CAS 19700-21-1

Geosmin

Description:

Geosmin is a naturally occurring organic compound with the chemical formula C12H22O. It is a bicyclic alcohol that is primarily responsible for the earthy aroma often associated with soil and certain foods, such as beets. Geosmin is produced by various microorganisms, including actinobacteria and some fungi, during their metabolic processes. Its distinctive scent is detectable by humans at extremely low concentrations, making it a significant compound in the field of sensory science. Geosmin is not only important in environmental contexts but also has implications in food science, as it can influence the flavor profile of agricultural products. In terms of physical properties, geosmin is a colorless to pale yellow liquid with a relatively low boiling point and moderate solubility in water, which can vary based on environmental conditions. Its presence in water sources can lead to undesirable tastes and odors, prompting interest in water treatment processes. Overall, geosmin plays a crucial role in both ecological and culinary contexts, highlighting the intersection of chemistry and sensory perception.

Formula: C₁₂H₂₂O

InChI: InChI=1/C12H22O/c1-10-6-5-8-11(2)7-3-4-9-12(10,11)13/h10,13H,3-9H2,1-2H3/t10-,11+,12-/m0/s1

InChI key: InChIKey=JLPUXFOGCDVKGO-TUAOUCFPSA-N

SMILES: O[C@@]12[C@](C)(CCCC1)CCC[C@@H]2C

Synonyms:

• (-)-Geosmin
• (4S,4aS,8aR)-4,8a-dimethyloctahydronaphthalen-4a(2H)-ol
• (4S,4aS,8aR)-Octahydro-4,8a-dimethyl-4a(2H)-naphthalenol
• (4S-(4alpha,4aalpha,8abeta))-Octahydro-4,8a-dimethyl-4a(2H)-naphthol
• 4,8a-dimethyloctahydronaphthalen-4a(2H)-ol
• 4a(2H)-Naphthalenol, octahydro-4,8a-dimethyl-, (4S,4aS,8aR)-
• 4a(2H)-Naphthalenol, octahydro-4,8a-dimethyl-, (4S-(4-alpha,4a-alpha,8a-beta))-
• 4a(2H)-Naphthalenol, octahydro-4,8a-dimethyl-, [4S-(4α,4aα,8aβ)]-
• 4a-alpha-(2H)-Naphthol, octahydro-4-alpha,8a-beta-dimethyl- (8CI)
• 4aα(2H)-Naphthol, octahydro-4α,8aβ-dimethyl-
• Geonol
• 4a-alpha-(2H)-Naphthol, octahydro-4-alpha,8a-beta-dimethyl-
• geosmin,octahydro-4,8a-dimethyl-4a(2H)-Naphthalenol
• octahydro-4-alpha,8a-beta-dimethyl-4a-alpha-(2h)-naphtho
• 4a(2H)-Naphthalenol, octahydro-4,8a-dimethyl-,(4alpha,4aalpha,8abeta)-
• octahydro-4,8a-dimethyl-,(4s-(4-alpha,4a-alpha,8a-beta))-4a(2h)-naphthaleno
• [4S-(4α,4aα,8aβ)]-Octahydro-4,8a-dimethyl-4a(2H)-naphthol
• GEOSMINE
• 4,8a-Dimethyloctahydro-4a(2H)-naphthalenol
• GEOSMIN STANDARD
• 4a(2H)-Naphthalenol, octahydro-4,8a-dimethyl-, [4S-(4alpha,4aalpha,8abeta)]-

Geosmin

CAS: 19700-21-1

Applications Geosmin is an earthly odorant responsible for the strong scent (petrichor) that occurs in the air when rain falls after a dry spell of weather or when soil is disturbed.
References Jiang, J. et al.: Nat. Chem. Biol., 3, 711 (2007); Gerber, N.N. et al.: Appl. Microbiol., 13, 935 (1965);

Formula: C₁₂H₂₂O

Color and Shape: Neat

Molecular weight: 182.303

Ref: TR-G364600