GEOSMIN

Details

Stereochemistry	ABSOLUTE
Molecular Formula	C12H22O
Molecular Weight	182.3025
Optical Activity	UNSPECIFIED
Defined Stereocenters	3 / 3
E/Z Centers	0
Charge	0

SHOW SMILES / InChI

Structure Search

SMILES

C[C@H]1CCC[C@@]2(C)CCCC[C@]12O

InChI

InChIKey=JLPUXFOGCDVKGO-TUAOUCFPSA-N

InChI=1S/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

HIDE SMILES / InChI

Molecular Formula	C12H22O
Molecular Weight	182.3025
Charge	0
Count

Stereochemistry	ABSOLUTE
Additional Stereochemistry	No
Defined Stereocenters	3 / 3
E/Z Centers	0
Optical Activity	UNSPECIFIED

Description
Sources: https://www.ncbi.nlm.nih.gov/pubmed/28414956 | http://web.expasy.org/spotlight/back_issues/035/ | https://www.sigmaaldrich.com/content/dam/sigma-aldrich/docs/Aldrich/Product_Information_Sheet/g5908pis.pdf | http://www.chm.bris.ac.uk/motm/geosmin/geosminh.htm

Geosmin is a germacranoid sesquiterpene or a trans-1,10-dimethyl-trans-9-decalol. Geosmin, an earthy-smelling substance, has been isolated from several actinomycetes. 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. Geosmin is used to confer an earthy scent to perfumes.

CNS Activity

Originator

Approval Year

Conditions

Condition	Modality	Targets	Highest Phase	Product
Unknown 2578

PubMed

Title	Date	PubMed
Identification of geosmin as a volatile metabolite of Anabaena sp.	2001	11314247
Environmental and nutritional factors affecting geosmin synthesis by Anabaena sp.	2001 Apr	11268841
1-Octen-3-ol together with geosmin: new secretion compounds from a polydesmid millipede, Niponia nodulosa.	2002 Dec	12564803
Influence of the character of NOM on the ozonation of MIB and geosmin.	2002 Feb	11827313
Physical and chemical properties of selected agricultural byproduct-based activated carbons and their ability to adsorb geosmin.	2002 Sep	12139335
The effect of oxidants on 2-MIB concentration with the presence of cyanobacteria.	2004	15237636
Removal of geosmin and 2-methylisoborneol by biological filtration.	2004	15237635
Synthesis and odour thresholds of mixed halogenated anisoles in water.	2004	15237615
Design and application of a GC-SNIff/MS system for solving taste and odour episodes in drinking water.	2004	15237611
Volatile organic compound (VOC) analysis and sources of limonene, cyclohexanone and straight chain aldehydes in axenic cultures of Calothrix and Plectonema.	2004	15237606
A guide to geosmin- and MIB-producing cyanobacteria in the United States.	2004	15237602
AOPs with ozone and UV radiation in drinking water: contaminants removal and effects on disinfection byproducts formation.	2004	15077947
Characterization of Penicillium species isolated from grape berries by their internal transcribed spacer (ITS1) sequences and by gas chromatography-mass spectrometry analysis of geosmin production.	2004 Jun	15170234
Cyanobacteria and earthy/musty compounds found in commercial catfish (Ictalurus punctatus) ponds in the Mississippi Delta and Mississippi--Alabama Blackland Prairie.	2005 Aug	15993924
Volatiles released by a Streptomyces species isolated from the North Sea.	2005 Jul	17193176
Determination of temperature-dependent Henry's law constants of odorous contaminants and their application to human perception.	2005 Jun 1	15984770
A novel type of geosmin biosynthesis in myxobacteria.	2005 Jun 24	15960521
Automated trace determination of earthy-musty odorous compounds in water samples by on-line purge-and-trap-gas chromatography-mass spectrometry.	2006 Dec 15	17055519
Routine analysis of off-flavor compounds in water at sub-part-per-trillion level by large-volume injection GC/MS with programmable temperature vaporizing inlet.	2006 Feb	16458343
Implications of sequential use of UV and ozone for drinking water quality.	2006 May	16635504
Actinomycetes in relation to taste and odour in drinking water: myths, tenets and truths.	2006 May	16600325
Cooperative biodegradation of geosmin by a consortium comprising three gram-negative bacteria isolated from the biofilm of a sand filter column.	2006 Oct	16965373
A CAPS test allowing a rapid distinction of Penicillium expansum among fungal species collected on grape berries, inferred from the sequence and secondary structure of the mitochondrial SSU-rRNA.	2006 Oct 1	16935376
A case study investigating the occurrence of geosmin and 2-methylisoborneol (MIB) in the surface waters of the Hinze Dam, Gold Coast, Australia.	2007	17489415
Validation of geosmin and 2-methyl-i-borneol analysis by CLSA-GC-FID method to obtain ISO-17025 accreditation.	2007 Aug	17725872
Determination of 2-methylisoborneol and geosmin produced by Streptomyces sp. and Anabaena PCC7120.	2007 Aug 22	17663564
Biodegradation rates of 2-methylisoborneol (MIB) and geosmin through sand filters and in bioreactors.	2007 Feb	17005238

Patents

Sample Use Guides

In Vivo Use Guide

Unknown

Route of Administration: Unknown

In Vitro Use Guide

The cytotoxicity of musty odor-emitting substances, geosmin (GM) and 2-methylisoborneol, at a concentration of 10 ng/L - 300 mg/L was investigated using cultured mammalian cells. These two compounds exhibited no cytotoxicity in either the colony-formation of human KB cells or WST-1 assays of human-, monkey-, and dog-derived cells. These results suggest that the maximum concentration (700 ng/L) of GM found in the water of Lake Shinji is not toxic.

Substance Class	Chemical Created by `admin` on `Fri Dec 15 19:52:25 GMT 2023` Edited by `admin` on `Fri Dec 15 19:52:25 GMT 2023`
Record UNII	MYW912WXJ4
Record Status	`Validated (UNII)`
Record Version

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Name

Type

Language

GEOSMIN

Common Name

English

1,10-DIMETHYL-9-DECALOL

Systematic Name

English

4A(2H)-NAPHTHALENOL, OCTAHYDRO-4,8A-DIMETHYL-

Systematic Name

English

4,8A-DIMETHYLOCTAHYDRONAPHTHALEN-4A(2H)-OL

Systematic Name

English

(4S,4AS,8AR)-OCTAHYDRO-4,8A-DIMETHYL-4A(2H)-NAPHTHALENOL

Common Name

English

GEOSMIN [MI]

Common Name

English

FEMA NO. 4682

Code

English

OCTAHYDRO-4,8A-DIMETHYL-4A(2H)-NAPHTHOL

Systematic Name

English

Code System Code Type Description

CHEBI

46702