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Record Information

Version

5.0

Status

Expected but not Quantified

Creation Date

2012-09-11 17:40:01 UTC

Update Date

2023-02-21 17:19:48 UTC

HMDB ID

HMDB0030952

Secondary Accession Numbers

HMDB30952

Metabolite Identification

Common Name

2-Hexen-1-ol

Description

2-Hexen-1-ol (CAS: 2305-21-7), also known as 2-hexenyl alcohol, belongs to the class of organic compounds known as fatty alcohols. These are aliphatic alcohols consisting of a chain of a least six carbon atoms. The E-isomer has been isolated from tea and is a constituent of many fruits (e.g. apples, grapes). It is also present in asparagus (cooked or raw), cooked potato, cooked beef, beer, cognac, white wine, soybean and olives. The Z-isomer is found in cereals and cereal products, currants, and hops. The Z-isomer is also a food flavouring for baked goods and candies, producing a fresher note than the E-isomer.

Structure

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

View in JSmol View NMR Assignments View Stereo Labels

Synonyms

Value	Source
(e)-2-Hexen-1-ol	ChEBI
(e)-2-Hexenol	ChEBI
2-(e)-Hexenol	ChEBI
trans-2-Hexen-1-ol	ChEBI
trans-2-Hexenol	ChEBI
trans-Hex-2-en-1-ol	ChEBI
2-Hexenol	HMDB
2-Hexenyl alcohol	HMDB
3-Propylallyl alcohol	HMDB
FEMA 2562	HMDB
Hex-2-en-1-ol	HMDB
(2E)-2-Hexen-1-ol	HMDB
(E)-2-Hexene-1-ol	HMDB
1-Hydroxy-2-trans-hexene	HMDB
2-Hexen-1-ol	HMDB
n-Hex-trans-2-en-1-ol	HMDB
trans-2-Hexene-1-ol	HMDB
trans-4-Ethyl-2-buten-1-ol	HMDB

Chemical Formula

C₆H₁₂O

Average Molecular Weight

100.1589

Monoisotopic Molecular Weight

100.088815006

IUPAC Name

(2E)-hex-2-en-1-ol

Traditional Name

(2E)-hex-2-en-1-ol

CAS Registry Number

928-95-0

SMILES

CCC\C=C\CO

InChI Identifier

InChI=1S/C6H12O/c1-2-3-4-5-6-7/h4-5,7H,2-3,6H2,1H3/b5-4+

InChI Key

ZCHHRLHTBGRGOT-SNAWJCMRSA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as fatty alcohols. These are aliphatic alcohols consisting of a chain of a least six carbon atoms.

Kingdom

Organic compounds

Super Class

Lipids and lipid-like molecules

Class

Fatty Acyls

Sub Class

Fatty alcohols

Direct Parent

Fatty alcohols

Alternative Parents

Substituents

Fatty alcohol
Organic oxygen compound
Hydrocarbon derivative
Primary alcohol
Organooxygen compound
Alcohol
Aliphatic acyclic compound

Molecular Framework

Aliphatic acyclic compounds

External Descriptors

Fatty alcohols (LMFA05000060 )

Ontology

Not Available

Exogenous (HMDB: HMDB0030952)

Food

Fruit

Berry

Bilberry (FooDB: FOOD00193)
Highbush blueberry (FooDB: FOOD00191)

Cereal and cereal product

Cereal

Corn (FooDB: FOOD00205)
Common wheat (FooDB: FOOD00187)

Tea

Herb and spice

Herb

Spearmint (FooDB: FOOD00112)

Process

Not Available

Role

Not Available

Physical Properties

State

Liquid

Experimental Molecular Properties

Property	Value	Reference
Melting Point	Not Available	Not Available
Boiling Point	158.00 to 160.00 °C. @ 760.00 mm Hg	The Good Scents Company Information System
Water Solubility	16000 mg/L @ 25 °C (est)	The Good Scents Company Information System
LogP	1.655 (est)	The Good Scents Company Information System

Experimental Chromatographic Properties

Not Available

Predicted Molecular Properties

Property	Value	Source
Water Solubility	13.5 g/L	ALOGPS
logP	1.79	ALOGPS
logP	1.49	ChemAxon
logS	-0.87	ALOGPS
pKa (Strongest Acidic)	16.08	ChemAxon
pKa (Strongest Basic)	-2.3	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	3	ChemAxon
Refractivity	32.3 m³·mol⁻¹	ChemAxon
Polarizability	12.47 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]+	122.765	31661259
DarkChem	[M-H]-	118.157	31661259
DeepCCS	[M+H]+	126.673	30932474
DeepCCS	[M-H]-	124.67	30932474
DeepCCS	[M-2H]-	160.365	30932474
DeepCCS	[M+Na]+	134.839	30932474
AllCCS	[M+H]+	125.2	32859911
AllCCS	[M+H-H2O]+	120.7	32859911
AllCCS	[M+NH4]+	129.3	32859911
AllCCS	[M+Na]+	130.5	32859911
AllCCS	[M-H]-	130.8	32859911
AllCCS	[M+Na-2H]-	134.6	32859911
AllCCS	[M+HCOO]-	138.9	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.	3.29 minutes	32390414
Predicted by Siyang on May 30, 2022	12.2938 minutes	33406817
Predicted by Siyang using ReTip algorithm on June 8, 2022	5.07 minutes	32390414
AjsUoB = Accucore 150 Amide HILIC with 10mM Ammonium Formate, 0.1% Formic Acid	37.3 seconds	40023050
Fem_Long = Waters ACQUITY UPLC HSS T3 C18 with Water:MeOH and 0.1% Formic Acid	1714.7 seconds	40023050
Fem_Lipids = Ascentis Express C18 with (60:40 water:ACN):(90:10 IPA:ACN) and 10mM NH4COOH + 0.1% Formic Acid	378.9 seconds	40023050
Life_Old = Waters ACQUITY UPLC BEH C18 with Water:(20:80 acetone:ACN) and 0.1% Formic Acid	141.4 seconds	40023050
Life_New = RP Waters ACQUITY UPLC HSS T3 C18 with Water:(30:70 MeOH:ACN) and 0.1% Formic Acid	276.2 seconds	40023050
RIKEN = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	214.2 seconds	40023050
Eawag_XBridgeC18 = XBridge C18 3.5u 2.1x50 mm with Water:MeOH and 0.1% Formic Acid	473.0 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	464.8 seconds	40023050
HILIC_BDD_2 = Merck SeQuant ZIC-HILIC with ACN(0.1% formic acid):water(16 mM ammonium formate)	116.2 seconds	40023050
UniToyama_Atlantis = RP Waters Atlantis T3 (2.1 x 150 mm, 5 um) with ACN:Water and 0.1% Formic Acid	1041.1 seconds	40023050
BDD_C18 = Hypersil Gold 1.9µm C18 with Water:ACN and 0.1% Formic Acid	374.6 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	1140.5 seconds	40023050
SNU_RIKEN_POS = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	347.8 seconds	40023050
RPMMFDA = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	352.0 seconds	40023050
MTBLS87 = Merck SeQuant ZIC-pHILIC column with ACN:Water and :ammonium carbonate	458.8 seconds	40023050
KI_GIAR_zic_HILIC_pH2_7 = Merck SeQuant ZIC-HILIC with ACN:Water and 0.1% FA	387.8 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	34.3 seconds	40023050

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
2-Hexen-1-ol	CCC\C=C\CO	1353.1	Standard polar	33892256
2-Hexen-1-ol	CCC\C=C\CO	835.2	Standard non polar	33892256
2-Hexen-1-ol	CCC\C=C\CO	865.8	Semi standard non polar	33892256

Derivatized

Derivative Name / Structure	SMILES	Kovats RI Value	Column Type	Reference
2-Hexen-1-ol,1TMS,isomer #1	CCC/C=C/CO[Si](C)(C)C	1003.9	Semi standard non polar	33892256
2-Hexen-1-ol,1TBDMS,isomer #1	CCC/C=C/CO[Si](C)(C)C(C)(C)C	1215.9	Semi standard non polar	33892256

Spectra

GC-MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Experimental GC-MS	GC-MS Spectrum - 2-Hexen-1-ol EI-B (Non-derivatized)	splash10-0a4l-9000000000-0339132bed8a2355e193	2017-09-12	HMDB team, MONA, MassBank	View Spectrum
Experimental GC-MS	GC-MS Spectrum - 2-Hexen-1-ol EI-B (Non-derivatized)	splash10-0a4l-9000000000-0339132bed8a2355e193	2018-05-18	HMDB team, MONA, MassBank	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - 2-Hexen-1-ol GC-MS (Non-derivatized) - 70eV, Positive	splash10-004i-9000000000-905aec0105ffaa0f8a54	2016-09-22	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - 2-Hexen-1-ol GC-MS (1 TMS) - 70eV, Positive	splash10-00b9-9300000000-2528fa590b230a01811d	2017-10-06	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - 2-Hexen-1-ol GC-MS (Non-derivatized) - 70eV, Positive	Not Available	2021-10-12	Wishart Lab	View Spectrum
MS	Mass Spectrum (Electron Ionization)	splash10-0a4l-9000000000-268e830d9630be8d85ce	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-Hexen-1-ol 10V, Positive-QTOF	splash10-0f89-9600000000-968595b8d4e6d3a08780	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 2-Hexen-1-ol 20V, Positive-QTOF	splash10-001i-9200000000-7759daa71c78699b0f93	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 2-Hexen-1-ol 40V, Positive-QTOF	splash10-0536-9000000000-7b1defe2a4c09cc315ea	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 2-Hexen-1-ol 10V, Negative-QTOF	splash10-0002-9000000000-04ee26e1d76a08ecd25b	2016-08-04	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 2-Hexen-1-ol 20V, Negative-QTOF	splash10-0002-9000000000-4dfdd27e74949f0bde30	2016-08-04	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 2-Hexen-1-ol 40V, Negative-QTOF	splash10-00l6-9000000000-e40a439f7805bb132a5f	2016-08-04	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 2-Hexen-1-ol 10V, Positive-QTOF	splash10-0006-9000000000-2d161ddd25a52265b769	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 2-Hexen-1-ol 20V, Positive-QTOF	splash10-0a4l-9000000000-72de329808cbd75a61a1	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 2-Hexen-1-ol 40V, Positive-QTOF	splash10-0a4l-9000000000-010bb27b911a47cf3947	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 2-Hexen-1-ol 10V, Negative-QTOF	splash10-0002-9000000000-658fe53778817eb82301	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 2-Hexen-1-ol 20V, Negative-QTOF	splash10-001j-9000000000-70d4d9b58195f1cbf167	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 2-Hexen-1-ol 40V, Negative-QTOF	splash10-0pvl-9000000000-74c141b2d3e87a99fa41	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)	2021-09-30	Wishart Lab	View Spectrum
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, 1000 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, 200 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, 300 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, 400 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, 500 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, 600 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, 700 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, 800 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, 900 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

IR Spectra

Spectrum Type	Description	Deposition Date	Source	View
Predicted IR Spectrum	IR Ion Spectrum (Predicted IRIS Spectrum, Adduct: [M-H]-)	2023-02-03	FELIX lab	View Spectrum
Predicted IR Spectrum	IR Ion Spectrum (Predicted IRIS Spectrum, Adduct: [M+Na]+)	2023-02-03	FELIX lab	View Spectrum

Biological Properties

Cellular Locations

Cytoplasm
Extracellular
Membrane

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

FDB008090

KNApSAcK ID

C00000354

Chemspider ID

4476685

KEGG Compound ID

Not Available

BioCyc ID

TRANS-2-HEXENOL

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

5318042

PDB ID

Not Available

ChEBI ID

141205

Food Biomarker Ontology

Not Available

VMH ID

Not Available

MarkerDB ID

Not Available

Good Scents ID

rw1017731

References

Synthesis Reference

Not Available

Material Safety Data Sheet (MSDS)

Not Available

General References

Simons K, Toomre D: Lipid rafts and signal transduction. Nat Rev Mol Cell Biol. 2000 Oct;1(1):31-9. [PubMed:11413487 ]
Watson AD: Thematic review series: systems biology approaches to metabolic and cardiovascular disorders. Lipidomics: a global approach to lipid analysis in biological systems. J Lipid Res. 2006 Oct;47(10):2101-11. Epub 2006 Aug 10. [PubMed:16902246 ]
Sethi JK, Vidal-Puig AJ: Thematic review series: adipocyte biology. Adipose tissue function and plasticity orchestrate nutritional adaptation. J Lipid Res. 2007 Jun;48(6):1253-62. Epub 2007 Mar 20. [PubMed:17374880 ]
Lingwood D, Simons K: Lipid rafts as a membrane-organizing principle. Science. 2010 Jan 1;327(5961):46-50. doi: 10.1126/science.1174621. [PubMed:20044567 ]
(). Yannai, Shmuel. (2004) Dictionary of food compounds with CD-ROM: Additives, flavors, and ingredients. Boca Raton: Chapman & Hall/CRC.. .
Gunstone, Frank D., John L. Harwood, and Albert J. Dijkstra (2007). The lipid handbook with CD-ROM. CRC Press.

Showing metabocard for 2-Hexen-1-ol (HMDB0030952)

MOL for HMDB0030952 (2-Hexen-1-ol)

3D MOL for HMDB0030952 (2-Hexen-1-ol)

3D SDF for HMDB0030952 (2-Hexen-1-ol)

3D-SDF for HMDB0030952 (2-Hexen-1-ol)

PDB for HMDB0030952 (2-Hexen-1-ol)

3D PDB for HMDB0030952 (2-Hexen-1-ol)

SMILES for HMDB0030952 (2-Hexen-1-ol)

INCHI for HMDB0030952 (2-Hexen-1-ol)

Structure for HMDB0030952 (2-Hexen-1-ol)

3D Structure for HMDB0030952 (2-Hexen-1-ol)

Predicted Collision Cross Sections

Predicted Retention Times

Underivatized

Predicted Kovats Retention Indices

Underivatized

Derivatized

GC-MS Spectra

MS/MS Spectra

NMR Spectra

IR Spectra