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Record Information
Version5.0
StatusExpected but not Quantified
Creation Date2012-09-12 02:56:11 UTC
Update Date2021-10-13 08:33:01 UTC
HMDB IDHMDB0041264
Secondary Accession Numbers
  • HMDB41264
Metabolite Identification
Common Name(±)-Menthyl acetate
Description(±)-Menthyl acetate 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 acetate.
Structure
Data?1563863643
Synonyms
ValueSource
(±)-menthyl acetic acidGenerator
(+-)-Menthol acetateHMDB
(+-)-Menthyl acetateHMDB
(+/-)-menthyl acetateHMDB
(DL)-Menthyl acetateHMDB
DL-p-Menth-3-yl acetateHMDB
Menthol acetateHMDB
Menthyl acetateHMDB
(1S,2R,5S)-5-Methyl-2-(propan-2-yl)cyclohexyl acetic acidHMDB
(+)-Menthyl acetic acidHMDB
Chemical FormulaC12H22O2
Average Molecular Weight198.3019
Monoisotopic Molecular Weight198.161979948
IUPAC Name(1S,2R,5S)-5-methyl-2-(propan-2-yl)cyclohexyl acetate
Traditional Name(1S,2R,5S)-2-isopropyl-5-methylcyclohexyl acetate
CAS Registry Number89-48-5
SMILES
CC(C)[C@H]1CC[C@H](C)C[C@@H]1OC(C)=O
InChI Identifier
InChI=1S/C12H22O2/c1-8(2)11-6-5-9(3)7-12(11)14-10(4)13/h8-9,11-12H,5-7H2,1-4H3/t9-,11+,12-/m0/s1
InChI KeyXHXUANMFYXWVNG-WCQGTBRESA-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
  • 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
Disposition

Biological location

Source

Route of exposure

Physical Properties
StateSolid
Experimental Molecular Properties
PropertyValueReference
Melting Point228 - 229 °CNot Available
Boiling Point228.00 to 229.00 °C. @ 760.00 mm HgThe Good Scents Company Information System
Water Solubility17.13 mg/L @ 25 °C (est)The Good Scents Company Information System
LogP4.182 (est)The Good Scents Company Information System
Experimental Chromatographic PropertiesNot Available
Predicted Molecular Properties
PropertyValueSource
Water Solubility0.019 g/LALOGPS
logP10(3.54) g/LALOGPS
logP10(3.11) g/LChemAxon
logS10(-4) g/LALOGPS
pKa (Strongest Basic)-7ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count1ChemAxon
Hydrogen Donor Count0ChemAxon
Polar Surface Area26.3 ŲChemAxon
Rotatable Bond Count3ChemAxon
Refractivity56.6 m³·mol⁻¹ChemAxon
Polarizability23.74 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]+148.72231661259
DarkChem[M-H]-144.66831661259
DeepCCS[M+H]+151.6630932474

Predicted Kovats Retention Indices

Underivatized

MetaboliteSMILESKovats RI ValueColumn TypeReference
(??)-Menthyl acetateCC(C)[C@H]1CC[C@H](C)C[C@@H]1OC(C)=O1551.4Standard polar33892256
(??)-Menthyl acetateCC(C)[C@H]1CC[C@H](C)C[C@@H]1OC(C)=O1283.9Standard non polar33892256
(??)-Menthyl acetateCC(C)[C@H]1CC[C@H](C)C[C@@H]1OC(C)=O1293.4Semi standard non polar33892256
Spectra

GC-MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Predicted GC-MSPredicted GC-MS Spectrum - (±)-Menthyl acetate GC-MS (Non-derivatized) - 70eV, Positivesplash10-0006-9400000000-c93613f018403ec702c42017-09-01Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - (±)-Menthyl acetate 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 acetate 10V, Positive-QTOFsplash10-0002-1900000000-d72c827a469085629e5d2016-08-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - (±)-Menthyl acetate 20V, Positive-QTOFsplash10-0a4s-4900000000-bf6fb3a5690a1f0320872016-08-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - (±)-Menthyl acetate 40V, Positive-QTOFsplash10-0aor-9200000000-cb81ded288f2424a35562016-08-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - (±)-Menthyl acetate 10V, Negative-QTOFsplash10-052b-0900000000-3501f1a47f8406c0d6f52016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - (±)-Menthyl acetate 20V, Negative-QTOFsplash10-0a4i-2900000000-cb66f3b5eaa6461df1172016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - (±)-Menthyl acetate 40V, Negative-QTOFsplash10-0a4r-4900000000-dcd4936d192617ff77682016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - (±)-Menthyl acetate 10V, Positive-QTOFsplash10-0002-9300000000-262f2d6c6ac2e61856712021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - (±)-Menthyl acetate 20V, Positive-QTOFsplash10-0012-9300000000-24944363b89e43dd9c2b2021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - (±)-Menthyl acetate 40V, Positive-QTOFsplash10-0006-9000000000-4f2ea1271e666be87dda2021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - (±)-Menthyl acetate 10V, Negative-QTOFsplash10-052b-2900000000-6b5ecc1c9ffb6ea437372021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - (±)-Menthyl acetate 20V, Negative-QTOFsplash10-0a4i-9500000000-d0a742a52154626c49062021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - (±)-Menthyl acetate 40V, Negative-QTOFsplash10-0a4l-9000000000-a08bf949a70eb12bd6092021-09-22Wishart 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 IDFDB006041
KNApSAcK IDNot Available
Chemspider ID56127
KEGG Compound IDC09870
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound220674
PDB IDNot Available
ChEBI IDNot Available
Food Biomarker OntologyNot Available
VMH IDNot Available
MarkerDB IDNot Available
Good Scents IDrw1046271
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.