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Details

Stereochemistry ACHIRAL
Molecular Formula C4H6O
Molecular Weight 70.0898
Optical Activity NONE
Defined Stereocenters 0 / 0
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of Vinyl ether

SMILES

C=COC=C

InChI

InChIKey=QYKIQEUNHZKYBP-UHFFFAOYSA-N
InChI=1S/C4H6O/c1-3-5-4-2/h3-4H,1-2H2

HIDE SMILES / InChI

Molecular Formula C4H6O
Molecular Weight 70.0898
Charge 0
Count
Stereochemistry ACHIRAL
Additional Stereochemistry No
Defined Stereocenters 0 / 0
E/Z Centers 0
Optical Activity NONE

Vinyl ether (divinyl ether) is a clear colorless liquid with a characteristic odor. Less dense than water. Vapors heavier than air. Toxic by inhalation. Leake and Chen in 1930 demonstrated that vinyl ether possessed anaesthetic properties, and in 1931 a purer and more stable product was prepared in the research laboratories of Merck and Co. by Ruigh and Major and was used as ananaesthetic on dogs by Knoefel, Guedel, and Leake. These investigators found that dogs were more easily anaesthetized by vinyl ether than by chloroform. They also found that the period of recovery was rapid and free from vomiting; moreover, they did not notice any significant pathological effect on the various organs.The first experiments on human beings were conducted in 1933 by Gelfan and Bell. The first extensive account of vinyl ether anaesthesia in man was published in 1934, when Goldschmidt et al. reported having used it in operations in 461 mixed cases. In all these cases vinyl ether appeared to have no undesirable effect on respiration, the circulation, the liver, or the kidneys. Vinyl ether was widely used in Europe and North America for at least 30 years, until it was replaced by halothane. Vinyl ether was marketed under the name of Vinethine in the United States, Vinesthine in the United Kingdom, and Vinydan in continental Europe. Vinyl ether outlasted many of the inhalation agents introduced in recent years, and served a very useful purpose until safer, non-flammable agents, became available in the mid1960s.

Approval Year

Doses

Doses

DosePopulationAdverse events​
3 mL single, respiratory
Recommended
Dose: 3 mL
Route: respiratory
Route: single
Dose: 3 mL
Sources:
unhealthy, 3-9
Health Status: unhealthy
Age Group: 3-9
Sources:
Other AEs: Convulsions...
Other AEs:
Convulsions (5 patients)
Sources:
AEs

AEs

AESignificanceDosePopulation
Convulsions 5 patients
3 mL single, respiratory
Recommended
Dose: 3 mL
Route: respiratory
Route: single
Dose: 3 mL
Sources:
unhealthy, 3-9
Health Status: unhealthy
Age Group: 3-9
Sources:
PubMed

PubMed

TitleDatePubMed
Triaryl(1-pyrenyl)bismuthonium salts: efficient photoinitiators for cationic polymerization of oxiranes and a vinyl ether.
2008-06-05
Design, synthesis and in vitro evaluation of vinyl ether type polymeric prodrugs of ibuprofen, ketoprofen and naproxen.
2008-05-22
Competitive protein adsorption to polymer surfaces from human serum.
2008-05
Construction of highly functionalized diazoacetoacetates via catalytic Mukaiyama-Michael reactions.
2008-04-17
Stereoselective construction of an unprecedented 7-8 fused ring system in micrandilactone a by [3,3]-sigmatropic rearrangement.
2008-02-21
How to improve the storage stability of aqueous polymeric film coatings.
2008-02-18
CCN activity and hygroscopic growth of organic aerosols following reactive uptake of ammonia.
2008-02-01
Sheddable coatings for long-circulating nanoparticles.
2008-01
Divinyl ether synthesis in garlic bulbs.
2008
Shotgun lipidomics identifies a paired rule for the presence of isomeric ether phospholipid molecular species.
2007-12-26
Hydration of vinyl ether groups by unsaturated glycoside hydrolases and their role in bacterial pathogenesis.
2007-12
Rh-catalyzed highly enantioselective formation of functionalized cyclopentanes and cyclopentanones.
2007-11-07
Vinylogous Mukaiyama aldol reactions with 4-oxy-2-trimethylsilyloxypyrroles: relevance to castanospermine synthesis.
2007-11-03
Separation of intact plasmalogens and all other phospholipids by a single run of high-performance liquid chromatography.
2007-11-01
Novel chlorhexidine releasing system developed from thermosensitive vinyl ether-based hydrogels.
2007-11
Dipole-LUMO/dipolarophile-HOMO controlled asymmetric cycloadditions of carbonyl ylides catalyzed by chiral Lewis acids.
2007-10-11
Highly regioselective internal heck arylation of hydroxyalkyl vinyl ethers by aryl halides in water.
2007-08-17
The investigation of protein adsorption behaviors on different functionalized polymers films.
2007-06
Organocatalytic claisen rearrangement: theory and experiment.
2007-05-25
Tandem Pd(II)-catalyzed vinyl ether exchange-Claisen rearrangement as a facile approach to gamma,delta-unsaturated aldehydes.
2007-05-25
Reduction of divinyl ether-containing polyunsaturated fatty acids in transgenic potato plants.
2007-03
Experimental and theoretical investigation on surfactant segregation in imprint lithography.
2007-01-30
A concise effective deprotection of spiro 3-cyclic thiaza ketal of steroidal 1,4-dien-3-one.
2007-01
Characterization of a divinyl ether biosynthetic pathway specifically associated with pathogenesis in tobacco.
2007-01
CuCl2-catalyzed one-pot formation of tetrahydroquinolines from N-methyl-N-alkylanilines and vinyl ethers in the presence of t-butylhydroperoxide.
2006-12-20
Design, synthesis and application of vinyl ether compounds for gene and drug delivery.
2006-11-28
Dirhodium(II) tetrakis(perfluorobutyrate)-catalyzed 1,4-hydrosilylation of alpha,beta-unsaturated carbonyl compounds.
2006-11
Respective contributions of polar vs enthalpy effects in the addition/fragmentation of mercaptobenzoxazole-derived thiyl radicals and analogues to double bonds.
2006-10-19
Crystal structure of unsaturated glucuronyl hydrolase complexed with substrate: molecular insights into its catalytic reaction mechanism.
2006-10-06
Selective plasmenylcholine oxidation by hypochlorous acid: formation of lysophosphatidylcholine chlorohydrins.
2006-10
Kinetic and mechanistic study of the gas-phase reactions of a series of vinyl ethers with the nitrate radical.
2006-09-28
Structure of unsaturated rhamnogalacturonyl hydrolase complexed with substrate.
2006-09-08
Synthesis, X-ray crystallography, and computational analysis of 1-azafenestranes.
2006-09-06
Multiple hydride reduction pathways in isoflavonoids.
2006-08-25
Synthesis of pyrrolidines via palladium(II)-catalyzed aerobic oxidative carboamination of butyl vinyl ether and styrenes with allyl tosylamides.
2006-07-20
In vitro and in vivo antitumor activity of the novel derivatized polyvinyl alcohol-based polymer P10(4).
2006-06-01
Selective terminal heck arylation of vinyl ethers with aryl chlorides: a combined experimental-computational approach including synthesis of betaxolol.
2006-05-12
The enantioselective synthesis of elecanacin through an intramolecular naphthoquinone-vinyl ether photochemical cycloaddition.
2006-03-07
Stereoselective synthesis of 3-aminoindan-1-ones and subsequent incorporation into HIV-1 protease inhibitors.
2006-02-03
Colloid probe AFM investigation of interactions between fibrinogen and PEG-like plasma polymer surfaces.
2006-01-03
Catalytic asymmetric claisen rearrangement in natural product synthesis: synthetic studies toward (-)-xeniolide F.
2005-12-08
Investigations of step-growth thiol-ene polymerizations for novel dental restoratives.
2005-12
Regioselective Lewis acid-mediated [1,3] rearrangement of allylvinyl ethers.
2005-05-26
Generation and reaction of tungsten-containing carbonyl ylides: [3 + 2]-cycloaddition reaction with electron-rich alkenes.
2005-03-02
Inhibition of diethyl ether degradation in Rhodococcus sp. strain DEE5151 by glutaraldehyde and ethyl vinyl ether.
2005-02-15
Masked 3-aminoindan-1-ones by a palladium-catalyzed three-component annulation reaction.
2005-02-04
Addition of carbon-centered radicals to double bonds: influence of the alkene structure.
2005-02-04
Hidden stereospecificity in the biosynthesis of divinyl ether fatty acids.
2005-02
Free radical oxidation of plasmalogen glycerophosphocholine containing esterified docosahexaenoic acid: structure determination by mass spectrometry.
2005-01-15
Complexation between poly(maleic acid/octyl vinyl ether) and poly(vinyl caprolactam) in aqueous solution and at the alumina/water interface.
2002-09-01
Patents

Patents

Sample Use Guides

In the blood, anaesthesia is produced with a remarkably small concentration; in dogs this is 28 mg per 100 ccm.
Route of Administration: Respiratory
Substance Class Chemical
Created
by admin
on Mon Mar 31 17:33:11 GMT 2025
Edited
by admin
on Mon Mar 31 17:33:11 GMT 2025
Record UNII
2H2T044E11
Record Status Validated (UNII)
Record Version
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Name Type Language
Vinyl ether
WHO-DD  
Systematic Name English
DIVINYL ETHER
MI  
Preferred Name English
Vinyl ether [WHO-DD]
Common Name English
DIVINYL ETHER [MI]
Common Name English
Classification Tree Code System Code
WHO-VATC QN01AA02
Created by admin on Mon Mar 31 17:33:11 GMT 2025 , Edited by admin on Mon Mar 31 17:33:11 GMT 2025
WHO-ATC N01AA02
Created by admin on Mon Mar 31 17:33:11 GMT 2025 , Edited by admin on Mon Mar 31 17:33:11 GMT 2025
Code System Code Type Description
CAS
109-93-3
Created by admin on Mon Mar 31 17:33:11 GMT 2025 , Edited by admin on Mon Mar 31 17:33:11 GMT 2025
PRIMARY
WIKIPEDIA
Divinyl ether
Created by admin on Mon Mar 31 17:33:11 GMT 2025 , Edited by admin on Mon Mar 31 17:33:11 GMT 2025
PRIMARY
ChEMBL
CHEMBL2105883
Created by admin on Mon Mar 31 17:33:11 GMT 2025 , Edited by admin on Mon Mar 31 17:33:11 GMT 2025
PRIMARY
DRUG CENTRAL
3645
Created by admin on Mon Mar 31 17:33:11 GMT 2025 , Edited by admin on Mon Mar 31 17:33:11 GMT 2025
PRIMARY
FDA UNII
2H2T044E11
Created by admin on Mon Mar 31 17:33:11 GMT 2025 , Edited by admin on Mon Mar 31 17:33:11 GMT 2025
PRIMARY
SMS_ID
100000076712
Created by admin on Mon Mar 31 17:33:11 GMT 2025 , Edited by admin on Mon Mar 31 17:33:11 GMT 2025
PRIMARY
EPA CompTox
DTXSID5074555
Created by admin on Mon Mar 31 17:33:11 GMT 2025 , Edited by admin on Mon Mar 31 17:33:11 GMT 2025
PRIMARY
DRUG BANK
DB13690
Created by admin on Mon Mar 31 17:33:11 GMT 2025 , Edited by admin on Mon Mar 31 17:33:11 GMT 2025
PRIMARY
MESH
C100195
Created by admin on Mon Mar 31 17:33:11 GMT 2025 , Edited by admin on Mon Mar 31 17:33:11 GMT 2025
PRIMARY
ECHA (EC/EINECS)
203-720-5
Created by admin on Mon Mar 31 17:33:11 GMT 2025 , Edited by admin on Mon Mar 31 17:33:11 GMT 2025
PRIMARY
PUBCHEM
8024
Created by admin on Mon Mar 31 17:33:11 GMT 2025 , Edited by admin on Mon Mar 31 17:33:11 GMT 2025
PRIMARY
EVMPD
SUB15697MIG
Created by admin on Mon Mar 31 17:33:11 GMT 2025 , Edited by admin on Mon Mar 31 17:33:11 GMT 2025
PRIMARY
MERCK INDEX
m4697
Created by admin on Mon Mar 31 17:33:11 GMT 2025 , Edited by admin on Mon Mar 31 17:33:11 GMT 2025
PRIMARY Merck Index