Canmetcon
Record Information
Version1.0
Creation date2010-04-08 22:10:14 UTC
Update date2018-05-28 23:37:44 UTC
Primary IDFDB012553
Secondary Accession NumbersNot Available
Chemical Information
FooDB Name4-Hydroxybenzyl alcohol
DescriptionConstituent of muskmelon (Cucurbita moschata) 4-hydroxybenzyl alcohol is the cleavage product produced during the biosynthesis of the thiazole moiety of thiamine from tyrosine as part of the thiamine biosynthesis pathway. It is a derivative of benzyl alcohol which is used as a local anesthetic and to reduce pain associated with Lidocaine injectionand is 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). 4-Hydroxybenzyl alcohol is found in fruits.
CAS Number623-05-2
Structure
Thumb
Synonyms
SynonymSource
p-MethylolphenolChEBI
4-(Hydroxymethyl)phenolHMDB
4-(Hydroxymethyl)phenol (acd/name 4.0)HMDB
4-HydroxybenzenemethanolHMDB
4-MethylolphenolHMDB
a-Hydroxy-p-cresolHMDB
alpha-Hydroxy-p-cresolHMDB
b4-Hydroxy-enzenemethanolHMDB
GastrodigeninHMDB
p-(Hydroxymethyl)phenolHMDB
p-Hydroxy-benzyl alcoholHMDB
p-Hydroxybenzyl alcoholHMDB
4-Methylol phenolHMDB
4-Hydroxybenzyl alcoholChEBI
α-Hydroxy-p-cresolbiospider
4-Hydroxybenzenemethanol, 9CIdb_source
a,4-Dihydroxytoluenedb_source
alpha-Hydroxy-P-cresolHMDB
p-Hydroxymethylphenoldb_source
Predicted Properties
PropertyValueSource
Water Solubility59.8 g/LALOGPS
logP0.53ALOGPS
logP0.9ChemAxon
logS-0.32ALOGPS
pKa (Strongest Acidic)9.48ChemAxon
pKa (Strongest Basic)-2.8ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count2ChemAxon
Hydrogen Donor Count2ChemAxon
Polar Surface Area40.46 ŲChemAxon
Rotatable Bond Count1ChemAxon
Refractivity34.85 m³·mol⁻¹ChemAxon
Polarizability12.86 ųChemAxon
Number of Rings1ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Chemical FormulaC7H8O2
IUPAC name4-(hydroxymethyl)phenol
InChI IdentifierInChI=1S/C7H8O2/c8-5-6-1-3-7(9)4-2-6/h1-4,8-9H,5H2
InChI KeyBVJSUAQZOZWCKN-UHFFFAOYSA-N
Isomeric SMILESOCC1=CC=C(O)C=C1
Average Molecular Weight124.1372
Monoisotopic Molecular Weight124.0524295
Classification
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
  • 1-hydroxy-2-unsubstituted benzenoid
  • Phenol
  • Organic oxygen compound
  • Hydrocarbon derivative
  • Aromatic alcohol
  • Primary alcohol
  • Organooxygen compound
  • Alcohol
  • Aromatic homomonocyclic compound
Molecular FrameworkAromatic homomonocyclic compounds
External Descriptors
Physico-Chemical Properties - Experimental
Physico-Chemical Properties - Experimental
PropertyValueReference
Physical stateSolid
Physical DescriptionNot Available
Mass CompositionC 67.73%; H 6.50%; O 25.78%DFC
Melting PointMp 124.5-125.5°DFC
Boiling PointNot Available
Experimental Water Solubility6.7 mg/mL at 20 oCBEILSTEIN
Experimental logP0.25HANSCH,C ET AL. (1995)
Experimental pKapKa1 9.73 (25°)DFC
Isoelectric pointNot Available
ChargeNot Available
Optical RotationNot Available
Spectroscopic UV DataNot Available
DensityNot Available
Refractive IndexNot Available
Spectra
Spectra
Spectrum TypeDescriptionSplash Key
GC-MSGC-MS Spectrum - EI-B (Non-derivatized)splash10-05i1-9400000000-f08047b4457dc23151d9View in MoNA
GC-MSGC-MS Spectrum - EI-B (Non-derivatized)splash10-0gdi-0970000000-2415f3f14aceb1b2477bView in MoNA
GC-MSGC-MS Spectrum - GC-EI-TOF (Non-derivatized)splash10-00os-1930000000-4cb3e427ccd00fb05cefView in MoNA
GC-MSGC-MS Spectrum - GC-EI-TOF (Non-derivatized)splash10-004j-1930000000-8da8f2d1a4cd6945c0d2View in MoNA
GC-MSGC-MS Spectrum - GC-EI-TOF (Non-derivatized)splash10-00os-0930000000-fb426d5a8be1daafc38cView in MoNA
GC-MSGC-MS Spectrum - GC-EI-TOF (Non-derivatized)splash10-00di-9830000000-37513a80b983842a093dView in MoNA
GC-MSGC-MS Spectrum - EI-B (Non-derivatized)splash10-05i1-9400000000-f08047b4457dc23151d9View in MoNA
GC-MSGC-MS Spectrum - EI-B (Non-derivatized)splash10-0gdi-0970000000-2415f3f14aceb1b2477bView in MoNA
GC-MSGC-MS Spectrum - GC-EI-TOF (Non-derivatized)splash10-00os-1930000000-4cb3e427ccd00fb05cefView in MoNA
GC-MSGC-MS Spectrum - GC-EI-TOF (Non-derivatized)splash10-004j-1930000000-8da8f2d1a4cd6945c0d2View in MoNA
GC-MSGC-MS Spectrum - GC-EI-TOF (Non-derivatized)splash10-00os-0930000000-fb426d5a8be1daafc38cView in MoNA
GC-MSGC-MS Spectrum - GC-EI-TOF (Non-derivatized)splash10-00di-9830000000-37513a80b983842a093dView in MoNA
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-05fv-9700000000-75343ed1558a8215cd86View in MoNA
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (2 TMS) - 70eV, Positivesplash10-0fmi-8930000000-dc7e6a9414fca90c09ffView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-056r-0900000000-e86139fcdae517d0dd50View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0a4i-1900000000-23d9f02bc9bfae1b0404View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0a6r-9500000000-ef57e905020db4322452View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-00di-1900000000-08d6d0fac3014c21f4e4View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-00dl-5900000000-a615d3a76cf31c5305cfView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0006-9100000000-e8119b2a0a6f66edc346View in MoNA
ChemSpider ID122
ChEMBL IDCHEMBL202132
KEGG Compound IDC17467
Pubchem Compound ID125
Pubchem Substance IDNot Available
ChEBI IDNot Available
Phenol-Explorer IDNot Available
DrugBank IDNot Available
HMDB IDHMDB11724
CRC / DFC (Dictionary of Food Compounds) IDHHX13-K:HHX13-K
EAFUS ID1727
Dr. Duke IDNot Available
BIGG IDNot Available
KNApSAcK IDC00029533
HET IDNot Available
Flavornet IDNot Available
GoodScent IDrw1107691
SuperScent IDNot Available
Wikipedia IDNot Available
Phenol-Explorer Metabolite IDNot Available
Duplicate IDSNot Available
Old DFC IDSNot Available
Associated Foods
FoodContent Range AverageReference
FoodReference
Biological Effects and Interactions
Health Effects / BioactivitiesNot Available
EnzymesNot Available
PathwaysNot Available
MetabolismNot Available
BiosynthesisNot Available
Organoleptic Properties
Flavours
FlavorCitations
fruity
  1. The Good Scents Company (2009). Flavor and fragrance information catalog. <http://www.thegoodscentscompany.com/allprod.html> Accessed 15.10.23.
bitter
  1. The Good Scents Company (2009). Flavor and fragrance information catalog. <http://www.thegoodscentscompany.com/allprod.html> Accessed 15.10.23.
almond
  1. The Good Scents Company (2009). Flavor and fragrance information catalog. <http://www.thegoodscentscompany.com/allprod.html> Accessed 15.10.23.
sweet
  1. The Good Scents Company (2009). Flavor and fragrance information catalog. <http://www.thegoodscentscompany.com/allprod.html> Accessed 15.10.23.
coconut
  1. The Good Scents Company (2009). Flavor and fragrance information catalog. <http://www.thegoodscentscompany.com/allprod.html> Accessed 15.10.23.
Files
MSDSshow
References
Synthesis ReferenceNot Available
General ReferenceNot Available
Content Reference