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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

Molecular Formula C3H6O
Molecular Weight 58.0791
Charge 0
Count
Stereochemistry RACEMIC
Additional Stereochemistry No
Defined Stereocenters 0 / 1
E/Z Centers 0
Optical Activity ( + / - )

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
Rapid process for purification of an extracellular beta-xylosidase by aqueous two-phase extraction.
2001 Apr 15
5-acyloxy-5-hydroxymethyltetrahydro-2-furancarboxylate as a novel template for protein kinase C (PKC) binding.
2001 Mar
Chiral separation of glycidyl selenide and glycidyl sulfide racemates on cellulose-based chiral stationary phases.
2001 Sep
Hemoglobin adducts of ethylene oxide, propylene oxide, acrylonitrile and acrylamide-biomarkers in occupational and environmental medicine.
2002 Aug 5
Analysis of DNA and hemoglobin adducts and sister chromatid exchanges in a human population occupationally exposed to propylene oxide: a pilot study.
2002 Mar
Formation of water-in-CO(2) microemulsions with non-fluorous surfactant Ls-54 and solubilization of biomacromolecules.
2002 Mar 15
Coordination chemistry and reactivity of monomeric alkoxides and amides of magnesium and zinc supported by the diiminato ligand CH(CMeNC(6)H(3)-2,6-(i)Pr(2))(2). A comparative study.
2002 May 20
Use of haemoglobin adducts in exposure monitoring and risk assessment.
2002 Oct 5
Moderation of oral bacterial adhesion on saliva-coated hydroxyapatite by polyaspartate.
2003
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 Apr
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 Aug 28
Evaluation of a novel propylene oxide-treated collagen material as a dural substitute.
2003 Dec
Effects of polyether-modified poly(acrylic acid) microgels on doxorubicin transport in human intestinal epithelial Caco-2 cell layers.
2003 Feb 14
Effect of Pluronic-block copolymers on the reduction of serum-mediated inhibition of gene transfer of polyethyleneimine-DNA complexes.
2003 Jun
Bacterial adherence to mucosal epithelium in the upper airways has less significance than believed.
2003 Jun 9
Preparation and characterization of biodegradable PLA polymeric blends.
2003 Mar
Direct synthesis of propylene oxide with CO2 as the solvent.
2003 Mar 10
Trimethyl phosphite as a trap for alkoxy radicals formed from the ring opening of oxiranylcarbinyl radicals. Conversion to alkenes. Mechanistic applications to the study of C-C versus C-O ring cleavage.
2003 Mar 19
Serial pathways from primate prefrontal cortex to autonomic areas may influence emotional expression.
2003 Oct 10
Dosimetry by means of DNA and hemoglobin adducts in propylene oxide-exposed rats.
2003 Sep 15
Artificial carrier for oxygen supply in biological systems.
2004 Apr
Core electron transitions as a probe for molecular chirality: natural circular dichroism at the carbon K-edge of methyloxirane.
2004 Apr 14
Biocatalytic resolution of glycidyl aryl ethers by Trichosporon loubierii : cell/substrate ratio influences the optical purity of (R) - epoxides.
2004 Aug
Cellular and genetic analysis of wound healing in Drosophila larvae.
2004 Aug
Effect of Pluronic on cellular uptake of cationic liposomes- mediated antisense oligonucleotides.
2004 Feb
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 Feb 20
(Salen)tin complexes: syntheses, characterization, crystal structures, and catalytic activity in the formation of propylene carbonate from CO(2) and propylene oxide.
2004 Jul 12
Thermodynamics of micellization of tapered statistical copolymers of ethylene oxide and propylene oxide in water.
2004 Jul 15
Coronaviridae and SARS-associated coronavirus strain HSR1.
2004 Mar
Unique reactions of glycosyl iodides with oxa- and thiocycloalkane acceptors.
2004 Mar 18
(Salen)CrIIIX catalysts for the copolymerization of carbon dioxide and epoxides: role of the initiator and cocatalyst.
2004 Mar 22
Design of a novel hydrogel-based intelligent system for controlled drug release.
2004 Mar 24
Push-pull tests for assessing in situ aerobic cometabolism.
2004 May-Jun
Interaction forces between polyethylene oxide-polypropylene oxide ABA copolymers adsorbed to hydrophobic surfaces.
2004 Sep 1
Patents
Substance Class Chemical
Created
by admin
on Fri Dec 15 15:02:39 GMT 2023
Edited
by admin
on Fri Dec 15 15:02:39 GMT 2023
Record UNII
Y4Y7NYD4BK
Record Status Validated (UNII)
Record Version
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Name Type Language
PROPYLENE OXIDE
FCC   MI   USP-RS  
Systematic 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  
Systematic 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 Fri Dec 15 15:02:39 GMT 2023 , Edited by admin on Fri Dec 15 15:02:39 GMT 2023
EPA PESTICIDE CODE 42501
Created by admin on Fri Dec 15 15:02:39 GMT 2023 , Edited by admin on Fri Dec 15 15:02:39 GMT 2023
Code System Code Type Description
NCI_THESAURUS
C44438
Created by admin on Fri Dec 15 15:02:39 GMT 2023 , Edited by admin on Fri Dec 15 15:02:39 GMT 2023
PRIMARY
WIKIPEDIA
Propylene oxide
Created by admin on Fri Dec 15 15:02:39 GMT 2023 , Edited by admin on Fri Dec 15 15:02:39 GMT 2023
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MERCK INDEX
m9239
Created by admin on Fri Dec 15 15:02:39 GMT 2023 , Edited by admin on Fri Dec 15 15:02:39 GMT 2023
PRIMARY Merck Index
FDA UNII
Y4Y7NYD4BK
Created by admin on Fri Dec 15 15:02:39 GMT 2023 , Edited by admin on Fri Dec 15 15:02:39 GMT 2023
PRIMARY
HSDB
173
Created by admin on Fri Dec 15 15:02:39 GMT 2023 , Edited by admin on Fri Dec 15 15:02:39 GMT 2023
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RXCUI
1368175
Created by admin on Fri Dec 15 15:02:39 GMT 2023 , Edited by admin on Fri Dec 15 15:02:39 GMT 2023
PRIMARY RxNorm
RS_ITEM_NUM
1576945
Created by admin on Fri Dec 15 15:02:39 GMT 2023 , Edited by admin on Fri Dec 15 15:02:39 GMT 2023
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CHEBI
38685
Created by admin on Fri Dec 15 15:02:39 GMT 2023 , Edited by admin on Fri Dec 15 15:02:39 GMT 2023
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SMS_ID
100000133279
Created by admin on Fri Dec 15 15:02:39 GMT 2023 , Edited by admin on Fri Dec 15 15:02:39 GMT 2023
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CAS
75-56-9
Created by admin on Fri Dec 15 15:02:39 GMT 2023 , Edited by admin on Fri Dec 15 15:02:39 GMT 2023
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PUBCHEM
6378
Created by admin on Fri Dec 15 15:02:39 GMT 2023 , Edited by admin on Fri Dec 15 15:02:39 GMT 2023
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EVMPD
SUB50061
Created by admin on Fri Dec 15 15:02:39 GMT 2023 , Edited by admin on Fri Dec 15 15:02:39 GMT 2023
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ECHA (EC/EINECS)
200-879-2
Created by admin on Fri Dec 15 15:02:39 GMT 2023 , Edited by admin on Fri Dec 15 15:02:39 GMT 2023
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DAILYMED
Y4Y7NYD4BK
Created by admin on Fri Dec 15 15:02:39 GMT 2023 , Edited by admin on Fri Dec 15 15:02:39 GMT 2023
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MESH
C009068
Created by admin on Fri Dec 15 15:02:39 GMT 2023 , Edited by admin on Fri Dec 15 15:02:39 GMT 2023
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EPA CompTox
DTXSID5021207
Created by admin on Fri Dec 15 15:02:39 GMT 2023 , Edited by admin on Fri Dec 15 15:02:39 GMT 2023
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