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Record Information
Version3.6
Creation Date2005-11-16 15:48:42 UTC
Update Date2016-02-11 01:04:45 UTC
HMDB IDHMDB01470
Secondary Accession NumbersNone
Metabolite Identification
Common NameTiglic acid
DescriptionTiglic acid is a thick, syrupy poisonous liquid, C5H8O2, derived from croton oil, having a spicy odor and used in making perfumes and flavoring agents.
Structure
Thumb
Synonyms
ValueSource
(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
TiglateGenerator
(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
(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
Chemical FormulaC5H8O2
Average Molecular Weight100.1158
Monoisotopic Molecular Weight100.0524295
IUPAC Name(2E)-2-methylbut-2-enoic acid
Traditional Nametiglic acid
CAS Registry Number80-59-1
SMILES
C\C=C(/C)C(O)=O
InChI Identifier
InChI=1S/C5H8O2/c1-3-4(2)5(6)7/h3H,1-2H3,(H,6,7)/b4-3+
InChI KeyInChIKey=UIERETOOQGIECD-ONEGZZNKSA-N
Chemical Taxonomy
DescriptionThis compound 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
  • Hydrocarbon derivative
  • Organooxygen compound
  • Carbonyl group
  • Aliphatic acyclic compound
Molecular FrameworkAliphatic acyclic compounds
External Descriptors
Ontology
StatusExpected but not Quantified
Origin
  • Endogenous
  • Food
Biofunction
  • Cell signaling
  • Fuel and energy storage
  • Fuel or energy source
  • Membrane integrity/stability
Application
  • Nutrients
  • Stabilizers
  • Surfactants and Emulsifiers
Cellular locations
  • Extracellular
  • Membrane
Physical Properties
StateLiquid
Experimental Properties
PropertyValueReference
Melting Point61 - 65 °CNot Available
Boiling PointNot AvailableNot Available
Water Solubility1 mg/mLNot Available
LogPNot AvailableNot Available
Predicted Properties
PropertyValueSource
Water Solubility83.0 mg/mLALOGPS
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 Å2ChemAxon
Rotatable Bond Count1ChemAxon
Refractivity27.32 m3·mol-1ChemAxon
Polarizability10.39 Å3ChemAxon
Number of Rings0ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Spectra
Spectra
Spectrum TypeDescriptionSplash Key
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
MSMass Spectrum (Electron Ionization)splash10-0zg0-9100000000-52eb3e4847f5360388c3View in MoNA
1D NMR1H NMR SpectrumNot Available
1D NMR1H NMR SpectrumNot Available
1D NMR13C NMR SpectrumNot Available
2D NMR[1H,13C] 2D NMR SpectrumNot Available
Biological Properties
Cellular Locations
  • Extracellular
  • Membrane
Biofluid LocationsNot Available
Tissue LocationNot Available
PathwaysNot Available
Normal Concentrations
Not Available
Abnormal Concentrations
Not Available
Associated Disorders and Diseases
Disease ReferencesNone
Associated OMIM IDsNone
DrugBank IDNot Available
DrugBank Metabolite IDNot Available
Phenol Explorer Compound IDNot Available
Phenol Explorer Metabolite IDNot Available
FoodDB IDFDB000774
KNApSAcK IDC00001207
Chemspider ID111629
KEGG Compound IDC08279
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkTiglic acid
NuGOwiki LinkHMDB01470
Metagene LinkHMDB01470
METLIN ID6261
PubChem Compound125468
PDB IDNot Available
ChEBI ID9592
References
Synthesis ReferenceJacob, Carl; Hafner, Walter; Wick, Manfred. Tiglic acid. Ger. Offen. (1976), 6 pp.
Material Safety Data Sheet (MSDS)Download (PDF)
General ReferencesNot Available