Basic Info

Common Name2-Phenoxyethanol(F05120)
2D Structure
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.

FRCD IDF05120
CAS Number122-99-6
PubChem CID31236
FormulaC8H10O2
IUPAC Name

2-phenoxyethanol

InChI Key

QCDWFXQBSFUVSP-UHFFFAOYSA-N

InChI

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

Canonical SMILES

C1=CC=C(C=C1)OCCO

Isomeric SMILES

C1=CC=C(C=C1)OCCO

Synonyms
        
            Ethylene glycol monophenyl ether
        
            Ethylene glycol phenyl ether
        
            2-PHENOXYETHANOL
        
            122-99-6
        
            Phenoxyethanol
        
            Phenyl cellosolve
        
            Ethanol, 2-phenoxy-
        
            Phenoxytol
        
            Phenoxethol
        
            Phenoxetol
        
Classifies
                

                  
                    Pollutant
                  

                
        
Update DateNov 13, 2018 17:07

Chemical Taxonomy

KingdomOrganic compounds
SuperclassBenzenoids
ClassPhenol ethers
SubclassNot available
Intermediate Tree NodesNot available
Direct ParentPhenol ethers
Alternative Parents
Molecular FrameworkAromatic homomonocyclic compounds
SubstituentsPhenoxy compound - Phenol ether - Alkyl aryl ether - Monocyclic benzene moiety - Ether - Organic oxygen compound - Hydrocarbon derivative - Primary alcohol - Organooxygen compound - Alcohol - Aromatic homomonocyclic compound
DescriptionThis compound belongs to the class of organic compounds known as phenol ethers. These are aromatic compounds containing an ether group substituted with a benzene ring.

Properties

Property NameProperty Value
Molecular Weight138.166
Hydrogen Bond Donor Count1
Hydrogen Bond Acceptor Count2
Rotatable Bond Count3
Complexity77.3
Monoisotopic Mass138.068
Exact Mass138.068
XLogP1.2
Formal Charge0
Heavy Atom Count10
Defined Atom Stereocenter Count0
Undefined Atom Stereocenter Count0
Defined Bond Stereocenter Count0
Undefined Bond Stereocenter Count0
Isotope Atom Count0
Covalently-Bonded Unit Count1

ADMET

Model Result Probability
Absorption
Blood-Brain BarrierBBB+0.8292
Human Intestinal AbsorptionHIA+0.9834
Caco-2 PermeabilityCaco2+0.7609
P-glycoprotein SubstrateNon-substrate0.7000
P-glycoprotein InhibitorNon-inhibitor0.6856
Non-inhibitor0.6176
Renal Organic Cation TransporterNon-inhibitor0.7555
Distribution
Subcellular localizationMitochondria0.8297
Metabolism
CYP450 2C9 SubstrateNon-substrate0.8203
CYP450 2D6 SubstrateNon-substrate0.8053
CYP450 3A4 SubstrateNon-substrate0.7146
CYP450 1A2 InhibitorNon-inhibitor0.7318
CYP450 2C9 InhibitorNon-inhibitor0.9482
CYP450 2D6 InhibitorNon-inhibitor0.9613
CYP450 2C19 InhibitorNon-inhibitor0.7656
CYP450 3A4 InhibitorNon-inhibitor0.9650
CYP Inhibitory PromiscuityLow CYP Inhibitory Promiscuity0.8578
Excretion
Toxicity
Human Ether-a-go-go-Related Gene InhibitionWeak inhibitor0.7361
Non-inhibitor0.8449
AMES ToxicityNon AMES toxic0.9133
CarcinogensNon-carcinogens0.8174
Fish ToxicityLow FHMT0.8235
Tetrahymena Pyriformis ToxicityLow TPT0.7141
Honey Bee ToxicityHigh HBT0.7444
BiodegradationReady biodegradable0.8235
Acute Oral ToxicityIII0.8740
Carcinogenicity (Three-class)Non-required0.5595

Model Value Unit
Absorption
Aqueous solubility-0.7728LogS
Caco-2 Permeability1.3422LogPapp, cm/s
Distribution
Metabolism
Excretion
Toxicity
Rat Acute Toxicity2.0085LD50, mol/kg
Fish Toxicity2.4117pLC50, mg/L
Tetrahymena Pyriformis Toxicity-0.6666pIGC50, ug/L

References

TitleJournalDatePubmed ID
Comparative Evaluation of Key Aroma-Active Compounds in Raw and Cooked Red Mullet(Mullus barbatus) by Aroma Extract Dilution Analysis.J Agric Food Chem2017 Sep 2728862440
Ethylhexylglycerin Impairs Membrane Integrity and Enhances the Lethal Effect ofPhenoxyethanol.PLoS One2016 Oct 2627783695
Escherichia coli β-galactosidase-catalyzed synthesis of 2-phenoxyethanol galactoside and its characterization.Bioprocess Biosyst Eng2015 Feb25217153
The Toluene o-Xylene Monooxygenase Enzymatic Activity for the Biosynthesis ofAromatic Antioxidants.PLoS One2015 Apr 2725915063
Hypersensitivity reactions to vaccine constituents: a case series and review ofthe literature.Dermatitis2012 May-Jun22653170
In vitro induction of apoptosis vs. necrosis by widely used preservatives:2-phenoxyethanol, a mixture of isothiazolinones, imidazolidinyl urea and1,2-pentanediol.Biochem Pharmacol2002 Feb 111853695

Targets

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
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 ]
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
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 ]