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Identification Taxonomy Ontology Physical properties Spectra Biological properties Concentrations Links References XML

Record Information

Version

5.0

Status

Expected but not Quantified

Creation Date

2012-09-11 22:52:33 UTC

Update Date

2023-02-21 17:25:53 UTC

HMDB ID

HMDB0037624

Secondary Accession Numbers

HMDB37624

Metabolite Identification

Common Name

Isopropyl tiglate

Description

Isopropyl tiglate 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 Isopropyl tiglate.

Structure

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

View in JSmol View NMR Assignments View Stereo Labels

Synonyms

Value	Source
Isopropyl tiglic acid	Generator
(e)-1-Methylethyl 2-methyl-2-butenoate	HMDB
2-Butenoic acid, 2-methyl-, 1-methylethyl ester, (e)- (9ci)	HMDB
2-Methyl-1-isopropyl ester(e)-2-butenoic acid	HMDB
2-Methyl-1-methylethyl ester(2E)-2-butenoic acid	HMDB
2-Methyl-1-methylethyl ester(e)-2-butenoic acid	HMDB
2-Methyl-propyl ester(e)-2-butenoicacid	HMDB
2-Methyl1-isopropyl ester (e)-2-butenoic acid	HMDB
3-Methyl,2-butenoic acid,isopropyl ester	HMDB
3-Methyl-2-butenoic acid, isopropyl ester	HMDB
FEMA 3229	HMDB
Isopropyl (2E)-2-methyl-2-butenoate	HMDB
Isopropyl 2-methyl-2-butenoate	HMDB
Isopropyl 2-methylcrotonate	HMDB
Isopropyl 3-methyl-2-butenoate	HMDB
Isopropyl alpha -methyl crotonate	HMDB
Isopropyl alpha-methyl crotonate	HMDB
Isopropyl alpha-methylcrotonate	HMDB
Isopropyltiglate	HMDB
Tiglic acid isopropyl ester	HMDB

Chemical Formula

C₈H₁₄O₂

Average Molecular Weight

142.1956

Monoisotopic Molecular Weight

142.099379692

IUPAC Name

propan-2-yl (2Z)-2-methylbut-2-enoate

Traditional Name

isopropyl (2Z)-2-methylbut-2-enoate

CAS Registry Number

1733-25-1

SMILES

C\C=C(\C)C(=O)OC(C)C

InChI Identifier

InChI=1S/C8H14O2/c1-5-7(4)8(9)10-6(2)3/h5-6H,1-4H3/b7-5-

InChI Key

VUPBIVVRPJDWNW-ALCCZGGFSA-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

Not Available

Ontology

Physiological effect

Organoleptic effect

Taste

Sweet

Odor

Disposition

Biological location

Cellular substructure

Excreta

Biofluid or Excreta

Urine (HMDB: HMDB0037624)

Route of exposure

Enteral

Ingestion (HMDB: HMDB0037624)

Source

Endogenous

Endogenous (HMDB: HMDB0037624)

Animal

Animal (HMDB: HMDB0037624)

Exogenous

Food

Food (HMDB: HMDB0037624)

Process

Naturally occurring process

Biological process

Biochemical pathway

Metabolic pathway

Fatty Acid Metabolism (HMDB: HMDB0037624)

Chemical reaction

Lipid Peroxidation (HMDB: HMDB0037624)

Cellular process

Cell signaling (HMDB: HMDB0037624)

Biochemical process

Lipid transport (HMDB: HMDB0037624)

Role

Biological role

Energy storage (HMDB: HMDB0037624)

Industrial application

Manufacturing industry

Material processing agent

Fluid processing agent

Surfactant

Surfactant (HMDB: HMDB0037624)

Food and nutrition

Food additive

Flavoring agent

Flavoring Agent (HMDB: HMDB0037624)

Physical Properties

State

Not Available

Experimental Molecular Properties

Property	Value	Reference
Melting Point	Not Available	Not Available
Boiling Point	73.00 °C. @ 30.00 mm Hg	The Good Scents Company Information System
Water Solubility	497.1 mg/L @ 25 °C (est)	The Good Scents Company Information System
LogP	2.578 (est)	The Good Scents Company Information System

Experimental Chromatographic Properties

Not Available

Predicted Molecular Properties

Property	Value	Source
Water Solubility	3.11 g/L	ALOGPS
logP	2.64	ALOGPS
logP	2.47	ChemAxon
logS	-1.7	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	41.26 m³·mol⁻¹	ChemAxon
Polarizability	16.3 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]+	133.565	31661259
DarkChem	[M-H]-	128.573	31661259
DeepCCS	[M+H]+	135.522	30932474
DeepCCS	[M-H]-	132.965	30932474
DeepCCS	[M-2H]-	168.908	30932474
DeepCCS	[M+Na]+	143.693	30932474
AllCCS	[M+H]+	134.2	32859911
AllCCS	[M+H-H2O]+	130.2	32859911
AllCCS	[M+NH4]+	137.9	32859911
AllCCS	[M+Na]+	138.9	32859911
AllCCS	[M-H]-	133.1	32859911
AllCCS	[M+Na-2H]-	135.5	32859911
AllCCS	[M+HCOO]-	138.3	32859911

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
Isopropyl tiglate	C\C=C(\C)C(=O)OC(C)C	1250.3	Standard polar	33892256
Isopropyl tiglate	C\C=C(\C)C(=O)OC(C)C	912.8	Standard non polar	33892256
Isopropyl tiglate	C\C=C(\C)C(=O)OC(C)C	931.0	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 - Isopropyl tiglate GC-MS (Non-derivatized) - 70eV, Positive	splash10-0536-9000000000-7327aedb6b28a923f18c	2017-09-01	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Isopropyl tiglate 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 - Isopropyl tiglate 10V, Positive-QTOF	splash10-0006-3900000000-341b66f9956ba01bc2a1	2017-09-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Isopropyl tiglate 20V, Positive-QTOF	splash10-0kcu-9300000000-2c5267d77b6f220b6bff	2017-09-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Isopropyl tiglate 40V, Positive-QTOF	splash10-0pb9-9000000000-893abdb8aee38228c699	2017-09-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Isopropyl tiglate 10V, Negative-QTOF	splash10-0006-2900000000-17a13be25d4060584ef8	2017-09-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Isopropyl tiglate 20V, Negative-QTOF	splash10-052f-9700000000-eb6cd9f59c62abecfada	2017-09-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Isopropyl tiglate 40V, Negative-QTOF	splash10-0a4i-9000000000-1d30968b735cb54974bf	2017-09-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Isopropyl tiglate 10V, Positive-QTOF	splash10-0f89-9300000000-da82f92d34d5e59cb644	2021-09-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Isopropyl tiglate 20V, Positive-QTOF	splash10-0a4i-9000000000-0ad5767bc35c87ecd189	2021-09-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Isopropyl tiglate 40V, Positive-QTOF	splash10-0a4u-9000000000-bf17438fb0d5055bfedf	2021-09-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Isopropyl tiglate 10V, Negative-QTOF	splash10-0005-9600000000-e53b31f2187e978c0d91	2021-09-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Isopropyl tiglate 20V, Negative-QTOF	splash10-053u-9100000000-aab7b7998111e628d97c	2021-09-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Isopropyl tiglate 40V, Negative-QTOF	splash10-0a4i-9000000000-0fa77c133c14b1842b88	2021-09-24	Wishart Lab	View Spectrum

NMR Spectra

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

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

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

FDB016738

KNApSAcK ID

Not Available

Chemspider ID

4938109

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

6432902

PDB ID

Not Available

ChEBI ID

Not Available

Food Biomarker Ontology

Not Available

VMH ID

Not Available

MarkerDB ID

Not Available

Good Scents ID

rw1035621

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 Isopropyl tiglate (HMDB0037624)

MOL for HMDB0037624 (Isopropyl tiglate)

3D MOL for HMDB0037624 (Isopropyl tiglate)

3D SDF for HMDB0037624 (Isopropyl tiglate)

3D-SDF for HMDB0037624 (Isopropyl tiglate)

PDB for HMDB0037624 (Isopropyl tiglate)

3D PDB for HMDB0037624 (Isopropyl tiglate)

SMILES for HMDB0037624 (Isopropyl tiglate)

INCHI for HMDB0037624 (Isopropyl tiglate)

Structure for HMDB0037624 (Isopropyl tiglate)

3D Structure for HMDB0037624 (Isopropyl tiglate)

Predicted Collision Cross Sections

Predicted Kovats Retention Indices

Underivatized

GC-MS Spectra

MS/MS Spectra

NMR Spectra

IR Spectra