Record Information
Version3.6
Creation Date2007-04-12 20:13:40 UTC
Update Date2013-05-29 19:42:33 UTC
HMDB IDHMDB06006
Secondary Accession NumbersNone
Metabolite Identification
Common NameIsobutanol
DescriptionIsobutanol is an aliphatic alcohol. Isobutanol is a colorless, flammable, organic compound with a characteristic smell. Isobutanol is widely used in industry, as a solvent in chemical reactions, as well as being a useful starting material for organic synthesis. Isobutanol is a flammable liquid that should be stored and used in well-ventilated areas. It is moderately irritating to the skin and greatly irritating to the eyes, mucous membranes and respiratory tract. Exposure to high concentrations of its vapour can cause temporary narcosis. Isobutanol is occasionally found as a volatile component of urine and arises from gut microbial metabolism. Isobutanol is used as one of the markers to measure occupational exposure to a mixture of solvents. Aliphatic alcohols levels increase in both diabetes mellitus and insulin-dependent diabetes patients. (PMID: 5556886 , 2477620 , 9143482 , 7627316 , 2288731 ).
Structure
Thumb
Synonyms
  1. 1-Hydroxymethylpropane
  2. 2-Methyl propanol
  3. 2-Methyl-1-propanol
  4. 2-Methyl-1-propanyl alcohol
  5. 2-Methylpropan-1-ol
  6. 2-MethylpropanoI
  7. 2-Methylpropanol
  8. 2-Methylpropanol-1
  9. 2-Methylpropyl alcohol
  10. Alcool isobutylique
  11. I-Butanol
  12. I-Butyl alcohol
  13. IBA
  14. Iso-butyl alcohol
  15. Isobutanol
  16. Isobutyl alcohol
  17. Isopropyl carbitol
  18. Isopropylcarbinol
  19. Methyl-2 propanol-1
Chemical FormulaC4H10O
Average Molecular Weight74.1216
Monoisotopic Molecular Weight74.073164942
IUPAC Name2-methylpropan-1-ol
Traditional IUPAC Nameisobutanol
CAS Registry Number78-83-1
SMILES
CC(C)CO
InChI Identifier
InChI=1S/C4H10O/c1-4(2)3-5/h4-5H,3H2,1-2H3
InChI KeyZXEKIIBDNHEJCQ-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 small molecule(Cyc)
  • alkyl alcohol(ChEBI)
  • primary alcohol(ChEBI)
Substituents
  • N/A
Direct ParentPrimary Alcohols
Ontology
StatusExpected and Not Quantified
Origin
  • Endogenous
  • Microbial
BiofunctionNot Available
ApplicationNot Available
Cellular locationsNot Available
Physical Properties
StateLiquid
Experimental Properties
PropertyValueReference
Melting Point-108 °CNot Available
Boiling PointNot AvailableNot Available
Water Solubility85 mg/mL at 25 °CNot Available
LogP0.76HANSCH,C ET AL. (1995)
Predicted Properties
PropertyValueSource
water solubility140 g/LALOGPS
logP0.6ALOGPS
logP0.73ChemAxon
logS0.28ALOGPS
pKa (strongest acidic)17.33ChemAxon
pKa (strongest basic)-1.8ChemAxon
physiological charge0ChemAxon
hydrogen acceptor count1ChemAxon
hydrogen donor count1ChemAxon
polar surface area20.23ChemAxon
rotatable bond count1ChemAxon
refractivity22.01ChemAxon
polarizability9.07ChemAxon
Spectra
SpectraNot Available
Biological Properties
Cellular LocationsNot Available
Biofluid LocationsNot Available
Tissue LocationNot Available
PathwaysNot Available
Normal Concentrations
Not Available
Abnormal Concentrations
Not Available
Associated Disorders and Diseases
Disease ReferencesNone
Associated OMIM IDsNone
DrugBank IDNot Available
DrugBank Metabolite IDNot Available
Phenol Explorer Compound IDNot Available
Phenol Explorer Metabolite IDNot Available
FoodDB IDFDB003274
KNApSAcK IDNot Available
Chemspider ID6312
KEGG Compound IDC14710
BioCyc IDISOBUTANOL
BiGG IDNot Available
Wikipedia Linkhttp://en.wikipedia.org/wiki/Isobutanol
NuGOwiki LinkHMDB06006
Metagene LinkHMDB06006
METLIN IDNot Available
PubChem Compound6560
PDB IDNot Available
ChEBI ID46645
References
Synthesis ReferenceNot Available
Material Safety Data Sheet (MSDS)Not Available
General References
  1. Zlatkis A, Liebich HM: Profile of volatile metabolites in human urine. Clin Chem. 1971 Jul;17(7):592-4. Pubmed: 5556886
  2. Bilzer N, Schmutte P, Jehs M, Penners BM: [Kinetics of aliphatic alcohols (methanol, propanol-1 and isobutanol) in the presence of alcohol in the human body]. Blutalkohol. 1990 Nov;27(6):385-409. Pubmed: 2288731
  3. Inglik N, Rudenko BA, Kakhnovskii IM, Koroleva TV: [Gas chromatographic study of the composition of the volatile components of the urine in normal subjects and patients with diabetes mellitus]. Lab Delo. 1989;(8):24-7. Pubmed: 2477620
  4. Norback D, Bjornsson E, Janson C, Widstrom J, Boman G: Asthmatic symptoms and volatile organic compounds, formaldehyde, and carbon dioxide in dwellings. Occup Environ Med. 1995 Jun;52(6):388-95. Pubmed: 7627316
  5. Kruszewski FH, Walker TL, DiPasquale LC: Evaluation of a human corneal epithelial cell line as an in vitro model for assessing ocular irritation. Fundam Appl Toxicol. 1997 Apr;36(2):130-40. Pubmed: 9143482

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:
FAR2
Uniprot ID:
Q96K12
Gene Name:
AWAT2
Uniprot ID:
Q6E213
26. 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