Wikipedia:WikiProject Chemicals/Chembox validation/VerifiedDataSandbox and 2-Methylisoborneol: Difference between pages

| Verifiedfields = changed

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| verifiedrevid = 477214620

| ImageFile=Methylisoborneol.png

| ImageSize=150px

| IUPACName=1,2,7,7-tetramethylbicyclo[2.2.1]heptan-2-ol

| OtherNames=2-Methyl-2-bornanol

| Abbreviations = MIB

| ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}}

| ChEBI = 61987

| CASNo_Ref = {{cascite|changed|??}}

| CASNo=2371-42-8

| PubChem=16913

| KEGG = C20243

| SMILES=CC1(C2CCC1(C(C2)(C)O)C)C

| Formula=C₁₁H₂₀O

| MolarMass=168.28 g/mol

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'''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.<ref>{{cite journal|doi=10.1128/aem.02250-06 |title=Biochemical and Ecological Control of Geosmin and 2-Methylisoborneol in Source Waters |date=2007 |last1=Jüttner |first1=Friedrich |last2=Watson |first2=Susan B. |journal=Applied and Environmental Microbiology |volume=73 |issue=14 |pages=4395–4406 |pmid=17400777 |pmc=1932821 |bibcode=2007ApEnM..73.4395J }}</ref> 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.<ref>{{cite book|isbn=978-1-78040-665-7 |title=Taste and Odour in Source and Drinking Water: Causes, Controls, and Consequences |last1=Lin |first1=Tsair-Fuh |last2=Watson |first2=Susan|first3=Andrea M. |last3=Dietrich |last4=(Mel) Suffet |first4=I. H. |date=15 March 2018 |publisher=IWA }}</ref> 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]]''.<ref>{{cite journal | title = Biochemical and Ecological Control of Geosmin and 2-Methylisoborneol in Source Waters | author1 = Juttner, F. |author2= Watson, S. | journal = [[Applied and Environmental Microbiology]] | year = 2007 | volume = 73 | issue = 14 | pages = 4395–4406| doi = 10.1128/AEM.02250-06 | pmid = 17400777 | pmc = 1932821 | bibcode = 2007ApEnM..73.4395J }}</ref><ref>{{cite journal | title = A Guide to Geosmin and MIB-producing Cyanobacteria in the United States | author = G. Izaguirre|author2=W.D. Taylor | journal = [[Water Science and Technology]] | year = 2004 | volume = 49 | issue = 9 | pages = 19–24| doi = 10.2166/wst.2004.0524 | pmid = 15237602 }}</ref> 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]].<ref>{{Cite journal |doi = 10.1021/jf980419x|title = Analysis of 2-Methylisoborneol and Geosmin in Catfish by Microwave Distillation−Solid-Phase Microextraction|journal = Journal of Agricultural and Food Chemistry|volume = 47|pages = 164–169|year = 1999|last1 = Lloyd|first1 = Steven W|last2 = Grimm|first2 = Casey C| issue=1 | pmid=10563866 }}</ref>

''[[Rhodococcus]]'' and ''[[Comamonas]]'' bacteria can degrade 2-methylisoborneol.<ref>{{cite journal |last1=Guttman |first1=Lior |last2=van Rijn |first2=Jaap |title=Isolation of Bacteria Capable of Growth with 2-Methylisoborneol and Geosmin as the Sole Carbon and Energy Sources |journal=Applied and Environmental Microbiology |date=15 January 2012 |volume=78 |issue=2 |pages=363–370 |doi=10.1128/AEM.06333-11|pmid=22081577 | pmc=3255726|bibcode=2012ApEnM..78..363G |doi-access=free }}</ref>

==References==

{{reflist}}

{{DEFAULTSORT:Methylisoborneol, 2-}}

[[Category:Flavors]]

[[Category:Tertiary alcohols]]

[[Category:Monoterpenes]]

[[Category:Norbornanes]]