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Record Information
Version5.0
StatusExpected but not Quantified
Creation Date2012-09-11 22:27:08 UTC
Update Date2022-03-07 02:55:14 UTC
HMDB IDHMDB0037212
Secondary Accession Numbers
  • HMDB37212
Metabolite Identification
Common NameMenthyl lactate
DescriptionMenthyl lactate 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 significant number of articles have been published on Menthyl lactate.
Structure
Data?1563862994
Synonyms
ValueSource
Menthyl lactic acidGenerator
L-Menthyl lactateMeSH
(-)-P-Menthan-3-yl lactateHMDB
FEMA 3748HMDB
(1R,2S,5R)-5-Methyl-2-(propan-2-yl)cyclohexyl 2-hydroxypropanoic acidGenerator
Chemical FormulaC13H24O3
Average Molecular Weight228.3279
Monoisotopic Molecular Weight228.172544634
IUPAC Name(1R,2S,5R)-5-methyl-2-(propan-2-yl)cyclohexyl 2-hydroxypropanoate
Traditional Name(1R,2S,5R)-2-isopropyl-5-methylcyclohexyl 2-hydroxypropanoate
CAS Registry Number59259-38-0
SMILES
CC(C)[C@@H]1CC[C@@H](C)C[C@H]1OC(=O)C(C)O
InChI Identifier
InChI=1S/C13H24O3/c1-8(2)11-6-5-9(3)7-12(11)16-13(15)10(4)14/h8-12,14H,5-7H2,1-4H3/t9-,10?,11+,12-/m1/s1
InChI KeyUJNOLBSYLSYIBM-SGUBAKSOSA-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
  • Secondary alcohol
  • Carboxylic acid ester
  • Monocarboxylic acid or derivatives
  • Carboxylic acid derivative
  • Organic oxygen compound
  • Organic oxide
  • Hydrocarbon derivative
  • Organooxygen compound
  • Carbonyl group
  • Alcohol
  • Aliphatic homomonocyclic compound
Molecular FrameworkAliphatic homomonocyclic compounds
External DescriptorsNot Available
Ontology
Disposition

Biological location

Physical Properties
StateSolid
Experimental Molecular Properties
PropertyValueReference
Melting Point38 - 40 °CNot Available
Boiling Point142.00 °C. @ 5.00 mm HgThe Good Scents Company Information System
Water Solubility0 slightlyThe Good Scents Company Information System
LogP3.358 (est)The Good Scents Company Information System
Experimental Chromatographic PropertiesNot Available
Predicted Molecular Properties
PropertyValueSource
Water Solubility0.19 g/LALOGPS
logP2.78ALOGPS
logP2.86ChemAxon
logS-3.1ALOGPS
pKa (Strongest Acidic)13ChemAxon
pKa (Strongest Basic)-3.7ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count2ChemAxon
Hydrogen Donor Count1ChemAxon
Polar Surface Area46.53 ŲChemAxon
Rotatable Bond Count4ChemAxon
Refractivity62.79 m³·mol⁻¹ChemAxon
Polarizability26.34 ųChemAxon
Number of Rings1ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Predicted Chromatographic Properties

Predicted Collision Cross Sections

PredictorAdduct TypeCCS Value (Å2)Reference
DarkChem[M+H]+152.8731661259
DarkChem[M-H]-151.64631661259
DeepCCS[M+H]+159.7330932474
DeepCCS[M-H]-157.37230932474
DeepCCS[M-2H]-190.73930932474
DeepCCS[M+Na]+165.96630932474

Predicted Kovats Retention Indices

Underivatized

MetaboliteSMILESKovats RI ValueColumn TypeReference
Menthyl lactateCC(C)[C@@H]1CC[C@@H](C)C[C@H]1OC(=O)C(C)O2002.8Standard polar33892256
Menthyl lactateCC(C)[C@@H]1CC[C@@H](C)C[C@H]1OC(=O)C(C)O1468.3Standard non polar33892256
Menthyl lactateCC(C)[C@@H]1CC[C@@H](C)C[C@H]1OC(=O)C(C)O1493.9Semi standard non polar33892256

Derivatized

Derivative Name / StructureSMILESKovats RI ValueColumn TypeReference
Menthyl lactate,1TMS,isomer #1CC(O[Si](C)(C)C)C(=O)O[C@@H]1C[C@H](C)CC[C@H]1C(C)C1610.7Semi standard non polar33892256
Menthyl lactate,1TBDMS,isomer #1CC(O[Si](C)(C)C(C)(C)C)C(=O)O[C@@H]1C[C@H](C)CC[C@H]1C(C)C1826.6Semi standard non polar33892256
Spectra

GC-MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Predicted GC-MSPredicted GC-MS Spectrum - Menthyl lactate GC-MS (Non-derivatized) - 70eV, Positivesplash10-0005-9200000000-c48e8eb9e325bf5c81fe2017-09-01Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Menthyl lactate GC-MS (1 TMS) - 70eV, Positivesplash10-00ku-9810000000-3204a8c0047d47f59c312017-10-06Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Menthyl lactate 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 lactate 10V, Positive-QTOFsplash10-056r-3790000000-656c618ebe79ee17c9952017-09-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Menthyl lactate 20V, Positive-QTOFsplash10-0a4r-9710000000-6125d6ceccc2f46b4ac42017-09-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Menthyl lactate 40V, Positive-QTOFsplash10-0a4i-9400000000-63fcdcc1bb57fb80142d2017-09-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Menthyl lactate 10V, Negative-QTOFsplash10-0a6r-1980000000-4e50a980d739641e3afc2017-09-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Menthyl lactate 20V, Negative-QTOFsplash10-0a4i-1900000000-5d2874c2be1ece163ff82017-09-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Menthyl lactate 40V, Negative-QTOFsplash10-052r-1900000000-f3921cfdce07deda74642017-09-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Menthyl lactate 10V, Negative-QTOFsplash10-0a6r-2960000000-f585e586acf3e1ddaaf82021-09-23Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Menthyl lactate 20V, Negative-QTOFsplash10-00di-9400000000-1a89bb184c19723d72e72021-09-23Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Menthyl lactate 40V, Negative-QTOFsplash10-0007-9100000000-bedbf62a7ccbf2dcb64a2021-09-23Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Menthyl lactate 10V, Positive-QTOFsplash10-0002-9300000000-cf2188d4102f886cdb3e2021-09-24Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Menthyl lactate 20V, Positive-QTOFsplash10-0002-9400000000-23c4d31979e1b9888ad62021-09-24Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Menthyl lactate 40V, Positive-QTOFsplash10-0002-9000000000-6cf7fb94dc69ec979c572021-09-24Wishart 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 IDFDB016219
KNApSAcK IDNot Available
Chemspider ID55982
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound62151
PDB IDNot Available
ChEBI IDNot Available
Food Biomarker OntologyNot Available
VMH IDNot Available
MarkerDB IDNot Available
Good Scents IDrw1038041
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.