Record Information
Version1.0
Creation date2015-10-09 22:33:15 UTC
Update date2017-01-19 02:36:40 UTC
FoodComEx IDPC000895
FoodDB RecordFDB003285
Chemical Information
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
Synonyms
SynonymSource
β-methylbutanalbiospider
1-Butanal, 3-methyl-biospider
2-Methylbutanal-4biospider
3-Methyl butyraldehydebiospider
3-methyl-1-Butanalbiospider
3-methyl-Butanalbiospider
3-methyl-Butyraldehydebiospider
3-Methylbutan-1-albiospider
3-Methylbutylaldehydebiospider
3-Methylbutyraldehydedb_source
Aldehyde isovalerianiquebiospider
B-methylbutanalbiospider
Beta-methylbutanalbiospider
Beta-methylbutyraldehydebiospider
Butanal, 3-methyl-biospider
Butanal, methyl-biospider
Butyraldehyde, 3-methyl-biospider
FEMA 2692db_source
iso-C4H9CHObiospider
Isoamyl aldehydebiospider
Isoamylaldehydebiospider
Isopentaldehydebiospider
Isopentanalbiospider
Isovaleralbiospider
Isovaleraldehydedb_source
ISOVALERALDEHYDE, B.P.91-93<F128><144><F255>biospider
Isovaleraldehyde,techbiospider
Isovaleric aldehydebiospider
Isovalerylaldehydebiospider
Methyl butanalbiospider
β-methylbutanalGenerator
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
Chemical Taxonomy
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
Physico-Chemical Properties - Experimental
PropertyValueReference
Experimental logPNot Available
Experimental Water Solubility14 mg/mL at 20 oCFALBE,J et al. (1985)
Melting PointFp -51°DFC
Foods of Origin
FoodContent Range AverageReference
FoodReference
Production Data
Production Methodcommercial
Production Method ReferenceNot Available
Production Method Reference FileNot Available
Quantity AvailableProduction upon request, up to 3 g
Delivery TimeNot Available
Storage Formliquid
Storage Conditions-80°C
StabilityNot Available
PurityNot Available
Spectra
Spectral Data Upon RequestNot Available
Provider Information
Contact NameContact InstitutionContact Email
Rosa Vazquez Fresnovazquezf@ualberta.ca
Commercial Vendors
Alfa Aesar HMDB0006478
MetaSci HMDB0006478
Toronto Research Chemicals V091300