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Record Information
Version4.0
StatusDetected but not Quantified
Creation Date2012-09-11 17:43:45 UTC
Update Date2019-07-23 06:08:55 UTC
HMDB IDHMDB0031512
Secondary Accession Numbers
  • HMDB31512
Metabolite Identification
Common NameTiglic aldehyde
DescriptionTiglic aldehyde, also known as CH3CH=c(CH3)cho or fema 3407, belongs to the class of organic compounds known as enals. These are an alpha,beta-unsaturated aldehyde of general formula RC=C-CH=O in which the aldehydic C=O function is conjugated to a C=C triple bond at the alpha,beta position. Tiglic aldehyde is an extremely weak basic (essentially neutral) compound (based on its pKa). Tiglic aldehyde is a strong, fruit, and green tasting compound. Outside of the human body, Tiglic aldehyde is found, on average, in the highest concentration within safflowers. Tiglic aldehyde has also been detected, but not quantified in, several different foods, such as herbs and spices, onion-family vegetables, citrus, garden tomato (var.), and cherry tomato. This could make tiglic aldehyde a potential biomarker for the consumption of these foods. This colorless liquid is a building block in organic synthesis. It is an α,β-unsaturated aldehyde related to the better-known crotonaldehyde. trans-2-Methyl-2-butenal is an organic compound with the formula CH3CHC(CH3)CHO. The European rabbit, Oryctolagus cuniculus, uses 2-methyl-2-butenal as a pheromone.
Structure
Data?1563862135
Synonyms
ValueSource
(2E)-2-Methyl-2-butenalHMDB
(e)-2-Methyl-2-butenalHMDB
(e)-2-Methylbut-2-en-1-alHMDB
(e)-2-Methylbut-2-enalHMDB
(e)-2-MethylcrotonaldehydeHMDB
2-Methyl-(2E)-2-butenalHMDB
2-Methyl-(e)-2-butenalHMDB
2-Methyl-(e)-crotonaldehydeHMDB
2-Methyl-2(e)-butenalHMDB
2-Methyl-2-butenalHMDB
2-Methyl-2-butenal, (e)HMDB
2-Methyl-2-butenal, transHMDB
2-Methyl-crotonaldehydeHMDB
2-Methylbut-(e)-2-enalHMDB
CH3CH=C(CH3)choHMDB
Crotonaldehyde, 2-methyl-, (e)- (8ci)HMDB
e-2-Methyl-2-butenalHMDB
FEMA 3407HMDB
TiglaldehydeHMDB
Tiglaldehyde (2-methyl-2-butenal)HMDB
Tiglic acid aldehydeHMDB
TiglinaldehydeHMDB
trans-2,3-DimethylacroleinHMDB
trans-2-Methyl-2-butenalHMDB
trans-2-MethylcrotonaldehydeHMDB
trans-TigaldehydeHMDB
trans-TiglaldehydeHMDB
2-Methylbut-2-enalMeSH
Chemical FormulaC5H8O
Average Molecular Weight84.1164
Monoisotopic Molecular Weight84.057514878
IUPAC Name(2Z)-2-methylbut-2-enal
Traditional Name(2Z)-2-methylbut-2-enal
CAS Registry Number497-03-0
SMILES
C\C=C(\C)C=O
InChI Identifier
InChI=1S/C5H8O/c1-3-5(2)4-6/h3-4H,1-2H3/b5-3-
InChI KeyACWQBUSCFPJUPN-HYXAFXHYSA-N
Chemical Taxonomy
Description belongs to the class of organic compounds known as enals. These are an alpha,beta-unsaturated aldehyde of general formula RC=C-CH=O in which the aldehydic C=O function is conjugated to a C=C triple bond at the alpha,beta position.
KingdomOrganic compounds
Super ClassOrganic oxygen compounds
ClassOrganooxygen compounds
Sub ClassCarbonyl compounds
Direct ParentEnals
Alternative Parents
Substituents
  • Enal
  • Organic oxide
  • Hydrocarbon derivative
  • Short-chain aldehyde
  • Aldehyde
  • Aliphatic acyclic compound
Molecular FrameworkAliphatic acyclic compounds
External DescriptorsNot Available
Ontology
Disposition

Route of exposure:

Source:

Biological location:

Process

Naturally occurring process:

Role

Industrial application:

Biological role:

Physical Properties
StateNot Available
Experimental Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water Solubility25 mg/mLNot Available
LogPNot AvailableNot Available
Predicted Properties
PropertyValueSource
Water Solubility40.6 g/LALOGPS
logP0.93ALOGPS
logP1.16ChemAxon
logS-0.32ALOGPS
pKa (Strongest Basic)-4ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count1ChemAxon
Hydrogen Donor Count0ChemAxon
Polar Surface Area17.07 ŲChemAxon
Rotatable Bond Count1ChemAxon
Refractivity26.4 m³·mol⁻¹ChemAxon
Polarizability9.49 ųChemAxon
Number of Rings0ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterNoChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleNoChemAxon
Spectra
Spectrum TypeDescriptionSplash KeyView
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-05q9-9000000000-c55d49861ee6b1113cf9Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-000i-9000000000-1e63e408fa4731465f7dSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-000i-9000000000-840489df070350dbd21aSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0pb9-9000000000-967f72345ff4e63b646fSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-001i-9000000000-07023e058e96a5079ecaSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0a59-9000000000-8c33b9aae6f9f2e3d24aSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0a4i-9000000000-073297c5c61a3fcdc6feSpectrum
Biological Properties
Cellular Locations
  • Cytoplasm
  • Extracellular
  • Membrane
Biospecimen Locations
  • Feces
  • Saliva
Tissue LocationsNot Available
Pathways
Normal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
FecesDetected but not Quantified Adult (>18 years old)Both
Normal
details
SalivaDetected but not Quantified Adult (>18 years old)Not SpecifiedNormal details
Abnormal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
FecesDetected but not Quantified Adult (>18 years old)Both
Campylobacter jejuni infection
details
FecesDetected but not Quantified Adult (>18 years old)Both
Clostridium difficile infection
details
Associated Disorders and Diseases
Disease ReferencesNone
Associated OMIM IDsNone
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FooDB IDFDB008105
KNApSAcK IDNot Available
Chemspider ID4784283
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkTrans-2-Methyl-2-butenal
METLIN IDNot Available
PubChem Compound6028462
PDB IDNot Available
ChEBI ID88419
Food Biomarker OntologyNot Available
VMH IDNot Available
References
Synthesis ReferenceNot Available
Material Safety Data Sheet (MSDS)Not Available
General References
  1. (). Yannai, Shmuel. (2004) Dictionary of food compounds with CD-ROM: Additives, flavors, and ingredients. Boca Raton: Chapman & Hall/CRC.. .