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Record Information

Version

5.0

Status

Expected but not Quantified

Creation Date

2012-09-11 21:17:00 UTC

Update Date

2023-02-21 17:25:17 UTC

HMDB ID

HMDB0036227

Secondary Accession Numbers

HMDB36227

Metabolite Identification

Common Name

2-Propenyl 2,4-hexadienoate

Description

2-Propenyl 2,4-hexadienoate belongs to the class of organic compounds known as fatty acid esters. These are carboxylic ester derivatives of a fatty acid. Based on a literature review a small amount of articles have been published on 2-Propenyl 2,4-hexadienoate.

Structure

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

View in JSmol View Stereo Labels

Synonyms

Value	Source
2-Propenyl 2,4-hexadienoic acid	Generator
(e,e)-2-Propenyl 2,4-hexadienoate	HMDB
2,4-Hexadienoic acid, 2-propenyl ester	HMDB
2-Propen-1-yl ester(2E,4E)-2,4-hexadienoic acid	HMDB
2-Propenyl ester(2E,4E)-2,4-hexadienoic acid	HMDB
2-Propenyl ester(e,e)-2,4-hexadienoic acid	HMDB
Allyl (2E,4E)-2,4-hexadienoate	HMDB
Allyl 2,4-hexadienoate	HMDB
Allyl hexa-2,4-dienoate	HMDB
Allyl hexadienoate	HMDB
Allyl sorbate	HMDB
Sorbic acid, allyl ester	HMDB
trans,trans-2-Propenyl 2,4-hexadienoate	HMDB

Chemical Formula

C₉H₁₂O₂

Average Molecular Weight

152.1904

Monoisotopic Molecular Weight

152.083729628

IUPAC Name

prop-2-en-1-yl (2E,4E)-hexa-2,4-dienoate

Traditional Name

prop-2-en-1-yl (2E,4E)-hexa-2,4-dienoate

CAS Registry Number

7493-75-6

SMILES

C\C=C\C=C\C(=O)OCC=C

InChI Identifier

InChI=1S/C9H12O2/c1-3-5-6-7-9(10)11-8-4-2/h3-7H,2,8H2,1H3/b5-3+,7-6+

InChI Key

CVNZYQJBZIJLCL-TWTPFVCWSA-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
Alpha,beta-unsaturated carboxylic ester
Enoate 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

Cellular substructure

Excreta

Biofluid or Excreta

Urine (HMDB: HMDB0036227)

Route of exposure

Enteral

Ingestion (HMDB: HMDB0036227)

Source

Endogenous

Endogenous (HMDB: HMDB0036227)

Animal

Animal (HMDB: HMDB0036227)

Exogenous

Food

Food (HMDB: HMDB0036227)

Exogenous (HMDB: HMDB0036227)

Process

Naturally occurring process

Biological process

Chemical reaction

Lipid Peroxidation (HMDB: HMDB0036227)

Biochemical pathway

Metabolic pathway

Fatty Acid Metabolism (HMDB: HMDB0036227)

Lipid metabolism pathway (HMDB: HMDB0036227)

Cellular process

Cell signaling (HMDB: HMDB0036227)

Biochemical process

Lipid transport (HMDB: HMDB0036227)

Role

Biological role

Energy source (HMDB: HMDB0036227)

Industrial application

Manufacturing industry

Material processing agent

Fluid processing agent

Surfactant

Surfactant (HMDB: HMDB0036227)

Food and nutrition

Food additive

Flavoring agent

Flavoring Agent (HMDB: HMDB0036227)

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	0.3 g/L	ALOGPS
logP	2.55	ALOGPS
logP	2.56	ChemAxon
logS	-2.7	ALOGPS
pKa (Strongest Basic)	-6.8	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	5	ChemAxon
Refractivity	47.22 m³·mol⁻¹	ChemAxon
Polarizability	17.03 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]+	136.504	31661259
DarkChem	[M-H]-	134.47	31661259
DeepCCS	[M+H]+	135.52	30932474
DeepCCS	[M-H]-	132.971	30932474
DeepCCS	[M-2H]-	168.994	30932474
DeepCCS	[M+Na]+	144.254	30932474
AllCCS	[M+H]+	135.4	32859911
AllCCS	[M+H-H2O]+	131.3	32859911
AllCCS	[M+NH4]+	139.2	32859911
AllCCS	[M+Na]+	140.3	32859911
AllCCS	[M-H]-	134.2	32859911
AllCCS	[M+Na-2H]-	136.0	32859911
AllCCS	[M+HCOO]-	138.1	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.	5.91 minutes	32390414
Predicted by Siyang on May 30, 2022	14.5308 minutes	33406817
Predicted by Siyang using ReTip algorithm on June 8, 2022	4.4 minutes	32390414
Fem_Long = Waters ACQUITY UPLC HSS T3 C18 with Water:MeOH and 0.1% Formic Acid	2107.6 seconds	40023050
Fem_Lipids = Ascentis Express C18 with (60:40 water:ACN):(90:10 IPA:ACN) and 10mM NH4COOH + 0.1% Formic Acid	442.5 seconds	40023050
Life_Old = Waters ACQUITY UPLC BEH C18 with Water:(20:80 acetone:ACN) and 0.1% Formic Acid	169.3 seconds	40023050
Life_New = RP Waters ACQUITY UPLC HSS T3 C18 with Water:(30:70 MeOH:ACN) and 0.1% Formic Acid	323.9 seconds	40023050
RIKEN = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	176.2 seconds	40023050
Eawag_XBridgeC18 = XBridge C18 3.5u 2.1x50 mm with Water:MeOH and 0.1% Formic Acid	523.5 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	533.0 seconds	40023050
HILIC_BDD_2 = Merck SeQuant ZIC-HILIC with ACN(0.1% formic acid):water(16 mM ammonium formate)	106.7 seconds	40023050
UniToyama_Atlantis = RP Waters Atlantis T3 (2.1 x 150 mm, 5 um) with ACN:Water and 0.1% Formic Acid	1290.6 seconds	40023050
BDD_C18 = Hypersil Gold 1.9µm C18 with Water:ACN and 0.1% Formic Acid	465.6 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	1187.5 seconds	40023050
SNU_RIKEN_POS = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	413.3 seconds	40023050
RPMMFDA = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	375.1 seconds	40023050
MTBLS87 = Merck SeQuant ZIC-pHILIC column with ACN:Water and :ammonium carbonate	419.9 seconds	40023050
KI_GIAR_zic_HILIC_pH2_7 = Merck SeQuant ZIC-HILIC with ACN:Water and 0.1% FA	466.6 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	48.2 seconds	40023050

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
2-Propenyl 2,4-hexadienoate	C\C=C\C=C\C(=O)OCC=C	1798.8	Standard polar	33892256
2-Propenyl 2,4-hexadienoate	C\C=C\C=C\C(=O)OCC=C	1147.7	Standard non polar	33892256
2-Propenyl 2,4-hexadienoate	C\C=C\C=C\C(=O)OCC=C	1210.1	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 2,4-hexadienoate EI-B (Non-derivatized)	splash10-014v-9100000000-e91fdbb9ce14515b74d7	2017-09-12	HMDB team, MONA, MassBank	View Spectrum
Experimental GC-MS	GC-MS Spectrum - 2-Propenyl 2,4-hexadienoate EI-B (Non-derivatized)	splash10-014v-9100000000-e91fdbb9ce14515b74d7	2018-05-18	HMDB team, MONA, MassBank	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - 2-Propenyl 2,4-hexadienoate GC-MS (Non-derivatized) - 70eV, Positive	splash10-00kb-9200000000-3a1420d3fcf020594607	2017-09-01	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - 2-Propenyl 2,4-hexadienoate GC-MS (Non-derivatized) - 70eV, Positive	Not Available	2021-10-12	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - 2-Propenyl 2,4-hexadienoate 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 - 2-Propenyl 2,4-hexadienoate 10V, Positive-QTOF	splash10-0udi-6900000000-212f20faaa58923dfb80	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 2-Propenyl 2,4-hexadienoate 20V, Positive-QTOF	splash10-0udi-9100000000-279fee351c0ab2c6e55a	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 2-Propenyl 2,4-hexadienoate 40V, Positive-QTOF	splash10-0udi-9000000000-f8695b49ba901da83101	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 2-Propenyl 2,4-hexadienoate 10V, Negative-QTOF	splash10-0udl-6900000000-b305cd28e2cad8f95131	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 2-Propenyl 2,4-hexadienoate 20V, Negative-QTOF	splash10-03dl-9700000000-15d8c78892f3d5cb9ca7	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 2-Propenyl 2,4-hexadienoate 40V, Negative-QTOF	splash10-0006-9100000000-96445b3d1a1223480538	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 2-Propenyl 2,4-hexadienoate 10V, Negative-QTOF	splash10-03dl-9800000000-7816a6b78056bcfc07de	2021-09-21	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 2-Propenyl 2,4-hexadienoate 20V, Negative-QTOF	splash10-0006-9200000000-3db3e00bdc1ddef9a75c	2021-09-21	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 2-Propenyl 2,4-hexadienoate 40V, Negative-QTOF	splash10-02t9-9000000000-4a35d11992494d5c281c	2021-09-21	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 2-Propenyl 2,4-hexadienoate 10V, Positive-QTOF	splash10-07bb-9300000000-f6d066cc883f48e4d09e	2021-09-25	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 2-Propenyl 2,4-hexadienoate 20V, Positive-QTOF	splash10-014l-9000000000-671a05757e8db60558d1	2021-09-25	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 2-Propenyl 2,4-hexadienoate 40V, Positive-QTOF	splash10-016r-9000000000-62f0c5fb0647b212a086	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+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

FDB015085

KNApSAcK ID

Not Available

Chemspider ID

4940525

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

6435833

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

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 2,4-hexadienoate (HMDB0036227)

MOL for HMDB0036227 (2-Propenyl 2,4-hexadienoate)

3D MOL for HMDB0036227 (2-Propenyl 2,4-hexadienoate)

3D SDF for HMDB0036227 (2-Propenyl 2,4-hexadienoate)

3D-SDF for HMDB0036227 (2-Propenyl 2,4-hexadienoate)

PDB for HMDB0036227 (2-Propenyl 2,4-hexadienoate)

3D PDB for HMDB0036227 (2-Propenyl 2,4-hexadienoate)

SMILES for HMDB0036227 (2-Propenyl 2,4-hexadienoate)

INCHI for HMDB0036227 (2-Propenyl 2,4-hexadienoate)

Structure for HMDB0036227 (2-Propenyl 2,4-hexadienoate)

3D Structure for HMDB0036227 (2-Propenyl 2,4-hexadienoate)

Predicted Collision Cross Sections

Predicted Retention Times

Underivatized

Predicted Kovats Retention Indices

Underivatized

GC-MS Spectra

MS/MS Spectra

IR Spectra