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Record Information
Version5.0
StatusExpected but not Quantified
Creation Date2012-09-11 22:27:04 UTC
Update Date2022-03-07 02:55:14 UTC
HMDB IDHMDB0037211
Secondary Accession Numbers
  • HMDB37211
Metabolite Identification
Common NameMenthyl isovalerate
DescriptionMenthyl isovalerate 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. Based on a literature review a small amount of articles have been published on Menthyl isovalerate.
Structure
Data?1563862994
Synonyms
ValueSource
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
Chemical FormulaC15H28O2
Average Molecular Weight240.3816
Monoisotopic Molecular Weight240.20893014
IUPAC Name(1R,2S,5R)-5-methyl-2-(propan-2-yl)cyclohexyl 3-methylbutanoate
Traditional Name(1R,2S,5R)-2-isopropyl-5-methylcyclohexyl 3-methylbutanoate
CAS Registry Number16409-46-4
SMILES
CC(C)CC(=O)O[C@@H]1C[C@H](C)CC[C@H]1C(C)C
InChI Identifier
InChI=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
Chemical Taxonomy
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
Physiological effect
Disposition
Process
Role
Physical Properties
StateNot Available
Experimental Molecular Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling Point260.00 to 262.00 °C. @ 750.00 mm HgThe Good Scents Company Information System
Water Solubility0.31 mg/L @ 25 °C (est)The Good Scents Company Information System
LogP5.555 (est)The Good Scents Company Information System
Experimental Chromatographic PropertiesNot Available
Predicted Molecular 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
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleNoChemAxon
Predicted Chromatographic Properties

Predicted Collision Cross Sections

PredictorAdduct TypeCCS Value (Å2)Reference
DarkChem[M+H]+157.33131661259
DarkChem[M-H]-156.91131661259
DeepCCS[M+H]+172.42530932474
DeepCCS[M-H]-170.06730932474
DeepCCS[M-2H]-203.16330932474
DeepCCS[M+Na]+178.51830932474
AllCCS[M+H]+159.632859911
AllCCS[M+H-H2O]+156.232859911
AllCCS[M+NH4]+162.832859911
AllCCS[M+Na]+163.732859911
AllCCS[M-H]-164.832859911
AllCCS[M+Na-2H]-165.732859911
AllCCS[M+HCOO]-166.932859911

Predicted Kovats Retention Indices

Underivatized

MetaboliteSMILESKovats RI ValueColumn TypeReference
Menthyl isovalerateCC(C)CC(=O)O[C@@H]1C[C@H](C)CC[C@H]1C(C)C1702.0Standard polar33892256
Menthyl isovalerateCC(C)CC(=O)O[C@@H]1C[C@H](C)CC[C@H]1C(C)C1440.9Standard non polar33892256
Menthyl isovalerateCC(C)CC(=O)O[C@@H]1C[C@H](C)CC[C@H]1C(C)C1510.8Semi standard non polar33892256
Spectra

GC-MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Predicted GC-MSPredicted GC-MS Spectrum - Menthyl isovalerate GC-MS (Non-derivatized) - 70eV, Positivesplash10-0a4r-9410000000-20d3309958a96e8159ba2017-09-01Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Menthyl isovalerate GC-MS (Non-derivatized) - 70eV, PositiveNot Available2021-10-12Wishart LabView Spectrum

MS/MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Menthyl isovalerate 10V, Positive-QTOFsplash10-000f-5690000000-58d938249b983d9a1f602017-09-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Menthyl isovalerate 20V, Positive-QTOFsplash10-0a4u-9400000000-c366cb5007bb4fb41f822017-09-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Menthyl isovalerate 40V, Positive-QTOFsplash10-0a4i-9100000000-4891817e2d7deda642fd2017-09-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Menthyl isovalerate 10V, Negative-QTOFsplash10-052r-2590000000-25bffb0452c80aa6923d2017-09-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Menthyl isovalerate 20V, Negative-QTOFsplash10-0a4i-3920000000-359566a58414ed825da02017-09-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Menthyl isovalerate 40V, Negative-QTOFsplash10-0a4r-4900000000-73ec9cd3e036215cf7042017-09-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Menthyl isovalerate 10V, Positive-QTOFsplash10-0002-9100000000-f462aba699529497ed4b2021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Menthyl isovalerate 20V, Positive-QTOFsplash10-052n-9200000000-1b1658a7492e5cc434e92021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Menthyl isovalerate 40V, Positive-QTOFsplash10-0006-9000000000-1d4ccceaa876483fc6132021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Menthyl isovalerate 10V, Negative-QTOFsplash10-000i-0290000000-ab29b4f3b63e0a126d082021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Menthyl isovalerate 20V, Negative-QTOFsplash10-001i-9600000000-3aa3801ec84c36aebe9e2021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Menthyl isovalerate 40V, Negative-QTOFsplash10-067l-9500000000-3ee6d39922b667e4cd682021-09-22Wishart LabView Spectrum
Biological Properties
Cellular Locations
  • Extracellular
  • Membrane
Biospecimen LocationsNot Available
Tissue LocationsNot Available
Pathways
Normal Concentrations
Not Available
Abnormal Concentrations
Not Available
Associated Disorders and Diseases
Disease ReferencesNone
Associated OMIM IDsNone
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FooDB IDFDB016218
KNApSAcK IDNot Available
Chemspider ID107053
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkMenthyl isovalerate
METLIN IDNot Available
PubChem Compound119900
PDB IDNot Available
ChEBI IDNot Available
Food Biomarker OntologyNot Available
VMH IDNot Available
MarkerDB IDNot Available
Good Scents IDrw1020381
References
Synthesis ReferenceNot Available
Material Safety Data Sheet (MSDS)Not Available
General References
  1. Simons K, Toomre D: Lipid rafts and signal transduction. Nat Rev Mol Cell Biol. 2000 Oct;1(1):31-9. [PubMed:11413487 ]
  2. Watson AD: Thematic review series: systems biology approaches to metabolic and cardiovascular disorders. Lipidomics: a global approach to lipid analysis in biological systems. J Lipid Res. 2006 Oct;47(10):2101-11. Epub 2006 Aug 10. [PubMed:16902246 ]
  3. Sethi JK, Vidal-Puig AJ: Thematic review series: adipocyte biology. Adipose tissue function and plasticity orchestrate nutritional adaptation. J Lipid Res. 2007 Jun;48(6):1253-62. Epub 2007 Mar 20. [PubMed:17374880 ]
  4. Lingwood D, Simons K: Lipid rafts as a membrane-organizing principle. Science. 2010 Jan 1;327(5961):46-50. doi: 10.1126/science.1174621. [PubMed:20044567 ]
  5. (). Yannai, Shmuel. (2004) Dictionary of food compounds with CD-ROM: Additives, flavors, and ingredients. Boca Raton: Chapman & Hall/CRC.. .
  6. Gunstone, Frank D., John L. Harwood, and Albert J. Dijkstra (2007). The lipid handbook with CD-ROM. CRC Press.