ChemFOnt: Showing chemical card for Ascaridole (CFc000016767)

Record Information

Version

1.0

Creation Date

2022-08-28 10:25:12 UTC

Update Date

2022-09-13 19:06:28 UTC

Chemfont ID

CFc000016767

Molecule Identification

Common Name

Ascaridole

Definition

Ascaridole 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

MOL SDF PDB SMILES InChI

Synonyms

Value	Source
1,4-Epidioxy-p-menth-2-ene	ChEBI
1,4-Peroxido-p-menthene-2	ChEBI
1,4-Peroxy-p-menth-2-ene	ChEBI
1-Isopropyl-4-methyl-2,3-dioxabicyclo[2.2.2]oct-5-ene	ChEBI
1-Methyl-4-(1-methylethyl)-2,3-dioxabicyclo[2.2.2]oct-5-ene	ChEBI
1, 4-Epidioxy-P-menth-2-ene	HMDB
1, 4-Peroxy-P-menth-2-ene	HMDB
1,4-Epidioxy-2-P-menthene	HMDB
1-Isopropyl-4-methyl-2,3-dioxabicyclo(2.2.2)oct-5-ene	HMDB
1-Isopropyl-4-methyl-7-oxabicyclo[2.2.1]hept-2-ene	HMDB
1-Methyl-4-(1-methylethyl)-2,3-dioxabicyclo(2.2.2)oct-5-ene	HMDB
1-Methyl-4-(1-methylethyl)-2,3-dioxabicyclo[2.2.2]oct-5-ene, 9ci	HMDB
4-Methyl-1-(propan-2-yl)-2,3-dioxabicyclo[2.2.2]oct-5-ene	HMDB
Ascapurin	HMDB
Ascaricum	HMDB
Ascaridiol	HMDB
Ascaridol	HMDB
Ascaridole (organic peroxide)	HMDB
Ascaridole epoxide	HMDB
Ascarisin	HMDB
Askaridol	HMDB
cis-Ascaridole	HMDB
Kebal II	HMDB
Uncinacina	HMDB

Chemical Formula

C₁₀H₁₆O₂

Average Molecular Weight

168.2328

Monoisotopic Molecular Weight

168.115029756

IUPAC Name

1-methyl-4-(propan-2-yl)-2,3-dioxabicyclo[2.2.2]oct-5-ene

Traditional Name

ascaridole

CAS Registry Number

512-85-6

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 Key

MGYMHQJELJYRQS-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.

Kingdom

Organic compounds

Super Class

Organoheterocyclic compounds

Class

Dioxanes

Sub Class

1,2-dioxanes

Direct Parent

1,2-dioxanes

Alternative Parents

Substituents

Ortho-dioxane
Dialkyl peroxide
Oxacycle
Organic oxygen compound
Hydrocarbon derivative
Organooxygen compound
Aliphatic heteropolycyclic compound

Molecular Framework

Aliphatic heteropolycyclic compounds

External Descriptors

organic heterobicyclic compound (CHEBI:2866 )
organic peroxide (CHEBI:2866 )
p-menthane monoterpenoid (CHEBI:2866 )
Cyclic monoterpenes (C09836 )

Functional Ontology

Physiological effect

Not Available

Disposition

Biological location

Cellular substructure

Route of exposure

Enteral

Ingestion (HMDB: HMDB0035766)

Source

Endogenous

Endogenous (HMDB: HMDB0035766)

Plant

Plant (HMDB: HMDB0035766)

Exogenous

Food

Food (HMDB: HMDB0035766)

Herb and spice

Spice

Cardamom (FooDB: FOOD00074)

Vegetable

Leaf vegetable

Lambsquarters (FooDB: FOOD00394)

Fruit

Fruits (FooDB: FOOD00871)

Exogenous (HMDB: HMDB0035766)

Process

Naturally occurring process

Biological process

Cellular process

Cell signaling (HMDB: HMDB0035766)

Role

Industrial applicationBiological role

Physical Properties

Predicted Properties

Property	Value	Source
Water Solubility	0.53 g/L	ALOGPS
logP	2.64	ALOGPS
logP	2.64	ChemAxon
logS	-2.5	ALOGPS
pKa (Strongest Basic)	-4.9	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	2	ChemAxon
Hydrogen Donor Count	0	ChemAxon
Polar Surface Area	18.46 Å²	ChemAxon
Rotatable Bond Count	1	ChemAxon
Refractivity	47.6 m³·mol⁻¹	ChemAxon
Polarizability	18.93 Å³	ChemAxon
Number of Rings	2	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	Yes	ChemAxon
Veber's Rule	Yes	ChemAxon
MDDR-like Rule	No	ChemAxon