Names | |
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Preferred IUPAC name 3-Hydroxypropanal | |
Identifiers | |
3D model (JSmol) | |
ChEBI | |
ChemSpider | |
ECHA InfoCard | 100.016.696 |
KEGG | |
PubChem CID | |
UNII | |
CompTox Dashboard (EPA) | |
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Properties | |
C3H6O2 | |
Molar mass | 74.079 g·mol−1 |
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa). |
Reuterin (3-hydroxypropionaldehyde) is the organic compound with the formula HOCH2CH2CHO. It is a bifunctional molecule, containing both a hydroxy and aldehyde functional groups.
The name reuterin is derived from Lactobacillus reuteri , which produces the compound biosynthetically from glycerol as a broad-spectrum antibiotic (bacteriocin). [1] L. reuteri itself is named after the microbiologist Gerhard Reuter, who did early work in distinguishing it as a distinct species.
In aqueous solution 3-hydroxypropionaldehyde exists in equilibrium with its hydrate (1,1,3-propanetriol), in which the aldehyde group converts to a geminal diol:
The hydrate is also in equilibrium with its dimer (2-(2-hydroxyethyl)-4-hydroxy-1,3-dioxane), which dominates at high concentrations. These three components - the aldehyde, its dimer, and the hydrate are therefore in a dynamic equilibrium. [2]
Besides, 3-hydroxypropionaldehyde suffers an spontaneous dehydration in aqueous solution, and the resulting molecule is called acrolein. [3]
In fact, the term reuterin is the name given to the dynamic system formed by 3-hydroxypropionaldehyde, its hydrate, the dimer, and acrolein. This last molecule, acrolein, was recently included in reuterin definition. [3] [4]
3-Hydroxypropionaldehyde is formed by the condensation of acetaldehyde and formaldehyde. This reaction, when conducted in the gas-phase, was the basis for a now obsolete industrial route acrolein: [5]
Presently 3-hydroxypropionaldehyde is an intermediate in the production of pentaerythritol. Hydrogenation of reuterin gives 1,3-propanediol.
Reuterin is an intermediate in the metabolism of glycerol to 1,3-propanediol catalysed by the coenzyme B12-dependent glycerol dehydratase.
Reuterin is a potent antimicrobial compound produced by Lactobacillus reuteri . It is an intermediate in the metabolism of glycerol to 1,3-propanediol catalysed by the coenzyme B12-dependent diol dehydrase. It inhibits the growth of some harmful Gram-negative and Gram-positive bacteria, along with yeasts, molds, and protozoa. [6] L. reuteri can secrete sufficient amounts of reuterin to inhibit the growth of harmful gut organisms, without killing beneficial gut bacteria, allowing L. reuteri to remove gut invaders while keeping normal gut flora intact. [7]
Reuterin is water-soluble, effective in a wide range of pH, resistant to proteolytic and lipolytic enzymes, and has been studied as a food preservative or auxiliary therapeutic agent. [8] [9] [10]
Reuterin as an extracted compound has been shown capable of killing Escherichia coli O157:H7 and Listeria monocytogenes , with the addition of lactic acid increasing its efficacy. [3] [10] It has also been demonstrated to kill Escherichia coli O157:H7 when produced by L. reuteri. [11]
Escherichia coli ( ESH-ə-RIK-ee-ə KOH-ly) is a gram-negative, facultative anaerobic, rod-shaped, coliform bacterium of the genus Escherichia that is commonly found in the lower intestine of warm-blooded organisms. Most E. coli strains are harmless, but some serotypes such as EPEC, and ETEC are pathogenic and can cause serious food poisoning in their hosts, and are occasionally responsible for food contamination incidents that prompt product recalls. Most strains are part of the normal microbiota of the gut and are harmless or even beneficial to humans (although these strains tend to be less studied than the pathogenic ones). For example, some strains of E. coli benefit their hosts by producing vitamin K2 or by preventing the colonization of the intestine by pathogenic bacteria. These mutually beneficial relationships between E. coli and humans are a type of mutualistic biological relationship — where both the humans and the E. coli are benefitting each other. E. coli is expelled into the environment within fecal matter. The bacterium grows massively in fresh fecal matter under aerobic conditions for three days, but its numbers decline slowly afterwards.
Escherichia coli O157:H7 is a serotype of the bacterial species Escherichia coli and is one of the Shiga-like toxin–producing types of E. coli. It is a cause of disease, typically foodborne illness, through consumption of contaminated and raw food, including raw milk and undercooked ground beef. Infection with this type of pathogenic bacteria may lead to hemorrhagic diarrhea, and to kidney failure; these have been reported to cause the deaths of children younger than five years of age, of elderly patients, and of patients whose immune systems are otherwise compromised.
Lactobacillus is a genus of gram-positive, aerotolerant anaerobes or microaerophilic, rod-shaped, non-spore-forming bacteria. Until 2020, the genus Lactobacillus comprised over 260 phylogenetically, ecologically, and metabolically diverse species; a taxonomic revision of the genus assigned lactobacilli to 25 genera.
Acrolein is the simplest unsaturated aldehyde. It is a colorless liquid with a foul and acrid aroma. The smell of burnt fat is caused by glycerol in the burning fat breaking down into acrolein. It is produced industrially from propene and mainly used as a biocide and a building block to other chemical compounds, such as the amino acid methionine.
Escherichia is a genus of Gram-negative, non-spore-forming, facultatively anaerobic, rod-shaped bacteria from the family Enterobacteriaceae. In those species which are inhabitants of the gastrointestinal tracts of warm-blooded animals, Escherichia species provide a portion of the microbially derived vitamin K for their host. A number of the species of Escherichia are pathogenic. The genus is named after Theodor Escherich, the discoverer of Escherichia coli. Escherichia are facultative aerobes, with both aerobic and anaerobic growth, and an optimum temperature of 37 °C. Escherichia are usually motile by flagella, produce gas from fermentable carbohydrates, and do not decarboxylate lysine or hydrolyze arginine. Species include E. albertii, E. fergusonii, E. hermannii, E. ruysiae, E. marmotae and most notably, the model organism and clinically relevant E. coli. Formerly, Shimwellia blattae and Pseudescherichia vulneris were also classified in this genus.
Lebanon bologna is a type of cured, smoked, and fermented semidry beef sausage; it is not, in spite of its name, a pork-based bologna. Similar in appearance and texture to salami, it is somewhat darker in color, and is typically served as a cold cut or appetizer.
Romaine or cos lettuce is a variety of lettuce that grows in a tall head of sturdy dark green leaves with firm ribs down their centers. Unlike most lettuces, it is tolerant of heat. In North America, romaine is often sold as whole heads or as "hearts" that have had the outer leaves removed and are often packaged together.
Sorbitol-MacConkey agar is a variant of traditional MacConkey agar used in the detection of E. coli O157:H7. Traditionally, MacConkey agar has been used to distinguish those bacteria that ferment lactose from those that do not. This is important because gut bacteria, such as Escherichia coli, can typically ferment lactose, while important gut pathogens, such as Salmonella enterica and most shigellas are unable to ferment lactose. Shigella sonnei can ferment lactose, but only after prolonged incubation, so it is referred to as a late-lactose fermenter.
Limosilactobacillus reuteri is a lactic acid bacterium found in a variety of natural environments, including the gastrointestinal tract of humans and other animals. It does not appear to be pathogenic and may have health effects.
1,3-Propanediol is the organic compound with the formula CH2(CH2OH)2. This 3-carbon diol is a colorless viscous liquid that is miscible with water.
Walter Dobrogosz is a Professor Emeritus of North Carolina State University, best known for his discovery and further research on the probiotic bacterium Lactobacillus reuteri.
Enteroinvasive Escherichia coli (EIEC) is a type of pathogenic bacteria whose infection causes a syndrome that is identical to shigellosis, with profuse diarrhea and high fever. EIEC are highly invasive, and they use adhesin proteins to bind to and enter intestinal cells. They produce no toxins, but severely damage the intestinal wall through mechanical cell destruction.
Raw meat generally refers to any type of uncooked muscle tissue of an animal used for food. In the meat production industry, the term ‘meat’ refers specifically to mammalian flesh, while the words ‘poultry’ and ‘seafood’ are used to differentiate between the tissue of birds and aquatic creatures.
Copper and its alloys are natural antimicrobial materials. Ancient civilizations exploited the antimicrobial properties of copper long before the concept of microbes became understood in the nineteenth century. In addition to several copper medicinal preparations, it was also observed centuries ago that water contained in copper vessels or transported in copper conveyance systems was of better quality than water contained or transported in other materials.
Shigatoxigenic Escherichia coli (STEC) and verotoxigenic E. coli (VTEC) are strains of the bacterium Escherichia coli that produce Shiga toxin. Only a minority of the strains cause illness in humans. The ones that do are collectively known as enterohemorrhagic E. coli (EHEC) and are major causes of foodborne illness. When infecting the large intestine of humans, they often cause gastroenteritis, enterocolitis, and bloody diarrhea and sometimes cause a severe complication called hemolytic-uremic syndrome (HUS). Cattle are an important natural reservoir for EHEC because the colonised adult ruminants are asymptomatic. This is because they lack vascular expression of the target receptor for Shiga toxins. The group and its subgroups are known by various names. They are distinguished from other strains of intestinal pathogenic E. coli including enterotoxigenic E. coli (ETEC), enteropathogenic E. coli (EPEC), enteroinvasive E. coli (EIEC), enteroaggregative E. coli (EAEC), and diffusely adherent E. coli (DAEC).
Escherichia coli is a gram-negative, rod-shaped bacterium that is commonly found in the lower intestine of warm-blooded organisms (endotherms). Most E. coli strains are harmless, but pathogenic varieties cause serious food poisoning, septic shock, meningitis, or urinary tract infections in humans. Unlike normal flora E. coli, the pathogenic varieties produce toxins and other virulence factors that enable them to reside in parts of the body normally not inhabited by E. coli, and to damage host cells. These pathogenic traits are encoded by virulence genes carried only by the pathogens.
BioGaia is a Swedish biotechnology company that develops, markets and sells a range of probiotic products. It has patented the use of several Lactobacillus reuteri strains and offers gut and immune health products containing L. reuteri Protectis, one of the human L. reuteri strain and oral health products containing L. reuteri Prodentis, a blend of the L. reuteri strains DSM 17938 and ATCC PTA 5289. Products containing L. reuteri have been proven to be both effective and safe in several applications: infant colic, diarrhea prevention and mitigation in children, eradication of H. pylori infection and reduction of side effects from standard H. pylori treatment, amelioration of gingivitis, and general illness prevention in children and adults. BioGaia was ranked 9th in the Top 30 Global Probiotic Food Ingredient Companies list by FoodTalks in 2021. The BioGaia -B share is listed on the NASDAQ OMX Nordic Exchange.
Proteobiotics are natural metabolites which are produced by fermentation process of specific probiotic strains. These small oligopeptides were originally discovered in and isolated from culture media used to grow probiotic bacteria and may account for some of the health benefits of probiotics.
Limosilactobacillus is a thermophilic and heterofermentative genus of lactic acid bacteria created in 2020 by splitting from Lactobacillus. The name is derived from the Latin limosus "slimy", referring to the property of most strains in the genus to produce exopolysaccharides from sucrose. The genus currently includes 31 species or subspecies, most of these were isolated from the intestinal tract of humans or animals. Limosilactobacillus reuteri has been used as a model organism to evaluate the host-adaptation of lactobacilli to the human and animal intestine and for the recruitment of intestinal lactobacilli for food fermentations.