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Record Information
Version4.0
StatusDetected but not Quantified
Creation Date2007-04-12 20:13:40 UTC
Update Date2019-07-23 05:47:06 UTC
HMDB IDHMDB0006006
Secondary Accession Numbers
  • HMDB06006
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 ). Isobutanol is a microbial metabolite found in Clostridium, Cupriavidus, Escherichia, Geobacillus, Saccharomyces and Synechococcus (PMID: 19946322 ).
Structure
Data?1563860826
Synonyms
ValueSource
1-HydroxymethylpropaneChEBI
2-Methyl-1-propanolChEBI
2-MethylpropanolChEBI
I-butanolChEBI
I-butyl alcoholChEBI
IBAChEBI
iso-Butyl alcoholChEBI
iso-C4H9OHChEBI
Isobutyl alcoholChEBI
IsobutylalkoholChEBI
IsopropylcarbinolChEBI
2-Methyl propanolHMDB
2-Methyl-1-propanyl alcoholHMDB
2-Methylpropan-1-olHMDB
2-MethylpropanoIHMDB
2-Methylpropanol-1HMDB
2-Methylpropyl alcoholHMDB
Alcool isobutyliqueHMDB
Isopropyl carbitolHMDB
Methyl-2 propanol-1HMDB
Isobutyl alcohol, aluminum saltMeSH
Isobutyl alcohol, sodium saltMeSH
Isobutyl alcohol, titanium (+4) saltMeSH
Chemical FormulaC4H10O
Average Molecular Weight74.1216
Monoisotopic Molecular Weight74.073164942
IUPAC Name2-methylpropan-1-ol
Traditional 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
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:

Disposition

Route of exposure:

Biological location:

Source:

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 Area20.23 ŲChemAxon
Rotatable Bond Count1ChemAxon
Refractivity22.01 m³·mol⁻¹ChemAxon
Polarizability9.07 ųChemAxon
Number of Rings0ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Spectra
Spectrum TypeDescriptionSplash KeyView
GC-MSGC-MS Spectrum - EI-B (Non-derivatized)splash10-0006-9000000000-7f721031d45407da0ffaJSpectraViewer | MoNA
GC-MSGC-MS Spectrum - EI-B (Non-derivatized)splash10-0006-9000000000-8f50f8925987fafa9f6eJSpectraViewer | MoNA
GC-MSGC-MS Spectrum - EI-B (Non-derivatized)splash10-0006-9000000000-a022508915e78517db51JSpectraViewer | MoNA
GC-MSGC-MS Spectrum - EI-B (Non-derivatized)splash10-0006-9000000000-7f721031d45407da0ffaJSpectraViewer | MoNA
GC-MSGC-MS Spectrum - EI-B (Non-derivatized)splash10-0006-9000000000-8f50f8925987fafa9f6eJSpectraViewer | MoNA
GC-MSGC-MS Spectrum - EI-B (Non-derivatized)splash10-0006-9000000000-a022508915e78517db51JSpectraViewer | MoNA
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-0006-9000000000-c81d9b093b562948ccc2JSpectraViewer | MoNA
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (1 TMS) - 70eV, Positivesplash10-0fnl-9300000000-9cc13c092f82e7caebedJSpectraViewer | MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-056r-9000000000-51f6abf0e4afb219bd9dJSpectraViewer | MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0a4i-9000000000-5c3b0b379d64147f0e14JSpectraViewer | MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0a4i-9000000000-aed2ffb2e0c694af93eaJSpectraViewer | MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-00di-9000000000-4648efd7a78339de7e6cJSpectraViewer | MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-00di-9000000000-5d4c9a7c73ad8673a5e5JSpectraViewer | MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0ab9-9000000000-c25bee7b5f5bbb13555bJSpectraViewer | MoNA
MSMass Spectrum (Electron Ionization)splash10-0006-9000000000-df76ec6cf6a8bfca3cf4JSpectraViewer | MoNA
1D NMR1H NMR SpectrumNot AvailableJSpectraViewer
1D NMR13C NMR SpectrumNot AvailableJSpectraViewer
Biological Properties
Cellular LocationsNot Available
Biospecimen Locations
  • Feces
  • Saliva
Tissue LocationsNot Available
Pathways
Normal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
FecesDetected but not Quantified Adult (>18 years old)Both
Normal
details
FecesDetected but not Quantified Adult (>18 years old)Not Specified
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
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
FecesDetected but not Quantified Adult (>18 years old)Both
Nonalcoholic fatty liver disease (NAFLD)
details
FecesDetected but not Quantified Adult (>18 years old)Both
Ulcerative colitis 
details
Associated Disorders and Diseases
Disease References
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. Ahmed I, Greenwood R, Costello Bde L, Ratcliffe NM, Probert CS: An investigation of fecal volatile organic metabolites in irritable bowel syndrome. PLoS One. 2013;8(3):e58204. doi: 10.1371/journal.pone.0058204. Epub 2013 Mar 13. [PubMed:23516449 ]
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 IDsNone
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FoodDB IDFDB030942
KNApSAcK IDNot Available
Chemspider ID6312
KEGG Compound IDC14710
BioCyc IDISOBUTANOL
BiGG IDNot Available
Wikipedia LinkIsobutanol
METLIN IDNot Available
PubChem Compound6560
PDB IDNot Available
ChEBI ID46645
Food Biomarker OntologyNot Available
VMH IDNot Available
References
Synthesis ReferenceNot Available
Material Safety Data Sheet (MSDS)Download (PDF)
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. 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 ]
  3. 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 ]
  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. 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 ]
  6. Evenepoel P, Meijers BK, Bammens BR, Verbeke K: Uremic toxins originating from colonic microbial metabolism. Kidney Int Suppl. 2009 Dec;(114):S12-9. doi: 10.1038/ki.2009.402. [PubMed:19946322 ]

Only showing the first 10 proteins. There are 33 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 33 proteins in total.