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Identification Taxonomy Ontology Physical properties Spectra Biological properties Concentrations Links References XML

Record Information

Version

5.0

Status

Detected but not Quantified

Creation Date

2014-10-08 15:56:36 UTC

Update Date

2023-02-21 17:30:32 UTC

HMDB ID

HMDB0061886

Secondary Accession Numbers

HMDB61886

Metabolite Identification

Common Name

2-Hexanol

Description

2-Hexanol, also known as hexan-2-ol, 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). 2-Hexanol is a very hydrophobic molecule, practically insoluble in water, and relatively neutral. Thus, 2-hexanol is considered to be a fatty alcohol lipid molecule. 2-Hexanol (or hexan-2-ol) is a six carbon alcohol in which the OH group is located on the second carbon atom. Its chemical formula is C6H14O or C6H13OH. 2-Hexanol is a chemical and winey tasting compound. 2-Hexanol is found, on average, in the highest concentration within safflowers. 2-Hexanol has also been detected, but not quantified, in several different foods, such as pepper (c. frutescens), tea, green bell peppers, corns, and orange bell peppers. This could make 2-hexanol a potential biomarker for the consumption of these foods. 2-Hexanol, with regard to humans, has been linked to the inborn metabolic disorder celiac disease. It is an isomer of the other hexanols. 2-Hexanol has a chiral center and can be resolved into enantiomers.

Structure

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

View in JSmol View NMR Assignments View Stereo Labels

Synonyms

Value	Source
Hexan-2-ol	HMDB

Chemical Formula

C₆H₁₄O

Average Molecular Weight

102.1748

Monoisotopic Molecular Weight

102.10446507

IUPAC Name

hexan-2-ol

Traditional Name

2-hexanol

CAS Registry Number

Not Available

SMILES

CCCCC(C)O

InChI Identifier

InChI=1S/C6H14O/c1-3-4-5-6(2)7/h6-7H,3-5H2,1-2H3

InChI Key

QNVRIHYSUZMSGM-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

Fatty alcohols (LMFA05000467 )

Ontology

Non-excretory biofluid

Biofluid or Excreta

Saliva (HMDB: HMDB0061886)

Source

Exogenous

Food

Cereal and cereal product

Cereal

Corn (FooDB: FOOD00205)

Herb and spice

Oilseed crop

Safflower (FooDB: FOOD00042)

Vegetable

Fruit vegetable

Pepper (FooDB: FOOD00040)
Green bell pepper (FooDB: FOOD00877)
Yellow bell pepper (FooDB: FOOD00878)
Red bell pepper (FooDB: FOOD00880)
Pepper (C. frutescens) (FooDB: FOOD00428)
Orange bell pepper (FooDB: FOOD00879)

Tea

Process

Not Available

Role

Not Available

Physical Properties

State

Not Available

Experimental Molecular Properties

Property	Value	Reference
Melting Point	Not Available	Not Available
Boiling Point	Not Available	Not Available
Water Solubility	Not Available	Not Available
LogP	Not Available	Not Available

Experimental Chromatographic Properties

Not Available

Predicted Molecular Properties

Property	Value	Source
Water Solubility	17.2 g/L	ALOGPS
logP	1.75	ALOGPS
logP	1.67	ChemAxon
logS	-0.77	ALOGPS
pKa (Strongest Acidic)	17.68	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	3	ChemAxon
Refractivity	31.15 m³·mol⁻¹	ChemAxon
Polarizability	13.04 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]+	121.401	31661259
DarkChem	[M-H]-	116.852	31661259
DeepCCS	[M+H]+	131.993	30932474
DeepCCS	[M-H]-	130.097	30932474
DeepCCS	[M-2H]-	165.74	30932474
DeepCCS	[M+Na]+	140.277	30932474
AllCCS	[M+H]+	126.7	32859911
AllCCS	[M+H-H2O]+	122.3	32859911
AllCCS	[M+NH4]+	130.8	32859911
AllCCS	[M+Na]+	132.0	32859911
AllCCS	[M-H]-	130.5	32859911
AllCCS	[M+Na-2H]-	134.4	32859911
AllCCS	[M+HCOO]-	138.7	32859911

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
2-Hexanol	CCCCC(C)O	1167.7	Standard polar	33892256
2-Hexanol	CCCCC(C)O	772.3	Standard non polar	33892256
2-Hexanol	CCCCC(C)O	789.0	Semi standard non polar	33892256

Derivatized

Derivative Name / Structure	SMILES	Kovats RI Value	Column Type	Reference
2-Hexanol,1TMS,isomer #1	CCCCC(C)O[Si](C)(C)C	933.4	Semi standard non polar	33892256
2-Hexanol,1TBDMS,isomer #1	CCCCC(C)O[Si](C)(C)C(C)(C)C	1126.5	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-Hexanol EI-B (Non-derivatized)	splash10-0002-9000000000-d2359b7e811b8b064741	2017-09-12	HMDB team, MONA, MassBank	View Spectrum
Experimental GC-MS	GC-MS Spectrum - 2-Hexanol EI-B (Non-derivatized)	splash10-052g-9000000000-5ed68fbbaa3fc418b8c9	2017-09-12	HMDB team, MONA, MassBank	View Spectrum
Experimental GC-MS	GC-MS Spectrum - 2-Hexanol EI-B (Non-derivatized)	splash10-0002-9000000000-4c27b69e9102343f0cba	2017-09-12	HMDB team, MONA, MassBank	View Spectrum
Experimental GC-MS	GC-MS Spectrum - 2-Hexanol CI-B (Non-derivatized)	splash10-000i-9000000000-6a2465fd6b8f6d61c645	2017-09-12	HMDB team, MONA, MassBank	View Spectrum
Experimental GC-MS	GC-MS Spectrum - 2-Hexanol EI-B (Non-derivatized)	splash10-0002-9000000000-13cf4a6ddf1472a5e7af	2017-09-12	HMDB team, MONA, MassBank	View Spectrum
Experimental GC-MS	GC-MS Spectrum - 2-Hexanol EI-B (Non-derivatized)	splash10-0002-9000000000-025559fc240ab827b146	2017-09-12	HMDB team, MONA, MassBank	View Spectrum
Experimental GC-MS	GC-MS Spectrum - 2-Hexanol EI-B (Non-derivatized)	splash10-0002-9000000000-d2359b7e811b8b064741	2018-05-18	HMDB team, MONA, MassBank	View Spectrum
Experimental GC-MS	GC-MS Spectrum - 2-Hexanol EI-B (Non-derivatized)	splash10-052g-9000000000-5ed68fbbaa3fc418b8c9	2018-05-18	HMDB team, MONA, MassBank	View Spectrum
Experimental GC-MS	GC-MS Spectrum - 2-Hexanol EI-B (Non-derivatized)	splash10-0002-9000000000-4c27b69e9102343f0cba	2018-05-18	HMDB team, MONA, MassBank	View Spectrum
Experimental GC-MS	GC-MS Spectrum - 2-Hexanol CI-B (Non-derivatized)	splash10-000i-9000000000-6a2465fd6b8f6d61c645	2018-05-18	HMDB team, MONA, MassBank	View Spectrum
Experimental GC-MS	GC-MS Spectrum - 2-Hexanol EI-B (Non-derivatized)	splash10-0002-9000000000-13cf4a6ddf1472a5e7af	2018-05-18	HMDB team, MONA, MassBank	View Spectrum
Experimental GC-MS	GC-MS Spectrum - 2-Hexanol EI-B (Non-derivatized)	splash10-0002-9000000000-025559fc240ab827b146	2018-05-18	HMDB team, MONA, MassBank	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - 2-Hexanol GC-MS (Non-derivatized) - 70eV, Positive	splash10-052g-9000000000-52e19fa4c4bcd06646a6	2016-09-22	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - 2-Hexanol GC-MS (1 TMS) - 70eV, Positive	splash10-06g3-9500000000-b66c1dd8ded5f6316d10	2017-10-06	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - 2-Hexanol GC-MS (Non-derivatized) - 70eV, Positive	Not Available	2021-10-12	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - 2-Hexanol GC-MS (Non-derivatized) - 70eV, Positive	Not Available	2021-10-12	Wishart Lab	View Spectrum
MS	Mass Spectrum (Electron Ionization)	splash10-0002-9000000000-0ebe978c5d40bd72e235	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-Hexanol 10V, Positive-QTOF	splash10-000i-9200000000-721b46c83f2085e83494	2016-08-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 2-Hexanol 20V, Positive-QTOF	splash10-000i-9100000000-084ab1dd479565a37a5b	2016-08-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 2-Hexanol 40V, Positive-QTOF	splash10-052f-9000000000-fa8209fe0c9c5bbe8d15	2016-08-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 2-Hexanol 10V, Negative-QTOF	splash10-0udi-2900000000-1f6dc02c43b345b910ed	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 2-Hexanol 20V, Negative-QTOF	splash10-0ue9-8900000000-91731673e906063261b0	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 2-Hexanol 40V, Negative-QTOF	splash10-0a59-9000000000-91d8c1ca99e3b966a532	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 2-Hexanol 10V, Positive-QTOF	splash10-052o-9000000000-0e7e4db53cdac561ab61	2021-09-23	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 2-Hexanol 20V, Positive-QTOF	splash10-0a4l-9000000000-863b41a57d92f57fba8d	2021-09-23	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 2-Hexanol 40V, Positive-QTOF	splash10-0006-9000000000-71fa8f2a4182b2e25a8a	2021-09-23	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 2-Hexanol 10V, Negative-QTOF	splash10-0udi-0900000000-3ab02485eaffb4e83bff	2021-09-25	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 2-Hexanol 20V, Negative-QTOF	splash10-0f8a-9300000000-cca82d56e84604d1fd25	2021-09-25	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 2-Hexanol 40V, Negative-QTOF	splash10-0a4i-9000000000-0bf90c6bbf926b02dc88	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)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 100 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 1000 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 1000 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 200 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 200 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 300 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 300 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 400 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 400 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 500 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 500 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 600 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 600 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 700 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 700 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 800 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 800 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 900 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 900 MHz, D₂O, predicted)	2021-09-24	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

Not Available

Biospecimen Locations

Saliva

Tissue Locations

Not Available

Pathways

Not Available

Name	SMPDB/PathBank	KEGG

Normal Concentrations

Biospecimen	Status	Value	Age	Sex	Condition	Reference	Details
Saliva	Detected but not Quantified	Not Quantified	Children (1-13 years old)	Both	Normal	24657864	details

Abnormal Concentrations

Biospecimen	Status	Value	Age	Sex	Condition	Reference	Details
Saliva	Detected but not Quantified	Not Quantified	Children (1-13 years old)	Both	Celiac disease	24657864	details

Associated Disorders and Diseases

Disease References

Celiac disease
Francavilla R, Ercolini D, Piccolo M, Vannini L, Siragusa S, De Filippis F, De Pasquale I, Di Cagno R, Di Toma M, Gozzi G, Serrazanetti DI, De Angelis M, Gobbetti M: Salivary microbiota and metabolome associated with celiac disease. Appl Environ Microbiol. 2014 Jun;80(11):3416-25. doi: 10.1128/AEM.00362-14. Epub 2014 Mar 21. [PubMed:24657864 ]

Associated OMIM IDs

212750 (Celiac disease)

External Links

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FooDB ID

FDB004514

KNApSAcK ID

Not Available

Chemspider ID

11794

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

2-Hexanol

METLIN ID

Not Available

PubChem Compound

12297

PDB ID

Not Available

ChEBI ID

Not Available

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)

Not Available

General References

Perbellini L, De Grandis D, Semenzato F, Rizzuto N, Simonati A: An experimental study on the neurotoxicity of n-hexane metabolites: hexanol-1 and hexanol-2. Toxicol Appl Pharmacol. 1978 Nov;46(2):421-7. [PubMed:734671 ]
Yoshida Y, Liu J, Sugiura T, Ishidao T, Ueno S, Yanagita H, Fueta Y, Kunugita N, Hori H, Yamashita U: The indoor air pollutant 2-ethyl-hexanol activates CD4 cells. Chem Biol Interact. 2009 Jan 27;177(2):137-41. doi: 10.1016/j.cbi.2008.10.053. Epub 2008 Nov 6. [PubMed:19038237 ]
Gallego-Iniesta Garcia MP, Moreno Sanroma A, Martin Porrero MP, Tapia Valle A, Cabanas Galan B, Salgado Munoz MS: Reactivity of 2-ethyl-1-hexanol in the atmosphere. Phys Chem Chem Phys. 2010 Apr 7;12(13):3294-300. doi: 10.1039/b923899a. Epub 2010 Feb 19. [PubMed:20237722 ]
McGinty D, Scognamiglio J, Letizia CS, Api AM: Fragrance material review on 2-ethyl-1-hexanol. Food Chem Toxicol. 2010 Jul;48 Suppl 4:S115-29. doi: 10.1016/j.fct.2010.05.042. [PubMed:20659633 ]
Wikipedia [Link]
Scott A. Stevenson, Wugeng Liang, 'INTEGRATED PLANT FOR PRODUCING 2-ETHYL-HEXANOL AND METHACRYLIC ACID.' U.S. Patent US20100260647, issued October 14, 2010. [Link]

Showing metabocard for 2-Hexanol (HMDB0061886)

MOL for HMDB0061886 (2-Hexanol)

3D MOL for HMDB0061886 (2-Hexanol)

3D SDF for HMDB0061886 (2-Hexanol)

3D-SDF for HMDB0061886 (2-Hexanol)

PDB for HMDB0061886 (2-Hexanol)

3D PDB for HMDB0061886 (2-Hexanol)

SMILES for HMDB0061886 (2-Hexanol)

INCHI for HMDB0061886 (2-Hexanol)

Structure for HMDB0061886 (2-Hexanol)

3D Structure for HMDB0061886 (2-Hexanol)

Predicted Collision Cross Sections

Predicted Kovats Retention Indices

Underivatized

Derivatized

GC-MS Spectra

MS/MS Spectra

NMR Spectra

IR Spectra