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Record Information

Version

5.0

Status

Expected but not Quantified

Creation Date

2012-09-12 01:44:52 UTC

Update Date

2023-02-21 17:27:54 UTC

HMDB ID

HMDB0040210

Secondary Accession Numbers

HMDB40210

Metabolite Identification

Common Name

2-Propenyl hexanoate

Description

2-Propenyl hexanoate, also known as allyl caproate, allocopen, or allyl hexanoate is an organic compound with the formula C5H11CO2CH2CH=CH2. It is a colorless liquid, although commercial samples appear yellowish. It occurs naturally in pineapples. It belongs to the class of organic compounds known as fatty acid esters. These are carboxylic ester derivatives of a fatty acid. 2-Propenyl hexanoate is a very hydrophobic molecule, practically insoluble in water, and relatively neutral. Allyl hexanoate is employed principally in the formulation of pineapple flavors but it can also be used for peach and apricot essences and for apple blossom, peach blossom, and wisteria perfume compositions. It is an ingredient of some lipstick perfumes. It also adds a sweet juicy note to citrus flavors.

Structure

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

COMPND    HMDB0040210
HETATM    1  C1  UNL     1      -5.487   0.728  -0.010  1.00  0.00           C  
HETATM    2  C2  UNL     1      -4.636  -0.258  -0.253  1.00  0.00           C  
HETATM    3  C3  UNL     1      -3.311   0.032  -0.865  1.00  0.00           C  
HETATM    4  O1  UNL     1      -2.291  -0.388   0.003  1.00  0.00           O  
HETATM    5  C4  UNL     1      -0.968  -0.211  -0.373  1.00  0.00           C  
HETATM    6  O2  UNL     1      -0.744   0.326  -1.492  1.00  0.00           O  
HETATM    7  C5  UNL     1       0.151  -0.649   0.533  1.00  0.00           C  
HETATM    8  C6  UNL     1       1.454  -0.307  -0.185  1.00  0.00           C  
HETATM    9  C7  UNL     1       2.642  -0.729   0.688  1.00  0.00           C  
HETATM   10  C8  UNL     1       3.897  -0.365  -0.077  1.00  0.00           C  
HETATM   11  C9  UNL     1       3.853   1.138  -0.295  1.00  0.00           C  
HETATM   12  H1  UNL     1      -5.247   1.753  -0.245  1.00  0.00           H  
HETATM   13  H2  UNL     1      -6.443   0.485   0.435  1.00  0.00           H  
HETATM   14  H3  UNL     1      -4.875  -1.285  -0.020  1.00  0.00           H  
HETATM   15  H4  UNL     1      -3.263  -0.453  -1.867  1.00  0.00           H  
HETATM   16  H5  UNL     1      -3.200   1.122  -1.034  1.00  0.00           H  
HETATM   17  H6  UNL     1       0.077  -0.150   1.509  1.00  0.00           H  
HETATM   18  H7  UNL     1       0.028  -1.738   0.646  1.00  0.00           H  
HETATM   19  H8  UNL     1       1.522   0.760  -0.417  1.00  0.00           H  
HETATM   20  H9  UNL     1       1.458  -0.866  -1.143  1.00  0.00           H  
HETATM   21  H10 UNL     1       2.583  -1.784   0.950  1.00  0.00           H  
HETATM   22  H11 UNL     1       2.644  -0.109   1.607  1.00  0.00           H  
HETATM   23  H12 UNL     1       3.787  -0.821  -1.096  1.00  0.00           H  
HETATM   24  H13 UNL     1       4.815  -0.678   0.430  1.00  0.00           H  
HETATM   25  H14 UNL     1       3.308   1.389  -1.232  1.00  0.00           H  
HETATM   26  H15 UNL     1       3.342   1.586   0.560  1.00  0.00           H  
HETATM   27  H16 UNL     1       4.906   1.474  -0.375  1.00  0.00           H  
CONECT    1    2    2   12   13
CONECT    2    3   14
CONECT    3    4   15   16
CONECT    4    5
CONECT    5    6    6    7
CONECT    7    8   17   18
CONECT    8    9   19   20
CONECT    9   10   21   22
CONECT   10   11   23   24
CONECT   11   25   26   27
END

View in JSmol View Stereo Labels

Synonyms

Value	Source
2-Propenyl hexanoic acid	Generator
2-Propenyl N-hexanoate	HMDB
Allocopen	HMDB
Allyl caproate	HMDB, MeSH
Allyl hexanoate	HMDB
Allyl N-caproate	HMDB
Allyl N-hexanoate	HMDB
Allylester kyseliny kapronove	HMDB
FEMA 2032	HMDB
Hexanoic acid, 2-propen-1-yl ester	HMDB
Hexanoic acid, 2-propenyl ester	HMDB
Hexanoic acid, allyl ester	HMDB

Chemical Formula

C₉H₁₆O₂

Average Molecular Weight

156.2221

Monoisotopic Molecular Weight

156.115029756

IUPAC Name

prop-2-en-1-yl hexanoate

Traditional Name

allyl caproate

CAS Registry Number

123-68-2

SMILES

CCCCCC(=O)OCC=C

InChI Identifier

InChI=1S/C9H16O2/c1-3-5-6-7-9(10)11-8-4-2/h4H,2-3,5-8H2,1H3

InChI Key

RCSBILYQLVXLJG-UHFFFAOYSA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as fatty acid esters. These are carboxylic ester derivatives of a fatty acid.

Kingdom

Organic compounds

Super Class

Lipids and lipid-like molecules

Class

Fatty Acyls

Sub Class

Fatty acid esters

Direct Parent

Fatty acid esters

Alternative Parents

Substituents

Fatty acid ester
Carboxylic acid ester
Monocarboxylic acid or derivatives
Carboxylic acid derivative
Organic oxygen compound
Organic oxide
Hydrocarbon derivative
Organooxygen compound
Carbonyl group
Aliphatic acyclic compound

Molecular Framework

Aliphatic acyclic compounds

External Descriptors

Not Available

Ontology

Sweet

Disposition

Biological location

Cellular substructure

Excreta

Biofluid or Excreta

Urine (HMDB: HMDB0040210)

Route of exposure

Enteral

Ingestion (HMDB: HMDB0040210)

Source

Endogenous

Endogenous (HMDB: HMDB0040210)

Plant

Plant (HMDB: HMDB0040210)

Animal

Animal (HMDB: HMDB0040210)

Exogenous

Food

Food (HMDB: HMDB0040210)

Vegetable

Mushroom

Tuber

Potato (FooDB: FOOD00175)

Fruit

Fruits (FooDB: FOOD00871)

Exogenous (HMDB: HMDB0040210)

Process

Naturally occurring process

Biological process

Chemical reaction

Lipid Peroxidation (HMDB: HMDB0040210)

Biochemical pathway

Metabolic pathway

Fatty Acid Metabolism (HMDB: HMDB0040210)

Lipid metabolism pathway (HMDB: HMDB0040210)

Cellular process

Cell signaling (HMDB: HMDB0040210)

Biochemical process

Lipid transport (HMDB: HMDB0040210)

Role

Biological role

Energy source (HMDB: HMDB0040210)

Industrial application

Manufacturing industry

Material processing agent

Fluid processing agent

Surfactant

Surfactant (HMDB: HMDB0040210)

Physical Properties

State

Not Available

Experimental Molecular Properties

Property	Value	Reference
Melting Point	Not Available	Not Available
Boiling Point	185.00 °C. @ 760.00 mm Hg	The Good Scents Company Information System
Water Solubility	136.1 mg/L @ 25 °C (est)	The Good Scents Company Information System
LogP	3.128 (est)	The Good Scents Company Information System

Experimental Chromatographic Properties

Not Available

Predicted Molecular Properties

Property	Value	Source
Water Solubility	0.4 g/L	ALOGPS
logP	3.02	ALOGPS
logP	2.69	ChemAxon
logS	-2.6	ALOGPS
pKa (Strongest Basic)	-7	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	1	ChemAxon
Hydrogen Donor Count	0	ChemAxon
Polar Surface Area	26.3 Å²	ChemAxon
Rotatable Bond Count	7	ChemAxon
Refractivity	45.01 m³·mol⁻¹	ChemAxon
Polarizability	18.52 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]+	138.255	31661259
DarkChem	[M-H]-	135.176	31661259
DeepCCS	[M+H]+	140.204	30932474
DeepCCS	[M-H]-	137.439	30932474
DeepCCS	[M-2H]-	174.511	30932474
DeepCCS	[M+Na]+	149.499	30932474
AllCCS	[M+H]+	139.6	32859911
AllCCS	[M+H-H2O]+	135.7	32859911
AllCCS	[M+NH4]+	143.3	32859911
AllCCS	[M+Na]+	144.3	32859911
AllCCS	[M-H]-	139.8	32859911
AllCCS	[M+Na-2H]-	141.8	32859911
AllCCS	[M+HCOO]-	144.2	32859911

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
2-Propenyl hexanoate	CCCCCC(=O)OCC=C	1376.4	Standard polar	33892256
2-Propenyl hexanoate	CCCCCC(=O)OCC=C	1045.8	Standard non polar	33892256
2-Propenyl hexanoate	CCCCCC(=O)OCC=C	1105.3	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-Propenyl hexanoate EI-B (Non-derivatized)	splash10-0006-9000000000-149d79e35c1f7b309b58	2017-09-12	HMDB team, MONA, MassBank	View Spectrum
Experimental GC-MS	GC-MS Spectrum - 2-Propenyl hexanoate EI-B (Non-derivatized)	splash10-0006-9000000000-149d79e35c1f7b309b58	2018-05-18	HMDB team, MONA, MassBank	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - 2-Propenyl hexanoate GC-MS (Non-derivatized) - 70eV, Positive	splash10-0596-9200000000-d882e8ac52bec3e47586	2017-09-01	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - 2-Propenyl hexanoate GC-MS (Non-derivatized) - 70eV, Positive	Not Available	2021-10-12	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - 2-Propenyl hexanoate GC-MS (Non-derivatized) - 70eV, Positive	Not Available	2021-10-12	Wishart Lab	View Spectrum
MS	Mass Spectrum (Electron Ionization)	splash10-0007-9000000000-bc1f3eeb24010e423739	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-Propenyl hexanoate 10V, Positive-QTOF	splash10-0a4i-5900000000-324fa45aced7c63e736b	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 2-Propenyl hexanoate 20V, Positive-QTOF	splash10-0a4j-9200000000-d739e4c131c0da9196ba	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 2-Propenyl hexanoate 40V, Positive-QTOF	splash10-052f-9000000000-9b1cf000856114602cda	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 2-Propenyl hexanoate 10V, Negative-QTOF	splash10-0a4j-7900000000-2c258d937145207f61ce	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 2-Propenyl hexanoate 20V, Negative-QTOF	splash10-014j-9600000000-241fe600e52c60c9749b	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 2-Propenyl hexanoate 40V, Negative-QTOF	splash10-05mw-9000000000-224150987e6813dde16a	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 2-Propenyl hexanoate 10V, Positive-QTOF	splash10-0a4m-9200000000-b6a1d810077f0ce23a0c	2021-09-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 2-Propenyl hexanoate 20V, Positive-QTOF	splash10-0596-9000000000-196c2e4ed2bba6825382	2021-09-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 2-Propenyl hexanoate 40V, Positive-QTOF	splash10-0a4l-9000000000-e517694f394d13aba4d9	2021-09-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 2-Propenyl hexanoate 10V, Negative-QTOF	splash10-0002-9000000000-08ab9ac78c60653a60d6	2021-09-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 2-Propenyl hexanoate 20V, Negative-QTOF	splash10-00kb-9300000000-8c41d2bdeb5aab658458	2021-09-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 2-Propenyl hexanoate 40V, Negative-QTOF	splash10-0002-9000000000-7932c97ff8ef70fb2255	2021-09-24	Wishart Lab	View Spectrum

NMR Spectra

Spectrum Type	Description	Deposition Date	Source	View

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+Na]+)	2023-02-04	FELIX lab	View Spectrum

Biological Properties

Cellular Locations

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

FDB019922

KNApSAcK ID

C00053314

Chemspider ID

29006

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

31266

PDB ID

Not Available

ChEBI ID

Not Available

Food Biomarker Ontology

Not Available

VMH ID

Not Available

MarkerDB ID

Not Available

Good Scents ID

rw1000731

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-Propenyl hexanoate (HMDB0040210)

MOL for HMDB0040210 (2-Propenyl hexanoate)

3D MOL for HMDB0040210 (2-Propenyl hexanoate)

3D SDF for HMDB0040210 (2-Propenyl hexanoate)

3D-SDF for HMDB0040210 (2-Propenyl hexanoate)

PDB for HMDB0040210 (2-Propenyl hexanoate)

3D PDB for HMDB0040210 (2-Propenyl hexanoate)

SMILES for HMDB0040210 (2-Propenyl hexanoate)

INCHI for HMDB0040210 (2-Propenyl hexanoate)

Structure for HMDB0040210 (2-Propenyl hexanoate)

3D Structure for HMDB0040210 (2-Propenyl hexanoate)

Predicted Collision Cross Sections

Predicted Kovats Retention Indices

Underivatized

GC-MS Spectra

MS/MS Spectra

NMR Spectra

IR Spectra