19700-21-1

Basic information

• Product Name: GEOSMIN
• Synonyms: 4,8a-Dimethyloctahydro-4a(2H)-naphthalenol;4a(2H)-Naphthalenol, octahydro-4,8a-dimethyl-, [4S-(4alpha,4aalpha,8abeta)]-;4a(2H)-Naphthalenol, octahydro-4,8a-dimethyl-,(4alpha,4aalpha,8abeta)-;4a-alpha-(2H)-Naphthol, octahydro-4-alpha,8a-beta-dimethyl-;octahydro-4,8a-dimethyl-,(4s-(4-alpha,4a-alpha,8a-beta))-4a(2h)-naphthaleno;octahydro-4-alpha,8a-beta-dimethyl-4a-alpha-(2h)-naphtho;GEOSMIN;[4S-(4alpha,4aalpha,8abeta)]-octahydro-4,8a-dimethyl-4a(2H)-naphthol
• CAS NO: 19700-21-1
• Molecular Formula: C₁₂H₂₂O
• Molecular Weight: 182.3
• EINECS: 243-239-8
• Product Categories: Pharmaceuticals, Intermediates & Fine Chemicals
• Mol File: 19700-21-1.mol
• Article Data: 11

Chemical Properties

• Boiling Point: bp 270°
• Flash Point: 104.2 °C
• Appearance: /
• Density: 0.985 g/cm³
• Vapor Pressure: 0.000928mmHg at 25°C
• Refractive Index: 1.506
• Storage Temp.: -20°C
• PKA: 15.23±0.60(Predicted)
• CAS DataBase Reference: GEOSMIN(CAS DataBase Reference)
• NIST Chemistry Reference: GEOSMIN(19700-21-1)
• EPA Substance Registry System: GEOSMIN(19700-21-1)

Safety Data

• Hazardous Substances Data: 19700-21-1(Hazardous Substances Data)

Usage

Description

GEOSMIN is an organic compound and an earthy odorant responsible for the distinct scent known as petrichor, which is experienced when rain falls after a dry period or when soil is disturbed. It is produced by various microorganisms, including bacteria, cyanobacteria, algae, and fungi, and can contribute to the odors of water supplies and food sources.

Uses

Used in Fragrance Industry:
GEOSMIN is used as a fragrance ingredient for its unique earthy scent, which can evoke the smell of rain on dry soil. This application is particularly useful in creating realistic and natural fragrances that mimic the scent of petrichor.
Used in Water Treatment:
GEOSMIN is used in the water treatment industry to detect and manage the presence of earthy smells in water supplies. Since geosmin is produced by microorganisms when nutrient production and dissolved oxygen are high, its presence can indicate potential issues with water quality.
Used in Food and Beverage Industry:
GEOSMIN is used in the food and beverage industry to enhance or recreate the earthy and fresh scent associated with petrichor. This can be particularly useful in products that aim to evoke a natural or outdoor experience, such as certain types of beverages, snacks, or even perfumes.
Used in Environmental Monitoring:
GEOSMIN can be used as an indicator in environmental monitoring to assess the presence and activity of microorganisms in soil and water ecosystems. High levels of geosmin production may suggest an overabundance of nutrients or changes in dissolved oxygen levels, which can inform environmental management strategies.

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/t10-,11+,12-/m0/s1

Synthetic route

Methanesulfonic acid (1aR,2S,4aS,8S,8aS)-4a,8-dimethyl-octahydro-1-oxa-cyclopropa[d]naphthalen-2-yl ester → (-)-geosmin (19700-21-1)

Conditions	Yield
With lithium aluminium tetrahydride In tetrahydrofuran for 3h; Heating;	90%

(+)-(4S,4aS,5R,8aS)-trans-4,8a-dimethyl-4a,5-epoxydecalin (169869-40-3) → (-)-geosmin (19700-21-1)

Conditions	Yield
With lithium aluminium tetrahydride In tetrahydrofuran at 60℃; for 1h;	64%

C14H24OS2 (60563-48-6) → (-)-geosmin (19700-21-1)

Conditions	Yield
With nickel In ethanol

/PBBEC010-1980/ → (-)-geosmin (19700-21-1)

Conditions	Yield
Multistep reaction;

farnesyl pyrophosphate (372-97-4, 13058-04-3, 25744-33-6, 27248-37-9, 27248-38-0, 40716-68-5) → (1S,4aS)-1,4a-Dimethyl-1,2,3,4,4a,5,6,8a-octahydro-naphthalene + (-)-geosmin (19700-21-1) + germacrene D (23986-74-5) + (–)-(4S,7R)-germacra-(1(10)E,5E)-dien-11-ol

Conditions	Yield
With Streptomyces coelicolor germacradienol synthase; Tris-Cl; magnesium chloride In water at 30℃; for 4h; Enzymatic reaction;

2,6-dimethylcyclohexanone (2816-57-1) → (-)-geosmin (19700-21-1)

Conditions	Yield
Multi-step reaction with 7 steps 1: 33 percent / H2SO4 / toluene 2: 83 percent / KOH / methanol / 1.5 h / Heating 3: 81 percent / LiAlH4 / diethyl ether / 3 h 4: 89 percent / pyridine / 24 h 5: Li, EtNH2 / 2 h / -5 °C 6: 73 percent / m-CPBA / CH2Cl2 / 2 h / 0 °C 7: 64 percent / LiAlH4 / tetrahydrofuran / 1 h / 60 °C View Scheme

(+)-4,8a-dimethyl-1,2,3,4,6,7,8,8a-octalin (125515-66-4) → (-)-geosmin (19700-21-1)

Conditions	Yield
Multi-step reaction with 2 steps 1: 73 percent / m-CPBA / CH2Cl2 / 2 h / 0 °C 2: 64 percent / LiAlH4 / tetrahydrofuran / 1 h / 60 °C View Scheme

(4aα,8β)-4a,8-Dimethyl-4,4a,5,6,7,8-hexahydro-2(3H)-naphthalinon (17990-00-0) → (-)-geosmin (19700-21-1)

Conditions	Yield
Multi-step reaction with 5 steps 1: 81 percent / LiAlH4 / diethyl ether / 3 h 2: 89 percent / pyridine / 24 h 3: Li, EtNH2 / 2 h / -5 °C 4: 73 percent / m-CPBA / CH2Cl2 / 2 h / 0 °C 5: 64 percent / LiAlH4 / tetrahydrofuran / 1 h / 60 °C View Scheme

6-hydroxy-4,8a-dimethyl-1,2,3,4,6,7,8,8a-octalin (52252-49-0, 97345-21-6, 97345-22-7) → (-)-geosmin (19700-21-1)

Conditions	Yield
Multi-step reaction with 4 steps 1: 89 percent / pyridine / 24 h 2: Li, EtNH2 / 2 h / -5 °C 3: 73 percent / m-CPBA / CH2Cl2 / 2 h / 0 °C 4: 64 percent / LiAlH4 / tetrahydrofuran / 1 h / 60 °C View Scheme

(E)-2,6-dimethyl-2-(3'-oxobutyl)cyclohexanone → (-)-geosmin (19700-21-1)

Conditions	Yield
Multi-step reaction with 6 steps 1: 83 percent / KOH / methanol / 1.5 h / Heating 2: 81 percent / LiAlH4 / diethyl ether / 3 h 3: 89 percent / pyridine / 24 h 4: Li, EtNH2 / 2 h / -5 °C 5: 73 percent / m-CPBA / CH2Cl2 / 2 h / 0 °C 6: 64 percent / LiAlH4 / tetrahydrofuran / 1 h / 60 °C View Scheme

6-acetoxy-4,8a-dimethyl-1,2,3,4,6,7,8,8a-octalin → (-)-geosmin (19700-21-1)

Conditions	Yield
Multi-step reaction with 3 steps 1: Li, EtNH2 / 2 h / -5 °C 2: 73 percent / m-CPBA / CH2Cl2 / 2 h / 0 °C 3: 64 percent / LiAlH4 / tetrahydrofuran / 1 h / 60 °C View Scheme

(2E,6E,10E)-3,7,11-trimethyl[12,12,12-2H3]dodeca-2,6,10-trienyl diphosphate (125951-22-6) → octalin (1004771-33-8) + [12,12,12-2H3]-germacrene D (1005386-38-8) + [12,12,12-2H3]-germacradienol (1005386-37-7) + (-)-geosmin (19700-21-1)

Conditions	Yield
With tris hydrochloride; magnesium chloride In water; glycerol at 30℃; for 6.25h; pH=8.2; Further byproducts. Title compound not separated from byproducts.;

(-)-geosmin (19700-21-1) → 3,5,5-Trimethylcyclohex-2-en-1-one (78-59-1) + 4a-methyl-4,4a,5,6,7,8-hexahydro-3H-naphthalen-2-one (826-56-2) + 2-ethylhexenal (645-62-5) + Octanoic acid (124-07-2) + 2-ethylcyclohexanone (4423-94-3) + Menthane (99-82-1, 1678-82-6, 6069-98-3, 129939-70-4, 129939-71-5) + 7a-methyl-1,4,5,6,7,7a-hexahydro-2H-inden-2-one (16508-51-3) + methyl 1-methylcyclohexyl ketone (2890-62-2) + 3-(2,6,6-trimethylcyclohex-2-enyl)propenal (29460-68-2) + 2,4-dimethylcyclopentane-1,3-dione (34598-80-6) + dihydrocarveol (619-01-2) + 8,8a-dimethyl-decahydronaphthalen-1-ol + 1-(2-methoxycyclohexyl)propan-2-one (95047-97-5) + 2,4,5,6-tetramethylhepta-1,3,6-triene + 1,8a-dimethyl-decahydronaphthalen-2-ol + (1,2-dimethylcyclopentyl)methanol + 3-Acetyl-5,5-dimethylcyclohexanone + octahydro-8a-hydroxy-4a-methyl-2(1H)-naphthalenone (40573-27-1)

Conditions	Yield
With oxygen; titanium(IV) oxide In water at 20℃; for 0.5h; Kinetics; UV-irradiation;

...Expand

(-)-geosmin (19700-21-1) → 4a-methyl-4,4a,5,6,7,8-hexahydro-3H-naphthalen-2-one (826-56-2) + 2-ethylhexenal (645-62-5) + 2-ethylcyclohexanone (4423-94-3) + Menthane (99-82-1, 1678-82-6, 6069-98-3, 129939-70-4, 129939-71-5) + 2,2-dimethyl-cyclohexanone (1193-47-1) + 2,2,6-trimethylcyclohexan-1-one (2408-37-9) + methyl 1-methylcyclohexyl ketone (2890-62-2) + 3-(2,6,6-trimethylcyclohex-2-enyl)propenal (29460-68-2) + dihydrocarveol (619-01-2) + 8,8a-dimethyl-decahydronaphthalen-1-ol + 1-(2-methoxycyclohexyl)propan-2-one (95047-97-5) + 2,4,5,6-tetramethylhepta-1,3,6-triene + 1,8a-dimethyl-decahydronaphthalen-2-ol + cyclohexanone (108-94-1) + (1,2-dimethylcyclopentyl)methanol + octahydro-8a-hydroxy-4a-methyl-2(1H)-naphthalenone (40573-27-1) + 3,5-dimethyl-3-cyclohexenylcarboxaldehyde

Conditions	Yield
With silicadodecatungstate; oxygen In water at 20℃; for 2h; Kinetics; UV-irradiation;

...Expand

Upstream product

• 125951-22-6 (2E,6E,10E)-3,7,11-trimethyl[12,12,12-2H₃]dodeca-2,6,10-trienyl diphosphate 
• 878-55-7 1,4a-dimethyl-4,4a,5,6,7,8-hexahydro-3H-naphthalen-2-one 
• 583-60-8 2-Methylcyclohexanone 
• 5173-67-1 1,10-Dimethyl-1⁽⁹⁾-octal-2-yl-acetat 
• 5173-65-9 (+/-)-1,10-Dimethyl-Δ¹⁽⁹⁾-octalin 
• 22249-39-4 1,4a-dimethyl-1α,8aα-epoxyperhydronaphthalen-2-one 
• 73428-93-0 1,4a-dimethyl-trans-3,4,4a,5,6,7,8,8a-otahydronaphthalen-8a-ol 
• 17990-00-0 (4aα,8β)-4a,8-Dimethyl-4,4a,5,6,7,8-hexahydro-2(3H)-naphthalinon 
• 126370-57-8 (1R,2R,6S,9S)-2,11,11-Trimethyl-10,12-dioxa-tricyclo[7.3.1.0^1,6]tridecane-6-carbaldehyde 
• 126370-55-6 (+/-)-3,4,4aα,5,6,7,8aβ-octahydro-8aβ-hydroxy-8β-methyl-2-oxo-1H-naphthalene-4aα-carbonitrile 
• 126370-56-7 (+/-)-perhydro-7β,8aβ-dihydroxy-1β-methylnaphthalene-4aα-carbaldehyde 
• 114200-73-6 (+/-)-perhydro-4aα,8β-dimethylnaphthalene-2β,8aβ-diol 
• 125107-08-6 (1aS,4aR,8aR)-1a,4a-Dimethyl-octahydro-1-oxa-cyclopropa[d]naphthalen-2-ol 
• 125107-10-0 Toluene-4-sulfonic acid (1aS,4aR,8aR)-1a,4a-dimethyl-octahydro-1-oxa-cyclopropa[d]naphthalen-2-yl ester 

Downstream Products

• 16423-16-8 markiertes 8ref,10cis-Dimethyl-1(9)-octalin 
• 826-56-2 4a-methyl-4,4a,5,6,7,8-hexahydro-3H-naphthalen-2-one 
• 645-62-5 2-ethylhexenal 
• 4423-94-3 2-ethylcyclohexanone 
• 99-82-1 Menthane 
• 1193-47-1 2,2-dimethyl-cyclohexanone 
• 2408-37-9 2,2,6-trimethylcyclohexan-1-one 
• 2890-62-2 methyl 1-methylcyclohexyl ketone 
• 29460-68-2 3-(2,6,6-trimethylcyclohex-2-enyl)propenal 
• 619-01-2 dihydrocarveol 
• 95047-97-5 1-(2-methoxycyclohexyl)propan-2-one 
• 108-94-1 cyclohexanone 
• 40573-27-1 octahydro-8a-hydroxy-4a-methyl-2(1H)-naphthalenone 
• 68039-48-5 3,5-dimethyl-3-cyclohexenylcarboxaldehyde 

Related news

Parameters influencing elimination of GEOSMIN (cas 19700-21-1) and 2-methylisoborneol by K2FeO409/08/2019

Geosmin (GSM) and 2-methylisoborneol (2-MIB) are the most common naturally occurring taste and odor compounds in water supplies. Conventional approaches for water treatment exhibit some benefits. However, those protocols are generally ineffective for the elimination of the two compounds. In this...detailed

Degradation mechanisms of GEOSMIN (cas 19700-21-1) and 2-MIB during UV photolysis and UV/chlorine reactions09/07/2019

We conducted chlorination, UV photolysis, and UV/chlorin reactions to investigate the intermediate formation and degradation mechanisms of geosmin and 2-methylisoborneol (2-MIB) in water. Chlorination hardly removed geosmin and 2-MIB, while the UV/chlorine reaction at 254 nm completely removed g...detailed

The diversity, origin, and evolutionary analysis of GEOSMIN (cas 19700-21-1) synthase gene in cyanobacteria09/03/2019

The sesquiterpene geosmin, mainly originating from cyanobacteria, is considered one of the problematic odor compounds responsible for unpleasant-tasting and -smelling water episodes in freshwater supplies. The biochemistry and genetics of geosmin synthesis in cyanobacteria is well-elucidated and...detailed

Effective removal of MIB and GEOSMIN (cas 19700-21-1) using MBBR for drinking water treatment09/02/2019

Biodegradation is an effective method for the removal of taste and odour (T&O) compounds from drinking water sources. In this study, the applicability of a moving-bed biofilm reactor (MBBR) as biological treatment step for the control of MIB and geosmin was studied at pilot-scale. After a 3.5 mo...detailed

A fluorescence-displacement assay using molecularly imprinted polymers for the visual, rapid, and sensitive detection of the algal metabolites, GEOSMIN (cas 19700-21-1) and 2-methylisoborneol09/01/2019

A visual, rapid, and sensitive method for the detection of two algal metabolites, geosmin (GSM) and 2-methylisoborneol (2-MIB) using a competitive displacement technique based on molecular imprinted polymers (MIPs) and fluorescent tags was developed. In this method, fluorescent tags that bind to...detailed

Identification of GEOSMIN (cas 19700-21-1) biosynthetic gene in GEOSMIN (cas 19700-21-1)-producing colonial cyanobacteria Coelosphaerium sp. and isolation of GEOSMIN (cas 19700-21-1) non-producing Coelosphaerium sp. from brackish Lake Shinji in Japan08/31/2019

Geosmin is an earthy-muddy smelling compound produced in aquatic ecosystems by microorganisms including cyanobacteria. An increase in geosmin levels affecting the local fishery occurred in May 2007 in Lake Shinji, Japan, and geosmin-producing colonial cyanobacterium, Coelosphaerium sp. G2, was i...detailed

Relevant articles and documents

Geosmin biosynthesis. Streptomyces coelicolor germacradienol/germacrene D synthase converts farnesyl diphosphate to geosmin

Geosmin is responsible for the characteristic odor of moist soil. Incubation of recombinant germacradienol synthase, encoded by the SCO6073 (SC9B1.20) gene of the Gram-positive soil bacterium Streptomyces coelicolor, with farnesyl diphosphate (2, FPP) in the presence of Mg2+ gave a mixture of (4S,7R)-germacra-1(10)E,5E-diene-11-ol (3) (74%), (-)-(7S)-germacrene D (4) (10%), geosmin (1) (13%), and a hydrocarbon, tentatively assigned the structure of octalin 5 (3%). Individual incubations of recombinant germacradienol synthase with [1,1-2H2]FPP (2a), (1R)-[1-2H]-FPP (2b), and (1S)-[1-2H]-FPP (2c), as well as with FPP (2) in D2O, and GC-MS analysis of the resulting deuterated products supported a mechanism of geosmin formation involving proton-initiated cyclization and retro-Prins fragmentation of the initially formed germacradienol to give intermediate 5, followed by protonation of 5, 1,2-hydride shift, and capture of water. Copyright

Monolithic silicone and method of separation, purification and concentration therewith

The present invention provides a monolithic silicone in the form of an aerogel or a xerogel having flexibility and capable of dissolving molecules of a substance. This silicone monolithic body having continuous through passages is synthesized by copolymerizing starting materials of both a bifunctional alkoxysilane and a trifunctional alkoxysilane or tri- or higher functional alkoxysilanes through a sol-gel reaction for forming a Si—O network while causing phase separation.

AN EPOXY-TRINORREUDESMANE SESQUITERPENE FROM THE LIVERWORT LOPHOCOLEA BIDENTATA

A new epoxy-trinoreudesmane sesquiterpene, (+)-(4S,4aS,5R,8aS)-trans-4,8a-dimethyl-4a,5-epoxydecalin, was isolated from the liverwort Lophocolea bidentata, collected in northern Germany.The structure of this compound was elucidated by means of spectroscopic methods and by independent synthesis.The configuration was proved by enantioselective gas chromatography.The previously described olefinic precursor was also identified as a constituent. - Key words: Lophocolea bidentata; L. heterophylla; liverworts; sesquiterpenes; epoxy-trinoreudesmane; 4,8a-dimethyl-1,2,3,4,6,7,8,8a-octalin.