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(±)-geosmin

Chemical Structure

General Material Information

Preferred name (±)-geosmin
Trivial Name rel-(4R,4aR,8aS)-Octahydro-4,8a-dimethyl-4a(2H)-naphthalenol
Short Description 2b,6a-dimethylbicyclo[4.4.0]decan-1b-ol
Formula C12 H22 O
CAS Number 16423-19-1
FDA UNII MYW912WXJ4
Nikkaji Number J3.785K
MDL MFCD00055578
NMR Predictor External link
Synonyms
  • 2b,6a- dimethyl bicyclo(4.4.0)decan-1b-ol
  • 2beta,6alpha- dimethyl bicyclo(4.4.0)decan-1beta-ol
  • 2b,6a- dimethyl bicyclo[4.4.0]decan-1b-ol
  • 2beta,6alpha- dimethyl bicyclo[4.4.0]decan-1beta-ol
  • 1,10-(E)- dimethyl-(E)-(9)-decalol
  • (E)-1,10-dimethyl-(E)-decalin-9-ol
  • 2b,6a- dimethylbicyclo(4.4.0)decan-1b-ol
  • 2beta,6alpha- dimethylbicyclo(4.4.0)decan-1beta-ol
  • 2b,6a- dimethylbicyclo[4.4.0]decan-1b-ol
  • 2beta,6alpha- dimethylbicyclo[4.4.0]decan-1beta-ol
  • (4R,4aR,8aS)-4,8a-dimethyl-1,2,3,4,5,6,7,8-octahydronaphthalen-4a-ol
  • 4a(2H)-Naphthalenol, octahydro-4,8a-dimethyl-, (4R,4aR,8aS)-rel-
  • 4aα(2H)-Naphthol, octahydro-4α,8aβ-dimethyl-, (±)-
  • 4a(2H)-Naphthalenol, octahydro-4,8a-dimethyl-, (4α,4aα,8aβ)-(±)-
  • 4a(2H)-Naphthalenol, octahydro-4,8a-dimethyl-, (4α,4aα,8aβ)-
  • rel-(4R,4aR,8aS)-Octahydro-4,8a-dimethyl-4a(2H)-naphthalenol
  • DL-Geosmin

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Literature & References

Leffingwell:Chirality or Article
(4R,4aR,8aS)-4,8a-dimethyl-1,2,3,4,5,6,7,8-octahydronaphthalen-4a-ol
NIST Chemistry WebBook:Search Inchi
Pubchem (cid):29746
Pubchem (sid):135339892
Publications by PubMed
Simultaneous determination of ten taste and odor compounds in drinking water by solid-phase microextraction combined with gas chromatography-mass spectrometry.
Analysis of Five Earthy-Musty Odorants in Environmental Water by HS-SPME/GC-MS.
A review on advanced oxidation processes for the removal of taste and odor compounds from aqueous media.
Earthy off-flavour in wine: evaluation of remedial treatments for geosmin contamination.
Geosmin (2β,6α-dimethylbicyclo[4.4.0]decan-1β-ol) production associated with Beta vulgaris ssp. vulgaris is cultivar specific.
Gas chromatography-mass spectrometry determination of earthy-musty odorous compounds in waters by two phase hollow-fiber liquid-phase microextraction using polyvinylidene fluoride fibers.
Salmeterol attenuates chemotactic responses in rhinovirus-induced exacerbation of allergic airways disease by modulating protein phosphatase 2A.
Effect of oxidant exposure on the release of intracellular microcystin, MIB, and geosmin from three cyanobacteria species.
Determination of off-flavor compounds, 2-methylisoborneol and geosmin, in salmon fillets using stir bar sorptive extraction-thermal desorption coupled with gas chromatography-mass spectrometry.
Volatile terpenes from actinomycetes: a biosynthetic study correlating chemical analyses to genome data.
Use of fuzzy logic models for prediction of taste and odor compounds in algal bloom-affected inland water bodies.
The native production of the sesquiterpene isopterocarpolone by Streptomyces sp. RM-14-6.
Prediction and characterization of small non-coding RNAs related to secondary metabolites in Saccharopolyspora erythraea.
Occurrence of earthy and musty odor compounds (geosmin, 2-methylisoborneol and 2,4,6-trichloroanisole) in biologically treated wastewater.
Description of the mechanisms underlying geosmin production in Penicillium expansum using proteomics.
Monitoring of geosmin producing Anabaena circinalis using quantitative PCR.
Aroma characterization of chinese rice wine by gas chromatography-olfactometry, chemical quantitative analysis, and aroma reconstitution.
Bioactivities of six sterols isolated from marine invertebrates.
Chemical compositions and muddy flavour/odour of protein hydrolysate from Nile tilapia and broadhead catfish mince and protein isolate.
Orthogonal Design Study on Factors Affecting the Determination of Common Odors in Water Samples by Headspace Solid-Phase Microextraction Coupled to GC/MS.
Pachydictyols B and C: new diterpenes from Dictyota dichotoma Hudson.
Oxygenation of ruthenium carbene complexes containing naphthothiophene or naphthofuran: spectroscopic and DFT studies.
The structures of two aldazines: [1,1'-(1E,1'E)-hydrazine-1,2-diylidenebis(methan-1-yl-1-ylidene)dinaphthalen-2-ol] (Lumogen) and 2,2'-(1E,1'E)-hydrazine-1,2-diylidenebis(methan-1-yl-1-ylidene)diphenol (salicylaldazine) in the solid state and in solution.
Using digital flow cytometry to assess the degradation of three cyanobacteria species after oxidation processes.
Grapevine bunch rots: impacts on wine composition, quality, and potential procedures for the removal of wine faults.
Establishment of quantitative PCR methods for the quantification of geosmin-producing potential and Anabaena sp. in freshwater systems.
Kinetics and molecular docking studies of pimarane-type diterpenes as protein tyrosine phosphatase (PTP1B) inhibitors from Aralia continentalis roots.
Transcriptomic analysis of Streptomyces coelicolor differentiation in solid sporulating cultures: first compartmentalized and second multinucleated mycelia have different and distinctive transcriptomes.
From discrete monomeric complexes to hydrogen-bonded dimeric assemblies based on sterically encumbered square planar palladium(II) ONN-pincers.
Geosmin and 2-methylisoborneol removal using superfine powdered activated carbon: shell adsorption and branched-pore kinetic model analysis and optimal particle size.
Community of environmental streptomyces related to geosmin development in Chinese liquors.
Detection and quantification of natural contaminants of wine by gas chromatography-differential ion mobility spectrometry (GC-DMS).
Quantitative analysis of earthy and musty odors in drinking water sources impacted by wastewater and algal derived contaminants.
In vivo solid-phase microextraction with in vitro calibration: determination of off-flavor components in live fish.
Neuroecology: a fly's bug detector.
Impact of water quality on the bacterial populations and off-flavours in recirculating aquaculture systems.
A conserved dedicated olfactory circuit for detecting harmful microbes in Drosophila.
Metabolic characteristics of the species Variovorax paradoxus.
Inhibitory activity of Aralia continentalis roots on protein tyrosine phosphatase 1B and rat lens aldose reductase.
A framework for identifying characteristic odor compounds in municipal wastewater effluent.
Evaluation of a modified pH-shift process to reduce 2-methylisoborneol and geosmin in spiked catfish and produce a consumer acceptable fried catfish nugget-like product.
Determination of rate constants and half-lives for the simultaneous biodegradation of several cyanobacterial metabolites in Australian source waters.
UV-based advanced oxidation processes for the treatment of odour compounds: efficiency and by-product formation.
Earthy odor compounds production and loss in three cyanobacterial cultures.
Accurate analysis of trace earthy-musty odorants in water by headspace solid phase microextraction gas chromatography-mass spectrometry.
Sesquiterpenes and an intermediate 1alpha, 6beta, 11-eudesmanetriol in the biosynthesis of geosmin from Streptomyces sp.
Protein tyrosine phosphatase 1B inhibitory activity of Indonesian herbal medicines and constituents of Cinnamomum burmannii and Zingiber aromaticum.
[Influence of nutrient sources on Anabaena spiroides growth and odorous compounds production characteristics].
[Biosynthesis of geosmin and 2-methylisoborneol in the prokaryotes--a review].
Identification of host genes showing differential expression profiles with cell-based long-term replication of hepatitis C virus RNA.
Spatio-temporal variability of tastes and odors of drinking water within a distribution system.
Fate of cyanobacteria and their metabolites during water treatment sludge management processes.
Removal of cyanobacterial metabolites through wastewater treatment plant filters.
Biodegradation of multiple cyanobacterial metabolites in drinking water supplies.
Optimization of Fenton's reagent coupled to Dissolved Air Flotation to remove cyanobacterial odorous metabolites and suspended solids from raw surface water.
Determination of the microbial origin of geosmin in Chinese liquor.
Modelling geosmin concentrations in three sources of raw water in Quebec, Canada.
Terpenoids are widespread in actinomycetes: a correlation of secondary metabolism and genome data.
Synthesis of novel D-ring fused 7'-aryl-androstano[17,16-d][1,2,4] triazolo[1,5-a]pyrimidines.
Influence of various growth parameters on fungal growth and volatile metabolite production by indoor molds.
Microwave-assisted purge-and-trap extraction device coupled with gas chromatography and mass spectrometry for the determination of five predominant odors in sediment, fish tissues, and algal cells.
Biological treatment options for cyanobacteria metabolite removal--a review.
Isolation of bacteria capable of growth with 2-methylisoborneol and geosmin as the sole carbon and energy sources.
Establishment of a real-time PCR method for quantification of geosmin-producing Streptomyces spp. in recirculating aquaculture systems.
Presence, molecular characteristics and geosmin producing ability of actinomycetes isolated from South Korean terrestrial and aquatic environments.
Chemical and sensory quantification of geosmin and 2-methylisoborneol in rainbow trout (Oncorhynchus mykiss) from recirculated aquacultures in relation to concentrations in basin water.
Exploration and mining of the bacterial terpenome.
The management of undesirable cyanobacteria blooms in channel catfish ponds using a constructed wetland: Contribution to the control of off-flavor occurrences.
Odorous compounds in municipal wastewater effluent and potable water reuse systems.
Geosmin degradation by seasonal biofilm from a biological treatment facility.
Spatio-temporal distribution of cell-bound and dissolved geosmin in Wahnbach Reservoir: Causes and potential odour nuisances in raw water.
Biodegradation of geosmin in drinking water by novel bacteria isolated from biologically active carbon.
Adsorption of geosmin and 2-methylisoborneol onto powdered activated carbon at non-equilibrium conditions: influence of NOM and process modelling.
Characterization of geosmin as source of earthy odor in different aroma type Chinese liquors.
Isolation and identification of novel geosmin-degrading bacteria.
Effects of the origins of Botrytis cinerea on earthy aromas from grape broth media further inoculated with Penicillium expansum.
Simultaneous determination of eight common odors in natural water body using automatic purge and trap coupled to gas chromatography with mass spectrometry.
New developments in the analysis of fragrances and earthy-musty compounds in water by solid-phase microextraction (metal alloy fibre) coupled with gas chromatography-(tandem) mass spectrometry.
Treatment of taste and odor causing compounds 2-methyl isoborneol and geosmin in drinking water: a critical review.
Harmful algal blooms. Musty warnings of toxicity.
[Migration of main odorous compounds in a water supply system with Huangpu River as raw water in Shanghai].
Simultaneous degradation of disinfection byproducts and earthy-musty odorants by the UV/H2O2 advanced oxidation process.
Removal of cyanobacterial metabolites by nanofiltration from two treated waters.
Formation of assimilable organic carbon during oxidation of natural waters with ozone, chlorine dioxide, chlorine, permanganate, and ferrate.
Design and synthesis of potent HIV-1 protease inhibitors incorporating hexahydrofuropyranol-derived high affinity P(2) ligands: structure-activity studies and biological evaluation.
Determining human exposure and sensory detection of odorous compounds released during showering.
Investigating synergism during sequential inactivation of MS-2 phage and Bacillus subtilis spores with UV/H2O2 followed by free chlorine.
Determination of geosmin and 2-methylisoborneol in water and wine samples by ultrasound-assisted dispersive liquid-liquid microextraction coupled to gas chromatography-mass spectrometry.
Geosmin and 2-methylisoborneol adsorption on super-powdered activated carbon in the presence of natural organic matter.
Selectable one-dimensional or two-dimensional gas chromatography-olfactometry/mass spectrometry with preparative fraction collection for analysis of ultra-trace amounts of odor compounds.
A systematic study on spatial and seasonal patterns of eight taste and odor compounds with relation to various biotic and abiotic parameters in Gonghu Bay of Lake Taihu, China.
Diarylheptanoids from the Rhizomes of Curcuma kwangsiensis.
[Studies on the chemical constituents from the stems of Acanthopanax gracilistylus].
Cyanotoxin mixtures and taste-and-odor compounds in cyanobacterial blooms from the Midwestern United States.
Contribution of Streptomyces in sediment to earthy odor in the overlying water in Xionghe Reservoir, China.
Design, synthesis and docking studies on phenoxy-3-piperazin-1-yl-propan-2-ol derivatives as protein tyrosine phosphatase 1B inhibitors.
Analytical aspects of cyanobacterial volatile organic compounds for investigation of their production behavior.
In-tube extraction of volatile organic compounds from aqueous samples: an economical alternative to purge and trap enrichment.
Influence of water quality on the presence of off-flavour compounds (geosmin and 2-methylisoborneol).
Presynaptic dopaminergic agonists increased gripping-generated immobility episodes in the myelin-mutant taiep rat.
Microextraction and Gas Chromatography/Mass Spectrometry for improved analysis of geosmin and other fungal "off" volatiles in grape juice.
Biodegradation of MIB and geosmin with slow sand filters.
In situ measurement of odor compound production by benthic cyanobacteria.
Flying the fly: long-range flight behavior of Drosophila melanogaster to attractive odors.
Nanofiltration for the removal of algal metabolites and the effects of fouling.
Evaluation on simultaneous removal of particles and off-flavors using population balance for application of powdered activated carbon in dissolved air flotation process.
PROBES FOR NARCOTIC RECEPTOR MEDIATED PHENOMENA. 38. AN EXPEDITIOUS SYNTHESIS OF RAC-CIS-4a-ETHYL-2-METHYL-1,2,3,4,4a,9a-HEXAHYDROBENZOFURO[2,3-c]PYRIDIN-6-OL AND RAC-CIS-2-METHYL-4a-PHENETHYL-1,2,3,4,4a,9a-HEXAHYDROBENZOFURO[2,3-c]PYRIDIN-6-OL.
Comparison of batch sorption tests, pilot studies, and modeling for estimating GAC bed life.
Blue color formation of cyanobacteria with beta-cyclocitral.
Investigation of sensory and volatile characteristics of farmed and wild barramundi (Lates calcarifer) using gas chromatography-olfactometry mass spectrometry and descriptive sensory analysis.
Comparison of analytical techniques for detection of geosmin and 2-methylisoborneol in aqueous samples.
Removal of MIB and geosmin using granular activated carbon with and without MIEX pre-treatment.
Off-odor compounds produced in cork by isolated bacteria and fungi: a gas chromatography-mass spectrometry and gas chromatography-olfactometry study.
Synthesis of tetranuclear rhodium and iridium complexes directed by 6-mercaptopyridin-2-ol: electrochemical behavior, chemical oxidation, and coordination chemistry.
Optimising water treatment practices for the removal of Anabaena circinalis and its associated metabolites, geosmin and saxitoxins.
Biotransformations of (+/-)-geosmin by terpene-degrading bacteria.
Exploration of geosmin synthase from Streptomyces peucetius ATCC 27952 by deletion of doxorubicin biosynthetic gene cluster.
Neuronal adaptations, neuroendocrine and immune correlates of heroin self-administration.
Branched pore kinetic model analysis of geosmin adsorption on super-powdered activated carbon.
Biodegradation of geosmin by a novel Gram-negative bacterium; isolation, phylogenetic characterisation and degradation rate determination.
Development of predictive models for geosmin-related taste and odor in Kansas, USA, drinking water reservoirs.
[Review on the tastes and odors compounds in drinking water of China].
Evaluation of the cytotoxicity of geosmin and 2-methylisoborneol using cultured human, monkey, and dog cells.
Actinomycetes and earthy-musty odorous compounds in brackish fishponds in Tianjin, China.
Sesquiterpenes of the geosmin-producing cyanobacterium Calothrix PCC 7507 and their toxicity to invertebrates.
Photoinitiated oxidation of geosmin and 2-methylisoborneol by irradiation with 254 nm and 185 nm UV light.
Occurrence of dissolved and particle-bound taste and odor compounds in Swiss lake waters.
[Ozonation of odorous organic compounds in eutrophic water].
[Removal technology of typical odorant in drinking water].
Global sensitivity analysis for model-based prediction of oxidative micropollutant transformation during drinking water treatment.
Isolation and characterization of the gene associated with geosmin production in cyanobacteria.
Enhancing the biofiltration of geosmin by seeding sand filter columns with a consortium of geosmin-degrading bacteria.
2-Methylisoborneol and geosmin uptake by organic sludge derived from a recirculating aquaculture system.
Analysis of earthy and musty odors in water samples by solid-phase microextraction coupled with gas chromatography/ion trap mass spectrometry.
Identification of odorous compounds from nine fermentor-cultivated Streptomyces strains.
Design and synthesis of a metabolically stable and potent antitussive agent, a novel delta opioid receptor antagonist, TRK-851.
Cloning and functional characterization of the germacradienol synthase (spterp13) from Streptomyces peucetius ATCC 27952.
Identification of sesquiterpene synthases from Nostoc punctiforme PCC 73102 and Nostoc sp. strain PCC 7120.
[Source and fluctuation of trace geosmin and 2-MIB in drinking water of Shanghai].
Biochemistry and molecular genetics of the biosynthesis of the earthy odorant methylisoborneol in Streptomyces coelicolor.
Adsorption characteristics of selected pharmaceuticals and an endocrine disrupting compound-Naproxen, carbamazepine and nonylphenol-on activated carbon.
Enzymatic removal of off-flavors from apple juice.
Evidence of alpha1-adrenoceptor functional changes in omental arteries of patients with end-stage renal disease.
Determination of musty odorants, 2-methylisoborneol and geosmin, in environmental water by headspace solid-phase microextraction and gas chromatography--mass spectrometry.
Lysis of cyanobacteria with volatile organic compounds.
Geosmin biosynthesis. Mechanism of the fragmentation-rearrangement in the conversion of germacradienol to geosmin.
Identification of (8S,9S,10S)-8,10-dimethyl-1-octalin, a key intermediate in the biosynthesis of geosmin in bacteria.
Seasonal change and correlation with environmental parameters for 2-MIB in Feng-Shen Reservoir, Taiwan.
Microbially derived off-flavor from geosmin and 2-methylisoborneol: sources and remediation.
A facile and efficient synthesis of some (6E)-hydroximino-4-en-3-one steroids, steroidal oximes from Cinachyrella spp. sponges.
Digging for answers, smelling a hint of success and tasting triumph.
Biosynthesis of the earthy odorant geosmin by a bifunctional Streptomyces coelicolor enzyme.
Identification and expression analyses of putative sesquiterpene synthase genes in Phormidium sp. and prevalence of geoA-like genes in a drinking water reservoir.
Validation of geosmin and 2-methyl-i-borneol analysis by CLSA-GC-FID method to obtain ISO-17025 accreditation.
Determination of 2-methylisoborneol and geosmin produced by Streptomyces sp. and Anabaena PCC7120.
Growth behavior of off-flavor-forming microorganisms in apple juice.
Relationship between volatile odorous substances and production of avermectins by Streptomyces avermitilis.
Impact of the Botrytis cinerea strain and metabolism on (-)-geosmin production by Penicillium expansum in grape juice.
Synthesis and anti-proliferative in-vitro activity of two natural dihydrostilbenes and their analogues.
Needs and perspectives of odour research in the aquatic sciences.
Natural origins of off-flavours in fish related to feeding habits.
Ability of humans to smell geosmin, 2-MIB and nonadienal in indoor air when using contaminated drinking water.
A case study investigating the occurrence of geosmin and 2-methylisoborneol (MIB) in the surface waters of the Hinze Dam, Gold Coast, Australia.
A review of taste and odour events in Barcelona's drinking water area (1990-2004).
The Ontario Water Works Consortium: a functional model of source water management and understanding.
Modification of granular activated carbon surface by chitosan coating for geosmin removal: sorption performances.
Tacoma controls tastes and odours with ozone.
Comparison between ozone and ferrate in oxidising geosmin and 2-MIB in water.
Advanced treatment for taste and odour control in drinking water: case study of a pilot scale plant in Seoul, Korea.
Efficient taste and odour removal by water treatment plants around the Han River water supply system.
A fast stir bar sorptive extraction method for the analysis of geosmin and 2-methylisoborneol in source and drinking water.
Interlaboratory comparison of geosmin and 2-methylisoborneol in municipal tap water.
Annual dynamics and origins of the odorous compounds in the pilot experimental area of Lake Dianchi, China.
A comparison of biofilms from macrophytes and rocks for taste and odour producers in the St. Lawrence river.
Geosmin and MIB events in a new reservoir in southern California.
Off flavours in large waterbodies: physics, chemistry and biology in synchrony.
Ultrasonically induced degradation of 2-methylisoborneol and geosmin.
Total synthesis of gymnorrhizol, an unprecedented 15-membered macrocyclic polydisulfide from the Chinese mangrove Bruguiera gymnorrhiza.
Biochemical and ecological control of geosmin and 2-methylisoborneol in source waters.
Design and evaluation of hydraulic baffled-channel PAC contactor for taste and odor removal from drinking water supplies.
Evaluation of extracellular products and mutagenicity in cyanobacteria cultures separated from a eutrophic reservoir.
Minimally invasive anterior thoracotomy for routine lung cancer resection.
Analysis of off-flavor compounds in water at sub part per trillion level by GC/MS with programmable temperature vaporizer inlet.
Removal of geosmin and MIB by biofiltration--an investigation discriminating between adsorption and biodegradation.
Volatiles released by a Streptomyces species isolated from the North Sea.
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.
Characterization of aroma-active compounds in rainbow trout (Oncorhynchus mykiss) eliciting an off-odor.
Characterization of some mushroom and earthy off-odors microbially induced by the development of rot on grapes.
Geosmin biosynthesis in Streptomyces avermitilis. Molecular cloning, expression, and mechanistic study of the germacradienol/geosmin synthase.
Automated trace determination of earthy-musty odorous compounds in water samples by on-line purge-and-trap-gas chromatography-mass spectrometry.
Biodegradation rates of 2-methylisoborneol (MIB) and geosmin through sand filters and in bioreactors.
Cooperative biodegradation of geosmin by a consortium comprising three gram-negative bacteria isolated from the biofilm of a sand filter column.
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.
Solid-phase microextraction in the analysis of food taints and off-flavors.
Odor thresholds of microbially induced off-flavor compounds in apple juice.
Ozonation of algae and odor causing substances in eutrophic waters.
Geosmin biosynthesis. Streptomyces coelicolor germacradienol/germacrene D synthase converts farnesyl diphosphate to geosmin.
Microbial diversity associated with odor modification for production of fertilizers from chicken litter.
Implications of sequential use of UV and ozone for drinking water quality.
Actinomycetes in relation to taste and odour in drinking water: myths, tenets and truths.
Predicting the adsorption capacity and isotherm curvature of organic compounds onto activated carbons in natural waters.
Headspace solvent microextraction as a simple and highly sensitive sample pretreatment technique for ultra trace determination of geosmin in aquatic media.
Detection of activity among uncultured Actinobacteria in a drinking water reservoir.
Survey and significance of filamentous fungi from tap water.
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.
Determination of 2-methylisoborneol and geosmin in aqueous samples by static headspace-gas chromatography-mass spectrometry with ramped inlet pressure.
Abundance of actinobacteria and production of geosmin and 2-methylisoborneol in Danish streams and fish ponds.
Seasonal occurrence and degradation of 2-methylisoborneol in water supply reservoirs.
Panaxynol induces neurite outgrowth in PC12D cells via cAMP- and MAP kinase-dependent mechanisms.
Chloroethylclonidine reveals that alpha (1 A)-adrenoceptors mediate contraction in aorta of alpha (1 D)-adrenoceptor knockout mice.
Volatile organic compounds in natural biofilm in polyethylene pipes supplied with lake water and treated water from the distribution network.
Origin of (-)-geosmin on grapes: on the complementary action of two fungi, botrytis cinerea and penicillium expansum.
Electrochemical bromination of cholest-5-enes.
Cyanobacteria and earthy/musty compounds found in commercial catfish (Ictalurus punctatus) ponds in the Mississippi Delta and Mississippi--Alabama Blackland Prairie.
Determination of temperature-dependent Henry's law constants of odorous contaminants and their application to human perception.
A novel type of geosmin biosynthesis in myxobacteria.
Identification using versatile sampling and analytical methods of volatile compounds from Streptomyces albidoflavus grown on four humid building materials and one synthetic medium.
[Contrastive analysis of volatile oil from Serissa serissoides in different seasons].
Compost stability assessment using a secondary metabolite: geosmin.
Synthesis of new 2',3'-dideoxy-6',6'-difluoro-3'-thionucleoside from gem-difluorohomoallyl alcohol.
Geosmin occurrence in riverine cyanobacterial mats: is it causing a significant health hazard?
Treatment of taste and odor material by oxidation and adsorption.
The effect of oxidants on 2-MIB concentration with the presence of cyanobacteria.
Removal of geosmin and 2-methylisoborneol by biological filtration.
The effect of water quality and NOM character on the ozonation of MIB and geosmin.
Biofilm in water pipelines; a potential source for off-flavours in the drinking water.
Optimization of stir bar sorptive extraction applied to the determination of odorous compounds in drinking water.
Effects of chlorine and chloramines on earthy and musty odors in drinking water.
An analytical method for shipboard extraction of the odour compounds, 2-methylisoborneol and geosmin.
Synthesis and odour thresholds of mixed halogenated anisoles in water.
Design and application of a GC-SNIff/MS system for solving taste and odour episodes in drinking water.
The attribute rating test for sensory analysis.
Volatile organic compound (VOC) analysis and sources of limonene, cyclohexanone and straight chain aldehydes in axenic cultures of Calothrix and Plectonema.
Periphyton: a primary source of widespread and severe taste and odour.
Nuisance odours produced by benthic cyanobacteria in a Mediterranean river.
A guide to geosmin- and MIB-producing cyanobacteria in the United States.
Characterization of Penicillium species isolated from grape berries by their internal transcribed spacer (ITS1) sequences and by gas chromatography-mass spectrometry analysis of geosmin production.
Biotransformation of alpha-isomethylionone to 1-(2,6,6-trimethyl-2-cyclohexen-1-yl)propan-2-one.
AOPs with ozone and UV radiation in drinking water: contaminants removal and effects on disinfection byproducts formation.
Origins and implications of drinking water odours in lakes and reservoirs of British Columbia, Canada.
Relationship between intensity, concentration, and temperature for drinking water odorants.
Mechanism and stereochemistry of the germacradienol/germacrene D synthase of Streptomyces coelicolor A3(2).
New convergent synthesis of 1alpha,25-dihydroxyvitamin D3 and its analogues by Suzuki-Miyaura coupling between A-ring and C,D-ring parts.
Determination of geosmin, 2-methylisoborneol, and a musty-earthy odor in wheat grain by SPME-GC-MS, profiling volatiles, and sensory analysis.
Novel derivatives of 9,10-anthraquinone are selective algicides against the musty-odor cyanobacterium Oscillatoria perornata.
Synthesis, further biological evaluation and pharmacodynamics of newly discovered inhibitors of TNF-alpha production.
Cytochrome p450 complement (CYPome) of the avermectin-producer Streptomyces avermitilis and comparison to that of Streptomyces coelicolor A3(2).
IGSF11 gene, frequently up-regulated in intestinal-type gastric cancer, encodes adhesion molecule homologous to CXADR, FLJ22415 and ESAM.
High-affinity monoclonal antibodies for detection of the microbial metabolite, 2-methylisoborneol.
Analysis of off-flavors in the aquatic environment by stir bar sorptive extraction-thermal desorption-capillary GC/MS/olfactometry.
Odours from pulp mill effluent treatment ponds: the origin of significant levels of geosmin and 2-methylisoborneol (MIB).
Further exploration of 1-[2-[Bis-(4-fluorophenyl)methoxy]ethyl]piperazine (GBR 12909): role of N-aromatic, N-heteroaromatic, and 3-oxygenated N-phenylpropyl substituents on affinity for the dopamine and serotonin transporter.
Clionasterol: a potent inhibitor of complement component C1.
Biosynthetic origin of geosmin in red beets (Beta vulgaris L.).
Quantitative determination of geosmin in red beets (Beta vulgaris L.) using headspace solid-phase microextraction.
1-Octen-3-ol together with geosmin: new secretion compounds from a polydesmid millipede, Niponia nodulosa.
PCR-targeted Streptomyces gene replacement identifies a protein domain needed for biosynthesis of the sesquiterpene soil odor geosmin.
Expression and mechanistic analysis of a germacradienol synthase from Streptomyces coelicolor implicated in geosmin biosynthesis.
Effect of residual chlorine on the analysis of geosmin, 2-MIB and MTBE in drinking water using the SPME technique.
Feeding of [5,5-2H(2)]-1-desoxy-D-xylulose and [4,4,6,6,6-2H(5)]-mevalolactone to a geosmin-producing Streptomyces sp. and Fossombronia pusilla.
Access to enantiomerically pure intermediates for (-)-geosmin synthesis starting from (4aS,5S)-4,4a,5,6,7,8-hexahydro-5-hydroxy-4a-methylnaphthalen-2(3H)-one.
Chemical composition of shallot (Allium ascalonicum Hort.).
Freundlich adsorption isotherms of agricultural by-product-based powdered activated carbons in a geosmin-water system.
Physical and chemical properties of selected agricultural byproduct-based activated carbons and their ability to adsorb geosmin.
Identification of Streptomyces odor spectrum.
Volatile metabolites from actinomycetes.
A density-functional study of the mechanism for the diastereoselective epoxidation of chiral allylic alcohols by the titanium peroxy complexes.
Influence of the character of NOM on the ozonation of MIB and geosmin.
Application of low-temperature glassy carbon films in solid-phase microextraction.
Phospholipase D1b and D2a generate structurally identical phosphatidic acid species in mammalian cells.
Determination of trace amounts of off-flavor compounds in drinking water by stir bar sorptive extraction and thermal desorption GC-MS.
Stereochemically Controlled Synthesis of Ruthenium(II) Complexes Containing Bis(oxazolin-2'-yl)pyridine Ligands. X-ray Crystal Structures of trans-[RuCl(2)(PPh(3)){kappa(3)-N,N,N-(S,S)-(i)Pr-pybox}] and [RuCl(=C=C=CPh(2))(PPh(3)){kappa(3)-N,N,N-(S,S)-(i)Pr-pybox}][PF(6)] ((S,S)-(i)Pr-pybox= 2,6-Bis[4'-(S)-isopropyloxazolin-2'-yl]pyridine).
Effects of carbon source, phosphorus concentration, and several micronutrients on biomass and geosmin production by Streptomyces halstedii.
The determination of six taste and odour compounds in water using Ambersorb 572 and high resolution mass spectrometry.
Identification of geosmin as a volatile metabolite of Anabaena sp.
Failure of AH11110A to functionally discriminate between alpha(1)-adrenoceptor subtypes A, B and D or between alpha(1)- and alpha(2)-adrenoceptors.
The application of powdered activated carbon for MIB and geosmin removal: predicting PAC doses in four raw waters.
Environmental and nutritional factors affecting geosmin synthesis by Anabaena sp.
Increasing the sensitivity of piezoelectric odour sensors based on molecularly imprinted polymers.
Volatile compounds in the production of liquid beet sugar.
Identification and quantification of geosmin, an earthy odorant contaminating wines.
Using microwave distillation-solid-phase microextraction--gas chromatography--mass spectrometry for analyzing fish tissue.
Effect of chronic ethanol and withdrawal on the mu-opioid receptor- and 5-Hydroxytryptamine(1A) receptor-stimulated binding of [(35)S]Guanosine-5'-O-(3-thio)triphosphate in the fawn-hooded rat brain: A quantitative autoradiography study.
Autoradiography of receptor-activated G-proteins in post mortem human brain.
Dopamine D(1) receptor-mediated control of striatal acetylcholine release by endogenous dopamine.
Analysis of 2-methylisoborneol and geosmin in catfish by microwave distillation--solid-phase microextraction.
WB 4101-related compounds. 2. Role of the ethylene chain separating amine and phenoxy units on the affinity for alpha(1)-adrenoreceptor subtypes and 5-HT(1A) receptors.
Analysis of odorous compounds in water by isolation by closed-loop stripping with a multichannel silicone rubber trap followed by gas chromatography-mass spectrometry.
Toxicological effects of geosmin and 2-methylisoborneol on rainbow trout hepatocytes.
Fungal volatiles as indicators of food and feeds spoilage.
Determination of geosmin and 2-methylisoborneol in water using solid-phase microextraction and gas chromatography-chemical ionisation/electron impact ionisation-ion-trap mass spectrometry.
Qualitative identification of volatile metabolites from two fungi and three bacteria species cultivated on two media.
Stereochemistry of the biotransformation of 1-hexene and 2-methyl-1-hexene with rat liver microsomes and purified P450s of rats and humans.
Degradation of geosmin-like compounds by selected species of gram-positive bacteria.
Simultaneous quantification of serotonin, dopamine and noradrenaline levels in single frontal cortex dialysates of freely-moving rats reveals a complex pattern of reciprocal auto- and heteroreceptor-mediated control of release.
Penicillium discolor, a new species from cheese, nuts and vegetables.
Microwave distillation-solid phase adsorbent trapping device for the determination of off-flavors, geosmin and methylisoborneol, in catfish tissue below their rejection levels.
Geosmin and Related Volatiles in Bioreactor-Cultured Streptomyces citreus CBS 109.60.
Serotonin enhances gastric acid response to TRH analogue in dorsal vagal complex through 5-HT2 receptors in rats.
Volatile organic chemicals of a shore-dwelling cyanobacterial mat community.
Reactions of the vitamin E model compound 2,2,5,7,8-pentamethylchroman-6-ol with peroxyl radicals.
Identification of geosmin as a volatile metabolite of Penicillium expansum.
The effect of disinfectants on a geosmin-producing strain of Streptomyces griseus.
N-modified analogues of cocaine: synthesis and inhibition of binding to the cocaine receptor.
Effects of farnesol and the off-flavor derivative geosmin on Streptomyces tendae.
Synthesis and structural, conformational, and pharmacological study of some of esters derived from 3-phenethyl-3-azabicyclo[3.2.1]octan-8-beta-ol and the corresponding N-endo-methyl quaternary derivatives.
Variation of geosmin content in Anabaena cells and its relation to nitrogen utilization.
Studies on the earthy-musty odours in natural water (IV). Mechanism of earthy-musty odour production of actinomycetes.
Monoterpenes and microbial metabolites in the soil.
Structures, absolute configurations, and syntheses of volatile signals from three sympatric ant-lion species,Euroleon nostras, Grocus bore, andMyrmeleon formicarius (Neuroptera: Myrmeleontidae).
[Low molecular weight metabolites produced by various Penicillium species].
Volatile compounds in flavor-tainted fish from the Upper Wisconsin River.
Simplified method to quantify geosmin and 2-methylisoborneol concentrations in water and microbiological cultures.
Action of acid on oligoribonucleotide phosphotriester intermediates. Effect of released vicinal hydroxy functions.
Effect of Photon Fluence Rate and Specific Growth Rate on Geosmin Production of the Cyanobacterium Oscillatoria brevis (Kütz.) Gom.
Dynamics of the volatile organic substances associated with cyanobacteria and algae in a eutrophic shallow lake.
Adenosine deaminase inhibitors. Synthesis and biological evaluation of (+/-)-3,6,7,8-tetrahydro-3-[(2-hydroxyethoxy)methyl]imidazo[4,5-d] [1,3]diazepin-8-ol and some selected C-5 homologues of pentostatin.
Geosmin and 2-methylisoborneol from cyanobacteria in three water supply systems.
[Identification of volatile metabolites produced by blue-green algae, Oscillatoria splendida, O. amoena, O. geminata and Aphanizomenon sp].
Analgesic narcotic antagonists. 5. 7,7-Dimethyldihydrocodeinones and 7,7-dimethyldihydromorphinones.
Geosmin and methylisoborneol biosynthesis in streptomycetes. Evidence for an isoprenoid pathway and its absence in non-differentiating isolates.
Volatile substances from actinomycetes: their role in the odor pollution of water.
Reactions of 4beta,5-epoxy-5beta-androstan-3-ones with hydrogen fluoride in pyridine.
Production of geosmin in fermentors and extraction with an ion-exchange resin.
[Metabolites of an actinomyces Biwako-B strain, isolated from sediment in Lake Biwa. Identification of the odorous compounds, geosmin and 2-methylisoborneol, and analysis of fatty acids].
[Odorous compounds in water supplies: detection of geosmin from water of the southern basin of Lake Biwa].
[Odorous metabolite of an Actinomyces Biwako-B strain. Identification of Geosmin by combined gas chromatography-mass spectrometry].
[Constituents of an actinomyces isolated from sediment in Lake Biwa. Identification of geosmin, an earthy-smelling compound].
Bilirubin conjugates of human bile. Isolation of phenylazo derivatives of bile bilirubin.
Geosmin, an earthly-smelling substance isolated from actinomycetes.
Publications by Leffingwell & Associates
Flavor Properties of FEMA GRAS List 25 flavor chemicals

Other Information

(IUPAC):Atomic Weights of the Elements 2011 (pdf)
Videos:The Periodic Table of Videos
tgsc:Atomic Weights use for this web site
(IUPAC):Periodic Table of the Elements
CHEBI:View
CHEMBL:View
KEGG (GenomeNet):C16286
HMDB (The Human Metabolome Database):Search
VCF-Online:VCF Volatile Compounds in Food

PhysChem Properties

Material listed in food chemical codex No
Molecular weight 182.30653381348
Melting Point 78 to 82°C @ 760 mm Hg
Flash Point TCC Value 11.11 °C TCC
logP (o/w) 3.57
Shelf life 12 months (or longer if stored properly.)
Storage notes Store in cool, dry place in tightly sealed containers, protected from heat and light.
Solubility
alcohol Yes
water, 156.7 mg/L @ 25 °C (est) Yes

Organoleptic Properties

Odor Type: Earthy
earthy, humus, dirty
General comment At 0.01 % in dipropylene glycol. earthy soil humus dirt

Occurrences

Potential Uses

Applications
Odor purposes Earth, Earth

Safety Information

Safety information

Preferred SDS: View
European information :
Most important hazard(s):
Xi - Irritant
R 11 - Highly flammable.
R 36/38 - Irritating to skin and eyes.
S 02 - Keep out of the reach of children.
S 07/09 - Keep container tightly closed and in well-ventilated place.
S 16 - Keep away from sources of ignition - No Smoking.
S 24/25 - Avoid contact with skin and eyes.
S 26 - In case of contact with eyes, rinse immediately with plenty of water and seek medical advice.
S 37/39 - Wear suitable gloves and eye/face protection.
Hazards identification
Classification of the substance or mixture
GHS Classification in accordance with 29 CFR 1910 (OSHA HCS)
None found.
GHS Label elements, including precautionary statements
Pictogram
Hazard statement(s)
None found.
Precautionary statement(s)
None found.
Oral/Parenteral Toxicity:
Not determined
Dermal Toxicity:
Not determined
Inhalation Toxicity:
Not determined

Safety in use information

Category:
flavor and fragrance agents
RIFM Fragrance Material Safety Assessment: Search
IFRA Code of Practice Notification of the 49th Amendment to the IFRA Code of Practice

Safety references

EPI System: View
Chemical Carcinogenesis Research Information System:Search
AIDS Citations:Search
Cancer Citations:Search
Toxicology Citations:Search
EPA ACToR:Toxicology Data
EPA Substance Registry Services (SRS):Registry
Laboratory Chemical Safety Summary :29746
National Institute of Allergy and Infectious Diseases:Data
WISER:UN 1230
WGK Germany:1
(4R,4aR,8aS)-4,8a-dimethyl-1,2,3,4,5,6,7,8-octahydronaphthalen-4a-ol
Chemidplus:0016423191