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IUPAC name 4,8a-dimethyldecalin-4a-ol or, (4S,4aS,8aR)-4,8a-dimethyl-1,2,3,4,5,6,7,8-octahydronaphthalen-4a-ol
Other names 4,8a-dimethyl-decahydronaphthalen-4a-ol

or, octahydro-4,8a-dimethyl-4a(2H)-naphthalenol

CAS number 19700-21-1
PubChem 29746
InChI InChI=1/C12H22O/c1-10-6-5-8-11(2)7-3-4-9-12(10,11)13/h10,13H,3-9H2,1-2H3


Molecular formula C12H22O
Molar mass 182.30248 g/mol
Boiling point

270 to 271 °C @ 101.325 kPa

Flash point 103.89 degrees Celsius
Except where noted otherwise, data are given for
materials in their standard state
(at 25 °C, 100 kPa)

Infobox disclaimer and references

Geosmin, which literally translates to "earth smell", is an organic compound with a distinct earthy flavour and aroma, and is responsible for the earthy taste of beets. The human nose is extremely sensitive to geosmin, able to detect it at concentrations down to 5 parts per trillion.

Geosmin is produced by several classes of microbes, including cyanobacteria (blue-green algae) and actinobacteria especially though streptomyces, and released when these microbes die. Communities whose water supply depends 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.

Geosmin is also responsible for the muddy smell in bottom-dwelling freshwater fish such as carp and catfish. Blue green algae produce geosmin and methylisoborneol which concentrate in the skin and dark muscle tissue. Geosmin breaks down in acid conditions, and hence vinegar and other acidic ingredients in fish recipes help reduce the muddy flavor.

Recently, the biosynthesis of geosmin by a bifunctional Streptomyces coelicolor enzyme has been unravelled by Jiang et al..[1][2] A single enzyme, the germacradienol/germacrene D Synthase converts farnesyl diphosphate to geosmin in a two step reaction.

Streptomyces coelicolor is the model representative of a group of soil-dwelling organisms with a complex lifecycle involving mycelial growth and spore formation. Beside the production of volatile geosmin, it also produces many other complex molecules of pharmacological interest and his genome sequence is available at the Sanger Institute.

See also


  1. ^ Jiang, J.; X. He, D.E. Cane (2006). "Geosmin biosynthesis. Streptomyces coelicolor germacradienol/germacrene D Synthase converts farnesyl diphosphate to geosmin". J. Am. Chem. Soc. 128 (25): 8128-8129. doi:10.1021/ja062669x.
  2. ^ Jiang, J.; X. He, D.E. Cane (2007). "Biosynthesis of the earthy odorant geosmin by a bifunctional Streptomyces coelicolor enzyme". Nat. Chem. Biol. advanced online publication. doi:10.1038/nchembio.2007.29.
  • Geosmin at PubChem
  • Bear, I.J.; R.G. Thomas (1964). "Nature of argillaceous odour". Nature 201 (4923): 993-995. doi:10.1038/201993a0.
  • Bear, I.J.; R.G. Thomas (1965). "Petrichor and plant growth". Nature 207 (5005): 1415-1416. doi:10.1038/2071415a0.
  • The genome of Streptomyces coelicolor producing geosmin is available at the Sanger Institute:
This article is licensed under the GNU Free Documentation License. It uses material from the Wikipedia article "Geosmin". A list of authors is available in Wikipedia.
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