Benzyl Alcohol

Basic Info

Common NameBenzyl Alcohol(F06942)
2D Structure
FRCD IDF06942
CAS Number100-51-6
PubChem CID244
FormulaC7H8O
IUPAC Name

phenylmethanol

InChI Key

WVDDGKGOMKODPV-UHFFFAOYSA-N

InChI

InChI=1S/C7H8O/c8-6-7-4-2-1-3-5-7/h1-5,8H,6H2

Canonical SMILES

C1=CC=C(C=C1)CO

Isomeric SMILES

C1=CC=C(C=C1)CO

WikipediaBenzyl Alcohol
Synonyms
        
            Hydroxytoluene
        
            benzyl alcohol
        
            phenylmethanol
        
            benzenemethanol
        
            100-51-6
        
            phenylcarbinol
        
            Benzoyl alcohol
        
            Benzenecarbinol
        
            Phenylmethyl alcohol
        
            alpha-Toluenol
Classifies
                

                  
                    Food Additive
Update DateNov 13, 2018 17:07

Chemical Taxonomy

KingdomOrganic compounds
SuperclassBenzenoids
ClassBenzene and substituted derivatives
SubclassBenzyl alcohols
Intermediate Tree NodesNot available
Direct ParentBenzyl alcohols
Alternative Parents
Molecular FrameworkAromatic homomonocyclic compounds
SubstituentsBenzyl alcohol - Organic oxygen compound - Hydrocarbon derivative - Aromatic alcohol - Primary alcohol - Organooxygen compound - Alcohol - Aromatic homomonocyclic compound
DescriptionThis compound belongs to the class of organic compounds known as benzyl alcohols. These are organic compounds containing the phenylmethanol substructure.

Properties

Property NameProperty Value
Molecular Weight108.14
Hydrogen Bond Donor Count1
Hydrogen Bond Acceptor Count1
Rotatable Bond Count1
Complexity55.4
Monoisotopic Mass108.058
Exact Mass108.058
XLogP1.1
Formal Charge0
Heavy Atom Count8
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+0.9698
Human Intestinal AbsorptionHIA+0.9906
Caco-2 PermeabilityCaco2+0.8859
P-glycoprotein SubstrateNon-substrate0.8373
P-glycoprotein InhibitorNon-inhibitor0.9803
Non-inhibitor0.9629
Renal Organic Cation TransporterNon-inhibitor0.8259
Distribution
Subcellular localizationMitochondria0.4584
Metabolism
CYP450 2C9 SubstrateNon-substrate0.7995
CYP450 2D6 SubstrateNon-substrate0.9234
CYP450 3A4 SubstrateNon-substrate0.8408
CYP450 1A2 InhibitorInhibitor0.5434
CYP450 2C9 InhibitorNon-inhibitor0.9285
CYP450 2D6 InhibitorNon-inhibitor0.9623
CYP450 2C19 InhibitorNon-inhibitor0.7859
CYP450 3A4 InhibitorNon-inhibitor0.9558
CYP Inhibitory PromiscuityLow CYP Inhibitory Promiscuity0.8458
Excretion
Toxicity
Human Ether-a-go-go-Related Gene InhibitionWeak inhibitor0.8998
Non-inhibitor0.9625
AMES ToxicityNon AMES toxic0.9645
CarcinogensNon-carcinogens0.5381
Fish ToxicityLow FHMT0.5083
Tetrahymena Pyriformis ToxicityHigh TPT0.8899
Honey Bee ToxicityHigh HBT0.7286
BiodegradationReady biodegradable0.8774
Acute Oral ToxicityIII0.8069
Carcinogenicity (Three-class)Non-required0.7056
Model Value Unit
Absorption
Aqueous solubility-0.4622LogS
Caco-2 Permeability1.8590LogPapp, cm/s
Distribution
Metabolism
Excretion
Toxicity
Rat Acute Toxicity1.9753LD50, mol/kg
Fish Toxicity1.6025pLC50, mg/L
Tetrahymena Pyriformis Toxicity-0.7048pIGC50, ug/L

References

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Benzyl alcohol induces a reversible fragmentation of the Golgi apparatus and inhibits membrane trafficking between endosomes and the trans-Golgi network.Exp Cell Res2017 Aug 128450044
Characterization of the recombinant Brettanomyces anomalus β-glucosidase and its potential for bioflavouring.J Appl Microbiol2016 Sep27277532
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Effect of Raw Material, Pressing and Glycosidase on the Volatile CompoundComposition of Wine Made From Goji Berries.Molecules2016 Oct 227706098
Degradation of 3-phenoxybenzoic acid by a filamentous fungus Aspergillus oryzae M-4 strain with self-protection transformation.Appl Microbiol Biotechnol2016 Nov27678114
De Novo Synthesis of Benzenoid Compounds by the Yeast Hanseniaspora vineaeIncreases the Flavor Diversity of Wines.J Agric Food Chem2016 Jun 827193819
Effect of yeast assimilable nitrogen on the synthesis of phenolic aroma compoundsby Hanseniaspora vineae strains.Yeast2016 Jul26945700
Fate and control of pathogenic and spoilage micro-organisms in orange blossom(Citrus aurantium) and rose flower (Rosa centifolia) hydrosols.J Appl Microbiol2016 Dec27618523
Metabolism of (Z)-(1R,3R)-Profluthrin in Rats.J Agric Food Chem2015 Oct 726357989
Effect of pulsed electric fields on the flavour profile of red-fleshed sweetcherries (Prunus avium var. Stella).Molecules2015 Mar 2325806548
Benzyl alcohol protects against acetaminophen hepatotoxicity by inhibiting cytochrome P450 enzymes but causes mitochondrial dysfunction and cell death at higher doses.Food Chem Toxicol2015 Dec26522885
Sitophilus granarius L. (Coleoptera) Toxicity and Biological Activities of theEssential Oils of Tanacetum macrophyllum (Waldst. & Kit.) Schultz Bip.J Oleo Sci201526179008
Topical ivermectin 0.5% lotion for treatment of head lice.Ann Pharmacother2013 Sep24259731
Waterpipe smoking: analysis of the aroma profile of flavored waterpipe tobaccos.Talanta2013 Oct 1524054646
Qualitative and quantitative measures of various compounded formulations of 17-alpha hydroxyprogesterone caproate.Am J Obstet Gynecol2013 Jun23453884
Environmental and seasonal influences on red raspberry flavour volatiles andidentification of quantitative trait loci (QTL) and candidate genes.Theor Appl Genet2013 Jan22890807
Frequency of positive patch test reactions to preservatives: The Australianexperience.Australas J Dermatol2013 Feb23083503
Formation of complex natural flavours by biotransformation of apple pomace withbasidiomycetes.Food Chem2013 Dec 123871045
Volatiles from apple trees infested with light brown apple moth larvae attractthe parasitoid Dolichogenidia tasmanica.J Agric Food Chem2012 Sep 2622950817