Structure via PubChem · Public domain (PubChem)
geosmin
Sign in to saveAlso known as (4S-(4alpha,4aalpha,8abeta))-octahydro-4,8a-dimethyl-4a(2H)-naphthol, octahydro-4alpha,8abeta-dimethyl-4aalpha(2H)-naphthol, trans-1,10-dimethyl-trans-decalol, (-)-Geosmin, trans-1,10-Dimethyl-trans-9-decalol
Geosmin ( ) is an irregular sesquiterpenoid with 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, along with 2-methylisoborneol, are the major biological causes of taste and odor outbreaks in drinking water worldwide and in farmed fish. Geosmin is also responsible for the earthy taste of beetroots and a contributor to the strong scent, known as petrichor, that occurs when rain falls after a spell of dry weather or when soil is disturbed.
Chemical data
- Formula
- C12H22O
- Molecular weight
- 182.3 g/mol
- IUPAC name
- (4S,4aS,8aR)-4,8a-dimethyl-1,2,3,4,5,6,7,8-octahydronaphthalen-4a-ol
- SMILES
- C[C@H]1CCC[C@@]2([C@@]1(CCCC2)O)C
- InChIKey
- JLPUXFOGCDVKGO-TUAOUCFPSA-N
- XLogP
- 3.3
- Polar surface area
- 20.2 Ų
- H-bond donors
- 1
- H-bond acceptors
- 1
- Formal charge
- 0
via PubChem
Wikidata facts
- Mass
- 182.167
Show 4 more facts
- chemical formula
- C₁₂H₂₂O
- canonical SMILES
- CC1CCCC2(C1(CCCC2)O)C
- isomeric SMILES
- C[C@H]1CCC[C@@]2([C@@]1(CCCC2)O)C
- Commons category
- Geosmin
via Wikidata · CC0
~6 min read
Article
6 sectionsContents
- Production
- Effects
- Geosmin remediation in drinking water
- See also
- References
- Further reading
Geosmin ( ) is an irregular sesquiterpenoid with 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, along with 2-methylisoborneol, are the major biological causes of taste and odor outbreaks in drinking water worldwide and in farmed fish. Geosmin is also responsible for the earthy taste of beetroots and a contributor to the strong scent, known as petrichor, that occurs when rain falls after a spell of dry weather or when soil is disturbed.
Geosmin is a bicyclic alcohol with formula , a derivative of decalin. It is produced from the universal sesquiterpene precursor farnesyl pyrophosphate (also known as farnesyl diphosphate), in a two-step -dependent reaction. Its name is derived from the Ancient Greek words (), meaning "earth", and (), meaning "smell". The word was coined in 1965 by the American biochemist Nancy N. Gerber (1929–1985) and the French-American biologist Hubert A. Lechevalier (1926–2015).