Showing Compound Tiglic acid (FDB000774)

Record Information

Version

1.0

Creation date

2010-04-08 22:04:42 UTC

Update date

2019-11-26 02:55:23 UTC

Primary ID

FDB000774

Secondary Accession Numbers

Not Available

Chemical Information

FooDB Name

Tiglic acid

Description

Flavouring ingredient A thick, syrupy poisonous liquid, C5H8O2, derived from croton oil, having a spicy odor and used in making perfumes and flavoring agents.; Tiglic acid has a double bond between the second and third carbons of the chain. Together with angelic acid form a pair of cis-trans isomers. Tiglic acid is a volatile and crystallizable substance with a sweet, warm spicy odour. It is used in making perfumes and flavoring agents.; Tiglic acid is a monocarboxylic unsaturated organic acid. It is found in croton oil and in several other natural products. It was also isolated from the defensive secretion of certain beetles.; Tiglic acid is a skin and eye irritant. The inhalation of the substance causes respiratory tract irritation. It is listed on the Toxic Substances Control Act (TSCA).

CAS Number

80-59-1

Structure

MOL SDF PDB SMILES InChI

Synonyms

Synonym	Source
(Z)-2-Methylcrotonic acid	ChEBI
2-Methyl-2Z-butenoic acid	ChEBI
2-Methylisocrotonic acid	ChEBI
Acide angelique	ChEBI
Acido angelico	ChEBI
alpha-Methylisocrotonic acid	ChEBI
Angelicasaeure	ChEBI
Angelikasaeure	ChEBI
cis-2,3-Dimethylacrylic acid	ChEBI
cis-2-Dimethylcrotonic acid	ChEBI
cis-2-Methyl-2-butenoic acid	ChEBI
Z-2-Methyl-2-butenoic acid	ChEBI
Z-2-Methylcrotonic acid	ChEBI
(Z)-2-Methylcrotonate	Generator
2-Methyl-2Z-butenoate	Generator
2-Methylisocrotonate	Generator
a-Methylisocrotonate	Generator
a-Methylisocrotonic acid	Generator
alpha-Methylisocrotonate	Generator
Α-methylisocrotonate	Generator
Α-methylisocrotonic acid	Generator
cis-2,3-Dimethylacrylate	Generator
cis-2-Dimethylcrotonate	Generator
cis-2-Methyl-2-butenoate	Generator
Z-2-Methyl-2-butenoate	Generator
Z-2-Methylcrotonate	Generator
Angelate	Generator
(2Z)-2-Methylbut-2-enoic acid	HMDB
(Z)-2-Methyl-2-butenoic acid	HMDB
2-Methyl-(2Z)-2-butenoic acid	HMDB
2-Methyl-(Z)-2-butenoic acid	HMDB
2-Methyl-(Z)-crotonic acid	HMDB
2-Methyl-2-butenoic acid, cis	HMDB
alpha-Methyl isocrotonic acid	HMDB
Crotonic acid, 2-methyl-, (Z)- (8ci)	HMDB
(2Z)-2-Methyl-2-butenoic acid	HMDB
(Z)-2-Methylbut-2-enoic acid	HMDB
(Z)-2-Methylbutenoic acid	HMDB
Angelic acid	HMDB
cis-alpha,beta-Dimethylacrylic acid	HMDB
cis-α,β-Dimethylacrylic acid	HMDB
Tiglate	Generator
(2E)-2-Methyl-2-butenoate	biospider
(2e)-2-Methyl-2-butenoic acid	HMDB
(E)-2-methyl-2-Butenoate	biospider
(E)-2-methyl-2-Butenoic acid	biospider
(E)-2-methyl-Crotonate	biospider
(E)-2-methyl-Crotonic acid	biospider
(e)-2-Methylbut-2-enoate	Generator
(e)-2-Methylbut-2-enoic acid	ChEBI
(E)-2-Methylcrotonate	biospider
(E)-2-Methylcrotonic acid	biospider
(E)-2,3-Dimethylacrylate	biospider
(E)-2,3-Dimethylacrylic acid	biospider
2-Butenoic acid, 2-methyl-	biospider
2-Butenoic acid, 2-methyl-, (E)-	biospider
2-methyl-(E)-2-butenoate	biospider
2-methyl-(E)-2-butenoic acid	biospider
2-methyl-2-butenoate	biospider
2-methyl-2-butenoic acid	biospider
2-methyl-Crotonate	biospider
2-methyl-Crotonic acid	biospider
2-Methylbut-2-enoate	biospider
2-Methylbut-2-enoic acid	biospider
2,3-Dimethylacrylate	biospider
2,3-Dimethylacrylic acid	biospider
Cevadate	biospider
Cevadic acid	db_source
Crotonic acid, 2-methyl-	biospider
Crotonic acid, 2-methyl-, (E)-	biospider
E-tiglate	biospider
E-tiglic acid	biospider
Epsilon-tiglate	biospider
Epsilon-tiglic acid	biospider
FEMA 3599	db_source
Methyl methacrylate	Generator
Methyl methacrylic acid	ChEBI
Methylbutenoicacid	biospider
Tiglic acid	db_source
Tiglic acid, (e)-	biospider
Tiglic acid, e	biospider
Tiglinate	biospider
Tiglinic acid	biospider
Tiglinsaeure	ChEBI
Trans-α,β-dimethylacrylic acid	biospider
trans-2-Methyl-2-butenoate	biospider
trans-2-Methyl-2-butenoic acid	biospider
trans-2-Methylcrotonate	biospider
trans-2-Methylcrotonic acid	biospider
trans-2-Methylcrotonic acid = trans-2-Methyl-2-butenoate	biospider
trans-2-Methylcrotonic acid = trans-2-methyl-2-butenoic acid	HMDB
trans-2-Methylcrotonic acid = trans-2-methyl-2-butenoic acid = tiglinate	HMDB
trans-2-Methylcrotonic acid = trans-2-methyl-2-butenoic acid = tiglinic acid	HMDB
trans-2,3-Dimethylacrylate	biospider
trans-2,3-Dimethylacrylic acid	biospider
trans-a,b-Dimethylacrylate	Generator
trans-a,b-Dimethylacrylic acid	Generator
Trans-alpha,beta-dimethylacrylate	biospider
Trans-alpha,beta-dimethylacrylic acid	biospider
trans-α,β-dimethylacrylate	Generator
trans-α,β-dimethylacrylic acid	Generator

Predicted Properties

Property	Value	Source
logP	1.32	ChemAxon
pKa (Strongest Acidic)	4.97	ChemAxon
Physiological Charge	-1	ChemAxon
Hydrogen Acceptor Count	2	ChemAxon
Hydrogen Donor Count	1	ChemAxon
Polar Surface Area	37.3 Å²	ChemAxon
Rotatable Bond Count	1	ChemAxon
Refractivity	27.32 m³·mol⁻¹	ChemAxon
Polarizability	10.35 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

Chemical Formula

C5H8O2

IUPAC name

(2Z)-2-methylbut-2-enoic acid

InChI Identifier

InChI=1S/C5H8O2/c1-3-4(2)5(6)7/h3H,1-2H3,(H,6,7)/b4-3-

InChI Key

UIERETOOQGIECD-ARJAWSKDSA-N

Isomeric SMILES

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

Average Molecular Weight

100.1158

Monoisotopic Molecular Weight

100.0524295

Classification

Description

Belongs to the class of organic compounds known as methyl-branched fatty acids. These are fatty acids with an acyl chain that has a methyl branch. Usually, they are saturated and contain only one or more methyl group. However, branches other than methyl may be present.

Kingdom

Organic compounds

Super Class

Lipids and lipid-like molecules

Class

Fatty Acyls

Sub Class

Fatty acids and conjugates

Direct Parent

Methyl-branched fatty acids

Alternative Parents

Substituents

Methyl-branched fatty acid
Unsaturated fatty acid
Monocarboxylic acid or derivatives
Carboxylic acid
Carboxylic acid derivative
Organic oxygen compound
Organic oxide
Hydrocarbon derivative
Organooxygen compound
Carbonyl group
Aliphatic acyclic compound

Molecular Framework

Aliphatic acyclic compounds

External Descriptors

2-methylbut-2-enoic acid (CHEBI:36431 )
Branched fatty acids (LMFA01020029 )

Ontology

Disposition

Route of exposure:

Enteral:

Ingestion

Source:

Biological:

Biological location:

Biofluid and excreta:

Urine

Subcellular:

Cell and elements:

Extracellular

Process

Naturally occurring process:

Biological process:

Biochemical process:

Chemical reaction:

Lipid peroxidation

Biochemical pathway:

Lipid metabolism pathway

Cellular process:

Cell signaling

Role

Industrial application:

Biological role:

Physico-Chemical Properties

Physico-Chemical Properties - Experimental

Property	Value	Reference
Physical state	Liquid
Physical Description	Not Available
Mass Composition	C 59.98%; H 8.05%; O 31.96%	DFC
Melting Point	Mp 63.5-64°	DFC
Boiling Point	Bp11.5 95-96°	DFC
Experimental Water Solubility	Not Available
Experimental logP	Not Available
Experimental pKa	pKa 4.96 (18°)	DFC
Isoelectric point	Not Available
Charge	Not Available
Optical Rotation	Not Available
Spectroscopic UV Data	Not Available
Density	Not Available
Refractive Index	Not Available

Spectra

EI-MS/GC-MS

Type	Description	Splash Key	View
Predicted GC-MS	Tiglic acid, non-derivatized, Predicted GC-MS Spectrum - 70eV, Positive	splash10-0zi0-9000000000-4314e75ba9656b7fb97f	Spectrum
Predicted GC-MS	Tiglic acid, 1 TMS, Predicted GC-MS Spectrum - 70eV, Positive	splash10-0ab9-9200000000-1e8cf22de89b50fd327d	Spectrum
Predicted GC-MS	Tiglic acid, non-derivatized, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Tiglic acid, non-derivatized, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum

MS/MS

Type	Description	Splash Key	View
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-0udi-8900000000-68b09835981f85d65f90	2016-08-03	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-0a4i-9100000000-7999b5228e0df947f949	2016-08-03	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-0a4i-9000000000-179be6ce006eb4e9f084	2016-08-03	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-0002-9000000000-357a7c774a32d7c0444f	2016-08-03	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-0a4j-9000000000-78eae8b34531c3c1bc27	2016-08-03	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-0a4i-9000000000-eb61c33f642ca5d4e676	2016-08-03	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-001i-9000000000-0cc8aed45af20d83ec92	2021-09-23	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-0a4i-9000000000-821598b1a2e8057a3567	2021-09-23	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-0a4r-9000000000-5e5e9fc82472025ff503	2021-09-23	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-0002-9000000000-5289cc75fe7aae11de79	2021-09-25	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-000t-9000000000-16cd54f70787a892bf2b	2021-09-25	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-052f-9000000000-59b712b76240ebaa6888	2021-09-25	View Spectrum

NMR

Not Available

External Links

ChemSpider ID

ChEMBL ID

KEGG Compound ID

Pubchem Compound ID

Pubchem Substance ID

Not Available

ChEBI ID

9592

Phenol-Explorer ID

Not Available

DrugBank ID

Not Available

HMDB ID

HMDB01470

CRC / DFC (Dictionary of Food Compounds) ID

BHB40-W:BHB42-Y

EAFUS ID

2273

Dr. Duke ID

TIGLIC-ACID

BIGG ID

Not Available

KNApSAcK ID

C00001207

HET ID

Not Available

Food Biomarker Ontology

Not Available

VMH ID

Not Available

Flavornet ID

Not Available

GoodScent ID

rw1010371

SuperScent ID

Not Available

Wikipedia ID

Tiglic acid

Phenol-Explorer Metabolite ID

Not Available

Duplicate IDS

Not Available

Old DFC IDS

Not Available

Associated Foods

Food	Content Range	Average	Reference
Food			Reference

Biological Effects and Interactions

Health Effects / Bioactivities

Descriptor	ID	Definition	Reference
Perfumery	48318	The art of creating fragrances, playing a biological role in emotional and sensory stimulation. Therapeutically, perfumery has applications in aromatherapy, reducing stress and anxiety. Key medical uses include mood enhancement, pain management, and promoting relaxation, with certain scents exhibiting anti-anxiety and anti-depressant properties.	DUKE

Enzymes

Not Available

Pathways

Not Available

Metabolism

Not Available

Biosynthesis

Not Available

Organoleptic Properties

Flavours

Flavor	Citations
sweet	The Good Scents Company (2009). Flavor and fragrance information catalog. <http://www.thegoodscentscompany.com/allprod.html> Accessed 15.10.23.
dry	The Good Scents Company (2009). Flavor and fragrance information catalog. <http://www.thegoodscentscompany.com/allprod.html> Accessed 15.10.23.
spicy	The Good Scents Company (2009). Flavor and fragrance information catalog. <http://www.thegoodscentscompany.com/allprod.html> Accessed 15.10.23.
woody	The Good Scents Company (2009). Flavor and fragrance information catalog. <http://www.thegoodscentscompany.com/allprod.html> Accessed 15.10.23.
caramel	The Good Scents Company (2009). Flavor and fragrance information catalog. <http://www.thegoodscentscompany.com/allprod.html> Accessed 15.10.23.