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Record Information
Version5.0
StatusDetected and Quantified
Creation Date2006-05-22 15:12:34 UTC
Update Date2021-10-13 04:40:43 UTC
HMDB IDHMDB0003119
Secondary Accession Numbers
  • HMDB03119
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
Data?1601247463
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 Weight108.1378
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 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
Disposition

Biological location

Source

Route of exposure

Physical Properties
StateLiquid
Experimental Molecular Properties
PropertyValueReference
Melting Point-15.2 °CNot Available
Boiling Point205.00 to 206.00 °C. @ 760.00 mm HgThe Good Scents Company Information System
Water Solubility42.9 mg/mL at 25 °CNot Available
LogP1.10HANSCH,C ET AL. (1995)
Experimental Spectral PropertiesNot Available
Predicted Molecular Properties
PropertyValueSource
Water Solubility26.8 g/LALOGPS
logP10(1.07) g/LALOGPS
logP10(1.21) g/LChemAxon
logS10(-0.61) g/LALOGPS
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
Predicted Spectral Properties

Predicted Collision Cross Sections

PredictorAdduct TypeCCS Value (Å2)Reference
DarkChem[M+H]+121.17731661259
DarkChem[M-H]-117.51731661259

Predicted Kovats Retention Indices

Derivatized

Derivative Name / StructureSMILESKovats RI ValueColumn TypeReference
Benzyl alcohol,1TMS,#1C[Si](C)(C)OCC1=CC=CC=C11158.3Semi standard non polarhttps://arxiv.org/abs/1905.12712
Benzyl alcohol,1TBDMS,#1CC(C)(C)[Si](C)(C)OCC1=CC=CC=C11389.4Semi standard non polarhttps://arxiv.org/abs/1905.12712
Spectra

GC-MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Experimental GC-MSGC-MS Spectrum - Benzyl alcohol GC-MS (1 TMS)splash10-00ko-6900000000-a9d668ecd37a1579a6fe2014-06-16HMDB team, MONA, MassBankView Spectrum
Experimental GC-MSGC-MS Spectrum - Benzyl alcohol EI-B (Non-derivatized)splash10-056r-9400000000-77cec715500da9c57a842017-09-12HMDB team, MONA, MassBankView Spectrum
Experimental GC-MSGC-MS Spectrum - Benzyl alcohol EI-B (Non-derivatized)splash10-056r-9400000000-8dc38068387df3fa06aa2017-09-12HMDB team, MONA, MassBankView Spectrum
Experimental GC-MSGC-MS Spectrum - Benzyl alcohol EI-B (Non-derivatized)splash10-056r-9300000000-fb124b56257906cce9f12017-09-12HMDB team, MONA, MassBankView Spectrum
Experimental GC-MSGC-MS Spectrum - Benzyl alcohol EI-B (Non-derivatized)splash10-056r-9400000000-7a77e67486ae3b2dd8552017-09-12HMDB team, MONA, MassBankView Spectrum
Experimental GC-MSGC-MS Spectrum - Benzyl alcohol EI-B (Non-derivatized)splash10-056r-9400000000-dd0878988e7c2d9a54312017-09-12HMDB team, MONA, MassBankView Spectrum
Experimental GC-MSGC-MS Spectrum - Benzyl alcohol GC-MS (Non-derivatized)splash10-00ko-6900000000-a9d668ecd37a1579a6fe2017-09-12HMDB team, MONA, MassBankView Spectrum
Experimental GC-MSGC-MS Spectrum - Benzyl alcohol GC-EI-TOF (Non-derivatized)splash10-0006-8900000000-c256b0b7a0755f08ac642017-09-12HMDB team, MONA, MassBankView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Benzyl alcohol GC-MS (Non-derivatized) - 70eV, Positivesplash10-054o-9200000000-a9f7c0f39c81d478c0d42016-09-22Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Benzyl alcohol GC-MS (1 TMS) - 70eV, Positivesplash10-00dl-9300000000-e1cfa5e819f61adf9df22017-10-06Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Benzyl alcohol GC-MS (Non-derivatized) - 70eV, PositiveNot Available2021-10-12Wishart LabView Spectrum
MSMass Spectrum (Electron Ionization)splash10-056r-9400000000-a8f1fd78fa3f8781f2962015-03-01Not AvailableView Spectrum

MS/MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Experimental LC-MS/MSLC-MS/MS Spectrum - Benzyl alcohol Quattro_QQQ 10V, N/A-QTOF (Annotated)splash10-0a4i-9500000000-2a82c3dd7c6871f61c342012-07-25HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Benzyl alcohol Quattro_QQQ 25V, N/A-QTOF (Annotated)splash10-0006-9000000000-ad1762d5292c30b29bbd2012-07-25HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Benzyl alcohol Quattro_QQQ 40V, N/A-QTOF (Annotated)splash10-0006-9000000000-3c8d4c630cf42e3bfd3f2012-07-25HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Benzyl alcohol EI-B (HITACHI RMU-7M) , Positive-QTOFsplash10-056r-9400000000-c4dcb2148958f946cd012012-08-31HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Benzyl alcohol EI-B (HITACHI RMU-6M) , Positive-QTOFsplash10-056r-9400000000-e17e577dbe4546313a912012-08-31HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Benzyl alcohol EI-B (JEOL JMS-01-SG-2) , Positive-QTOFsplash10-056r-9300000000-fb124b56257906cce9f12012-08-31HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Benzyl alcohol EI-B (HITACHI M-80) , Positive-QTOFsplash10-056r-9400000000-47b3605316c57e02b84f2012-08-31HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Benzyl alcohol EI-B (HITACHI M-80B) , Positive-QTOFsplash10-056r-9400000000-dd0878988e7c2d9a54312012-08-31HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Benzyl alcohol , positive-QTOFsplash10-0a4i-3900000000-4d1bf15f6cf8f65bf0a62017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Benzyl alcohol 35V, Negative-QTOFsplash10-0a4i-1900000000-866ce230a3fc1ead83532021-09-20HMDB team, MONAView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Benzyl alcohol 10V, Positive-QTOFsplash10-0a4i-0900000000-3a71c23796a048eb999c2015-05-27Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Benzyl alcohol 20V, Positive-QTOFsplash10-0a4i-1900000000-40737e7bdf548d7142492015-05-27Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Benzyl alcohol 40V, Positive-QTOFsplash10-0uxr-9100000000-23e82914cfa9372ecafc2015-05-27Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Benzyl alcohol 10V, Negative-QTOFsplash10-0a4i-1900000000-17f95f5a398b5850abb22015-05-27Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Benzyl alcohol 20V, Negative-QTOFsplash10-0a6r-7900000000-733d283e0916e755a7362015-05-27Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Benzyl alcohol 40V, Negative-QTOFsplash10-004i-9000000000-d0c6e5fc39516ee594b42015-05-27Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Benzyl alcohol 10V, Positive-QTOFsplash10-0006-9000000000-d0618c117a092a2f72412021-09-23Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Benzyl alcohol 20V, Positive-QTOFsplash10-0006-9000000000-b65b57d5b2389beaf5f22021-09-23Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Benzyl alcohol 40V, Positive-QTOFsplash10-00kf-9000000000-a2b78129c0731eee69f42021-09-23Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Benzyl alcohol 10V, Negative-QTOFsplash10-004i-9200000000-72dc044d901c3dfcec512021-09-24Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Benzyl alcohol 20V, Negative-QTOFsplash10-004i-9000000000-fc58e0949de9ca4842ff2021-09-24Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Benzyl alcohol 40V, Negative-QTOFsplash10-004i-9000000000-fc58e0949de9ca4842ff2021-09-24Wishart LabView Spectrum

NMR Spectra

Spectrum TypeDescriptionDeposition DateSourceView
Predicted 1D NMR1H NMR Spectrum (1D, 100 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 100 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 1000 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 1000 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 200 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 200 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 300 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 300 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 400 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 400 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 500 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 500 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 600 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 600 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 700 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 700 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 800 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 800 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 900 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 900 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Experimental 2D NMR[1H, 13C]-HSQC NMR Spectrum (2D, 600 MHz, H2O, experimental)2012-12-05Wishart LabView Spectrum
Biological Properties
Cellular LocationsNot Available
Biospecimen Locations
  • Blood
  • Breath
  • Feces
  • Saliva
Tissue LocationsNot Available
Pathways
Normal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
FecesDetected but not QuantifiedNot QuantifiedAdult (>18 years old)Both
Normal
details
SalivaDetected but not QuantifiedNot QuantifiedAdult (>18 years old)Not SpecifiedNormal details
Abnormal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
BloodDetected and Quantified250 +/- 469.444 uMAdult (>18 years old)Both
Uremia
details
BreathDetected but not QuantifiedNot QuantifiedAdult (>18 years old)BothAsthma details
FecesDetected but not QuantifiedNot QuantifiedAdult (>18 years old)Both
Campylobacter jejuni infection
details
FecesDetected but not QuantifiedNot QuantifiedAdult (>18 years old)Both
Clostridium difficile infection
details
FecesDetected but not QuantifiedNot QuantifiedAdult (>18 years old)Both
Ulcerative Colitis
details
Associated Disorders and Diseases
Disease References
Uremia
  1. Vanholder R, De Smet R, Glorieux G, Argiles A, Baurmeister U, Brunet P, Clark W, Cohen G, De Deyn PP, Deppisch R, Descamps-Latscha B, Henle T, Jorres A, Lemke HD, Massy ZA, Passlick-Deetjen J, Rodriguez M, Stegmayr B, Stenvinkel P, Tetta C, Wanner C, Zidek W: Review on uremic toxins: classification, concentration, and interindividual variability. Kidney Int. 2003 May;63(5):1934-43. doi: 10.1046/j.1523-1755.2003.00924.x. [PubMed:12675874 ]
Asthma
  1. Ibrahim B, Basanta M, Cadden P, Singh D, Douce D, Woodcock A, Fowler SJ: Non-invasive phenotyping using exhaled volatile organic compounds in asthma. Thorax. 2011 Sep;66(9):804-9. doi: 10.1136/thx.2010.156695. Epub 2011 Jul 11. [PubMed:21749985 ]
Ulcerative colitis
  1. Garner CE, Smith S, de Lacy Costello B, White P, Spencer R, Probert CS, Ratcliffe NM: Volatile organic compounds from feces and their potential for diagnosis of gastrointestinal disease. FASEB J. 2007 Jun;21(8):1675-88. Epub 2007 Feb 21. [PubMed:17314143 ]
Associated OMIM IDs
DrugBank IDDB06770
Phenol Explorer Compound IDNot Available
FooDB 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
Food Biomarker OntologyNot Available
VMH IDNot Available
MarkerDB IDNot Available
Good Scents IDrw1001651
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
  1. 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. [PubMed:8486699 ]
  2. 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. [PubMed:12576693 ]
  3. 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. [PubMed:11341554 ]
  4. 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. [PubMed:8887339 ]
  5. 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. [PubMed:3229281 ]
  6. 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. [PubMed:15618234 ]
  7. 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. [PubMed:10223205 ]
  8. 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. [PubMed:11159746 ]
  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. [PubMed:11532319 ]
  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. [PubMed:11693257 ]
  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. [PubMed:11807928 ]
  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. [PubMed:12570074 ]
  13. 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. [PubMed:15576619 ]
  14. 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. [PubMed:15792995 ]
  15. Rana SV, Verma Y: Biochemical toxicity of benzene. J Environ Biol. 2005 Apr;26(2):157-68. [PubMed:16161967 ]
  16. 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. [PubMed:1724373 ]
  17. 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. [PubMed:1963606 ]
  18. 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. [PubMed:2351866 ]
  19. 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. [PubMed:2938850 ]
  20. De Leenheer AP, Bauwens RM: Radioimmunoassay for 1,25-dihydroxyvitamin D in serum or plasma. Clin Chem. 1985 Jan;31(1):142-6. [PubMed:3838086 ]
  21. 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. [PubMed:3929548 ]
  22. Blank IH, McAuliffe DJ: Penetration of benzene through human skin. J Invest Dermatol. 1985 Dec;85(6):522-6. [PubMed:4067326 ]
  23. Greenblatt DJ, Arendt RM, Locniskar A: Ibuprofen pharmacokinetics: use of liquid chromatography with radial compression separation. Arzneimittelforschung. 1983;33(12):1671-3. [PubMed:6686771 ]
  24. 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. [PubMed:7294890 ]
  25. 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. [PubMed:8179207 ]
  26. 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. [PubMed:8738889 ]
  27. 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. [PubMed:9118905 ]
  28. 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. [PubMed:9738025 ]
  29. 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. [PubMed:11766131 ]