Record Information
Version1.0
Creation date2010-04-08 22:11:18 UTC
Update date2018-05-29 01:12:35 UTC
Primary IDFDB014503
Secondary Accession NumbersNot Available
Chemical Information
FooDB NameAscaridole
DescriptionSaid 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. Ascaridole is found in cardamom, fruits, and lambsquarters.
CAS Number512-85-6
Structure
Thumb
Synonyms
SynonymSource
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
1-methyl-4-(1-methylethyl)-2,3-dioxabicyclo[2.2.2]oct-5-enebiospider
1-Methyl-4-(1-methylethyl)-2,3-dioxabicyclo[2.2.2]oct-5-ene, 9CIdb_source
2,3-Dioxabicyclo(2.2.2)oct-5-ene, 1-isopropyl-4-methyl-biospider
2,3-Dioxabicyclo[2.2.2]oct-5-ene, 1-isopropyl-4-methyl-biospider
4-methyl-1-(propan-2-yl)-2,3-dioxabicyclo[2.2.2]oct-5-enebiospider
Ascaridole (organic peroxide) [forbidden]biospider
Cis-ascaridolebiospider
p-Menth-2-ene, 1,4-epidioxy-biospider
Predicted Properties
PropertyValueSource
Water Solubility0.53 g/LALOGPS
logP2.64ALOGPS
logP2.64ChemAxon
logS-2.5ALOGPS
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
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Chemical FormulaC10H16O2
IUPAC name1-methyl-4-(propan-2-yl)-2,3-dioxabicyclo[2.2.2]oct-5-ene
InChI IdentifierInChI=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
Isomeric SMILESCC(C)C12CCC(C)(OO1)C=C2
Average Molecular Weight168.2328
Monoisotopic Molecular Weight168.115029756
Classification
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
Physico-Chemical Properties - Experimental
Physico-Chemical Properties - Experimental
PropertyValueReference
Physical stateLiquid
Physical DescriptionNot Available
Mass CompositionC 71.39%; H 9.59%; O 19.02%DFC
Melting PointMp 3.3°DFC
Boiling PointBp0.2 39-40°DFC
Experimental Water SolubilityNot Available
Experimental logPNot Available
Experimental pKaNot Available
Isoelectric pointNot Available
ChargeNot Available
Optical RotationNot Available
Spectroscopic UV DataNot Available
Densityd204 1.01DFC
Refractive IndexNot Available
Spectra
Spectra
Spectrum TypeDescriptionSplash Key
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-004i-2900000000-4e6342ba9b29d1dd42adView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-014i-0900000000-83d7b2bd24b624b5ea98View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-014i-0900000000-1d0d1c7edaaa69d194a1View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0udi-0900000000-2c78632dd190511927b9View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-014i-0900000000-177dc272267c0f543701View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-014i-0900000000-3317598e1aa469191e58View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0adi-0900000000-fb70c59640ba1c0d01a6View in MoNA
ChemSpider ID10105
ChEMBL IDCHEMBL467614
KEGG Compound IDC09836
Pubchem Compound ID10545
Pubchem Substance IDNot Available
ChEBI ID2866
Phenol-Explorer IDNot Available
DrugBank IDNot Available
HMDB IDHMDB35766
CRC / DFC (Dictionary of Food Compounds) IDJRL78-N:JRL78-N
EAFUS IDNot Available
Dr. Duke IDASCARIDOLE
BIGG IDNot Available
KNApSAcK IDC00003027
HET IDNot Available
Flavornet IDNot Available
GoodScent IDNot Available
SuperScent IDNot Available
Wikipedia IDAscaridole
Phenol-Explorer Metabolite IDNot Available
Duplicate IDSNot Available
Old DFC IDSNot Available
Associated Foods
FoodContent Range AverageReference
FoodReference
Biological Effects and Interactions
Health Effects / Bioactivities
DescriptorIDDefinitionReference
analgesic35480 An agent capable of relieving pain without the loss of consciousness or without producing anaesthesia. In addition, analgesic is a role played by a compound which is exhibited by a capability to cause a reduction of pain symptoms.DUKE
ancylostomicideDUKE
anti helmintic33281 A substance that kills or slows the growth of microorganisms, including bacteria, viruses, fungi and protozoans.DUKE
anti flatulent52217 Any substance introduced into a living organism with therapeutic or diagnostic purpose.DUKE
anti malarial33281 A substance that kills or slows the growth of microorganisms, including bacteria, viruses, fungi and protozoans.DUKE
carcinogenic50903 A role played by a chemical compound which is known to induce a process of carcinogenesis by corrupting normal cellular pathways, leading to the acquistion of tumoral capabilities.DUKE
carminativeDUKE
fungicide24127 A substance used to destroy fungal pests.DUKE
nematicide25491 A substance used to destroy pests of the phylum Nematoda (roundworms).DUKE
pesticide25944 Strictly, a substance intended to kill pests. In common usage, any substance used for controlling, preventing, or destroying animal, microbiological or plant pests.DUKE
plasmodicideDUKE
sedative35717 A central nervous system depressant used to induce drowsiness or sleep or to reduce psychological excitement or anxiety.DUKE
transdermalDUKE
trypanocideDUKE
vermifuge25944 Strictly, a substance intended to kill pests. In common usage, any substance used for controlling, preventing, or destroying animal, microbiological or plant pests.DUKE
EnzymesNot Available
PathwaysNot Available
MetabolismNot Available
BiosynthesisNot Available
Organoleptic Properties
FlavoursNot Available
Files
MSDSNot Available
References
Synthesis ReferenceNot Available
General ReferenceNot Available
Content Reference— Duke, James. 'Dr. Duke's Phytochemical and Ethnobotanical Databases. United States Department of Agriculture.' Agricultural Research Service, Accessed April 27 (2004).