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Record Information
Version5.0
StatusExpected but not Quantified
Creation Date2012-09-11 21:12:14 UTC
Update Date2022-03-07 02:54:48 UTC
HMDB IDHMDB0036139
Secondary Accession Numbers
  • HMDB0032367
  • HMDB32367
  • HMDB36139
Metabolite Identification
Common NameMenthone 1,2-glyceryl ketal
DescriptionMenthone 1,2-glyceryl ketal, also known as menthone glycerin acetal or menthyl glycerin acetal, is a member of the class of compounds known as menthane monoterpenoids. Menthane monoterpenoids 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. Menthone 1,2-glyceryl ketal is practically insoluble (in water) and a very weakly acidic compound (based on its pKa). Menthone 1,2-glyceryl ketal is used as a food additive (EAFUS: Everything Added to Food in the United States). Menthone 1,2-glyceryl ketal is a flavour enhancer for chewing gum and other low moisture foods.
Structure
Data?1563862826
Synonyms
ValueSource
2-Hydroxymethyl-6-isopropyl-9-methyl-1,4-dioxaspiro[4.5]decaneHMDB
6-Isopropyl-9-methyl-1,4-dioxaspiro(4.5)decane-2-methanolHMDB
9-Methyl-6-(1-methylethyl)-1,4-dioxaspiro[4.5]decane-2-methanol, 9ciHMDB
FEMA 3807HMDB
FEMA 3808HMDB
FrescolatHMDB
Menthone 1,2-glycerol ketalHMDB
Frescolat MGAHMDB
Menthone glycerin acetalHMDB
Menthyl glycerin acetalHMDB
Menthone glyceryl acetalHMDB
Menthone glyceryl ketalHMDB
MGAHMDB
L-Menthone 1,2-glycerol ketalHMDB
Chemical FormulaC13H24O3
Average Molecular Weight228.3279
Monoisotopic Molecular Weight228.172544634
IUPAC Name[9-methyl-6-(propan-2-yl)-1,4-dioxaspiro[4.5]decan-2-yl]methanol
Traditional Name{6-isopropyl-9-methyl-1,4-dioxaspiro[4.5]decan-2-yl}methanol
CAS Registry Number63187-91-7
SMILES
CC(C)C1CCC(C)CC11OCC(CO)O1
InChI Identifier
InChI=1S/C13H24O3/c1-9(2)12-5-4-10(3)6-13(12)15-8-11(7-14)16-13/h9-12,14H,4-8H2,1-3H3
InChI KeyZBJCYZPANVLBRK-UHFFFAOYSA-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
  • Ketal
  • Meta-dioxolane
  • Oxacycle
  • Organoheterocyclic compound
  • Acetal
  • Organic oxygen compound
  • Hydrocarbon derivative
  • Primary alcohol
  • Organooxygen compound
  • Alcohol
  • Aliphatic heteropolycyclic compound
Molecular FrameworkAliphatic heteropolycyclic compounds
External DescriptorsNot Available
Ontology
Disposition

Biological location

Physical Properties
StateNot Available
Experimental Molecular Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling Point322.00 to 323.00 °C. @ 760.00 mm HgThe Good Scents Company Information System
Water Solubility27.28 mg/L @ 25 °C (est)The Good Scents Company Information System
LogP3.036 (est)The Good Scents Company Information System
Experimental Chromatographic PropertiesNot Available
Predicted Molecular Properties
PropertyValueSource
Water Solubility0.76 g/LALOGPS
logP2ALOGPS
logP2.62ChemAxon
logS-2.5ALOGPS
pKa (Strongest Acidic)14.6ChemAxon
pKa (Strongest Basic)-3ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count3ChemAxon
Hydrogen Donor Count1ChemAxon
Polar Surface Area38.69 ŲChemAxon
Rotatable Bond Count2ChemAxon
Refractivity62.57 m³·mol⁻¹ChemAxon
Polarizability26.59 ųChemAxon
Number of Rings2ChemAxon
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]+151.75131661259
DarkChem[M-H]-150.96631661259
DeepCCS[M-2H]-193.36330932474
DeepCCS[M+Na]+168.74430932474

Predicted Kovats Retention Indices

Underivatized

MetaboliteSMILESKovats RI ValueColumn TypeReference
Menthone 1,2-glyceryl ketalCC(C)C1CCC(C)CC11OCC(CO)O12230.6Standard polar33892256
Menthone 1,2-glyceryl ketalCC(C)C1CCC(C)CC11OCC(CO)O11589.3Standard non polar33892256
Menthone 1,2-glyceryl ketalCC(C)C1CCC(C)CC11OCC(CO)O11669.7Semi standard non polar33892256

Derivatized

Derivative Name / StructureSMILESKovats RI ValueColumn TypeReference
Menthone 1,2-glyceryl ketal,1TMS,isomer #1CC1CCC(C(C)C)C2(C1)OCC(CO[Si](C)(C)C)O21692.1Semi standard non polar33892256
Menthone 1,2-glyceryl ketal,1TBDMS,isomer #1CC1CCC(C(C)C)C2(C1)OCC(CO[Si](C)(C)C(C)(C)C)O21936.1Semi standard non polar33892256
Spectra

GC-MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Predicted GC-MSPredicted GC-MS Spectrum - Menthone 1,2-glyceryl ketal GC-MS (Non-derivatized) - 70eV, Positivesplash10-0006-9410000000-b382247dd270ed7bd1962017-09-01Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Menthone 1,2-glyceryl ketal GC-MS (1 TMS) - 70eV, Positivesplash10-06yc-9530000000-d3d1d3bd28f704c25a532017-10-06Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Menthone 1,2-glyceryl ketal 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 - Menthone 1,2-glyceryl ketal 10V, Positive-QTOFsplash10-004i-1290000000-2a33c2ffa8194005ed412016-08-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Menthone 1,2-glyceryl ketal 20V, Positive-QTOFsplash10-004i-9660000000-4dc87a745f4a980400542016-08-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Menthone 1,2-glyceryl ketal 40V, Positive-QTOFsplash10-0aor-9200000000-a353fa905f01dc6beef62016-08-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Menthone 1,2-glyceryl ketal 10V, Negative-QTOFsplash10-004i-2090000000-896a1d3ce21e9426591b2016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Menthone 1,2-glyceryl ketal 20V, Negative-QTOFsplash10-056s-7590000000-5f419ed783b43a5ae35f2016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Menthone 1,2-glyceryl ketal 40V, Negative-QTOFsplash10-0f6x-9700000000-f21e3e951e7f6c37611a2016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Menthone 1,2-glyceryl ketal 10V, Negative-QTOFsplash10-004i-0090000000-873da861442811ae04b22021-09-23Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Menthone 1,2-glyceryl ketal 20V, Negative-QTOFsplash10-0fb9-0790000000-051ca48c22c6251751502021-09-23Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Menthone 1,2-glyceryl ketal 40V, Negative-QTOFsplash10-0ufs-1910000000-4da8dd1b3f946827b52c2021-09-23Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Menthone 1,2-glyceryl ketal 10V, Positive-QTOFsplash10-004i-0090000000-1e3bb0705c3f525a8fe02021-09-25Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Menthone 1,2-glyceryl ketal 20V, Positive-QTOFsplash10-0a4i-9110000000-aa6fefeb9df2fe89aaf22021-09-25Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Menthone 1,2-glyceryl ketal 40V, Positive-QTOFsplash10-0aou-9200000000-8c4be0723acde91d7cd42021-09-25Wishart LabView Spectrum
Biological Properties
Cellular Locations
  • Cytoplasm
  • 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 IDFDB014990
KNApSAcK IDNot Available
Chemspider ID142428
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound162184
PDB IDNot Available
ChEBI IDNot Available
Food Biomarker OntologyNot Available
VMH IDNot Available
MarkerDB IDNot Available
Good Scents IDrw1450851
References
Synthesis ReferenceNot Available
Material Safety Data Sheet (MSDS)Download (PDF)
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. (). EAFUS: Everything Added to Food in the United States.. .
  6. (). Yannai, Shmuel. (2004) Dictionary of food compounds with CD-ROM: Additives, flavors, and ingredients. Boca Raton: Chapman & Hall/CRC.. .
  7. Gunstone, Frank D., John L. Harwood, and Albert J. Dijkstra (2007). The lipid handbook with CD-ROM. CRC Press.