Livestock Metabolome Database: Showing metabocard for Benzyl alcohol (LMDB00416)

Identification Taxonomy Ontology Physical properties Spectra Biological properties Concentrations Links References XML

Record Information

Version

1.0

Creation Date

2016-07-13 19:49:21 UTC

Update Date

2016-09-23 18:45:24 UTC

Lmdb

LMDB00416

Secondary Accession Numbers

None

Metabolite Identification

Common Name

Benzyl alcohol

Description

Benzyl 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 animal 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

MOL SDF 3D-SDF PDB SMILES InChI View 3D Structure

Synonyms

Value	Source
(Hydroxymethyl)benzene	ChEBI
Alcoholum benzylicum	ChEBI
Alcool benzylique	ChEBI
alpha-Hydroxytoluene	ChEBI
alpha-Toluenol	ChEBI
Aromatic alcohol	ChEBI
Benzenecarbinol	ChEBI
Benzenemethanol	ChEBI
Benzylalkohol	ChEBI
Benzylic alcohol	ChEBI
Hydroxymethylbenzene	ChEBI
Phenylcarbinol	ChEBI
Phenylmethanol	ChEBI
Phenylmethyl alcohol	ChEBI
Ulesfia	Kegg
a-Hydroxytoluene	Generator
Α-hydroxytoluene	Generator
a-Toluenol	Generator
Α-toluenol	Generator
Alcohol, benzyl	MeSH
.alpha.-hydroxytoluene	HMDB
.alpha.-toluenol	HMDB
Aromatic primary alcohol	HMDB
Bentalol	HMDB
Benzal alcohol	HMDB
Benzenmethanol	HMDB
Benzoyl alcohol	HMDB
Benzyl alkohol	HMDB
Benzyl-alcohol	HMDB
BenzylAlcohol	HMDB
Benzylicum	HMDB
Caswell no. 081F	HMDB
Enzylalcohol	HMDB
Euxyl K 100	HMDB
Hydroxytoluene	HMDB
Itch-X	HMDB
MBN	HMDB
Methanol benzene	HMDB
Phenolcarbinol	HMDB
Phenylcarbinolum	HMDB
Sunmorl BK 20	HMDB
TB 13g	HMDB
Benzyl alcohol	HMDB
Benzylalcohol	HMDB

Chemical Formula

C₇H₈O

Average Molecular Weight

108.1378

Monoisotopic Molecular Weight

108.057514878

IUPAC Name

phenylmethanol

Traditional Name

benzyl alcohol

CAS Registry Number

100-51-6

SMILES

OCC1=CC=CC=C1

InChI Identifier

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

InChI Key

WVDDGKGOMKODPV-UHFFFAOYSA-N

Chemical Taxonomy

Description

belongs to the class of organic compounds known as benzyl alcohols. These are organic compounds containing the phenylmethanol substructure.

Kingdom

Organic compounds

Super Class

Benzenoids

Class

Benzene and substituted derivatives

Sub Class

Benzyl alcohols

Direct Parent

Benzyl alcohols

Alternative Parents

Substituents

Benzyl alcohol
Organic oxygen compound
Hydrocarbon derivative
Aromatic alcohol
Primary alcohol
Organooxygen compound
Alcohol
Aromatic homomonocyclic compound

Molecular Framework

Aromatic homomonocyclic compounds

External Descriptors

benzyl alcohols (CHEBI:17987 )
an aromatic compound (BENZYL-ALCOHOL )

Ontology

Status

Detected but not Quantified

Origin

Not Available

Biofunction

Not Available

Application

Not Available

Cellular locations

Not Available

Physical Properties

State

Not Available

Experimental Properties

Property	Value	Reference
Melting Point	Not Available	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	1.07	ALOGPS
logP	1.21	ChemAxon
logS	-0.61	ALOGPS
pKa (Strongest Acidic)	15.02	ChemAxon
pKa (Strongest Basic)	-2.8	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	1	ChemAxon
Hydrogen Donor Count	1	ChemAxon
Polar Surface Area	20.23 Å²	ChemAxon
Rotatable Bond Count	1	ChemAxon
Refractivity	32.87 m³·mol⁻¹	ChemAxon
Polarizability	11.89 Å³	ChemAxon
Number of Rings	1	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	Yes	ChemAxon
Veber's Rule	Yes	ChemAxon
MDDR-like Rule	Yes	ChemAxon

Spectra

Spectrum Type	Description	Splash Key	View
GC-MS	GC-MS Spectrum - GC-MS (1 TMS)	splash10-00ko-6900000000-a9d668ecd37a1579a6fe	Spectrum
GC-MS	GC-MS Spectrum - EI-B (Non-derivatized)	splash10-056r-9400000000-77cec715500da9c57a84	Spectrum
GC-MS	GC-MS Spectrum - EI-B (Non-derivatized)	splash10-056r-9400000000-8dc38068387df3fa06aa	Spectrum
GC-MS	GC-MS Spectrum - EI-B (Non-derivatized)	splash10-056r-9300000000-fb124b56257906cce9f1	Spectrum
GC-MS	GC-MS Spectrum - EI-B (Non-derivatized)	splash10-056r-9400000000-7a77e67486ae3b2dd855	Spectrum
GC-MS	GC-MS Spectrum - EI-B (Non-derivatized)	splash10-056r-9400000000-dd0878988e7c2d9a5431	Spectrum
GC-MS	GC-MS Spectrum - GC-MS (Non-derivatized)	splash10-00ko-6900000000-a9d668ecd37a1579a6fe	Spectrum
GC-MS	GC-MS Spectrum - GC-EI-TOF (Non-derivatized)	splash10-0006-8900000000-c256b0b7a0755f08ac64	Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive	splash10-054o-9200000000-a9f7c0f39c81d478c0d4	Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (1 TMS) - 70eV, Positive	splash10-00dl-9300000000-e1cfa5e819f61adf9df2	Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive	Not Available	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - Quattro_QQQ 10V, N/A (Annotated)	splash10-0a4i-9500000000-2a82c3dd7c6871f61c34	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - Quattro_QQQ 25V, N/A (Annotated)	splash10-0006-9000000000-ad1762d5292c30b29bbd	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - Quattro_QQQ 40V, N/A (Annotated)	splash10-0006-9000000000-3c8d4c630cf42e3bfd3f	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - EI-B (HITACHI RMU-7M) , Positive	splash10-056r-9400000000-c4dcb2148958f946cd01	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - EI-B (HITACHI RMU-6M) , Positive	splash10-056r-9400000000-e17e577dbe4546313a91	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - EI-B (JEOL JMS-01-SG-2) , Positive	splash10-056r-9300000000-fb124b56257906cce9f1	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - EI-B (HITACHI M-80) , Positive	splash10-056r-9400000000-47b3605316c57e02b84f	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - EI-B (HITACHI M-80B) , Positive	splash10-056r-9400000000-dd0878988e7c2d9a5431	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - , positive	splash10-0a4i-3900000000-4d1bf15f6cf8f65bf0a6	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - 35V, Negative	splash10-0a4i-1900000000-866ce230a3fc1ead8353	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-0a4i-0900000000-3a71c23796a048eb999c	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-0a4i-1900000000-40737e7bdf548d714249	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-0uxr-9100000000-23e82914cfa9372ecafc	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-0a4i-1900000000-17f95f5a398b5850abb2	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-0a6r-7900000000-733d283e0916e755a736	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-004i-9000000000-d0c6e5fc39516ee594b4	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-0006-9000000000-d0618c117a092a2f7241	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-0006-9000000000-b65b57d5b2389beaf5f2	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-00kf-9000000000-a2b78129c0731eee69f4	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-004i-9200000000-72dc044d901c3dfcec51	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-004i-9000000000-fc58e0949de9ca4842ff	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-004i-9000000000-fc58e0949de9ca4842ff	Spectrum
MS	Mass Spectrum (Electron Ionization)	splash10-056r-9400000000-a8f1fd78fa3f8781f296	Spectrum
1D NMR	1H NMR Spectrum	Not Available	Spectrum
1D NMR	1H NMR Spectrum	Not Available	Spectrum
1D NMR	13C NMR Spectrum	Not Available	Spectrum
1D NMR	1H NMR Spectrum	Not Available	Spectrum
1D NMR	13C NMR Spectrum	Not Available	Spectrum
1D NMR	1H NMR Spectrum	Not Available	Spectrum
1D NMR	13C NMR Spectrum	Not Available	Spectrum
1D NMR	1H NMR Spectrum	Not Available	Spectrum
1D NMR	13C NMR Spectrum	Not Available	Spectrum
1D NMR	1H NMR Spectrum	Not Available	Spectrum
1D NMR	13C NMR Spectrum	Not Available	Spectrum
1D NMR	1H NMR Spectrum	Not Available	Spectrum
1D NMR	13C NMR Spectrum	Not Available	Spectrum
1D NMR	1H NMR Spectrum	Not Available	Spectrum
1D NMR	13C NMR Spectrum	Not Available	Spectrum
1D NMR	1H NMR Spectrum	Not Available	Spectrum
1D NMR	13C NMR Spectrum	Not Available	Spectrum
1D NMR	1H NMR Spectrum	Not Available	Spectrum
1D NMR	13C NMR Spectrum	Not Available	Spectrum
1D NMR	1H NMR Spectrum	Not Available	Spectrum
1D NMR	13C NMR Spectrum	Not Available	Spectrum
1D NMR	1H NMR Spectrum	Not Available	Spectrum
1D NMR	13C NMR Spectrum	Not Available	Spectrum
1D NMR	1H NMR Spectrum	Not Available	Spectrum
1D NMR	13C NMR Spectrum	Not Available	Spectrum
2D NMR	[1H,13C] 2D NMR Spectrum	Not Available	Spectrum