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Record Information
Version5.0
StatusExpected but not Quantified
Creation Date2012-09-11 17:50:27 UTC
Update Date2022-03-07 02:53:23 UTC
HMDB IDHMDB0032553
Secondary Accession Numbers
  • HMDB32553
Metabolite Identification
Common NameVanillin 3-(L-menthoxy)propane-1,2-diol acetal
DescriptionVanillin 3-(L-menthoxy)propane-1,2-diol acetal belongs to the class of organic compounds known as aromatic monoterpenoids. These are monoterpenoids containing at least one aromatic ring. Based on a literature review a significant number of articles have been published on Vanillin 3-(L-menthoxy)propane-1,2-diol acetal.
Structure
Data?1563862275
Synonyms
ValueSource
2-Methoxy-4-[4-[[[5-methyl-2-(1-methylethyl)cyclohexyl]oxy]methyl]-1,3-dioxolan-2-yl]-phenolHMDB
Chemical FormulaC21H32O5
Average Molecular Weight364.4758
Monoisotopic Molecular Weight364.224974134
IUPAC Name2-methoxy-4-[4-({[5-methyl-2-(propan-2-yl)cyclohexyl]oxy}methyl)-1,3-dioxolan-2-yl]phenol
Traditional Name4-(4-{[(2-isopropyl-5-methylcyclohexyl)oxy]methyl}-1,3-dioxolan-2-yl)-2-methoxyphenol
CAS Registry Number180964-47-0
SMILES
COC1=C(O)C=CC(=C1)C1OCC(COC2CC(C)CCC2C(C)C)O1
InChI Identifier
InChI=1S/C21H32O5/c1-13(2)17-7-5-14(3)9-19(17)24-11-16-12-25-21(26-16)15-6-8-18(22)20(10-15)23-4/h6,8,10,13-14,16-17,19,21-22H,5,7,9,11-12H2,1-4H3
InChI KeyZOGKSXQLOOQXFG-UHFFFAOYSA-N
Chemical Taxonomy
Description Belongs to the class of organic compounds known as aromatic monoterpenoids. These are monoterpenoids containing at least one aromatic ring.
KingdomOrganic compounds
Super ClassLipids and lipid-like molecules
ClassPrenol lipids
Sub ClassMonoterpenoids
Direct ParentAromatic monoterpenoids
Alternative Parents
Substituents
  • Aromatic monoterpenoid
  • P-menthane monoterpenoid
  • Monocyclic monoterpenoid
  • Methoxyphenol
  • Phenoxy compound
  • Anisole
  • Methoxybenzene
  • Phenol ether
  • 1-hydroxy-2-unsubstituted benzenoid
  • Alkyl aryl ether
  • Phenol
  • Benzenoid
  • Monocyclic benzene moiety
  • Meta-dioxolane
  • Acetal
  • Oxacycle
  • Organoheterocyclic compound
  • Dialkyl ether
  • Ether
  • Hydrocarbon derivative
  • Organooxygen compound
  • Organic oxygen compound
  • Aromatic heteromonocyclic compound
Molecular FrameworkAromatic heteromonocyclic compounds
External DescriptorsNot Available
Ontology
Physiological effect
Disposition
Process
Role
Physical Properties
StateNot Available
Experimental Molecular Properties
PropertyValueReference
Melting Point78.00 to 80.00 °C. @ 760.00 mm HgThe Good Scents Company Information System
Boiling PointNot AvailableNot Available
Water Solubility1 mg/L @ 25 °C (est)The Good Scents Company Information System
LogPNot AvailableNot Available
Experimental Chromatographic PropertiesNot Available
Predicted Molecular Properties
PropertyValueSource
Water Solubility0.0094 g/LALOGPS
logP4.18ALOGPS
logP4.69ChemAxon
logS-4.6ALOGPS
pKa (Strongest Acidic)9.88ChemAxon
pKa (Strongest Basic)-3.8ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count5ChemAxon
Hydrogen Donor Count1ChemAxon
Polar Surface Area57.15 ŲChemAxon
Rotatable Bond Count6ChemAxon
Refractivity99.78 m³·mol⁻¹ChemAxon
Polarizability41.87 ųChemAxon
Number of Rings3ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleYesChemAxon
Predicted Chromatographic Properties

Predicted Collision Cross Sections

PredictorAdduct TypeCCS Value (Å2)Reference
DarkChem[M+H]+186.46431661259
DarkChem[M-H]-185.89631661259
DeepCCS[M+H]+192.0530932474
DeepCCS[M-H]-189.69230932474
DeepCCS[M-2H]-223.86230932474
DeepCCS[M+Na]+199.08930932474
AllCCS[M+H]+191.532859911
AllCCS[M+H-H2O]+188.832859911
AllCCS[M+NH4]+194.032859911
AllCCS[M+Na]+194.732859911
AllCCS[M-H]-191.332859911
AllCCS[M+Na-2H]-191.932859911
AllCCS[M+HCOO]-192.632859911

Predicted Kovats Retention Indices

Underivatized

MetaboliteSMILESKovats RI ValueColumn TypeReference
Vanillin 3-(L-menthoxy)propane-1,2-diol acetalCOC1=C(O)C=CC(=C1)C1OCC(COC2CC(C)CCC2C(C)C)O13389.7Standard polar33892256
Vanillin 3-(L-menthoxy)propane-1,2-diol acetalCOC1=C(O)C=CC(=C1)C1OCC(COC2CC(C)CCC2C(C)C)O12570.2Standard non polar33892256
Vanillin 3-(L-menthoxy)propane-1,2-diol acetalCOC1=C(O)C=CC(=C1)C1OCC(COC2CC(C)CCC2C(C)C)O12773.8Semi standard non polar33892256

Derivatized

Derivative Name / StructureSMILESKovats RI ValueColumn TypeReference
Vanillin 3-(L-menthoxy)propane-1,2-diol acetal,1TMS,isomer #1COC1=CC(C2OCC(COC3CC(C)CCC3C(C)C)O2)=CC=C1O[Si](C)(C)C2704.6Semi standard non polar33892256
Vanillin 3-(L-menthoxy)propane-1,2-diol acetal,1TBDMS,isomer #1COC1=CC(C2OCC(COC3CC(C)CCC3C(C)C)O2)=CC=C1O[Si](C)(C)C(C)(C)C2930.1Semi standard non polar33892256
Spectra

GC-MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Predicted GC-MSPredicted GC-MS Spectrum - Vanillin 3-(L-menthoxy)propane-1,2-diol acetal GC-MS (Non-derivatized) - 70eV, Positivesplash10-00kg-8913000000-036a5052e289a918456d2017-09-01Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Vanillin 3-(L-menthoxy)propane-1,2-diol acetal GC-MS (1 TMS) - 70eV, Positivesplash10-00dl-9521400000-b17e987ce42e5e7950d42017-10-06Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Vanillin 3-(L-menthoxy)propane-1,2-diol acetal 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 - Vanillin 3-(L-menthoxy)propane-1,2-diol acetal 10V, Positive-QTOFsplash10-014i-0719000000-842f887cdd1574fab1122017-09-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Vanillin 3-(L-menthoxy)propane-1,2-diol acetal 20V, Positive-QTOFsplash10-05tr-3916000000-58438b5b3974052088542017-09-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Vanillin 3-(L-menthoxy)propane-1,2-diol acetal 40V, Positive-QTOFsplash10-0609-7900000000-6dd1fb5360412eb892402017-09-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Vanillin 3-(L-menthoxy)propane-1,2-diol acetal 10V, Negative-QTOFsplash10-03di-0409000000-c1be73d55ca2c69853382017-09-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Vanillin 3-(L-menthoxy)propane-1,2-diol acetal 20V, Negative-QTOFsplash10-0a4i-0901000000-2ea0541d6bf5ea16e5182017-09-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Vanillin 3-(L-menthoxy)propane-1,2-diol acetal 40V, Negative-QTOFsplash10-0a4r-0900000000-0b5d71f80d53fd63b6ce2017-09-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Vanillin 3-(L-menthoxy)propane-1,2-diol acetal 10V, Positive-QTOFsplash10-014i-3119000000-8f02bfe2133ec6861bb32021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Vanillin 3-(L-menthoxy)propane-1,2-diol acetal 20V, Positive-QTOFsplash10-0002-9432000000-605f22536ae54d1c573b2021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Vanillin 3-(L-menthoxy)propane-1,2-diol acetal 40V, Positive-QTOFsplash10-000i-4910000000-51535508399b24122f5f2021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Vanillin 3-(L-menthoxy)propane-1,2-diol acetal 10V, Negative-QTOFsplash10-03di-0309000000-8e747c345ec322b6d9b02021-09-23Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Vanillin 3-(L-menthoxy)propane-1,2-diol acetal 20V, Negative-QTOFsplash10-01qi-0915000000-408fdb6d9b111674b1ee2021-09-23Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Vanillin 3-(L-menthoxy)propane-1,2-diol acetal 40V, Negative-QTOFsplash10-03du-1927000000-cd649462075db1978f482021-09-23Wishart 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 IDFDB010449
KNApSAcK IDNot Available
Chemspider ID9806724
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound11631979
PDB IDNot Available
ChEBI IDNot Available
Food Biomarker OntologyNot Available
VMH IDNot Available
MarkerDB IDNot Available
Good Scents IDrw1422351
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. (). EAFUS: Everything Added to Food in the United States.. .
  6. Gunstone, Frank D., John L. Harwood, and Albert J. Dijkstra (2007). The lipid handbook with CD-ROM. CRC Press.