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2-Phenoxyethanol (T3D3900)

IdentificationTaxonomyBiological PropertiesPhysical PropertiesToxicity ProfileSpectraConcentrationsLinksReferencesGene RegulationTargets (2)XML
Targets (2)
Record Information
Version2.0
Creation Date2013-04-25 07:56:53 UTC
Update Date2014-12-24 20:26:34 UTC
Accession NumberT3D3900
Identification
Common Name2-Phenoxyethanol
ClassSmall Molecule
DescriptionPhenoxyethanol is chemical preservative, a glycol ether often used in dermatological products such as skin creams and sunscreen. It is a colorless oily liquid. It is a bactericide (usually used in conjunction with quaternary ammonium compounds), often used in place of sodium azide in biological buffers because phenoxyethanol is less toxic and non-reactive with copper and lead. It is used in many applications such as cosmetics, vaccines and pharmaceuticals as a preservative. It is also used as a fixative for perfumes, an insect repellent, a topical antiseptic, a solvent for cellulose acetate, some dyes, inks, and resins, in preservatives, pharmaceuticals, and in organic synthesis. The Food and Drug Administration has warned that the chemical is toxic to infants via ingestion, and can depress the central nervous system and may cause vomiting and diarrhea. Combined with Chlorphenesin, these two chemicals can cause respiratory depression in infants. Since these chemicals are often present in cosmetics and lotions applied to the hands and are easily ingested, caution should be exercised. The EPA (Environmental Protection Agency) data sheets show chromosomal changes and genetic mutation effects in testing as well as testicular atrophy and interference with reproductivity in mice.
Compound Type
  • Cosmetic Toxin
  • Dye
  • Ether
  • Food Toxin
  • Industrial/Workplace Toxin
  • Metabolite
  • Organic Compound
  • Pollutant
  • Preservative
  • Solvent
  • Synthetic Compound
Chemical Structure
Thumb
MOLSDFPDBSMILESInChI
Synonyms
Synonym
1-Hydroxy-2-phenoxyethane
2-Hydroxyethyl phenyl ether
2-Phenoxyethanol, 9CI
Dalpad A
Ethylene glycol monophenyl ether
Ethylene glycol phenyl ether
Newpol EFP
Phenoxetol
Phenylcellosolve
Chemical FormulaC8H10O2
Average Molecular Mass138.164 g/mol
Monoisotopic Mass138.068 g/mol
CAS Registry Number122-99-6
IUPAC Name2-phenoxyethan-1-ol
Traditional Namephenoxyethanol
SMILESOCCOC1=CC=CC=C1
InChI IdentifierInChI=1S/C8H10O2/c9-6-7-10-8-4-2-1-3-5-8/h1-5,9H,6-7H2
InChI KeyInChIKey=QCDWFXQBSFUVSP-UHFFFAOYSA-N
Chemical Taxonomy
Description belongs to the class of organic compounds known as phenol ethers. These are aromatic compounds containing an ether group substituted with a benzene ring.
KingdomOrganic compounds
Super ClassBenzenoids
ClassPhenol ethers
Sub ClassNot Available
Direct ParentPhenol ethers
Alternative Parents
Substituents
  • Phenoxy compound
  • Phenol ether
  • Alkyl aryl ether
  • Monocyclic benzene moiety
  • Ether
  • Organic oxygen compound
  • Hydrocarbon derivative
  • Primary alcohol
  • Organooxygen compound
  • Alcohol
  • Aromatic homomonocyclic compound
Molecular FrameworkAromatic homomonocyclic compounds
External Descriptors
Biological Properties
StatusDetected and Not Quantified
OriginExogenous
Cellular Locations
  • Cytoplasm
  • Extracellular
Biofluid LocationsNot Available
Tissue LocationsNot Available
PathwaysNot Available
Applications
Biological RolesNot Available
Chemical RolesNot Available
Physical Properties
StateLiquid
AppearanceColorless oily liquid.
Experimental Properties
PropertyValue
Melting Point11-13°C
Boiling Point245.2°C (473.4°F)
SolubilityNot Available
LogPNot Available
Predicted Properties
PropertyValueSource
Water Solubility24.1 g/LALOGPS
logP1.22ALOGPS
logP1.13ChemAxon
logS-0.76ALOGPS
pKa (Strongest Acidic)15.1ChemAxon
pKa (Strongest Basic)-2.8ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count2ChemAxon
Hydrogen Donor Count1ChemAxon
Polar Surface Area29.46 ŲChemAxon
Rotatable Bond Count3ChemAxon
Refractivity38.81 m³·mol⁻¹ChemAxon
Polarizability14.91 ųChemAxon
Number of Rings1ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Spectra
Spectra
Spectrum TypeDescriptionSplash KeyDeposition DateView
GC-MSGC-MS Spectrum - EI-B (Non-derivatized)splash10-0006-9100000000-b40ca28428e0018311ea2017-09-12View Spectrum
GC-MSGC-MS Spectrum - EI-B (Non-derivatized)splash10-0006-9100000000-f8c06faa8eb8d23a95c12017-09-12View Spectrum
GC-MSGC-MS Spectrum - EI-B (Non-derivatized)splash10-0006-9100000000-7b2a4d4d9b09c7b787412017-09-12View Spectrum
GC-MSGC-MS Spectrum - EI-B (Non-derivatized)splash10-0006-9100000000-9bb41b75d1ad646b88f02017-09-12View Spectrum
GC-MSGC-MS Spectrum - CI-B (Non-derivatized)splash10-000i-0900000000-9421e4830e44b33885702017-09-12View Spectrum
GC-MSGC-MS Spectrum - EI-B (Non-derivatized)splash10-0006-9000000000-f53c3891b4914dd833e82017-09-12View Spectrum
GC-MSGC-MS Spectrum - EI-B (Non-derivatized)splash10-0006-9200000000-b5db9ef1d198ca188c7c2017-09-12View Spectrum
GC-MSGC-MS Spectrum - EI-B (Non-derivatized)splash10-0006-9100000000-ab2d6abdcb42c80200702017-09-12View Spectrum
GC-MSGC-MS Spectrum - EI-B (Non-derivatized)splash10-0006-9000000000-480278f55ce8ffc42edb2017-09-12View Spectrum
GC-MSGC-MS Spectrum - EI-B (Non-derivatized)splash10-0006-9100000000-b40ca28428e0018311ea2018-05-18View Spectrum
GC-MSGC-MS Spectrum - EI-B (Non-derivatized)splash10-0006-9100000000-f8c06faa8eb8d23a95c12018-05-18View Spectrum
GC-MSGC-MS Spectrum - EI-B (Non-derivatized)splash10-0006-9100000000-7b2a4d4d9b09c7b787412018-05-18View Spectrum
GC-MSGC-MS Spectrum - EI-B (Non-derivatized)splash10-0006-9100000000-9bb41b75d1ad646b88f02018-05-18View Spectrum
GC-MSGC-MS Spectrum - CI-B (Non-derivatized)splash10-000i-0900000000-9421e4830e44b33885702018-05-18View Spectrum
GC-MSGC-MS Spectrum - EI-B (Non-derivatized)splash10-0006-9000000000-f53c3891b4914dd833e82018-05-18View Spectrum
GC-MSGC-MS Spectrum - EI-B (Non-derivatized)splash10-0006-9200000000-b5db9ef1d198ca188c7c2018-05-18View Spectrum
GC-MSGC-MS Spectrum - EI-B (Non-derivatized)splash10-0006-9100000000-ab2d6abdcb42c80200702018-05-18View Spectrum
GC-MSGC-MS Spectrum - EI-B (Non-derivatized)splash10-0006-9000000000-480278f55ce8ffc42edb2018-05-18View Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-0006-9200000000-7361de1cec4803e1cf4c2016-09-22View Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (1 TMS) - 70eV, Positivesplash10-00di-9200000000-c4a3f9110ef42a31b02c2017-10-06View Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, PositiveNot Available2021-10-12View Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, PositiveNot Available2021-10-12View Spectrum
LC-MS/MSLC-MS/MS Spectrum - QTOF 3V, positivesplash10-00dl-9800000000-d264e377296013a0caaa2020-07-22View Spectrum
LC-MS/MSLC-MS/MS Spectrum - QTOF 4V, positivesplash10-00dl-9700000000-232d8ba2fe1c4c7a1d9a2020-07-22View Spectrum
LC-MS/MSLC-MS/MS Spectrum - QTOF 5V, positivesplash10-006x-9500000000-a91a2ac720eff1ebcaa72020-07-22View Spectrum
LC-MS/MSLC-MS/MS Spectrum - QTOF 7V, positivesplash10-006x-9300000000-cd24e556b117ca837b0d2020-07-22View Spectrum
LC-MS/MSLC-MS/MS Spectrum - QTOF 10V, positivesplash10-0006-9100000000-60e5aeaf981325dbf3702020-07-22View Spectrum
LC-MS/MSLC-MS/MS Spectrum - QTOF 15V, positivesplash10-0006-9000000000-44adee01bcbbb6f012052020-07-22View Spectrum
LC-MS/MSLC-MS/MS Spectrum - QTOF 17V, positivesplash10-0006-9000000000-ff06f2176a46ce6b3e9d2020-07-22View Spectrum
LC-MS/MSLC-MS/MS Spectrum - QTOF 20V, positivesplash10-00kf-9000000000-28503e2d48df8aec3c592020-07-22View Spectrum
LC-MS/MSLC-MS/MS Spectrum - QTOF 23V, positivesplash10-00kf-9000000000-399719a15e64074994cf2020-07-22View Spectrum
LC-MS/MSLC-MS/MS Spectrum - QTOF 25V, positivesplash10-00kf-9000000000-d2dc6a0aae0416082acf2020-07-22View Spectrum
LC-MS/MSLC-MS/MS Spectrum - QTOF 27V, positivesplash10-014l-9000000000-32932848b2cfead29a002020-07-22View Spectrum
LC-MS/MSLC-MS/MS Spectrum - QTOF 30V, positivesplash10-014l-9000000000-1c834a91a5adc20fba1b2020-07-22View Spectrum
LC-MS/MSLC-MS/MS Spectrum - QTOF 33V, positivesplash10-014i-9000000000-a2f926fa84c5b56fcb752020-07-22View Spectrum
LC-MS/MSLC-MS/MS Spectrum - QTOF 35V, positivesplash10-014i-9000000000-8f6557af39a7b179151b2020-07-22View Spectrum
LC-MS/MSLC-MS/MS Spectrum - QTOF 40V, positivesplash10-014i-9000000000-43574a299eb0ad2a948a2020-07-22View Spectrum
LC-MS/MSLC-MS/MS Spectrum - QTOF 45V, positivesplash10-0uy0-9000000000-b9b823b53494f7b464de2020-07-22View Spectrum
LC-MS/MSLC-MS/MS Spectrum - n/a 9V, positivesplash10-00di-2900000000-b3f7ed42e0410d07d1cc2020-07-22View Spectrum
LC-MS/MSLC-MS/MS Spectrum - n/a 9V, positivesplash10-0006-9000000000-e4b899ed0c9972aba84a2020-07-22View Spectrum
LC-MS/MSLC-MS/MS Spectrum - Orbitrap 1V, positivesplash10-00di-0900000000-cfe6a185ea4382b7d8252020-07-22View Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-000i-3900000000-82d3ea499e49a07dc9f52016-08-03View Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-000b-9700000000-964c725a4c63566fc4582016-08-03View Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0002-9000000000-cdc0027ea13905c59bed2016-08-03View Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-000i-3900000000-4c096ad99ce685693f0c2016-08-03View Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0006-9300000000-519730edd99eab09801c2016-08-03View Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0006-9000000000-d0cfac43ffd18d6c4a422016-08-03View Spectrum
MSMass Spectrum (Electron Ionization)splash10-0006-9100000000-9c2de92b427cc8e302622014-09-20View Spectrum
1D NMR1H NMR Spectrum (1D, 90 MHz, CDCl3, experimental)Not Available2014-09-20View Spectrum
1D NMR13C NMR Spectrum (1D, 25.16 MHz, CDCl3, experimental)Not Available2014-09-23View Spectrum
1D NMR13C NMR Spectrum (1D, 100 MHz, D2O, predicted)Not Available2021-09-24View Spectrum
1D NMR1H NMR Spectrum (1D, 100 MHz, D2O, predicted)Not Available2021-09-24View Spectrum
1D NMR13C NMR Spectrum (1D, 1000 MHz, D2O, predicted)Not Available2021-09-24View Spectrum
1D NMR1H NMR Spectrum (1D, 1000 MHz, D2O, predicted)Not Available2021-09-24View Spectrum
1D NMR13C NMR Spectrum (1D, 200 MHz, D2O, predicted)Not Available2021-09-24View Spectrum
1D NMR1H NMR Spectrum (1D, 200 MHz, D2O, predicted)Not Available2021-09-24View Spectrum
1D NMR13C NMR Spectrum (1D, 300 MHz, D2O, predicted)Not Available2021-09-24View Spectrum
1D NMR1H NMR Spectrum (1D, 300 MHz, D2O, predicted)Not Available2021-09-24View Spectrum
1D NMR13C NMR Spectrum (1D, 400 MHz, D2O, predicted)Not Available2021-09-24View Spectrum
1D NMR1H NMR Spectrum (1D, 400 MHz, D2O, predicted)Not Available2021-09-24View Spectrum
1D NMR13C NMR Spectrum (1D, 500 MHz, D2O, predicted)Not Available2021-09-24View Spectrum
1D NMR1H NMR Spectrum (1D, 500 MHz, D2O, predicted)Not Available2021-09-24View Spectrum
1D NMR13C NMR Spectrum (1D, 600 MHz, D2O, predicted)Not Available2021-09-24View Spectrum
1D NMR1H NMR Spectrum (1D, 600 MHz, D2O, predicted)Not Available2021-09-24View Spectrum
1D NMR13C NMR Spectrum (1D, 700 MHz, D2O, predicted)Not Available2021-09-24View Spectrum
1D NMR1H NMR Spectrum (1D, 700 MHz, D2O, predicted)Not Available2021-09-24View Spectrum
1D NMR13C NMR Spectrum (1D, 800 MHz, D2O, predicted)Not Available2021-09-24View Spectrum
1D NMR1H NMR Spectrum (1D, 800 MHz, D2O, predicted)Not Available2021-09-24View Spectrum
1D NMR13C NMR Spectrum (1D, 900 MHz, D2O, predicted)Not Available2021-09-24View Spectrum
1D NMR1H NMR Spectrum (1D, 900 MHz, D2O, predicted)Not Available2021-09-24View Spectrum
Toxicity Profile
Route of ExposureDermal (1); ingestion
Mechanism of Toxicity2-Phenoxyethanol is a glycol ether. Glycol ethers can produce toxicity following oxidation to the corresponding aldehyde and alkoxyacetic acid by alcohol dehydrogenase (ADH; EC 1.1.1.1) and aldehyde dehydrogenase (ALDH; EC 1.2.1.3), respectively. (1) 2-Phenoxyethanol causes reduction of NMDA-induced membrane currents, indicating a neurotoxic potential for 2-phenoxyethanol. (2)
MetabolismOxidized to the corresponding aldehyde and alkoxyacetic acid by alcohol dehydrogenase (ADH; EC 1.1.1.1) and aldehyde dehydrogenase (ALDH; EC 1.2.1.3), respectively. (1)
Toxicity ValuesNot Available
Lethal DoseNot Available
Carcinogenicity (IARC Classification)No indication of carcinogenicity to humans (not listed by IARC).
Uses/Sources2-Phenoxyethanol is used in many applications such as cosmetics, vaccines and pharmaceuticals as a preservative. It is also used as a fixative for perfumes, an insect repellent, a topical antiseptic, a solvent for cellulose acetate, some dyes, inks, and resins, in preservatives, pharmaceuticals, and in organic synthesis.
Minimum Risk LevelNot Available
Health EffectsNot Available
SymptomsMay cause vomiting and diarrhea.
TreatmentNot Available
Normal Concentrations
Not Available
Abnormal Concentrations
Not Available
DrugBank IDNot Available
HMDB IDHMDB41607
PubChem Compound ID31236
ChEMBL IDCHEMBL1229846
ChemSpider ID13848467
KEGG IDNot Available
UniProt IDNot Available
OMIM ID
ChEBI ID64275
BioCyc IDNot Available
CTD IDNot Available
Stitch IDNot Available
PDB ID268
ACToR IDNot Available
Wikipedia LinkNot Available
References
Synthesis ReferenceNot Available
MSDSLink
General References
  1. Lockley DJ, Howes D, Williams FM: Cutaneous metabolism of glycol ethers. Arch Toxicol. 2005 Mar;79(3):160-8. Epub 2004 Nov 17. [15551062 ]
  2. Musshoff U, Madeja M, Binding N, Witting U, Speckmann EJ: Effects of 2-phenoxyethanol on N-methyl-D-aspartate (NMDA) receptor-mediated ion currents. Arch Toxicol. 1999 Feb;73(1):55-9. [10207615 ]
  3. Yannai, Shmuel. (2004) Dictionary of food compounds with CD-ROM: Additives, flavors, and ingredients. Boca Raton: Chapman & Hall/CRC.
Gene Regulation
Up-Regulated GenesNot Available
Down-Regulated GenesNot Available

Targets

Target Details
1. Glutamate receptor ionotropic, NMDA 2A
General Function:
Zinc ion binding
Specific Function:
NMDA receptor subtype of glutamate-gated ion channels possesses high calcium permeability and voltage-dependent sensitivity to magnesium. Activation requires binding of agonist to both types of subunits.
Gene Name:
GRIN2A
Uniprot ID:
Q12879
Molecular Weight:
165281.215 Da
Binding/Activity Constants
TypeValueAssay TypeAssay Source
IC50362 uMNot AvailableNot Available
References
  1. Musshoff U, Madeja M, Binding N, Witting U, Speckmann EJ: Effects of 2-phenoxyethanol on N-methyl-D-aspartate (NMDA) receptor-mediated ion currents. Arch Toxicol. 1999 Feb;73(1):55-9. [10207615 ]
Target Details
2. ADP-ribosyl cyclase/cyclic ADP-ribose hydrolase 1
General Function:
Transferase activity
Specific Function:
Synthesizes the second messagers cyclic ADP-ribose and nicotinate-adenine dinucleotide phosphate, the former a second messenger for glucose-induced insulin secretion. Also has cADPr hydrolase activity. Also moonlights as a receptor in cells of the immune system.
Gene Name:
CD38
Uniprot ID:
P28907
Molecular Weight:
34328.145 Da
Binding/Activity Constants
TypeValueAssay TypeAssay Source
AC504.44 uMBSK_SAg_CD38_upBioSeek
References
  1. Sipes NS, Martin MT, Kothiya P, Reif DM, Judson RS, Richard AM, Houck KA, Dix DJ, Kavlock RJ, Knudsen TB: Profiling 976 ToxCast chemicals across 331 enzymatic and receptor signaling assays. Chem Res Toxicol. 2013 Jun 17;26(6):878-95. doi: 10.1021/tx400021f. Epub 2013 May 16. [23611293 ]