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Record Information
Version4.0
StatusDetected and Quantified
Creation Date2006-08-13 16:50:24 UTC
Update Date2018-05-20 20:39:46 UTC
HMDB IDHMDB0004327
Secondary Accession Numbers
  • HMDB04327
Metabolite Identification
Common Name1-Butanol
Description1-Butanol, which is also known as n-butanol or 1-butanol or butyl alcohol (sometimes also called biobutanol when produced biologically), is an alcohol with a 4 carbon structure and the molecular formula of C4H10O. It is primarily used as a solvent, as an intermediate in chemical synthesis, and as a fuel. There are four isomeric structures for butanol. The straight chain isomer with the alcohol at an internal carbon is sec-butanol or 2-butanol. The branched isomer with the alcohol at a terminal carbon is isobutanol, and the branched isomer with the alcohol at the internal carbon is tert-butanol. 1-Butanol is produced in small amounts by gut microbial fermenetation through the butanoate metabolic pathway.
Structure
Thumb
Synonyms
ValueSource
1-Butyl alcoholChEBI
1-HydroxybutaneChEBI
BuOHChEBI
N-Butan-1-olChEBI
N-ButanolChEBI
N-Butyl alcoholChEBI
N-ButylalkoholChEBI
Propyl carbinolChEBI
ButanolHMDB
Butyl alcoholHMDB
Butyl hydroxideHMDB
HemostypHMDB
MethylolpropaneHMDB
PropylcarbinolHMDB
Alcohol, N-butylMeSH
N Butyl alcoholMeSH
Alcohol, butylMeSH
1 ButanolMeSH
N ButanolMeSH
Chemical FormulaC4H10O
Average Molecular Weight74.1216
Monoisotopic Molecular Weight74.073164942
IUPAC Namebutan-1-ol
Traditional Namebutanol
CAS Registry Number71-36-3
SMILES
CCCCO
InChI Identifier
InChI=1S/C4H10O/c1-2-3-4-5/h5H,2-4H2,1H3
InChI KeyLRHPLDYGYMQRHN-UHFFFAOYSA-N
Chemical Taxonomy
DescriptionThis compound belongs to the class of organic compounds known as primary alcohols. These are compounds comprising the primary alcohol functional group, with the general structure RCOH (R=alkyl, aryl).
KingdomOrganic compounds
Super ClassOrganic oxygen compounds
ClassOrganooxygen compounds
Sub ClassAlcohols and polyols
Direct ParentPrimary alcohols
Alternative Parents
Substituents
  • Hydrocarbon derivative
  • Primary alcohol
  • Aliphatic acyclic compound
Molecular FrameworkAliphatic acyclic compounds
External Descriptors
Ontology
Physiological effect

Organoleptic effect:

Health effect:

Disposition

Route of exposure:

Source:

Biological location:

Role

Industrial application:

Physical Properties
StateLiquid
Experimental Properties
PropertyValueReference
Melting Point-89.8 °CNot Available
Boiling PointNot AvailableNot Available
Water Solubility63.2 mg/mL at 25 °CNot Available
LogP0.88HANSCH,C ET AL. (1995)
Predicted Properties
PropertyValueSource
Water Solubility158 g/LALOGPS
logP0.84ALOGPS
logP0.81ChemAxon
logS0.33ALOGPS
pKa (Strongest Acidic)16.95ChemAxon
pKa (Strongest Basic)-1.9ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count1ChemAxon
Hydrogen Donor Count1ChemAxon
Polar Surface Area20.23 ŲChemAxon
Rotatable Bond Count2ChemAxon
Refractivity22.13 m³·mol⁻¹ChemAxon
Polarizability9.21 ųChemAxon
Number of Rings0ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Spectra
Spectra
Spectrum TypeDescriptionSplash Key
GC-MSGC-MS Spectrum - EI-B (Non-derivatized)splash10-052f-9000000000-f8337e5e053a4d17e4edView in MoNA
GC-MSGC-MS Spectrum - EI-B (Non-derivatized)splash10-052f-9000000000-610cf73e0b514e180dbdView in MoNA
GC-MSGC-MS Spectrum - EI-B (Non-derivatized)splash10-055f-9000000000-7e23cd40dde01cb89b6fView in MoNA
GC-MSGC-MS Spectrum - EI-B (Non-derivatized)splash10-052f-9000000000-f8337e5e053a4d17e4edView in MoNA
GC-MSGC-MS Spectrum - EI-B (Non-derivatized)splash10-052f-9000000000-610cf73e0b514e180dbdView in MoNA
GC-MSGC-MS Spectrum - EI-B (Non-derivatized)splash10-055f-9000000000-7e23cd40dde01cb89b6fView in MoNA
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-004l-9000000000-b70087d61cbf63d60bd5View in MoNA
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (1 TMS) - 70eV, Positivesplash10-00di-9200000000-08a8f57a90b00db3596aView in MoNA
LC-MS/MSLC-MS/MS Spectrum - EI-B (HITACHI RMU-6M) , Positivesplash10-052f-9000000000-69148177e3417cc669fdView in MoNA
LC-MS/MSLC-MS/MS Spectrum - EI-B (HITACHI RMU-7M) , Positivesplash10-052f-9000000000-7ebca2648ffd63942337View in MoNA
LC-MS/MSLC-MS/MS Spectrum - EI-B (HITACHI M-80B) , Positivesplash10-055f-9000000000-7e23cd40dde01cb89b6fView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0a6r-9000000000-53a465f38bad658bb673View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0a4i-9000000000-9145b21c5f3ae37774e0View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0a4l-9000000000-686e7cdc50d3fda3a0ffView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0a6r-9000000000-53a465f38bad658bb673View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0a4i-9000000000-9145b21c5f3ae37774e0View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0a4l-9000000000-686e7cdc50d3fda3a0ffView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-00di-9000000000-61d09b30d6a547d109fcView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-00di-9000000000-4d4d1c2159c658c4ee24View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-052f-9000000000-2119b542a1efb8432d12View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-00di-9000000000-61d09b30d6a547d109fcView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-00di-9000000000-4d4d1c2159c658c4ee24View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-052f-9000000000-2119b542a1efb8432d12View in MoNA
MSMass Spectrum (Electron Ionization)splash10-054o-9000000000-061591a78bc1cdeda799View in MoNA
1D NMR1H NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR1H NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR13C NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR1H NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR13C NMR SpectrumNot AvailableView in JSpectraViewer
2D NMR[1H,13C] 2D NMR SpectrumNot AvailableView in JSpectraViewer
Biological Properties
Cellular LocationsNot Available
Biospecimen Locations
  • Blood
  • Feces
  • Saliva
Tissue Locations
  • Epidermis
  • Fibroblasts
  • Kidney
  • Liver
  • Pancreas
  • Spleen
  • Stratum Corneum
Pathways
Normal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
BloodDetected and Quantified0.08 (0.00 - 0.27) uMAdult (>18 years old)BothNormal details
FecesDetected but not Quantified Adult (>18 years old)BothNormal details
FecesDetected but not Quantified Adult (>18 years old)Both
Normal
details
FecesDetected but not Quantified Adult (>18 years old)BothNormal details
FecesDetected but not Quantified Adult (>18 years old)BothNormal details
FecesDetected but not Quantified Adult (>18 years old)Both
Normal
details
FecesDetected and Quantified0-299732.692 nmol/g wet fecesChildren (1-13 years old)Not Specified
Normal
details
FecesDetected but not Quantified Newborn (0-30 days old)Both
Normal
details
FecesDetected but not Quantified Adult (>18 years old)Both
Normal
details
FecesDetected but not Quantified Adult (>18 years old)Both
Normal
details
SalivaDetected but not Quantified Adult (>18 years old)Not SpecifiedNormal details
Abnormal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
BloodDetected and Quantified0.11 (0 - 2.43) uMAdult (>18 years old)BothDiabetes details
FecesDetected but not Quantified Adult (>18 years old)BothImmunoglobulin A nephropathy (IgAN) non progressor details
FecesDetected but not Quantified Adult (>18 years old)BothImmunoglobulin A nephropathy (IgAN) progressor details
FecesDetected but not Quantified Adult (>18 years old)Both
Nonalcoholic fatty liver disease (NAFLD)
details
FecesDetected but not Quantified Adult (>18 years old)BothCrohns disease details
FecesDetected but not Quantified Adult (>18 years old)BothUlcerative colitis details
FecesDetected but not Quantified Adult (>18 years old)Both
Ulcerative colitis
details
FecesDetected but not Quantified Adult (>18 years old)Both
Crohn's disease
details
FecesDetected and Quantified0-591010.807 nmol/g wet fecesChildren (1-13 years old)Not Specified
Treated celiac disease
details
FecesDetected but not Quantified Not SpecifiedNot Specified
Crohn's disease
details
FecesDetected but not Quantified Not SpecifiedNot Specified
Ulcerative colitis
details
FecesDetected and Quantified0.00192 (0.00103-0.00548) nmol/g wet fecesNot SpecifiedNot Specified
Crohns disease
details
FecesDetected and Quantified0.000337 (0.000040-0.00747) nmol/g wet fecesNot SpecifiedNot Specified
Ulcerative colitis
details
FecesDetected and Quantified0.000769 (0.000283-0.00120) nmol/g wet fecesNot SpecifiedNot Specified
Irritable bowel syndrome
details
FecesDetected but not Quantified Adult (>18 years old)Both
Campylobacter jejuni infection
details
FecesDetected but not Quantified Adult (>18 years old)Both
Clostridium difficile infection
details
FecesDetected but not Quantified Adult (>18 years old)Both
Ulcerative Colitis
details
Associated Disorders and Diseases
Disease References
Celiac disease
  1. Di Cagno R, De Angelis M, De Pasquale I, Ndagijimana M, Vernocchi P, Ricciuti P, Gagliardi F, Laghi L, Crecchio C, Guerzoni ME, Gobbetti M, Francavilla R: Duodenal and faecal microbiota of celiac children: molecular, phenotype and metabolome characterization. BMC Microbiol. 2011 Oct 4;11:219. doi: 10.1186/1471-2180-11-219. [PubMed:21970810 ]
Crohn's disease
  1. Walton C, Fowler DP, Turner C, Jia W, Whitehead RN, Griffiths L, Dawson C, Waring RH, Ramsden DB, Cole JA, Cauchi M, Bessant C, Hunter JO: Analysis of volatile organic compounds of bacterial origin in chronic gastrointestinal diseases. Inflamm Bowel Dis. 2013 Sep;19(10):2069-78. doi: 10.1097/MIB.0b013e31829a91f6. [PubMed:23867873 ]
  2. De Preter V, Machiels K, Joossens M, Arijs I, Matthys C, Vermeire S, Rutgeerts P, Verbeke K: Faecal metabolite profiling identifies medium-chain fatty acids as discriminating compounds in IBD. Gut. 2015 Mar;64(3):447-58. doi: 10.1136/gutjnl-2013-306423. Epub 2014 May 8. [PubMed:24811995 ]
  3. Ahmed I, Greenwood R, Costello B, Ratcliffe N, Probert CS: Investigation of faecal volatile organic metabolites as novel diagnostic biomarkers in inflammatory bowel disease. Aliment Pharmacol Ther. 2016 Mar;43(5):596-611. doi: 10.1111/apt.13522. Epub 2016 Jan 25. [PubMed:26806034 ]
Diabetes mellitus type 2
  1. Liebich HM, Buelow HJ, Kallmayer R: Quantification of endogenous aliphatic alcohols in serum and urine. J Chromatogr. 1982 Apr 30;239:343-9. [PubMed:7096503 ]
Irritable bowel syndrome
  1. Walton C, Fowler DP, Turner C, Jia W, Whitehead RN, Griffiths L, Dawson C, Waring RH, Ramsden DB, Cole JA, Cauchi M, Bessant C, Hunter JO: Analysis of volatile organic compounds of bacterial origin in chronic gastrointestinal diseases. Inflamm Bowel Dis. 2013 Sep;19(10):2069-78. doi: 10.1097/MIB.0b013e31829a91f6. [PubMed:23867873 ]
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 ]
  2. Walton C, Fowler DP, Turner C, Jia W, Whitehead RN, Griffiths L, Dawson C, Waring RH, Ramsden DB, Cole JA, Cauchi M, Bessant C, Hunter JO: Analysis of volatile organic compounds of bacterial origin in chronic gastrointestinal diseases. Inflamm Bowel Dis. 2013 Sep;19(10):2069-78. doi: 10.1097/MIB.0b013e31829a91f6. [PubMed:23867873 ]
  3. De Preter V, Machiels K, Joossens M, Arijs I, Matthys C, Vermeire S, Rutgeerts P, Verbeke K: Faecal metabolite profiling identifies medium-chain fatty acids as discriminating compounds in IBD. Gut. 2015 Mar;64(3):447-58. doi: 10.1136/gutjnl-2013-306423. Epub 2014 May 8. [PubMed:24811995 ]
  4. Ahmed I, Greenwood R, Costello B, Ratcliffe N, Probert CS: Investigation of faecal volatile organic metabolites as novel diagnostic biomarkers in inflammatory bowel disease. Aliment Pharmacol Ther. 2016 Mar;43(5):596-611. doi: 10.1111/apt.13522. Epub 2016 Jan 25. [PubMed:26806034 ]
Nonalcoholic fatty liver disease
  1. Raman M, Ahmed I, Gillevet PM, Probert CS, Ratcliffe NM, Smith S, Greenwood R, Sikaroodi M, Lam V, Crotty P, Bailey J, Myers RP, Rioux KP: Fecal microbiome and volatile organic compound metabolome in obese humans with nonalcoholic fatty liver disease. Clin Gastroenterol Hepatol. 2013 Jul;11(7):868-75.e1-3. doi: 10.1016/j.cgh.2013.02.015. Epub 2013 Feb 27. [PubMed:23454028 ]
Associated OMIM IDs
DrugBank IDDB02145
Phenol Explorer Compound IDNot Available
FoodDB IDFDB012614
KNApSAcK IDC00035814
Chemspider ID258
KEGG Compound IDC06142
BioCyc IDBUTANOL
BiGG IDNot Available
Wikipedia LinkN-Butanol
METLIN ID7052
PubChem Compound263
PDB ID1BO
ChEBI ID28885
References
Synthesis ReferenceTsuchida, Takashi; Sakuma, Shuji. Ethanol to 1-butanol on hydroxyapatite. Shokubai (2007), 49(3), 238-243.
Material Safety Data Sheet (MSDS)Download (PDF)
General References
  1. Okamoto M, Kaji R, Kasetani H, Yoshida H, Moriya Y, Saito M, Sato M: Purification and characterization of interferon-gamma-inducing molecule of OK-432, a penicillin-killed streptococcal preparation, by monoclonal antibody neutralizing interferon-gamma-inducing activity of OK-432. J Immunother Emphasis Tumor Immunol. 1993 May 4;13(4):232-42. [PubMed:8334107 ]
  2. Copovi A, Diez-Sales O, Herraez-Dominguez JV, Herraez-Dominguez M: Enhancing effect of alpha-hydroxyacids on "in vitro" permeation across the human skin of compounds with different lipophilicity. Int J Pharm. 2006 May 11;314(1):31-6. Epub 2006 Mar 20. [PubMed:16545927 ]
  3. Bailyes EM, Seabrook RN, Calvin J, Maguire GA, Price CP, Siddle K, Luzio JP: The preparation of monoclonal antibodies to human bone and liver alkaline phosphatase and their use in immunoaffinity purification and in studying these enzymes when present in serum. Biochem J. 1987 Jun 15;244(3):725-33. [PubMed:2451502 ]
  4. Gainer AL, Stinson RA: Evidence that alkaline phosphatase from human neutrophils is the same gene product as the liver/kidney/bone isoenzyme. Clin Chim Acta. 1982 Aug 4;123(1-2):11-7. [PubMed:7116633 ]
  5. Yamamoto K, Takahashi Y, Mano T, Sakata Y, Nishikawa N, Yoshida J, Oishi Y, Hori M, Miwa T, Inoue S, Masuyama T: N-methylethanolamine attenuates cardiac fibrosis and improves diastolic function: inhibition of phospholipase D as a possible mechanism. Eur Heart J. 2004 Jul;25(14):1221-9. [PubMed:15246640 ]
  6. Seiffert UB, Siede WH, Welsch GJ, Oremek G: Multiple forms of alkaline phosphatases in human liver tissue. Clin Chim Acta. 1984 Dec 15;144(1):17-27. [PubMed:6210164 ]
  7. Chen M: Amended final report of the safety assessment of t-Butyl Alcohol as used in cosmetics. Int J Toxicol. 2005;24 Suppl 2:1-20. [PubMed:16154913 ]
  8. Chang CH, Angellis D: Identification of a butanol-extractable human placenta-specific antigen with alkaline phosphatase activity. J Immunol. 1976 Jul;117(1):91-6. [PubMed:58937 ]
  9. Oakley DM, Swarbrick J: Effects of ionization on the percutaneous absorption of drugs: partitioning of nicotine into organic liquids and hydrated stratum corneum. J Pharm Sci. 1987 Dec;76(12):866-71. [PubMed:3440928 ]
  10. Waddell WJ, Marlowe C: Inhibition by alcohols of the localization of radioactive nitrosonornicotine in sites of tumor formation. Science. 1983 Jul 1;221(4605):51-3. [PubMed:6857261 ]
  11. Bieler CA, Cornelius MG, Klein R, Arlt VM, Wiessler M, Phillips DH, Schmeiser HH: DNA adduct formation by the environmental contaminant 3-nitrobenzanthrone after intratracheal instillation in rats. Int J Cancer. 2005 Oct 10;116(6):833-8. [PubMed:15856450 ]
  12. Wulkan RW, Huijskes-Heins MI, Leijnse B: Hydrophobic properties of alkaline phosphatases. Int J Biochem. 1986;18(11):1045-51. [PubMed:3803695 ]
  13. Kalimanovska V, Whitaker KB, Moss DW: Effect of bromelain on alkaline phosphatases of intestinal and non-intestinal tissues and serum. Clin Chim Acta. 1987 Dec;170(2-3):219-25. [PubMed:3436056 ]
  14. Basu A, Glew RH: Characterization of the activation of rat liver beta-glucosidase by sialosylgangliotetraosylceramide. J Biol Chem. 1985 Oct 25;260(24):13067-73. [PubMed:3932339 ]
  15. Arlt VM, Sorg BL, Osborne M, Hewer A, Seidel A, Schmeiser HH, Phillips DH: DNA adduct formation by the ubiquitous environmental pollutant 3-nitrobenzanthrone and its metabolites in rats. Biochem Biophys Res Commun. 2003 Jan 3;300(1):107-14. [PubMed:12480528 ]

Only showing the first 10 proteins. There are 34 proteins in total.

Enzymes

General function:
Involved in arylesterase activity
Specific function:
Has low activity towards the organophosphate paraxon and aromatic carboxylic acid esters. Rapidly hydrolyzes lactones such as statin prodrugs (e.g. lovastatin). Hydrolyzes aromatic lactones and 5- or 6-member ring lactones with aliphatic substituents but not simple lactones or those with polar substituents.
Gene Name:
PON3
Uniprot ID:
Q15166
Molecular weight:
39607.185
General function:
Involved in arylesterase activity
Specific function:
Hydrolyzes the toxic metabolites of a variety of organophosphorus insecticides. Capable of hydrolyzing a broad spectrum of organophosphate substrates and lactones, and a number of aromatic carboxylic acid esters. Mediates an enzymatic protection of low density lipoproteins against oxidative modification and the consequent series of events leading to atheroma formation.
Gene Name:
PON1
Uniprot ID:
P27169
Molecular weight:
39730.99
General function:
Involved in arylesterase activity
Specific function:
Capable of hydrolyzing lactones and a number of aromatic carboxylic acid esters. Has antioxidant activity. Is not associated with high density lipoprotein. Prevents LDL lipid peroxidation, reverses the oxidation of mildly oxidized LDL, and inhibits the ability of MM-LDL to induce monocyte chemotaxis.
Gene Name:
PON2
Uniprot ID:
Q15165
Molecular weight:
39380.535
General function:
Involved in catalytic activity
Specific function:
Not Available
Gene Name:
ALPI
Uniprot ID:
P09923
Molecular weight:
56811.695
General function:
Involved in acid phosphatase activity
Specific function:
Not Available
Gene Name:
ACP2
Uniprot ID:
P11117
Molecular weight:
48343.92
General function:
Involved in catalytic activity
Specific function:
This isozyme may play a role in skeletal mineralization.
Gene Name:
ALPL
Uniprot ID:
P05186
Molecular weight:
57304.435
General function:
Involved in hydrolase activity
Specific function:
Involved in osteopontin/bone sialoprotein dephosphorylation. Its expression seems to increase in certain pathological states such as Gaucher and Hodgkin diseases, the hairy cell, the B-cell, and the T-cell leukemias.
Gene Name:
ACP5
Uniprot ID:
P13686
Molecular weight:
36598.47
General function:
Involved in catalytic activity
Specific function:
Not Available
Gene Name:
ALPPL2
Uniprot ID:
P10696
Molecular weight:
57376.515
General function:
Involved in oxidoreductase activity
Specific function:
ALDHs play a major role in the detoxification of alcohol-derived acetaldehyde. They are involved in the metabolism of corticosteroids, biogenic amines, neurotransmitters, and lipid peroxidation.
Gene Name:
ALDH1B1
Uniprot ID:
P30837
Molecular weight:
57248.96
General function:
Involved in sulfotransferase activity
Specific function:
Sulfotransferase that utilizes 3'-phospho-5'-adenylyl sulfate (PAPS) as sulfonate donor to catalyze the sulfate conjugation of many hormones, neurotransmitters, drugs and xenobiotic compounds. Sulfonation increases the water solubility of most compounds, and therefore their renal excretion, but it can also result in bioactivation to form active metabolites. Sulfates hydroxysteroids like DHEA. Isoform 1 preferentially sulfonates cholesterol, and isoform 2 avidly sulfonates pregnenolone but not cholesterol.
Gene Name:
SULT2B1
Uniprot ID:
O00204
Molecular weight:
39598.595

Only showing the first 10 proteins. There are 34 proteins in total.