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Record Information

Version

5.0

Status

Detected but not Quantified

Creation Date

2012-09-11 17:31:16 UTC

Update Date

2023-02-21 17:18:50 UTC

HMDB ID

HMDB0029582

Secondary Accession Numbers

HMDB29582

Metabolite Identification

Common Name

Methyl sorbate

Description

Methyl sorbate 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 Methyl sorbate.

Structure

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

View in JSmol View NMR Assignments View Stereo Labels

Synonyms

Value	Source
Methyl sorbic acid	Generator
(e,e)-2,4-Hexadienoic acid methyl ester	HMDB
(e,e)-Methyl 2,4-hexadienoate	HMDB
(e,e)-Methyl sorbate	HMDB
2,4-Hexadienoic acid, methyl ester	HMDB
2,4-Hexadienoic acid, methyl ester (9ci)	HMDB
2-trans,4-trans-Methyl sorbate	HMDB
2-trans-4-trans-Methyl sorbate	HMDB
FEMA 3714	HMDB
Methyl (2E,4E)-2,4-hexadienoate	HMDB
Methyl (2E,4E)-hexadienoate	HMDB
Methyl (e,e)-2,4-hexadienoate	HMDB
Methyl (e,e)-hexa-2,4-dienoate	HMDB
Methyl (e,e)-sorbate	HMDB
Methyl 2,4-hexadienoate	HMDB
Methyl ester(2E,4E)-2,4-hexadienoic acid	HMDB
Methyl ester(e,e)-2,4-hexadienoic acid	HMDB
Methyl ester(e,e)-sorbic acid	HMDB
Methyl hexa-2,4-dienoate	HMDB
Methyl trans,trans-sorbate	HMDB
Sorbic acid, methyl ester	HMDB

Chemical Formula

C₇H₁₀O₂

Average Molecular Weight

126.1531

Monoisotopic Molecular Weight

126.068079564

IUPAC Name

methyl (2E,4E)-hexa-2,4-dienoate

Traditional Name

methyl (2E,4E)-hexa-2,4-dienoate

CAS Registry Number

689-89-4

SMILES

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

InChI Identifier

InChI=1S/C7H10O2/c1-3-4-5-6-7(8)9-2/h3-6H,1-2H3/b4-3+,6-5+

InChI Key

KWKVAGQCDSHWFK-VNKDHWASSA-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
Methyl 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

Physiological effect

Organoleptic effect

Taste

Pungent

Odor

Disposition

Biological location

Cellular substructure

Excreta

Biofluid or Excreta

Urine (HMDB: HMDB0029582)

Route of exposure

Enteral

Ingestion (HMDB: HMDB0029582)

Source

Endogenous

Endogenous (HMDB: HMDB0029582)

Animal

Animal (HMDB: HMDB0029582)

Exogenous

Food

Food (HMDB: HMDB0029582)

Exogenous (HMDB: HMDB0029582)

Process

Naturally occurring process

Biological process

Chemical reaction

Lipid Peroxidation (HMDB: HMDB0029582)

Biochemical pathway

Metabolic pathway

Fatty Acid Metabolism (HMDB: HMDB0029582)

Lipid metabolism pathway (HMDB: HMDB0029582)

Cellular process

Cell signaling (HMDB: HMDB0029582)

Biochemical process

Lipid transport (HMDB: HMDB0029582)

Role

Biological role

Energy source (HMDB: HMDB0029582)

Industrial application

Manufacturing industry

Material processing agent

Fluid processing agent

Surfactant

Surfactant (HMDB: HMDB0029582)

Food and nutrition

Food additive

Flavoring agent

Flavoring Agent (HMDB: HMDB0029582)

Physical Properties

State

Liquid

Experimental Molecular Properties

Property	Value	Reference
Melting Point	5 °C	Not Available
Boiling Point	180.00 °C. @ 760.00 mm Hg	The Good Scents Company Information System
Water Solubility	2236 mg/L @ 25 °C (est)	The Good Scents Company Information System
LogP	1.861 (est)	The Good Scents Company Information System

Experimental Chromatographic Properties

Not Available

Predicted Molecular Properties

Property	Value	Source
Water Solubility	1.65 g/L	ALOGPS
logP	1.89	ALOGPS
logP	1.83	ChemAxon
logS	-1.9	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	38.05 m³·mol⁻¹	ChemAxon
Polarizability	14.08 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]+	131.744	31661259
DarkChem	[M-H]-	127.031	31661259
DeepCCS	[M+H]+	126.353	30932474
DeepCCS	[M-H]-	123.219	30932474
DeepCCS	[M-2H]-	160.197	30932474
DeepCCS	[M+Na]+	135.234	30932474
AllCCS	[M+H]+	129.5	32859911
AllCCS	[M+H-H2O]+	125.2	32859911
AllCCS	[M+NH4]+	133.5	32859911
AllCCS	[M+Na]+	134.7	32859911
AllCCS	[M-H]-	128.0	32859911
AllCCS	[M+Na-2H]-	130.7	32859911
AllCCS	[M+HCOO]-	133.7	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.	4.98 minutes	32390414
Predicted by Siyang on May 30, 2022	13.1685 minutes	33406817
Predicted by Siyang using ReTip algorithm on June 8, 2022	3.23 minutes	32390414
Fem_Long = Waters ACQUITY UPLC HSS T3 C18 with Water:MeOH and 0.1% Formic Acid	1850.4 seconds	40023050
Fem_Lipids = Ascentis Express C18 with (60:40 water:ACN):(90:10 IPA:ACN) and 10mM NH4COOH + 0.1% Formic Acid	413.3 seconds	40023050
Life_Old = Waters ACQUITY UPLC BEH C18 with Water:(20:80 acetone:ACN) and 0.1% Formic Acid	154.7 seconds	40023050
Life_New = RP Waters ACQUITY UPLC HSS T3 C18 with Water:(30:70 MeOH:ACN) and 0.1% Formic Acid	301.3 seconds	40023050
RIKEN = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	105.8 seconds	40023050
Eawag_XBridgeC18 = XBridge C18 3.5u 2.1x50 mm with Water:MeOH and 0.1% Formic Acid	436.1 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	429.2 seconds	40023050
HILIC_BDD_2 = Merck SeQuant ZIC-HILIC with ACN(0.1% formic acid):water(16 mM ammonium formate)	84.8 seconds	40023050
UniToyama_Atlantis = RP Waters Atlantis T3 (2.1 x 150 mm, 5 um) with ACN:Water and 0.1% Formic Acid	1155.0 seconds	40023050
BDD_C18 = Hypersil Gold 1.9µm C18 with Water:ACN and 0.1% Formic Acid	413.6 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	1006.2 seconds	40023050
SNU_RIKEN_POS = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	341.7 seconds	40023050
RPMMFDA = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	337.3 seconds	40023050
MTBLS87 = Merck SeQuant ZIC-pHILIC column with ACN:Water and :ammonium carbonate	376.1 seconds	40023050
KI_GIAR_zic_HILIC_pH2_7 = Merck SeQuant ZIC-HILIC with ACN:Water and 0.1% FA	423.8 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	56.2 seconds	40023050

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
Methyl sorbate	COC(=O)\C=C\C=C\C	1528.1	Standard polar	33892256
Methyl sorbate	COC(=O)\C=C\C=C\C	998.4	Standard non polar	33892256
Methyl sorbate	COC(=O)\C=C\C=C\C	1063.1	Semi standard non polar	33892256

Spectra

GC-MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Experimental GC-MS	GC-MS Spectrum - Methyl sorbate EI-B (Non-derivatized)	splash10-02t9-9600000000-644e86a7cf81a828f04e	2017-09-12	HMDB team, MONA, MassBank	View Spectrum
Experimental GC-MS	GC-MS Spectrum - Methyl sorbate EI-B (Non-derivatized)	splash10-0401-8900000000-29d57d8fbbe1a767d341	2017-09-12	HMDB team, MONA, MassBank	View Spectrum
Experimental GC-MS	GC-MS Spectrum - Methyl sorbate CI-B (Non-derivatized)	splash10-004i-1900000000-eb1a9dd3ee8621c4933a	2017-09-12	HMDB team, MONA, MassBank	View Spectrum
Experimental GC-MS	GC-MS Spectrum - Methyl sorbate EI-B (Non-derivatized)	splash10-014i-9100000000-6c402f3f828ad7813f02	2017-09-12	HMDB team, MONA, MassBank	View Spectrum
Experimental GC-MS	GC-MS Spectrum - Methyl sorbate EI-B (Non-derivatized)	splash10-02t9-9600000000-644e86a7cf81a828f04e	2018-05-18	HMDB team, MONA, MassBank	View Spectrum
Experimental GC-MS	GC-MS Spectrum - Methyl sorbate EI-B (Non-derivatized)	splash10-0401-8900000000-29d57d8fbbe1a767d341	2018-05-18	HMDB team, MONA, MassBank	View Spectrum
Experimental GC-MS	GC-MS Spectrum - Methyl sorbate CI-B (Non-derivatized)	splash10-004i-1900000000-eb1a9dd3ee8621c4933a	2018-05-18	HMDB team, MONA, MassBank	View Spectrum
Experimental GC-MS	GC-MS Spectrum - Methyl sorbate EI-B (Non-derivatized)	splash10-014i-9100000000-6c402f3f828ad7813f02	2018-05-18	HMDB team, MONA, MassBank	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Methyl sorbate GC-MS (Non-derivatized) - 70eV, Positive	splash10-016r-9100000000-db21d9e5fa3e5ab98e97	2017-09-01	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Methyl sorbate 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 - Methyl sorbate 10V, Positive-QTOF	splash10-004j-9600000000-5743d3c0155f1c9b0ea9	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Methyl sorbate 20V, Positive-QTOF	splash10-0ufr-9200000000-0a4af525ad1fe34c0026	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Methyl sorbate 40V, Positive-QTOF	splash10-0udi-9000000000-6711e1dd39204ef88bc9	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Methyl sorbate 10V, Negative-QTOF	splash10-004i-5900000000-ec9a2cb10acf1084d611	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Methyl sorbate 20V, Negative-QTOF	splash10-004l-9600000000-546dc27b7df4b506a06f	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Methyl sorbate 40V, Negative-QTOF	splash10-0006-9000000000-4d6f80d79ef5b93b00a8	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Methyl sorbate 10V, Negative-QTOF	splash10-0006-9000000000-08485aaf085c13d5129a	2021-09-25	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Methyl sorbate 20V, Negative-QTOF	splash10-004l-9000000000-7643075051c69ab19407	2021-09-25	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Methyl sorbate 40V, Negative-QTOF	splash10-03xr-9000000000-e9908d8a358867139b55	2021-09-25	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Methyl sorbate 10V, Positive-QTOF	splash10-014i-9000000000-860e38eee22406024c2c	2021-09-25	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Methyl sorbate 20V, Positive-QTOF	splash10-014i-9000000000-73af235443806c415e3b	2021-09-25	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Methyl sorbate 40V, Positive-QTOF	splash10-014i-9000000000-b8281b4aa57903036d9f	2021-09-25	Wishart Lab	View Spectrum

NMR Spectra

Spectrum Type	Description	Deposition Date	Source	View
Predicted 1D NMR	¹H NMR Spectrum (1D, 100 MHz, D₂O, predicted)	2021-09-30	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 100 MHz, D₂O, predicted)	2021-09-30	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 1000 MHz, D₂O, predicted)	2021-09-30	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 1000 MHz, D₂O, predicted)	2021-09-30	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 200 MHz, D₂O, predicted)	2021-09-30	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 200 MHz, D₂O, predicted)	2021-09-30	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 300 MHz, D₂O, predicted)	2021-09-30	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 300 MHz, D₂O, predicted)	2021-09-30	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 400 MHz, D₂O, predicted)	2021-09-30	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 400 MHz, D₂O, predicted)	2021-09-30	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 500 MHz, D₂O, predicted)	2021-09-30	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 500 MHz, D₂O, predicted)	2021-09-30	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 600 MHz, D₂O, predicted)	2021-09-30	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 600 MHz, D₂O, predicted)	2021-09-30	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 700 MHz, D₂O, predicted)	2021-09-30	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 700 MHz, D₂O, predicted)	2021-09-30	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 800 MHz, D₂O, predicted)	2021-09-30	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 800 MHz, D₂O, predicted)	2021-09-30	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 900 MHz, D₂O, predicted)	2021-09-30	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 900 MHz, D₂O, predicted)	2021-09-30	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]+)	2023-02-03	FELIX lab	View Spectrum
Predicted IR Spectrum	IR Ion Spectrum (Predicted IRIS Spectrum, Adduct: [M+Na]+)	2023-02-03	FELIX lab	View Spectrum

Biological Properties

Cellular Locations

Cytoplasm
Extracellular
Membrane

Biospecimen Locations

Blood
Urine

Tissue Locations

Not Available

Pathways

Not Available

Name	SMPDB/PathBank	KEGG

Normal Concentrations

Biospecimen	Status	Value	Age	Sex	Condition	Reference	Details
Blood	Expected but not Quantified	Not Quantified	Not Specified	Not Specified	Normal	34436864	details
Urine	Detected but not Quantified	Not Quantified	Not Specified	Not Specified	Normal	34436864	details

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

FDB000739

KNApSAcK ID

Not Available

Chemspider ID

4481192

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

5323650

PDB ID

Not Available

ChEBI ID

515741

Food Biomarker Ontology

Not Available

VMH ID

Not Available

MarkerDB ID

Not Available

Good Scents ID

rw1037591

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 Methyl sorbate (HMDB0029582)

MOL for HMDB0029582 (Methyl sorbate)

3D MOL for HMDB0029582 (Methyl sorbate)

3D SDF for HMDB0029582 (Methyl sorbate)

3D-SDF for HMDB0029582 (Methyl sorbate)

PDB for HMDB0029582 (Methyl sorbate)

3D PDB for HMDB0029582 (Methyl sorbate)

SMILES for HMDB0029582 (Methyl sorbate)

INCHI for HMDB0029582 (Methyl sorbate)

Structure for HMDB0029582 (Methyl sorbate)

3D Structure for HMDB0029582 (Methyl sorbate)

Predicted Collision Cross Sections

Predicted Retention Times

Underivatized

Predicted Kovats Retention Indices

Underivatized

GC-MS Spectra

MS/MS Spectra

NMR Spectra

IR Spectra