Cannabis Compound Database: Showing Compound Card for 2-Phenoxyethanol (CDB000516)

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Record Information

Version

1.0

Created at

2020-03-19 00:41:19 UTC

Updated at

2021-01-04 18:48:56 UTC

CannabisDB ID

CDB000516

Secondary Accession Numbers

Not Available

Cannabis Compound Identification

Common Name

2-Phenoxyethanol

Description

2-Phenoxyethanol, also known as arosol, phenoxetol, phenoxytol or phenyl cellosolve, belongs to the class of organic compounds known as phenol ethers. These are aromatic compounds containing an ether group substituted with a benzene ring. 2-Phenoxyethanol is an aromatic ether that is phenol substituted on oxygen by a 2-hydroxyethyl group. There are two known isomers of phenoxyethanol including 1-Phenoxyethanol and 2-Phenoxyethanol. 2-Phenoxyethanol exists as a clear colorless oily liquid. 2-Phenoxyethanol exists as a colorless oily liquid with a faint rose-like, balsam or cinnamyl odour and is a flavouring ingredient. Industrially it is used as a perfume fixative, an insect repellent, an antiseptic, a solvent for cellulose acetate, dyes, inks, and resins, a preservative for pharmaceuticals, cosmetics and lubricants, as a stabilizer in perfumes and soaps, an anesthetic in fish aquaculture; and in organic synthesis. 2-Phenoxyethanol is also used as an alternative to formaldehyde-releasing preservatives. In Japan and the European Union, its concentration in cosmetics is restricted to 1%. Exposure to 2-Phenoxyethanol has been linked to reactions ranging from eczema to severe, life-threatening allergic reactions. 2-Phenoxyethanol exhibits antibacterial activity and is effective against gram-negative and gram-positive bacteria, as well as the yeast Candida albicans. 2-Phenoxyethanol can also be used as a vaccine preservative however it may induce an allergic reactions, which may result in a nodular inflammation at the site of injection. 2-Phenoxyethanol reversibly inhibits NMDAR-mediated ion currents (PMID: 10959804 ). 2-Phenoxyethanol is a potentially toxic compound and is a known central nervous system depressant. It binds to and inhibits NMDA receptors (PMID: 10207615 ) and reversibly inhibits NMDAR-mediated ion currents (PMID: 10959804 ). 2-Phenoxyethanol is a known constituent of marijuana (cannabis) smoke. 2-Phenoxyethanol is formed during the combustion of cannabis ( Ref:DOI ).

Structure

MOL SDF PDB SMILES InChI

Synonyms

Value	Source
1-Hydroxy-2-phenoxyethane	ChEBI
2-Hydroxyethyl phenyl ether	ChEBI
2-Phenoxyethyl alcohol	ChEBI
beta-Hydroxyethyl phenyl ether	ChEBI
Ethylene glycol monophenyl ether	ChEBI
Phenoxyethanol	ChEBI
Phenoxytol	ChEBI
Phenyl cellosolve	ChEBI
Phenylmonoglycol ether	ChEBI
Fungal terminator	Kegg
b-Hydroxyethyl phenyl ether	Generator
Β-hydroxyethyl phenyl ether	Generator
2-Phenoxyethanol, 9ci	HMDB
Dalpad a	HMDB
Ethylene glycol phenyl ether	HMDB
Newpol efp	HMDB
Phenoxetol	HMDB
Phenylcellosolve	HMDB
Emuclens	MeSH
Erisept	MeSH
Phenoxethol	MeSH

Chemical Formula

C₈H₁₀O₂

Average Molecular Weight

138.17

Monoisotopic Molecular Weight

138.0681

IUPAC Name

2-phenoxyethan-1-ol

Traditional Name

phenoxyethanol

CAS Registry Number

122-99-6

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

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 )

Ontology

Physiological effect

Health effect:

Health condition:

Gastrointestinal disorders:

Disposition

Route of exposure:

Parenteral:

Dermal

Enteral:

Ingestion

Source:

Food

Synthetic:

Personal care product

Biological location:

Biofluid and excreta:

Subcellular:

Cytoplasm

Cell and elements:

Extracellular

Role

Industrial application:

Personal care products

Household products:

Pesticide:

Insect repellent

Food and nutrition:

Flavoring agent

Pharmaceutical industry:

Pharmaceutical

Biological role:

Nutrient

Physical Properties

State

Solid

Experimental Properties

Property	Value	Reference
Melting Point	11-13 °C	Not Available
Boiling Point	Not Available	Not Available
Water Solubility	Not Available	Not Available
logP	Not Available	Not Available

Predicted Properties

Property	Value	Source
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	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	No	ChemAxon
Veber's Rule	Yes	ChemAxon
MDDR-like Rule	No	ChemAxon

Spectra

EI-MS/GC-MS

Type	Description	Splash Key	View
EI-MS	Mass Spectrum (Electron Ionization)	splash10-0006-9100000000-9c2de92b427cc8e30262	2014-09-20	View Spectrum
GC-MS	2-Phenoxyethanol, non-derivatized, GC-MS Spectrum	splash10-0006-9100000000-b40ca28428e0018311ea	Spectrum
GC-MS	2-Phenoxyethanol, non-derivatized, GC-MS Spectrum	splash10-0006-9100000000-f8c06faa8eb8d23a95c1	Spectrum
GC-MS	2-Phenoxyethanol, non-derivatized, GC-MS Spectrum	splash10-0006-9100000000-7b2a4d4d9b09c7b78741	Spectrum
GC-MS	2-Phenoxyethanol, non-derivatized, GC-MS Spectrum	splash10-0006-9100000000-9bb41b75d1ad646b88f0	Spectrum
GC-MS	2-Phenoxyethanol, non-derivatized, GC-MS Spectrum	splash10-000i-0900000000-9421e4830e44b3388570	Spectrum
GC-MS	2-Phenoxyethanol, non-derivatized, GC-MS Spectrum	splash10-0006-9000000000-f53c3891b4914dd833e8	Spectrum
GC-MS	2-Phenoxyethanol, non-derivatized, GC-MS Spectrum	splash10-0006-9200000000-b5db9ef1d198ca188c7c	Spectrum
GC-MS	2-Phenoxyethanol, non-derivatized, GC-MS Spectrum	splash10-0006-9100000000-ab2d6abdcb42c8020070	Spectrum
GC-MS	2-Phenoxyethanol, non-derivatized, GC-MS Spectrum	splash10-0006-9000000000-480278f55ce8ffc42edb	Spectrum
GC-MS	2-Phenoxyethanol, non-derivatized, GC-MS Spectrum	splash10-0006-9100000000-b40ca28428e0018311ea	Spectrum
GC-MS	2-Phenoxyethanol, non-derivatized, GC-MS Spectrum	splash10-0006-9100000000-f8c06faa8eb8d23a95c1	Spectrum
GC-MS	2-Phenoxyethanol, non-derivatized, GC-MS Spectrum	splash10-0006-9100000000-7b2a4d4d9b09c7b78741	Spectrum
GC-MS	2-Phenoxyethanol, non-derivatized, GC-MS Spectrum	splash10-0006-9100000000-9bb41b75d1ad646b88f0	Spectrum
GC-MS	2-Phenoxyethanol, non-derivatized, GC-MS Spectrum	splash10-000i-0900000000-9421e4830e44b3388570	Spectrum
GC-MS	2-Phenoxyethanol, non-derivatized, GC-MS Spectrum	splash10-0006-9000000000-f53c3891b4914dd833e8	Spectrum
GC-MS	2-Phenoxyethanol, non-derivatized, GC-MS Spectrum	splash10-0006-9200000000-b5db9ef1d198ca188c7c	Spectrum
GC-MS	2-Phenoxyethanol, non-derivatized, GC-MS Spectrum	splash10-0006-9100000000-ab2d6abdcb42c8020070	Spectrum
GC-MS	2-Phenoxyethanol, non-derivatized, GC-MS Spectrum	splash10-0006-9000000000-480278f55ce8ffc42edb	Spectrum
Predicted GC-MS	2-Phenoxyethanol, non-derivatized, Predicted GC-MS Spectrum - 70eV, Positive	splash10-0006-9200000000-7361de1cec4803e1cf4c	Spectrum
Predicted GC-MS	2-Phenoxyethanol, 1 TMS, Predicted GC-MS Spectrum - 70eV, Positive	splash10-00di-9200000000-c4a3f9110ef42a31b02c	Spectrum
Predicted GC-MS	2-Phenoxyethanol, non-derivatized, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	2-Phenoxyethanol, non-derivatized, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum

MS/MS

Type	Description	Splash Key	View
MS/MS	LC-MS/MS Spectrum - QTOF 3V, positive	splash10-00dl-9800000000-d264e377296013a0caaa	2020-07-22	View Spectrum
MS/MS	LC-MS/MS Spectrum - QTOF 4V, positive	splash10-00dl-9700000000-232d8ba2fe1c4c7a1d9a	2020-07-22	View Spectrum
MS/MS	LC-MS/MS Spectrum - QTOF 5V, positive	splash10-006x-9500000000-a91a2ac720eff1ebcaa7	2020-07-22	View Spectrum
MS/MS	LC-MS/MS Spectrum - QTOF 7V, positive	splash10-006x-9300000000-cd24e556b117ca837b0d	2020-07-22	View Spectrum
MS/MS	LC-MS/MS Spectrum - QTOF 10V, positive	splash10-0006-9100000000-60e5aeaf981325dbf370	2020-07-22	View Spectrum
MS/MS	LC-MS/MS Spectrum - QTOF 15V, positive	splash10-0006-9000000000-44adee01bcbbb6f01205	2020-07-22	View Spectrum
MS/MS	LC-MS/MS Spectrum - QTOF 17V, positive	splash10-0006-9000000000-ff06f2176a46ce6b3e9d	2020-07-22	View Spectrum
MS/MS	LC-MS/MS Spectrum - QTOF 20V, positive	splash10-00kf-9000000000-28503e2d48df8aec3c59	2020-07-22	View Spectrum
MS/MS	LC-MS/MS Spectrum - QTOF 23V, positive	splash10-00kf-9000000000-399719a15e64074994cf	2020-07-22	View Spectrum
MS/MS	LC-MS/MS Spectrum - QTOF 25V, positive	splash10-00kf-9000000000-d2dc6a0aae0416082acf	2020-07-22	View Spectrum
MS/MS	LC-MS/MS Spectrum - QTOF 27V, positive	splash10-014l-9000000000-32932848b2cfead29a00	2020-07-22	View Spectrum
MS/MS	LC-MS/MS Spectrum - QTOF 30V, positive	splash10-014l-9000000000-1c834a91a5adc20fba1b	2020-07-22	View Spectrum
MS/MS	LC-MS/MS Spectrum - QTOF 33V, positive	splash10-014i-9000000000-a2f926fa84c5b56fcb75	2020-07-22	View Spectrum
MS/MS	LC-MS/MS Spectrum - QTOF 35V, positive	splash10-014i-9000000000-8f6557af39a7b179151b	2020-07-22	View Spectrum
MS/MS	LC-MS/MS Spectrum - QTOF 40V, positive	splash10-014i-9000000000-43574a299eb0ad2a948a	2020-07-22	View Spectrum
MS/MS	LC-MS/MS Spectrum - QTOF 45V, positive	splash10-0uy0-9000000000-b9b823b53494f7b464de	2020-07-22	View Spectrum
MS/MS	LC-MS/MS Spectrum - n/a 9V, positive	splash10-00di-2900000000-b3f7ed42e0410d07d1cc	2020-07-22	View Spectrum
MS/MS	LC-MS/MS Spectrum - n/a 9V, positive	splash10-0006-9000000000-e4b899ed0c9972aba84a	2020-07-22	View Spectrum
MS/MS	LC-MS/MS Spectrum - Orbitrap 1V, positive	splash10-00di-0900000000-cfe6a185ea4382b7d825	2020-07-22	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-000i-3900000000-82d3ea499e49a07dc9f5	2016-08-03	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-000b-9700000000-964c725a4c63566fc458	2016-08-03	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-0002-9000000000-cdc0027ea13905c59bed	2016-08-03	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-000i-3900000000-4c096ad99ce685693f0c	2016-08-03	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-0006-9300000000-519730edd99eab09801c	2016-08-03	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-0006-9000000000-d0cfac43ffd18d6c4a42	2016-08-03	View Spectrum

NMR

Type	Description	View
1D NMR	¹H NMR Spectrum (1D, 90 MHz, CDCl₃, experimental)	Spectrum
1D NMR	¹³C NMR Spectrum (1D, 25.16 MHz, CDCl₃, experimental)	Spectrum
1D NMR	¹³C NMR Spectrum (1D, 100 MHz, D₂O, predicted)	Spectrum
1D NMR	¹H NMR Spectrum (1D, 100 MHz, D₂O, predicted)	Spectrum
1D NMR	¹³C NMR Spectrum (1D, 1000 MHz, D₂O, predicted)	Spectrum
1D NMR	¹H NMR Spectrum (1D, 1000 MHz, D₂O, predicted)	Spectrum
1D NMR	¹³C NMR Spectrum (1D, 200 MHz, D₂O, predicted)	Spectrum
1D NMR	¹H NMR Spectrum (1D, 200 MHz, D₂O, predicted)	Spectrum
1D NMR	¹³C NMR Spectrum (1D, 300 MHz, D₂O, predicted)	Spectrum
1D NMR	¹H NMR Spectrum (1D, 300 MHz, D₂O, predicted)	Spectrum
1D NMR	¹³C NMR Spectrum (1D, 400 MHz, D₂O, predicted)	Spectrum
1D NMR	¹H NMR Spectrum (1D, 400 MHz, D₂O, predicted)	Spectrum
1D NMR	¹³C NMR Spectrum (1D, 500 MHz, D₂O, predicted)	Spectrum
1D NMR	¹H NMR Spectrum (1D, 500 MHz, D₂O, predicted)	Spectrum
1D NMR	¹³C NMR Spectrum (1D, 600 MHz, D₂O, predicted)	Spectrum
1D NMR	¹H NMR Spectrum (1D, 600 MHz, D₂O, predicted)	Spectrum
1D NMR	¹³C NMR Spectrum (1D, 700 MHz, D₂O, predicted)	Spectrum
1D NMR	¹H NMR Spectrum (1D, 700 MHz, D₂O, predicted)	Spectrum
1D NMR	¹³C NMR Spectrum (1D, 800 MHz, D₂O, predicted)	Spectrum
1D NMR	¹H NMR Spectrum (1D, 800 MHz, D₂O, predicted)	Spectrum
1D NMR	¹³C NMR Spectrum (1D, 900 MHz, D₂O, predicted)	Spectrum
1D NMR	¹H NMR Spectrum (1D, 900 MHz, D₂O, predicted)	Spectrum

Pathways

Not Available

Protein Targets

Enzymes

Not Available

Transporters

Not Available

Metal Bindings

Not Available

Receptors

Not Available

Transcriptional Factors

Not Available

Concentrations Data

Not Available

External Links

HMDB ID

HMDB0041607

DrugBank ID

DB11304

Phenol Explorer Compound ID

Not Available

FoodDB ID

FDB021762

KNApSAcK ID

C00055732

Chemspider ID

13848467

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Phenoxyethanol

METLIN ID

Not Available

PubChem Compound

31236

PDB ID

268

ChEBI ID

64275

References

General References

Rice S, Koziel JA: Characterizing the Smell of Marijuana by Odor Impact of Volatile Compounds: An Application of Simultaneous Chemical and Sensory Analysis. PLoS One. 2015 Dec 10;10(12):e0144160. doi: 10.1371/journal.pone.0144160. eCollection 2015. [PubMed:26657499 ]
Schmuck G, Steffens W, Bomhard E: 2-Phenoxyethanol: a neurotoxicant? Arch Toxicol. 2000 Jul;74(4-5):281-7. doi: 10.1007/s002040000110. [PubMed:10959804 ]
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. doi: 10.1007/s002040050586. [PubMed:10207615 ]

Showing Compound Card for 2-Phenoxyethanol (CDB000516)

Structure for CDB000516 (2-Phenoxyethanol)