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3-Methylbutanal (FDB003285)

Record Information
Version1.0
Creation date2010-04-08 22:05:44 UTC
Update date2020-09-17 15:35:56 UTC
Primary IDFDB003285
Secondary Accession NumbersNot Available
Chemical Information
FooDB Name3-Methylbutanal
DescriptionIsovaleraldehyde, also known as 3-methyl-butanal, belongs to the class of organic compounds known as alpha-hydrogen aldehydes. These are aldehydes with the general formula HC(H)(R)C(=O)H, where R is an organyl group. It exists as a clear colorless or slightly yellow liquid and can be found in essentially all eukaryotes, from yeast to plants to humans. It can be naturally produced through the colonic or microbial breakdown of the amino acid leucine. It can also be generated through the breakdown of leucine in malt (for beer) via reductones. Isovaleraldehyde has been found in elevated concentrations in plasma certain cases of hepatic encephalopathy, however not significantly (PMID: 4038637). Bacteroides (microbial) fermentation of carbohydrates in the gut produces ethanoic, propionic, butanoic, pentanoic, and hexanoic acids leading to the production of aldehydes, such as iosvaleraldehyde (PMID: 17314143, 18275147, 18175918, 16899660). Isovaleraldehyde is found in low amounts in many types of foods including beer, spirits (rum, sake, wine), cheese, coffee, chicken, fish, chocolate, corn tortillas, olive oil and tea. Isovaleraldehyde has also been detected, but not quantified in, several different fruits and nuts, such as muskmelons, highbush blueberries, fenugreeks, hazelnuts, and dills. Isovaleraldehyde has an ethereal, aldehydic chocolate, peach or fatty odor. It exhibits a fruity, nutty, chocolate or cocoa-like taste. As a result, isovaleraldehyde is used as a food additive and as a perfuming or masking agent. Isovaleraldehyde can be produced commercially and is used as a reagent for the production of pharmaceuticals and pesticides. Notably it is used to synthesize pinacolone, which is a precursor for a number of pesticides.
CAS Number590-86-3
Structure
Thumb
MOLSDFPDBSMILESInChI
Synonyms
SynonymSource
Not AvailableNot Available
Predicted Properties
PropertyValueSource
Water Solubility17 g/LALOGPS
logP1.29ALOGPS
logP1.05ChemAxon
logS-0.71ALOGPS
pKa (Strongest Acidic)18.56ChemAxon
pKa (Strongest Basic)-7ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count1ChemAxon
Hydrogen Donor Count0ChemAxon
Polar Surface Area17.07 ŲChemAxon
Rotatable Bond Count2ChemAxon
Refractivity25.49 m³·mol⁻¹ChemAxon
Polarizability10.12 ųChemAxon
Number of Rings0ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterNoChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleNoChemAxon
Chemical FormulaC5H10O
IUPAC name3-methylbutanal
InChI IdentifierInChI=1S/C5H10O/c1-5(2)3-4-6/h4-5H,3H2,1-2H3
InChI KeyYGHRJJRRZDOVPD-UHFFFAOYSA-N
Isomeric SMILESCC(C)CC=O
Average Molecular Weight86.1323
Monoisotopic Molecular Weight86.073164942
Classification
Description Belongs to the class of organic compounds known as alpha-hydrogen aldehydes. These are aldehydes with the general formula HC(H)(R)C(=O)H, where R is an organyl group.
KingdomOrganic compounds
Super ClassOrganic oxygen compounds
ClassOrganooxygen compounds
Sub ClassCarbonyl compounds
Direct ParentAlpha-hydrogen aldehydes
Alternative Parents
Substituents
  • Alpha-hydrogen aldehyde
  • Organic oxide
  • Hydrocarbon derivative
  • Short-chain aldehyde
  • Aliphatic acyclic compound
Molecular FrameworkAliphatic acyclic compounds
External Descriptors
Ontology
Physiological effect

Health effect:

Disposition

Route of exposure:

Biological location:

Source:

Physico-Chemical Properties
Physico-Chemical Properties - Experimental
PropertyValueReference
Physical stateLiquid
Physical DescriptionNot Available
Mass CompositionC 69.72%; H 11.70%; O 18.58%DFC
Melting PointFp -51°DFC
Boiling PointBp 92.5°DFC
Experimental Water Solubility14 mg/mL at 20 oCFALBE,J et al. (1985)
Experimental logPNot Available
Experimental pKaNot Available
Isoelectric pointNot Available
ChargeNot Available
Optical RotationNot Available
Spectroscopic UV DataNot Available
DensityNot Available
Refractive IndexNot Available
Spectra
Spectra
EI-MS/GC-MS
TypeDescriptionSplash KeyView
EI-MSMass Spectrum (Electron Ionization)splash10-0006-9000000000-881fcc89b0f579b407932015-03-01View Spectrum
GC-MS3-Methylbutanal, non-derivatized, GC-MS Spectrumsplash10-0006-9000000000-3a38c8f6150bf1f43e74Spectrum
GC-MS3-Methylbutanal, non-derivatized, GC-MS Spectrumsplash10-0006-9000000000-5a3fd4f38dc36ebe58a1Spectrum
GC-MS3-Methylbutanal, non-derivatized, GC-MS Spectrumsplash10-0006-9000000000-3a38c8f6150bf1f43e74Spectrum
GC-MS3-Methylbutanal, non-derivatized, GC-MS Spectrumsplash10-0006-9000000000-5a3fd4f38dc36ebe58a1Spectrum
Predicted GC-MS3-Methylbutanal, non-derivatized, Predicted GC-MS Spectrum - 70eV, Positivesplash10-0006-9000000000-4b322dc8237378d93057Spectrum
Predicted GC-MS3-Methylbutanal, non-derivatized, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
MS/MS
TypeDescriptionSplash KeyView
MS/MSLC-MS/MS Spectrum - Quattro_QQQ 10V, Positive (Annotated)splash10-000i-9000000000-7f4ac528265c8b3bf3ab2012-07-25View Spectrum
MS/MSLC-MS/MS Spectrum - Quattro_QQQ 25V, Positive (Annotated)splash10-000i-9000000000-6e4f25dc68765a0e52ca2012-07-25View Spectrum
MS/MSLC-MS/MS Spectrum - Quattro_QQQ 40V, Positive (Annotated)splash10-000i-9000000000-809684cd2152204e911f2012-07-25View Spectrum
MS/MSLC-MS/MS Spectrum - EI-B (HITACHI RMU-6M) , Positivesplash10-0006-9000000000-3a38c8f6150bf1f43e742012-08-31View Spectrum
MS/MSLC-MS/MS Spectrum - EI-B (HITACHI RMU-6M) , Positivesplash10-0006-9000000000-5a3fd4f38dc36ebe58a12012-08-31View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-000i-9000000000-a8ed71d6e7d567b598b42015-04-24View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-00kp-9000000000-043451832d2f37b1c7e12015-04-24View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0006-9000000000-3c57d920ca714b174bb32015-04-24View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-000i-9000000000-030536579800c9e499402015-04-25View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-000i-9000000000-be1f1229d7e13994d1502015-04-25View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-00kf-9000000000-13768c049fd8e5c234642015-04-25View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-000i-9000000000-a8ed71d6e7d567b598b42015-05-26View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-00kp-9000000000-043451832d2f37b1c7e12015-05-26View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0006-9000000000-3c57d920ca714b174bb32015-05-26View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-000i-9000000000-030536579800c9e499402015-05-27View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-000i-9000000000-be1f1229d7e13994d1502015-05-27View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-00kf-9000000000-13768c049fd8e5c234642015-05-27View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-000i-9000000000-2091e44a102d8284a8132021-09-22View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-000i-9000000000-199420ebca1b5eda63692021-09-22View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0006-9000000000-0f801351f709d0e5abf62021-09-22View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0006-9000000000-fead34b12404197f107d2021-09-25View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0006-9000000000-cf72963a4f1f9f7f2df02021-09-25View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0006-9000000000-cd0a0aa8e74bbc2b63442021-09-25View Spectrum
NMR
TypeDescriptionView
1D NMR1H NMR Spectrum (1D, 600 MHz, H2O, experimental)Spectrum
1D NMR1H NMR Spectrum (1D, 400 MHz, CDCl3, experimental)Spectrum
1D NMR13C NMR Spectrum (1D, 25.16 MHz, CDCl3, experimental)Spectrum
1D NMR1H NMR Spectrum (1D, 100 MHz, D2O, predicted)Spectrum
1D NMR13C NMR Spectrum (1D, 100 MHz, D2O, predicted)Spectrum
1D NMR1H NMR Spectrum (1D, 1000 MHz, D2O, predicted)Spectrum
1D NMR13C NMR Spectrum (1D, 1000 MHz, D2O, predicted)Spectrum
1D NMR1H NMR Spectrum (1D, 200 MHz, D2O, predicted)Spectrum
1D NMR13C NMR Spectrum (1D, 200 MHz, D2O, predicted)Spectrum
1D NMR1H NMR Spectrum (1D, 300 MHz, D2O, predicted)Spectrum
1D NMR13C NMR Spectrum (1D, 300 MHz, D2O, predicted)Spectrum
1D NMR1H NMR Spectrum (1D, 400 MHz, D2O, predicted)Spectrum
1D NMR13C NMR Spectrum (1D, 400 MHz, D2O, predicted)Spectrum
1D NMR1H NMR Spectrum (1D, 500 MHz, D2O, predicted)Spectrum
1D NMR13C NMR Spectrum (1D, 500 MHz, D2O, predicted)Spectrum
1D NMR1H NMR Spectrum (1D, 600 MHz, D2O, predicted)Spectrum
1D NMR13C NMR Spectrum (1D, 600 MHz, D2O, predicted)Spectrum
1D NMR1H NMR Spectrum (1D, 700 MHz, D2O, predicted)Spectrum
1D NMR13C NMR Spectrum (1D, 700 MHz, D2O, predicted)Spectrum
1D NMR1H NMR Spectrum (1D, 800 MHz, D2O, predicted)Spectrum
1D NMR13C NMR Spectrum (1D, 800 MHz, D2O, predicted)Spectrum
1D NMR1H NMR Spectrum (1D, 900 MHz, D2O, predicted)Spectrum
1D NMR13C NMR Spectrum (1D, 900 MHz, D2O, predicted)Spectrum
1D NMR1H NMR Spectrum (1D, 600 MHz, H2O, experimental)Spectrum
2D NMR[1H, 13C]-HSQC NMR Spectrum (2D, 600 MHz, H2O, experimental)Spectrum
ChemSpider ID11065
ChEMBL IDCHEMBL18360
KEGG Compound IDC07329
Pubchem Compound ID11552
Pubchem Substance IDNot Available
ChEBI ID16638
Phenol-Explorer IDNot Available
DrugBank IDNot Available
HMDB IDHMDB06478
CRC / DFC (Dictionary of Food Compounds) IDCVM54-L:CVM54-L
EAFUS ID2285
Dr. Duke ID3-METHYL-BUTAN-1-AL|3-METHYL-BUTANAL|ISOVALERALDEHYDE|BUTANAL-3-METHYL|3-METHYL-BUTYRALDEHYDE
BIGG IDNot Available
KNApSAcK IDNot Available
HET IDNot Available
Food Biomarker OntologyNot Available
VMH IDNot Available
Flavornet ID590-86-3
GoodScent IDrw1023131
SuperScent ID11552
Wikipedia IDNot Available
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
flavor48318 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
malt
  1. Arn, H, Acree TE. “Flavornet: A database of aroma compounds based on odor potency in natural products”. Developments in Food Science 40 (1998): 27. doi:10.1016/S0167-4501(98)80029-0
sour
  1. Dunkel, M. et al. SuperScent – a database of flavors and scents. Nucleic Acids Research 2008, doi:10.1093/nar/gkn695
ethereal
  1. The Good Scents Company (2009). Flavor and fragrance information catalog. <http://www.thegoodscentscompany.com/allprod.html> Accessed 15.10.23.
aldehydic
  1. The Good Scents Company (2009). Flavor and fragrance information catalog. <http://www.thegoodscentscompany.com/allprod.html> Accessed 15.10.23.
chocolate
  1. The Good Scents Company (2009). Flavor and fragrance information catalog. <http://www.thegoodscentscompany.com/allprod.html> Accessed 15.10.23.
peach
  1. The Good Scents Company (2009). Flavor and fragrance information catalog. <http://www.thegoodscentscompany.com/allprod.html> Accessed 15.10.23.
fatty
  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).