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Details

Stereochemistry RACEMIC
Molecular Formula C3H6O
Molecular Weight 58.0791
Optical Activity ( + / - )
Defined Stereocenters 0 / 1
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of PROPYLENE OXIDE

SMILES

CC1CO1

InChI

InChIKey=GOOHAUXETOMSMM-UHFFFAOYSA-N
InChI=1S/C3H6O/c1-3-2-4-3/h3H,2H2,1H3

HIDE SMILES / InChI
Propylene Oxide is a synthetic, highly-flammable, volatile, colorless liquid that is soluble in water and miscible with many organic solvents. The major use of propylene oxide is in the production of polyethers (the primary component of polyurethane foams) and propylene glycol. Propylene oxide is also used in the fumigation of foodstuffs and plastic medical instruments and in the manufacture of dipropylene glycol and glycol ethers, as herbicides, as solvents, and in the preparation of lubricants, surfactants, and oil demulsifiers. Propylene Oxide is a chiral epoxide, although it is commonly used as a racemic mixture. Acute (short-term) exposure of humans and animals to propylene oxide has caused eye and respiratory tract irritation. Dermal contact, even with dilute solutions, has caused skin irritation and necrosis in humans. Propylene oxide is also a mild central nervous system (CNS) depressant in humans. Inflammatory lesions of the nasal cavity, trachea, and lungs and neurological effects have been observed in animals chronically (long-term) exposed to propylene oxide by inhalation.

Originator

Sources: Justus Liebigs Annalen der Chemie (1866), 178-179.

Approval Year

PubMed

PubMed

TitleDatePubMed
Interaction forces between polyethylene oxide-polypropylene oxide ABA copolymers adsorbed to hydrophobic surfaces.
2004-09-01
Uptake of inspired propylene oxide in the upper respiratory tract of the f344 rat.
2004-09
Biocatalytic resolution of glycidyl aryl ethers by Trichosporon loubierii : cell/substrate ratio influences the optical purity of (R) - epoxides.
2004-08
Cellular and genetic analysis of wound healing in Drosophila larvae.
2004-08
Purification of hyperthermophilic archaeal amylolytic enzyme (MJA1) using thermoseparating aqueous two-phase systems.
2004-07-25
Chiral (salen)Co(III) catalyst for the synthesis of cyclic carbonates.
2004-07-21
Thermodynamics of micellization of tapered statistical copolymers of ethylene oxide and propylene oxide in water.
2004-07-15
(Salen)tin complexes: syntheses, characterization, crystal structures, and catalytic activity in the formation of propylene carbonate from CO(2) and propylene oxide.
2004-07-12
Push-pull tests for assessing in situ aerobic cometabolism.
2004-05-27
An Au-catalyzed cyclialkylation of electron-rich arenes with epoxides to prepare 3-chromanols.
2004-05-19
Metabolic pathway engineering to enhance aerobic degradation of chlorinated ethenes and to reduce their toxicity by cloning a novel glutathione S-transferase, an evolved toluene o-monooxygenase, and gamma-glutamylcysteine synthetase.
2004-05
Core electron transitions as a probe for molecular chirality: natural circular dichroism at the carbon K-edge of methyloxirane.
2004-04-14
Toxicity of propylene oxide at low pressure against life stages of four species of stored product insects.
2004-04
Artificial carrier for oxygen supply in biological systems.
2004-04
Ionophoric activity of pluronic block copolymers.
2004-03-30
Design of a novel hydrogel-based intelligent system for controlled drug release.
2004-03-24
(Salen)CrIIIX catalysts for the copolymerization of carbon dioxide and epoxides: role of the initiator and cocatalyst.
2004-03-22
Unique reactions of glycosyl iodides with oxa- and thiocycloalkane acceptors.
2004-03-18
Direct epoxidation of propylene by molecular oxygen over a catalyst system containing palladium and a peroxo-heteropoly compound in methanol.
2004-03-07
Monkeypox transmission and pathogenesis in prairie dogs.
2004-03
Coronaviridae and SARS-associated coronavirus strain HSR1.
2004-03
Absolute rate constants for reactions of tributylstannyl radicals with bromoalkanes, episulfides, and alpha-halomethyl-episulfides, -cyclopropanes, and -oxiranes: new rate expressions for sulfur and bromine atom abstraction.
2004-02-20
Effect of Pluronic on cellular uptake of cationic liposomes- mediated antisense oligonucleotides.
2004-02
A DFT investigation of the addition reaction of monomeric lithium enolate derived from propiophenone to propene oxide: examination of the possible transition structures.
2004-01-09
NMR study of molecular dynamics in selected hydrophilic polymers.
2004-01
Dimethyl sulphate; a hidden problem in occupational medicine.
2004-01
Structure of poly(propylene oxide) obtained with potassium glycidoxide in the presence of crown ether.
2004
Oxidation reactions in CO2: academic exercise or future green processes?
2003-12-01
Synthesis of novel tri- and tetrasubstituted C18 furan fatty esters.
2003-12
Evaluation of a novel propylene oxide-treated collagen material as a dural substitute.
2003-12
Cobalt-based complexes for the copolymerization of propylene oxide and CO2: active and selective catalysts for polycarbonate synthesis.
2003-11-17
Serial pathways from primate prefrontal cortex to autonomic areas may influence emotional expression.
2003-10-10
Effects of propylene oxide exposure on rat nasal respiratory cell proliferation.
2003-10
Dosimetry by means of DNA and hemoglobin adducts in propylene oxide-exposed rats.
2003-09-15
Ion/molecule reactions performed in a miniature cylindrical ion trap mass spectrometer.
2003-09
Mutagenic activity of ethylene oxide and propylene oxide under XPG proficient and deficient conditions in relation to N-7-(2-hydroxyalkyl)guanine levels in Drosophila.
2003-08-28
Pluronic L61 accelerates flip-flop and transbilayer doxorubicin permeation.
2003-08-18
[Gene mutation and sister chromatid exchange induced by propylene oxide].
2003-08
The characteristics of betamethasone-loaded chitosan microparticles by spray-drying method.
2003-07-10
Inhibition of growth and induction of apoptosis in human breast cancer by transfection of gef gene.
2003-07-07
Molecular dosimetry of N7-(2-hydroxypropyl)guanine in tissues of F344 rats after inhalation exposure to propylene oxide.
2003-07
Comparative kinetic studies of the copolymerization of cyclohexene oxide and propylene oxide with carbon dioxide in the presence of chromium salen derivatives. In situ FTIR measurements of copolymer vs cyclic carbonate production.
2003-06-25
Linking atomistic and mesoscale simulations of water-soluble polymers.
2003-06-18
Bacterial adherence to mucosal epithelium in the upper airways has less significance than believed.
2003-06-09
Inactivation of Bacillus anthracis spores.
2003-06
A rapid and effective synthesis of propylene carbonate using a supercritical CO2-ionic liquid system.
2003-04-07
Correspondence re: Czene et al., Analysis of DNA and hemoglobin adducts and sister chromatid exchanges in a human population occupationally exposed to propylene oxide: a pilot study. Cancer Epidemiol. Biomark. Prev., 11: 315-318, 2002.
2003-04
Two cases of occupational allergic contact dermatitis from a cycloaliphatic epoxy resin in a neat oil: case report.
2003-03-26
Multisite catalysis: a mechanistic study of beta-lactone synthesis from epoxides and CO--insights into a difficult case of homogeneous catalysis.
2003-03-17
Phase behavior and structure of an ABC triblock copolymer dissolved in selective solvent.
2003-01
Patents
Name Type Language
PROPYLENE OXIDE
FCC   MI   USP-RS  
Systematic Name English
1,2-PROPYLENE OXIDE
HSDB  
Preferred Name English
PROPYLENE OXIDE [FCC]
Common Name English
(±)-1,2-EPOXYPROPANE
Systematic Name English
PROPYLENE OXIDE [IARC]
Common Name English
1,2-EPOXYPROPANE
Systematic Name English
PROPYLENE EPOXIDE
Common Name English
PROPYLENE OXIDE [JAN]
Common Name English
METHYLOXACYCLOPROPANE
Systematic Name English
PROPYLENE OXIDE [USP-RS]
Common Name English
1,2-PROPYLENE OXIDE [HSDB]
Common Name English
EPIHYDRIN
Brand Name English
METHYL OXIRANE
Systematic Name English
DL-1,2-EPOXYPROPANE
Common Name English
2,3-EPOXYPROPANE
Systematic Name English
PROPYLENE OXIDE [MI]
Common Name English
OXIRANE, METHYL-
Systematic Name English
Classification Tree Code System Code
IARC Propylene oxide
NCI_THESAURUS C45408
Created by admin on Mon Mar 31 17:36:27 GMT 2025 , Edited by admin on Mon Mar 31 17:36:27 GMT 2025
EPA PESTICIDE CODE 42501
Created by admin on Mon Mar 31 17:36:27 GMT 2025 , Edited by admin on Mon Mar 31 17:36:27 GMT 2025
Code System Code Type Description
NCI_THESAURUS
C44438
Created by admin on Mon Mar 31 17:36:27 GMT 2025 , Edited by admin on Mon Mar 31 17:36:27 GMT 2025
PRIMARY
WIKIPEDIA
Propylene oxide
Created by admin on Mon Mar 31 17:36:27 GMT 2025 , Edited by admin on Mon Mar 31 17:36:27 GMT 2025
PRIMARY
MERCK INDEX
m9239
Created by admin on Mon Mar 31 17:36:27 GMT 2025 , Edited by admin on Mon Mar 31 17:36:27 GMT 2025
PRIMARY Merck Index
FDA UNII
Y4Y7NYD4BK
Created by admin on Mon Mar 31 17:36:27 GMT 2025 , Edited by admin on Mon Mar 31 17:36:27 GMT 2025
PRIMARY
HSDB
173
Created by admin on Mon Mar 31 17:36:27 GMT 2025 , Edited by admin on Mon Mar 31 17:36:27 GMT 2025
PRIMARY
RXCUI
1368175
Created by admin on Mon Mar 31 17:36:27 GMT 2025 , Edited by admin on Mon Mar 31 17:36:27 GMT 2025
PRIMARY RxNorm
RS_ITEM_NUM
1576945
Created by admin on Mon Mar 31 17:36:27 GMT 2025 , Edited by admin on Mon Mar 31 17:36:27 GMT 2025
PRIMARY
CHEBI
38685
Created by admin on Mon Mar 31 17:36:27 GMT 2025 , Edited by admin on Mon Mar 31 17:36:27 GMT 2025
PRIMARY
SMS_ID
100000133279
Created by admin on Mon Mar 31 17:36:27 GMT 2025 , Edited by admin on Mon Mar 31 17:36:27 GMT 2025
PRIMARY
CAS
75-56-9
Created by admin on Mon Mar 31 17:36:27 GMT 2025 , Edited by admin on Mon Mar 31 17:36:27 GMT 2025
PRIMARY
PUBCHEM
6378
Created by admin on Mon Mar 31 17:36:27 GMT 2025 , Edited by admin on Mon Mar 31 17:36:27 GMT 2025
PRIMARY
EVMPD
SUB50061
Created by admin on Mon Mar 31 17:36:27 GMT 2025 , Edited by admin on Mon Mar 31 17:36:27 GMT 2025
PRIMARY
ECHA (EC/EINECS)
200-879-2
Created by admin on Mon Mar 31 17:36:27 GMT 2025 , Edited by admin on Mon Mar 31 17:36:27 GMT 2025
PRIMARY
DAILYMED
Y4Y7NYD4BK
Created by admin on Mon Mar 31 17:36:27 GMT 2025 , Edited by admin on Mon Mar 31 17:36:27 GMT 2025
PRIMARY
MESH
C009068
Created by admin on Mon Mar 31 17:36:27 GMT 2025 , Edited by admin on Mon Mar 31 17:36:27 GMT 2025
PRIMARY
EPA CompTox
DTXSID5021207
Created by admin on Mon Mar 31 17:36:27 GMT 2025 , Edited by admin on Mon Mar 31 17:36:27 GMT 2025
PRIMARY