1,4-Dioxane (CED0002622)

Record Information
Version1.0
Creation Date2009-03-06 18:58:17 UTC
Update Date2026-05-14 17:49:17 UTC
Accession NumberCHEM000183
Identification
Common Name1,4-Dioxane
ClassSmall Molecule
Description
1,4-Dioxane (C4H8O2) is an exogenous organic compound with an average molecular weight of 88.11 g/mol that exists as a liquid at room temperature. 1,4-Dioxane belongs to the 1,4-dioxanes, a subclass of dioxanes within the organic compounds. This compound is classified as a superclass organoheterocyclic compound. It serves as an industrial solvent (PMC11733951, PMC8880212, PMC9056551), industrial stabilizer (PMC8633123), surfactant, and fragrance, as well as a non-polar chemical solvent. Biologically, it is identified as a carcinogenic agent. Exposure to 1,4-Dioxane occurs through oral, touch, and inhalation routes, with literature support specifically for inhalation (PMC13303702). It has been recorded in 46 sources, including drinking water, tap water, bottled water, and desalinated water. It is also found in aquatic systems such as groundwater, surface water, seawater, and freshwater, as well as in wastewater, industrial wastewater, and wastewater treatment effluent. Other sources include food contact materials, fermentation processes for beer, preparation of malt, preparation of wine or sparkling wine, and processing meats. It is also present in household cleaning and consumer products like soap dispensers and bleaching agents, and in electrical and electronic equipment including amplifiers, antennas, communication cables or conductors, and auxiliary devices. The compound is associated with cancer (PMC10005944, PMC9835328). Six protein targets have been recorded for 1,4-Dioxane, including Epsin-1 (EPN1), Tumor necrosis factor ligand superfamily member 13B (TNFSF13B), Transforming growth factor beta-3 proprotein (TGFB3), and Transient receptor potential cation channel subfamily A member 1 (TRPA1).
Contaminant Type
  • Cosmetic Toxin
  • Ether
  • Household Toxin
  • Industrial/Workplace Toxin
  • Lachrymator
  • Organic Compound
  • PMT
  • Pollutant
  • Solvent
  • Synthetic Compound
Chemical Structure
Synonyms
ValueSource
1,4-DIETHYLENE dioxideChEBI
1,4-DioxacyclohexaneChEBI
1,4-DioxanChEBI
Di(ethylene oxide)ChEBI
Dioxan-1,4ChEBI
Dioxane-1,4ChEBI
Glycol ethylene etherChEBI
p-DioxaneChEBI
Tetrahydro-1,4-dioxinChEBI
Tetrahydro-p-dioxinChEBI
Tetrahydro-para-dioxinChEBI
DioxaneMeSH
Diethylene etherMeSH
DioxanMeSH
Chemical FormulaC4H8O2
Average Molecular Mass88.105 g/mol
Monoisotopic Mass88.052 g/mol
CAS Registry Number123-91-1
IUPAC Name1,4-dioxane
Traditional Namedioxane
SMILESC1COCCO1
InChI IdentifierInChI=1S/C4H8O2/c1-2-6-4-3-5-1/h1-4H2
InChI KeyRYHBNJHYFVUHQT-UHFFFAOYSA-N
Chemical Taxonomy
Description Belongs to the class of organic compounds known as 1,4-dioxanes. These are organic compounds containing 1,4-dioxane, an aliphatic six-member ring with two oxygen atoms in ring positions 1 and 4.
KingdomOrganic compounds
Super ClassOrganoheterocyclic compounds
ClassDioxanes
Sub Class1,4-dioxanes
Direct Parent1,4-dioxanes
Alternative Parents
Substituents
  • Para-dioxane
  • Oxacycle
  • Ether
  • Dialkyl ether
  • Organic oxygen compound
  • Hydrocarbon derivative
  • Organooxygen compound
  • Aliphatic heteromonocyclic compound
Molecular FrameworkAliphatic heteromonocyclic compounds
External Descriptors
Biological Properties
StatusDetected and Not Quantified
OriginExogenous
Cellular Locations
  • Cytoplasm
  • Extracellular
Biofluid LocationsNot Available
Tissue LocationsNot Available
Applications
Biological Roles
Chemical Roles
Organoleptic EffectsNot Available
Physical Properties
StateLiquid
Appearance1,4-Dioxane is a colorless volatile liquid with a faint pleasant odor and mixes easily with water. (4)
Experimental Properties
PropertyValue
Melting Point11.8°C
Boiling Point101.1 °C
Solubility1000 mg/mL at 20 °C [RIDDICK,JA et al. (1986)]
Predicted Properties
PropertyValueSource
Water Solubility283 g/LALOGPS
logP-0.23ALOGPS
logP-0.094ChemAxon
logS0.51ALOGPS
pKa (Strongest Basic)-3.9ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count2ChemAxon
Hydrogen Donor Count0ChemAxon
Polar Surface Area18.46 ŲChemAxon
Rotatable Bond Count0ChemAxon
Refractivity22.09 m³·mol⁻¹ChemAxon
Polarizability8.97 ųChemAxon
Number of Rings1ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterNoChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleNoChemAxon
Spectra
Spectra
Spectrum TypeDescriptionSplash KeyDeposition DateView
GC-MSGC-MS Spectrumsplash10-0570-9000000000-fdad6aa284c3554c651bNot AvailableView Spectrum
Predicted GC-MSPredicted GC-MS Spectrumsplash10-056u-9000000000-ecaeff4720923991aaf7Not AvailableView Spectrum
Predicted GC-MSPredicted GC-MS SpectrumNot AvailableNot AvailableView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrumsplash10-000i-9000000000-a45455298eba19de60adNot AvailableView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrumsplash10-000i-9000000000-77a0261c34ff328faf53Not AvailableView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrumsplash10-08fu-9000000000-f3d10a4316418b32ed1dNot AvailableView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrumsplash10-000i-9000000000-7416375fa93c0232c2a5Not AvailableView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrumsplash10-000i-9000000000-cde6a647139e5c454cdeNot AvailableView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrumsplash10-056r-9000000000-5654a8542422e5b26444Not AvailableView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrumsplash10-0002-9000000000-1cd14a6c0dba761ba726Not AvailableView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrumsplash10-0a4m-9000000000-633cab61fb801edbb652Not AvailableView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrumsplash10-052g-9000000000-4a133ce242a34983b4d0Not AvailableView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrumsplash10-052o-9000000000-65decf9e96649a33752eNot AvailableView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrumsplash10-06rf-9000000000-0632a2171f1de13ca240Not AvailableView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrumsplash10-0006-9000000000-06f5fc3dedd188a15fe9Not AvailableView Spectrum
MSMS Spectrumsplash10-004i-9000000000-fabd529b7bd7382fe095Not AvailableView Spectrum
1D NMR13C NMR Spectrum (1D, D2O, predicted)Not AvailableNot AvailableView Spectrum
1D NMR1H NMR Spectrum (1D, D2O, predicted)Not AvailableNot AvailableView Spectrum
Toxicity Profile
Mechanism of ToxicityThough the mechanism of toxicity of 1,4-dioxane has not yet been elucidated, it is known that its carcinogenic effects are caused by a non-genotoxic mechanism that is most likely cytotoxic in nature. (4, 6)
Carcinogenicity (IARC Classification)2B, possibly carcinogenic to humans. (3)
Minimum Risk LevelNot Available
Symptoms1,4-Dioxane causes eye and respiratory tract irritation. (5)
TreatmentNot Available
Toxicity Values
Toxicity ValueUnitValue RangeOrganismDose DescriptorRoute of ExposurePredicted or ExperimentalReference
1550.0mg/kgNot AvailableRabbitLD50IntravenousexperimentalA710
4350.0mg/kgNot AvailableMouseLD50SubcutaneousexperimentalA710
8300.0mg/kg>8300RabbitLD50DermalexperimentalA710
2100.0mg/kgNot AvailableDogLD50OralexperimentalA710
799.0mg/kgNot AvailableRatLD50IntraperitonealexperimentalT14
46.0g/m3Not AvailableRatLC50Inhalation (2 hours)experimentalA710
Health Effects
Health EffectRelationshipDirectionReference
cancerassociated_withNot AvailablePMC10005944 , PMC9835328 , PMC9835328
Exposure Sources
Source IDSourceSectorReference
3Irrigation waterAgriculture & land managementNot Available
19Indoor airAir, dust & atmospheric transportNot Available
27Water CoolersAppliances, HVAC & refrigerantsNot Available
43Water heatersAppliances, HVAC & refrigerantsNot Available
50GroundwaterAquatic systems & sedimentsNot Available
51Surface waterAquatic systems & sedimentsNot Available
52SeawaterAquatic systems & sedimentsNot Available
53FreshwaterAquatic systems & sedimentsNot Available
70Stormwater runoffAutomotive & urban infrastructureNot Available
88Waterproofing spraysBuilding & ConstructionNot Available
115Drinking waterDrinking water & water supplyNot Available
116Tap waterDrinking water & water supplyNot Available
117Bottled waterDrinking water & water supplyNot Available
118Desalinated waterDrinking water & water supplyNot Available
181Ballast waterMarine, shipping & aquacultureNot Available
182Bilge waterMarine, shipping & aquacultureNot Available
468Industrial wastewaterWastewater, sanitation & biosolidsNot Available
470Wastewater treatment effluentWastewater, sanitation & biosolidsNot Available
475Mine wastewaterWastewater, sanitation & biosolidsNot Available
477Wastewater, unspecifiedWastewater, sanitation & biosolidsNot Available
494Food contact materialsFood, food processing & cookwareNot Available
505AmplifiersElectrical & Electronic EquipmentNot Available
506AntennasElectrical & Electronic EquipmentNot Available
507Auxiliary DevicesElectrical & Electronic EquipmentNot Available
510Communication Cables Or ConductorsElectrical & Electronic EquipmentNot Available
513Cores Yokes Or ArmaturesElectrical & Electronic EquipmentNot Available
515Discharge Tubes With Liquid Pool CathodesElectrical & Electronic EquipmentNot Available
517Electric SwitchesElectrical & Electronic EquipmentNot Available
518Electrically Stimulated Smoking DevicesElectrical & Electronic EquipmentNot Available
520Emergency Protective DevicesElectrical & Electronic EquipmentNot Available
521Fixed Capacitors And Their ManufactureElectrical & Electronic EquipmentNot Available
527MagnetsElectrical & Electronic EquipmentNot Available
529Power CablesElectrical & Electronic EquipmentNot Available
530Radio Transmission SystemsElectrical & Electronic EquipmentNot Available
531RelaysElectrical & Electronic EquipmentNot Available
536Superconductive Or Hyperconductive Conductors Cables Or Transmission LinesElectrical & Electronic EquipmentNot Available
537Television SystemsElectrical & Electronic EquipmentNot Available
538Thin Magnetic FilmsElectrical & Electronic EquipmentNot Available
544Fermentation Processes For BeerFood, food processing & cookwareNot Available
547Preparation Of MaltFood, food processing & cookwareNot Available
549Preparation Of Wine Or Sparkling WineFood, food processing & cookwareNot Available
552Processing MeatsFood, food processing & cookwareNot Available
555Bleaching AgentsHousehold cleaning & consumer productsNot Available
556Cigar CigarettesHousehold cleaning & consumer productsNot Available
560Other Smoking RequisitesHousehold cleaning & consumer productsNot Available
564Soap DispensersHousehold cleaning & consumer productsNot Available
578Making CigarsIndustrial manufacturing & chemical processingNot Available
579Manufacture Of Iron Or SteelIndustrial manufacturing & chemical processingNot Available
581Paper Making MachinesIndustrial manufacturing & chemical processingNot Available
589Life BuoysMarine, shipping & aquacultureNot Available
592Marine Propulsion Or SteeringMarine, shipping & aquacultureNot Available
594Ship HullsMarine, shipping & aquacultureNot Available
597ChemosterilantsAgriculture & land managementNot Available
602MolluscicidesAgriculture & land managementNot Available
604Pest AttractantsAgriculture & land managementNot Available
605Pest RepellantsAgriculture & land managementNot Available
607Rodenticides(1)Agriculture & land managementNot Available
608RodenticidesAgriculture & land managementNot Available
609AftershavePersonal care & cosmeticsNot Available
612Body Washing Or Cleaning ImplementsPersonal care & cosmeticsNot Available
613DepilatoriesPersonal care & cosmeticsNot Available
617Lip Care ProductsPersonal care & cosmeticsNot Available
619Manicure PedicurePersonal care & cosmeticsNot Available
631Anthraquinone DyesTextiles, leather & furnishingsNot Available
633Azo DyesTextiles, leather & furnishingsNot Available
638Decorating TextilesTextiles, leather & furnishingsNot Available
639Degreasing LeatherTextiles, leather & furnishingsNot Available
643HeadwearTextiles, leather & furnishingsNot Available
648Nitro DyesTextiles, leather & furnishingsNot Available
650Purses Luggage Hand BagsTextiles, leather & furnishingsNot Available
652RopesTextiles, leather & furnishingsNot Available
653SewingTextiles, leather & furnishingsNot Available
655Slide FastenersTextiles, leather & furnishingsNot Available
657Surface Finishing Of LeatherTextiles, leather & furnishingsNot Available
659Transfer PrintingTextiles, leather & furnishingsNot Available
662Yarns Or ThreadsTextiles, leather & furnishingsNot Available
Pathways
0 pathways

No pathways found

No metabolic pathways have been associated with this synthetic chemical

Targets
StructureProteinUniProt IDOrganismRelationshipDetails
Click to view 3D structureAcetyl-CoA carboxylaseQ3V4E6Zea maysPredicted (SEA)714.5
DNA-dependent protein kinase catalytic subunit structureClick to view 3D structureDNA-dependent protein kinase catalytic subunitP78527HumansPredicted (SEA)7459.59
Glycogen synthase kinase-3 beta structureClick to view 3D structureGlycogen synthase kinase-3 betaP49841HumansPredicted (SEA)7740.31
Replicase polyprotein 1ab structureClick to view 3D structureReplicase polyprotein 1abP0DTD1SARS-CoV-2Predicted (SEA)7709.49
Phosphatidylinositol 4,5-bisphosphate 3-kinase catalytic subunit alpha isoform structureClick to view 3D structurePhosphatidylinositol 4,5-bisphosphate 3-kinase catalytic subunit alpha isoformP42336HumansPredicted (SEA)7704.19
Click to view 3D structurePhosphatidylinositol 4,5-bisphosphate 3-kinase catalytic subunit beta isoformP42338HumansPredicted (SEA)7678.35
Click to view 3D structureTumor necrosis factor receptor superfamily member 16Q9Z0W1Mus musculusPredicted (SEA)882.654
Protein kinase C gamma type structureClick to view 3D structureProtein kinase C gamma typeP05129HumansPredicted (SEA)7736.42
Lysosomal acid lipase/cholesteryl ester hydrolase structureClick to view 3D structureLysosomal acid lipase/cholesteryl ester hydrolaseP38571HumansPredicted (SEA)638.052
Click to view 3D structurePlasma membrane ATPase 1P05030Saccharomyces cerevisiae (strain ATCC 204508 / S288c) (Baker's yeast)Predicted (SEA)1406.66
Phosphatidylinositol 4,5-bisphosphate 3-kinase catalytic subunit delta isoform structureClick to view 3D structurePhosphatidylinositol 4,5-bisphosphate 3-kinase catalytic subunit delta isoformO00329HumansPredicted (SEA)7720.93
Click to view 3D structureDNA-dependent protein kinase catalytic subunitP97313Mus musculusPredicted (SEA)1839.89
Protein kinase C alpha type structureClick to view 3D structureProtein kinase C alpha typeP17252HumansPredicted (SEA)7737.59
Protein kinase C beta type structureClick to view 3D structureProtein kinase C beta typeP05771HumansPredicted (SEA)7711.12
Apoptotic protease-activating factor 1 structureClick to view 3D structureApoptotic protease-activating factor 1O14727HumansPredicted (SEA)7560.17
[Pyruvate dehydrogenase (acetyl-transferring)] kinase isozyme 1, mitochondrial structureClick to view 3D structure[Pyruvate dehydrogenase (acetyl-transferring)] kinase isozyme 1, mitochondrialQ15118HumansPredicted (SEA)7657.72
Click to view 3D structureDual specificity protein phosphataseQ7T2L8Danio rerioPredicted (SEA)1563.37
Sigma non-opioid intracellular receptor 1 structureClick to view 3D structureSigma non-opioid intracellular receptor 1Q99720HumansPredicted (SEA)7773.87
Phosphatidylinositol 4,5-bisphosphate 3-kinase catalytic subunit gamma isoform structureClick to view 3D structurePhosphatidylinositol 4,5-bisphosphate 3-kinase catalytic subunit gamma isoformP48736HumansPredicted (SEA)7737.98
Click to view 3D structureProcollagen-lysine,2-oxoglutarate 5-dioxygenase 1Q02809HumansPredicted (SEA)4953.23
Multifunctional procollagen lysine hydroxylase and glycosyltransferase LH3 structureClick to view 3D structureMultifunctional procollagen lysine hydroxylase and glycosyltransferase LH3O60568HumansPredicted (SEA)4953.23
Click to view 3D structureImmunoglobulin A1 protease autotransporterP44969Haemophilus influenzae (strain ATCC 51907 / DSM 11121 / KW20 / Rd)Predicted (SEA)2006.41
Click to view 3D structureSerine/threonine-protein phosphatase 2A 65 kDa regulatory subunit A alpha isoformQ76MZ3Mus musculusPredicted (SEA)161.07
Serine/threonine-protein kinase mTOR structureClick to view 3D structureSerine/threonine-protein kinase mTORP42345HumansPredicted (SEA)7733.62
Click to view 3D structurePhosphatidylinositol 4-phosphate 3-kinase C2 domain-containing subunit betaO00750HumansPredicted (SEA)7698.28
Epsin-1 structureClick to view 3D structureEpsin-1Q9Y6I3HumansKnownNot Available
Transforming growth factor beta-3 proprotein structureClick to view 3D structureTransforming growth factor beta-3 proproteinP10600HumansKnownNot Available
Tumor necrosis factor ligand superfamily member 13B structureClick to view 3D structureTumor necrosis factor ligand superfamily member 13BQ9Y275HumansKnownNot Available
Transient receptor potential cation channel subfamily A member 1 structureClick to view 3D structureTransient receptor potential cation channel subfamily A member 1O75762HumansKnownNot Available
Concentrations
Not Available
External Links
DrugBank IDDB03316
HMDB IDHMDB0244216
FooDB IDNot Available
Phenol Explorer IDNot Available
KNApSAcK IDC00055321
BiGG IDNot Available
BioCyc IDNot Available
METLIN IDNot Available
PDB IDNot Available
Wikipedia Link1,4-Dioxane
Chemspider ID29015
ChEBI ID47032
PubChem Compound IDNot Available
Kegg Compound IDC14440
YMDB IDNot Available
ECMDB IDNot Available
References
Synthesis ReferenceNot Available
MSDSNot Available
General References
1. https://www.ncbi.nlm.nih.gov/pubmed/?term=14550759
2. https://www.ncbi.nlm.nih.gov/pubmed/?term=18044507
3. https://www.ncbi.nlm.nih.gov/pubmed/?term=20598439