Butanoic acid

Butanoic acid
Compound Structure:
Synonyms: butyric acid;butanoic acid;107-92-6;n-Butyric acid;n-Butanoic acid;propylformic acid;ethylacetic acid;1-propanecarboxylic acid;Butyrate;Butanic acid;1-Butyric acid;Buttersaeure;butanoate;Butyric acid (natural);Kyselina maselna
Compound ID: NMPC-693
PubChem ID:

264

Molecular Formula: C4H8O2
Canonical SMILES: CCCC(=O)O
InChIKey: FERIUCNNQQJTOY-UHFFFAOYSA-N
About the compound:

Butyric acid, also known as butanoic acid, is a straight-chain saturated fatty acid. Its structure consists of a butane backbone where one of the terminal methyl groups is oxidized to a carboxy group. Chemically represented as CH3CH2CH2CO2H, butyric acid is an oily, colorless liquid known for its unpleasant odor. It plays a role as a metabolite in Mycoplasma genitalium and is also found in human urine. Structurally, it's a straight-chain saturated fatty acid and falls under the category of fatty acids with a 4-carbon chain (fatty acid 4:0). In its ionic form, it is referred to as butyrate or butanoate. Butyric acid is naturally present in butter and animal fat in the form of glycerol esters. The term 'butyric' comes from the Ancient Greek word "βούτῡρον", meaning "butter". Although it is not widely found in its free form in nature, its esters are commonly distributed. It is an isomer of isobutyric acid (2-methylpropanoic acid) and is an important chemical in both industrial and biological contexts. In industry, butyric acid is used to produce various butyrate esters. One significant application is in the production of cellulose acetate butyrate (CAB), which is used in a range of tools, paints, and coatings. CAB is more resistant to degradation compared to cellulose acetate, but it can still degrade under heat and moisture, releasing butyric acid. The lower molecular weight esters of butyric acid, like methyl butyrate, typically have pleasant aromas or tastes. As a result, they are frequently used as additives in food and perfumes. In the European Union, it is an approved food flavoring, listed under the FLAVIS number 08.005. Butyric acid has also found an unusual use as a fishing bait additive, particularly in carp baits, due to its strong odor. While it's unclear whether fish are attracted to butyric acid itself or the substances added to it, it has been noted for its palatability to certain fish species like tench and bitterling. Additionally, butyric acid has been employed as a stink bomb by environmental groups, such as the Sea Shepherd Conservation Society, to disrupt activities they oppose, like whaling. Its diverse applications, ranging from industrial uses in paints and coatings to its role in food flavorings and even in environmental activism, highlight the versatility and significance of butyric acid in various fields. Despite its unpleasant odor, its chemical properties make it a valuable compound in many different contexts.

GHS Hazard Statements

H314: Causes severe skin burns and eye damage [Danger Skin corrosion/irritation]

Properties:

Chemical and Physical Properties

Property Name

Property Value

Molecular Weight

88.11 g/mol

XLogP3

0.8

Hydrogen Bond Donor Count

1

Hydrogen Bond Acceptor Count

2

Rotatable Bond Count

2

Exact Mass

88.052429494 g/mol

Monoisotopic Mass

88.052429494 g/mol

Topological Polar Surface Area

37.3Ų

Heavy Atom Count

6

Formal Charge

0

Complexity

49.5

Isotope Atom Count

0

Defined Atom Stereocenter Count

0

Undefined Atom Stereocenter Count

0

Defined Bond Stereocenter Count

0

Undefined Bond Stereocenter Count

0

Covalently-Bonded Unit Count

1

Physical Description

Butyric acid appears as a colorless liquid with a penetrating and unpleasant odor. Flash point 170 °F. Corrosive to metals and tissue. Density 8.0 lb /gal.

Boiling Point

163.7°C

Melting Point

17.8 °F (NTP, 1992)

 

Source: PubChem

Source Species: Nicotiana tabacum
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