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Record Information

Version

5.0

Status

Detected but not Quantified

Creation Date

2012-09-11 18:32:21 UTC

Update Date

2023-02-21 17:23:37 UTC

HMDB ID

HMDB0033777

Secondary Accession Numbers

HMDB33777

Metabolite Identification

Common Name

3-Methyl-2-butanol

Description

3-Methyl-2-butanol, also known as (CH3)2CHCH(OH)CH3 or 1,2-dimethylpropanol, belongs to the class of organic compounds known as secondary alcohols. Secondary alcohols are compounds containing a secondary alcohol functional group, with the general structure HOC(R)(R') (R,R'=alkyl, aryl). 3-Methyl-2-butanol (IUPAC name, commonly called sec-isoamyl alcohol) is an organic chemical compound. 3-Methyl-2-butanol is a fruity tasting compound. 3-methyl-2-butanol has been detected, but not quantified, in several different foods, such as alcoholic beverages, citrus, fruits, and pomes.

Structure

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

View in JSmol View NMR Assignments View Stereo Labels

Synonyms

Value	Source
(+/-)-3-methyl-2-butanol	ChEBI
(CH3)2chch(OH)CH3	ChEBI
1,2-Dimethyl-1-propanol	ChEBI
1,2-Dimethylpropanol	ChEBI
2-Methyl-3-butanol	ChEBI
DL-3-Methyl-2-butanol	ChEBI
Isopropylmethylcarbinol	ChEBI
Methylisopropylcarbinol	ChEBI
Sec-isoamyl alcohol	ChEBI
(+)-3-Methyl-2-butanol	HMDB
(S)-(+)-3-Methyl-2-butanol	HMDB
3-Methyl butan-2-ol	HMDB
3-Methyl-(S)-2-butanol	HMDB
3-Methyl-butan-2-ol	HMDB
3-Methylbutan-2-ol	HMDB
FEMA 3703	HMDB
Isopropyl methyl carbinol	HMDB

Chemical Formula

C₅H₁₂O

Average Molecular Weight

88.1482

Monoisotopic Molecular Weight

88.088815006

IUPAC Name

3-methylbutan-2-ol

Traditional Name

3-methyl-2-butanol

CAS Registry Number

598-75-4

SMILES

CC(C)C(C)O

InChI Identifier

InChI=1S/C5H12O/c1-4(2)5(3)6/h4-6H,1-3H3

InChI Key

MXLMTQWGSQIYOW-UHFFFAOYSA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as secondary alcohols. Secondary alcohols are compounds containing a secondary alcohol functional group, with the general structure HOC(R)(R') (R,R'=alkyl, aryl).

Kingdom

Organic compounds

Super Class

Organic oxygen compounds

Class

Organooxygen compounds

Sub Class

Alcohols and polyols

Direct Parent

Secondary alcohols

Alternative Parents

Hydrocarbon derivatives

Substituents

Secondary alcohol
Hydrocarbon derivative
Aliphatic acyclic compound

Molecular Framework

Aliphatic acyclic compounds

External Descriptors

secondary alcohol (CHEBI:77517 )

Ontology

Physiological effect

Organoleptic effect

Odor

Fruity

Feces (PMID: 24130822)

Cellular substructure

Extracellular (HMDB: HMDB0033777)
Cytoplasm (HMDB: HMDB0033777)

Route of exposure

Enteral

Ingestion (HMDB: HMDB0033777)

Source

Exogenous

Exogenous (HMDB: HMDB0033777)

Food

Food (HMDB: HMDB0033777)

Beverage

Fermented beverage

Beer (FooDB: FOOD00268)

Alcoholic beverage

Alcoholic beverages (FooDB: FOOD00854)

Fruit

Pome

Pomes (FooDB: FOOD00856)

Citrus

Citrus (FooDB: FOOD00859)

Fruits (FooDB: FOOD00871)

Endogenous

Plant

Plant (HMDB: HMDB0033777)

Process

Not Available

Role

Industrial application

Food and nutrition

Food additive

Flavoring agent

Flavoring Agent (HMDB: HMDB0033777)

Biological role

Nutrient (HMDB: HMDB0033777)

Physical Properties

State

Not Available

Experimental Molecular Properties

Property	Value	Reference
Melting Point	Not Available	Not Available
Boiling Point	112.00 to 114.00 °C. @ 760.00 mm Hg	The Good Scents Company Information System
Water Solubility	56 mg/mL at 25 °C	Not Available
LogP	1.28	Not Available

Experimental Chromatographic Properties

Not Available

Predicted Molecular Properties

Property	Value	Source
Water Solubility	69.2 g/L	ALOGPS
logP	0.89	ALOGPS
logP	1.14	ChemAxon
logS	-0.11	ALOGPS
pKa (Strongest Acidic)	18.18	ChemAxon
pKa (Strongest Basic)	-1.4	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	26.42 m³·mol⁻¹	ChemAxon
Polarizability	10.9 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]+	117.553	31661259
DarkChem	[M-H]-	112.272	31661259
DeepCCS	[M+H]+	124.054	30932474
DeepCCS	[M-H]-	122.08	30932474
DeepCCS	[M-2H]-	157.724	30932474
DeepCCS	[M+Na]+	132.344	30932474
AllCCS	[M+H]+	124.6	32859911
AllCCS	[M+H-H2O]+	120.3	32859911
AllCCS	[M+NH4]+	128.6	32859911
AllCCS	[M+Na]+	129.8	32859911
AllCCS	[M-H]-	130.5	32859911
AllCCS	[M+Na-2H]-	135.3	32859911
AllCCS	[M+HCOO]-	140.5	32859911

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
3-Methyl-2-butanol	CC(C)C(C)O	1077.1	Standard polar	33892256
3-Methyl-2-butanol	CC(C)C(C)O	651.3	Standard non polar	33892256
3-Methyl-2-butanol	CC(C)C(C)O	683.3	Semi standard non polar	33892256

Derivatized

Derivative Name / Structure	SMILES	Kovats RI Value	Column Type	Reference
3-Methyl-2-butanol,1TMS,isomer #1	CC(C)C(C)O[Si](C)(C)C	819.8	Semi standard non polar	33892256
3-Methyl-2-butanol,1TBDMS,isomer #1	CC(C)C(C)O[Si](C)(C)C(C)(C)C	1028.9	Semi standard non polar	33892256

Spectra

GC-MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Experimental GC-MS	GC-MS Spectrum - 3-Methyl-2-butanol EI-B (Non-derivatized)	splash10-0002-9000000000-44d9d7a94ff7c2651021	2017-09-12	HMDB team, MONA, MassBank	View Spectrum
Experimental GC-MS	GC-MS Spectrum - 3-Methyl-2-butanol EI-B (Non-derivatized)	splash10-0002-9000000000-44d9d7a94ff7c2651021	2018-05-18	HMDB team, MONA, MassBank	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - 3-Methyl-2-butanol GC-MS (Non-derivatized) - 70eV, Positive	splash10-0007-9000000000-78770a4dfd4ab1616562	2016-09-22	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - 3-Methyl-2-butanol GC-MS (1 TMS) - 70eV, Positive	splash10-01b9-9600000000-1d779ee9179b0fcf504a	2017-10-06	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - 3-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 - 3-Methyl-2-butanol GC-MS (Non-derivatized) - 70eV, Positive	Not Available	2021-10-12	Wishart Lab	View Spectrum

MS/MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 3-Methyl-2-butanol 10V, Positive-QTOF	splash10-00dr-9000000000-4ffd63b0ce27b825e1a4	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 3-Methyl-2-butanol 20V, Positive-QTOF	splash10-00dr-9000000000-786b15ebd2470655b181	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 3-Methyl-2-butanol 40V, Positive-QTOF	splash10-05fu-9000000000-3bafa42c637f0dc58765	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 3-Methyl-2-butanol 10V, Negative-QTOF	splash10-000i-9000000000-84df5a19c5fe06f51111	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 3-Methyl-2-butanol 20V, Negative-QTOF	splash10-000i-9000000000-2d4f8096c4f2056b5942	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 3-Methyl-2-butanol 40V, Negative-QTOF	splash10-00dr-9000000000-095d06adb31802845012	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 3-Methyl-2-butanol 10V, Negative-QTOF	splash10-000i-9000000000-dd8f1f11d4928285c04e	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 3-Methyl-2-butanol 20V, Negative-QTOF	splash10-000i-9000000000-d19500853c2051ed857e	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 3-Methyl-2-butanol 40V, Negative-QTOF	splash10-0006-9000000000-974b32fa427a46bc6ce0	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 3-Methyl-2-butanol 10V, Positive-QTOF	splash10-00di-9000000000-d08e71ee8dc88f8b3c63	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 3-Methyl-2-butanol 20V, Positive-QTOF	splash10-05fu-9000000000-25c97e1634d54d006168	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 3-Methyl-2-butanol 40V, Positive-QTOF	splash10-052f-9000000000-ccb8f3acdd5694f9b66e	2021-09-22	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

Feces

Tissue Locations

Not Available

Pathways

Not Available

Name	SMPDB/PathBank	KEGG

Normal Concentrations

Biospecimen	Status	Value	Age	Sex	Condition	Reference	Details
Feces	Detected but not Quantified	Not Quantified	Children (1-13 years old)	Both	Normal	24130822	details

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

FDB011931

KNApSAcK ID

Not Available

Chemspider ID

11239

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

3-Methyl-2-butanol

METLIN ID

Not Available

PubChem Compound

11732

PDB ID

Not Available

ChEBI ID

77517

Food Biomarker Ontology

Not Available

VMH ID

Not Available

MarkerDB ID

Not Available

Good Scents ID

rw1037501

References

Synthesis Reference

Not Available

Material Safety Data Sheet (MSDS)

Not Available

General References

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

Showing metabocard for 3-Methyl-2-butanol (HMDB0033777)

MOL for HMDB0033777 (3-Methyl-2-butanol)

3D MOL for HMDB0033777 (3-Methyl-2-butanol)

3D SDF for HMDB0033777 (3-Methyl-2-butanol)

3D-SDF for HMDB0033777 (3-Methyl-2-butanol)

PDB for HMDB0033777 (3-Methyl-2-butanol)

3D PDB for HMDB0033777 (3-Methyl-2-butanol)

SMILES for HMDB0033777 (3-Methyl-2-butanol)

INCHI for HMDB0033777 (3-Methyl-2-butanol)

Structure for HMDB0033777 (3-Methyl-2-butanol)

3D Structure for HMDB0033777 (3-Methyl-2-butanol)

Predicted Collision Cross Sections

Predicted Kovats Retention Indices

Underivatized

Derivatized

GC-MS Spectra

MS/MS Spectra

NMR Spectra

IR Spectra