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Merck

UC18

Sigma-Aldrich

(±)-Geosmin

≥97% (GC), liquid (oil)

Sinónimos:

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

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5 MG
MXP 11,894.00
10 MG
MXP 19,887.00

MXP 11,894.00


Fecha estimada de envío23 de mayo de 2025


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5 MG
MXP 11,894.00
10 MG
MXP 19,887.00

About This Item

Fórmula empírica (notación de Hill):
C12H22O
Número de CAS:
Peso molecular:
182.30
Número MDL:
Código UNSPSC:
12161501
ID de la sustancia en PubChem:
NACRES:
NA.77

MXP 11,894.00


Fecha estimada de envío23 de mayo de 2025


Solicitar un pedido a granel

Nombre del producto

(±)-Geosmin, ≥97% (GC)

Ensayo

≥97% (GC)

Formulario

liquid (oil)

color

colorless

temp. de almacenamiento

2-8°C

cadena SMILES

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

Clave InChI

JLPUXFOGCDVKGO-UHFFFAOYSA-N

Aplicación

(±)-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].

Acciones bioquímicas o fisiológicas

(±)-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].

Pictogramas

Exclamation mark

Palabra de señalización

Warning

Frases de peligro

Clasificaciones de peligro

Eye Irrit. 2

Código de clase de almacenamiento

10 - Combustible liquids

Clase de riesgo para el agua (WGK)

WGK 3

Punto de inflamabilidad (°F)

Not applicable

Punto de inflamabilidad (°C)

Not applicable

Equipo de protección personal

dust mask type N95 (US), Eyeshields, Gloves


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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
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
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
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

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.

      Helpful?

  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.

      Helpful?

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