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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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:
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Product Name
(±)-Geosmin, ≥97% (GC)
Quality Level
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
Related Categories
1 of 4
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 |
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]
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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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
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
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
Related Content
Global Trade Item Number
| SKU | GTIN |
|---|---|
| UC18-5MG | 04061837410222 |
| UC18-10MG | 04061837410215 |
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