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Record Information

Version

5.0

Status

Expected but not Quantified

Creation Date

2012-09-11 18:32:02 UTC

Update Date

2023-02-21 17:23:36 UTC

HMDB ID

HMDB0033772

Secondary Accession Numbers

HMDB33772

Metabolite Identification

Common Name

2-Methyl-2-butanol

Description

2-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

MOL 3D MOL SDF 3D SDF PDB 3D PDB SMILES InChI

View in JSmol View NMR Assignments View Stereo Labels

Synonyms

Value	Source
1,1-Dimethyl-1-propanol	ChEBI
2m2b	ChEBI
3-Methylbutan-3-ol	ChEBI
Amylene hydrate	ChEBI
Dimethyl ethyl carbinol	ChEBI
Dimethylethylcarbinol	ChEBI
Ethyl dimethyl carbinol	ChEBI
Ethyldimethylcarbinol	ChEBI
t-Amyl alcohol	ChEBI
t-Pentyl alcohol	ChEBI
Tert-amyl alcohol	ChEBI
Tert-isoamyl alcohol	ChEBI
Tert-pentanol	ChEBI
Tert-pentyl alcohol	ChEBI
Amylene hydric acid	Generator
Methyl butanol	MeSH
Potassium t-amylate	MeSH
2-BUTANOL,2-methyl	HMDB
2-Methyl butanol-2	HMDB
2-Methyl-2-butanol (tert-amyl alcohol)	HMDB
2-Methylbutan-2-ol	HMDB
3-Methyl-butanol-(3)	HMDB
Amylalkohol, tertiaerer	HMDB
Amylene hydrate (NF)	HMDB
Amylene hydrate, usan	HMDB
Amylenum hydratum	HMDB
C2H5C(CH3)2oh	HMDB
Methyl-2 butanol-2	HMDB
Methyl-3 butanol-3	HMDB
Tert-N-amyl alcohol	HMDB
2-Methyl-2-butanol	ChEBI

Chemical Formula

C₅H₁₂O

Average Molecular Weight

88.1482

Monoisotopic Molecular Weight

88.088815006

IUPAC Name

2-methylbutan-2-ol

Traditional Name

2-methyl-2-butanol

CAS Registry Number

75-85-4

SMILES

CCC(C)(C)O

InChI Identifier

InChI=1S/C5H12O/c1-4-5(2,3)6/h6H,4H2,1-3H3

InChI Key

MSXVEPNJUHWQHW-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 ).

Kingdom

Organic compounds

Super Class

Organic oxygen compounds

Class

Organooxygen compounds

Sub Class

Alcohols and polyols

Direct Parent

Tertiary alcohols

Alternative Parents

Hydrocarbon derivatives

Substituents

Tertiary alcohol
Hydrocarbon derivative
Aliphatic acyclic compound

Molecular Framework

Aliphatic acyclic compounds

External Descriptors

Not Available

Ontology

Physiological effect

Organoleptic effect

Taste

Pungent

Disposition

Biological location

Cellular substructure

Extracellular (HMDB: HMDB0033772)
Cytoplasm (HMDB: HMDB0033772)

Route of exposure

Enteral

Ingestion (HMDB: HMDB0033772)

Source

Exogenous

Exogenous (HMDB: HMDB0033772)

Food

Food (HMDB: HMDB0033772)

Beverage

Fermented beverage

Grape wine (FooDB: FOOD00612)

Fruit

Pome

Apple (FooDB: FOOD00105)

Fruits (FooDB: FOOD00871)

Berry

Evergreen blackberry (FooDB: FOOD00901)
Blackberry (FooDB: FOOD00906)

Vegetable

Root vegetable

Celeriac (FooDB: FOOD00214)

Fruit vegetable

Endogenous

Plant

Plant (HMDB: HMDB0033772)

Process

Not Available

Role

Biological role

Nutrient (HMDB: HMDB0033772)

Physical Properties

State

Liquid

Experimental Molecular Properties

Property	Value	Reference
Melting Point	-8.4 °C	Not Available
Boiling Point	246.00 to 247.00 °C. @ 760.00 mm Hg (est)	The Good Scents Company Information System
Water Solubility	110 mg/mL at 25 °C	Not Available
LogP	0.89	Not Available

Experimental Chromatographic Properties

Not Available

Predicted Molecular Properties

Property	Value	Source
Water Solubility	55.8 g/L	ALOGPS
logP	1.19	ALOGPS
logP	1.06	ChemAxon
logS	-0.2	ALOGPS
pKa (Strongest Acidic)	18.54	ChemAxon
pKa (Strongest Basic)	-1.3	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	1	ChemAxon
Hydrogen Donor Count	1	ChemAxon
Polar Surface Area	20.23 Å²	ChemAxon
Rotatable Bond Count	1	ChemAxon
Refractivity	26.59 m³·mol⁻¹	ChemAxon
Polarizability	10.83 Å³	ChemAxon
Number of Rings	0	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	No	ChemAxon
Veber's Rule	Yes	ChemAxon
MDDR-like Rule	No	ChemAxon

Predicted Chromatographic Properties

Predicted Collision Cross Sections

Predictor	Adduct Type	CCS Value (Å²)	Reference
DarkChem	[M+H]+	116.947	31661259
DarkChem	[M-H]-	112.033	31661259
DeepCCS	[M+H]+	127.073	30932474
DeepCCS	[M-H]-	124.979	30932474
DeepCCS	[M-2H]-	160.835	30932474
DeepCCS	[M+Na]+	135.472	30932474
AllCCS	[M+H]+	122.0	32859911
AllCCS	[M+H-H2O]+	117.6	32859911
AllCCS	[M+NH4]+	126.2	32859911
AllCCS	[M+Na]+	127.4	32859911
AllCCS	[M-H]-	130.5	32859911
AllCCS	[M+Na-2H]-	135.3	32859911
AllCCS	[M+HCOO]-	140.5	32859911

Predicted Retention Times

Underivatized

Chromatographic Method	Retention Time	Reference
Measured using a Waters Acquity ultraperformance liquid chromatography (UPLC) ethylene-bridged hybrid (BEH) C18 column (100 mm × 2.1 mm; 1.7 μmparticle diameter). Predicted by Afia on May 17, 2022. Predicted by Afia on May 17, 2022.	1.78 minutes	32390414
Predicted by Siyang on May 30, 2022	12.64 minutes	33406817
Predicted by Siyang using ReTip algorithm on June 8, 2022	4.8 minutes	32390414
AjsUoB = Accucore 150 Amide HILIC with 10mM Ammonium Formate, 0.1% Formic Acid	37.5 seconds	40023050
Fem_Long = Waters ACQUITY UPLC HSS T3 C18 with Water:MeOH and 0.1% Formic Acid	1629.3 seconds	40023050
Fem_Lipids = Ascentis Express C18 with (60:40 water:ACN):(90:10 IPA:ACN) and 10mM NH4COOH + 0.1% Formic Acid	448.4 seconds	40023050
Life_Old = Waters ACQUITY UPLC BEH C18 with Water:(20:80 acetone:ACN) and 0.1% Formic Acid	154.0 seconds	40023050
Life_New = RP Waters ACQUITY UPLC HSS T3 C18 with Water:(30:70 MeOH:ACN) and 0.1% Formic Acid	272.7 seconds	40023050
RIKEN = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	110.2 seconds	40023050
Eawag_XBridgeC18 = XBridge C18 3.5u 2.1x50 mm with Water:MeOH and 0.1% Formic Acid	544.4 seconds	40023050
BfG_NTS_RP1 =Agilent Zorbax Eclipse Plus C18 (2.1 mm x 150 mm, 3.5 um) with Water:ACN and 0.1% Formic Acid	582.1 seconds	40023050
HILIC_BDD_2 = Merck SeQuant ZIC-HILIC with ACN(0.1% formic acid):water(16 mM ammonium formate)	136.7 seconds	40023050
UniToyama_Atlantis = RP Waters Atlantis T3 (2.1 x 150 mm, 5 um) with ACN:Water and 0.1% Formic Acid	878.9 seconds	40023050
BDD_C18 = Hypersil Gold 1.9µm C18 with Water:ACN and 0.1% Formic Acid	328.6 seconds	40023050
UFZ_Phenomenex = Kinetex Core-Shell C18 2.6 um, 3.0 x 100 mm, Phenomenex with Water:MeOH and 0.1% Formic Acid	1153.0 seconds	40023050
SNU_RIKEN_POS = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	364.4 seconds	40023050
RPMMFDA = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	314.5 seconds	40023050
MTBLS87 = Merck SeQuant ZIC-pHILIC column with ACN:Water and :ammonium carbonate	469.3 seconds	40023050
KI_GIAR_zic_HILIC_pH2_7 = Merck SeQuant ZIC-HILIC with ACN:Water and 0.1% FA	472.9 seconds	40023050
Meister zic-pHILIC pH9.3 = Merck SeQuant ZIC-pHILIC column with ACN:Water 5mM NH4Ac pH9.3 and 5mM ammonium acetate in water	58.7 seconds	40023050

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
2-Methyl-2-butanol	CCC(C)(C)O	978.6	Standard polar	33892256
2-Methyl-2-butanol	CCC(C)(C)O	630.3	Standard non polar	33892256
2-Methyl-2-butanol	CCC(C)(C)O	614.6	Semi standard non polar	33892256

Derivatized

Derivative Name / Structure	SMILES	Kovats RI Value	Column Type	Reference
2-Methyl-2-butanol,1TMS,isomer #1	CCC(C)(C)O[Si](C)(C)C	798.7	Semi standard non polar	33892256
2-Methyl-2-butanol,1TBDMS,isomer #1	CCC(C)(C)O[Si](C)(C)C(C)(C)C	1019.7	Semi standard non polar	33892256

Spectra

GC-MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Experimental GC-MS	GC-MS Spectrum - 2-Methyl-2-butanol EI-B (Non-derivatized)	splash10-0a4i-9000000000-e28240c1ea5d94b4b4df	2017-09-12	HMDB team, MONA, MassBank	View Spectrum
Experimental GC-MS	GC-MS Spectrum - 2-Methyl-2-butanol EI-B (Non-derivatized)	splash10-0a4i-9000000000-0821ab0d9a052553bbfa	2017-09-12	HMDB team, MONA, MassBank	View Spectrum
Experimental GC-MS	GC-MS Spectrum - 2-Methyl-2-butanol EI-B (Non-derivatized)	splash10-0ab9-9000000000-0baeab474747cad02981	2017-09-12	HMDB team, MONA, MassBank	View Spectrum
Experimental GC-MS	GC-MS Spectrum - 2-Methyl-2-butanol EI-B (Non-derivatized)	splash10-0a4i-9000000000-3c51f1bef3465a1ccd85	2017-09-12	HMDB team, MONA, MassBank	View Spectrum
Experimental GC-MS	GC-MS Spectrum - 2-Methyl-2-butanol EI-B (Non-derivatized)	splash10-0a4i-9000000000-e28240c1ea5d94b4b4df	2018-05-18	HMDB team, MONA, MassBank	View Spectrum
Experimental GC-MS	GC-MS Spectrum - 2-Methyl-2-butanol EI-B (Non-derivatized)	splash10-0a4i-9000000000-0821ab0d9a052553bbfa	2018-05-18	HMDB team, MONA, MassBank	View Spectrum
Experimental GC-MS	GC-MS Spectrum - 2-Methyl-2-butanol EI-B (Non-derivatized)	splash10-0ab9-9000000000-0baeab474747cad02981	2018-05-18	HMDB team, MONA, MassBank	View Spectrum
Experimental GC-MS	GC-MS Spectrum - 2-Methyl-2-butanol EI-B (Non-derivatized)	splash10-0a4i-9000000000-3c51f1bef3465a1ccd85	2018-05-18	HMDB team, MONA, MassBank	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - 2-Methyl-2-butanol GC-MS (Non-derivatized) - 70eV, Positive	splash10-0a4i-9000000000-b0c96fb57bf5c113a09a	2017-09-01	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - 2-Methyl-2-butanol GC-MS (1 TMS) - 70eV, Positive	splash10-00gv-9400000000-38d2291c57fca8c5dfa4	2017-10-06	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - 2-Methyl-2-butanol GC-MS (Non-derivatized) - 70eV, Positive	Not Available	2021-10-12	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - 2-Methyl-2-butanol GC-MS (Non-derivatized) - 70eV, Positive	Not Available	2021-10-12	Wishart Lab	View Spectrum
MS	Mass Spectrum (Electron Ionization)	splash10-0a4i-9000000000-fba7029fc9e5c16b1c5a	2015-03-01	Not Available	View Spectrum

MS/MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 2-Methyl-2-butanol 10V, Positive-QTOF	splash10-00di-9000000000-abab8cea46d09ee5e424	2016-06-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 2-Methyl-2-butanol 20V, Positive-QTOF	splash10-00di-9000000000-4c7b7c0cee175989e99e	2016-06-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 2-Methyl-2-butanol 40V, Positive-QTOF	splash10-0ab9-9000000000-b03ea02f6f2d6c01c0e9	2016-06-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 2-Methyl-2-butanol 10V, Negative-QTOF	splash10-000i-9000000000-10f4bd33cb4e7b25cc01	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 2-Methyl-2-butanol 20V, Negative-QTOF	splash10-00kr-9000000000-49967558d2d9251d79d6	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 2-Methyl-2-butanol 40V, Negative-QTOF	splash10-0gi9-9000000000-ec91c528afd7d7b2e843	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 2-Methyl-2-butanol 10V, Negative-QTOF	splash10-000i-9000000000-dd8f1f11d4928285c04e	2021-09-21	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 2-Methyl-2-butanol 20V, Negative-QTOF	splash10-000i-9000000000-819d1a0b56c4e7c49375	2021-09-21	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 2-Methyl-2-butanol 40V, Negative-QTOF	splash10-059i-9000000000-579816bc0a5940a547cb	2021-09-21	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 2-Methyl-2-butanol 10V, Positive-QTOF	splash10-00di-9000000000-c98a9be1afec8085ce80	2021-09-25	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 2-Methyl-2-butanol 20V, Positive-QTOF	splash10-05fu-9000000000-2525f4a12960cd90ea61	2021-09-25	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 2-Methyl-2-butanol 40V, Positive-QTOF	splash10-052f-9000000000-ef6b994ba6b711892a8a	2021-09-25	Wishart Lab	View Spectrum

NMR Spectra

Spectrum Type	Description	Deposition Date	Source	View
Predicted 1D NMR	¹H NMR Spectrum (1D, 100 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 100 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 1000 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 1000 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 200 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 200 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 300 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 300 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 400 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 400 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 500 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 500 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 600 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 600 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 700 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 700 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 800 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 800 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 900 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 900 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum

IR Spectra

Spectrum Type	Description	Deposition Date	Source	View
Predicted IR Spectrum	IR Ion Spectrum (Predicted IRIS Spectrum, Adduct: [M-H]-)	2023-02-04	FELIX lab	View Spectrum
Predicted IR Spectrum	IR Ion Spectrum (Predicted IRIS Spectrum, Adduct: [M+H]+)	2023-02-04	FELIX lab	View Spectrum
Predicted IR Spectrum	IR Ion Spectrum (Predicted IRIS Spectrum, Adduct: [M+Na]+)	2023-02-04	FELIX lab	View Spectrum

Biological Properties

Cellular Locations

Cytoplasm
Extracellular

Biospecimen Locations

Not Available

Tissue Locations

Not Available

Pathways

Not Available

Name	SMPDB/PathBank	KEGG

Normal Concentrations

Not Available

Abnormal Concentrations

Not Available

Associated Disorders and Diseases

Disease References

None

Associated OMIM IDs

None

External Links

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FooDB ID

FDB011925

KNApSAcK ID

Not Available

Chemspider ID

6165

KEGG Compound ID

Not Available

BioCyc ID

CPD-19059

BiGG ID

Not Available

Wikipedia Link

Tert-Amyl_alcohol

METLIN ID

Not Available

PubChem Compound

6405

PDB ID

Not Available

ChEBI ID

132750

Food Biomarker Ontology

Not Available

VMH ID

Not Available

MarkerDB ID

Not Available

Good Scents ID

rw1516611

References

Synthesis Reference

Not Available

Material Safety Data Sheet (MSDS)

Not Available

General References

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 ]
(). Yannai, Shmuel. (2004) Dictionary of food compounds with CD-ROM: Additives, flavors, and ingredients. Boca Raton: Chapman & Hall/CRC.. .

Showing metabocard for 2-Methyl-2-butanol (HMDB0033772)

MOL for HMDB0033772 (2-Methyl-2-butanol)

3D MOL for HMDB0033772 (2-Methyl-2-butanol)

3D SDF for HMDB0033772 (2-Methyl-2-butanol)

3D-SDF for HMDB0033772 (2-Methyl-2-butanol)

PDB for HMDB0033772 (2-Methyl-2-butanol)

3D PDB for HMDB0033772 (2-Methyl-2-butanol)

SMILES for HMDB0033772 (2-Methyl-2-butanol)

INCHI for HMDB0033772 (2-Methyl-2-butanol)

Structure for HMDB0033772 (2-Methyl-2-butanol)

3D Structure for HMDB0033772 (2-Methyl-2-butanol)

Predicted Collision Cross Sections

Predicted Retention Times

Underivatized

Predicted Kovats Retention Indices

Underivatized

Derivatized

GC-MS Spectra

MS/MS Spectra

NMR Spectra

IR Spectra