Record Information
Version1.0
Creation date2010-04-08 22:08:48 UTC
Update date2018-05-28 23:25:25 UTC
Primary IDFDB009783
Secondary Accession NumbersNot Available
Chemical Information
FooDB NameL-Menthyl acetoacetate
DescriptionL-Menthyl acetoacetate 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 L-Menthyl acetoacetate.
CAS Number59557-05-0
Structure
Thumb
Synonyms
SynonymSource
L-Menthyl acetoacetic acidGenerator
Menthol acetoacetateHMDB
Menthyl acetoacetateHMDB
(1S,2R,5S)-5-Methyl-2-(propan-2-yl)cyclohexyl 3-oxobutanoic acidGenerator
Predicted Properties
PropertyValueSource
Water Solubility0.039 g/LALOGPS
logP3.18ALOGPS
logP3.33ChemAxon
logS-3.8ALOGPS
pKa (Strongest Acidic)9.64ChemAxon
pKa (Strongest Basic)-7ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count2ChemAxon
Hydrogen Donor Count0ChemAxon
Polar Surface Area43.37 ŲChemAxon
Rotatable Bond Count5ChemAxon
Refractivity66.49 m³·mol⁻¹ChemAxon
Polarizability27.47 ųChemAxon
Number of Rings1ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Chemical FormulaC14H24O3
IUPAC name(1S,2R,5S)-5-methyl-2-(propan-2-yl)cyclohexyl 3-oxobutanoate
InChI IdentifierInChI=1S/C14H24O3/c1-9(2)12-6-5-10(3)7-13(12)17-14(16)8-11(4)15/h9-10,12-13H,5-8H2,1-4H3/t10-,12+,13-/m0/s1
InChI KeyQSVQIPXQOCAWHP-UHTWSYAYSA-N
Isomeric SMILESCC(C)[C@H]1CC[C@H](C)C[C@@H]1OC(=O)CC(C)=O
Average Molecular Weight240.3386
Monoisotopic Molecular Weight240.172544634
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
  • Beta-keto acid
  • Fatty acid ester
  • Keto acid
  • Fatty acyl
  • 1,3-dicarbonyl compound
  • Carboxylic acid ester
  • Ketone
  • Carboxylic acid derivative
  • Monocarboxylic acid or derivatives
  • Organic oxygen compound
  • Hydrocarbon derivative
  • Organic oxide
  • Carbonyl group
  • Organooxygen compound
  • Aliphatic homomonocyclic compound
Molecular FrameworkAliphatic homomonocyclic compounds
External DescriptorsNot Available
Ontology
Disposition

Route of exposure:

Biological location:

Source:

Process

Naturally occurring process:

Role

Industrial application:

Biological role:

Physico-Chemical Properties - Experimental
Physico-Chemical Properties - Experimental
PropertyValueReference
Physical stateNot Available
Physical DescriptionNot Available
Mass CompositionNot Available
Melting PointNot Available
Boiling PointNot Available
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
EI-MS/GC-MS
TypeDescriptionSplash KeyView
Predicted GC-MSL-Menthyl acetoacetate, non-derivatized, Predicted GC-MS Spectrum - 70eV, Positivesplash10-0006-9310000000-c033ed706e3b31dcb9a8Spectrum
Predicted GC-MSL-Menthyl acetoacetate, non-derivatized, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSL-Menthyl acetoacetate, non-derivatized, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
MS/MS
TypeDescriptionSplash KeyView
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0076-3590000000-731d60e9f89574e822972016-06-03View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-052r-9710000000-c6d1e5ac6852973edb0a2016-06-03View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-066r-9200000000-bc771999857dd0324d942016-06-03View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-052r-3690000000-9451a6e145fa7963eba32016-08-03View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0a4i-5920000000-8c56f22d4e9a56081eb82016-08-03View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0a4r-6900000000-4ddad90a98abcf7ceab62016-08-03View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0002-9300000000-843cbdbb4307acf9cc702021-09-22View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-000g-9200000000-a48a077d7b2f75d0c82c2021-09-22View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0006-9000000000-2ea1affc30a4c164c26c2021-09-22View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-052r-4890000000-c2b7721d83f54a29eed22021-09-22View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0pc0-9500000000-e80ade8fc5fb25db2d7f2021-09-22View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0a4i-9400000000-65a4f2f5b20a8b1668182021-09-22View Spectrum
NMRNot Available
ChemSpider ID39229
ChEMBL IDNot Available
KEGG Compound IDNot Available
Pubchem Compound ID43045
Pubchem Substance IDNot Available
ChEBI IDNot Available
Phenol-Explorer IDNot Available
DrugBank IDNot Available
HMDB IDHMDB32369
CRC / DFC (Dictionary of Food Compounds) IDNot Available
EAFUS ID2153
Dr. Duke IDNot Available
BIGG IDNot Available
KNApSAcK IDNot Available
HET IDNot Available
Food Biomarker OntologyNot Available
VMH IDNot Available
Flavornet IDNot Available
GoodScent IDrw1031261
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
minty
  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