The geosmin products listed by Sigma-Aldrich (CAS Registry number [16423-19-1]) are synthetic, and would be exactly a 50:50 mixture of the (+) and (-) isomers. Specifically, the natural (-) isomer is (4S,4aS,8aR)-4,8a-Dimethyl-1,2,3,4,5,6,7,8-octahydronaphthalen-4a-ol. Therefore, the unnatural (+) isomer (the mirror image) is (4R,4aR,8aS)-4,8a-Dimethyl-1,2,3,4,5,6,7,8-octahydronaphthalen-4a-ol.This information has not been confirmed by a specific rotation measurement or chiral analysis, but is known based on the method of preparation.
UC18
(±)-Geosmin
≥97% (GC), liquid (oil)
Synonym(s):
2β,6α-Dimethylbicyclo[4.4.0]decan-1β-ol
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| Size/SKU | Availability | Price |
|---|---|---|
5 mg | Please contact Customer Service for Availability | PLN 2,470.00 |
10 mg | Please contact Customer Service for Availability | PLN 3,120.00 |
About This Item
Empirical Formula (Hill Notation):
C12H22O
CAS Number:
Molecular Weight:
182.30
UNSPSC Code:
12161501
PubChem Substance ID:
NACRES:
NA.77
MDL number:
Assay:
≥97% (GC)
Form:
liquid (oil)
Product Name
(±)-Geosmin, ≥97% (GC)
Quality Segment
assay
≥97% (GC)
form
liquid (oil)
color
colorless
storage temp.
2-8°C
SMILES string
CC1CCCC2(C)CCCCC12O
InChI
1S/C12H22O/c1-10-6-5-8-11(2)7-3-4-9-12(10,11)13/h10,13H,3-9H2,1-2H3
InChI key
JLPUXFOGCDVKGO-UHFFFAOYSA-N
Application
(±)-Geosmin has been used as a standard for GC-MS based analytical techniques[1]. Geosmin has also been used to study its adsorption on activated carbon.
Biochem/physiol Actions
Geosmin is a naturally occurring biomolecule that contributes to the earthy or musty flavor and odor in water supplies[2]. This water contaminant can be detected by humans at ng/l (parts per trillion) concentrations[3].
(±)-Geosmin is produced by Streptomyces coelicolor and cyanobacteria.[4]
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This Item | |||
|---|---|---|---|
| form liquid (oil) | form liquid | form powder | form powder |
| assay ≥97% (GC) | assay 97% (CP) | assay ≥98% (HPLC) | assay ≥95% (HPLC) |
| Quality Level 200 | Quality Level - | Quality Level - | Quality Level - |
| storage temp. 2-8°C | storage temp. - | storage temp. −20°C | storage temp. −20°C |
| color colorless | color - | color white to beige | color white to beige |
signalword
Warning
hcodes
Hazard Classifications
Eye Irrit. 2
Storage Class
10 - Combustible liquids
wgk
WGK 3
flash_point_f
Not applicable
flash_point_c
Not applicable
ppe
dust mask type N95 (US), Eyeshields, Gloves
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What can you tell me about the stereochemistry of Sigma-Aldrich's (±)-Geosmin products?
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Transportation information can be found in Section 14 of the product's (M)SDS.To access the shipping information for this material, use the link on the product detail page for the product.
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