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

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 that relieves pain by reducing or blocking pain signals in the brain, commonly used to manage acute or chronic pain, inflammation, and fever, with therapeutic applications in surgery, injury, and disease treatment.	DUKE
Ancylostomicide		An agent that destroys Ancylostoma genus of nematodes, used to treat hookworm infections, reducing intestinal parasite load and alleviating associated symptoms such as anemia and malnutrition.	DUKE
Anti-helmintic	33281	An agent that kills or expels parasitic worms, treating helminthic infections. Therapeutically, it targets intestinal parasites, reducing infection symptoms. Key medical uses include treating roundworm, hookworm, and tapeworm infections.	DUKE
Anti-flatulent	52217	An agent that reduces gas production and alleviates bloating, commonly used to manage digestive disorders such as irritable bowel syndrome (IBS), dyspepsia, and gas-related discomfort.	DUKE
Anti-malarial	33281	An agent that prevents or treats malaria, a disease caused by Plasmodium parasites. It works by targeting the parasite's life cycle, reducing symptoms and preventing transmission. Therapeutically, anti-malarials are used to treat and prevent malaria, as well as to manage related conditions such as babesiosis and toxoplasmosis.	DUKE
Carcinogenic	50903	An agent that causes cancer, damaging cellular DNA and disrupting normal cell growth. It has no therapeutic applications, but understanding its biological role informs cancer prevention and treatment strategies, with key medical uses in oncology research and risk assessment.	DUKE
Carminative		An agent that prevents or relieves gas in the gastrointestinal tract, facilitating its expulsion and combating flatulence, commonly used to soothe digestive issues and alleviate symptoms of bloating and discomfort.	DUKE
Fungicide	24127	An agent that kills or inhibits the growth of fungi, playing a biological role in preventing fungal infections. Therapeutically, it is used to treat fungal diseases, with key medical applications including athlete's foot, ringworm, and candidiasis, as well as agricultural uses to protect crops from fungal damage.	DUKE
Nematicide	25491	An agent that kills nematodes, a type of parasitic worm, used to control infestations in crops and animals, with therapeutic applications in veterinary medicine to treat parasitic infections and promote livestock health.	DUKE
Pesticide	25944	An agent that kills or repels pests, playing a biological role in controlling insect, weed, and fungal populations. Therapeutically, pesticides have limited applications, but some are used to treat ectoparasitic infestations, such as lice and scabies. Key medical uses include topical treatments for head lice and scabies, highlighting their role in managing parasitic infections.	DUKE
Plasmodicide		An agent that kills malaria parasites, playing a crucial role in treating and preventing malaria. Therapeutically, it targets Plasmodium species, and its key medical uses include prophylaxis and treatment of malaria, particularly in endemic areas, helping to reduce transmission and alleviate disease burden.	DUKE
Sedative	35717	An agent that calms nervous activity, reducing anxiety and inducing relaxation. Its biological role is to slow down brain function, promoting sleep and relieving stress. Therapeutically, sedatives are used to manage insomnia, anxiety disorders, and seizures, as well as to prepare patients for medical procedures.	DUKE
Transdermal		A route of administration where active ingredients are delivered through the skin for systemic distribution, used therapeutically to manage conditions like pain, hormone replacement, and smoking cessation, with key medical applications including patches and implants for controlled release of medications.	DUKE
Trypanocide		An agent that kills trypanosomes, used to treat diseases like African sleeping sickness and Chagas disease, caused by Trypanosoma parasites, reducing parasitic infections and associated symptoms.	DUKE
Vermifuge	25944	An agent that expels or destroys intestinal parasites, such as worms, by paralyzing or killing them, commonly used to treat parasitic infections like hookworm, roundworm, and tapeworm infestations.	DUKE