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Record Information

Version

5.0

Status

Expected but not Quantified

Creation Date

2012-09-11 21:45:27 UTC

Update Date

2023-02-21 17:25:26 UTC

HMDB ID

HMDB0036598

Secondary Accession Numbers

HMDB36598

Metabolite Identification

Common Name

(E,E)-2,4-Decadienal

Description

(E,E)-2,4-Decadienal belongs to the class of organic compounds known as medium-chain aldehydes. These are an aldehyde with a chain length containing between 6 and 12 carbon atoms. Thus, (e,e)-2,4-decadienal is considered to be a fatty aldehyde (E,E)-2,4-Decadienal is a fat, fatty, and fried tasting compound (E,E)-2,4-Decadienal has been detected, but not quantified in, taco and tortilla chip. This could make (e,e)-2,4-decadienal a potential biomarker for the consumption of these foods. Based on a literature review very few articles have been published on (E,E)-2,4-Decadienal.

Structure

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

COMPND    HMDB0036598
HETATM    1  C1  UNL     1      -3.930   0.279  -0.809  1.00  0.00           C  
HETATM    2  C2  UNL     1      -3.221  -1.013  -0.462  1.00  0.00           C  
HETATM    3  C3  UNL     1      -2.025  -0.648   0.420  1.00  0.00           C  
HETATM    4  C4  UNL     1      -1.086   0.276  -0.311  1.00  0.00           C  
HETATM    5  C5  UNL     1       0.067   0.616   0.622  1.00  0.00           C  
HETATM    6  C6  UNL     1       0.805  -0.594   1.021  1.00  0.00           C  
HETATM    7  C7  UNL     1       2.078  -0.736   0.734  1.00  0.00           C  
HETATM    8  C8  UNL     1       2.828   0.263   0.023  1.00  0.00           C  
HETATM    9  C9  UNL     1       4.139  -0.009  -0.208  1.00  0.00           C  
HETATM   10  C10 UNL     1       4.943   0.963  -0.921  1.00  0.00           C  
HETATM   11  O1  UNL     1       4.454   2.050  -1.329  1.00  0.00           O  
HETATM   12  H1  UNL     1      -3.376   0.866  -1.584  1.00  0.00           H  
HETATM   13  H2  UNL     1      -4.975   0.073  -1.147  1.00  0.00           H  
HETATM   14  H3  UNL     1      -4.014   0.924   0.102  1.00  0.00           H  
HETATM   15  H4  UNL     1      -2.857  -1.519  -1.357  1.00  0.00           H  
HETATM   16  H5  UNL     1      -3.916  -1.609   0.156  1.00  0.00           H  
HETATM   17  H6  UNL     1      -2.354  -0.121   1.338  1.00  0.00           H  
HETATM   18  H7  UNL     1      -1.444  -1.588   0.659  1.00  0.00           H  
HETATM   19  H8  UNL     1      -1.610   1.201  -0.617  1.00  0.00           H  
HETATM   20  H9  UNL     1      -0.692  -0.187  -1.226  1.00  0.00           H  
HETATM   21  H10 UNL     1       0.644   1.406   0.152  1.00  0.00           H  
HETATM   22  H11 UNL     1      -0.376   1.127   1.550  1.00  0.00           H  
HETATM   23  H12 UNL     1       0.288  -1.407   1.585  1.00  0.00           H  
HETATM   24  H13 UNL     1       2.596  -1.664   1.054  1.00  0.00           H  
HETATM   25  H14 UNL     1       2.475   1.206  -0.352  1.00  0.00           H  
HETATM   26  H15 UNL     1       4.584  -0.917   0.122  1.00  0.00           H  
HETATM   27  H16 UNL     1       5.974   0.762  -1.109  1.00  0.00           H  
CONECT    1    2   12   13   14
CONECT    2    3   15   16
CONECT    3    4   17   18
CONECT    4    5   19   20
CONECT    5    6   21   22
CONECT    6    7    7   23
CONECT    7    8   24
CONECT    8    9    9   25
CONECT    9   10   26
CONECT   10   11   11   27
END

View in JSmol View Stereo Labels

Synonyms

Value	Source
(e)-2,(e)-4-Decadienal	HMDB
(e,e)-2,4-Decadecenal	HMDB
(e,e)-2,4-Decadien-1-al	HMDB
(e,e)-2,4-Decanedienal	HMDB
(e,e)-Deca-2,4-dienal	HMDB
2,4-trans,trans-Decadienal	HMDB
2-trans,4-trans-Decadienal	HMDB
2E,4E-Decadienal	HMDB
Deca-2(e),4(e)-dienal	HMDB
FEMA 3135	HMDB
trans-2, trans-4-Decadienal	HMDB

Chemical Formula

C₁₀H₁₆O

Average Molecular Weight

152.2334

Monoisotopic Molecular Weight

152.120115134

IUPAC Name

(2E,4Z)-deca-2,4-dienal

Traditional Name

(2E,4Z)-deca-2,4-dienal

CAS Registry Number

25152-84-5

SMILES

CCCCC\C=C/C=C/C=O

InChI Identifier

InChI=1S/C10H16O/c1-2-3-4-5-6-7-8-9-10-11/h6-10H,2-5H2,1H3/b7-6-,9-8+

InChI Key

JZQKTMZYLHNFPL-NMMTYZSQSA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as medium-chain aldehydes. These are an aldehyde with a chain length containing between 6 and 12 carbon atoms.

Kingdom

Organic compounds

Super Class

Organic oxygen compounds

Class

Organooxygen compounds

Sub Class

Carbonyl compounds

Direct Parent

Medium-chain aldehydes

Alternative Parents

Substituents

Medium-chain aldehyde
Enal
Alpha,beta-unsaturated aldehyde
Organic oxide
Hydrocarbon derivative
Aliphatic acyclic compound

Molecular Framework

Aliphatic acyclic compounds

External Descriptors

Fatty aldehydes (LMFA06000146 )

Ontology

Exogenous (HMDB: HMDB0036598)

Food

Cereal and cereal product

Cereal product

Breakfast cereal (FooDB: FOOD00270)

Flat bread

Tortilla (FooDB: FOOD00709)

Cereals and cereal products (FooDB: FOOD00858)

Vegetable

Cabbage

Root vegetable

Carrot (FooDB: FOOD00245)

Herb and spice

Oilseed crop

Safflower (FooDB: FOOD00042)

Herbs and Spices (FooDB: FOOD00866)

Fruit

Pome

Asian pear (FooDB: FOOD00291)
Pomes (FooDB: FOOD00856)

Citrus

Citrus (FooDB: FOOD00859)

Fruits (FooDB: FOOD00871)

Berry

Evergreen blackberry (FooDB: FOOD00901)
Blackberry (FooDB: FOOD00906)

Snack

Tortilla chip (FooDB: FOOD00721)

Dish

Tex-mex cuisine

Taco (FooDB: FOOD00708)

Pulse

Pulses (FooDB: FOOD00867)

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	279.00 to 280.00 °C. @ 760.00 mm Hg	The Good Scents Company Information System
Water Solubility	0	The Good Scents Company Information System
LogP	3.180 (est)	The Good Scents Company Information System

Experimental Chromatographic Properties

Not Available

Predicted Molecular Properties

Property	Value	Source
Water Solubility	0.038 g/L	ALOGPS
logP	3.81	ALOGPS
logP	3.07	ChemAxon
logS	-3.6	ALOGPS
pKa (Strongest Basic)	-4.1	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	1	ChemAxon
Hydrogen Donor Count	0	ChemAxon
Polar Surface Area	17.07 Å²	ChemAxon
Rotatable Bond Count	6	ChemAxon
Refractivity	50.76 m³·mol⁻¹	ChemAxon
Polarizability	18.76 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]+	141.172	31661259
DarkChem	[M-H]-	137.617	31661259
DeepCCS	[M+H]+	143.929	30932474
DeepCCS	[M-H]-	140.609	30932474
DeepCCS	[M-2H]-	178.159	30932474
DeepCCS	[M+Na]+	153.307	30932474
AllCCS	[M+H]+	137.4	32859911
AllCCS	[M+H-H2O]+	133.3	32859911
AllCCS	[M+NH4]+	141.2	32859911
AllCCS	[M+Na]+	142.3	32859911
AllCCS	[M-H]-	140.9	32859911
AllCCS	[M+Na-2H]-	142.8	32859911
AllCCS	[M+HCOO]-	145.0	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.	7.21 minutes	32390414
Predicted by Siyang on May 30, 2022	19.211 minutes	33406817
Predicted by Siyang using ReTip algorithm on June 8, 2022	4.22 minutes	32390414
Fem_Long = Waters ACQUITY UPLC HSS T3 C18 with Water:MeOH and 0.1% Formic Acid	2323.6 seconds	40023050
Fem_Lipids = Ascentis Express C18 with (60:40 water:ACN):(90:10 IPA:ACN) and 10mM NH4COOH + 0.1% Formic Acid	645.1 seconds	40023050
Life_Old = Waters ACQUITY UPLC BEH C18 with Water:(20:80 acetone:ACN) and 0.1% Formic Acid	260.4 seconds	40023050
Life_New = RP Waters ACQUITY UPLC HSS T3 C18 with Water:(30:70 MeOH:ACN) and 0.1% Formic Acid	486.2 seconds	40023050
RIKEN = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	428.9 seconds	40023050
Eawag_XBridgeC18 = XBridge C18 3.5u 2.1x50 mm with Water:MeOH and 0.1% Formic Acid	833.6 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	673.3 seconds	40023050
HILIC_BDD_2 = Merck SeQuant ZIC-HILIC with ACN(0.1% formic acid):water(16 mM ammonium formate)	146.2 seconds	40023050
UniToyama_Atlantis = RP Waters Atlantis T3 (2.1 x 150 mm, 5 um) with ACN:Water and 0.1% Formic Acid	1676.9 seconds	40023050
BDD_C18 = Hypersil Gold 1.9µm C18 with Water:ACN and 0.1% Formic Acid	557.4 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	1528.4 seconds	40023050
SNU_RIKEN_POS = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	643.4 seconds	40023050
RPMMFDA = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	494.5 seconds	40023050
MTBLS87 = Merck SeQuant ZIC-pHILIC column with ACN:Water and :ammonium carbonate	624.2 seconds	40023050
KI_GIAR_zic_HILIC_pH2_7 = Merck SeQuant ZIC-HILIC with ACN:Water and 0.1% FA	631.8 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	15.2 seconds	40023050

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
(E,E)-2,4-Decadienal	CCCCC\C=C/C=C/C=O	1781.5	Standard polar	33892256
(E,E)-2,4-Decadienal	CCCCC\C=C/C=C/C=O	1264.2	Standard non polar	33892256
(E,E)-2,4-Decadienal	CCCCC\C=C/C=C/C=O	1314.8	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 - (E,E)-2,4-Decadienal GC-MS (Non-derivatized) - 70eV, Positive	splash10-056v-9200000000-a78c81b14766c6330abe	2017-09-01	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - (E,E)-2,4-Decadienal 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 - (E,E)-2,4-Decadienal 10V, Positive-QTOF	splash10-0udi-1900000000-f83a011f91c71a80b934	2016-06-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - (E,E)-2,4-Decadienal 20V, Positive-QTOF	splash10-0zg0-9600000000-a4540601efb8cd103ef3	2016-06-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - (E,E)-2,4-Decadienal 40V, Positive-QTOF	splash10-0k96-9000000000-1faafdc9d775720641d7	2016-06-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - (E,E)-2,4-Decadienal 10V, Negative-QTOF	splash10-0udi-0900000000-628ab06d795fdadde021	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - (E,E)-2,4-Decadienal 20V, Negative-QTOF	splash10-0udi-1900000000-a5c55eb8c770cd27619e	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - (E,E)-2,4-Decadienal 40V, Negative-QTOF	splash10-0006-9400000000-3188737bd53ba9403c58	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - (E,E)-2,4-Decadienal 10V, Negative-QTOF	splash10-0udi-0900000000-b6b99e44690e9b436304	2021-09-23	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - (E,E)-2,4-Decadienal 20V, Negative-QTOF	splash10-014i-3900000000-dafdce0aa6c724aeb7d4	2021-09-23	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - (E,E)-2,4-Decadienal 40V, Negative-QTOF	splash10-014i-9000000000-79f435f03554a2838f08	2021-09-23	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - (E,E)-2,4-Decadienal 10V, Positive-QTOF	splash10-016u-9100000000-ed51f180739bfe5a6410	2021-09-25	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - (E,E)-2,4-Decadienal 20V, Positive-QTOF	splash10-066r-9000000000-f37f6b96cef9ccb76b14	2021-09-25	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - (E,E)-2,4-Decadienal 40V, Positive-QTOF	splash10-015c-9000000000-937a010c214c50e0d98c	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

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

FDB015512

KNApSAcK ID

C00029997

Chemspider ID

4932505

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

(E,E)-2,4-Decadienal

METLIN ID

Not Available

PubChem Compound

6427087

PDB ID

Not Available

ChEBI ID

Not Available

Food Biomarker Ontology

Not Available

VMH ID

Not Available

MarkerDB ID

Not Available

Good Scents ID

rw1028121

References

Synthesis Reference

Not Available

Material Safety Data Sheet (MSDS)

Not Available

General References

(). Yannai, Shmuel. (2004) Dictionary of food compounds with CD-ROM: Additives, flavors, and ingredients. Boca Raton: Chapman & Hall/CRC.. .

Showing metabocard for (E,E)-2,4-Decadienal (HMDB0036598)

MOL for HMDB0036598 ((E,E)-2,4-Decadienal)

3D MOL for HMDB0036598 ((E,E)-2,4-Decadienal)

3D SDF for HMDB0036598 ((E,E)-2,4-Decadienal)

3D-SDF for HMDB0036598 ((E,E)-2,4-Decadienal)

PDB for HMDB0036598 ((E,E)-2,4-Decadienal)

3D PDB for HMDB0036598 ((E,E)-2,4-Decadienal)

SMILES for HMDB0036598 ((E,E)-2,4-Decadienal)

INCHI for HMDB0036598 ((E,E)-2,4-Decadienal)

Structure for HMDB0036598 ((E,E)-2,4-Decadienal)

3D Structure for HMDB0036598 ((E,E)-2,4-Decadienal)

Predicted Collision Cross Sections

Predicted Retention Times

Underivatized

Predicted Kovats Retention Indices

Underivatized

GC-MS Spectra

MS/MS Spectra

IR Spectra