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
• Article Data: 4

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

Different sources of media describe the Uses of 16423-19-1 differently. You can refer to the following data:
1. Geosmin is a major volatile component of beet essence, also determined to be the potent earthy odor contaminant of fish, beans, water.
2. (±)-Geosmin solution is commonly used in the odorant removal/degradation studies in the water and food chemistry.
3. (±)-Geosmin has been used as a standard for GC-MS based analytical techniques. Geosmin has also been used to study its adsorption on activated carbon.

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

• 125107-08-6 (1aS,4aR,8aR)-1a,4a-Dimethyl-octahydro-1-oxa-cyclopropa[d]naphthalen-2-ol 
• 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 
• 878-55-7 1,4a-dimethyl-4,4a,5,6,7,8-hexahydro-3H-naphthalen-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 
• 125107-10-0 Toluene-4-sulfonic acid (1aS,4aR,8aR)-1a,4a-dimethyl-octahydro-1-oxa-cyclopropa[d]naphthalen-2-yl ester 
• 22249-39-4 1,4a-dimethyl-1α,8aα-epoxyperhydronaphthalen-2-one 
• 126370-59-0 Methanesulfonic acid (2S,4aR,8R,8aR)-8a-hydroxy-4a,8-dimethyl-decahydro-naphthalen-2-yl ester 

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.

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.