2-Propenyl 3-methylbutanoate (T3D3231)

IdentificationTaxonomyBiological PropertiesPhysical PropertiesToxicity ProfileSpectraConcentrationsLinksReferencesGene RegulationXML
Record Information
Version2.0
Creation Date2009-07-30 17:56:36 UTC
Update Date2014-12-24 20:26:01 UTC
Accession NumberT3D3231
Identification
Common Name2-Propenyl 3-methylbutanoate
ClassSmall Molecule
Description2-Propenyl 3-methylbutanoate is a flavouring ingredient.
Compound Type
  • Ester
  • Ether
  • Food Toxin
  • Fragrance Toxin
  • Household Toxin
  • Metabolite
  • Organic Compound
  • Synthetic Compound
Chemical Structure
Thumb
MOLSDFPDBSMILESInChI
Synonyms
Synonym
2-Propenyl 3-methylbutanoic acid
2-Propenyl isopentanoate
2-Propenyl isovalerate
3-Methylbutanoic acid, 2-propenyl ester
3-Methylbutyric acid, allyl ester
Allyl 3-methylbutanoate
Allyl 3-methylbutyrate
Allyl isopentanoate
Allyl isovalerate
Allyl isovalerianate
Allylisovalerate
Butanoic acid, 3-methyl-, 2-propen-1-yl ester
Butanoic acid, 3-methyl-, 2-propenyl ester
Butyric acid, 3-methyl-, allyl ester
Isovaleric acid, allyl ester
Chemical FormulaC8H14O2
Average Molecular Mass142.196 g/mol
Monoisotopic Mass142.099 g/mol
CAS Registry Number2835-39-4
IUPAC Nameprop-2-en-1-yl 3-methylbutanoate
Traditional Nameallyl isovalerate
SMILESCC(C)CC(=O)OCC=C
InChI IdentifierInChI=1S/C8H14O2/c1-4-5-10-8(9)6-7(2)3/h4,7H,1,5-6H2,2-3H3
InChI KeyInChIKey=HOMAGVUCNZNWBC-UHFFFAOYSA-N
Chemical Taxonomy
Description belongs to the class of organic compounds known as fatty acid esters. These are carboxylic ester derivatives of a fatty acid.
KingdomOrganic compounds
Super ClassLipids and lipid-like molecules
ClassFatty Acyls
Sub ClassFatty acid esters
Direct ParentFatty acid esters
Alternative Parents
Substituents
  • Fatty acid ester
  • Carboxylic acid ester
  • Monocarboxylic acid or derivatives
  • Carboxylic acid derivative
  • Organic oxygen compound
  • Organic oxide
  • Hydrocarbon derivative
  • Organooxygen compound
  • Carbonyl group
  • Aliphatic acyclic compound
Molecular FrameworkAliphatic acyclic compounds
External Descriptors
Biological Properties
StatusDetected and Not Quantified
OriginExogenous
Cellular Locations
  • Cytoplasm
  • Extracellular
  • Membrane
Biofluid LocationsNot Available
Tissue LocationsNot Available
PathwaysNot Available
ApplicationsNot Available
Biological RolesNot Available
Chemical RolesNot Available
Physical Properties
StateLiquid
AppearanceColorless to pale yellow clear liquid (3).
Experimental Properties
PropertyValue
Melting PointNot Available
Boiling PointNot Available
SolubilityNot Available
LogPNot Available
Predicted Properties
PropertyValueSource
Water Solubility3.31 g/LALOGPS
logP2.43ALOGPS
logP2.09ChemAxon
logS-1.6ALOGPS
pKa (Strongest Basic)-7ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count1ChemAxon
Hydrogen Donor Count0ChemAxon
Polar Surface Area26.3 ŲChemAxon
Rotatable Bond Count5ChemAxon
Refractivity40.35 m³·mol⁻¹ChemAxon
Polarizability16.15 ųChemAxon
Number of Rings0ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Spectra
Spectra
Spectrum TypeDescriptionSplash KeyDeposition DateView
GC-MSGC-MS Spectrum - EI-B (Non-derivatized)splash10-052u-9000000000-7354044a3e73badab5472017-09-12View Spectrum
GC-MSGC-MS Spectrum - EI-B (Non-derivatized)splash10-052u-9000000000-7354044a3e73badab5472018-05-18View Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-052f-9100000000-8c72ffff21927ecdaed82017-09-01View Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, PositiveNot Available2021-10-12View Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0006-9800000000-c1c58cf36f0fc42f665d2016-08-03View Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0006-9000000000-79d35f58be29e09f9c342016-08-03View Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-052f-9000000000-79e7855d5c6b4384458a2016-08-03View Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-000x-9800000000-2050888b2f1aa71760e12016-08-03View Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0zgi-9500000000-62023d4b0cc8031ce8002016-08-03View Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0a5i-9000000000-74d59f47280519a970b82016-08-03View Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0a4i-9100000000-9581f7dd0f1122c0bce52021-09-23View Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0a4i-9200000000-b681809035a0144971572021-09-23View Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-053r-9100000000-bfa8683a2fd26729f60e2021-09-23View Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0f7c-9500000000-5ccc91bfcd244fb824452021-09-25View Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-052f-9000000000-3546ef42470e2cefd6112021-09-25View Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-052f-9000000000-5bb1bf863e5ad8e0b7272021-09-25View Spectrum
MSMass Spectrum (Electron Ionization)splash10-0a4u-9000000000-144259e1f020cb7f39b72014-09-20View Spectrum
1D NMR1H NMR Spectrum (1D, 90 MHz, CDCl3, experimental)Not Available2014-09-20View Spectrum
1D NMR13C NMR Spectrum (1D, 15.09 MHz, CDCl3, experimental)Not Available2014-09-23View Spectrum
1D NMR1H NMR Spectrum (1D, 100 MHz, D2O, predicted)Not Available2021-09-24View Spectrum
1D NMR13C NMR Spectrum (1D, 100 MHz, D2O, predicted)Not Available2021-09-24View Spectrum
1D NMR1H NMR Spectrum (1D, 1000 MHz, D2O, predicted)Not Available2021-09-24View Spectrum
1D NMR13C NMR Spectrum (1D, 1000 MHz, D2O, predicted)Not Available2021-09-24View Spectrum
1D NMR1H NMR Spectrum (1D, 200 MHz, D2O, predicted)Not Available2021-09-24View Spectrum
1D NMR13C NMR Spectrum (1D, 200 MHz, D2O, predicted)Not Available2021-09-24View Spectrum
1D NMR1H NMR Spectrum (1D, 300 MHz, D2O, predicted)Not Available2021-09-24View Spectrum
1D NMR13C NMR Spectrum (1D, 300 MHz, D2O, predicted)Not Available2021-09-24View Spectrum
1D NMR1H NMR Spectrum (1D, 400 MHz, D2O, predicted)Not Available2021-09-24View Spectrum
1D NMR13C NMR Spectrum (1D, 400 MHz, D2O, predicted)Not Available2021-09-24View Spectrum
1D NMR1H NMR Spectrum (1D, 500 MHz, D2O, predicted)Not Available2021-09-24View Spectrum
1D NMR13C NMR Spectrum (1D, 500 MHz, D2O, predicted)Not Available2021-09-24View Spectrum
1D NMR1H NMR Spectrum (1D, 600 MHz, D2O, predicted)Not Available2021-09-24View Spectrum
1D NMR13C NMR Spectrum (1D, 600 MHz, D2O, predicted)Not Available2021-09-24View Spectrum
1D NMR1H NMR Spectrum (1D, 700 MHz, D2O, predicted)Not Available2021-09-24View Spectrum
1D NMR13C NMR Spectrum (1D, 700 MHz, D2O, predicted)Not Available2021-09-24View Spectrum
1D NMR1H NMR Spectrum (1D, 800 MHz, D2O, predicted)Not Available2021-09-24View Spectrum
1D NMR13C NMR Spectrum (1D, 800 MHz, D2O, predicted)Not Available2021-09-24View Spectrum
1D NMR1H NMR Spectrum (1D, 900 MHz, D2O, predicted)Not Available2021-09-24View Spectrum
1D NMR13C NMR Spectrum (1D, 900 MHz, D2O, predicted)Not Available2021-09-24View Spectrum
Toxicity Profile
Route of ExposureNot Available
Mechanism of ToxicityAllyl isovalerate has low irritancy potential. It is deduced that one of its metabolites, isovaleric acid, is toxic, based upon the effects of an inborn error of leucine metabolism caused by isovaleryl-coenzyme A dehydrogenase deficiency (4).
MetabolismAllyl isovalerate is metabolized to isovaleric acid, which can conjugate with glycine, and allyl alcohol, which could then be further metabolized via two pathways to form either acrolein or glycidol, from which a variety of metabolites could result (4).
Toxicity ValuesLD50: 230 mg/kg (Oral, Rat) (3) LD50: 500 mg/kg (Oral, Mouse) (3) LD50: 560 mg/kg (Dermal, Rabbit) (3)
Lethal DoseNot Available
Carcinogenicity (IARC Classification)3, not classifiable as to its carcinogenicity to humans. (5)
Uses/SourcesAllyl isovalerate has been used since the 1950s as a raw material for fragrances in cosmetics, lotions and perfumes and in certain food products, although it is not known whether it is currently used in this way (4).
Minimum Risk LevelNot Available
Health EffectsHarmful in contact with skin and if swallowed. Exposure via inhalation may result in bronchospasm and rarely, upper airway swelling or acute lung injury (1, 3).
SymptomsIrritating to eyes, respiratory system, and skin. Headache, rhinorrhea, cough, shortness of breath, chest pain (3).
TreatmentConsider dilution with water or milk in case of ingestion. After inhalation, move patient to fresh air and monitor for respiratory distress. In case of eye exposure, irrigate exposed eyes with copious amounts of room temperature water for at least 15 minutes. (1)
Normal Concentrations
Not Available
Abnormal Concentrations
Not Available
DrugBank IDNot Available
HMDB IDHMDB38036
PubChem Compound ID17816
ChEMBL IDCHEMBL1887355
ChemSpider ID16835
KEGG IDC19318
UniProt IDNot Available
OMIM ID
ChEBI IDNot Available
BioCyc ID2-KETO-ISOVALERATE
CTD IDNot Available
Stitch IDAllyl isovalerate
PDB IDNot Available
ACToR IDNot Available
Wikipedia LinkNot Available
References
Synthesis ReferenceNot Available
MSDSNot Available
General References
  1. Rumack BH (2009). POISINDEX(R) Information System. Englewood, CO: Micromedex, Inc. CCIS Volume 141, edition expires Aug, 2009.
  2. Yannai, Shmuel. (2004) Dictionary of food compounds with CD-ROM: Additives, flavors, and ingredients. Boca Raton: Chapman & Hall/CRC.
  3. The Good Scents Company (2009). Material Safety Data Sheet for Allyl isovalerate. [Link]
  4. IARC (1985). Monograph of Allyl Isovalerate. [Link]
  5. International Agency for Research on Cancer (2014). IARC Monographs on the Evaluation of Carcinogenic Risks to Humans. [Link]
Gene Regulation
Up-Regulated GenesNot Available
Down-Regulated GenesNot Available