Record Information
Version1.0
Creation date2010-04-08 22:04:42 UTC
Update date2019-11-26 02:55:23 UTC
Primary IDFDB000774
Secondary Accession NumbersNot Available
Chemical Information
FooDB NameTiglic acid
DescriptionFlavouring 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 Number80-59-1
Structure
Thumb
Synonyms
SynonymSource
(Z)-2-Methylcrotonic acidChEBI
2-Methyl-2Z-butenoic acidChEBI
2-Methylisocrotonic acidChEBI
Acide angeliqueChEBI
Acido angelicoChEBI
alpha-Methylisocrotonic acidChEBI
AngelicasaeureChEBI
AngelikasaeureChEBI
cis-2,3-Dimethylacrylic acidChEBI
cis-2-Dimethylcrotonic acidChEBI
cis-2-Methyl-2-butenoic acidChEBI
Z-2-Methyl-2-butenoic acidChEBI
Z-2-Methylcrotonic acidChEBI
(Z)-2-MethylcrotonateGenerator
2-Methyl-2Z-butenoateGenerator
2-MethylisocrotonateGenerator
a-MethylisocrotonateGenerator
a-Methylisocrotonic acidGenerator
alpha-MethylisocrotonateGenerator
Α-methylisocrotonateGenerator
Α-methylisocrotonic acidGenerator
cis-2,3-DimethylacrylateGenerator
cis-2-DimethylcrotonateGenerator
cis-2-Methyl-2-butenoateGenerator
Z-2-Methyl-2-butenoateGenerator
Z-2-MethylcrotonateGenerator
AngelateGenerator
(2Z)-2-Methylbut-2-enoic acidHMDB
(Z)-2-Methyl-2-butenoic acidHMDB
2-Methyl-(2Z)-2-butenoic acidHMDB
2-Methyl-(Z)-2-butenoic acidHMDB
2-Methyl-(Z)-crotonic acidHMDB
2-Methyl-2-butenoic acid, cisHMDB
alpha-Methyl isocrotonic acidHMDB
Crotonic acid, 2-methyl-, (Z)- (8ci)HMDB
(2Z)-2-Methyl-2-butenoic acidHMDB
(Z)-2-Methylbut-2-enoic acidHMDB
(Z)-2-Methylbutenoic acidHMDB
cis-alpha,beta-Dimethylacrylic acidHMDB
cis-Α,β-dimethylacrylic acidHMDB
Angelic acidHMDB
TiglateGenerator
(2E)-2-Methyl-2-butenoatebiospider
(2e)-2-Methyl-2-butenoic acidHMDB
(E)-2-methyl-2-Butenoatebiospider
(E)-2-methyl-2-Butenoic acidbiospider
(E)-2-methyl-Crotonatebiospider
(E)-2-methyl-Crotonic acidbiospider
(e)-2-Methylbut-2-enoateGenerator
(e)-2-Methylbut-2-enoic acidChEBI
(E)-2-Methylcrotonatebiospider
(E)-2-Methylcrotonic acidbiospider
(E)-2,3-Dimethylacrylatebiospider
(E)-2,3-Dimethylacrylic acidbiospider
2-Butenoic acid, 2-methyl-biospider
2-Butenoic acid, 2-methyl-, (E)-biospider
2-methyl-(E)-2-butenoatebiospider
2-methyl-(E)-2-butenoic acidbiospider
2-methyl-2-butenoatebiospider
2-methyl-2-butenoic acidbiospider
2-methyl-Crotonatebiospider
2-methyl-Crotonic acidbiospider
2-Methylbut-2-enoatebiospider
2-Methylbut-2-enoic acidbiospider
2,3-Dimethylacrylatebiospider
2,3-Dimethylacrylic acidbiospider
Cevadatebiospider
Cevadic aciddb_source
Crotonic acid, 2-methyl-biospider
Crotonic acid, 2-methyl-, (E)-biospider
E-tiglatebiospider
E-tiglic acidbiospider
Epsilon-tiglatebiospider
Epsilon-tiglic acidbiospider
FEMA 3599db_source
Methyl methacrylateGenerator
Methyl methacrylic acidChEBI
Methylbutenoicacidbiospider
Tiglic aciddb_source
Tiglic acid, (e)-biospider
Tiglic acid, ebiospider
Tiglinatebiospider
Tiglinic acidbiospider
TiglinsaeureChEBI
Trans-α,β-dimethylacrylic acidbiospider
trans-2-Methyl-2-butenoatebiospider
trans-2-Methyl-2-butenoic acidbiospider
trans-2-Methylcrotonatebiospider
trans-2-Methylcrotonic acidbiospider
trans-2-Methylcrotonic acid = trans-2-Methyl-2-butenoatebiospider
trans-2-Methylcrotonic acid = trans-2-methyl-2-butenoic acidHMDB
trans-2-Methylcrotonic acid = trans-2-methyl-2-butenoic acid = tiglinateHMDB
trans-2-Methylcrotonic acid = trans-2-methyl-2-butenoic acid = tiglinic acidHMDB
trans-2,3-Dimethylacrylatebiospider
trans-2,3-Dimethylacrylic acidbiospider
trans-a,b-DimethylacrylateGenerator
trans-a,b-Dimethylacrylic acidGenerator
Trans-alpha,beta-dimethylacrylatebiospider
Trans-alpha,beta-dimethylacrylic acidbiospider
trans-α,β-dimethylacrylateGenerator
trans-α,β-dimethylacrylic acidGenerator
Predicted Properties
PropertyValueSource
logP1.32ChemAxon
pKa (Strongest Acidic)4.97ChemAxon
Physiological Charge-1ChemAxon
Hydrogen Acceptor Count2ChemAxon
Hydrogen Donor Count1ChemAxon
Polar Surface Area37.3 ŲChemAxon
Rotatable Bond Count1ChemAxon
Refractivity27.32 m³·mol⁻¹ChemAxon
Polarizability10.35 ųChemAxon
Number of Rings0ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Chemical FormulaC5H8O2
IUPAC name(2Z)-2-methylbut-2-enoic acid
InChI IdentifierInChI=1S/C5H8O2/c1-3-4(2)5(6)7/h3H,1-2H3,(H,6,7)/b4-3-
InChI KeyUIERETOOQGIECD-ARJAWSKDSA-N
Isomeric SMILESC\C=C(\C)C(O)=O
Average Molecular Weight100.1158
Monoisotopic Molecular Weight100.0524295
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.
KingdomOrganic compounds
Super ClassLipids and lipid-like molecules
ClassFatty Acyls
Sub ClassFatty acids and conjugates
Direct ParentMethyl-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 FrameworkAliphatic acyclic compounds
External Descriptors
Ontology
Disposition

Route of exposure:

Source:

Biological location:

Process

Naturally occurring process:

Role

Industrial application:

Biological role:

Physico-Chemical Properties - Experimental
Physico-Chemical Properties - Experimental
PropertyValueReference
Physical stateLiquid
Physical DescriptionNot Available
Mass CompositionC 59.98%; H 8.05%; O 31.96%DFC
Melting PointMp 63.5-64°DFC
Boiling PointBp11.5 95-96°DFC
Experimental Water SolubilityNot Available
Experimental logPNot Available
Experimental pKapKa 4.96 (18°)DFC
Isoelectric pointNot Available
ChargeNot Available
Optical RotationNot Available
Spectroscopic UV DataNot Available
DensityNot Available
Refractive IndexNot Available
Spectra
Spectra
Spectrum TypeDescriptionSplash KeyView
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-0zi0-9000000000-4314e75ba9656b7fb97fJSpectraViewer
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (1 TMS) - 70eV, Positivesplash10-0ab9-9200000000-1e8cf22de89b50fd327dJSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0udi-8900000000-68b09835981f85d65f90JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0a4i-9100000000-7999b5228e0df947f949JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0a4i-9000000000-179be6ce006eb4e9f084JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0002-9000000000-357a7c774a32d7c0444fJSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0a4j-9000000000-78eae8b34531c3c1bc27JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0a4i-9000000000-eb61c33f642ca5d4e676JSpectraViewer
ChemSpider ID111629
ChEMBL IDCHEMBL52416
KEGG Compound IDC08279
Pubchem Compound ID125468
Pubchem Substance IDNot Available
ChEBI ID9592
Phenol-Explorer IDNot Available
DrugBank IDNot Available
HMDB IDHMDB01470
CRC / DFC (Dictionary of Food Compounds) IDBHB40-W:BHB42-Y
EAFUS ID2273
Dr. Duke IDTIGLIC-ACID
BIGG IDNot Available
KNApSAcK IDC00001207
HET IDNot Available
Food Biomarker OntologyNot Available
VMH IDNot Available
Flavornet IDNot Available
GoodScent IDrw1010371
SuperScent IDNot Available
Wikipedia IDTiglic acid
Phenol-Explorer Metabolite IDNot Available
Duplicate IDSNot Available
Old DFC IDSNot Available
Associated Foods
FoodContent Range AverageReference
FoodReference
Biological Effects and Interactions
Health Effects / Bioactivities
DescriptorIDDefinitionReference
perfumery48318 A substance, extract, or preparation for diffusing or imparting an agreeable or attractive smell.DUKE
EnzymesNot Available
PathwaysNot Available
MetabolismNot Available
BiosynthesisNot Available
Organoleptic Properties
Flavours
FlavorCitations
sweet
  1. The Good Scents Company (2009). Flavor and fragrance information catalog. <http://www.thegoodscentscompany.com/allprod.html> Accessed 15.10.23.
dry
  1. The Good Scents Company (2009). Flavor and fragrance information catalog. <http://www.thegoodscentscompany.com/allprod.html> Accessed 15.10.23.
spicy
  1. The Good Scents Company (2009). Flavor and fragrance information catalog. <http://www.thegoodscentscompany.com/allprod.html> Accessed 15.10.23.
woody
  1. The Good Scents Company (2009). Flavor and fragrance information catalog. <http://www.thegoodscentscompany.com/allprod.html> Accessed 15.10.23.
caramel
  1. The Good Scents Company (2009). Flavor and fragrance information catalog. <http://www.thegoodscentscompany.com/allprod.html> Accessed 15.10.23.
Files
MSDSshow
References
Synthesis ReferenceNot Available
General ReferenceNot Available
Content Reference— Duke, James. 'Dr. Duke's Phytochemical and Ethnobotanical Databases. United States Department of Agriculture.' Agricultural Research Service, Accessed April 27 (2004).
— Shinbo, Y., et al. 'KNApSAcK: a comprehensive species-metabolite relationship database.' Plant Metabolomics. Springer Berlin Heidelberg, 2006. 165-181.