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Record Information

Version

5.0

Status

Expected but not Quantified

Creation Date

2012-09-12 01:05:07 UTC

Update Date

2023-02-21 17:27:00 UTC

HMDB ID

HMDB0039581

Secondary Accession Numbers

HMDB39581

Metabolite Identification

Common Name

Ethyl crotonate

Description

Ethyl crotonate is found in alcoholic beverages. Ethyl crotonate is a component of strawberry aroma, guava fruit and peel (Psidium guajava), pineapple, yellow passion fruit and other fruits. Also present in white wine and mussels. Ethyl crotonate is a flavouring ingredient.

Structure

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

View in JSmol View NMR Assignments View Stereo Labels

Synonyms

Value	Source
cis-Ethyl crotonate	ChEBI
cis-Ethyl crotonic acid	Generator
Ethyl crotonic acid	Generator
(e)-2-Butenoic acid ethyl ester	HMDB
(e)-alpha-Crotonic acid ethyl ester	HMDB
(e)-CH3CH=chcooc2h5	HMDB
(e)-Ethyl 2-butenoate	HMDB
2-Butenoic acid, ethyl ester, (e)- (9ci)	HMDB
alpha -Crotonic acid ethyl ester	HMDB
Crotonic acid ethyl ester	HMDB
Crotonic acid, ethyl ester	HMDB
Ethyl (2E)-2-butenoate	HMDB
Ethyl (2E)-but-2-enoate	HMDB
Ethyl (e)-2-butenoate	HMDB
Ethyl (e)-crotonate	HMDB
Ethyl crotonate (e)	HMDB
Ethyl ester(2E)-2-butenoic acid	HMDB
Ethyl ester(e)-2-butenoic acid	HMDB
Ethyl ester(e)-crotonic acid	HMDB
Ethyl trans-crotonate	HMDB
Ethylester kyseliny krotonove	HMDB
FEMA 3486	HMDB
trans-2-Butenoic acid ethyl ester	HMDB

Chemical Formula

C₆H₁₀O₂

Average Molecular Weight

114.1424

Monoisotopic Molecular Weight

114.068079564

IUPAC Name

ethyl (2Z)-but-2-enoate

Traditional Name

ethyl (2Z)-but-2-enoate

CAS Registry Number

623-70-1

SMILES

CCOC(=O)\C=C/C

InChI Identifier

InChI=1S/C6H10O2/c1-3-5-6(7)8-4-2/h3,5H,4H2,1-2H3/b5-3-

InChI Key

ZFDIRQKJPRINOQ-HYXAFXHYSA-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

but-2-enoate ester (CHEBI:87334 )

Ontology

Cellular substructure

Excreta

Biofluid or Excreta

Urine (HMDB: HMDB0039581)

Route of exposure

Enteral

Ingestion (HMDB: HMDB0039581)

Source

Endogenous

Endogenous (HMDB: HMDB0039581)

Plant

Plant (HMDB: HMDB0039581)

Animal

Animal (HMDB: HMDB0039581)

Exogenous

Food

Food (HMDB: HMDB0039581)

Fruit

Tropical fruit

Prickly pear (FooDB: FOOD00440)

Pome

Asian pear (FooDB: FOOD00291)

Fruits (FooDB: FOOD00871)

Beverage

Alcoholic beverage

Alcoholic beverages (FooDB: FOOD00854)

Aquatic origin

Mollusk

Mollusks (FooDB: FOOD00868)

Exogenous (HMDB: HMDB0039581)

Process

Naturally occurring process

Biological process

Chemical reaction

Lipid Peroxidation (HMDB: HMDB0039581)

Biochemical pathway

Metabolic pathway

Fatty Acid Metabolism (HMDB: HMDB0039581)

Lipid metabolism pathway (HMDB: HMDB0039581)

Cellular process

Cell signaling (HMDB: HMDB0039581)

Biochemical process

Lipid transport (HMDB: HMDB0039581)

Role

Biological role

Energy source (HMDB: HMDB0039581)

Industrial application

Manufacturing industry

Material processing agent

Fluid processing agent

Surfactant

Surfactant (HMDB: HMDB0039581)

Food and nutrition

Food additive

Flavoring agent

Flavoring Agent (HMDB: HMDB0039581)

Physical Properties

State

Not Available

Experimental Molecular Properties

Property	Value	Reference
Melting Point	Not Available	Not Available
Boiling Point	132.00 to 134.00 °C. @ 760.00 mm Hg	The Good Scents Company Information System
Water Solubility	4259 mg/L @ 25 °C (est)	The Good Scents Company Information System
LogP	1.848 (est)	The Good Scents Company Information System

Experimental Chromatographic Properties

Not Available

Predicted Molecular Properties

Property	Value	Source
Water Solubility	9.25 g/L	ALOGPS
logP	1.7	ALOGPS
logP	1.66	ChemAxon
logS	-1.1	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	3	ChemAxon
Refractivity	32.48 m³·mol⁻¹	ChemAxon
Polarizability	12.35 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]+	124.132	31661259
DarkChem	[M-H]-	119.107	31661259
DeepCCS	[M+H]+	126.844	30932474
DeepCCS	[M-H]-	124.843	30932474
DeepCCS	[M-2H]-	161.066	30932474
DeepCCS	[M+Na]+	135.756	30932474
AllCCS	[M+H]+	127.4	32859911
AllCCS	[M+H-H2O]+	123.1	32859911
AllCCS	[M+NH4]+	131.4	32859911
AllCCS	[M+Na]+	132.6	32859911
AllCCS	[M-H]-	127.3	32859911
AllCCS	[M+Na-2H]-	130.6	32859911
AllCCS	[M+HCOO]-	134.3	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.	4.32 minutes	32390414
Predicted by Siyang on May 30, 2022	12.0892 minutes	33406817
Predicted by Siyang using ReTip algorithm on June 8, 2022	4.15 minutes	32390414
Fem_Long = Waters ACQUITY UPLC HSS T3 C18 with Water:MeOH and 0.1% Formic Acid	1627.4 seconds	40023050
Fem_Lipids = Ascentis Express C18 with (60:40 water:ACN):(90:10 IPA:ACN) and 10mM NH4COOH + 0.1% Formic Acid	409.9 seconds	40023050
Life_Old = Waters ACQUITY UPLC BEH C18 with Water:(20:80 acetone:ACN) and 0.1% Formic Acid	140.3 seconds	40023050
Life_New = RP Waters ACQUITY UPLC HSS T3 C18 with Water:(30:70 MeOH:ACN) and 0.1% Formic Acid	272.6 seconds	40023050
RIKEN = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	90.9 seconds	40023050
Eawag_XBridgeC18 = XBridge C18 3.5u 2.1x50 mm with Water:MeOH and 0.1% Formic Acid	419.0 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	476.9 seconds	40023050
HILIC_BDD_2 = Merck SeQuant ZIC-HILIC with ACN(0.1% formic acid):water(16 mM ammonium formate)	119.9 seconds	40023050
UniToyama_Atlantis = RP Waters Atlantis T3 (2.1 x 150 mm, 5 um) with ACN:Water and 0.1% Formic Acid	955.9 seconds	40023050
BDD_C18 = Hypersil Gold 1.9µm C18 with Water:ACN and 0.1% Formic Acid	368.4 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	1120.9 seconds	40023050
SNU_RIKEN_POS = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	320.4 seconds	40023050
RPMMFDA = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	310.2 seconds	40023050
MTBLS87 = Merck SeQuant ZIC-pHILIC column with ACN:Water and :ammonium carbonate	424.8 seconds	40023050
KI_GIAR_zic_HILIC_pH2_7 = Merck SeQuant ZIC-HILIC with ACN:Water and 0.1% FA	375.9 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	69.3 seconds	40023050

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
Ethyl crotonate	CCOC(=O)\C=C/C	1171.6	Standard polar	33892256
Ethyl crotonate	CCOC(=O)\C=C/C	824.8	Standard non polar	33892256
Ethyl crotonate	CCOC(=O)\C=C/C	860.6	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 - Ethyl crotonate GC-MS (Non-derivatized) - 70eV, Positive	splash10-014i-9000000000-865c2f890d4c957c9ed2	2017-09-01	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Ethyl crotonate 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 - Ethyl crotonate 10V, Positive-QTOF	splash10-014i-5900000000-57ce442ea41ae31d8f4b	2017-09-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Ethyl crotonate 20V, Positive-QTOF	splash10-014i-9100000000-057912fbfafa02b78116	2017-09-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Ethyl crotonate 40V, Positive-QTOF	splash10-002f-9000000000-2b1ac297ad6411181115	2017-09-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Ethyl crotonate 10V, Negative-QTOF	splash10-03xr-8900000000-204f691b3b64230779e1	2017-09-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Ethyl crotonate 20V, Negative-QTOF	splash10-02t9-9200000000-43adce041ed532b36374	2017-09-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Ethyl crotonate 40V, Negative-QTOF	splash10-014v-9000000000-33d0bc00061d70ac9a8d	2017-09-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Ethyl crotonate 10V, Negative-QTOF	splash10-029b-9200000000-0a8b2c80be45ce4cc7e2	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Ethyl crotonate 20V, Negative-QTOF	splash10-014i-9000000000-6055217bcde1dfceb5ee	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Ethyl crotonate 40V, Negative-QTOF	splash10-00kg-9000000000-4445a937e70aa20c3608	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Ethyl crotonate 10V, Positive-QTOF	splash10-014l-9000000000-15296b102ad0314432f9	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Ethyl crotonate 20V, Positive-QTOF	splash10-014l-9000000000-050916a68b70b69d9f41	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Ethyl crotonate 40V, Positive-QTOF	splash10-0006-9000000000-bc7c86220df76df2b806	2021-09-22	Wishart Lab	View Spectrum

NMR Spectra

Spectrum Type	Description	Deposition Date	Source	View
Predicted 1D NMR	¹³C NMR Spectrum (1D, 100 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 100 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 1000 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 1000 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 200 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 200 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 300 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 300 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 400 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 400 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 500 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 500 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 600 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 600 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 700 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 700 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 800 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 800 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 900 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 900 MHz, D₂O, predicted)	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

Cytoplasm
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

FDB019204

KNApSAcK ID

C00052890

Chemspider ID

4510483

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

5354263

PDB ID

Not Available

ChEBI ID

87334

Food Biomarker Ontology

Not Available

VMH ID

Not Available

MarkerDB ID

Not Available

Good Scents ID

rw1433271

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 Ethyl crotonate (HMDB0039581)

MOL for HMDB0039581 (Ethyl crotonate)

3D MOL for HMDB0039581 (Ethyl crotonate)

3D SDF for HMDB0039581 (Ethyl crotonate)

3D-SDF for HMDB0039581 (Ethyl crotonate)

PDB for HMDB0039581 (Ethyl crotonate)

3D PDB for HMDB0039581 (Ethyl crotonate)

SMILES for HMDB0039581 (Ethyl crotonate)

INCHI for HMDB0039581 (Ethyl crotonate)

Structure for HMDB0039581 (Ethyl crotonate)

3D Structure for HMDB0039581 (Ethyl crotonate)

Predicted Collision Cross Sections

Predicted Retention Times

Underivatized

Predicted Kovats Retention Indices

Underivatized

GC-MS Spectra

MS/MS Spectra

NMR Spectra

IR Spectra