTERONE.
Cellular LocationsExtracellular
Uses & manufacturing
UsesUse (kg; approx.) in Germany (2009): >10
Applications
UsesEstradiol (known as α-Estradiol or 17 α-Estradiol) is a biologically active estrogen in human breast cancer cells in tissue culture. 17-Εstradiol and its selective receptor, ER-X, are not part of a classical hormone/receptor endocrine system but of a system with important autocrine/paracrine functions in the developing and adult brain. 17-Estradiol may have enormous implications for hormone replacement strategies at the menopause and in the treatment of such neurodegenerative disorders as Alzheimer’s disease and ischemic stroke.
Upstream & downstream products
Upstream raw materials
Related reactions
1 records
Compound notes
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