Record Information
Version3.6
Creation Date2006-08-13 16:50:24 UTC
Update Date2013-02-09 00:13:11 UTC
HMDB IDHMDB04327
Secondary Accession NumbersNone
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
  1. 1-Butanol
  2. 1-Butyl alcohol
  3. Butanol
  4. Butyl alcohol
  5. Butyl hydroxide
  6. Hemostyp
  7. Methylolpropane
  8. N-Butanol
  9. N-Butyl alcohol
  10. Propylcarbinol
Chemical FormulaC4H10O
Average Molecular Weight74.1216
Monoisotopic Molecular Weight74.073164942
IUPAC Namebutan-1-ol
Traditional IUPAC Namebutan-1-ol
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
KingdomOrganic Compounds
Super ClassAliphatic Acyclic Compounds
ClassAlcohols and Polyols
Sub ClassPrimary Alcohols
Other Descriptors
  • Aliphatic Acyclic Compounds
  • Fatty alcohols(Lipidmaps)
  • a primary alcohol(Cyc)
  • alkyl alcohol(ChEBI)
  • primary alcohol(ChEBI)
Substituents
  • N/A
Direct ParentPrimary Alcohols
Ontology
StatusDetected and Quantified
Origin
  • Endogenous
  • Microbial
BiofunctionNot Available
ApplicationNot Available
Cellular locationsNot Available
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 area20.23ChemAxon
rotatable bond count2ChemAxon
refractivity22.13ChemAxon
polarizability9.21ChemAxon
Spectra
Spectra
Biological Properties
Cellular LocationsNot Available
Biofluid Locations
  • Blood
Tissue Location
  • Epidermis
  • Fibroblasts
  • Kidney
  • Liver
  • Pancreas
  • Spleen
  • Stratum Corneum
PathwaysNot Available
Normal Concentrations
BiofluidStatusValueAgeSexConditionReference
BloodDetected and Quantified0.08 (0.00 - 0.27) uMAdult (>18 years old)BothNormal
Abnormal Concentrations
BiofluidStatusValueAgeSexConditionReference
BloodDetected and Quantified0.11 (0 - 2.43) uMAdult (>18 years old)BothDiabetes
Associated Disorders and Diseases
Disease References
Diabetes mellitus type 2
  • 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
Associated OMIM IDs
DrugBank IDDB02145
DrugBank Metabolite IDNot Available
Phenol Explorer Compound IDNot Available
Phenol Explorer Metabolite IDNot Available
FoodDB IDFDB012614
KNApSAcK IDC00035814
Chemspider ID258
KEGG Compound IDC06142
BioCyc IDBUTANOL
BiGG IDNot Available
Wikipedia Link1-Butanol
NuGOwiki LinkHMDB04327
Metagene LinkHMDB04327
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)Not Available
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. 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

Enzymes

Gene Name:
PON3
Uniprot ID:
Q15166
Gene Name:
PON1
Uniprot ID:
P27169
Gene Name:
PON2
Uniprot ID:
Q15165
Gene Name:
ACP2
Uniprot ID:
P11117
Gene Name:
ALPPL2
Uniprot ID:
P10696
Gene Name:
ALDH1B1
Uniprot ID:
P30837
Gene Name:
SORD
Uniprot ID:
Q00796
Gene Name:
AKR1A1
Uniprot ID:
P14550
Gene Name:
ADH4
Uniprot ID:
P08319
Gene Name:
ADH1B
Uniprot ID:
P00325
Gene Name:
ADH1A
Uniprot ID:
P07327
Gene Name:
ADH6
Uniprot ID:
P28332
Gene Name:
GUSB
Uniprot ID:
P08236
Gene Name:
FUCA2
Uniprot ID:
Q9BTY2
Gene Name:
LRAT
Uniprot ID:
O95237
Gene Name:
RDH13
Uniprot ID:
Q8NBN7
Gene Name:
FAR2
Uniprot ID:
Q96K12
Gene Name:
AWAT2
Uniprot ID:
Q6E213
27. Klotho
Gene Name:
KL
Uniprot ID:
Q9UEF7
Gene Name:
ACPT
Uniprot ID:
Q9BZG2
Gene Name:
CES5A
Uniprot ID:
Q6NT32
Gene Name:
ACPL2
Uniprot ID:
Q8TE99
Gene Name:
TP53I3
Uniprot ID:
Q53FA7