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Record Information
Version3.6
Creation Date2006-05-22 15:12:34 UTC
Update Date2016-02-11 01:06:03 UTC
HMDB IDHMDB03119
Secondary Accession NumbersNone
Metabolite Identification
Common NameBenzyl alcohol
DescriptionBenzyl Alcohol 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 injection. Also, it is used in the manufacture of other benzyl compounds, as a pharmaceutical aid, and in perfumery and flavoring. Benzyl Alcohol is an aromatic alcohol used in a wide variety of cosmetic formulations as a fragrance component, preservative, solvent, and viscosity-decreasing agent. Benzyl Alcohol is metabolized to Benzoic Acid, which reacts with glycine and excreted as hippuric acid in the human body. Acceptable daily intakes were established by the World Health Organization at 5 mg/kg for Benzyl Alcohol. No adverse effects of benzyl alcohol have been seen in chronic exposure animal studies using rats and mice. Effects of Benzyl Alcohol 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%. Benzyl Alcohol could be used safely at concentrations up to 5%, but that 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. The limited body exposure, the duration of use, and the frequency of use are considered in concluding that the nonimmunologic reactions would not be a concern. 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 ).
Structure
Thumb
Synonyms
ValueSource
(Hydroxymethyl)benzeneChEBI
Alcoholum benzylicumChEBI
Alcool benzyliqueChEBI
alpha-HydroxytolueneChEBI
alpha-ToluenolChEBI
Aromatic alcoholChEBI
BenzenecarbinolChEBI
BenzenemethanolChEBI
BenzylalkoholChEBI
Benzylic alcoholChEBI
HydroxymethylbenzeneChEBI
PhenylcarbinolChEBI
Phenylmethyl alcoholChEBI
a-HydroxytolueneGenerator
α-hydroxytolueneGenerator
a-ToluenolGenerator
α-toluenolGenerator
.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
Chemical FormulaC7H8O
Average Molecular Weight108.1378
Monoisotopic Molecular Weight108.057514878
IUPAC Namephenylmethanol
Traditional Namebenzyl alcohol
CAS Registry Number100-51-6
SMILES
OCC1=CC=CC=C1
InChI Identifier
InChI=1S/C7H8O/c8-6-7-4-2-1-3-5-7/h1-5,8H,6H2
InChI KeyInChIKey=WVDDGKGOMKODPV-UHFFFAOYSA-N
Chemical Taxonomy
DescriptionThis compound 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
  • Hydrocarbon derivative
  • Aromatic alcohol
  • Primary alcohol
  • Organooxygen compound
  • Alcohol
  • Aromatic homomonocyclic compound
Molecular FrameworkAromatic homomonocyclic compounds
External Descriptors
Ontology
StatusDetected but not Quantified
Origin
  • Drug
BiofunctionNot Available
ApplicationNot Available
Cellular locationsNot Available
Physical Properties
StateLiquid
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
Water Solubility26.8 mg/mLALOGPS
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 Å2ChemAxon
Rotatable Bond Count1ChemAxon
Refractivity32.87 m3·mol-1ChemAxon
Polarizability11.89 Å3ChemAxon
Number of Rings1ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Spectra
Spectra
Spectrum TypeDescriptionSplash Key
GC-MSGC-MS Spectrum - GC-MS (1 TMS)splash10-00ko-6900000000-a9d668ecd37a1579a6feView in MoNA
GC-MSGC-MS Spectrum - GC-MSNot Available
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 10V, N/A (Annotated)splash10-0a4i-9500000000-2a82c3dd7c6871f61c34View in MoNA
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 25V, N/A (Annotated)splash10-0006-9000000000-ad1762d5292c30b29bbdView in MoNA
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 40V, N/A (Annotated)splash10-0006-9000000000-3c8d4c630cf42e3bfd3fView in MoNA
LC-MS/MSLC-MS/MS Spectrum - EI-B (HITACHI RMU-7M) , Positivesplash10-056r-9400000000-c4dcb2148958f946cd01View in MoNA
LC-MS/MSLC-MS/MS Spectrum - EI-B (HITACHI RMU-6M) , Positivesplash10-056r-9400000000-e17e577dbe4546313a91View in MoNA
LC-MS/MSLC-MS/MS Spectrum - EI-B (JEOL JMS-01-SG-2) , Positivesplash10-056r-9300000000-fb124b56257906cce9f1View in MoNA
LC-MS/MSLC-MS/MS Spectrum - EI-B (HITACHI M-80) , Positivesplash10-056r-9400000000-47b3605316c57e02b84fView in MoNA
LC-MS/MSLC-MS/MS Spectrum - EI-B (HITACHI M-80B) , Positivesplash10-056r-9400000000-dd0878988e7c2d9a5431View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0a4i-0900000000-3a71c23796a048eb999cView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0a4i-1900000000-40737e7bdf548d714249View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0uxr-9100000000-23e82914cfa9372ecafcView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0a4i-1900000000-17f95f5a398b5850abb2View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0a6r-7900000000-733d283e0916e755a736View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-004i-9000000000-d0c6e5fc39516ee594b4View in MoNA
MSMass Spectrum (Electron Ionization)splash10-056r-9400000000-a8f1fd78fa3f8781f296View in MoNA
1D NMR1H NMR SpectrumNot Available
1D NMR1H NMR SpectrumNot Available
1D NMR13C NMR SpectrumNot Available
2D NMR[1H,13C] 2D NMR SpectrumNot Available
Biological Properties
Cellular LocationsNot Available
Biofluid Locations
  • Feces
  • Saliva
Tissue LocationNot Available
PathwaysNot Available
Normal Concentrations
BiofluidStatusValueAgeSexConditionReferenceDetails
FecesDetected but not QuantifiedNot ApplicableAdult (>18 years old)Both
Normal
details
SalivaDetected but not QuantifiedNot ApplicableAdult (>18 years old)Not SpecifiedNormal details
Abnormal Concentrations
BiofluidStatusValueAgeSexConditionReferenceDetails
FecesDetected but not QuantifiedNot ApplicableAdult (>18 years old)Both
Campylobacter jejuni infection
details
FecesDetected but not QuantifiedNot ApplicableAdult (>18 years old)Both
Clostridium difficile infection
details
FecesDetected but not QuantifiedNot ApplicableAdult (>18 years old)Both
Ulcerative Colitis
details
Associated Disorders and Diseases
Disease ReferencesNone
Associated OMIM IDsNone
DrugBank IDNot Available
DrugBank Metabolite IDNot Available
Phenol Explorer Compound IDNot Available
Phenol Explorer Metabolite IDNot Available
FoodDB IDFDB008745
KNApSAcK IDC00029811
Chemspider ID13860335
KEGG Compound IDC00556
BioCyc ID34-DIMETHYLBENZYL-ALCOHOL
BiGG IDNot Available
Wikipedia LinkNot Available
NuGOwiki LinkHMDB03119
Metagene LinkHMDB03119
METLIN IDNot Available
PubChem Compound244
PDB IDNot Available
ChEBI ID17987
References
Synthesis ReferenceXu, Hua-Long; Huang, Jing-Jing; Yang, Xin-Yan; Du, Jun-Ming; Shen, Jiang; Shen, Wei. Consecutive hydrogenation of methyl benzoate to non-chloride benzyl alcohol over K-MnO/g-Al2O3 and Cu/SiO2 catalysts. Huaxue Xuebao (2006), 64(16), 1615-1621.
Material Safety Data Sheet (MSDS)Download (PDF)
General References
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