BENZYL ALCOHOL (CHEM004822)

IdentificationTaxonomyBiological PropertiesPhysical PropertiesToxicity ProfileSpectraConcentrationsLinksReferencesXML
Record Information
Version1.0
Creation Date2016-05-19 01:55:18 UTC
Update Date2016-10-28 10:01:52 UTC
Accession NumberCHEM004822
Identification
Common NameBENZYL ALCOHOL
ClassSmall Molecule
DescriptionAn aromatic alcohol that consists of benzene bearing a single hydroxymethyl substituent.
Contaminant Sources
  • Cosmetic Chemicals
  • EAFUS Chemicals
  • FooDB Chemicals
  • HMDB Contaminants - Feces
  • HPV EPA Chemicals
  • OECD HPV Chemicals
  • STOFF IDENT Compounds
  • ToxCast & Tox21 Chemicals
Contaminant TypeNot Available
Chemical 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 Mass108.138 g/mol
Monoisotopic Mass108.058 g/mol
CAS Registry Number100-51-6
IUPAC Namephenylmethanol
Traditional Namebenzyl alcohol
SMILESOCC1=CC=CC=C1
InChI IdentifierInChI=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
Biological Properties
StatusDetected and Not Quantified
OriginNot Available
Cellular LocationsNot Available
Biofluid LocationsNot Available
Tissue LocationsNot Available
PathwaysNot Available
ApplicationsNot Available
Biological RolesNot Available
Chemical RolesNot Available
Physical Properties
StateNot Available
AppearanceNot Available
Experimental Properties
PropertyValue
Melting PointNot Available
Boiling PointNot Available
SolubilityNot Available
Predicted Properties
PropertyValueSource
Water Solubility26.8 g/LALOGPS
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
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterNoChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleNoChemAxon
Spectra
Spectra
Spectrum TypeDescriptionSplash KeyView
GC-MSGC-MS Spectrum - GC-MS (1 TMS)splash10-00ko-6900000000-a9d668ecd37a1579a6feSpectrum
GC-MSGC-MS Spectrum - EI-B (Non-derivatized)splash10-056r-9400000000-77cec715500da9c57a84Spectrum
GC-MSGC-MS Spectrum - EI-B (Non-derivatized)splash10-056r-9400000000-8dc38068387df3fa06aaSpectrum
GC-MSGC-MS Spectrum - EI-B (Non-derivatized)splash10-056r-9300000000-fb124b56257906cce9f1Spectrum
GC-MSGC-MS Spectrum - EI-B (Non-derivatized)splash10-056r-9400000000-7a77e67486ae3b2dd855Spectrum
GC-MSGC-MS Spectrum - EI-B (Non-derivatized)splash10-056r-9400000000-dd0878988e7c2d9a5431Spectrum
GC-MSGC-MS Spectrum - GC-MS (Non-derivatized)splash10-00ko-6900000000-a9d668ecd37a1579a6feSpectrum
GC-MSGC-MS Spectrum - GC-EI-TOF (Non-derivatized)splash10-0006-8900000000-c256b0b7a0755f08ac64Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-054o-9200000000-a9f7c0f39c81d478c0d4Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (1 TMS) - 70eV, Positivesplash10-00dl-9300000000-e1cfa5e819f61adf9df2Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, PositiveNot AvailableSpectrum
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 10V, N/A (Annotated)splash10-0a4i-9500000000-2a82c3dd7c6871f61c34Spectrum
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 25V, N/A (Annotated)splash10-0006-9000000000-ad1762d5292c30b29bbdSpectrum
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 40V, N/A (Annotated)splash10-0006-9000000000-3c8d4c630cf42e3bfd3fSpectrum
LC-MS/MSLC-MS/MS Spectrum - EI-B (HITACHI RMU-7M) , Positivesplash10-056r-9400000000-c4dcb2148958f946cd01Spectrum
LC-MS/MSLC-MS/MS Spectrum - EI-B (HITACHI RMU-6M) , Positivesplash10-056r-9400000000-e17e577dbe4546313a91Spectrum
LC-MS/MSLC-MS/MS Spectrum - EI-B (JEOL JMS-01-SG-2) , Positivesplash10-056r-9300000000-fb124b56257906cce9f1Spectrum
LC-MS/MSLC-MS/MS Spectrum - EI-B (HITACHI M-80) , Positivesplash10-056r-9400000000-47b3605316c57e02b84fSpectrum
LC-MS/MSLC-MS/MS Spectrum - EI-B (HITACHI M-80B) , Positivesplash10-056r-9400000000-dd0878988e7c2d9a5431Spectrum
LC-MS/MSLC-MS/MS Spectrum - , positivesplash10-0a4i-3900000000-4d1bf15f6cf8f65bf0a6Spectrum
LC-MS/MSLC-MS/MS Spectrum - 35V, Negativesplash10-0a4i-1900000000-866ce230a3fc1ead8353Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0a4i-0900000000-3a71c23796a048eb999cSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0a4i-1900000000-40737e7bdf548d714249Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0uxr-9100000000-23e82914cfa9372ecafcSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0a4i-1900000000-17f95f5a398b5850abb2Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0a6r-7900000000-733d283e0916e755a736Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-004i-9000000000-d0c6e5fc39516ee594b4Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0006-9000000000-d0618c117a092a2f7241Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0006-9000000000-b65b57d5b2389beaf5f2Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-00kf-9000000000-a2b78129c0731eee69f4Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-004i-9200000000-72dc044d901c3dfcec51Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-004i-9000000000-fc58e0949de9ca4842ffSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-004i-9000000000-fc58e0949de9ca4842ffSpectrum
MSMass Spectrum (Electron Ionization)splash10-056r-9400000000-a8f1fd78fa3f8781f296Spectrum
1D NMR1H NMR SpectrumNot AvailableSpectrum
1D NMR1H NMR SpectrumNot AvailableSpectrum
1D NMR13C NMR SpectrumNot AvailableSpectrum
1D NMR1H NMR SpectrumNot AvailableSpectrum
1D NMR13C NMR SpectrumNot AvailableSpectrum
1D NMR1H NMR SpectrumNot AvailableSpectrum
1D NMR13C NMR SpectrumNot AvailableSpectrum
1D NMR1H NMR SpectrumNot AvailableSpectrum
1D NMR13C NMR SpectrumNot AvailableSpectrum
1D NMR1H NMR SpectrumNot AvailableSpectrum
1D NMR13C NMR SpectrumNot AvailableSpectrum
1D NMR1H NMR SpectrumNot AvailableSpectrum
1D NMR13C NMR SpectrumNot AvailableSpectrum
1D NMR1H NMR SpectrumNot AvailableSpectrum
1D NMR13C NMR SpectrumNot AvailableSpectrum
1D NMR1H NMR SpectrumNot AvailableSpectrum
1D NMR13C NMR SpectrumNot AvailableSpectrum
1D NMR1H NMR SpectrumNot AvailableSpectrum
1D NMR13C NMR SpectrumNot AvailableSpectrum
1D NMR1H NMR SpectrumNot AvailableSpectrum
1D NMR13C NMR SpectrumNot AvailableSpectrum
1D NMR1H NMR SpectrumNot AvailableSpectrum
1D NMR13C NMR SpectrumNot AvailableSpectrum
1D NMR1H NMR SpectrumNot AvailableSpectrum
1D NMR13C NMR SpectrumNot AvailableSpectrum
2D NMR[1H,13C] 2D NMR SpectrumNot AvailableSpectrum
Toxicity Profile
Route of ExposureNot Available
Mechanism of ToxicityNot Available
MetabolismNot Available
Toxicity ValuesNot Available
Lethal DoseNot Available
Carcinogenicity (IARC Classification)Not Available
Uses/SourcesNot Available
Minimum Risk LevelNot Available
Health EffectsNot Available
SymptomsNot Available
TreatmentNot Available
Concentrations
Not Available
DrugBank IDDB06770
HMDB IDHMDB0003119
FooDB IDFDB008745
Phenol Explorer IDNot Available
KNApSAcK IDC00029811
BiGG IDNot Available
BioCyc IDBENZYL-ALCOHOL
METLIN IDNot Available
PDB IDNot Available
Wikipedia LinkBenzyl_Alcohol
Chemspider ID13860335
ChEBI ID17987
PubChem Compound ID244
Kegg Compound IDC03485
YMDB IDYMDB01426
ECMDB IDECMDB24002
References
Synthesis ReferenceNot Available
MSDSNot Available
General References
1. https://www.ncbi.nlm.nih.gov/pubmed/?term=11766131
2. https://www.ncbi.nlm.nih.gov/pubmed/?term=21557223
3. https://www.ncbi.nlm.nih.gov/pubmed/?term=22036973
4. Xu, 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.
5. Xu, 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.
6. Melikian AA, O'Connor R, Prahalad AK, Hu P, Li H, Kagan M, Thompson S: Determination of the urinary benzene metabolites S-phenylmercapturic acid and trans,trans-muconic acid by liquid chromatography-tandem mass spectrometry. Carcinogenesis. 1999 Apr;20(4):719-26.
7. Hulla JE, French JE, Dunnick JK: Chromosome 11 allelotypes reflect a mechanism of chemical carcinogenesis in heterozygous p53-deficient mice. Carcinogenesis. 2001 Jan;22(1):89-98.
8. Xiao G, Pan C, Cai Y, Lin H, Fu Z: Effect of benzene, toluene, xylene on the semen quality and the function of accessory gonad of exposed workers. Ind Health. 2001 Apr;39(2):206-10.
9. Nielsen CU, Andersen R, Brodin B, Frokjaer S, Taub ME, Steffansen B: Dipeptide model prodrugs for the intestinal oligopeptide transporter. Affinity for and transport via hPepT1 in the human intestinal Caco-2 cell line. J Control Release. 2001 Sep 11;76(1-2):129-38.
10. Salamon A, Hagenauer B, Thalhammer T, Szekeres T, Krohn K, Jayaram HN, Jager W: Metabolism and disposition of the novel antileukaemic drug, benzamide riboside, in the isolated perfused rat liver. Life Sci. 2001 Oct 12;69(21):2489-502.
11. Lu HF, Wu HC, Hsia TC, Chen WC, Hung CF, Chung JG: Effects of butylated hydroxyanisole and butylated hydroxytoluene on DNA adduct formation and arylamine N-acetyltransferase activity in human bladder tumour cells. J Appl Toxicol. 2002 Jan-Feb;22(1):37-44.
12. Sinclair GC, Wester RC, Maibach HI: Partition coefficients for benzene in human skin. AIHA J (Fairfax, Va). 2002 Nov-Dec;63(6):685-8.
13. Fukuda T, Ito H, Mukainaka T, Tokuda H, Nishino H, Yoshida T: Anti-tumor promoting effect of glycosides from Prunus persica seeds. Biol Pharm Bull. 2003 Feb;26(2):271-3.
14. Lan Q, Zhang L, Li G, Vermeulen R, Weinberg RS, Dosemeci M, Rappaport SM, Shen M, Alter BP, Wu Y, Kopp W, Waidyanatha S, Rabkin C, Guo W, Chanock S, Hayes RB, Linet M, Kim S, Yin S, Rothman N, Smith MT: Hematotoxicity in workers exposed to low levels of benzene. Science. 2004 Dec 3;306(5702):1774-6.
15. Gaskell M, McLuckie KI, Farmer PB: Comparison of the repair of DNA damage induced by the benzene metabolites hydroquinone and p-benzoquinone: a role for hydroquinone in benzene genotoxicity. Carcinogenesis. 2005 Mar;26(3):673-80. Epub 2004 Dec 23.
16. Hechler B, Magnenat S, Zighetti ML, Kassack MU, Ullmann H, Cazenave JP, Evans R, Cattaneo M, Gachet C: Inhibition of platelet functions and thrombosis through selective or nonselective inhibition of the platelet P2 receptors with increasing doses of NF449 [4,4',4'',4'''-(carbonylbis(imino-5,1,3-benzenetriylbis-(carbonylimino)))tetrakis -benzene-1,3-disulfonic acid octasodium salt]. J Pharmacol Exp Ther. 2005 Jul;314(1):232-43. Epub 2005 Mar 25.
17. Rana SV, Verma Y: Biochemical toxicity of benzene. J Environ Biol. 2005 Apr;26(2):157-68.
18. Weibel H, Nielsen LS, Larsen C, Bundgaard H: Macromolecular prodrugs. IXX. Kinetics of hydrolysis of benzyl dextran carbonate ester conjugates in aqueous buffer solutions and human plasma. Acta Pharm Nord. 1991;3(3):159-62.
19. Froebe CL, Simion FA, Rhein LD, Cagan RH, Kligman A: Stratum corneum lipid removal by surfactants: relation to in vivo irritation. Dermatologica. 1990;181(4):277-83.
20. Zhang HF, Davis WB, Chen XS, Jones KH, Whisler RL, Cornwell DG: Effects of oxidized low density lipoproteins on arachidonic acid metabolism in smooth muscle cells. J Lipid Res. 1990 Apr;31(4):551-65.
21. Nishikaze O, Iwata J: Direct determination of sulfate conjugates of 17-oxosteroids in urine by liquid chromatography. Clin Chem. 1986 May;32(5):835-9.
22. LeBel M, Ferron L, Masson M, Pichette J, Carrier C: Benzyl alcohol metabolism and elimination in neonates. Dev Pharmacol Ther. 1988;11(6):347-56.
23. De Leenheer AP, Bauwens RM: Radioimmunoassay for 1,25-dihydroxyvitamin D in serum or plasma. Clin Chem. 1985 Jan;31(1):142-6.
24. Dufer J: An improved cytochemical method for the evaluation of eosinophil colonies in soft-agar cultures from human blood or bone marrow. Acta Histochem. 1985;76(2):219-23.
25. Blank IH, McAuliffe DJ: Penetration of benzene through human skin. J Invest Dermatol. 1985 Dec;85(6):522-6.
26. Greenblatt DJ, Arendt RM, Locniskar A: Ibuprofen pharmacokinetics: use of liquid chromatography with radial compression separation. Arzneimittelforschung. 1983;33(12):1671-3.
27. Maibach HI, Anjo DM: Percutaneous penetration of benzene and benzene contained in solvents used in the rubber industry. Arch Environ Health. 1981 Sep-Oct;36(5):256-60.
28. Higo M, Kamata S: Inelastic electron tunneling spectroscopic study of biological compounds in human sweat adsorbed on alumina. Anal Chem. 1994 Mar 15;66(6):818-23.
29. Stolz A, Hammond L, Lou H, Takikawa H, Ronk M, Shively JE: cDNA cloning and expression of the human hepatic bile acid-binding protein. A member of the monomeric reductase gene family. J Biol Chem. 1993 May 15;268(14):10448-57.
30. Pierce CH, Dills RL, Silvey GW, Kalman DA: Partition coefficients between human blood or adipose tissue and air for aromatic solvents. Scand J Work Environ Health. 1996 Apr;22(2):112-8.
31. Cork A, Park KC: Identification of electrophysiologically-active compounds for the malaria mosquito, Anopheles gambiae, in human sweat extracts. Med Vet Entomol. 1996 Jul;10(3):269-76.
32. Farris GM, Robinson SN, Gaido KW, Wong BA, Wong VA, Leonard L, Shah R: Effects of low concentrations of benzene on mouse hematopoietic cells in vivo: a preliminary report. Environ Health Perspect. 1996 Dec;104 Suppl 6:1275-6.
33. Fredricks DN, Relman DA: Improved amplification of microbial DNA from blood cultures by removal of the PCR inhibitor sodium polyanetholesulfonate. J Clin Microbiol. 1998 Oct;36(10):2810-6.
34. 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.