L-MENTHYL ACETOACETATE (CHEM006414)

IdentificationTaxonomyBiological PropertiesPhysical PropertiesToxicity ProfileSpectraConcentrationsLinksReferencesXML
Record Information
Version1.0
Creation Date2016-05-19 02:13:25 UTC
Update Date2016-11-09 01:09:43 UTC
Accession NumberCHEM006414
Identification
Common NameL-MENTHYL ACETOACETATE
ClassSmall Molecule
DescriptionL-Menthyl acetoacetate is used as a food additive [EAFUS] ("EAFUS: Everything Added to Food in the United States. [http://www.eafus.com/]")
Contaminant Sources
  • EAFUS Chemicals
  • FooDB Chemicals
Contaminant TypeNot Available
Chemical Structure
Thumb
MOLSDFPDBSMILESInChI
Synonyms
ValueSource
L-Menthyl acetoacetic acidGenerator
Menthol acetoacetateHMDB
Menthyl acetoacetateHMDB
(1S,2R,5S)-5-Methyl-2-(propan-2-yl)cyclohexyl 3-oxobutanoic acidGenerator
Chemical FormulaC14H24O3
Average Molecular Mass240.339 g/mol
Monoisotopic Mass240.173 g/mol
CAS Registry Number59557-05-0
IUPAC Name(1S,2R,5S)-5-methyl-2-(propan-2-yl)cyclohexyl 3-oxobutanoate
Traditional Name(1S,2R,5S)-2-isopropyl-5-methylcyclohexyl 3-oxobutanoate
SMILESCC(C)[C@H]1CC[C@H](C)C[C@@H]1OC(=O)CC(C)=O
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
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
  • 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
Biological Properties
StatusDetected and Not Quantified
OriginNot Available
Cellular LocationsNot Available
Biofluid LocationsNot Available
Tissue LocationsNot Available
PathwaysNot Available
ApplicationsNot Available
Biological RolesNot Available
Chemical RolesNot Available
Physical Properties
StateNot Available
AppearanceNot Available
Experimental Properties
PropertyValue
Melting PointNot Available
Boiling PointNot Available
SolubilityNot Available
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
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Spectra
Spectra
Spectrum TypeDescriptionSplash KeyView
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-0006-9310000000-c033ed706e3b31dcb9a8Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, PositiveNot AvailableSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0076-3590000000-731d60e9f89574e82297Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-052r-9710000000-c6d1e5ac6852973edb0aSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-066r-9200000000-bc771999857dd0324d94Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-052r-3690000000-9451a6e145fa7963eba3Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0a4i-5920000000-8c56f22d4e9a56081eb8Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0a4r-6900000000-4ddad90a98abcf7ceab6Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0002-9300000000-843cbdbb4307acf9cc70Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-000g-9200000000-a48a077d7b2f75d0c82cSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0006-9000000000-2ea1affc30a4c164c26cSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-052r-4890000000-c2b7721d83f54a29eed2Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0pc0-9500000000-e80ade8fc5fb25db2d7fSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0a4i-9400000000-65a4f2f5b20a8b166818Spectrum
Toxicity Profile
Route of ExposureNot Available
Mechanism of ToxicityNot Available
MetabolismNot Available
Toxicity ValuesNot Available
Lethal DoseNot Available
Carcinogenicity (IARC Classification)Not Available
Uses/SourcesNot Available
Minimum Risk LevelNot Available
Health EffectsNot Available
SymptomsNot Available
TreatmentNot Available
Concentrations
Not Available
DrugBank IDNot Available
HMDB IDHMDB0032369
FooDB IDFDB009783
Phenol Explorer IDNot Available
KNApSAcK IDNot Available
BiGG IDNot Available
BioCyc IDNot Available
METLIN IDNot Available
PDB IDNot Available
Wikipedia LinkNot Available
Chemspider ID39229
ChEBI ID168575
PubChem Compound ID43045
Kegg Compound IDNot Available
YMDB IDNot Available
ECMDB IDNot Available
References
Synthesis ReferenceNot Available
MSDSNot Available
General References
1. Simons K, Toomre D: Lipid rafts and signal transduction. Nat Rev Mol Cell Biol. 2000 Oct;1(1):31-9.
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.
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.
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.
5. EAFUS: Everything Added to Food in the United States.
6. The lipid handbook with CD-ROM