Geosmin

Geosmin
Names
	Preferred IUPAC name (4S,4aS,8aR)-4,8a-Dimethyloctahydronaphthalen-4a(2H)-ol
	Other names (4S,4aS,8aR)-4,8a-Dimethyl-1,2,3,4,5,6,7,8-octahydronaphthalen-4a-ol; 4,8a-Dimethyl-decahydronaphthalen-4a-ol; Octahydro-4,8a-dimethyl-4a(2H)-naphthalenol
Identifiers
CAS Number	19700-21-1 ;
3D model (JSmol)	Interactive image;
ChEBI	CHEBI:46702 ;
ChemSpider	27642 ;
ECHA InfoCard	100.039.294
PubChem CID	29746;
UNII	MYW912WXJ4 ;
CompTox Dashboard (EPA)	DTXSID801024112 ;
	InChI InChI=1S/C12H22O/c1-10-6-5-8-11(2)7-3-4-9-12(10,11)13/h10,13H,3-9H2,1-2H3/t10-,11+,12-/m0/s1 Key: JLPUXFOGCDVKGO-TUAOUCFPSA-N ; InChI=1/C12H22O/c1-10-6-5-8-11(2)7-3-4-9-12(10,11)13/h10,13H,3-9H2,1-2H3 /t10-,11+,12-/m0/s1;
	SMILES O[C@]12[C@H](CCC[C@]2(CCCC1)C)C;
Properties
Chemical formula	C12H22O
Molar mass	182.307 g·mol−1
Melting point	78 to 82 °C (172 to 180 °F; 351 to 355 K)
Boiling point	270 to 271 °C (518 to 520 °F; 543 to 544 K)
Hazards
Flash point	104 °C (219 °F; 377 K)
	Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa). verify (what is ?) Infobox references

Geosmin (/dʒiˈɒzmɪn/ jee-OZ-min) is an irregular sesquiterpenoid, produced from the universal sesquiterpene precursor farnesyl pyrophosphate (also known as farnesyl diphosphate), in a two-step Mg²⁺-dependent reaction.^[1] Geosmin, along with the irregular monoterpene 2-methylisoborneol, together account for the majority of biologically-caused taste and odor outbreaks in drinking water worldwide.^[2] Geosmin has 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.^[2] Geosmin is also responsible for the earthy taste of beetroots and a contributor to the strong scent (petrichor) that occurs in the air when rain falls after a spell of dry weather or when soil is disturbed.^[3]

In chemical terms, geosmin is a bicyclic alcohol with formula C₁₂H₂₂O, a derivative of decalin. Its name is derived from the Ancient Greek words geō- (γεω-), meaning "earth", and osmḗ (ὀσμή), 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).^[4]^[5]

^ Watson, W.; Juttner, F. (2019). Taste and Odour in Source and Drinking Water: Causes, Controls, and Consequences. IWA Publishing. ISBN 9781780406657.
^ ^a ^b Jüttner, Friedrich; Watson, Susan B. (July 2007). "Biochemical and Ecological Control of Geosmin and 2-methylisoborneol in Source Waters". Applied and Environmental Microbiology. 73 (14): 4395–4706. Bibcode:2007ApEnM..73.4395J. doi:10.1128/AEM.02250-06. PMC 1932821. PMID 17400777. S2CID 1954489.
^ "The earth's perfume". Protein Spotlight (35). June 2003.
^ Cite error: The named reference Gerber was invoked but never defined (see the help page).
^ "geosmin". Merriam-Webster Dictionary. 22 May 2023.

[1] Watson, W.; Juttner, F. (2019). Taste and Odour in Source and Drinking Water: Causes, Controls, and Consequences. IWA Publishing. ISBN 9781780406657.

[aem2007-2] Jüttner, Friedrich; Watson, Susan B. (July 2007). "Biochemical and Ecological Control of Geosmin and 2-methylisoborneol in Source Waters". Applied and Environmental Microbiology. 73 (14): 4395–4706. Bibcode:2007ApEnM..73.4395J. doi:10.1128/AEM.02250-06. PMC 1932821. PMID 17400777. S2CID 1954489.

[3] "The earth's perfume". Protein Spotlight (35). June 2003.

[Gerber-4] Cite error: The named reference Gerber was invoked but never defined (see the help page).

[5] "geosmin". Merriam-Webster Dictionary. 22 May 2023.

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