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Record Information
Version5.0
StatusExpected but not Quantified
Creation Date2012-09-11 18:32:02 UTC
Update Date2021-10-13 06:35:20 UTC
HMDB IDHMDB0033772
Secondary Accession Numbers
  • HMDB33772
Metabolite Identification
Common Name2-Methyl-2-butanol
Description2-Methyl-2-butanol, also known as t-amyl alcohol (TAA) or amylene hydrate, belongs to the class of organic compounds known as tertiary alcohols. Tertiary alcohols are compounds in which a hydroxy group, -OH, is attached to a saturated carbon atom R3COH (R not H). 2-Methyl-2-butanol is a pungent tasting compound. 2-methyl-2-butanol has been detected, but not quantified, in several different foods, such as red bell peppers, pepper (c. annuum), fruits, yellow bell peppers, and orange bell peppers. This could make 2-methyl-2-butanol a potential biomarker for the consumption of these foods. In 1930's TAA was mainly used as a solvent for tribromoethanol (TBE), forming Avertin at a 0.5:1 volume ratio of TAA to TBE. When ingested, the effects of TAA may begin in about 30 minutes and can last up to 2 days. The oral LD50 in rats is 1 g/kg.
Structure
Data?1563862457
Synonyms
ValueSource
1,1-Dimethyl-1-propanolChEBI
2m2bChEBI
3-Methylbutan-3-olChEBI
Amylene hydrateChEBI
Dimethyl ethyl carbinolChEBI
DimethylethylcarbinolChEBI
Ethyl dimethyl carbinolChEBI
EthyldimethylcarbinolChEBI
t-Amyl alcoholChEBI
t-Pentyl alcoholChEBI
Tert-amyl alcoholChEBI
Tert-isoamyl alcoholChEBI
Tert-pentanolChEBI
Tert-pentyl alcoholChEBI
Amylene hydric acidGenerator
Methyl butanolMeSH
Potassium t-amylateMeSH
2-BUTANOL,2-methylHMDB
2-Methyl butanol-2HMDB
2-Methyl-2-butanol (tert-amyl alcohol)HMDB
2-Methylbutan-2-olHMDB
3-Methyl-butanol-(3)HMDB
Amylalkohol, tertiaererHMDB
Amylene hydrate (NF)HMDB
Amylene hydrate, usanHMDB
Amylenum hydratumHMDB
C2H5C(CH3)2ohHMDB
Methyl-2 butanol-2HMDB
Methyl-3 butanol-3HMDB
Tert-N-amyl alcoholHMDB
2-Methyl-2-butanolChEBI
Chemical FormulaC5H12O
Average Molecular Weight88.1482
Monoisotopic Molecular Weight88.088815006
IUPAC Name2-methylbutan-2-ol
Traditional Name2-methyl-2-butanol
CAS Registry Number75-85-4
SMILES
CCC(C)(C)O
InChI Identifier
InChI=1S/C5H12O/c1-4-5(2,3)6/h6H,4H2,1-3H3
InChI KeyMSXVEPNJUHWQHW-UHFFFAOYSA-N
Chemical Taxonomy
Description Belongs to the class of organic compounds known as tertiary alcohols. Tertiary alcohols are compounds in which a hydroxy group, -OH, is attached to a saturated carbon atom R3COH (R not H ).
KingdomOrganic compounds
Super ClassOrganic oxygen compounds
ClassOrganooxygen compounds
Sub ClassAlcohols and polyols
Direct ParentTertiary alcohols
Alternative Parents
Substituents
  • Tertiary alcohol
  • Hydrocarbon derivative
  • Aliphatic acyclic compound
Molecular FrameworkAliphatic acyclic compounds
External DescriptorsNot Available
Ontology
Disposition

Biological location

Source

Route of exposure

Physical Properties
StateLiquid
Experimental Molecular Properties
PropertyValueReference
Melting Point-8.4 °CNot Available
Boiling Point246.00 to 247.00 °C. @ 760.00 mm Hg (est)The Good Scents Company Information System
Water Solubility110 mg/mL at 25 °CNot Available
LogP0.89Not Available
Experimental Chromatographic PropertiesNot Available
Predicted Molecular Properties
PropertyValueSource
Water Solubility55.8 g/LALOGPS
logP10(1.19) g/LALOGPS
logP10(1.06) g/LChemAxon
logS10(-0.2) g/LALOGPS
pKa (Strongest Acidic)18.54ChemAxon
pKa (Strongest Basic)-1.3ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count1ChemAxon
Hydrogen Donor Count1ChemAxon
Polar Surface Area20.23 ŲChemAxon
Rotatable Bond Count1ChemAxon
Refractivity26.59 m³·mol⁻¹ChemAxon
Polarizability10.83 ųChemAxon
Number of Rings0ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterNoChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleNoChemAxon
Predicted Chromatographic Properties

Predicted Collision Cross Sections

PredictorAdduct TypeCCS Value (Å2)Reference
DarkChem[M+H]+116.94731661259
DarkChem[M-H]-112.03331661259

Predicted Kovats Retention Indices

Underivatized

MetaboliteSMILESKovats RI ValueColumn TypeReference
2-Methyl-2-butanolCCC(C)(C)O978.6Standard polar33892256
2-Methyl-2-butanolCCC(C)(C)O630.3Standard non polar33892256
2-Methyl-2-butanolCCC(C)(C)O614.6Semi standard non polar33892256

Derivatized

Derivative Name / StructureSMILESKovats RI ValueColumn TypeReference
2-Methyl-2-butanol,1TMS,isomer #1CCC(C)(C)O[Si](C)(C)C798.7Semi standard non polar33892256
2-Methyl-2-butanol,1TBDMS,isomer #1CCC(C)(C)O[Si](C)(C)C(C)(C)C1019.7Semi standard non polar33892256
Spectra

GC-MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Experimental GC-MSGC-MS Spectrum - 2-Methyl-2-butanol EI-B (Non-derivatized)splash10-0a4i-9000000000-e28240c1ea5d94b4b4df2017-09-12HMDB team, MONA, MassBankView Spectrum
Experimental GC-MSGC-MS Spectrum - 2-Methyl-2-butanol EI-B (Non-derivatized)splash10-0a4i-9000000000-0821ab0d9a052553bbfa2017-09-12HMDB team, MONA, MassBankView Spectrum
Experimental GC-MSGC-MS Spectrum - 2-Methyl-2-butanol EI-B (Non-derivatized)splash10-0ab9-9000000000-0baeab474747cad029812017-09-12HMDB team, MONA, MassBankView Spectrum
Experimental GC-MSGC-MS Spectrum - 2-Methyl-2-butanol EI-B (Non-derivatized)splash10-0a4i-9000000000-3c51f1bef3465a1ccd852017-09-12HMDB team, MONA, MassBankView Spectrum
Experimental GC-MSGC-MS Spectrum - 2-Methyl-2-butanol EI-B (Non-derivatized)splash10-0a4i-9000000000-e28240c1ea5d94b4b4df2018-05-18HMDB team, MONA, MassBankView Spectrum
Experimental GC-MSGC-MS Spectrum - 2-Methyl-2-butanol EI-B (Non-derivatized)splash10-0a4i-9000000000-0821ab0d9a052553bbfa2018-05-18HMDB team, MONA, MassBankView Spectrum
Experimental GC-MSGC-MS Spectrum - 2-Methyl-2-butanol EI-B (Non-derivatized)splash10-0ab9-9000000000-0baeab474747cad029812018-05-18HMDB team, MONA, MassBankView Spectrum
Experimental GC-MSGC-MS Spectrum - 2-Methyl-2-butanol EI-B (Non-derivatized)splash10-0a4i-9000000000-3c51f1bef3465a1ccd852018-05-18HMDB team, MONA, MassBankView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - 2-Methyl-2-butanol GC-MS (Non-derivatized) - 70eV, Positivesplash10-0a4i-9000000000-b0c96fb57bf5c113a09a2017-09-01Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - 2-Methyl-2-butanol GC-MS (1 TMS) - 70eV, Positivesplash10-00gv-9400000000-38d2291c57fca8c5dfa42017-10-06Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - 2-Methyl-2-butanol GC-MS (Non-derivatized) - 70eV, PositiveNot Available2021-10-12Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - 2-Methyl-2-butanol GC-MS (Non-derivatized) - 70eV, PositiveNot Available2021-10-12Wishart LabView Spectrum
MSMass Spectrum (Electron Ionization)splash10-0a4i-9000000000-fba7029fc9e5c16b1c5a2015-03-01Not AvailableView Spectrum

MS/MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 2-Methyl-2-butanol 10V, Positive-QTOFsplash10-00di-9000000000-abab8cea46d09ee5e4242016-06-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 2-Methyl-2-butanol 20V, Positive-QTOFsplash10-00di-9000000000-4c7b7c0cee175989e99e2016-06-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 2-Methyl-2-butanol 40V, Positive-QTOFsplash10-0ab9-9000000000-b03ea02f6f2d6c01c0e92016-06-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 2-Methyl-2-butanol 10V, Negative-QTOFsplash10-000i-9000000000-10f4bd33cb4e7b25cc012016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 2-Methyl-2-butanol 20V, Negative-QTOFsplash10-00kr-9000000000-49967558d2d9251d79d62016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 2-Methyl-2-butanol 40V, Negative-QTOFsplash10-0gi9-9000000000-ec91c528afd7d7b2e8432016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 2-Methyl-2-butanol 10V, Negative-QTOFsplash10-000i-9000000000-dd8f1f11d4928285c04e2021-09-21Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 2-Methyl-2-butanol 20V, Negative-QTOFsplash10-000i-9000000000-819d1a0b56c4e7c493752021-09-21Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 2-Methyl-2-butanol 40V, Negative-QTOFsplash10-059i-9000000000-579816bc0a5940a547cb2021-09-21Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 2-Methyl-2-butanol 10V, Positive-QTOFsplash10-00di-9000000000-c98a9be1afec8085ce802021-09-25Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 2-Methyl-2-butanol 20V, Positive-QTOFsplash10-05fu-9000000000-2525f4a12960cd90ea612021-09-25Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 2-Methyl-2-butanol 40V, Positive-QTOFsplash10-052f-9000000000-ef6b994ba6b711892a8a2021-09-25Wishart 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
Biological Properties
Cellular Locations
  • Cytoplasm
  • Extracellular
Biospecimen LocationsNot Available
Tissue LocationsNot Available
Pathways
Normal Concentrations
Not Available
Abnormal Concentrations
Not Available
Associated Disorders and Diseases
Disease ReferencesNone
Associated OMIM IDsNone
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FooDB IDFDB011925
KNApSAcK IDNot Available
Chemspider ID6165
KEGG Compound IDNot Available
BioCyc IDCPD-19059
BiGG IDNot Available
Wikipedia LinkTert-Amyl_alcohol
METLIN IDNot Available
PubChem Compound6405
PDB IDNot Available
ChEBI ID132750
Food Biomarker OntologyNot Available
VMH IDNot Available
MarkerDB IDNot Available
Good Scents IDrw1516611
References
Synthesis ReferenceNot Available
Material Safety Data Sheet (MSDS)Not Available
General References
  1. Wolodko WT, James MN, Bridger WA: Crystallization of succinyl-CoA synthetase from Escherichia coli. J Biol Chem. 1984 Apr 25;259(8):5316-20. [PubMed:6371002 ]
  2. (). Yannai, Shmuel. (2004) Dictionary of food compounds with CD-ROM: Additives, flavors, and ingredients. Boca Raton: Chapman & Hall/CRC.. .