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Record Information

Version

5.0

Status

Detected but not Quantified

Creation Date

2012-09-11 17:44:17 UTC

Update Date

2023-02-21 17:20:57 UTC

HMDB ID

HMDB0031599

Secondary Accession Numbers

HMDB31599

Metabolite Identification

Common Name

2-Pentanol

Description

2-Pentanol, also known as 1-methylbutanol or 2-hydroxypentane, belongs to the class of organic compounds known as secondary alcohols. A secondary alcohol that is pentane substituted at position 2 by a hydroxy group. Secondary alcohols are compounds containing a secondary alcohol functional group, with the general structure HOC(R)(R') (R,R'=alkyl, aryl). 2-Pentanol has been detected, but not quantified, in a few different foods, such as alcoholic beverages, fruits, and milk and milk products.

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-Methyl-1-butanol	ChEBI
1-Methylbutanol	ChEBI
2-Hydroxypentane	ChEBI
2-Pentyl alcohol	ChEBI
alpha-Methylbutanol	ChEBI
Methyl propyl carbinol	ChEBI
Methylpropylcarbinol	ChEBI
N-C3H7CH(OH)CH3	ChEBI
Pentanol-2	ChEBI
Sec-amyl alcohol	ChEBI
Sec-N-amyl alcohol	ChEBI
Sec-pentanol	ChEBI
Sec-pentyl alcohol	ChEBI
a-Methylbutanol	Generator
Α-methylbutanol	Generator
(+/-)-2-pentanol	ChEBI, HMDB
(R)-(-)-2-Pentanol	HMDB
(S)-(+)-2-Pentanol	HMDB
FEMA 3316	HMDB
Isoamyl alcohol (primary/secondary	HMDB
Isoamyl alcohol, secondary	HMDB
Methyl butanol	HMDB, MeSH
Methyl-butanol	HMDB
Methylbutan-1-ol	HMDB
Pentan-2-ol	HMDB
Potassium t-amylate	MeSH, HMDB
t-Amyl alcohol	MeSH, HMDB
Tert-amyl alcohol	MeSH, HMDB
2-Methyl-2-butanol	MeSH, HMDB
2-Pentanol	ChEBI

Chemical Formula

C₅H₁₂O

Average Molecular Weight

88.1482

Monoisotopic Molecular Weight

88.088815006

IUPAC Name

pentan-2-ol

Traditional Name

2-pentanol

CAS Registry Number

6032-29-7

SMILES

CCCC(C)O

InChI Identifier

InChI=1S/C5H12O/c1-3-4-5(2)6/h5-6H,3-4H2,1-2H3

InChI Key

JYVLIDXNZAXMDK-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:77518 )

Ontology

Feces (PMID: 17314143)

Cellular substructure

Extracellular (HMDB: HMDB0031599)
Cytoplasm (HMDB: HMDB0031599)

Source

Exogenous

Exogenous (HMDB: HMDB0031599)

Food

Fruit

Pome

Apple (FooDB: FOOD00105)

Berry

Blackcurrant (FooDB: FOOD00155)

Vegetable

Shoot vegetable

Asparagus (FooDB: FOOD00021)

Cereal and cereal product

Cereal

Corn (FooDB: FOOD00205)

Gourd

Cucumber (FooDB: FOOD00065)

Herb and spice

Spice

Ginger (FooDB: FOOD00206)

Herb

Rosemary (FooDB: FOOD00159)

Milk and milk product

Unfermented milk

Milk (Cow) (FooDB: FOOD00618)

Process

Not Available

Role

Not Available

Physical Properties

State

Liquid

Experimental Molecular Properties

Property	Value	Reference
Melting Point	-73 °C	Not Available
Boiling Point	Not Available	Not Available
Water Solubility	44.6 mg/mL at 25 °C	Not Available
LogP	1.19	Not Available

Experimental Chromatographic Properties

Not Available

Predicted Molecular Properties

Property	Value	Source
Water Solubility	59.7 g/L	ALOGPS
logP	1.18	ALOGPS
logP	1.22	ChemAxon
logS	-0.17	ALOGPS
pKa (Strongest Acidic)	17.8	ChemAxon
pKa (Strongest Basic)	-1.6	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	2	ChemAxon
Refractivity	26.55 m³·mol⁻¹	ChemAxon
Polarizability	11.02 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]+	116.955	31661259
DarkChem	[M-H]-	111.836	31661259
DeepCCS	[M+H]+	127.733	30932474
DeepCCS	[M-H]-	125.823	30932474
DeepCCS	[M-2H]-	161.34	30932474
DeepCCS	[M+Na]+	135.896	30932474
AllCCS	[M+H]+	123.7	32859911
AllCCS	[M+H-H2O]+	119.2	32859911
AllCCS	[M+NH4]+	127.9	32859911
AllCCS	[M+Na]+	129.1	32859911
AllCCS	[M-H]-	130.8	32859911
AllCCS	[M+Na-2H]-	135.4	32859911
AllCCS	[M+HCOO]-	140.5	32859911

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
2-Pentanol	CCCC(C)O	1078.1	Standard polar	33892256
2-Pentanol	CCCC(C)O	664.7	Standard non polar	33892256
2-Pentanol	CCCC(C)O	681.7	Semi standard non polar	33892256

Derivatized

Derivative Name / Structure	SMILES	Kovats RI Value	Column Type	Reference
2-Pentanol,1TMS,isomer #1	CCCC(C)O[Si](C)(C)C	854.1	Semi standard non polar	33892256
2-Pentanol,1TBDMS,isomer #1	CCCC(C)O[Si](C)(C)C(C)(C)C	1038.0	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-Pentanol EI-B (Non-derivatized)	splash10-0a4i-9000000000-19815e3dcbfcbbccaa40	2017-09-12	HMDB team, MONA, MassBank	View Spectrum
Experimental GC-MS	GC-MS Spectrum - 2-Pentanol EI-B (Non-derivatized)	splash10-0002-9000000000-ee11af6c4a561b5c9bbd	2017-09-12	HMDB team, MONA, MassBank	View Spectrum
Experimental GC-MS	GC-MS Spectrum - 2-Pentanol EI-B (Non-derivatized)	splash10-052e-9000000000-f0deb638d3edc45dc66a	2017-09-12	HMDB team, MONA, MassBank	View Spectrum
Experimental GC-MS	GC-MS Spectrum - 2-Pentanol EI-B (Non-derivatized)	splash10-0002-9000000000-0ae80db19f0a4f6f52a0	2017-09-12	HMDB team, MONA, MassBank	View Spectrum
Experimental GC-MS	GC-MS Spectrum - 2-Pentanol EI-B (Non-derivatized)	splash10-0a4i-9000000000-19815e3dcbfcbbccaa40	2018-05-18	HMDB team, MONA, MassBank	View Spectrum
Experimental GC-MS	GC-MS Spectrum - 2-Pentanol EI-B (Non-derivatized)	splash10-0002-9000000000-ee11af6c4a561b5c9bbd	2018-05-18	HMDB team, MONA, MassBank	View Spectrum
Experimental GC-MS	GC-MS Spectrum - 2-Pentanol EI-B (Non-derivatized)	splash10-052e-9000000000-f0deb638d3edc45dc66a	2018-05-18	HMDB team, MONA, MassBank	View Spectrum
Experimental GC-MS	GC-MS Spectrum - 2-Pentanol EI-B (Non-derivatized)	splash10-0002-9000000000-0ae80db19f0a4f6f52a0	2018-05-18	HMDB team, MONA, MassBank	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - 2-Pentanol GC-MS (Non-derivatized) - 70eV, Positive	splash10-00bd-9000000000-a3bfc45a4f28beaf892a	2017-09-01	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - 2-Pentanol GC-MS (1 TMS) - 70eV, Positive	splash10-00fs-9300000000-baaea12ff9e62ed7bf43	2017-10-06	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - 2-Pentanol GC-MS (Non-derivatized) - 70eV, Positive	Not Available	2021-10-12	Wishart Lab	View Spectrum
MS	Mass Spectrum (Electron Ionization)	splash10-0002-9000000000-2b92c1ebfce84d9a189e	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-Pentanol 10V, Positive-QTOF	splash10-00di-9000000000-cc4515b70c83fa4565c7	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 2-Pentanol 20V, Positive-QTOF	splash10-00di-9000000000-df91948909c8c4143cb8	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 2-Pentanol 40V, Positive-QTOF	splash10-00dl-9000000000-ea6d1efc64a3bd41a96d	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 2-Pentanol 10V, Negative-QTOF	splash10-000i-9000000000-b0aeeb1eafd7d5f3272c	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 2-Pentanol 20V, Negative-QTOF	splash10-00kr-9000000000-bb0d405de9c11645e924	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 2-Pentanol 40V, Negative-QTOF	splash10-00r6-9000000000-2de1088b9048aeb662d9	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 2-Pentanol 10V, Negative-QTOF	splash10-000i-9000000000-dd8f1f11d4928285c04e	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 2-Pentanol 20V, Negative-QTOF	splash10-000i-9000000000-f1a24274609e9756e7f5	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 2-Pentanol 40V, Negative-QTOF	splash10-0a4l-9000000000-12883dab736685ea1ad2	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 2-Pentanol 10V, Positive-QTOF	splash10-006x-9000000000-cf94ca13278156b9ade0	2021-09-23	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 2-Pentanol 20V, Positive-QTOF	splash10-0006-9000000000-f09a556f6ed79c51a833	2021-09-23	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 2-Pentanol 40V, Positive-QTOF	splash10-0006-9000000000-bf2500ef794fea0a76ad	2021-09-23	Wishart Lab	View Spectrum

NMR Spectra

Spectrum Type	Description	Deposition Date	Source	View
Predicted 1D NMR	¹³C NMR Spectrum (1D, 100 MHz, D₂O, predicted)	2021-09-30	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 100 MHz, D₂O, predicted)	2021-09-30	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 1000 MHz, D₂O, predicted)	2021-09-30	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 1000 MHz, D₂O, predicted)	2021-09-30	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 200 MHz, D₂O, predicted)	2021-09-30	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 200 MHz, D₂O, predicted)	2021-09-30	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 300 MHz, D₂O, predicted)	2021-09-30	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 300 MHz, D₂O, predicted)	2021-09-30	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 400 MHz, D₂O, predicted)	2021-09-30	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 400 MHz, D₂O, predicted)	2021-09-30	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 500 MHz, D₂O, predicted)	2021-09-30	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 500 MHz, D₂O, predicted)	2021-09-30	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 600 MHz, D₂O, predicted)	2021-09-30	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 600 MHz, D₂O, predicted)	2021-09-30	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 700 MHz, D₂O, predicted)	2021-09-30	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 700 MHz, D₂O, predicted)	2021-09-30	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 800 MHz, D₂O, predicted)	2021-09-30	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 800 MHz, D₂O, predicted)	2021-09-30	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 900 MHz, D₂O, predicted)	2021-09-30	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 900 MHz, D₂O, predicted)	2021-09-30	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	Adult (>18 years old)	Both	Normal	17314143	details
Feces	Detected but not Quantified	Not Quantified	Adult (>18 years old)	Both	Normal	19167006	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

FDB011151

KNApSAcK ID

C00035493

Chemspider ID

21011

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

2-Pentanol

METLIN ID

Not Available

PubChem Compound

22386

PDB ID

Not Available

ChEBI ID

77518

Food Biomarker Ontology

Not Available

VMH ID

Not Available

MarkerDB ID

Not Available

Good Scents ID

Not Available

References

Synthesis Reference

Not Available

Material Safety Data Sheet (MSDS)

Download (PDF)

General References

Dierkes G, Bongartz A, Guth H, Hayen H: Quality evaluation of olive oil by statistical analysis of multicomponent stable isotope dilution assay data of aroma active compounds. J Agric Food Chem. 2012 Jan 11;60(1):394-401. doi: 10.1021/jf203406s. Epub 2011 Dec 12. [PubMed:22117816 ]
Ziadi M, Wathelet JP, Marlier M, Hamdi M, Thonart P: Analysis of volatile compounds produced by 2 strains of Lactococcus lactis isolated from leben (Tunisian fermented milk) using solid-phase microextraction-gas chromatography. J Food Sci. 2008 Aug;73(6):S247-52. [PubMed:19241567 ]
Afzal MI, Boulahya KA, Paris C, Delaunay S, Cailliez-Grimal C: Effect of oxygen on the biosynthesis of flavor compound 3-methylbutanal from leucine catabolism during batch culture in Carnobacterium maltaromaticum LMA 28. J Dairy Sci. 2013 Jan;96(1):352-9. doi: 10.3168/jds.2012-6088. Epub 2012 Nov 22. [PubMed:23182362 ]
Fall PA, Pilet MF, Leduc F, Cardinal M, Duflos G, Guerin C, Joffraud JJ, Leroi F: Sensory and physicochemical evolution of tropical cooked peeled shrimp inoculated by Brochothrix thermosphacta and Lactococcus piscium CNCM I-4031 during storage at 8 degrees C. Int J Food Microbiol. 2012 Jan 16;152(3):82-90. doi: 10.1016/j.ijfoodmicro.2011.07.015. Epub 2011 Jul 23. [PubMed:21835482 ]
Mo X, Xu Y, Fan W: Characterization of aroma compounds in Chinese rice wine Qu by solvent-assisted flavor evaporation and headspace solid-phase microextraction. J Agric Food Chem. 2010 Feb 24;58(4):2462-9. doi: 10.1021/jf903631w. [PubMed:20088505 ]
Holm ES, Schafer A, Skov T, Koch AG, Petersen MA: Identification of chemical markers for the sensory shelf-life of saveloy. Meat Sci. 2012 Feb;90(2):314-22. doi: 10.1016/j.meatsci.2011.07.017. Epub 2011 Jul 30. [PubMed:21856089 ]
Jary E, Bee T, Walker SR, Chung SK, Seo KC, Morris JC, Don AS: Elimination of a hydroxyl group in FTY720 dramatically improves the phosphorylation rate. Mol Pharmacol. 2010 Oct;78(4):685-92. doi: 10.1124/mol.110.064873. Epub 2010 Jul 7. [PubMed:20610734 ]
Garcia-Cayuela T, Gomez de Cadinanos LP, Pelaez C, Requena T: Expression in Lactococcus lactis of functional genes related to amino acid catabolism and cheese aroma formation is influenced by branched chain amino acids. Int J Food Microbiol. 2012 Oct 15;159(3):207-13. doi: 10.1016/j.ijfoodmicro.2012.09.002. Epub 2012 Sep 13. [PubMed:23107499 ]
Rowan DD, Hunt MB, Dimouro A, Alspach PA, Weskett R, Volz RK, Gardiner SE, Chagne D: Profiling fruit volatiles in the progeny of a 'Royal Gala' x 'Granny Smith' apple (Malus x domestica) cross. J Agric Food Chem. 2009 Sep 9;57(17):7953-61. doi: 10.1021/jf901678v. [PubMed:19691320 ]
Sun SY, Jiang WG, Zhao YP: Evaluation of different Saccharomyces cerevisiae strains on the profile of volatile compounds and polyphenols in cherry wines. Food Chem. 2011 Jul 15;127(2):547-55. doi: 10.1016/j.foodchem.2011.01.039. Epub 2011 Jan 19. [PubMed:23140699 ]
McGinty D, Scognamiglio J, Letizia CS, Api AM: Fragrance material review on 2-methylbutanol. Food Chem Toxicol. 2010 Jul;48 Suppl 4:S97-101. doi: 10.1016/j.fct.2010.05.039. [PubMed:20659647 ]
Holm ES, Schafer A, Koch AG, Petersen MA: Investigation of spoilage in saveloy samples inoculated with four potential spoilage bacteria. Meat Sci. 2013 Mar;93(3):687-95. doi: 10.1016/j.meatsci.2012.11.016. Epub 2012 Nov 16. [PubMed:23261532 ]
Andrade MA, Cordoba JJ, Casado EM, Cordoba MG, Rodriguez M: Effect of selected strains of Debaryomyces hansenii on the volatile compound production of dry fermented sausage "salchichon". Meat Sci. 2010 Jun;85(2):256-64. doi: 10.1016/j.meatsci.2010.01.009. Epub 2010 Jan 14. [PubMed:20374895 ]
Van Lancker F, Adams A, Delmulle B, De Saeger S, Moretti A, Van Peteghem C, De Kimpe N: Use of headspace SPME-GC-MS for the analysis of the volatiles produced by indoor molds grown on different substrates. J Environ Monit. 2008 Oct;10(10):1127-33. doi: 10.1039/b808608g. [PubMed:18843388 ]
Chou HH, Keasling JD: Synthetic pathway for production of five-carbon alcohols from isopentenyl diphosphate. Appl Environ Microbiol. 2012 Nov;78(22):7849-55. doi: 10.1128/AEM.01175-12. Epub 2012 Aug 31. [PubMed:22941086 ]
(). Yannai, Shmuel. (2004) Dictionary of food compounds with CD-ROM: Additives, flavors, and ingredients. Boca Raton: Chapman & Hall/CRC.. .

Showing metabocard for 2-Pentanol (HMDB0031599)

MOL for HMDB0031599 (2-Pentanol)

3D MOL for HMDB0031599 (2-Pentanol)

3D SDF for HMDB0031599 (2-Pentanol)

3D-SDF for HMDB0031599 (2-Pentanol)

PDB for HMDB0031599 (2-Pentanol)

3D PDB for HMDB0031599 (2-Pentanol)

SMILES for HMDB0031599 (2-Pentanol)

INCHI for HMDB0031599 (2-Pentanol)

Structure for HMDB0031599 (2-Pentanol)

3D Structure for HMDB0031599 (2-Pentanol)

Predicted Collision Cross Sections

Predicted Kovats Retention Indices

Underivatized

Derivatized

GC-MS Spectra

MS/MS Spectra

NMR Spectra

IR Spectra