T3DB: 2-Phenoxyethanol

Identification Taxonomy Biological Properties Physical Properties Toxicity Profile Spectra Concentrations Links References Gene Regulation Targets (2)XML

Targets (2)

Record Information

Version

2.0

Creation Date

2013-04-25 07:56:53 UTC

Update Date

2014-12-24 20:26:34 UTC

Accession Number

T3D3900

Identification

Common Name

2-Phenoxyethanol

Class

Small Molecule

Description

Phenoxyethanol 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

MOL SDF PDB SMILES InChI

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 Formula

C₈H₁₀O₂

Average Molecular Mass

138.164 g/mol

Monoisotopic Mass

138.068 g/mol

CAS Registry Number

122-99-6

IUPAC Name

2-phenoxyethan-1-ol

Traditional Name

phenoxyethanol

SMILES

OCCOC1=CC=CC=C1

InChI Identifier

InChI=1S/C8H10O2/c9-6-7-10-8-4-2-1-3-5-8/h1-5,9H,6-7H2

InChI Key

InChIKey=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.

Kingdom

Organic compounds

Super Class

Benzenoids

Class

Phenol ethers

Sub Class

Not Available

Direct Parent

Phenol 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 Framework

Aromatic homomonocyclic compounds

External Descriptors

aromatic ether (CHEBI:64275 )
primary alcohol (CHEBI:64275 )
hydroxyether (CHEBI:64275 )

Biological Properties

Status

Detected and Not Quantified

Origin

Exogenous

Cellular Locations

Cytoplasm
Extracellular

Biofluid Locations

Not Available

Tissue Locations

Not Available

Pathways

Not Available

Applications

Biological Roles

Not Available

Chemical Roles

Not Available

Physical Properties

State

Liquid

Appearance

Colorless oily liquid.

Experimental Properties

Property	Value
Melting Point	11-13°C
Boiling Point	245.2°C (473.4°F)
Solubility	Not Available
LogP	Not Available

Predicted Properties

Property	Value	Source
Water Solubility	24.1 g/L	ALOGPS
logP	1.22	ALOGPS
logP	1.13	ChemAxon
logS	-0.76	ALOGPS
pKa (Strongest Acidic)	15.1	ChemAxon
pKa (Strongest Basic)	-2.8	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	2	ChemAxon
Hydrogen Donor Count	1	ChemAxon
Polar Surface Area	29.46 Å²	ChemAxon
Rotatable Bond Count	3	ChemAxon
Refractivity	38.81 m³·mol⁻¹	ChemAxon
Polarizability	14.91 Å³	ChemAxon
Number of Rings	1	ChemAxon
Bioavailability	1	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	Yes	ChemAxon
Veber's Rule	Yes	ChemAxon
MDDR-like Rule	Yes	ChemAxon

Spectra

Spectrum Type	Description	Splash Key	Deposition Date	View
GC-MS	GC-MS Spectrum - EI-B (Non-derivatized)	splash10-0006-9100000000-b40ca28428e0018311ea	2017-09-12	View Spectrum
GC-MS	GC-MS Spectrum - EI-B (Non-derivatized)	splash10-0006-9100000000-f8c06faa8eb8d23a95c1	2017-09-12	View Spectrum
GC-MS	GC-MS Spectrum - EI-B (Non-derivatized)	splash10-0006-9100000000-7b2a4d4d9b09c7b78741	2017-09-12	View Spectrum
GC-MS	GC-MS Spectrum - EI-B (Non-derivatized)	splash10-0006-9100000000-9bb41b75d1ad646b88f0	2017-09-12	View Spectrum
GC-MS	GC-MS Spectrum - CI-B (Non-derivatized)	splash10-000i-0900000000-9421e4830e44b3388570	2017-09-12	View Spectrum
GC-MS	GC-MS Spectrum - EI-B (Non-derivatized)	splash10-0006-9000000000-f53c3891b4914dd833e8	2017-09-12	View Spectrum
GC-MS	GC-MS Spectrum - EI-B (Non-derivatized)	splash10-0006-9200000000-b5db9ef1d198ca188c7c	2017-09-12	View Spectrum
GC-MS	GC-MS Spectrum - EI-B (Non-derivatized)	splash10-0006-9100000000-ab2d6abdcb42c8020070	2017-09-12	View Spectrum
GC-MS	GC-MS Spectrum - EI-B (Non-derivatized)	splash10-0006-9000000000-480278f55ce8ffc42edb	2017-09-12	View Spectrum
GC-MS	GC-MS Spectrum - EI-B (Non-derivatized)	splash10-0006-9100000000-b40ca28428e0018311ea	2018-05-18	View Spectrum
GC-MS	GC-MS Spectrum - EI-B (Non-derivatized)	splash10-0006-9100000000-f8c06faa8eb8d23a95c1	2018-05-18	View Spectrum
GC-MS	GC-MS Spectrum - EI-B (Non-derivatized)	splash10-0006-9100000000-7b2a4d4d9b09c7b78741	2018-05-18	View Spectrum
GC-MS	GC-MS Spectrum - EI-B (Non-derivatized)	splash10-0006-9100000000-9bb41b75d1ad646b88f0	2018-05-18	View Spectrum
GC-MS	GC-MS Spectrum - CI-B (Non-derivatized)	splash10-000i-0900000000-9421e4830e44b3388570	2018-05-18	View Spectrum
GC-MS	GC-MS Spectrum - EI-B (Non-derivatized)	splash10-0006-9000000000-f53c3891b4914dd833e8	2018-05-18	View Spectrum
GC-MS	GC-MS Spectrum - EI-B (Non-derivatized)	splash10-0006-9200000000-b5db9ef1d198ca188c7c	2018-05-18	View Spectrum
GC-MS	GC-MS Spectrum - EI-B (Non-derivatized)	splash10-0006-9100000000-ab2d6abdcb42c8020070	2018-05-18	View Spectrum
GC-MS	GC-MS Spectrum - EI-B (Non-derivatized)	splash10-0006-9000000000-480278f55ce8ffc42edb	2018-05-18	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive	splash10-0006-9200000000-7361de1cec4803e1cf4c	2016-09-22	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (1 TMS) - 70eV, Positive	splash10-00di-9200000000-c4a3f9110ef42a31b02c	2017-10-06	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive	Not Available	2021-10-12	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive	Not Available	2021-10-12	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - QTOF 3V, positive	splash10-00dl-9800000000-d264e377296013a0caaa	2020-07-22	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - QTOF 4V, positive	splash10-00dl-9700000000-232d8ba2fe1c4c7a1d9a	2020-07-22	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - QTOF 5V, positive	splash10-006x-9500000000-a91a2ac720eff1ebcaa7	2020-07-22	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - QTOF 7V, positive	splash10-006x-9300000000-cd24e556b117ca837b0d	2020-07-22	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - QTOF 10V, positive	splash10-0006-9100000000-60e5aeaf981325dbf370	2020-07-22	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - QTOF 15V, positive	splash10-0006-9000000000-44adee01bcbbb6f01205	2020-07-22	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - QTOF 17V, positive	splash10-0006-9000000000-ff06f2176a46ce6b3e9d	2020-07-22	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - QTOF 20V, positive	splash10-00kf-9000000000-28503e2d48df8aec3c59	2020-07-22	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - QTOF 23V, positive	splash10-00kf-9000000000-399719a15e64074994cf	2020-07-22	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - QTOF 25V, positive	splash10-00kf-9000000000-d2dc6a0aae0416082acf	2020-07-22	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - QTOF 27V, positive	splash10-014l-9000000000-32932848b2cfead29a00	2020-07-22	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - QTOF 30V, positive	splash10-014l-9000000000-1c834a91a5adc20fba1b	2020-07-22	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - QTOF 33V, positive	splash10-014i-9000000000-a2f926fa84c5b56fcb75	2020-07-22	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - QTOF 35V, positive	splash10-014i-9000000000-8f6557af39a7b179151b	2020-07-22	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - QTOF 40V, positive	splash10-014i-9000000000-43574a299eb0ad2a948a	2020-07-22	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - QTOF 45V, positive	splash10-0uy0-9000000000-b9b823b53494f7b464de	2020-07-22	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - n/a 9V, positive	splash10-00di-2900000000-b3f7ed42e0410d07d1cc	2020-07-22	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - n/a 9V, positive	splash10-0006-9000000000-e4b899ed0c9972aba84a	2020-07-22	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - Orbitrap 1V, positive	splash10-00di-0900000000-cfe6a185ea4382b7d825	2020-07-22	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-000i-3900000000-82d3ea499e49a07dc9f5	2016-08-03	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-000b-9700000000-964c725a4c63566fc458	2016-08-03	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-0002-9000000000-cdc0027ea13905c59bed	2016-08-03	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-000i-3900000000-4c096ad99ce685693f0c	2016-08-03	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-0006-9300000000-519730edd99eab09801c	2016-08-03	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-0006-9000000000-d0cfac43ffd18d6c4a42	2016-08-03	View Spectrum
MS	Mass Spectrum (Electron Ionization)	splash10-0006-9100000000-9c2de92b427cc8e30262	2014-09-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 90 MHz, CDCl₃, experimental)	Not Available	2014-09-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 25.16 MHz, CDCl₃, experimental)	Not Available	2014-09-23	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 100 MHz, D₂O, predicted)	Not Available	2021-09-24	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 100 MHz, D₂O, predicted)	Not Available	2021-09-24	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 1000 MHz, D₂O, predicted)	Not Available	2021-09-24	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 1000 MHz, D₂O, predicted)	Not Available	2021-09-24	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 200 MHz, D₂O, predicted)	Not Available	2021-09-24	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 200 MHz, D₂O, predicted)	Not Available	2021-09-24	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 300 MHz, D₂O, predicted)	Not Available	2021-09-24	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 300 MHz, D₂O, predicted)	Not Available	2021-09-24	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 400 MHz, D₂O, predicted)	Not Available	2021-09-24	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 400 MHz, D₂O, predicted)	Not Available	2021-09-24	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 500 MHz, D₂O, predicted)	Not Available	2021-09-24	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 500 MHz, D₂O, predicted)	Not Available	2021-09-24	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 600 MHz, D₂O, predicted)	Not Available	2021-09-24	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 600 MHz, D₂O, predicted)	Not Available	2021-09-24	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 700 MHz, D₂O, predicted)	Not Available	2021-09-24	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 700 MHz, D₂O, predicted)	Not Available	2021-09-24	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 800 MHz, D₂O, predicted)	Not Available	2021-09-24	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 800 MHz, D₂O, predicted)	Not Available	2021-09-24	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 900 MHz, D₂O, predicted)	Not Available	2021-09-24	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 900 MHz, D₂O, predicted)	Not Available	2021-09-24	View Spectrum

Toxicity Profile

Route of Exposure

Dermal (1); ingestion

Mechanism of Toxicity

2-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)

Metabolism

Oxidized 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 Values

Not Available

Lethal Dose

Not Available

Carcinogenicity (IARC Classification)

No indication of carcinogenicity to humans (not listed by IARC).

Uses/Sources

2-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 Level

Not Available

Health Effects

Not Available

Symptoms

May cause vomiting and diarrhea.

Treatment

Not Available

Normal Concentrations

Not Available

Abnormal Concentrations

Not Available

External Links

DrugBank ID

Not Available

HMDB ID

PubChem Compound ID

ChEMBL ID

ChemSpider ID

KEGG ID

Not Available

UniProt ID

Not Available

OMIM ID

ChEBI ID

64275

BioCyc ID

Not Available

CTD ID

Not Available

Stitch ID

Not Available

PDB ID

268

ACToR ID

Not Available

Wikipedia Link

Not Available

References

Synthesis Reference

Not Available

MSDS

Link

General References

Lockley DJ, Howes D, Williams FM: Cutaneous metabolism of glycol ethers. Arch Toxicol. 2005 Mar;79(3):160-8. Epub 2004 Nov 17. [15551062 ]
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 ]
Yannai, Shmuel. (2004) Dictionary of food compounds with CD-ROM: Additives, flavors, and ingredients. Boca Raton: Chapman & Hall/CRC.

Gene Regulation

Up-Regulated Genes

Not Available

Down-Regulated Genes

Not 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

Type	Value	Assay Type	Assay Source
IC50	362 uM	Not Available	Not Available

References

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

Type	Value	Assay Type	Assay Source
AC50	4.44 uM	BSK_SAg_CD38_up	BioSeek

References

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 ]

2-Phenoxyethanol (T3D3900)

Structure for T3D3900: 2-Phenoxyethanol

Targets

Binding/Activity Constants

References

Binding/Activity Constants

References