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Butyric acid information


Butyric acid
Skeletal structure of butyric acid
Skeletal structure of butyric acid
Flat structure of butyric acid
Flat structure of butyric acid
Space filling model of butyric acid
Names
Preferred IUPAC name
Butanoic acid[1]
Other names
Ethylacetic acid
1-Propanecarboxylic acid
Propylformic acid
C4:0 (Lipid numbers)
Identifiers
CAS Number
  • Butyric acid: 107-92-6 checkY
  • Butyrate: 461-55-2 checkY
3D model (JSmol)
  • Butyric acid: Interactive image
ChEBI
  • Butyric acid: CHEBI:30772 checkY
ChEMBL
  • Butyric acid: ChEMBL14227 checkY
ChemSpider
  • Butyric acid: 259 checkY
  • Butyrate: 94582 checkY
DrugBank
  • Butyric acid: DB03568 checkY
ECHA InfoCard 100.003.212 Edit this at Wikidata
EC Number
  • Butyric acid: 203-532-3
IUPHAR/BPS
  • Butyric acid: 1059
KEGG
  • Butyric acid: C00246 checkY
MeSH Butyric+acid
PubChem CID
  • Butyric acid: 264
  • Butyrate: 104775
RTECS number
  • Butyric acid: ES5425000
UNII
  • Butyric acid: 40UIR9Q29H checkY
UN number 2820
CompTox Dashboard (EPA)
  • Butyric acid: DTXSID8021515 Edit this at Wikidata
InChI
  • InChI=1S/C4H8O2/c1-2-3-4(5)6/h2-3H2,1H3,(H,5,6) checkY
    Key: FERIUCNNQQJTOY-UHFFFAOYSA-N checkY
  • Butyric acid: InChI=1/C4H8O2/c1-2-3-4(5)6/h2-3H2,1H3,(H,5,6)
    Key: FERIUCNNQQJTOY-UHFFFAOYAP
SMILES
  • Butyric acid: O=C(O)CCC
Properties
Chemical formula
 C
3H
7COOH
Molar mass 88.106 g·mol−1
Appearance Colorless liquid
Odor Unpleasant, similar to vomit or body odor
Density 1.135 g/cm3 (−43 °C)[2]
0.9528 g/cm3 (25 °C)[3]
Melting point −5.1 °C (22.8 °F; 268.0 K)[3]
Boiling point 163.75 °C (326.75 °F; 436.90 K)[3]
Sublimation
conditions
 Sublimes at −35 °C
ΔsublHo = 76 kJ/mol[4]
Solubility in water
 Miscible
Solubility Miscible with ethanol, ether. Slightly soluble in CCl4
log P 0.79
Vapor pressure 0.112 kPa (20 °C)
0.74 kPa (50 °C)
9.62 kPa (100 °C)[4]
Henry's law
constant (kH)
 5.35·10−4 L·atm/mol
Acidity (pKa) 4.82
Magnetic susceptibility (χ)
 −55.10·10−6 cm3/mol
Thermal conductivity 1.46·105 W/m·K
Refractive index (nD)
 1.398 (20 °C)[3]
Viscosity 1.814 cP (15 °C)[5]
1.426 cP (25 °C)
Structure
Crystal structure
 Monoclinic (−43 °C)[2]
Space group
 C2/m[2]
Lattice constant
a = 8.01 Å, b = 6.82 Å, c = 10.14 Å[2]
α = 90°, β = 111.45°, γ = 90°
Dipole moment
 0.93 D (20 °C)[5]
Thermochemistry
Heat capacity (C)
 178.6 J/mol·K[4]
Std molar
entropy (S⦵298)
 222.2 J/mol·K[5]
Std enthalpy of
formation (ΔfH⦵298)
 −533.9 kJ/mol[4]
Std enthalpy of
combustion (ΔcH⦵298)
 2183.5 kJ/mol[4]
Hazards
GHS labelling:
Pictograms
 GHS05: Corrosive[6]
Signal word
 Danger
Hazard statements
 H314[6]
Precautionary statements
 P280, P305+P351+P338, P310[6]
NFPA 704 (fire diamond)
NFPA 704 four-colored diamondHealth 3: Short exposure could cause serious temporary or residual injury. E.g. chlorine gasFlammability 2: Must be moderately heated or exposed to relatively high ambient temperature before ignition can occur. Flash point between 38 and 93 °C (100 and 200 °F). E.g. diesel fuelInstability 0: Normally stable, even under fire exposure conditions, and is not reactive with water. E.g. liquid nitrogenSpecial hazards (white): no code
3
2
0
Flash point 71 to 72 °C (160 to 162 °F; 344 to 345 K)[6]
Autoignition
temperature
 440 °C (824 °F; 713 K)[6]
Explosive limits 2.2–13.4%
Lethal dose or concentration (LD, LC):
LD50 (median dose)
 2000 mg/kg (oral, rat)
Safety data sheet (SDS) External MSDS
Related compounds
Related carboxylic acids
 Propionic acid, Pentanoic acid
Related compounds
 1-Butanol
Butyraldehyde
Methyl butyrate
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
Infobox references

Butyric acid (/ˈbjuːtɪrɪk/; from Ancient Greek: βούτῡρον, meaning "butter"), also known under the systematic name butanoic acid, is a straight-chain alkyl carboxylic acid with the chemical formula CH3CH2CH2CO2H. It is an oily, colorless liquid with an unpleasant odor. Isobutyric acid (2-methylpropanoic acid) is an isomer. Salts and esters of butyric acid are known as butyrates or butanoates. The acid does not occur widely in nature, but its esters are widespread. It is a common industrial chemical[7] and an important component in the mammalian gut.

  1. ^ "Applications to Specific Classes of Compounds". Nomenclature of Organic Chemistry : IUPAC Recommendations and Preferred Names 2013 (Blue Book). Cambridge: The Royal Society of Chemistry. 2014. p. 746. doi:10.1039/9781849733069-00648. ISBN 978-0-85404-182-4.
  2. ^ a b c d Strieter FJ, Templeton DH (1962). "Crystal structure of butyric acid" (PDF). Acta Crystallographica. 15 (12): 1240–1244. Bibcode:1962AcCry..15.1240S. doi:10.1107/S0365110X6200328X.
  3. ^ a b c d Lide, David R., ed. (2009). CRC Handbook of Chemistry and Physics (90th ed.). Boca Raton, Florida: CRC Press. ISBN 978-1-4200-9084-0.
  4. ^ a b c d e Butanoic acid in Linstrom, Peter J.; Mallard, William G. (eds.); NIST Chemistry WebBook, NIST Standard Reference Database Number 69, National Institute of Standards and Technology, Gaithersburg (MD) (retrieved 27 October 2020)
  5. ^ a b c "Butanoic acid". Chemister.ru. 19 March 2007. Retrieved 27 October 2020.
  6. ^ a b c d e Sigma-Aldrich Co., Butyric acid. Retrieved on 27 October 2020.
  7. ^ Riemenschneider, Wilhelm (2002). "Carboxylic Acids, Aliphatic". Ullmann's Encyclopedia of Industrial Chemistry. Weinheim: Wiley-VCH. doi:10.1002/14356007.a05_235. ISBN 978-3527306732.

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Butyric acid

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Butyric acid (/ˈbjuːtɪrɪk/; from Ancient Greek: βούτῡρον, meaning "butter"), also known under the systematic name butanoic acid, is a straight-chain alkyl...

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Crotonic acid

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Isocrotonic acid is an isomer of crotonic acid. Crotonic acid is soluble in water and many organic solvents. Its odor is similar to that of butyric acid. Crotonic...

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Ethyl butyrate

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Ethyl butyrate is synthesised in Jamaican rum upon the estrification of butyric acid from muck and ethanol during the distillation process. This gives Jamaican...

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Organic acid

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organic acids. A few common examples include: Lactic acid Acetic acid Formic acid Citric acid Oxalic acid Uric acid Malic acid Tartaric acid Butyric acid Folic...

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Isobutyric acid

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acid, also known as 2-methylpropanoic acid or isobutanoic acid, is a carboxylic acid with structural formula (CH3)2CHCOOH. It is an isomer of butyric...

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Perfluorobutanoic acid

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Perfluorobutanoic acid (PFBA) is a perfluoroalkyl carboxylic acid with the formula C3F7CO2H. As the perfluorinated derivative of butyric acid, this colourless...

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Losartan

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Due to the Detection of Trace Amounts of N-Nitroso N-Methyl 4-amino butyric acid (NMBA) Impurity Found in the Active Pharmaceutical Ingredient (API)"...

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Butane

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temperature and pressure. The name butane comes from the root but- (from butyric acid, named after the Greek word for butter) and the suffix -ane. It was discovered...

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Alpha hydroxycarboxylic acid

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butyric acid, alpha hydroxy carboxylic acid, is used commercially in a racemic mixture to substitute for methionine in animal feed. α-Hydroxy acids,...

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Fatty acid

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fatty acids (SCFAs) are fatty acids with aliphatic tails of five or fewer carbons (e.g. butyric acid). Medium-chain fatty acids (MCFAs) are fatty acids with...

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Auxin

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include indole-3-acetic acid, 4-chloroindole-3-acetic acid, phenylacetic acid, indole-3-butyric acid, and indole-3-propionic acid. However, most of the...

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Butyric anhydride

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butyric acid with elimination of one water molecule (hence its name). Butyric anhydride is a clear colorless liquid that smells strongly of butyric acid...

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Formic acid

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fresh hay, to promote the fermentation of lactic acid and to suppress the formation of butyric acid; it also allows fermentation to occur quickly, and...

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Tributyrin

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triglyceride naturally present in butter. It is an ester composed of butyric acid and glycerol. Among other things, it is used as an ingredient in making...

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Hydroxybutyric acid

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derivatives of butyric acid. The carboxylate anion and the esters of hydroxybutyric acids are known as hydroxybutyrates. β-hydroxybutyric acid is relevant...

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Butyronitrile

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Ammonia Cyanic acid Cyanoethynyl Formaldehyde Fulminic acid HCCN Hydrogen peroxide Hydromagnesium isocyanide Isocyanic acid Isothiocyanic acid Ketenyl Methylene...

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List of saturated fatty acids

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Saturated fatty acids are fatty acids that make up saturated fats. List of unsaturated fatty acids Carboxylic acid List of carboxylic acids Dicarboxylic acid...

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Carboxylic acid

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exist; in this system, carboxylic acids have an -oic acid suffix. For example, butyric acid (CH3CH2CH2CO2H) is butanoic acid by IUPAC guidelines. For nomenclature...

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Silage

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and the attendant acid fermentation brings about decomposition of the carbohydrates present into acetic, butyric and lactic acids. This product is named...

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Sodium butyrate

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butyrate is a compound with formula Na(C3H7COO). It is the sodium salt of butyric acid. It has various effects on cultured mammalian cells including inhibition...

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Valeric acid

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Valeric acid or pentanoic acid is a straight-chain alkyl carboxylic acid with the chemical formula CH3(CH2)3COOH. Like other low-molecular-weight carboxylic...

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