Butyric acid

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Butyric acid
Skeletal structure of butyric acid Butyric acid acsv.svg
Skeletal structure of butyric acid
Flat structure of butyric acid Butyric acid flat structure.png
Flat structure of butyric acid
Space filling model of butyric acid Butyric-acid-3D-balls.png
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
3D model (JSmol)
ChEBI
ChEMBL
ChemSpider
  • Butyric acid: 259  Yes check.svgY
  • Butyrate: 94582  Yes check.svgY
DrugBank
ECHA InfoCard 100.003.212 OOjs UI icon edit-ltr-progressive.svg
EC Number
  • Butyric acid:203-532-3
KEGG
MeSH Butyric+acid
PubChem CID
RTECS number
  • Butyric acid:ES5425000
UNII
UN number 2820
  • InChI=1S/C4H8O2/c1-2-3-4(5)6/h2-3H2,1H3,(H,5,6) Yes check.svgY
    Key: FERIUCNNQQJTOY-UHFFFAOYSA-N Yes check.svgY
  • Butyric acid:InChI=1/C4H8O2/c1-2-3-4(5)6/h2-3H2,1H3,(H,5,6)
    Key: FERIUCNNQQJTOY-UHFFFAOYAP
  • Butyric acid:O=C(O)CCC
Properties
C
3H
7COOH
Molar mass 88.106 g·mol−1
AppearanceColorless 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]
Sublimes at −35 °C
ΔsublHo = 76 kJ/mol [4]
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]
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) [3]
Viscosity 1.814 cP (15 °C) [5]
1.426 cP (25 °C)
Structure
Monoclinic (−43 °C) [2]
C2/m [2]
a = 8.01 Å, b = 6.82 Å, c = 10.14 Å [2]
α = 90°, β = 111.45°, γ = 90°
0.93 D (20 °C) [5]
Thermochemistry
178.6 J/mol·K [4]
Std molar
entropy (S⦵298)
222.2 J/mol·K [5]
−533.9 kJ/mol [4]
2183.5 kJ/mol [4]
Hazards
GHS labelling:
GHS-pictogram-acid.svg [6]
Danger
H314 [6]
P280, P305+P351+P338, P310 [6]
NFPA 704 (fire diamond)
NFPA 704.svgHealth 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]
440 °C (824 °F; 713 K) [6]
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
 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).

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 CH3CH2CH2COOH. 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.

History

Butyric acid was first observed in an impure form in 1814 by the French chemist Michel Eugène Chevreul. By 1818, he had purified it sufficiently to characterize it. However, Chevreul did not publish his early research on butyric acid; instead, he deposited his findings in manuscript form with the secretary of the Academy of Sciences in Paris, France. Henri Braconnot, another French chemist, was also researching the composition of butter and was publishing his findings and this led to disputes about priority. As early as 1815, Chevreul claimed that he had found the substance responsible for the smell of butter. [8] By 1817, he published some of his findings regarding the properties of butyric acid and named it. [9] However, it was not until 1823 that he presented the properties of butyric acid in detail. [10] The name butyric acid comes from βούτῡρον , meaning "butter", the substance in which it was first found. The Latin name butyrum (or buturum) is similar.

Occurrence

Triglycerides of butyric acid make up 3–4% of butter. When butter goes rancid, butyric acid is liberated from the glyceride by hydrolysis. [11] It is one of the fatty acid subgroup called short-chain fatty acids. Butyric acid is a typical carboxylic acid that reacts with bases and affects many metals. [12] It is found in animal fat and plant oils, bovine milk, breast milk, butter, parmesan cheese, body odor, vomit and as a product of anaerobic fermentation (including in the colon). [13] It has a taste somewhat like butter and an unpleasant odor. Mammals with good scent detection abilities, such as dogs, can detect it at 10 parts per billion, whereas humans can detect it only in concentrations above 10 parts per million. In food manufacturing, it is used as a flavoring agent. [14]

In humans, butyric acid is one of two primary endogenous agonists of human hydroxycarboxylic acid receptor 2 (HCA2), a Gi/o-coupled G protein-coupled receptor. [15] [16]

Butyric acid is present as its octyl ester in parsnip (Pastinaca sativa) [17] and in the seed of the ginkgo tree. [18]

Production

Industrial

In industry, butyric acid is produced by hydroformylation from propene and syngas, forming butyraldehyde, which is oxidised to the final product. [7]

H2 + CO + CH3CH=CH2 → CH3CH2CH2CHOoxidation→butyric acid

It can be separated from aqueous solutions by saturation with salts such as calcium chloride. The calcium salt, Ca(C4H7O2)2· H2O, is less soluble in hot water than in cold.

Microbial biosynthesis

One pathway for butyrate biosynthesis. Relevant enzymes: acetoacetyl-CoA thiolase, NAD- and NADP-dependent 3-hydroxybutyryl-CoA dehydrogenase, 3-hydroxybutyryl-CoA dehydratase, and NAD-dependent butyryl-CoA dehydrogenase. ButyrateBisyn.svg
One pathway for butyrate biosynthesis. Relevant enzymes: acetoacetyl-CoA thiolase, NAD- and NADP-dependent 3-hydroxybutyryl-CoA dehydrogenase, 3-hydroxybutyryl-CoA dehydratase, and NAD-dependent butyryl-CoA dehydrogenase.

Butyrate is produced by several fermentation processes performed by obligate anaerobic bacteria. [19] This fermentation pathway was discovered by Louis Pasteur in 1861. Examples of butyrate-producing species of bacteria:

The pathway starts with the glycolytic cleavage of glucose to two molecules of pyruvate, as happens in most organisms. Pyruvate is oxidized into acetyl coenzyme A catalyzed by pyruvate:ferredoxin oxidoreductase. Two molecules of carbon dioxide (CO2) and two molecules of hydrogen (H2) are formed as waste products. Subsequently, ATP is produced in the last step of the fermentation. Three molecules of ATP are produced for each glucose molecule, a relatively high yield. The balanced equation for this fermentation is

C6H12O6 → C4H8O2 + 2CO2 + 2H2

Other pathways to butyrate include succinate reduction and crotonate disproportionation.

ActionResponsible enzyme
Acetyl coenzyme A converts into acetoacetyl coenzyme A acetyl-CoA-acetyl transferase
Acetoacetyl coenzyme A converts into β-hydroxybutyryl CoA β-hydroxybutyryl-CoA dehydrogenase
β-hydroxybutyryl CoA converts into crotonyl CoA crotonase
Crotonyl CoA converts into butyryl CoA (CH3CH2CH2C=O−CoA) butyryl CoA dehydrogenase
A phosphate group replaces CoA to form butyryl phosphate phosphobutyrylase
The phosphate group joins ADP to form ATP and butyrate butyrate kinase

Several species form acetone and n-butanol in an alternative pathway, which starts as butyrate fermentation. Some of these species are:

These bacteria begin with butyrate fermentation, as described above, but, when the pH drops below 5, they switch into butanol and acetone production to prevent further lowering of the pH. Two molecules of butanol are formed for each molecule of acetone.

The change in the pathway occurs after acetoacetyl CoA formation. This intermediate then takes two possible pathways:

For commercial purposes Clostridium species are used preferably for butyric acid or butanol production. The most common species used for probiotics is the Clostridium butyricum. [20]

Fermentable fiber sources

Highly-fermentable fiber residues, such as those from resistant starch, oat bran, pectin, and guar are transformed by colonic bacteria into short-chain fatty acids (SCFA) including butyrate, producing more SCFA than less fermentable fibers such as celluloses. [13] [21] One study found that resistant starch consistently produces more butyrate than other types of dietary fiber. [22] The production of SCFA from fibers in ruminant animals such as cattle is responsible for the butyrate content of milk and butter. [23]

Fructans are another source of prebiotic soluble dietary fibers which can be digested to produce butyrate. [24] They are often found in the soluble fibers of foods which are high in sulfur, such as the allium and cruciferous vegetables. Sources of fructans include wheat (although some wheat strains such as spelt contain lower amounts), [25] rye, barley, onion, garlic, Jerusalem and globe artichoke, asparagus, beetroot, chicory, dandelion leaves, leek, radicchio, the white part of spring onion, broccoli, brussels sprouts, cabbage, fennel, and prebiotics, such as fructooligosaccharides (FOS), oligofructose, and inulin. [26] [27]

Chemical reactions

Butyric acid reacts as a typical carboxylic acid: it can form amide, ester, anhydride, and chloride derivatives. [28] The latter, butyryl chloride, is commonly used as the intermediate to obtain the others.

Uses

Butyric acid is used in the preparation of various butyrate esters. It is used to produce cellulose acetate butyrate (CAB), which is used in a wide variety of tools, paints, and coatings, and is more resistant to degradation than cellulose acetate. [29] CAB can degrade with exposure to heat and moisture, releasing butyric acid. [30]

Low-molecular-weight esters of butyric acid, such as methyl butyrate, have mostly pleasant aromas or tastes. [7] As a consequence, they are used as food and perfume additives. It is an approved food flavoring in the EU FLAVIS database (number 08.005).

Due to its powerful odor, it has also been used as a fishing bait additive. [31] Many of the commercially available flavors used in carp (Cyprinus carpio) baits use butyric acid as their ester base. It is not clear whether fish are attracted by the butyric acid itself or the substances added to it. Butyric acid was one of the few organic acids shown to be palatable for both tench and bitterling. [32]

The substance has been used as a stink bomb by the Sea Shepherd Conservation Society to disrupt Japanese whaling crews. [33] The Dutch branch of Extinction Rebellion has used it as a chemical agent in a clothing store; several people who became unwell were treated on site by an ambulance crew. [34]

Pharmacology

Human enzyme and GPCR binding [35] [36]
Inhibited enzyme IC50 (nM)Entry note
HDAC1 16,000
HDAC2 12,000
HDAC3 9,000
HDAC4 2,000,000Lower bound
HDAC5 2,000,000Lower bound
HDAC6 2,000,000Lower bound
HDAC7 2,000,000Lower bound
HDAC8 15,000
HDAC9 2,000,000Lower bound
CA1 511,000
CA2 1,032,000
GPCR target pEC50 Entry note
FFAR2 2.9–4.6Full agonist
FFAR3 3.8–4.9Full agonist
HCA2 2.8Agonist

Pharmacodynamics

Butyric acid (pKa 4.82) is fully ionized at physiological pH, so its anion is the material that is mainly relevant in biological systems. It is one of two primary endogenous agonists of human hydroxycarboxylic acid receptor 2 (HCA2, also known as GPR109A), a Gi/o-coupled G protein-coupled receptor (GPCR), [15] [16]

Like other short-chain fatty acids (SCFAs), butyrate is an agonist at the free fatty acid receptors FFAR2 and FFAR3, which function as nutrient sensors that facilitate the homeostatic control of energy balance; however, among the group of SCFAs, only butyrate is an agonist of HCA2. [37] [38] It is also an HDAC inhibitor (specifically, HDAC1, HDAC2, HDAC3, and HDAC8), [35] [36] a drug that inhibits the function of histone deacetylase enzymes, thereby favoring an acetylated state of histones in cells. [38]

Pharmacokinetics

Butyrate that is produced in the colon through microbial fermentation of dietary fiber is primarily absorbed and metabolized by colonocytes and the liver [note 1] for the generation of ATP during energy metabolism; however, some butyrate is absorbed in the distal colon, which is not connected to the portal vein, thereby allowing for the systemic distribution of butyrate to multiple organ systems through the circulatory system. [38] [39] Butyrate that has reached systemic circulation can readily cross the blood–brain barrier via monocarboxylate transporters (i.e., certain members of the SLC16A group of transporters). [40] [41] Other transporters that mediate the passage of butyrate across lipid membranes include SLC5A8 (SMCT1), SLC27A1 (FATP1), and SLC27A4 (FATP4). [35] [41]

Metabolism

Butyric acid is metabolized by various human XM-ligases (ACSM1, ACSM2B, ASCM3, ACSM4, ACSM5, and ACSM6), also known as butyrate–CoA ligase. [42] [43] The metabolite produced by this reaction is butyryl–CoA, and is produced as follows: [42]

Adenosine triphosphate + butyric acid + coenzyme A → adenosine monophosphate + pyrophosphate + butyryl-CoA

As a short-chain fatty acid, butyrate is metabolized by mitochondria as an energy (i.e., adenosine triphosphate or ATP) source through fatty acid metabolism. [38] In particular, it is an important energy source for cells lining the mammalian colon (colonocytes). [24] Without butyrates, colon cells undergo autophagy (i.e., self-digestion) and die. [44]

In humans, the butyrate precursor tributyrin, which is naturally present in butter, is metabolized by triacylglycerol lipase into dibutyrin and butyrate through the reaction: [45]

Tributyrin + H2O → dibutyrin + butyric acid

Biochemistry

Butyrate has numerous effects on energy homeostasis in humans. These effects occur through its metabolism by mitochondria to generate ATP during fatty acid metabolism or through one or more of its histone-modifying enzyme targets (i.e., the class I histone deacetylases) and G-protein coupled receptor targets (i.e., FFAR2, FFAR3, and HCA2). [37] [46]

Mammalian gut

Butyrate is essential to host immune homeostasis. [37] Although the role and importance of butyrate in the gut is not fully understood, many researchers argue that a depletion of butyrate-producing bacteria in patients with several vasculitic conditions is essential to the pathogenesis of these disorders. A depletion of butyrate in the gut is typically caused by an absence or depletion of butyrate-producing-bacteria (BPB). This depletion in BPB leads to microbial dysbiosis. This is characterized by an overall low biodiversity and a depletion of key butyrate-producing members. Butyrate is an essential microbial metabolite with a vital role as a modulator of proper immune function in the host. It has been shown that children lacking in BPB are more susceptible to allergic disease [47] and type 1 diabetes. [48] Butyrate is also reduced in a diet low in dietary fiber, which can induce inflammation and have other adverse affects insofar as these short-chain fatty acids activate PPAR-γ. [49]

Decreased butyrate levels lead to a damaged or dysfunctional intestinal epithelial barrier. [50] Butyrate reduction has also been associated with Clostridioides difficile proliferation. Conversely, a high-fiber diet results in higher butyric acid concentration and inhibition of C. difficile growth. [51]

In the gut microbiomes found in the class Mammalia, omnivores and herbivores have butyrate-producing bacterial communities dominated by the butyryl-CoA:acetate CoA-transferase pathway, whereas carnivores have butyrate-producing bacterial communities dominated by the butyrate kinase pathway. [52]

The odor of butyric acid, which emanates from the sebaceous follicles of all mammals, works on ticks as a signal.

Immunomodulation

Butyrate's effects on the immune system are mediated through the inhibition of class I histone deacetylases and activation of its G-protein coupled receptor targets: HCA2 (GPR109A), FFAR2 (GPR43), and FFAR3 (GPR41). [53]

Colonocytes

Responsible for about 70% of energy from the colonocytes, butyric acid is a critical SCFA in colon homeostasis. [54] Short-chain fatty acids, which include butyric acid, are produced by beneficial colonic bacteria that feed on, or ferment prebiotics, supporting colonocytes by increasing energy conversion. [21]

Butyrate salts and esters

The butanoate ion, C 3 H 7COO−, is the conjugate base of butyric acid. It is the form found in biological systems at physiological pH. A butyric (or butanoic) compound is a carboxylate salt or ester of butyric acid.

Examples

Salts

Esters

See also

Notes

  1. ↑ Most of the butyrate that is absorbed into blood plasma from the colon enters the circulatory system via the portal vein; most of the butyrate that enters the circulatory system by this route is taken up by the liver. [38]

References

Wikisource-logo.svg This article incorporates text from a publication now in the public domain :  Chisholm, Hugh, ed. (1911). "Butyric Acid". Encyclopædia Britannica (11th ed.). Cambridge University Press.

  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. 1 2 3 4 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. 1 2 3 4 Lide, David R., ed. (2009). CRC Handbook of Chemistry and Physics (90th ed.). Boca Raton, Florida: CRC Press. ISBN   978-1-4200-9084-0.
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  5. 1 2 3 "Butanoic acid". Chemister.ru. 19 March 2007. Retrieved 27 October 2020.
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  8. ↑ Chevreul (1815) "Lettre de M. Chevreul à MM. les rédacteurs des Annales de chimie" (Letter from Mr. Chevreul to the editors of the Annals of Chemistry), Annales de chimie, 94 : 73–79; in a footnote spanning pp. 75–76, he mentions that he had found a substance that is responsible for the smell of butter.
  9. ↑ Chevreul (1817) "Extrait d'une lettre de M. Chevreul à MM. les Rédacteurs du Journal de Pharmacie" (Extract of a letter from Mr. Chevreul to the editors of the Journal of Pharmacy), Journal de Pharmacie et des sciences accessoires, 3 : 79–81. On p. 81, he named butyric acid: "Ce principe, que j'ai appelé depuis acid butérique, … " (This principle [i.e., constituent], which I have since named "butyric acid", … )
  10. ↑ E. Chevreul, Recherches chimiques sur les corps gras d'origine animale [Chemical researches on fatty substances of animal origin] (Paris, France: F.G. Levrault, 1823), pages 115–133.
  11. ↑ Woo, A.H.; Lindsay, R.C. (1983). "Stepwise Discriminant Analysis of Free Fatty Acid Profiles for Identifying Sources of Lipolytic Enzymes in Rancid Butter". Journal of Dairy Science. 66 (10): 2070–2075. doi: 10.3168/jds.S0022-0302(83)82052-9 .
  12. ↑ ICSC 1334 – Butyric acid. Inchem.org (23 November 1998). Retrieved on 2020-10-27.
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  17. ↑ Carroll, Mark J.; Berenbaum, May R. (2002). "Behavioral responses of the parsnip webworm to host plant volatiles". Journal of Chemical Ecology. 28 (11): 2191–2201. Bibcode:2002JCEco..28.2191C. doi:10.1023/A:1021093114663. PMID   12523562. S2CID   23512190.
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  20. ↑ Zigová, Jana; Šturdı́k, Ernest; Vandák, Dušan; Schlosser, Štefan (October 1999). "Butyric acid production by Clostridium butyricum with integrated extraction and pertraction" . Process Biochemistry. 34 (8): 835–843. doi:10.1016/S0032-9592(99)00007-2.
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  31. ↑ Freezer Baits Archived 25 January 2010 at the Wayback Machine , nutrabaits.net
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  33. ↑ Japanese Whalers Injured by Acid-Firing Activists Archived 8 June 2010 at the Wayback Machine , newser.com, 10 February 2010
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  35. 1 2 3 "Butyric acid". IUPHAR/BPS Guide to Pharmacology. International Union of Basic and Clinical Pharmacology. Retrieved 13 July 2018.
  36. 1 2 "Butanoic acid and Sodium butyrate". BindingDB. The Binding Database. Retrieved 27 October 2020.
  37. 1 2 3 Kasubuchi M, Hasegawa S, Hiramatsu T, Ichimura A, Kimura I (2015). "Dietary gut microbial metabolites, short-chain fatty acids, and host metabolic regulation". Nutrients. 7 (4): 2839–2849. doi: 10.3390/nu7042839 . PMC   4425176 . PMID   25875123. Short-chain fatty acids (SCFAs) such as acetate, butyrate, and propionate, which are produced by gut microbial fermentation of dietary fiber, are recognized as essential host energy sources and act as signal transduction molecules via G-protein coupled receptors (FFAR2, FFAR3, OLFR78, GPR109A) and as epigenetic regulators of gene expression by the inhibition of histone deacetylase (HDAC). Recent evidence suggests that dietary fiber and the gut microbial-derived SCFAs exert multiple beneficial effects on the host energy metabolism not only by improving the intestinal environment, but also by directly affecting various host peripheral tissues.
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