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Record Information

Version

5.0

Status

Expected but not Quantified

Creation Date

2012-09-11 17:49:07 UTC

Update Date

2023-02-21 17:21:53 UTC

HMDB ID

HMDB0032313

Secondary Accession Numbers

HMDB32313

Metabolite Identification

Common Name

2,4-Hexadienyl isobutyrate

Description

2,4-Hexadienyl isobutyrate, also known as sorbyl isobutyrate, belongs to the class of organic compounds known as carboxylic acid esters. These are carboxylic acid derivatives in which the carbon atom from the carbonyl group is attached to an alkyl or an aryl moiety through an oxygen atom (forming an ester group). Based on a literature review very few articles have been published on 2,4-Hexadienyl isobutyrate.

Structure

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

HEADER    PROTEIN                                 06-MAY-13   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   06-MAY-13         0                                  
HETATM    1  C   UNK     0      -8.002   0.000   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       4.001   0.770   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       2.667  -1.540   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      -6.668   0.770   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      -5.335   0.000   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0      -4.001   0.770   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0      -2.667   0.000   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0      -1.334   0.770   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       2.667   0.000   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       1.334   0.770   0.000  0.00  0.00           C+0
HETATM   11  O   UNK     0       1.334   2.310   0.000  0.00  0.00           O+0
HETATM   12  O   UNK     0       0.000   0.000   0.000  0.00  0.00           O+0
CONECT    1    4                                                            
CONECT    2    9                                                            
CONECT    3    9                                                            
CONECT    4    1    5                                                       
CONECT    5    4    6                                                       
CONECT    6    5    7                                                       
CONECT    7    6    8                                                       
CONECT    8    7   12                                                       
CONECT    9    2    3   10                                                  
CONECT   10    9   11   12                                                  
CONECT   11   10                                                            
CONECT   12    8   10                                                       
MASTER        0    0    0    0    0    0    0    0   12    0   22    0
END

COMPND    HMDB0032313
HETATM    1  C1  UNL     1       3.325   4.066   2.794  1.00  0.00           C  
HETATM    2  C2  UNL     1       2.055   3.417   2.375  1.00  0.00           C  
HETATM    3  C3  UNL     1       2.030   2.141   2.066  1.00  0.00           C  
HETATM    4  C4  UNL     1       0.797   1.479   1.651  1.00  0.00           C  
HETATM    5  C5  UNL     1       0.741   0.199   1.334  1.00  0.00           C  
HETATM    6  C6  UNL     1      -0.467  -0.516   0.913  1.00  0.00           C  
HETATM    7  O1  UNL     1      -0.358  -1.079  -0.379  1.00  0.00           O  
HETATM    8  C7  UNL     1      -1.442  -1.787  -0.897  1.00  0.00           C  
HETATM    9  O2  UNL     1      -2.460  -1.876  -0.164  1.00  0.00           O  
HETATM   10  C8  UNL     1      -1.425  -2.411  -2.235  1.00  0.00           C  
HETATM   11  C9  UNL     1      -1.203  -1.416  -3.339  1.00  0.00           C  
HETATM   12  C10 UNL     1      -2.770  -3.062  -2.467  1.00  0.00           C  
HETATM   13  H1  UNL     1       3.153   5.054   3.248  1.00  0.00           H  
HETATM   14  H2  UNL     1       4.046   4.180   1.971  1.00  0.00           H  
HETATM   15  H3  UNL     1       3.801   3.415   3.575  1.00  0.00           H  
HETATM   16  H4  UNL     1       1.161   4.007   2.330  1.00  0.00           H  
HETATM   17  H5  UNL     1       2.967   1.603   2.132  1.00  0.00           H  
HETATM   18  H6  UNL     1      -0.119   2.049   1.597  1.00  0.00           H  
HETATM   19  H7  UNL     1       1.664  -0.362   1.392  1.00  0.00           H  
HETATM   20  H8  UNL     1      -1.373   0.132   0.893  1.00  0.00           H  
HETATM   21  H9  UNL     1      -0.678  -1.296   1.682  1.00  0.00           H  
HETATM   22  H10 UNL     1      -0.657  -3.230  -2.284  1.00  0.00           H  
HETATM   23  H11 UNL     1      -1.630  -0.437  -2.994  1.00  0.00           H  
HETATM   24  H12 UNL     1      -0.129  -1.222  -3.533  1.00  0.00           H  
HETATM   25  H13 UNL     1      -1.737  -1.773  -4.236  1.00  0.00           H  
HETATM   26  H14 UNL     1      -3.012  -3.175  -3.539  1.00  0.00           H  
HETATM   27  H15 UNL     1      -3.547  -2.493  -1.907  1.00  0.00           H  
HETATM   28  H16 UNL     1      -2.730  -4.065  -1.977  1.00  0.00           H  
CONECT    1    2   13   14   15
CONECT    2    3    3   16
CONECT    3    4   17
CONECT    4    5    5   18
CONECT    5    6   19
CONECT    6    7   20   21
CONECT    7    8
CONECT    8    9    9   10
CONECT   10   11   12   22
CONECT   11   23   24   25
CONECT   12   26   27   28
END

View in JSmol View Stereo Labels

Synonyms

Value	Source
2,4-Hexadienyl isobutyric acid	Generator
2,4-Hexadienyl 2-methylpropanoate	HMDB
2,4-HEXADIENYLISOBUTYRATE	HMDB
2-Methylpropanoic acid 2,4-hexadienyl ester	HMDB
3,5-Hexadienyl isobutyrate	HMDB
Hexa-2,4-dienyl isobutyrate	HMDB
Isobutyric acid, 2,4-hexadienyl ester	HMDB
Isobutyric acid, 2,4-hexadienyl ester (8ci)	HMDB
Propanoic acid, 2-methyl-, 2,4-hexadien-1-yl ester	HMDB
Propanoic acid, 2-methyl-, 2,4-hexadienyl ester	HMDB
Sorbyl isobutyrate	HMDB
(2E,4E)-Hexa-2,4-dien-1-yl 2-methylpropanoic acid	HMDB

Chemical Formula

C₁₀H₁₆O₂

Average Molecular Weight

168.2328

Monoisotopic Molecular Weight

168.115029756

IUPAC Name

(2E,4E)-hexa-2,4-dien-1-yl 2-methylpropanoate

Traditional Name

(2E,4E)-hexa-2,4-dien-1-yl 2-methylpropanoate

CAS Registry Number

16491-24-0

SMILES

C\C=C\C=C\COC(=O)C(C)C

InChI Identifier

InChI=1S/C10H16O2/c1-4-5-6-7-8-12-10(11)9(2)3/h4-7,9H,8H2,1-3H3/b5-4+,7-6+

InChI Key

CVYBRMSQMLJGOI-YTXTXJHMSA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as carboxylic acid esters. These are carboxylic acid derivatives in which the carbon atom from the carbonyl group is attached to an alkyl or an aryl moiety through an oxygen atom (forming an ester group).

Kingdom

Organic compounds

Super Class

Organic acids and derivatives

Class

Carboxylic acids and derivatives

Sub Class

Carboxylic acid derivatives

Direct Parent

Carboxylic acid esters

Alternative Parents

Substituents

Carboxylic acid ester
Monocarboxylic acid or derivatives
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

Membrane (HMDB: HMDB0032313)
Cell membrane (HMDB: HMDB0032313)

Source

Endogenous

Endogenous (HMDB: HMDB0032313)

Exogenous

Food

Food (HMDB: HMDB0032313)

Exogenous (HMDB: HMDB0032313)

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	0.34 g/L	ALOGPS
logP	3.03	ALOGPS
logP	2.81	ChemAxon
logS	-2.7	ALOGPS
pKa (Strongest Basic)	-7.1	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	51.77 m³·mol⁻¹	ChemAxon
Polarizability	20.29 Å³	ChemAxon
Number of Rings	0	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	Yes	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]+	143.493	31661259
DarkChem	[M-H]-	138.733	31661259
DeepCCS	[M+H]+	142.073	30932474
DeepCCS	[M-H]-	139.638	30932474
DeepCCS	[M-2H]-	175.197	30932474
DeepCCS	[M+Na]+	150.157	30932474
AllCCS	[M+H]+	139.5	32859911
AllCCS	[M+H-H2O]+	135.6	32859911
AllCCS	[M+NH4]+	143.2	32859911
AllCCS	[M+Na]+	144.2	32859911
AllCCS	[M-H]-	140.6	32859911
AllCCS	[M+Na-2H]-	142.3	32859911
AllCCS	[M+HCOO]-	144.2	32859911

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
2,4-Hexadienyl isobutyrate	C\C=C\C=C\COC(=O)C(C)C	1682.5	Standard polar	33892256
2,4-Hexadienyl isobutyrate	C\C=C\C=C\COC(=O)C(C)C	1205.9	Standard non polar	33892256
2,4-Hexadienyl isobutyrate	C\C=C\C=C\COC(=O)C(C)C	1245.4	Semi standard non polar	33892256

Spectra

GC-MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Predicted GC-MS	Predicted GC-MS Spectrum - 2,4-Hexadienyl isobutyrate GC-MS (Non-derivatized) - 70eV, Positive	splash10-0089-9000000000-8a5f4f5d7be9474d22b0	2017-09-01	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - 2,4-Hexadienyl isobutyrate 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 - 2,4-Hexadienyl isobutyrate 10V, Positive-QTOF	splash10-0159-9700000000-bad23d1cf73d549d88d4	2017-09-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 2,4-Hexadienyl isobutyrate 20V, Positive-QTOF	splash10-001i-9000000000-dcc63d0c7738abf31ea4	2017-09-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 2,4-Hexadienyl isobutyrate 40V, Positive-QTOF	splash10-0596-9000000000-922b9c1c9911f8a7e2d2	2017-09-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 2,4-Hexadienyl isobutyrate 10V, Negative-QTOF	splash10-014i-6900000000-4e04590ddb4a06af11b5	2017-09-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 2,4-Hexadienyl isobutyrate 20V, Negative-QTOF	splash10-000i-9100000000-cf0e0dfd02e1fb441bb7	2017-09-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 2,4-Hexadienyl isobutyrate 40V, Negative-QTOF	splash10-000i-9000000000-c983f92945b34f509b8e	2017-09-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 2,4-Hexadienyl isobutyrate 10V, Positive-QTOF	splash10-001i-9000000000-d5fd591eb0ce042ce219	2021-09-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 2,4-Hexadienyl isobutyrate 20V, Positive-QTOF	splash10-00gu-9000000000-7a665c1c2816d0655a17	2021-09-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 2,4-Hexadienyl isobutyrate 40V, Positive-QTOF	splash10-00nf-9000000000-b3e021ae8d252a0338a7	2021-09-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 2,4-Hexadienyl isobutyrate 10V, Negative-QTOF	splash10-00kk-9300000000-0abf03c6cc289c3be345	2021-09-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 2,4-Hexadienyl isobutyrate 20V, Negative-QTOF	splash10-002r-9000000000-6401f1090a2d7c88bf00	2021-09-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 2,4-Hexadienyl isobutyrate 40V, Negative-QTOF	splash10-000i-9000000000-420c9a3f2a3ca08b6503	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+Na]+)	2023-02-04	FELIX lab	View Spectrum

Biological Properties

Cellular Locations

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

FDB009561

KNApSAcK ID

Not Available

Chemspider ID

4769365

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

5978897

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

(). EAFUS: Everything Added to Food in the United States.. .

Showing metabocard for 2,4-Hexadienyl isobutyrate (HMDB0032313)

MOL for HMDB0032313 (2,4-Hexadienyl isobutyrate)

3D MOL for HMDB0032313 (2,4-Hexadienyl isobutyrate)

3D SDF for HMDB0032313 (2,4-Hexadienyl isobutyrate)

3D-SDF for HMDB0032313 (2,4-Hexadienyl isobutyrate)

PDB for HMDB0032313 (2,4-Hexadienyl isobutyrate)

3D PDB for HMDB0032313 (2,4-Hexadienyl isobutyrate)

SMILES for HMDB0032313 (2,4-Hexadienyl isobutyrate)

INCHI for HMDB0032313 (2,4-Hexadienyl isobutyrate)

Structure for HMDB0032313 (2,4-Hexadienyl isobutyrate)

3D Structure for HMDB0032313 (2,4-Hexadienyl isobutyrate)

Predicted Collision Cross Sections

Predicted Kovats Retention Indices

Underivatized

GC-MS Spectra

MS/MS Spectra

IR Spectra