MENTHONE 1,2-GLYCEROL KETAL (CHEM006407)

IdentificationTaxonomyBiological PropertiesPhysical PropertiesToxicity ProfileSpectraConcentrationsLinksReferencesXML
Record Information
Version1.0
Creation Date2016-05-19 02:13:20 UTC
Update Date2016-11-09 01:09:43 UTC
Accession NumberCHEM006407
Identification
Common NameMENTHONE 1,2-GLYCEROL KETAL
ClassSmall Molecule
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.
Contaminant Sources
  • EAFUS Chemicals
  • FooDB Chemicals
  • STOFF IDENT Compounds
Contaminant TypeNot Available
Chemical Structure
Thumb
MOLSDFPDBSMILESInChI
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 Mass228.328 g/mol
Monoisotopic Mass228.173 g/mol
CAS Registry Number63187-91-7
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
SMILESCC(C)C1CCC(C)CC11OCC(CO)O1
InChI IdentifierInChI=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
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 Solubility0.76 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
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleNoChemAxon
Spectra
Spectra
Spectrum TypeDescriptionSplash KeyView
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-0006-9410000000-b382247dd270ed7bd196Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (1 TMS) - 70eV, Positivesplash10-06yc-9530000000-d3d1d3bd28f704c25a53Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, PositiveNot AvailableSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-004i-1290000000-2a33c2ffa8194005ed41Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-004i-9660000000-4dc87a745f4a98040054Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0aor-9200000000-a353fa905f01dc6beef6Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-004i-2090000000-896a1d3ce21e9426591bSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-056s-7590000000-5f419ed783b43a5ae35fSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0f6x-9700000000-f21e3e951e7f6c37611aSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-004i-0090000000-873da861442811ae04b2Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0fb9-0790000000-051ca48c22c625175150Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0ufs-1910000000-4da8dd1b3f946827b52cSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-004i-0090000000-1e3bb0705c3f525a8fe0Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0a4i-9110000000-aa6fefeb9df2fe89aaf2Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0aou-9200000000-8c4be0723acde91d7cd4Spectrum
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 IDHMDB0036139
FooDB IDFDB014990
Phenol Explorer IDNot Available
KNApSAcK IDNot Available
BiGG IDNot Available
BioCyc IDNot Available
METLIN IDNot Available
PDB IDNot Available
Wikipedia LinkNot Available
Chemspider ID142428
ChEBI IDNot Available
PubChem Compound ID162184
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. Yannai, Shmuel. (2004) Dictionary of food compounds with CD-ROM: Additives, flavors, and ingredients. Boca Raton: Chapman & Hall/CRC.
7. The lipid handbook with CD-ROM