Record Information
Version1.0
Creation date2010-04-08 22:11:47 UTC
Update date2018-01-23 19:40:27 UTC
Primary IDFDB015352
Secondary Accession NumbersNot Available
Chemical Information
FooDB NameGeosmin
DescriptionImplicated in off-flavour of shellfish, freshwater fish, drinking water and some vegetables Geosmin, which literally translates to "earth smell", is an organic compound with a distinct earthy flavour and aroma, and is responsible for the earthy taste of beets and a contributor to the strong scent that occurs in the air when rain falls after a dry spell of weather (petrichor) or when soil is disturbed. The human nose is extremely sensitive to geosmin and is able to detect it at concentrations as low as 5 parts per trillion. Geosmin is found in corn.
CAS Number19700-21-1
Structure
Thumb
Synonyms
SynonymSource
1,10-Dimethyl-9-decalolHMDB
11,12,13-Trinor-5-eudesmanolHMDB
4,8a-Dimethyloctahydro-4a(2H)-naphthalenolHMDB
4,8alpha-Dimethyl-octahydro-naphthalen-4alpha-olHMDB
Octahydro-4,8a-dimethyl-4a(2H)-naphthalenol, 9ciHMDB
Octahydro-4,8a-dimethyl-4a(2H)-naphthalenol, 9CIdb_source
Predicted Properties
PropertyValueSource
Water Solubility0.051 g/LALOGPS
logP3.66ALOGPS
logP3.17ChemAxon
logS-3.5ALOGPS
pKa (Strongest Basic)-0.0047ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count1ChemAxon
Hydrogen Donor Count1ChemAxon
Polar Surface Area20.23 ŲChemAxon
Rotatable Bond Count0ChemAxon
Refractivity54.58 m³·mol⁻¹ChemAxon
Polarizability22.19 ųChemAxon
Number of Rings2ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Chemical FormulaC12H22O
IUPAC name4,8a-dimethyl-decahydronaphthalen-4a-ol
InChI IdentifierInChI=1S/C12H22O/c1-10-6-5-8-11(2)7-3-4-9-12(10,11)13/h10,13H,3-9H2,1-2H3
InChI KeyJLPUXFOGCDVKGO-UHFFFAOYSA-N
Isomeric SMILESCC1CCCC2(C)CCCCC12O
Average Molecular Weight182.3025
Monoisotopic Molecular Weight182.167065326
Classification
Description belongs to the class of organic compounds known as tertiary alcohols. Tertiary alcohols are compounds in which a hydroxy group, -OH, is attached to a saturated carbon atom R3COH (R not H ).
KingdomOrganic compounds
Super ClassOrganic oxygen compounds
ClassOrganooxygen compounds
Sub ClassAlcohols and polyols
Direct ParentTertiary alcohols
Alternative Parents
Substituents
  • Tertiary alcohol
  • Cyclic alcohol
  • Hydrocarbon derivative
  • Aliphatic homopolycyclic compound
Molecular FrameworkAliphatic homopolycyclic compounds
External Descriptors
Physico-Chemical Properties - Experimental
Physico-Chemical Properties - Experimental
PropertyValueReference
Physical stateNot Available
Physical DescriptionNot Available
Mass CompositionC 79.06%; H 12.16%; O 8.78%DFC
Melting PointNot Available
Boiling PointBoiling Pt : 270 oC
Experimental Water SolubilityNot Available
Experimental logPNot Available
Experimental pKaNot Available
Isoelectric pointNot Available
ChargeNot Available
Optical Rotation[a]D -16.5 (CHCl3)DFC
Spectroscopic UV DataNot Available
DensityNot Available
Refractive IndexNot Available
Spectra
Spectra
Spectrum TypeDescriptionSplash Key
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-0udr-1900000000-73211b3533617178344cView in MoNA
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (1 TMS) - 70eV, Positivesplash10-01tj-3490000000-3ed4f0a4110d091adc8eView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0159-0900000000-f6d5dbada1d48ea6ad2cView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0159-2900000000-ced0e0d8d0358c61d547View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-059l-6900000000-380ea2bfec405ce5f64bView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-001i-0900000000-f5e30aaf3cdff12d77a2View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-001i-0900000000-4a166ae95fb9e5300392View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0gc9-1900000000-08145a39383b88307efdView in MoNA
ChemSpider ID1176
ChEMBL IDNot Available
KEGG Compound IDC16286
Pubchem Compound ID1213
Pubchem Substance IDNot Available
ChEBI ID46702
Phenol-Explorer IDNot Available
DrugBank IDNot Available
HMDB IDHMDB36461
CRC / DFC (Dictionary of Food Compounds) IDJZR98-B:JZR98-B
EAFUS IDNot Available
Dr. Duke IDGEOSMIN
BIGG IDNot Available
KNApSAcK IDC00013224
HET IDNot Available
Flavornet ID19700-21-1
GoodScent IDrw1454691
SuperScent IDNot Available
Wikipedia IDGeosmin
Phenol-Explorer Metabolite IDNot Available
Duplicate IDSNot Available
Old DFC IDSNot Available
Associated Foods
FoodContent Range AverageReference
FoodReference
Biological Effects and Interactions
Health Effects / BioactivitiesNot Available
EnzymesNot Available
PathwaysNot Available
MetabolismNot Available
BiosynthesisNot Available
Organoleptic Properties
Flavours
FlavorCitations
beet
  1. Arn, H, Acree TE. “Flavornet: A database of aroma compounds based on odor potency in natural products”. Developments in Food Science 40 (1998): 27. doi:10.1016/S0167-4501(98)80029-0
earth
  1. Arn, H, Acree TE. “Flavornet: A database of aroma compounds based on odor potency in natural products”. Developments in Food Science 40 (1998): 27. doi:10.1016/S0167-4501(98)80029-0
fresh
  1. The Good Scents Company (2009). Flavor and fragrance information catalog. <http://www.thegoodscentscompany.com/allprod.html> Accessed 15.10.23.
musty
  1. The Good Scents Company (2009). Flavor and fragrance information catalog. <http://www.thegoodscentscompany.com/allprod.html> Accessed 15.10.23.
earthy
  1. The Good Scents Company (2009). Flavor and fragrance information catalog. <http://www.thegoodscentscompany.com/allprod.html> Accessed 15.10.23.
soil
  1. The Good Scents Company (2009). Flavor and fragrance information catalog. <http://www.thegoodscentscompany.com/allprod.html> Accessed 15.10.23.
Files
MSDSNot Available
References
Synthesis ReferenceNot Available
General ReferenceNot Available
Content Reference— Duke, James. 'Dr. Duke's Phytochemical and Ethnobotanical Databases. United States Department of Agriculture.' Agricultural Research Service, Accessed April 27 (2004).