Record Information
Version1.0
Creation date2010-04-08 22:04:42 UTC
Update date2015-10-09 22:29:32 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
(e)-2,3-Dimethylacrylic acidChEBI
(e)-2-Methylbut-2-enoic acidChEBI
(e)-2-Methylcrotonic acidChEBI
Methyl methacrylic acidChEBI
TiglinsaeureChEBI
trans-2,3-Dimethylacrylic acidChEBI
trans-2-Methyl-2-butenoic acidChEBI
trans-2-Methylcrotonic acidChEBI
trans-alpha,beta-Dimethylacrylic acidChEBI
(e)-2,3-DimethylacrylateGenerator
(e)-2-Methylbut-2-enoateGenerator
(e)-2-MethylcrotonateGenerator
Methyl methacrylateGenerator
trans-2,3-DimethylacrylateGenerator
trans-2-Methyl-2-butenoateGenerator
trans-2-MethylcrotonateGenerator
trans-a,b-DimethylacrylateGenerator
trans-a,b-Dimethylacrylic acidGenerator
trans-alpha,beta-DimethylacrylateGenerator
trans-Α,β-dimethylacrylateGenerator
trans-Α,β-dimethylacrylic acidGenerator
TiglateGenerator
(2E)-2-Methyl-2-butenoateHMDB
(2E)-2-Methyl-2-butenoic acidHMDB
(e)-2-Methyl-2-butenoateHMDB
(e)-2-Methyl-2-butenoic acidHMDB
(e)-2-Methyl-crotonateHMDB
(e)-2-Methyl-crotonic acidHMDB
2,3-DimethylacrylateHMDB
2,3-Dimethylacrylic acidHMDB
2-Methyl-(e)-2-butenoateHMDB
2-Methyl-(e)-2-butenoic acidHMDB
2-Methyl-2-butenoateHMDB
2-Methyl-2-butenoic acidHMDB
2-Methyl-crotonateHMDB
2-Methyl-crotonic acidHMDB
2-Methylbut-2-enoateHMDB
2-Methylbut-2-enoic acidHMDB
CevadateHMDB
Cevadic acidHMDB
e-TiglateHMDB
e-Tiglic acidHMDB
epsilon-TiglateHMDB
epsilon-Tiglic acidHMDB
MethylbutenoicacidHMDB
TiglinateHMDB
Tiglinic acidHMDB
trans-2-Methylcrotonic acid = trans-2-methyl-2-butenoateHMDB
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
Tiglic acid, (Z)-isomerHMDB
Tiglic acid, (e)-isomerHMDB
(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-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
Crotonic acid, 2-methyl-biospider
Crotonic acid, 2-methyl-, (E)-biospider
E-tiglatebiospider
E-tiglic acidbiospider
Epsilon-tiglatebiospider
Epsilon-tiglic acidbiospider
FEMA 3599db_source
Tiglic aciddb_source
Tiglic acid, (e)-biospider
Tiglic acid, ebiospider
Trans-α,β-dimethylacrylic acidbiospider
trans-2-Methylcrotonic acid = trans-2-Methyl-2-butenoatebiospider
Trans-alpha,beta-dimethylacrylatebiospider
Trans-alpha,beta-dimethylacrylic acidbiospider
trans-α,β-dimethylacrylateGenerator
trans-α,β-dimethylacrylic acidGenerator
Predicted Properties
PropertyValueSource
Water Solubility83 g/LALOGPS
logP1.13ALOGPS
logP1.32ChemAxon
logS-0.08ALOGPS
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
Bioavailability1ChemAxon
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
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 Key
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-0zi0-9000000000-4314e75ba9656b7fb97fView in MoNA
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (1 TMS) - 70eV, Positivesplash10-0ab9-9200000000-1e8cf22de89b50fd327dView in MoNA
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 10V, Negative (Annotated)splash10-0a4j-9000000000-388383b7e67bc9a78b31View in MoNA
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 25V, Negative (Annotated)splash10-052b-9000000000-c5244acf58fff3e4aa88View in MoNA
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 40V, Negative (Annotated)splash10-0002-9000000000-7b12a1fc25be25ecd884View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 10V, Negativesplash10-0002-9000000000-af65ce24e97d441c9c9eView in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 20V, Negativesplash10-052b-9000000000-b48bd344861272ddd921View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 30V, Negativesplash10-0a4i-9000000000-4c3d75c63fc1a2aad554View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 40V, Negativesplash10-001i-9000000000-e71258cb16f06217950bView in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ , negativesplash10-0002-9000000000-af65ce24e97d441c9c9eView in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ , negativesplash10-052b-9000000000-b48bd344861272ddd921View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ , negativesplash10-0a4i-9000000000-4c3d75c63fc1a2aad554View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ , negativesplash10-001i-9000000000-e71258cb16f06217950bView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0ue9-9500000000-9e8414fb7b7ae1c01782View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0a59-9100000000-ad21d817c30785ef1c81View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0a4i-9000000000-fde57dbd7bb552649d7dView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0002-9000000000-1c91e2936e306ff07e44View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0a4j-9000000000-d54eabf82c98dd7ebee8View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0a4i-9000000000-b3098892d6bc4e516906View in MoNA
MSMass Spectrum (Electron Ionization)splash10-0zg0-9100000000-52eb3e4847f5360388c3View in MoNA
1D NMR1H NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR1H NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR13C NMR SpectrumNot AvailableView in JSpectraViewer
2D NMR[1H,13C] 2D NMR SpectrumNot AvailableView in JSpectraViewer
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
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.