Showing Compound Ascaridole (FDB014503)

Record Information

Version

1.0

Creation date

2010-04-08 22:11:18 UTC

Update date

2019-11-26 03:10:11 UTC

Primary ID

FDB014503

Secondary Accession Numbers

Not Available

Chemical Information

FooDB Name

Ascaridole

Description

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. Ascaridole is found in cardamom, fruits, and lambsquarters.

CAS Number

512-85-6

Structure

MOL SDF PDB SMILES InChI

Synonyms

Synonym	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
1-methyl-4-(1-methylethyl)-2,3-dioxabicyclo[2.2.2]oct-5-ene	biospider
1-Methyl-4-(1-methylethyl)-2,3-dioxabicyclo[2.2.2]oct-5-ene, 9CI	db_source
1, 4-Epidioxy-p-menth-2-ene	biospider
1, 4-Peroxy-p-menth-2-ene	biospider
1,4-Epidioxy-2-p-menthene	biospider
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-ene	biospider
Ascaridole (organic peroxide) [forbidden]	biospider
Cis-ascaridole	biospider
p-Menth-2-ene, 1,4-epidioxy-	biospider

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

Chemical Formula

C10H16O2

IUPAC name

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

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

Isomeric SMILES

CC(C)C12CCC(C)(OO1)C=C2

Average Molecular Weight

168.2328

Monoisotopic Molecular Weight

168.115029756

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.

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 )

Ontology

Disposition

Route of exposure:

Enteral:

Ingestion

Source:

Biological:

Plant

Biological location:

Cell and elements:

Extracellular

Subcellular:

Process

Naturally occurring process:

Biological process:

Cellular process:

Cell signaling

Role

Industrial application:

Biological role:

Physico-Chemical Properties - Experimental

Property	Value	Reference
Physical state	Liquid
Physical Description	Not Available
Mass Composition	C 71.39%; H 9.59%; O 19.02%	DFC
Melting Point	Mp 3.3°	DFC
Boiling Point	Bp0.2 39-40°	DFC
Experimental Water Solubility	Not Available
Experimental logP	Not Available
Experimental pKa	Not Available
Isoelectric point	Not Available
Charge	Not Available
Optical Rotation	Not Available
Spectroscopic UV Data	Not Available
Density	d204 1.01	DFC
Refractive Index	Not Available

Spectra

EI-MS/GC-MS

Type	Description	Splash Key	View
Predicted GC-MS	Ascaridole, non-derivatized, Predicted GC-MS Spectrum - 70eV, Positive	splash10-004i-2900000000-4e6342ba9b29d1dd42ad	Spectrum
Predicted GC-MS	Ascaridole, non-derivatized, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Ascaridole, non-derivatized, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum

MS/MS

Type	Description	Splash Key	View
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-014i-0900000000-83d7b2bd24b624b5ea98	2016-08-03	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-014i-0900000000-1d0d1c7edaaa69d194a1	2016-08-03	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-0udi-0900000000-2c78632dd190511927b9	2016-08-03	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-014i-0900000000-177dc272267c0f543701	2016-08-03	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-014i-0900000000-3317598e1aa469191e58	2016-08-03	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-0adi-0900000000-fb70c59640ba1c0d01a6	2016-08-03	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-014i-0900000000-cb7592114e600c180aec	2021-09-25	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-014i-0900000000-cb7592114e600c180aec	2021-09-25	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-014i-0900000000-3a7e13f32c837bc356ac	2021-09-25	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-014i-0900000000-f9b2951dd69b378c6031	2021-09-25	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-016r-0900000000-460c95031436dfd1e1b7	2021-09-25	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-004i-0900000000-6a28e536e83eb1686dba	2021-09-25	View Spectrum

NMR

Not Available

External Links

ChemSpider ID

ChEMBL ID

KEGG Compound ID

Pubchem Compound ID

Pubchem Substance ID

Not Available

ChEBI ID

2866

Phenol-Explorer ID

Not Available

DrugBank ID

Not Available

HMDB ID

HMDB35766

CRC / DFC (Dictionary of Food Compounds) ID

JRL78-N:JRL78-N

EAFUS ID

Not Available

Dr. Duke ID

ASCARIDOLE

BIGG ID

Not Available

KNApSAcK ID

C00003027

HET ID

Not Available

Food Biomarker Ontology

Not Available

VMH ID

Not Available

Flavornet ID

Not Available

GoodScent ID

Not Available

SuperScent ID

Not Available

Wikipedia ID

Ascaridole

Phenol-Explorer Metabolite ID

Not Available

Duplicate IDS

Not Available

Old DFC IDS

Not Available

Associated Foods

Food	Content Range	Average	Reference
Food			Reference

Biological Effects and Interactions

Health Effects / Bioactivities

Descriptor	ID	Definition	Reference
analgesic	35480	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
ancylostomicide			DUKE
anti helmintic	33281	A substance that kills or slows the growth of microorganisms, including bacteria, viruses, fungi and protozoans.	DUKE
anti flatulent	52217	Any substance introduced into a living organism with therapeutic or diagnostic purpose.	DUKE
anti malarial	33281	A substance that kills or slows the growth of microorganisms, including bacteria, viruses, fungi and protozoans.	DUKE
carcinogenic	50903	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
carminative			DUKE
fungicide	24127	A substance used to destroy fungal pests.	DUKE
nematicide	25491	A substance used to destroy pests of the phylum Nematoda (roundworms).	DUKE
pesticide	25944	Strictly, a substance intended to kill pests. In common usage, any substance used for controlling, preventing, or destroying animal, microbiological or plant pests.	DUKE
plasmodicide			DUKE
sedative	35717	A central nervous system depressant used to induce drowsiness or sleep or to reduce psychological excitement or anxiety.	DUKE
transdermal			DUKE
trypanocide			DUKE
vermifuge	25944	Strictly, a substance intended to kill pests. In common usage, any substance used for controlling, preventing, or destroying animal, microbiological or plant pests.	DUKE