Geosmin
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IUPAC name
(4S,4aS,8aR)-4,8a-Dimethyl-1,2,3,4,5,6,7,-octahydronaphthalen-4a-ol
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| Other names
4,8a-Dimethyl-decahydronaphthalen-4a-ol; Octahydro-4,8a-dimethyl-4a(2H)-naphthalenol
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3D model (Jmol)
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| ChemSpider | |
| ECHA InfoCard | 100.039.294 |
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PubChem CID
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| Properties | |
| C12H22O | |
| Molar mass | 182.31 g·mol−1 |
| Boiling point | 270 to 271 °C (518 to 520 °F; 543 to 544 K) |
| Hazards | |
| Flash point | 104 °C (219 °F; 377 K) |
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Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
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 (what is   ?) |
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| Infobox references | |
Geosmin is an organic compound with a distinct earthy flavor and aroma produced by a type of Actinobacteria, and is responsible for the earthy taste of beets and a contributor to the strong scent (petrichor) that occurs in the air when rain falls after a dry spell of weather or when soil is disturbed. In chemical terms, it is a bicyclic alcohol with formula C12H22O, a derivative of decalin. Its name is derived from the Greek γεω- "earth" and ὀσμή "smell"
Geosmin is produced by the gram-positive bacteria Streptomyces, a genus of Actinobacteria in the order Actinomycetales, and released when these microorganisms die. Communities whose water supplies depend on surface water can periodically experience episodes of unpleasant-tasting water when a sharp drop in the population of these bacteria releases geosmin into the local water supply. Under acidic conditions, geosmin decomposes into odorless substances.
In 2006, the biosynthesis of geosmin by a bifunctional Streptomyces coelicolor enzyme was unveiled. A single enzyme, geosmin synthase, converts farnesyl diphosphate to geosmin in a two-step reaction.
Streptomyces coelicolor is the model representative of a group of soil-dwelling bacteria with a complex lifecycle involving mycelial growth and spore formation. Besides the production of volatile geosmin, it also produces many other complex molecules of pharmacological interest; its genome sequence is available at the Sanger Institute.
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