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Butyric acid

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**History and Occurrence of Butyric Acid:**
– Discovered in 1814 by Michel Eugène Chevreul.
– Named in 1817, with detailed properties presented in 1823.
– Derived from the Greek word for butter.
– Found in butter, animal fat, plant oils, bovine milk, breast milk, and cheese.
– Detected by dogs at 10 parts per billion.
– Used in food manufacturing as a flavoring agent.
– Acts as an endogenous agonist of human hydroxycarboxylic acid receptor2.

**Production and Reactions of Butyric Acid:**
– Industrial production from propene and syngas.
– Separated from aqueous solutions using salts like calcium chloride.
– Microbial biosynthesis by anaerobic bacteria.
– Reacts as a typical carboxylic acid.
– Forms various derivatives like amides, esters, anhydrides, and chlorides.
– Utilized in the production of various butyrate esters.

**Uses and Pharmacokinetics of Butyric Acid:**
– Used in the preparation of butyrate esters.
– Produces cellulose acetate butyrate (CAB) for tools, paints, coatings.
– Acts as an HDAC inhibitor.
– Metabolized by human XM-ligases into butyryl-CoA.
– Essential energy source for colon cells.
– Metabolized in mitochondria for ATP generation.
– Absorbed and metabolized by colonocytes and the liver.

**Biological Effects and Health Implications of Butyric Acid:**
– Modulates histone-modifying enzymes and G-protein coupled receptors.
– Has antimicrobial and anticarcinogenic effects.
– Essential for immune homeostasis in the gut.
– Promotes regulatory T cell differentiation.
– Protects the intestinal epithelial barrier and inhibits inflammation.
– Impacts energy homeostasis, inflammation, and immune function in humans.

**Butyric Acid in Disease Prevention and Potential Treatments:**
– Implications for colon cancer prevention and treatment.
– Butyrate depletion can impact the pathogenesis of vasculitic conditions.
– Fecal microbiota transplants can replenish butyrate levels effectively.
– Butyrate administration via oral supplements or enemas terminates inflammation symptoms.
– Healthy levels of butyrate in the gut are crucial for immune system health.
– Butyrate has implications for immune function, mood, and behavior.

Butyric acid (Wikipedia)

Butyric acid (/ˈbjtɪrɪk/; 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 and an important component in the mammalian gut.

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
Preferred IUPAC name
Butanoic acid
Other names
Ethylacetic acid
1-Propanecarboxylic acid
Propylformic acid
C4:0 (Lipid numbers)
3D model (JSmol)
ECHA InfoCard 100.003.212 Edit this at Wikidata
EC Number
  • Butyric acid: 203-532-3
MeSH Butyric+acid
RTECS number
  • Butyric acid: ES5425000
UN number 2820
  • InChI=1S/C4H8O2/c1-2-3-4(5)6/h2-3H2,1H3,(H,5,6) checkY
  • Butyric acid: InChI=1/C4H8O2/c1-2-3-4(5)6/h2-3H2,1H3,(H,5,6)
  • Butyric acid: O=C(O)CCC
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)
0.9528 g/cm3 (25 °C)
Melting point −5.1 °C (22.8 °F; 268.0 K)
Boiling point 163.75 °C (326.75 °F; 436.90 K)
Sublimes at −35 °C
ΔsublHo = 76 kJ/mol
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)
5.35·10−4 L·atm/mol
Acidity (pKa) 4.82
−55.10·10−6 cm3/mol
Thermal conductivity 1.46·105 W/m·K
1.398 (20 °C)
Viscosity 1.814 cP (15 °C)
1.426 cP (25 °C)
Monoclinic (−43 °C)
a = 8.01 Å, b = 6.82 Å, c = 10.14 Å
α = 90°, β = 111.45°, γ = 90°
0.93 D (20 °C)
178.6 J/mol·K
222.2 J/mol·K
−533.9 kJ/mol
2183.5 kJ/mol
GHS labelling:
GHS05: Corrosive
P280, P305+P351+P338, P310
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
Flash point 71 to 72 °C (160 to 162 °F; 344 to 345 K)
440 °C (824 °F; 713 K)
Explosive limits 2.2–13.4%
Lethal dose or concentration (LD, LC):
2000 mg/kg (oral, rat)
Safety data sheet (SDS) External MSDS
Related compounds
Propionic acid, Pentanoic acid
Related compounds
Methyl butyrate
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
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