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Record Information

Version

5.0

Status

Expected but not Quantified

Creation Date

2012-09-11 23:33:25 UTC

Update Date

2023-02-21 17:26:26 UTC

HMDB ID

HMDB0038272

Secondary Accession Numbers

HMDB38272

Metabolite Identification

Common Name

trans-2-Hexenyl propanoate

Description

trans-2-Hexenyl propanoate is a member of the class of compounds known as carboxylic acid esters. Carboxylic acid esters 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). trans-2-Hexenyl propanoate is practically insoluble (in water) and an extremely weak basic (essentially neutral) compound (based on its pKa). trans-2-Hexenyl propanoate is used as a food additive (EAFUS: Everything Added to Food in the United States). trans-2-Hexenyl propanoate is a flavouring ingredient and has an apple and fruity taste.

Structure

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

COMPND    HMDB0038272
HETATM    1  C1  UNL     1       3.670  -0.467  -0.814  1.00  0.00           C  
HETATM    2  C2  UNL     1       3.554  -0.133   0.638  1.00  0.00           C  
HETATM    3  C3  UNL     1       2.303  -0.672   1.291  1.00  0.00           C  
HETATM    4  C4  UNL     1       1.049  -0.149   0.721  1.00  0.00           C  
HETATM    5  C5  UNL     1       0.925   0.727  -0.244  1.00  0.00           C  
HETATM    6  C6  UNL     1      -0.399   1.194  -0.757  1.00  0.00           C  
HETATM    7  O1  UNL     1      -1.466   0.596  -0.098  1.00  0.00           O  
HETATM    8  C7  UNL     1      -2.754   0.914  -0.494  1.00  0.00           C  
HETATM    9  O2  UNL     1      -3.022   1.717  -1.422  1.00  0.00           O  
HETATM   10  C8  UNL     1      -3.915   0.284   0.198  1.00  0.00           C  
HETATM   11  C9  UNL     1      -4.093  -1.094  -0.454  1.00  0.00           C  
HETATM   12  H1  UNL     1       2.781  -0.925  -1.249  1.00  0.00           H  
HETATM   13  H2  UNL     1       3.959   0.444  -1.394  1.00  0.00           H  
HETATM   14  H3  UNL     1       4.543  -1.169  -1.006  1.00  0.00           H  
HETATM   15  H4  UNL     1       3.661   0.971   0.824  1.00  0.00           H  
HETATM   16  H5  UNL     1       4.450  -0.578   1.156  1.00  0.00           H  
HETATM   17  H6  UNL     1       2.372  -0.462   2.396  1.00  0.00           H  
HETATM   18  H7  UNL     1       2.378  -1.779   1.236  1.00  0.00           H  
HETATM   19  H8  UNL     1       0.104  -0.530   1.144  1.00  0.00           H  
HETATM   20  H9  UNL     1       1.799   1.143  -0.689  1.00  0.00           H  
HETATM   21  H10 UNL     1      -0.512   2.289  -0.657  1.00  0.00           H  
HETATM   22  H11 UNL     1      -0.442   0.945  -1.833  1.00  0.00           H  
HETATM   23  H12 UNL     1      -3.750   0.208   1.292  1.00  0.00           H  
HETATM   24  H13 UNL     1      -4.835   0.853  -0.008  1.00  0.00           H  
HETATM   25  H14 UNL     1      -3.501  -1.837   0.135  1.00  0.00           H  
HETATM   26  H15 UNL     1      -3.703  -1.086  -1.491  1.00  0.00           H  
HETATM   27  H16 UNL     1      -5.156  -1.403  -0.470  1.00  0.00           H  
CONECT    1    2   12   13   14
CONECT    2    3   15   16
CONECT    3    4   17   18
CONECT    4    5    5   19
CONECT    5    6   20
CONECT    6    7   21   22
CONECT    7    8
CONECT    8    9    9   10
CONECT   10   11   23   24
CONECT   11   25   26   27
END

View in JSmol View Stereo Labels

Synonyms

Value	Source
trans-2-Hexenyl propionate	ChEBI
trans-2-Hexenyl propionic acid	Generator
trans-2-Hexenyl propanoic acid	Generator
(2E)-2-Hexenyl propionate	HMDB
(e)-2-Hexen-1-ol, propanoate	HMDB
(e)-2-Hexenyl propanoate	HMDB
(e)-2-Hexenyl propionate	HMDB
2-Hexenyl propanoate	HMDB
FEMA 3932	HMDB
trans-2-Hexenyl N-propionate	HMDB
trans-2-HEXENYLPROPIONATE	HMDB
(2E)-Hex-2-en-1-yl propanoic acid	HMDB
Hex-trans-2-enyl propionic acid	Generator

Chemical Formula

C₉H₁₆O₂

Average Molecular Weight

156.2221

Monoisotopic Molecular Weight

156.115029756

IUPAC Name

(2E)-hex-2-en-1-yl propanoate

Traditional Name

(2E)-hex-2-en-1-yl propanoate

CAS Registry Number

53398-80-4

SMILES

CCC\C=C\COC(=O)CC

InChI Identifier

InChI=1S/C9H16O2/c1-3-5-6-7-8-11-9(10)4-2/h6-7H,3-5,8H2,1-2H3/b7-6+

InChI Key

LPWKTEHEFDVAQS-VOTSOKGWSA-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

propanoate ester (CHEBI:87682 )

Ontology

Cellular substructure

Membrane (HMDB: HMDB0038272)

Source

Exogenous

Exogenous (HMDB: HMDB0038272)

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	91.00 °C. @ 20.00 mm Hg	The Good Scents Company Information System
Water Solubility	158.9 mg/L @ 25 °C (est)	The Good Scents Company Information System
LogP	3.127 (est)	The Good Scents Company Information System

Experimental Chromatographic Properties

Not Available

Predicted Molecular Properties

Property	Value	Source
Water Solubility	0.66 g/L	ALOGPS
logP	2.83	ALOGPS
logP	2.63	ChemAxon
logS	-2.4	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	6	ChemAxon
Refractivity	46.08 m³·mol⁻¹	ChemAxon
Polarizability	18.8 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]+	138.175	31661259
DarkChem	[M-H]-	134.353	31661259
DeepCCS	[M+H]+	135.279	30932474
DeepCCS	[M-H]-	131.565	30932474
DeepCCS	[M-2H]-	169.049	30932474
DeepCCS	[M+Na]+	144.323	30932474
AllCCS	[M+H]+	139.1	32859911
AllCCS	[M+H-H2O]+	135.2	32859911
AllCCS	[M+NH4]+	142.8	32859911
AllCCS	[M+Na]+	143.9	32859911
AllCCS	[M-H]-	140.1	32859911
AllCCS	[M+Na-2H]-	142.1	32859911
AllCCS	[M+HCOO]-	144.4	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.	6.54 minutes	32390414
Predicted by Siyang on May 30, 2022	16.9049 minutes	33406817
Predicted by Siyang using ReTip algorithm on June 8, 2022	4.48 minutes	32390414
Fem_Long = Waters ACQUITY UPLC HSS T3 C18 with Water:MeOH and 0.1% Formic Acid	2315.6 seconds	40023050
Fem_Lipids = Ascentis Express C18 with (60:40 water:ACN):(90:10 IPA:ACN) and 10mM NH4COOH + 0.1% Formic Acid	547.9 seconds	40023050
Life_Old = Waters ACQUITY UPLC BEH C18 with Water:(20:80 acetone:ACN) and 0.1% Formic Acid	213.9 seconds	40023050
Life_New = RP Waters ACQUITY UPLC HSS T3 C18 with Water:(30:70 MeOH:ACN) and 0.1% Formic Acid	387.8 seconds	40023050
RIKEN = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	319.6 seconds	40023050
Eawag_XBridgeC18 = XBridge C18 3.5u 2.1x50 mm with Water:MeOH and 0.1% Formic Acid	700.7 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	689.1 seconds	40023050
HILIC_BDD_2 = Merck SeQuant ZIC-HILIC with ACN(0.1% formic acid):water(16 mM ammonium formate)	122.9 seconds	40023050
UniToyama_Atlantis = RP Waters Atlantis T3 (2.1 x 150 mm, 5 um) with ACN:Water and 0.1% Formic Acid	1421.8 seconds	40023050
BDD_C18 = Hypersil Gold 1.9µm C18 with Water:ACN and 0.1% Formic Acid	514.8 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	1465.3 seconds	40023050
SNU_RIKEN_POS = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	495.8 seconds	40023050
RPMMFDA = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	400.2 seconds	40023050
MTBLS87 = Merck SeQuant ZIC-pHILIC column with ACN:Water and :ammonium carbonate	539.6 seconds	40023050
KI_GIAR_zic_HILIC_pH2_7 = Merck SeQuant ZIC-HILIC with ACN:Water and 0.1% FA	534.0 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	24.9 seconds	40023050

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
trans-2-Hexenyl propanoate	CCC\C=C\COC(=O)CC	1416.8	Standard polar	33892256
trans-2-Hexenyl propanoate	CCC\C=C\COC(=O)CC	1064.1	Standard non polar	33892256
trans-2-Hexenyl propanoate	CCC\C=C\COC(=O)CC	1140.2	Semi standard non polar	33892256

Spectra

GC-MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Experimental GC-MS	GC-MS Spectrum - trans-2-Hexenyl propanoate EI-B (Non-derivatized)	splash10-0a4i-9000000000-fd16154f2b66da8adddd	2017-09-12	HMDB team, MONA, MassBank	View Spectrum
Experimental GC-MS	GC-MS Spectrum - trans-2-Hexenyl propanoate EI-B (Non-derivatized)	splash10-0a4i-9000000000-fd16154f2b66da8adddd	2018-05-18	HMDB team, MONA, MassBank	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - trans-2-Hexenyl propanoate GC-MS (Non-derivatized) - 70eV, Positive	splash10-0a6r-9000000000-3477ca5402f0cbe226d0	2017-09-01	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - trans-2-Hexenyl propanoate 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 - trans-2-Hexenyl propanoate 10V, Positive-QTOF	splash10-0a4i-9700000000-70ce1490d65b0a8d40fd	2016-08-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - trans-2-Hexenyl propanoate 20V, Positive-QTOF	splash10-001i-9100000000-ab0a781c5c7a1f13705a	2016-08-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - trans-2-Hexenyl propanoate 40V, Positive-QTOF	splash10-0a4l-9000000000-8f2b6114937867a2b5ac	2016-08-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - trans-2-Hexenyl propanoate 10V, Negative-QTOF	splash10-0a4i-9500000000-6d6c5fa7258c9b026646	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - trans-2-Hexenyl propanoate 20V, Negative-QTOF	splash10-05fr-9100000000-bee9c2426d6f3b005257	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - trans-2-Hexenyl propanoate 40V, Negative-QTOF	splash10-0a4i-9000000000-8fb2831ee65667911ce8	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - trans-2-Hexenyl propanoate 10V, Positive-QTOF	splash10-0a5c-9000000000-777b0b0830a7a4e1d85c	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - trans-2-Hexenyl propanoate 20V, Positive-QTOF	splash10-0a4i-9000000000-ab88b56f1b106b923732	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - trans-2-Hexenyl propanoate 40V, Positive-QTOF	splash10-0a4i-9000000000-f5a823d0ae876894caa7	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - trans-2-Hexenyl propanoate 10V, Negative-QTOF	splash10-00e9-9100000000-6eaf38670cfa50faff77	2021-09-23	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - trans-2-Hexenyl propanoate 20V, Negative-QTOF	splash10-00di-9000000000-14c2d686f44a5d5e1ebc	2021-09-23	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - trans-2-Hexenyl propanoate 40V, Negative-QTOF	splash10-0a4i-9000000000-b0f239ba5d126f68f9f0	2021-09-23	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

FDB004508

KNApSAcK ID

Not Available

Chemspider ID

4509343

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

5352463

PDB ID

Not Available

ChEBI ID

87682

Food Biomarker Ontology

Not Available

VMH ID

Not Available

MarkerDB ID

Not Available

Good Scents ID

rw1026831

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 trans-2-Hexenyl propanoate (HMDB0038272)

MOL for HMDB0038272 (trans-2-Hexenyl propanoate)

3D MOL for HMDB0038272 (trans-2-Hexenyl propanoate)

3D SDF for HMDB0038272 (trans-2-Hexenyl propanoate)

3D-SDF for HMDB0038272 (trans-2-Hexenyl propanoate)

PDB for HMDB0038272 (trans-2-Hexenyl propanoate)

3D PDB for HMDB0038272 (trans-2-Hexenyl propanoate)

SMILES for HMDB0038272 (trans-2-Hexenyl propanoate)

INCHI for HMDB0038272 (trans-2-Hexenyl propanoate)

Structure for HMDB0038272 (trans-2-Hexenyl propanoate)

3D Structure for HMDB0038272 (trans-2-Hexenyl propanoate)

Predicted Collision Cross Sections

Predicted Retention Times

Underivatized

Predicted Kovats Retention Indices

Underivatized

GC-MS Spectra

MS/MS Spectra

IR Spectra