Names | |
---|---|
IUPAC name 1,2,7,7-tetramethylbicyclo[2.2.1]heptan-2-ol | |
Other names 2-Methyl-2-bornanol | |
Identifiers | |
3D model (JSmol) | |
Abbreviations | MIB |
ChEBI | |
ChemSpider | |
KEGG | |
PubChem CID | |
CompTox Dashboard (EPA) | |
| |
| |
Properties | |
C11H20O | |
Molar mass | 168.28 g/mol |
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa). |
2-Methylisoborneol (MIB) is an irregular monoterpene derived from the universal monoterpene precursor geranyl pyrophosphate. MIB and the irregular sesquiterpene geosmin together account for the majority of biologically-caused taste and odor outbreaks in drinking water worldwide. [1] MIB has a distinct earthy or musty odor, which most people can easily smell. The odor detection threshold of MIB is very low, ranging from 0.002 to 0.02 micrograms per liter in water. [2] MIB is also a factor in cork taint in winemaking.
MIB is produced by various blue-green algae (cyanobacteria) and filamentous bacteria in the class Actinomycetia, and also some other prokaryotes and eukaryotes. The main genera in the cyanobacteria that have been shown to produce MIB include Oscillatoria , Phormidium , and Planktothrix , while the main genus in the Actinomycetia that produces MIB is Streptomyces . [3] [4] They give a musty or earthy odor that can be quite strong if an algal bloom is present. Subsequent death of the microorganisms will release MIB that is trapped in the cells. Along with geosmin, the off flavors that result are issues in the seafood industry. This chemical is the major cause of "muddy" or "dirt" flavors in catfish and crawfish. [5]
Rhodococcus and Comamonas bacteria can degrade 2-methylisoborneol. [6]
Cyanobacteria, also called Cyanobacteriota or Cyanophyta, are a phylum of gram-negative bacteria that obtain energy via photosynthesis. The name cyanobacteria refers to their color, which similarly forms the basis of cyanobacteria's common name, blue-green algae, although they are not usually scientifically classified as algae. They appear to have originated in a freshwater or terrestrial environment. Sericytochromatia, the proposed name of the paraphyletic and most basal group, is the ancestor of both the non-photosynthetic group Melainabacteria and the photosynthetic cyanobacteria, also called Oxyphotobacteria.
Acidobacteriota is a phylum of Gram-negative bacteria. Its members are physiologically diverse and ubiquitous, especially in soils, but are under-represented in culture.
Sphingomonadaceae are a gram-negative bacterial family of the Alphaproteobacteria. An important feature is the presence of sphingolipids in the outer membrane of the cell wall. The cells are ovoid or rod-shaped. Others are also pleomorphic, i.e. the cells change the shape over time. Some species from Sphingomonadaceae family are dominant components of biofilms.
Azotobacter is a genus of usually motile, oval or spherical bacteria that form thick-walled cysts and may produce large quantities of capsular slime. They are aerobic, free-living soil microbes that play an important role in the nitrogen cycle in nature, binding atmospheric nitrogen, which is inaccessible to plants, and releasing it in the form of ammonium ions into the soil. In addition to being a model organism for studying diazotrophs, it is used by humans for the production of biofertilizers, food additives, and some biopolymers. The first representative of the genus, Azotobacter chroococcum, was discovered and described in 1901 by Dutch microbiologist and botanist Martinus Beijerinck. Azotobacter species are Gram-negative bacteria found in neutral and alkaline soils, in water, and in association with some plants.
Geosmin ( jee-OZ-min) is an irregular sesquiterpenoid, produced from the universal sesquiterpene precursor farnesyl pyrophosphate (also known as farnesyl diphosphate), in a two-step Mg2+-dependent reaction. Geosmin, along with the irregular monoterpene 2-methylisoborneol, together account for the majority of biologically-caused taste and odor outbreaks in drinking water worldwide. Geosmin has a distinct earthy or musty odor, which most people can easily smell. The geosmin odor detection threshold in humans is very low, ranging from 0.006 to 0.01 micrograms per liter in water. Geosmin is also responsible for the earthy taste of beetroots and a contributor to the strong scent (petrichor) that occurs in the air when rain falls after a spell of dry weather or when soil is disturbed.
Iron-oxidizing bacteria are chemotrophic bacteria that derive energy by oxidizing dissolved iron. They are known to grow and proliferate in waters containing iron concentrations as low as 0.1 mg/L. However, at least 0.3 ppm of dissolved oxygen is needed to carry out the oxidation.
Filamentation is the anomalous growth of certain bacteria, such as Escherichia coli, in which cells continue to elongate but do not divide. The cells that result from elongation without division have multiple chromosomal copies.
Campylobacterota are a phylum of bacteria. All species of this phylum are Gram-negative.
Sesquiterpenes are a class of terpenes that consist of three isoprene units and often have the molecular formula C15H25. Like monoterpenes, sesquiterpenes may be cyclic or contain rings, including many unique combinations. Biochemical modifications such as oxidation or rearrangement produce the related sesquiterpenoids.
Dehalococcoides is a genus of bacteria within class Dehalococcoidia that obtain energy via the oxidation of hydrogen and subsequent reductive dehalogenation of halogenated organic compounds in a mode of anaerobic respiration called organohalide respiration. They are well known for their great potential to remediate halogenated ethenes and aromatics. They are the only bacteria known to transform highly chlorinated dioxins, PCBs. In addition, they are the only known bacteria to transform tetrachloroethene to ethene.
Saccharibacteria, formerly known as TM7, is a major bacterial lineage. It was discovered through 16S rRNA sequencing.
The class Zetaproteobacteria is the sixth and most recently described class of the Pseudomonadota. Zetaproteobacteria can also refer to the group of organisms assigned to this class. The Zetaproteobacteria were originally represented by a single described species, Mariprofundus ferrooxydans, which is an iron-oxidizing neutrophilic chemolithoautotroph originally isolated from Kamaʻehuakanaloa Seamount in 1996 (post-eruption). Molecular cloning techniques focusing on the small subunit ribosomal RNA gene have also been used to identify a more diverse majority of the Zetaproteobacteria that have as yet been unculturable.
Thiolactones are a class of heterocyclic compounds in organic chemistry. They are analogs of the more common lactones in which an oxygen atom is replaced with a sulfur atom. The sulfur atom is within the ring system and adjacent to a carbonyl group.
Geosmin synthase or germacradienol-geosmin synthase designates a class of bifunctional enzymes that catalyze the conversion of farnesyl diphosphate (FPP) to geosmin, a volatile organic compound known for its earthy smell. The N-terminal half of the protein catalyzes the conversion of farnesyl diphosphate to germacradienol and germacrene D, followed by the C-terminal-mediated conversion of germacradienol to geosmin. The conversion of FPP to geosmin was previously thought to involve multiple enzymes in a biosynthetic pathway.
2-methylisoborneol synthase (EC 4.2.3.118, sco7700, 2-MIB cyclase, MIB synthase, MIBS) is an enzyme with systematic name (E)-2-methylgeranyl-diphosphate diphosphate-lyase (cyclizing, 2-methylisoborneol-forming). This enzyme catalyses the following chemical reaction
Sodalis is a genus of bacteria within the family Pectobacteriaceae. This genus contains several insect endosymbionts and also a free-living group. It is studied due to its potential use in the biological control of the tsetse fly. Sodalis is an important model for evolutionary biologists because of its nascent endosymbiosis with insects.
Naegleria fowleri, colloquially known as the "brain-eating amoeba", is a species of the genus Naegleria. It belongs to the phylum Percolozoa and is technically classified as a shape-shifting amoeboflagellate excavate, rather than a true amoeba. This free-living microorganism primarily feeds on bacteria but can become pathogenic, causing an extremely rare, sudden, severe, and usually fatal brain infection known as naegleriasis or primary amoebic meningoencephalitis (PAM).
Oscillatoria brevis, is a species of the genus Oscillatoria first identified in 1892. It is a blue-green filamentous cyanobacterium, which can be found in brackish and fresh waterways. O. brevis can also be isolated from soil.
Bacterioplankton counting is the estimation of the abundance of bacterioplankton in a specific body of water, which is useful information to marine microbiologists. Various counting methodologies have been developed over the years to determine the number present in the water being observed. Methods used for counting bacterioplankton include epifluorescence microscopy, flow cytometry, measures of productivity through frequency of dividing cells (FDC), thymidine incorporation, and leucine incorporation.
Microbial oxidation of sulfur is the oxidation of sulfur by microorganisms to build their structural components. The oxidation of inorganic compounds is the strategy primarily used by chemolithotrophic microorganisms to obtain energy to survive, grow and reproduce. Some inorganic forms of reduced sulfur, mainly sulfide (H2S/HS−) and elemental sulfur (S0), can be oxidized by chemolithotrophic sulfur-oxidizing prokaryotes, usually coupled to the reduction of oxygen (O2) or nitrate (NO3−). Anaerobic sulfur oxidizers include photolithoautotrophs that obtain their energy from sunlight, hydrogen from sulfide, and carbon from carbon dioxide (CO2).