2-Methylisoborneol

changed changed 477214620 Methylisoborneol.png skin-invert-image 150px 1,2,7,7-tetramethylbicyclo[2.2.1]heptan-2-ol 2-Methyl-2-bornanol MIB correct chemspider 16024 61987 1/C11H20O/c1-9(2)8-5-6-10(9,3)11(4,12)7-8/h8,12H,5-7H2,1-4H3 LFYXNXGVLGKVCJ-UHFFFAOYAW OC2(C)CC1CCC2(C1(C)C)C correct chemspider 1S/C11H20O/c1-9(2)8-5-6-10(9,3)11(4,12)7-8/h8,12H,5-7H2,1-4H3 correct chemspider LFYXNXGVLGKVCJ-UHFFFAOYSA-N changed ?? 2371-42-8 correct FDA D43XMP4DNW 16913 C20243 CC1(C2CCC1(C(C2)(C)O)C)C C11H20O 168.28 g/mol 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.10.1128/aem.02250-06 Biochemical and Ecological Control of Geosmin and 2-Methylisoborneol in Source Waters 2007 Jüttner Friedrich Watson Susan B. Applied and Environmental Microbiology 73 14 4395–4406 17400777 1932821 2007ApEnM..73.4395J 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.978-1-78040-665-7 Taste and Odour in Source and Drinking Water: Causes, Controls, and Consequences Lin Tsair-Fuh Watson Susan Andrea M. Dietrich (Mel) Suffet I. H. 15 March 2018 IWA 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. Biochemical and Ecological Control of Geosmin and 2-Methylisoborneol in Source Waters Juttner, F. Watson, S. Applied and Environmental Microbiology 2007 73 14 4395–4406 10.1128/AEM.02250-06 17400777 1932821 2007ApEnM..73.4395J A Guide to Geosmin and MIB-producing Cyanobacteria in the United States G. Izaguirre W.D. Taylor Water Science and Technology 2004 49 9 19–24 10.2166/wst.2004.0524 15237602 2004WSTec..49...19I 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. 10.1021/jf980419x Analysis of 2-Methylisoborneol and Geosmin in Catfish by Microwave Distillation−Solid-Phase Microextraction Journal of Agricultural and Food Chemistry 47 164–169 1999 Lloyd Steven W Grimm Casey C 1 10563866 1999JAFC...47..164L Rhodococcus and Comamonas bacteria can degrade 2-methylisoborneol.Guttman Lior van Rijn Jaap Isolation of Bacteria Capable of Growth with 2-Methylisoborneol and Geosmin as the Sole Carbon and Energy Sources Applied and Environmental Microbiology 15 January 2012 78 2 363–370 10.1128/AEM.06333-11 22081577 3255726 2012ApEnM..78..363G free References Category:Flavors Category:Tertiary alcohols Category:Monoterpenes Category:Norbornanes