Record Information
Version1.0
Creation date2010-04-08 22:12:18 UTC
Update date2018-01-23 19:45:54 UTC
Primary IDFDB016218
Secondary Accession NumbersNot Available
Chemical Information
FooDB NameMenthyl isovalerate
DescriptionFlavouring ingredient with a bitter, wood-like taste. Menthyl isovalerate is found in peppermint.
CAS Number16409-46-4
Structure
Thumb
Synonyms
SynonymSource
Menthyl isovaleric acidGenerator
FEMA 2669HMDB
ValidolHMDB
(1R,2S,5R)-5-Methyl-2-(propan-2-yl)cyclohexyl 3-methylbutanoic acidGenerator
Validol, (1R-(1alpha,2beta,5alpha))-isomerMeSH
Validol, (1alpha,2beta,5alpha)-isomerMeSH
3-p-Menthyl isovalerateMeSH
(-)-Menthyl isovaleratemanual
Menthyl isovaleratedb_source
Predicted Properties
PropertyValueSource
Water Solubility0.003 g/LALOGPS
logP4.64ALOGPS
logP4.54ChemAxon
logS-4.9ALOGPS
pKa (Strongest Basic)-7ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count1ChemAxon
Hydrogen Donor Count0ChemAxon
Polar Surface Area26.3 ŲChemAxon
Rotatable Bond Count5ChemAxon
Refractivity70.37 m³·mol⁻¹ChemAxon
Polarizability29.55 ųChemAxon
Number of Rings1ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Chemical FormulaC15H28O2
IUPAC name(1R,2S,5R)-5-methyl-2-(propan-2-yl)cyclohexyl 3-methylbutanoate
InChI IdentifierInChI=1S/C15H28O2/c1-10(2)8-15(16)17-14-9-12(5)6-7-13(14)11(3)4/h10-14H,6-9H2,1-5H3/t12-,13+,14-/m1/s1
InChI KeyVYQSSWZYPCCBRN-HZSPNIEDSA-N
Isomeric SMILESCC(C)CC(=O)O[C@@H]1C[C@H](C)CC[C@H]1C(C)C
Average Molecular Weight240.3816
Monoisotopic Molecular Weight240.20893014
Classification
Description belongs to the class of organic compounds known as menthane monoterpenoids. These are monoterpenoids with a structure based on the o-, m-, or p-menthane backbone. P-menthane consists of the cyclohexane ring with a methyl group and a (2-methyl)-propyl group at the 1 and 4 ring position, respectively. The o- and m- menthanes are much rarer, and presumably arise by alkyl migration of p-menthanes.
KingdomOrganic compounds
Super ClassLipids and lipid-like molecules
ClassPrenol lipids
Sub ClassMonoterpenoids
Direct ParentMenthane monoterpenoids
Alternative Parents
Substituents
  • P-menthane monoterpenoid
  • Monocyclic monoterpenoid
  • Fatty acid ester
  • Fatty acyl
  • Carboxylic acid ester
  • Monocarboxylic acid or derivatives
  • Carboxylic acid derivative
  • Organic oxygen compound
  • Organic oxide
  • Hydrocarbon derivative
  • Organooxygen compound
  • Carbonyl group
  • Aliphatic homomonocyclic compound
Molecular FrameworkAliphatic homomonocyclic compounds
External DescriptorsNot Available
Ontology
OntologyShould have ontology for this compound
Physico-Chemical Properties - Experimental
Physico-Chemical Properties - Experimental
PropertyValueReference
Physical stateNot Available
Physical DescriptionNot Available
Mass CompositionC 74.95%; H 11.74%; O 13.31%DFC
Melting PointNot Available
Boiling PointBp22 140-146°DFC
Experimental Water SolubilityNot Available
Experimental logPNot Available
Experimental pKaNot Available
Isoelectric pointNot Available
ChargeNot Available
Optical RotationNot Available
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, Positivesplash10-0a4r-9410000000-20d3309958a96e8159baView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-000f-5690000000-58d938249b983d9a1f60View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0a4u-9400000000-c366cb5007bb4fb41f82View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0a4i-9100000000-4891817e2d7deda642fdView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-052r-2590000000-25bffb0452c80aa6923dView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0a4i-3920000000-359566a58414ed825da0View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0a4r-4900000000-73ec9cd3e036215cf704View in MoNA
ChemSpider ID107053
ChEMBL IDNot Available
KEGG Compound IDNot Available
Pubchem Compound ID119900
Pubchem Substance IDNot Available
ChEBI IDNot Available
Phenol-Explorer IDNot Available
DrugBank IDNot Available
HMDB IDHMDB37211
CRC / DFC (Dictionary of Food Compounds) IDJRL74-J:KOX36-X
EAFUS ID2157
Dr. Duke IDMENTHYL-ISOVALERATE
BIGG IDNot Available
KNApSAcK IDNot Available
HET IDNot Available
Flavornet IDNot Available
GoodScent IDrw1020381
SuperScent IDNot Available
Wikipedia IDNot Available
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
fruity
  1. The Good Scents Company (2009). Flavor and fragrance information catalog. <http://www.thegoodscentscompany.com/allprod.html> Accessed 15.10.23.
cooling
  1. The Good Scents Company (2009). Flavor and fragrance information catalog. <http://www.thegoodscentscompany.com/allprod.html> Accessed 15.10.23.
sweet
  1. The Good Scents Company (2009). Flavor and fragrance information catalog. <http://www.thegoodscentscompany.com/allprod.html> Accessed 15.10.23.
woody
  1. The Good Scents Company (2009). Flavor and fragrance information catalog. <http://www.thegoodscentscompany.com/allprod.html> Accessed 15.10.23.
bitter
  1. Ayana Wiener, Marina Shudler, Anat Levit, Masha Y. Niv. BitterDB: a database of bitter compounds. Nucleic Acids Res 2012, 40(Database issue):D413-419. DOI:10.1093/nar/gkr755
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).