16423-19-1

Basic information

• Product Name: (+/-)-GEOSMIN
• Synonyms: (+/-)-GEOSMIN;2BETA,6ALPHA-DIMETHYLBICYCLO[4.4.0]DECAN-1BETA-OL;TRANS-1,10-DIMETHYL-TRANSDECALIN-9-OL;(±)-geosmin solution;1,10-trans-dimethyl-trans-(9)-decalol;2β,6α-dimethylbicyclo[4.4.0]decan-1β-ol;(+/-) Geosmin Odor Standard;Geosmin (racemic), 95%
• CAS NO: 16423-19-1
• Molecular Formula: C₁₂H₂₂O
• Molecular Weight: 182.3
• EINECS: 200-659-6
• Product Categories: 500 Series Drinking Water Methods;EPA;Odor Standards;Chiral Reagents, Isotope Labelled Compounds
• Mol File: 16423-19-1.mol

Chemical Properties

• Boiling Point: 270°C at 760 mmHg
• Flash Point: 11 °C
• Appearance: colorless/
• Density: 0.985g/cm³
• Vapor Pressure: 0.000928mmHg at 25°C
• Refractive Index: 1.506
• Storage Temp.: 2-8°C
• PKA: 15.23±0.60(Predicted)
• CAS DataBase Reference: (+/-)-GEOSMIN(CAS DataBase Reference)
• NIST Chemistry Reference: (+/-)-GEOSMIN(16423-19-1)
• EPA Substance Registry System: (+/-)-GEOSMIN(16423-19-1)

Safety Data

• Hazard Codes: Xi,T,F
• Statements: 36-39/23/24/25-23/24/25-11
• Safety Statements: 26-45-36/37-16-7
• RIDADR: UN 1230 3/PG 2
• WGK Germany: 3
• Hazardous Substances Data: 16423-19-1(Hazardous Substances Data)

Usage

Uses

Used in Water and Food Chemistry:
(+/-)-GEOSMIN is used as an odorant in odorant removal and degradation studies in water and food chemistry. Its strong earthy odor makes it a useful tool for detecting and studying the presence of contaminants in these industries.
Used in Analytical Techniques:
(+/-)-GEOSMIN has been used as a standard for gas chromatography-mass spectrometry (GC-MS) based analytical techniques. This allows for the accurate identification and quantification of geosmin in various samples, such as water and food products.
Used in Adsorption Studies:
Geosmin has been used to study its adsorption on activated carbon. This research is important for understanding how to effectively remove geosmin and other contaminants from water and food products using activated carbon as an adsorbent.

Biochem/physiol Actions

(±)-Geosmin is produced by Streptomyces coelicolor and cyanobacteria.

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-/m1/s1

Upstream product

• 16423-16-8 trans-8,10-Dimethyl-1⁽⁹⁾-octalin 
• 126370-59-0 Methanesulfonic acid (2S,4aR,8R,8aR)-8a-hydroxy-4a,8-dimethyl-decahydro-naphthalen-2-yl ester 
• 22249-39-4 1,4a-dimethyl-1α,8aα-epoxyperhydronaphthalen-2-one 
• 125107-10-0 Toluene-4-sulfonic acid (1aS,4aR,8aR)-1a,4a-dimethyl-octahydro-1-oxa-cyclopropa[d]naphthalen-2-yl ester 
• 114200-73-6 (+/-)-perhydro-4aα,8β-dimethylnaphthalene-2β,8aβ-diol 
• 126370-57-8 (1R,2R,6S,9S)-2,11,11-Trimethyl-10,12-dioxa-tricyclo[7.3.1.0^1,6]tridecane-6-carbaldehyde 
• 17990-00-0 (4aα,8β)-4a,8-Dimethyl-4,4a,5,6,7,8-hexahydro-2(3H)-naphthalinon 
• 73428-93-0 1,4a-dimethyl-trans-3,4,4a,5,6,7,8,8a-otahydronaphthalen-8a-ol 
• 878-55-7 1,4a-dimethyl-4,4a,5,6,7,8-hexahydro-3H-naphthalen-2-one 
• 5173-65-9 (+/-)-1,10-Dimethyl-Δ¹⁽⁹⁾-octalin 
• 5173-67-1 1,10-Dimethyl-1⁽⁹⁾-octal-2-yl-acetat 
• 583-60-8 2-Methylcyclohexanone 
• 126370-55-6 (+/-)-3,4,4aα,5,6,7,8aβ-octahydro-8aβ-hydroxy-8β-methyl-2-oxo-1H-naphthalene-4aα-carbonitrile 
• 125107-08-6 (1aS,4aR,8aR)-1a,4a-Dimethyl-octahydro-1-oxa-cyclopropa[d]naphthalen-2-ol 

Downstream Products

• 16423-16-8 markiertes 8ref,10cis-Dimethyl-1(9)-octalin 

Relevant articles and documents

Synthesis of (+/-)-Geosmin. Part 2. A One-Pot Four-Step Conversion of 1,4a-Dimethyl-1α,8aα-epoxyperhydronaphthalen-2-one into (+/-)-Geosmin

A one-pot four-step procedure for the conversion of 1,4a-dimethyl-1α,8aα-epoxyperhydronaphthalen-2-one into (+/-)-geosmin is presented.The synthesis was achieved by a reduction-derivatization-double reduction sequence, which afforded the title compound in 35percent overall yield from ethyl vinyl ketone.Some other possible to (+/-)-geosmin have been investigated.A high yield synthesis of the C-1 epimer of (+/-)-geosmin using the same epoxide as the starting material is also described.Comparision with other previously reported total syntheses of the title compound is presented.

13. 1,2,3,4,4a,5,8,8a-Octahydro-4β,8aα-dimethylnaphthalen-4aβ-ol (=Dehydrogeosmin), a Novel Compound Occuring in the Flower Scent of Various Species of Cactaceae

The 1,2,3,4,4a,5,8,8a-octahydro-4β,8aα-dimethylnaphthalen-4aβ-ol (=dehydrogeosmin; 1) has been identified as the olfactorily dominant compound in the flower scents of Rebutia marsoneri WERD., Dolichothele longimamma (DC.) BR. et R., and Sulcorebutia kruegeri (CARD.) RITT.The structure of 1, which might be of importance to the pollination biology of such Cactaceae, is based on spectral data and synthesis.

SYNTHESIS OF EARTHY-MOULDY SMELLING COMPOUNDS-I STEREOSELECTIVE SYNTHESIS OF (+/-)-GEOSMIN

The strongly earthy-smelling compound (+/-)-geosmin 1 is obtained stereospecifically in four steps and 42percent overall yield from 1,4aβ-Dimethyl-4,4a,5,6,7,8-hexahydronaphtalen-2(3H)-one 2.The key step involves a one-pot double-reduction of an epoxytosylate.