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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:
Molecular Weight:
182.30
MDL number:
UNSPSC Code:
12161501
PubChem Substance ID:
NACRES:
NA.77

product name

(±)-Geosmin, ≥97% (GC)

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

Signal Word

Warning

Hazard Statements

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

Certificates of Analysis (COA)

Search for Certificates of Analysis (COA) by entering the products Lot/Batch Number. Lot and Batch Numbers can be found on a product’s label following the words ‘Lot’ or ‘Batch’.

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Nayra Rodrigues de Alcântara et al.
Applied microbiology and biotechnology, 104(11), 5065-5080 (2020-04-08)
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Xiao Xu et al.
Molecules (Basel, Switzerland), 24(4) (2019-02-17)
Glutinous rice-based foods have a long history are consumed worldwide. They are also in great demand for the pursuit of novel sensory and natural health benefits. In this study, we developed a novel fermented glutinous rice product with the supplementation
Flávio Henrique Jesus-Santos et al.
Frontiers in cellular and infection microbiology, 10, 408-408 (2020-09-10)
On the surface of the Leishmania promastigote, phosphoglycans (PG) such as lipophosphoglycan (LPG), proteophosphoglycan (PPG), free phosphoglycan polymers (PGs), and acid phosphatases (sAP), are dominant and contribute to the invasion and survival of Leishmania within the host cell by modulating
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
Bertolt Gust et al.
Proceedings of the National Academy of Sciences of the United States of America, 100(4), 1541-1546 (2003-02-04)
Streptomycetes are high G+C Gram-positive, antibiotic-producing, mycelial soil bacteria. The 8.7-Mb Streptomyces coelicolor genome was previously sequenced by using an ordered library of Supercos-1 clones. Here, we describe an efficient procedure for creating precise gene replacements in the cosmid clones

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