Details
| Stereochemistry | ABSOLUTE |
| Molecular Formula | C12H22O |
| Molecular Weight | 182.3025 |
| Optical Activity | UNSPECIFIED |
| Defined Stereocenters | 3 / 3 |
| E/Z Centers | 0 |
| Charge | 0 |
SHOW SMILES / InChI
SMILES
C[C@H]1CCC[C@@]2(C)CCCC[C@]12O
InChI
InChIKey=JLPUXFOGCDVKGO-TUAOUCFPSA-N
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
| Molecular Formula | C12H22O |
| Molecular Weight | 182.3025 |
| Charge | 0 |
| Count |
|
| Stereochemistry | ABSOLUTE |
| Additional Stereochemistry | No |
| Defined Stereocenters | 3 / 3 |
| E/Z Centers | 0 |
| Optical Activity | UNSPECIFIED |
Geosmin is a germacranoid sesquiterpene or a trans-1,10-dimethyl-trans-9-decalol. Geosmin, an earthy-smelling substance, has been isolated from several actinomycetes. Geosmin is a naturally occurring biomolecule that contributes to the earthy or musty flavor and odor in water supplies. This water contaminant can be detected by humans at ng/l (parts per trillion) concentrations. Geosmin is used to confer an earthy scent to perfumes.
CNS Activity
Approval Year
PubMed
| Title | Date | PubMed |
|---|---|---|
| Microbially derived off-flavor from geosmin and 2-methylisoborneol: sources and remediation. | 2008 |
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| Complete gene expression profiling of Saccharopolyspora erythraea using GeneChip DNA microarrays. | 2007-11-26 |
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| Digging for answers, smelling a hint of success and tasting triumph. | 2007-11 |
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| Biosynthesis of the earthy odorant geosmin by a bifunctional Streptomyces coelicolor enzyme. | 2007-11 |
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| Impact of the Botrytis cinerea strain and metabolism on (-)-geosmin production by Penicillium expansum in grape juice. | 2007-10 |
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| Determination of 2-methylisoborneol and geosmin produced by Streptomyces sp. and Anabaena PCC7120. | 2007-08-22 |
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| Growth behavior of off-flavor-forming microorganisms in apple juice. | 2007-08-08 |
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| Validation of geosmin and 2-methyl-i-borneol analysis by CLSA-GC-FID method to obtain ISO-17025 accreditation. | 2007-08 |
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| Ultrasonically induced degradation of 2-methylisoborneol and geosmin. | 2007-06 |
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| Design and evaluation of hydraulic baffled-channel PAC contactor for taste and odor removal from drinking water supplies. | 2007-05 |
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| Rapid headspace solid-phase microextraction/gas chromatographic/mass spectrometric assay for the quantitative determination of some of the main odorants causing off-flavours in wine. | 2007-02-02 |
|
| Biodegradation rates of 2-methylisoborneol (MIB) and geosmin through sand filters and in bioreactors. | 2007-02 |
|
| Removal of geosmin and MIB by biofiltration--an investigation discriminating between adsorption and biodegradation. | 2007-01 |
|
| Relationship between volatile odorous substances and production of avermectins by Streptomyces avermitilis. | 2007 |
|
| Needs and perspectives of odour research in the aquatic sciences. | 2007 |
|
| Ability of humans to smell geosmin, 2-MIB and nonadienal in indoor air when using contaminated drinking water. | 2007 |
|
| A case study investigating the occurrence of geosmin and 2-methylisoborneol (MIB) in the surface waters of the Hinze Dam, Gold Coast, Australia. | 2007 |
|
| A review of taste and odour events in Barcelona's drinking water area (1990-2004). | 2007 |
|
| The Ontario Water Works Consortium: a functional model of source water management and understanding. | 2007 |
|
| Modification of granular activated carbon surface by chitosan coating for geosmin removal: sorption performances. | 2007 |
|
| Tacoma controls tastes and odours with ozone. | 2007 |
|
| Comparison between ozone and ferrate in oxidising geosmin and 2-MIB in water. | 2007 |
|
| Advanced treatment for taste and odour control in drinking water: case study of a pilot scale plant in Seoul, Korea. | 2007 |
|
| Efficient taste and odour removal by water treatment plants around the Han River water supply system. | 2007 |
|
| A fast stir bar sorptive extraction method for the analysis of geosmin and 2-methylisoborneol in source and drinking water. | 2007 |
|
| Interlaboratory comparison of geosmin and 2-methylisoborneol in municipal tap water. | 2007 |
|
| Annual dynamics and origins of the odorous compounds in the pilot experimental area of Lake Dianchi, China. | 2007 |
|
| A comparison of biofilms from macrophytes and rocks for taste and odour producers in the St. Lawrence river. | 2007 |
|
| Geosmin and MIB events in a new reservoir in southern California. | 2007 |
|
| Off flavours in large waterbodies: physics, chemistry and biology in synchrony. | 2007 |
|
| Automated trace determination of earthy-musty odorous compounds in water samples by on-line purge-and-trap-gas chromatography-mass spectrometry. | 2006-12-15 |
|
| Characterization of aroma-active compounds in rainbow trout (Oncorhynchus mykiss) eliciting an off-odor. | 2006-12-13 |
|
| Characterization of some mushroom and earthy off-odors microbially induced by the development of rot on grapes. | 2006-11-29 |
|
| A CAPS test allowing a rapid distinction of Penicillium expansum among fungal species collected on grape berries, inferred from the sequence and secondary structure of the mitochondrial SSU-rRNA. | 2006-10-01 |
|
| Cooperative biodegradation of geosmin by a consortium comprising three gram-negative bacteria isolated from the biofilm of a sand filter column. | 2006-10 |
|
| Odor thresholds of microbially induced off-flavor compounds in apple juice. | 2006-08-09 |
|
| Geosmin biosynthesis in Streptomyces avermitilis. Molecular cloning, expression, and mechanistic study of the germacradienol/geosmin synthase. | 2006-08 |
|
| Solid-phase microextraction in the analysis of food taints and off-flavors. | 2006-08 |
|
| Geosmin biosynthesis. Streptomyces coelicolor germacradienol/germacrene D synthase converts farnesyl diphosphate to geosmin. | 2006-06-28 |
|
| Implications of sequential use of UV and ozone for drinking water quality. | 2006-05 |
|
| Actinomycetes in relation to taste and odour in drinking water: myths, tenets and truths. | 2006-05 |
|
| Survey and significance of filamentous fungi from tap water. | 2006-05 |
|
| Predicting the adsorption capacity and isotherm curvature of organic compounds onto activated carbons in natural waters. | 2006-03 |
|
| Detection of activity among uncultured Actinobacteria in a drinking water reservoir. | 2006-03 |
|
| Routine analysis of off-flavor compounds in water at sub-part-per-trillion level by large-volume injection GC/MS with programmable temperature vaporizing inlet. | 2006-02 |
|
| Headspace solvent microextraction as a simple and highly sensitive sample pretreatment technique for ultra trace determination of geosmin in aquatic media. | 2006-01 |
|
| Analysis of off-flavor compounds in water at sub part per trillion level by GC/MS with programmable temperature vaporizer inlet. | 2006 |
|
| Ozonation of algae and odor causing substances in eutrophic waters. | 2006 |
|
| Determination of 2-methylisoborneol and geosmin in aqueous samples by static headspace-gas chromatography-mass spectrometry with ramped inlet pressure. | 2005-12 |
|
| Volatiles released by a Streptomyces species isolated from the North Sea. | 2005-07 |
Patents
Sample Use Guides
In Vitro Use Guide
Curator's Comment: Concentration of geosmin above 75 ug/mL was cytotoxic to HepG2 cells.
The cytotoxicity of musty odor-emitting substances, geosmin (GM) and 2-methylisoborneol, at a concentration of 10 ng/L - 300 mg/L was investigated using cultured mammalian cells. These two compounds exhibited no cytotoxicity in either the colony-formation of human KB cells or WST-1 assays of human-, monkey-, and dog-derived cells. These results suggest that the maximum concentration (700 ng/L) of GM found in the water of Lake Shinji is not toxic.
| Substance Class |
Chemical
Created
by
admin
on
Edited
Mon Mar 31 19:59:45 GMT 2025
by
admin
on
Mon Mar 31 19:59:45 GMT 2025
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| Record UNII |
MYW912WXJ4
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| Record Status |
Validated (UNII)
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| Record Version |
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46702
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GEOSMIN
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DTXSID801024112
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MYW912WXJ4
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243-239-8
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m5705
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46703
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19700-21-1
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