Showing Compound Card for alpha-Toluenol (CDB000681)

Jump To Section:
IdentificationTaxonomyOntologyPhysical propertiesSpectraProtein targetPathwaysConcentrationsLinksReferencesXML
Record Information
Version1.0
Created at2020-03-19 00:50:51 UTC
Updated at2020-12-07 19:07:40 UTC
CannabisDB IDCDB000681
Secondary Accession NumbersNot Available
Cannabis Compound Identification
Common Namealpha-Toluenol
Descriptionα-Toluenol or benzyl alcohol, belongs to the class of organic compounds known as benzyl alcohols. These are organic compounds containing the phenylmethanol substructure. α-Toluenol is a colorless liquid with a sharp burning taste and slight odor. It is used as a local anesthetic and to reduce pain associated with lidocaine injections. Also, it is used in the manufacture of other benzyl compounds, as a pharmaceutical aid, and in perfumery and flavoring. α-Toluenol is an aromatic alcohol used in a wide variety of cosmetic formulations as a fragrance component, preservative, solvent, and viscosity-decreasing agent. α-Toluenol is metabolized to benzoic acid, which reacts with glycine and is excreted as hippuric acid from the human body. Acceptable daily intakes were established by the World Health Organization at 5 mg/kg for α-Toluenol. No adverse effects of α-toluenol have been seen in chronic exposure animal studies using rats and mice. Effects of α-toluenol in chronic exposure animal studies are limited to reduced feed intake and reduced growth. Some differences have been noted in one reproductive toxicity study using mice, but these were limited to lower maternal body weights and decreased mean litter weights. Another study also noted that fetal weight was decreased compared to controls, but a third study showed no differences between control and benzyl alcohol-treated groups. Benzyl Alcohol has been associated with an increased number of resorptions and malformations in hamsters, but there have been no reproductive or developmental toxicity findings in studies using mice and rats. Genotoxicity tests for benzyl alcohol are mostly negative, but there were some assays that were positive. Carcinogenicity studies, however, were negative. Clinical data indicates that benzyl alcohol can produce nonimmunologic contact urticaria and nonimmunologic immediate contact reactions, characterized by the appearance of wheals, erythema, and pruritis. 5% benzyl alcohol can elicit a reaction. Benzyl alcohol is not a sensitizer at 10%. It could be used safely at concentrations up to 5%, but manufacturers should consider the nonimmunologic phenomena when using benzyl alcohol in cosmetic formulations designed for infants and children. Additionally, benzyl alcohol is considered safe up to 10% for use in hair dyes. Because of the wide variety of product types in which benzyl alcohol may be used, it is likely that inhalation may be a route of exposure. The available safety tests are not considered sufficient to support the safety of benzyl alcohol in formulations where inhalation is a route of exposure. Inhalation toxicity data are needed to complete the safety assessment of benzyl alcohol where inhalation can occur. (PMID: 11766131 ). Benzyl alcohol is produced naturally by many plants and is commonly found in fruits and teas. It is found in a variety of essential oils including jasmine, hyacinth and ylang-ylang, both free and as esters and is also present in cherry, orange juice, mandarin peel oil, guava fruit, feijoa fruit, pineapple, leek, cinnamon, cloves, mustard, fermented tea, basil and red sage. Flavouring ingredient benzyl alcohol is a colorless liquid with a mild pleasant aromatic odor. It is a useful solvent due to its polarity, low toxicity, and low vapor pressure. Benzyl alcohol is found in many foods, some of which are towel gourd, cloud ear fungus, angelica, and safflower. Benzyl alcohol has been reported as a volatile component of cannabis samples (PMID: 29783790 , 26657499 ).
Structure
Thumb
MOLSDF3D-SDFPDBSMILESInChI View 3D Structure
Synonyms
ValueSource
(Hydroxymethyl)benzeneChEBI
Alcoholum benzylicumChEBI
Alcool benzyliqueChEBI
alpha-HydroxytolueneChEBI
alpha-ToluenolChEBI
Aromatic alcoholChEBI
BenzenecarbinolChEBI
BenzenemethanolChEBI
BenzylalkoholChEBI
Benzylic alcoholChEBI
HydroxymethylbenzeneChEBI
PhenylcarbinolChEBI
PhenylmethanolChEBI
Phenylmethyl alcoholChEBI
UlesfiaKegg
a-HydroxytolueneGenerator
Α-hydroxytolueneGenerator
a-ToluenolGenerator
Α-toluenolGenerator
Alcohol, benzylMeSH
.alpha.-hydroxytolueneHMDB
.alpha.-toluenolHMDB
Aromatic primary alcoholHMDB
BentalolHMDB
Benzal alcoholHMDB
BenzenmethanolHMDB
Benzoyl alcoholHMDB
Benzyl alkoholHMDB
Benzyl-alcoholHMDB
BenzylAlcoholHMDB
BenzylicumHMDB
Caswell no. 081FHMDB
EnzylalcoholHMDB
Euxyl K 100HMDB
HydroxytolueneHMDB
Itch-XHMDB
MBNHMDB
Methanol benzeneHMDB
PhenolcarbinolHMDB
PhenylcarbinolumHMDB
Sunmorl BK 20HMDB
TB 13gHMDB
Benzyl alcoholHMDB
BenzylalcoholHMDB
Chemical FormulaC7H8O
Average Molecular Weight108.14
Monoisotopic Molecular Weight108.0575
IUPAC Namephenylmethanol
Traditional Namebenzyl alcohol
CAS Registry Number1336-27-2
SMILES
OCC1=CC=CC=C1
InChI Identifier
InChI=1S/C7H8O/c8-6-7-4-2-1-3-5-7/h1-5,8H,6H2
InChI KeyWVDDGKGOMKODPV-UHFFFAOYSA-N
Chemical Taxonomy
Description Belongs to the class of organic compounds known as benzyl alcohols. These are organic compounds containing the phenylmethanol substructure.
KingdomOrganic compounds
Super ClassBenzenoids
ClassBenzene and substituted derivatives
Sub ClassBenzyl alcohols
Direct ParentBenzyl alcohols
Alternative Parents
Substituents
  • Benzyl alcohol
  • Organic oxygen compound
  • Hydrocarbon derivative
  • Aromatic alcohol
  • Primary alcohol
  • Organooxygen compound
  • Alcohol
  • Aromatic homomonocyclic compound
Molecular FrameworkAromatic homomonocyclic compounds
External Descriptors
Ontology
Physiological effect

Health effect:

Disposition

Route of exposure:

Source:

Biological location:

Role

Industrial application:

Physical Properties
StateSolid
Experimental Properties
PropertyValueReference
Melting Point-15.2 °CNot Available
Boiling PointNot AvailableNot Available
Water Solubility42.9 mg/mL at 25 °CNot Available
logP1.10HANSCH,C ET AL. (1995)
Predicted Properties
PropertyValueSource
logP1.07ALOGPS
logP1.21ChemAxon
logS-0.61ALOGPS
pKa (Strongest Acidic)15.02ChemAxon
pKa (Strongest Basic)-2.8ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count1ChemAxon
Hydrogen Donor Count1ChemAxon
Polar Surface Area20.23 ŲChemAxon
Rotatable Bond Count1ChemAxon
Refractivity32.87 m³·mol⁻¹ChemAxon
Polarizability11.89 ųChemAxon
Number of Rings1ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterNoChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleNoChemAxon
Spectra
EI-MS/GC-MS
TypeDescriptionSplash KeyView
EI-MSMass Spectrum (Electron Ionization)splash10-056r-9400000000-a8f1fd78fa3f8781f2962015-03-01View Spectrum
GC-MSBenzyl Alcohol, 1 TMS, GC-MS Spectrumsplash10-00ko-6900000000-a9d668ecd37a1579a6feSpectrum
GC-MSBenzyl Alcohol, non-derivatized, GC-MS Spectrumsplash10-056r-9400000000-77cec715500da9c57a84Spectrum
GC-MSBenzyl Alcohol, non-derivatized, GC-MS Spectrumsplash10-056r-9400000000-8dc38068387df3fa06aaSpectrum
GC-MSBenzyl Alcohol, non-derivatized, GC-MS Spectrumsplash10-056r-9300000000-fb124b56257906cce9f1Spectrum
GC-MSBenzyl Alcohol, non-derivatized, GC-MS Spectrumsplash10-056r-9400000000-7a77e67486ae3b2dd855Spectrum
GC-MSBenzyl Alcohol, non-derivatized, GC-MS Spectrumsplash10-056r-9400000000-dd0878988e7c2d9a5431Spectrum
GC-MSBenzyl Alcohol, non-derivatized, GC-MS Spectrumsplash10-00ko-6900000000-a9d668ecd37a1579a6feSpectrum
GC-MSBenzyl Alcohol, non-derivatized, GC-MS Spectrumsplash10-0006-8900000000-c256b0b7a0755f08ac64Spectrum
Predicted GC-MSBenzyl Alcohol, non-derivatized, Predicted GC-MS Spectrum - 70eV, Positivesplash10-054o-9200000000-a9f7c0f39c81d478c0d4Spectrum
Predicted GC-MSBenzyl Alcohol, 1 TMS, Predicted GC-MS Spectrum - 70eV, Positivesplash10-00dl-9300000000-e1cfa5e819f61adf9df2Spectrum
Predicted GC-MSBenzyl Alcohol, non-derivatized, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
MS/MS
TypeDescriptionSplash KeyView
MS/MSLC-MS/MS Spectrum - Quattro_QQQ 10V, N/A (Annotated)splash10-0a4i-9500000000-2a82c3dd7c6871f61c342012-07-25View Spectrum
MS/MSLC-MS/MS Spectrum - Quattro_QQQ 25V, N/A (Annotated)splash10-0006-9000000000-ad1762d5292c30b29bbd2012-07-25View Spectrum
MS/MSLC-MS/MS Spectrum - Quattro_QQQ 40V, N/A (Annotated)splash10-0006-9000000000-3c8d4c630cf42e3bfd3f2012-07-25View Spectrum
MS/MSLC-MS/MS Spectrum - EI-B (HITACHI RMU-7M) , Positivesplash10-056r-9400000000-c4dcb2148958f946cd012012-08-31View Spectrum
MS/MSLC-MS/MS Spectrum - EI-B (HITACHI RMU-6M) , Positivesplash10-056r-9400000000-e17e577dbe4546313a912012-08-31View Spectrum
MS/MSLC-MS/MS Spectrum - EI-B (JEOL JMS-01-SG-2) , Positivesplash10-056r-9300000000-fb124b56257906cce9f12012-08-31View Spectrum
MS/MSLC-MS/MS Spectrum - EI-B (HITACHI M-80) , Positivesplash10-056r-9400000000-47b3605316c57e02b84f2012-08-31View Spectrum
MS/MSLC-MS/MS Spectrum - EI-B (HITACHI M-80B) , Positivesplash10-056r-9400000000-dd0878988e7c2d9a54312012-08-31View Spectrum
MS/MSLC-MS/MS Spectrum - , positivesplash10-0a4i-3900000000-4d1bf15f6cf8f65bf0a62017-09-14View Spectrum
MS/MSLC-MS/MS Spectrum - 35V, Negativesplash10-0a4i-1900000000-866ce230a3fc1ead83532021-09-20View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0a4i-0900000000-3a71c23796a048eb999c2015-05-27View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0a4i-1900000000-40737e7bdf548d7142492015-05-27View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0uxr-9100000000-23e82914cfa9372ecafc2015-05-27View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0a4i-1900000000-17f95f5a398b5850abb22015-05-27View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0a6r-7900000000-733d283e0916e755a7362015-05-27View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-004i-9000000000-d0c6e5fc39516ee594b42015-05-27View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0006-9000000000-d0618c117a092a2f72412021-09-23View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0006-9000000000-b65b57d5b2389beaf5f22021-09-23View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-00kf-9000000000-a2b78129c0731eee69f42021-09-23View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-004i-9200000000-72dc044d901c3dfcec512021-09-24View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-004i-9000000000-fc58e0949de9ca4842ff2021-09-24View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-004i-9000000000-fc58e0949de9ca4842ff2021-09-24View Spectrum
NMR
TypeDescriptionView
1D NMR1H NMR Spectrum (1D, 500 MHz, CD3OD, experimental)Spectrum
1D NMR1H NMR Spectrum (1D, 400 MHz, CDCl3, experimental)Spectrum
1D NMR13C NMR Spectrum (1D, 15.09 MHz, CDCl3, experimental)Spectrum
1D NMR1H NMR Spectrum (1D, D2O, experimental)Spectrum
1D NMR13C NMR Spectrum (1D, D2O, experimental)Spectrum
1D NMR1H NMR Spectrum (1D, 100 MHz, D2O, predicted)Spectrum
1D NMR13C NMR Spectrum (1D, 100 MHz, D2O, predicted)Spectrum
1D NMR1H NMR Spectrum (1D, 1000 MHz, D2O, predicted)Spectrum
1D NMR13C NMR Spectrum (1D, 1000 MHz, D2O, predicted)Spectrum
1D NMR1H NMR Spectrum (1D, 200 MHz, D2O, predicted)Spectrum
1D NMR13C NMR Spectrum (1D, 200 MHz, D2O, predicted)Spectrum
1D NMR1H NMR Spectrum (1D, 300 MHz, D2O, predicted)Spectrum
1D NMR13C NMR Spectrum (1D, 300 MHz, D2O, predicted)Spectrum
1D NMR1H NMR Spectrum (1D, 400 MHz, D2O, predicted)Spectrum
1D NMR13C NMR Spectrum (1D, 400 MHz, D2O, predicted)Spectrum
1D NMR1H NMR Spectrum (1D, 500 MHz, D2O, predicted)Spectrum
1D NMR13C NMR Spectrum (1D, 500 MHz, D2O, predicted)Spectrum
1D NMR1H NMR Spectrum (1D, 600 MHz, D2O, predicted)Spectrum
1D NMR13C NMR Spectrum (1D, 600 MHz, D2O, predicted)Spectrum
1D NMR1H NMR Spectrum (1D, 700 MHz, D2O, predicted)Spectrum
1D NMR13C NMR Spectrum (1D, 700 MHz, D2O, predicted)Spectrum
1D NMR1H NMR Spectrum (1D, 800 MHz, D2O, predicted)Spectrum
1D NMR13C NMR Spectrum (1D, 800 MHz, D2O, predicted)Spectrum
1D NMR1H NMR Spectrum (1D, 900 MHz, D2O, predicted)Spectrum
1D NMR13C NMR Spectrum (1D, 900 MHz, D2O, predicted)Spectrum
2D NMR[1H, 13C]-HSQC NMR Spectrum (2D, 600 MHz, H2O, experimental)Spectrum
Pathways
Pathways
Protein Targets
EnzymesNot Available
TransportersNot Available
Metal BindingsNot Available
ReceptorsNot Available
Transcriptional FactorsNot Available
Concentrations Data
Not Available
HMDB IDHMDB0003119
DrugBank IDDB06770
Phenol Explorer Compound IDNot Available
FoodDB IDFDB008745
KNApSAcK IDC00029811
Chemspider ID13860335
KEGG Compound IDC03485
BioCyc IDBENZYL-ALCOHOL
BiGG IDNot Available
Wikipedia LinkBenzyl_Alcohol
METLIN IDNot Available
PubChem Compound244
PDB IDNot Available
ChEBI ID17987
References
General References
  1. Nair B: Final report on the safety assessment of Benzyl Alcohol, Benzoic Acid, and Sodium Benzoate. Int J Toxicol. 2001;20 Suppl 3:23-50. doi: 10.1080/10915810152630729. [PubMed:11766131 ]
  2. 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 ]
  3. Pavlovic R, Nenna G, Calvi L, Panseri S, Borgonovo G, Giupponi L, Cannazza G, Giorgi A: Quality Traits of "Cannabidiol Oils": Cannabinoids Content, Terpene Fingerprint and Oxidation Stability of European Commercially Available Preparations. Molecules. 2018 May 20;23(5). pii: molecules23051230. doi: 10.3390/molecules23051230. [PubMed:29783790 ]