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Record Information
Version5.0
StatusExpected but not Quantified
Creation Date2012-09-11 20:47:14 UTC
Update Date2021-10-13 06:51:18 UTC
HMDB IDHMDB0035766
Secondary Accession Numbers
  • HMDB35766
Metabolite Identification
Common NameAscaridole
DescriptionAscaridole is found in cardamom. Said to be the major constituent of oil of Peumus boldus (boldo).Ascaridole is a natural organic compound classified as a bicyclic monoterpene that has an unusual bridging peroxide functional group. It is the primary constituent of the oil of Mexican Tea (Dysphania ambrosioides, formerly Chenopodium ambrosioides). It is a colorless liquid that is soluble in most organic solvents. Like other low molecular weight organic peroxides, it is unstable and prone to explosion when heated or treated with organic acids
Structure
Data?1563862768
Synonyms
ValueSource
1,4-Epidioxy-p-menth-2-eneChEBI
1,4-Peroxido-p-menthene-2ChEBI
1,4-Peroxy-p-menth-2-eneChEBI
1-Isopropyl-4-methyl-2,3-dioxabicyclo[2.2.2]oct-5-eneChEBI
1-Methyl-4-(1-methylethyl)-2,3-dioxabicyclo[2.2.2]oct-5-eneChEBI
1, 4-Epidioxy-P-menth-2-eneHMDB
1, 4-Peroxy-P-menth-2-eneHMDB
1,4-Epidioxy-2-P-mentheneHMDB
1-Isopropyl-4-methyl-2,3-dioxabicyclo(2.2.2)oct-5-eneHMDB
1-Isopropyl-4-methyl-7-oxabicyclo[2.2.1]hept-2-eneHMDB
1-Methyl-4-(1-methylethyl)-2,3-dioxabicyclo(2.2.2)oct-5-eneHMDB
1-Methyl-4-(1-methylethyl)-2,3-dioxabicyclo[2.2.2]oct-5-ene, 9ciHMDB
4-Methyl-1-(propan-2-yl)-2,3-dioxabicyclo[2.2.2]oct-5-eneHMDB
AscapurinHMDB
AscaricumHMDB
AscaridiolHMDB
AscaridolHMDB
Ascaridole (organic peroxide)HMDB
Ascaridole epoxideHMDB
AscarisinHMDB
AskaridolHMDB
cis-AscaridoleHMDB
Kebal IIHMDB
UncinacinaHMDB
Chemical FormulaC10H16O2
Average Molecular Weight168.2328
Monoisotopic Molecular Weight168.115029756
IUPAC Name1-methyl-4-(propan-2-yl)-2,3-dioxabicyclo[2.2.2]oct-5-ene
Traditional Nameascaridole
CAS Registry Number512-85-6
SMILES
CC(C)C12CCC(C)(OO1)C=C2
InChI Identifier
InChI=1S/C10H16O2/c1-8(2)10-6-4-9(3,5-7-10)11-12-10/h4,6,8H,5,7H2,1-3H3
InChI KeyMGYMHQJELJYRQS-UHFFFAOYSA-N
Chemical Taxonomy
Description Belongs to the class of organic compounds known as 1,2-dioxanes. These are organic compounds containing 1,2-dioxane, an aliphatic six-member ring with two oxygen atoms in ring positions 1 and 2.
KingdomOrganic compounds
Super ClassOrganoheterocyclic compounds
ClassDioxanes
Sub Class1,2-dioxanes
Direct Parent1,2-dioxanes
Alternative Parents
Substituents
  • Ortho-dioxane
  • Dialkyl peroxide
  • Oxacycle
  • Organic oxygen compound
  • Hydrocarbon derivative
  • Organooxygen compound
  • Aliphatic heteropolycyclic compound
Molecular FrameworkAliphatic heteropolycyclic compounds
External Descriptors
Ontology
Disposition

Biological location

Source

Route of exposure

Physical Properties
StateLiquid
Experimental Molecular Properties
PropertyValueReference
Melting Point3.3 °CNot Available
Boiling Point112.00 to 115.00 °C. @ 20.00 mm HgThe Good Scents Company Information System
Water Solubility55.5 mg/L @ 25 °C (est)The Good Scents Company Information System
LogP2.244 (est)The Good Scents Company Information System
Experimental Spectral PropertiesNot Available
Predicted Molecular Properties
PropertyValueSource
Water Solubility0.53 g/LALOGPS
logP10(2.64) g/LALOGPS
logP10(2.64) g/LChemAxon
logS10(-2.5) g/LALOGPS
pKa (Strongest Basic)-4.9ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count2ChemAxon
Hydrogen Donor Count0ChemAxon
Polar Surface Area18.46 ŲChemAxon
Rotatable Bond Count1ChemAxon
Refractivity47.6 m³·mol⁻¹ChemAxon
Polarizability18.93 ųChemAxon
Number of Rings2ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleNoChemAxon
Predicted Spectral Properties

Predicted Collision Cross Sections

PredictorAdduct TypeCCS Value (Å2)Reference
DarkChem[M+H]+137.08531661259
DarkChem[M-H]-131.1431661259

Predicted Kovats Retention Indices

Not Available
Spectra

GC-MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Predicted GC-MSPredicted GC-MS Spectrum - Ascaridole GC-MS (Non-derivatized) - 70eV, Positivesplash10-004i-2900000000-4e6342ba9b29d1dd42ad2017-09-01Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Ascaridole GC-MS (Non-derivatized) - 70eV, PositiveNot Available2021-10-12Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Ascaridole 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 - Ascaridole 10V, Positive-QTOFsplash10-014i-0900000000-83d7b2bd24b624b5ea982016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Ascaridole 20V, Positive-QTOFsplash10-014i-0900000000-1d0d1c7edaaa69d194a12016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Ascaridole 40V, Positive-QTOFsplash10-0udi-0900000000-2c78632dd190511927b92016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Ascaridole 10V, Negative-QTOFsplash10-014i-0900000000-177dc272267c0f5437012016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Ascaridole 20V, Negative-QTOFsplash10-014i-0900000000-3317598e1aa469191e582016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Ascaridole 40V, Negative-QTOFsplash10-0adi-0900000000-fb70c59640ba1c0d01a62016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Ascaridole 10V, Negative-QTOFsplash10-014i-0900000000-cb7592114e600c180aec2021-09-25Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Ascaridole 20V, Negative-QTOFsplash10-014i-0900000000-cb7592114e600c180aec2021-09-25Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Ascaridole 40V, Negative-QTOFsplash10-014i-0900000000-3a7e13f32c837bc356ac2021-09-25Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Ascaridole 10V, Positive-QTOFsplash10-014i-0900000000-f9b2951dd69b378c60312021-09-25Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Ascaridole 20V, Positive-QTOFsplash10-016r-0900000000-460c95031436dfd1e1b72021-09-25Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Ascaridole 40V, Positive-QTOFsplash10-004i-0900000000-6a28e536e83eb1686dba2021-09-25Wishart 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 IDFDB014503
KNApSAcK IDC00003027
Chemspider ID10105
KEGG Compound IDC09836
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkAscaridole
METLIN IDNot Available
PubChem Compound10545
PDB IDNot Available
ChEBI ID2866
Food Biomarker OntologyNot Available
VMH IDNot Available
MarkerDB IDNot Available
Good Scents IDrw1011381
References
Synthesis ReferenceNot Available
Material Safety Data Sheet (MSDS)Not Available
General References
  1. (). Yannai, Shmuel. (2004) Dictionary of food compounds with CD-ROM: Additives, flavors, and ingredients. Boca Raton: Chapman & Hall/CRC.. .