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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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$586.00
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$777.00

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5 MG
$586.00
10 MG
$777.00

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

$586.00

In StockDetails

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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[1]. Geosmin has also been used to study its adsorption on activated carbon[2].

Biochem/physiol Actions

(±)-Geosmin is produced by Streptomyces coelicolor and cyanobacteria.[3]
Geosmin is a naturally occurring biomolecule that contributes to the earthy or musty flavor and odor in water supplies[4]. This water contaminant can be detected by humans at ng/l (parts per trillion) concentrations[5].

pictograms

Exclamation mark
GHS07

signalword

Warning

hcodes

H319

Hazard Classifications

Eye Irrit. 2

Storage Class

10 - Combustible liquids

wgk_germany

WGK 3

flash_point_f

Not applicable

flash_point_c

Not applicable

ppe

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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Nayra Rodrigues de Alcântara et al.
Applied microbiology and biotechnology, 104(11), 5065-5080 (2020-04-08)
Mycobacterium abscessus subsp. massiliense (Mycma) belongs to the Mycobacterium abscessus complex and is a rapidly growing non-tuberculous mycobacterium. The chronic pulmonary, skin, and soft tissue infections that it causes may be difficult to treat due to its intrinsic resistance to
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
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
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
E Halevas et al.
Journal of inorganic biochemistry, 191, 94-111 (2018-11-27)
Curcumin is a natural product with a broad spectrum of beneficial properties relating to pharmaceutical applications, extending from traditional remedies to modern cosmetics. The biological activity of such pigments, however, is limited by their solubility and bioavailability, thereby necessitating new
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Questions

1–2 of 2 Questions  

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

    1 answer

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

    1 answer

    1. 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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