2-Phenoxyethanol
(right click,save link as to download,it is a temp file,please download as soon as possible, you can also use CTRL+S to save the whole html page)
Basic Info
Common Name | 2-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 ID | F05120 |
CAS Number | 122-99-6 |
PubChem CID | 31236 |
Formula | C8H10O2 |
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 Date | Nov 13, 2018 17:07 |
Chemical Taxonomy
Kingdom | Organic compounds |
Superclass | Benzenoids |
Class | Phenol ethers |
Subclass | Not available |
Intermediate Tree Nodes | Not available |
Direct Parent | Phenol ethers |
Alternative Parents | |
Molecular Framework | Aromatic homomonocyclic compounds |
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 |
Description | This 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 Name | Property Value |
---|---|
Molecular Weight | 138.166 |
Hydrogen Bond Donor Count | 1 |
Hydrogen Bond Acceptor Count | 2 |
Rotatable Bond Count | 3 |
Complexity | 77.3 |
Monoisotopic Mass | 138.068 |
Exact Mass | 138.068 |
XLogP | 1.2 |
Formal Charge | 0 |
Heavy Atom Count | 10 |
Defined Atom Stereocenter Count | 0 |
Undefined Atom Stereocenter Count | 0 |
Defined Bond Stereocenter Count | 0 |
Undefined Bond Stereocenter Count | 0 |
Isotope Atom Count | 0 |
Covalently-Bonded Unit Count | 1 |
ADMET
Model | Result | Probability |
---|---|---|
Absorption | ||
Blood-Brain Barrier | BBB+ | 0.8292 |
Human Intestinal Absorption | HIA+ | 0.9834 |
Caco-2 Permeability | Caco2+ | 0.7609 |
P-glycoprotein Substrate | Non-substrate | 0.7000 |
P-glycoprotein Inhibitor | Non-inhibitor | 0.6856 |
Non-inhibitor | 0.6176 | |
Renal Organic Cation Transporter | Non-inhibitor | 0.7555 |
Distribution | ||
Subcellular localization | Mitochondria | 0.8297 |
Metabolism | ||
CYP450 2C9 Substrate | Non-substrate | 0.8203 |
CYP450 2D6 Substrate | Non-substrate | 0.8053 |
CYP450 3A4 Substrate | Non-substrate | 0.7146 |
CYP450 1A2 Inhibitor | Non-inhibitor | 0.7318 |
CYP450 2C9 Inhibitor | Non-inhibitor | 0.9482 |
CYP450 2D6 Inhibitor | Non-inhibitor | 0.9613 |
CYP450 2C19 Inhibitor | Non-inhibitor | 0.7656 |
CYP450 3A4 Inhibitor | Non-inhibitor | 0.9650 |
CYP Inhibitory Promiscuity | Low CYP Inhibitory Promiscuity | 0.8578 |
Excretion | ||
Toxicity | ||
Human Ether-a-go-go-Related Gene Inhibition | Weak inhibitor | 0.7361 |
Non-inhibitor | 0.8449 | |
AMES Toxicity | Non AMES toxic | 0.9133 |
Carcinogens | Non-carcinogens | 0.8174 |
Fish Toxicity | Low FHMT | 0.8235 |
Tetrahymena Pyriformis Toxicity | Low TPT | 0.7141 |
Honey Bee Toxicity | High HBT | 0.7444 |
Biodegradation | Ready biodegradable | 0.8235 |
Acute Oral Toxicity | III | 0.8740 |
Carcinogenicity (Three-class) | Non-required | 0.5595 |
Model | Value | Unit |
---|---|---|
Absorption | ||
Aqueous solubility | -0.7728 | LogS |
Caco-2 Permeability | 1.3422 | LogPapp, cm/s |
Distribution | ||
Metabolism | ||
Excretion | ||
Toxicity | ||
Rat Acute Toxicity | 2.0085 | LD50, mol/kg |
Fish Toxicity | 2.4117 | pLC50, mg/L |
Tetrahymena Pyriformis Toxicity | -0.6666 | pIGC50, ug/L |
References
Title | Journal | Date | Pubmed ID |
---|---|---|---|
Comparative Evaluation of Key Aroma-Active Compounds in Raw and Cooked Red Mullet(Mullus barbatus) by Aroma Extract Dilution Analysis. | J Agric Food Chem | 2017 Sep 27 | 28862440 |
Ethylhexylglycerin Impairs Membrane Integrity and Enhances the Lethal Effect ofPhenoxyethanol. | PLoS One | 2016 Oct 26 | 27783695 |
Escherichia coli β-galactosidase-catalyzed synthesis of 2-phenoxyethanol galactoside and its characterization. | Bioprocess Biosyst Eng | 2015 Feb | 25217153 |
The Toluene o-Xylene Monooxygenase Enzymatic Activity for the Biosynthesis ofAromatic Antioxidants. | PLoS One | 2015 Apr 27 | 25915063 |
Hypersensitivity reactions to vaccine constituents: a case series and review ofthe literature. | Dermatitis | 2012 May-Jun | 22653170 |
In vitro induction of apoptosis vs. necrosis by widely used preservatives:2-phenoxyethanol, a mixture of isothiazolinones, imidazolidinyl urea and1,2-pentanediol. | Biochem Pharmacol | 2002 Feb 1 | 11853695 |
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
- 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
- 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 ]