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Sigma-Aldrich

(±)-Geosmin

≥97% (GC), liquid (oil)

Synonym(s):

2β,6α-Dimethylbicyclo[4.4.0]decan-1β-ol

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About This Item

Empirical Formula (Hill Notation):
C12H22O
CAS Number:
16423-19-1
Molecular Weight:
182.30
MDL number:
MFCD00055578
UNSPSC Code:
12161501
PubChem Substance ID:
24724647
NACRES:
NA.77

Product Name

(±)-Geosmin, ≥97% (GC)

Quality Level

200

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. Geosmin has also been used to study its adsorption on activated carbon.

Biochem/physiol Actions

(±)-Geosmin is produced by Streptomyces coelicolor and cyanobacteria.
Geosmin is a naturally occurring biomolecule that contributes to the earthy or musty flavor and odor in water supplies. This water contaminant can be detected by humans at ng/l (parts per trillion) concentrations.

Pictograms

Exclamation mark
GHS07

Signal Word

Warning

Hazard Statements

H319

Hazard Classifications

Eye Irrit. 2

Storage Class Code

10 - Combustible liquids

WGK

WGK 3

Flash Point(F)

Not applicable

Flash Point(C)

Not applicable

Personal Protective Equipment

dust mask type N95 (US), Eyeshields, Gloves

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Certificates of Analysis (COA)

Lot/Batch Number
BCCL6662
BCCK4185
BCCD7213
BCBW9452
BCBS9505V

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  1. Which document(s) contains shelf-life or expiration date information for a given product?

    If available for a given product, the recommended re-test date or the expiration date can be found on the Certificate of Analysis.

  2. How do I get lot-specific information or a Certificate of Analysis?

    The lot specific COA document can be found by entering the lot number above under the "Documents" section.

  3. How do I find price and availability?

    There are several ways to find pricing and availability for our products. Once you log onto our website, you will find the price and availability displayed on the product detail page. You can contact any of our Customer Sales and Service offices to receive a quote.  USA customers:  1-800-325-3010 or view local office numbers.

  4. What is the Department of Transportation shipping information for this product?

    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. 

  5. What can you tell me about the stereochemistry of Sigma-Aldrich's (±)-Geosmin products?

    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.

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    Ask a Scientist here.

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Adsorption of Geosmin and MIB on Activated Carbon Fibers-Single and Binary Solute System.
Srinivasan, R., and Sorial, G. A.
Water, Air, Soil Pollut., 9(3-4), 223-235 (2009)
O Antonoglou et al.
Materials science & engineering. C, Materials for biological applications, 99, 264-274 (2019-03-21)
Heterometal oxide nanoparticles of bioessential metals are shedding new light to nanoparticle-inspired bioapplications. Pairing bioreactive elements like copper and iron can affect the redox dynamic and biological profile of the nanomaterial. Given the complexity of physicochemical properties, biological activity and
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Biochemical and biophysical research communications, 522(1), 226-232 (2019-11-25)
In Escherichia coli, G/C-rich hairpin structure followed by a U-tract in the 3' region of the nascent RNA are crucial determinants for intrinsic or factor independent transcription termination. In mycobacteria, there is a scarcity of such intrinsic terminators. However, secondary
S W Lloyd et al.
Journal of agricultural and food chemistry, 47(1), 164-169 (1999-11-24)
The semivolatile cyclic alcohols 2-methylisoborneol (MIB) and geosmin (GSM) impart muddy or musty flavors to water and food products. A rapid quantitative analytical technique has been developed whereby microwave distillation is used to remove the volatile organic compounds from a
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