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Butanoic acid (PC000018)

Record Information
Version1.0
Creation date2015-10-09 22:27:21 UTC
Update date2017-01-19 02:36:10 UTC
FoodComEx IDPC000018
FoodDB RecordFDB012062
Chemical Information
NameButanoic acid
DescriptionFound in fresh and cooked apples, banana, sour cherry, papaya, strawberries, wheat bread, cheeses, butter and coffee. Flavouring agent Butyric acid (from Greek ???????? = butter), also known under the systematic name butanoic acid, is a carboxylic acid with the structural formula CH3CH2CH2-COOH. Salts and esters of butyric acid are known as butyrates or butanoates. Butyric acid is found in rancid butter, parmesan cheese, vomit, and body odor and has an unpleasant smell and acrid taste, with a sweetish aftertaste (similar to ether). It can be detected by mammals with good scent detection abilities (such as dogs) at 10 ppb, whereas humans can detect it in concentrations above 10 ppm.; Butyric acid is a fatty acid occurring in the form of esters in animal fats and plant oils. The triglyceride of butyric acid makes up 3% to 4% of butter. When butter goes rancid, butyric acid is liberated from the glyceride by hydrolysis leading to the unpleasant odor. It is an important member of the fatty acid sub-group called short chain fatty acids. Butyric acid is a weak acid with a pKa of 4.82, similar to acetic acid which has pKa 4.76. The similar strength of these acids results from their common -CH2COOH terminal structure. Pure butyric acid is 10.9 molar.; Butyric acid, a four-carbon fatty acid, is formed in the human colon by bacterial fermentation of carbohydrates (including dietary fiber), and putatively suppresses colorectal cancer (CRC). Butyrate has diverse and apparently paradoxical effects on cellular proliferation, apoptosis and differentiation that may be either pro-neoplastic or anti-neoplastic, depending upon factors such as the level of exposure, availability of other metabolic substrate and the intracellular milieu. In humans, the relationship between luminal butyrate exposure and CRC has been examined only indirectly in case-control studies, by measuring fecal butyrate concentrations, although this may not accurately reflect effective butyrate exposure during carcinogenesis. Perhaps not surprisingly, results of these investigations have been mutually contradictory. The direct effect of butyrate on tumorigenesis has been assessed in a no. of in vivo animal models, which have also yielded conflicting results. In part, this may be explained by methodology: differences in the amount and route of butyrate administration, which are likely to significantly influence delivery of butyrate to the distal colon. (PMID: 16460475) Butyric acid is a carboxylic acid found in rancid butter, parmesan cheese, and vomit, and has an unpleasant odor and acrid taste, with a sweetish aftertaste (similar to ether). Butyric acid is a fatty acid occurring in the form of esters in animal fats and plant oils. Interestingly, low-molecular-weight esters of butyric acid, such as methyl butyrate, have mostly pleasant aromas or tastes. As a consequence, they find use as food and perfume additives. Butyrate is produced as end-product of a fermentation process solely performed by obligate anaerobic bacteria.; The acid is an oily colorless liquid that is easily soluble in water, ethanol, and ether, and can be separated from an aqueous phase by saturation with salts such as calcium chloride. Potassium dichromate and sulfuric acid oxidize it to carbon dioxide and acetic acid, while alkaline potassium permanganate oxidizes it to carbon dioxide. The calcium salt, Ca(C4H7O2)2·H2O, is less soluble in hot water than in cold.
CAS Number107-92-6
Structure
Thumb
MOLSDFPDBSMILESInChI
Synonyms
SynonymSource
1-butanoatebiospider
1-butanoic acidbiospider
1-Butyratebiospider
1-Butyric acidbiospider
1-Propanecarboxylatebiospider
1-Propanecarboxylic acidbiospider
1ugpbiospider
2-butanoatebiospider
4:0ChEBI
Acid, butanoicbiospider
Acid, butyricbiospider
Acide butanoiqueChEBI
Acide butyriqueChEBI
BEObiospider
BUAbiospider
Butanatebiospider
Butanic acidbiospider
Butanoatebiospider
butanoic acid, 4biospider
ButoateGenerator
Butoic acidbiospider
ButtersaeureChEBI
Butyratebiospider
Butyrate (n-C4:0)biospider
Butyrate, sodium saltbiospider
Butyric aciddb_source
Butyric acid [UN2820] [Corrosive]biospider
Butyric_acidbiospider
C4:0ChEBI
CH3-[CH2]2-COOHbiospider
Ethyacetic acidbiospider
EthylacetateGenerator
Ethylacetic acidbiospider
FEMA 2221db_source
Honey robberbiospider
Kyselina maselnaHMDB
N-butanoatebiospider
N-butanoic acidbiospider
N-butyratebiospider
N-butyric acidbiospider
n-C3H7COOHbiospider
Propanecarboxylatebiospider
Propanecarboxylic acidbiospider
Propylformatebiospider
Propylformic acidbiospider
Chemical FormulaC4H8O2
IUPAC namebutanoic acid
InChI IdentifierInChI=1S/C4H8O2/c1-2-3-4(5)6/h2-3H2,1H3,(H,5,6)
InChI KeyFERIUCNNQQJTOY-UHFFFAOYSA-N
Isomeric SMILESCCCC(O)=O
Average Molecular Weight88.1051
Monoisotopic Molecular Weight88.0524295
Chemical Taxonomy
Description Belongs to the class of organic compounds known as straight chain fatty acids. These are fatty acids with a straight aliphatic chain.
KingdomOrganic compounds
Super ClassLipids and lipid-like molecules
ClassFatty Acyls
Sub ClassFatty acids and conjugates
Direct ParentStraight chain fatty acids
Alternative Parents
Substituents
  • Straight chain fatty acid
  • Monocarboxylic acid or derivatives
  • Carboxylic acid
  • Carboxylic acid derivative
  • Organic oxygen compound
  • Organic oxide
  • Hydrocarbon derivative
  • Organooxygen compound
  • Carbonyl group
  • Aliphatic acyclic compound
Molecular FrameworkAliphatic acyclic compounds
External Descriptors
Physico-Chemical Properties - Experimental
PropertyValueReference
Experimental logP0.79HANSCH,C ET AL. (1995)
Experimental Water Solubility60 mg/mL at 25 oCHEMPHILL,L & SWANSON,WS (1964)
Melting PointMp -8°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 2 g
Delivery TimeNot Available
Storage Formsolid
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
AKSci V2319
Toronto Research Chemicals B692235