Caproate fermentation

Last updated

Caproate fermentation is a metabolic process used by different bacteria to utilize different organic substrates for the production of caproic acid (hexanoic acid) as well as other valuable byproducts. [1] Caproic acid is a valuable compound in food industries as a flavor additive, feedstock for chemical industries, antimicrobial agents in the pharmaceutical industry, and more. [2] Though this process is used by varying bacterial species, [3] the most common species utilizing caproate fermentation in its metabolic process is Clostridium kluyveri . [4] This species, as well as others, utilize caproate fermentation through the breakdown of varying substrates for energy production, waste management and increased ability for survival in different environments.

Contents

Chemical structures and properties

Chemical Structure

Chemical Structure of Caproic Acid Caproic acid acsv.svg
Chemical Structure of Caproic Acid

Caproic acid is otherwise known as hexanoic acid. In solid state, the acid appears as a white crystalline structure, while when liquid, it appears clear with a yellow tint. Any contact with caproic acid will cause irritation to various parts of the body and is toxic to humans. [5] The acid is formed through β-oxidation which elongates a short chain carboxylic acid origin using lactic acid as the electron donor to drive the process. [2] This is done through a series of reactions driven by varying enzymes. [6]

Chemical methods

Carboxylic acids and alcohols are required as substrates for caproate fermentation. Due to the danger of high concentrations in these substrates, they must be diluted. This danger factor results in more materials needed and a more meticulous process to perform fermentation, which is costly. Recent studies suggest that food waste can serve as an alternative source for these substrates, potentially reducing cost and waste. [7] The interest in creating more efficient methods for producing caproates—specifically n-caproate (hexanoate) and n-caprylate (octanoate)—has been challenged by the natural efficiency of C. kluyveri. [8] There are many different ways to produce caproate fermentation however, it is difficult to avoid disruption of the cell and effectively produce caproate. To efficiently produce caproate, optimal conditions are required including: pH, temperature, and environmental concentration. [9]

Process of Fermentation

Certain bacterial species convert carbohydrates (like glucose) into caproate (hexanoate), a six-carbon fatty acid.

Throughout this process of fermentation, bacteria anaerobically break down carbohydrates like glucose through a series of biochemical reactions producing caproate. Furthermore, chain elongation of ethanol and acetate is also needed to create caproate. Ethanol is toxic to many bacterial species, so the ethanol must be pretty balanced in the process to ensure caproate production. Studies have found that with an ethanol/acetate ratio higher than 7:3 require no extra electron donors and a 10:1 ratio produced 8.42g/L of caproate. Additional byproducts are formed like hydrogen gas, carbon dioxide, and sometimes butyrate or acetate. [4] Caproate is the main product, hence the name of caproate fermentation.

Function and Usage

Caproic acid a straight-chain saturated fatty acid has a use in many different areas. These areas being things like artificial flavoring because of its esters. This acid is found in different kind of fats and oils of animals. Not only for flavoring but caproic acid can be used in different medicinal applications as well. [10] Caproic acid is used widely by the agricultural industry and can also be used in antibiotics and as lubricants. More recent studies have proposed the idea that caproic acid can be used to ferment organic waste. Considering that organic waste is 46% of the total waste produced each year. [6]

Research and Industry

Following the Covid-19 pandemic, an international market for medium chain carboxylic acids like caproic acid has emerged. This market is estimated to grow to 358.8 million US dollars by 2030. [11] Caproic acid, a MCCA (medium-chain carboxylic acid) having a multitude of implementations that include cosmetics, solvents, fuels, and antibiotic growth-promoting substitutes in animal feed. [8] With such optimistic market growth being estimated, research surrounding the synthesis of caproic acids has increased and new methods are being explored. Among the methods being looked at is caproate fermentation through microbial cultures. [8]

Related Research Articles

<span class="mw-page-title-main">Propionic acid</span> Carboxylic acid with chemical formula CH3CH2CO2H

Propionic acid is a naturally occurring carboxylic acid with chemical formula CH
3
CH
2
CO
2
H
. It is a liquid with a pungent and unpleasant smell somewhat resembling body odor. The anion CH
3
CH
2
CO
2
as well as the salts and esters of propionic acid are known as propionates or propanoates.

Anaerobic respiration is respiration using electron acceptors other than molecular oxygen (O2). Although oxygen is not the final electron acceptor, the process still uses a respiratory electron transport chain.

In chemistry, disproportionation, sometimes called dismutation, is a redox reaction in which one compound of intermediate oxidation state converts to two compounds, one of higher and one of lower oxidation state. The reverse of disproportionation, such as when a compound in an intermediate oxidation state is formed from precursors of lower and higher oxidation states, is called comproportionation, also known as symproportionation.

Acidogenesis is the second stage in the four stages of anaerobic digestion:

<span class="mw-page-title-main">Caproic acid</span> Chemical compound

Caproic acid, also known as hexanoic acid, is the carboxylic acid derived from hexane with the chemical formula CH3(CH2)4COOH. It is a colorless oily liquid with an odor that is fatty, cheesy, waxy, and like that of goats or other barnyard animals. It is a fatty acid found naturally in various animal fats and oils, and is one of the chemicals that gives the decomposing fleshy seed coat of the ginkgo its characteristic unpleasant odor. It is also one of the components of vanilla and cheese. The primary use of caproic acid is in the manufacture of its esters for use as artificial flavors, and in the manufacture of hexyl derivatives, such as hexylphenols. Salts and esters of caproic acid are known as caproates or hexanoates. Several progestin medications are caproate esters, such as hydroxyprogesterone caproate and gestonorone caproate.

Bioconversion, also known as biotransformation, is the conversion of organic materials, such as plant or animal waste, into usable products or energy sources by biological processes or agents, such as certain microorganisms. One example is the industrial production of cortisone, which one step is the bioconversion of progesterone to 11-alpha-Hydroxyprogesterone by Rhizopus nigricans. Another example is the bioconversion of glycerol to 1,3-propanediol, which is part of scientific research for many decades.

<span class="mw-page-title-main">Bioconversion of biomass to mixed alcohol fuels</span>

The bioconversion of biomass to mixed alcohol fuels can be accomplished using the MixAlco process. Through bioconversion of biomass to a mixed alcohol fuel, more energy from the biomass will end up as liquid fuels than in converting biomass to ethanol by yeast fermentation.

In biology, syntrophy, syntrophism, or cross-feeding is the cooperative interaction between at least two microbial species to degrade a single substrate. This type of biological interaction typically involves the transfer of one or more metabolic intermediates between two or more metabolically diverse microbial species living in close proximity to each other. Thus, syntrophy can be considered an obligatory interdependency and a mutualistic metabolism between different microbial species, wherein the growth of one partner depends on the nutrients, growth factors, or substrates provided by the other(s).

<span class="mw-page-title-main">Fermentation</span> Metabolic redox process producing energy in the absence of oxygen.

Fermentation is a type of redox metabolism carried out in the absence of oxygen. During fermentation, organic molecules are catabolized and donate electrons to other organic molecules. In the process, ATP and organic end products are formed.

<span class="mw-page-title-main">Methanobacteria</span> Class of archaea

Methanobacteria is a class of archaeans in the kingdom Euryarchaeota. Several of the classes of the Euryarchaeota are methanogens and the Methanobacteria are one of these classes.

<span class="mw-page-title-main">Acetone–butanol–ethanol fermentation</span> Chemical process

Acetone–butanol–ethanol (ABE) fermentation, also known as the Weizmann process, is a process that uses bacterial fermentation to produce acetone, n-butanol, and ethanol from carbohydrates such as starch and glucose. It was developed by chemist Chaim Weizmann and was the primary process used to produce acetone, which was needed to make cordite, a substance essential for the British war industry during World War I.

<i>Scenedesmus</i> Genus of green algae

Scenedesmus is a genus of green algae, in the class Chlorophyceae. They are colonial and non-motile. They are one of the most common components of phytoplankton in freshwater habitats worldwide.

<span class="mw-page-title-main">Butyryl-CoA</span> Chemical compound

Butyryl-CoA is an organic coenzyme A-containing derivative of butyric acid. It is a natural product found in many biological pathways, such as fatty acid metabolism, fermentation, and 4-aminobutanoate (GABA) degradation. It mostly participates as an intermediate, a precursor to and converted from crotonyl-CoA. This interconversion is mediated by butyryl-CoA dehydrogenase.

Dark fermentation is the fermentative conversion of organic substrate to biohydrogen. It is a complex process manifested by diverse groups of bacteria, involving a series of biochemical reactions using three steps similar to anaerobic conversion. Dark fermentation differs from photofermentation in that it proceeds without the presence of light.

<span class="mw-page-title-main">Photofermentation</span>

Photofermentation is the fermentative conversion of organic substrate to biohydrogen manifested by a diverse group of photosynthetic bacteria by a series of biochemical reactions involving three steps similar to anaerobic conversion. Photofermentation differs from dark fermentation because it only proceeds in the presence of light.

Fermentative hydrogen production is the fermentative conversion of organic substrates to H2. Hydrogen produced in this manner is often called biohydrogen. The conversion is effected by bacteria and protozoa, which employ enzymes. Fermentative hydrogen production is one of several anaerobic conversions.

<span class="mw-page-title-main">Acetic acid</span> Colorless and faint organic acid found in vinegar

Acetic acid, systematically named ethanoic acid, is an acidic, colourless liquid and organic compound with the chemical formula CH3COOH. Vinegar is at least 4% acetic acid by volume, making acetic acid the main component of vinegar apart from water. It has been used, as a component of vinegar, throughout history from at least the third century BC.

Single cell oil, also known as Microbial oil consists of the intracellular storage lipids, triacyglycerols. It is similar to vegetable oil, another biologically produced oil. They are produced by oleaginous microorganisms, which is the term for those bacteria, molds, algae and yeast, which can accumulate 20% to 80% lipids of their biomass. The accumulation of lipids take place by the end of logarithmic phase and continues during station phase until carbon source begins to reduce with nutrition limitation.

Clostridium autoethanogenum is an anaerobic bacterium that produces ethanol from carbon monoxide, in so-called syngas fermentation, being one of the few known microorganisms to do so. It is gram-positive, spore-forming, rod-like, motile, and was first isolated from rabbit feces. Its type strain is strain JA1-1. Its genome has been sequenced and the genes required for utilising carbon monoxide as a sole carbon and energy source have been determined.

Butyrate fermentation is a process that produces butyric acid via anaerobic bacteria. This process occurs commonly in clostridia which can be isolated from many anaerobic environments such as mud, fermented foods, and intestinal tracts or feces. Clostridium can ferment carbohydrates into butyric acid, producing byproducts including hydrogen gas, carbon dioxide, and acetate. Butyrate fermentation is currently being utilized in the production of a variety of biochemicals and biofuels.

References

  1. Ding, Hong-Bo; Tan, Giin-Yu Amy; Wang, Jing-Yuan (2010-12-01). "Caproate formation in mixed-culture fermentative hydrogen production". Bioresource Technology. 101 (24): 9550–9559. Bibcode:2010BiTec.101.9550D. doi:10.1016/j.biortech.2010.07.056. ISSN   0960-8524.
  2. 1 2 Cavalcante, Willame de Araújo; Leitão, Renato Carrhá; Gehring, Tito A.; Angenent, Largus T.; Santaella, Sandra Tédde (2017-03-01). "Anaerobic fermentation for n-caproic acid production: A review". Process Biochemistry. 54: 106–119. doi:10.1016/j.procbio.2016.12.024. ISSN   1359-5113.
  3. Hung, Chun-Hsiung; Chang, Yi-Tang; Chang, Yu-Jie (September 2011). "Roles of microorganisms other than Clostridium and Enterobacter in anaerobic fermentative biohydrogen production systems--a review". Bioresource Technology. 102 (18): 8437–8444. doi:10.1016/j.biortech.2011.02.084. ISSN   1873-2976. PMID   21429742.
  4. 1 2 Yin, Yanan; Zhang, Yifeng; Karakashev, Dimitar Borisov; Wang, Jianlong; Angelidaki, Irini (October 2017). "Biological caproate production by Clostridium kluyveri from ethanol and acetate as carbon sources". Bioresource Technology. 241: 638–644. Bibcode:2017BiTec.241..638Y. doi:10.1016/j.biortech.2017.05.184. ISSN   1873-2976. PMID   28605728.
  5. PubChem. "Caproic Acid". pubchem.ncbi.nlm.nih.gov. Retrieved 2024-10-16.
  6. 1 2 Dong, Wenjian; Yang, Youli; Liu, Chao; Zhang, Jiachao; Pan, Junting; Luo, Lin; Wu, Genyi; Awasthi, Mukesh Kumar; Yan, Binghua (2023-04-01). "Caproic acid production from anaerobic fermentation of organic waste - Pathways and microbial perspective". Renewable and Sustainable Energy Reviews. 175: 113181. Bibcode:2023RSERv.17513181D. doi:10.1016/j.rser.2023.113181. ISSN   1364-0321.
  7. Zhang, Cunsheng; Liang, Tianyu; Li, Chengmei; Ji, Hairui; Liu, Hongze; Ling, Zhihui; Tian, Zhongjian (2024-09-06). "Caproate production from the mixture of corn straw and food waste via chain elongation with reinforcement of biofilm". Process Biochemistry. 147: 137–146. doi:10.1016/j.procbio.2024.08.019.
  8. 1 2 3 Fernández-Blanco, Carla; Pereira, Alexandra; Veiga, María C.; Kennes, Christian; Ganigué, Ramon (September 2024). "Comprehensive comparative study on n-caproate production by Clostridium kluyveri: batch vs. continuous operation modes". Bioresource Technology. 408: 131138. Bibcode:2024BiTec.40831138F. doi:10.1016/j.biortech.2024.131138. PMID   39043275.
  9. Yu, Jiangnan; Liao, Jialin; Huang, Zhenxing; Wu, Peng; Zhao, Mingxing; Liu, Chunmei; Ruan, Wenquan (2019-07-01). "Enhanced Anaerobic Mixed Culture Fermentation with Anion-Exchange Resin for Caproate Production". Processes. 7 (7): 404. doi: 10.3390/pr7070404 . ISSN   2227-9717.
  10. Stecher. The Merck Index (15th ed.). ISBN   978-0-911910-00-1.
  11. ltd, Research and Markets. "Caproic Acid - Global Strategic Business Report - Research and Markets". www.researchandmarkets.com. Retrieved 2024-11-13.