ascaridol
4-methyl-1-(propan-2-yl)-2,3-dioxabicyclo[2.2.2]oct-5-ene
 
Notes:
monoterpene endoperoxide with anthelmintic properties. Said to be the major constit. 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.
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      Product(s):
      512-85-6 Ascaridole
      An organic peroxide which constitutes 60-80% of oil of chenopodium. Anthelmintic.
       
       
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CAS Number: 512-85-6Picture of molecule3D/inchi
ECHA EINECS - REACH Pre-Reg: 208-147-4
FDA UNII: 1718D0GEVJ
Nikkaji Web: J6.277D
XlogP3-AA: 2.30 (est)
Molecular Weight: 168.23592000
Formula: C10 H16 O2
BioActivity Summary: listing
NMR Predictor: Predict (works with chrome or firefox)
Category: natural substances and extractives
 
US / EU / FDA / JECFA / FEMA / FLAVIS / Scholar / Patent Information:
Google Scholar: Search
Google Books: Search
Google Scholar: with word "volatile"Search
Google Scholar: with word "flavor"Search
Google Scholar: with word "odor"Search
Google Patents: Search
US Patents: Search
EU Patents: Search
Pubchem Patents: Search
PubMed: Search
NCBI: Search
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Physical Properties:
Assay: 95.00 to 100.00 % 
Food Chemicals Codex Listed: No
Melting Point: 3.00 to  4.00 °C. @ 760.00 mm Hg
Boiling Point: 112.00 to  115.00 °C. @ 20.00 mm Hg
Boiling Point: 96.00 to  97.00 °C. @ 8.00 mm Hg
Vapor Pressure: 1.783000 mmHg @ 25.00 °C. (est)
Flash Point: 133.00 °F. TCC ( 56.11 °C. )
logP (o/w): 2.244 (est)
Soluble in:
 alcohol
 water, 55.5 mg/L @ 25 °C (est)
Insoluble in:
 water
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Organoleptic Properties:
 
Odor and/or flavor descriptions from others (if found).
 
 
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Cosmetic Information:
None found
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Suppliers:
BOC Sciences
For experimental / research use only.
Ascaridole
Odor: characteristic
Use: An organic peroxide which constitutes 60-80% of oil of chenopodium. Anthelmintic.
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Safety Information:
 
Hazards identification
 
Classification of the substance or mixture
GHS Classification in accordance with 29 CFR 1910 (OSHA HCS)
None found.
GHS Label elements, including precautionary statements
 
Pictogram
 
Hazard statement(s)
None found.
Precautionary statement(s)
None found.
Oral/Parenteral Toxicity:
oral-rat LD50  200 mg/kg
Federation Proceedings, Federation of American Societies for Experimental Biology. Vol. 7, Pg. 252, 1948.

oral-mouse LD50  400 mg/kg
Federation Proceedings, Federation of American Societies for Experimental Biology. Vol. 7, Pg. 252, 1948.

oral-dog LDLo  250 mg/kg
Journal of Pharmacology and Experimental Therapeutics. Vol. 24, Pg. 359, 1925.

Dermal Toxicity:
Not determined
Inhalation Toxicity:
Not determined
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Safety in Use Information:
Category: natural substances and extractives
Recommendation for ascaridol usage levels up to:
 not for fragrance use.
 
Recommendation for ascaridol flavor usage levels up to:
 not for flavor use.
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Safety References:
EPI System: View
Cancer Citations: Search
Toxicology Citations: Search
EPA ACToR: Toxicology Data
EPA Substance Registry Services (SRS): Registry
Laboratory Chemical Safety Summary : 10545
National Institute of Allergy and Infectious Diseases: Data
 4-methyl-1-propan-2-yl-7,8-dioxabicyclo[2.2.2]oct-2-ene
Chemidplus: 0000512856
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References:
 4-methyl-1-propan-2-yl-7,8-dioxabicyclo[2.2.2]oct-2-ene
NIST Chemistry WebBook: Search Inchi
Pubchem (cid): 10545
Pubchem (sid): 134978171
Pherobase: View
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Other Information:
(IUPAC): Atomic Weights of the Elements 2011 (pdf)
Videos: The Periodic Table of Videos
tgsc: Atomic Weights use for this web site
(IUPAC): Periodic Table of the Elements
CHEBI: View
CHEMBL: View
KEGG (GenomeNet): C09836
HMDB (The Human Metabolome Database): HMDB35766
FooDB: FDB014503
Typical G.C.
VCF-Online: VCF Volatile Compounds in Food
ChemSpider: View
Wikipedia: View
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Potential Blenders and core components note
 
None Found
 
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Potential Uses:
None Found
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Occurrence (nature, food, other): note
 boldo leaf oil italy @ 38.63%
Data  GC  Search Trop  Picture
 boldus leaf oil chile @ 21.25%
Data  GC  Search Trop  Picture
 cardamom fruit
Search Trop  Picture
 cardamom seed
Search Trop  Picture
 goosefoot plant
Search Trop  Picture
 wormseed oil
Search Trop  Picture
 wormseed oil america @ 1.98%
Data  GC  Search Trop  Picture
 wormseed oil spain @ 41.1%
Data  GC  Search Trop  Picture
 wormwood oil italy @ trace%
Data  GC  Search Trop  Picture
 yarrow oil greece @ 49.30%
Data  GC  Search Trop  Picture
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Synonyms:
 ascaridole
2,3-dioxabicyclo(2.2.2)oct-5-ene, 1-isopropyl-4-methyl-
2,3-dioxabicyclo(2.2.2)oct-5-ene, 1-methyl-4-(1-methylethyl)-
2,3-dioxabicyclo[2.2.2]oct-5-ene, 1-isopropyl-4-methyl-
2,3-dioxabicyclo[2.2.2]oct-5-ene, 1-methyl-4-(1-methylethyl)-
1,4-epidioxy-2-p-menthene
1,4-epi-dioxy-2-p-menthene
1,4-epi-dioxy-2-para-menthene
1,4-epidioxy-p-menth-2-ene
1,4-epi-dioxy-p-menth-2-ene
1,4-epi-dioxy-para-menth-2-ene
p-menth-2-ene, 1,4-epidioxy-
2-para-menthene-1,4-dioxide
4-methyl-1-(propan-2-yl)-2,3-dioxabicyclo[2.2.2]oct-5-ene
4-methyl-1-propan-2-yl-7,8-dioxabicyclo[2.2.2]oct-2-ene
1-methyl-4-(1-methyl ethyl)-2,3-dioxabicyclo(2.2.2)oct-5-ene
1-methyl-4-(1-methylethyl)-2,3-dioxabicyclo(2.2.2)oct-5-ene
1-methyl-4-(1-methylethyl)-2,3-dioxabicyclo[2.2.2]oct-5-ene
1-methyl-4-(propan-2-yl)-2,3-dioxabicyclo[2.2.2]oct-5-ene
1-methyl-4-isopropyl-2-cyclohexene-1,4-dioxide
1,4-peroxy-p-menth-2-ene
1-isopropyl-4-methyl-2,3-dioxabicyclo[2.2.2]oct-5-ene
1,4-proxido-2-p-menthene
1,4-proxido-2-para-menthene
Synonyms   Articles   Notes   Search   Top
Articles:
PubMed: Activation of the Endoperoxide Ascaridole Modulates Its Sensitizing Capacity.
PubMed: Combinations of ascaridole, carvacrol, and caryophyllene oxide against Leishmania.
PubMed: The optimal patch test concentration for ascaridole as a sensitizing component of tea tree oil.
PubMed: Simultaneous determination of ascaridole, p-cymene and α-terpinene in rat plasma after oral administration of Chenopodium ambrosioides L. by GC-MS.
PubMed: Innovative intragastric ascaridole floating tablets: Development, optimization, and in vitro-in vivo evaluation.
PubMed: The endoperoxide ascaridol shows strong differential cytotoxicity in nucleotide excision repair-deficient cells.
PubMed: Co-sensitization to ascaridole and tea tree oil.
PubMed: Ascaridole, a sensitizing component of tea tree oil, patch tested at 1% and 5% in two series of patients.
PubMed: Toxic effects of carvacrol, caryophyllene oxide, and ascaridole from essential oil of Chenopodium ambrosioides on mitochondria.
PubMed: Evaluation of tea tree oil quality and ascaridole: a deep study by means of chiral and multi heart-cuts multidimensional gas chromatography system coupled to mass spectrometry detection.
PubMed: Antitumor activity of the essential oil from the leaves of Croton regelianus and its component ascaridole.
PubMed: Ascaridole and related peroxides from the genus Chenopodium.
PubMed: Activity of ascaridol from the anthelmintic herb Chenopodium anthelminticum L. against sensitive and multidrug-resistant tumor cells.
PubMed: Biosynthesis of ascaridole: iodide peroxidase-catalyzed synthesis of a monoterpene endoperoxide in soluble extracts of Chenopodium ambrosioides fruit.
PubMed: Ascaridole-less infusions of Chenopodium ambrosioides contain a nematocide(s) that is(are) not toxic to mammalian smooth muscle.
PubMed: The effect of ascaridole on the in vitro development of Plasmodium falciparum.
PubMed: Essential oil from Chenopodium ambrosioides and main components: activity against Leishmania, their mitochondria and other microorganisms.
PubMed: Antileishmanial activity of essential oil from Chenopodium ambrosioides and its main components against experimental cutaneous leishmaniasis in BALB/c mice.
PubMed: On the effect of ascaridole on the inner ear electrobiological and histological studies on the localization of the cochlear microphone effect.
PubMed: Ascaridole in oil of chenopodium; the characterization of ascaridole.
PubMed: Ascaridole in chenopodium oil. IV. The synthesis of ascaridole.
PubMed: Determination and pharmacokinetics of ascaridole in rat plasma by gas chromatography-mass spectrometry.
PubMed: Combined analysis of the essential oil of Chenopodium ambrosioides by GC, GC-MS and 13C-NMR spectroscopy: quantitative determination of ascaridole, a heat-sensitive compound.
PubMed: Chenopodium ambrosioides L. Reduces Synovial Inflammation and Pain in Experimental Osteoarthritis.
PubMed: Ascaridol in oil of chenopodium.
PubMed: An investigation of the assay of ascaridol; the iodination of terpenes.
PubMed: Kinetics of dissociative electron transfer to ascaridole and dihydroascaridole-model bicyclic endoperoxides of biological relevance.
PubMed: Chemical composition, antimicrobial and insecticidal activities of the essential oils of Conyza linifolia and Chenopodium ambrosioides.
PubMed: Supercritical CO₂ extract and essential oil of aerial part of Ledum palustre L.--Chemical composition and anti-inflammatory activity.
PubMed: Ascaridole as a pharmacologically active principle of "Paico," a medicinal Peruvian plant.
PubMed: Amoebicidal Activity of Essential Oil of Dysphania ambrosioides (L.) Mosyakin & Clemants in an Amoebic Liver Abscess Hamster Model.
PubMed: [Quantitative determination of ascaridol using gas-liquid chromatography].
PubMed: [Treatment of ascaridiasis with the synthetic ascaridol preparation ascarisin].
PubMed: [Methods of determination of ascaridol in oil of Chenopodium].
PubMed: Effect of heat and light on the ascaridol content in oil of chenopodium.
PubMed: [Research on the photo-oxidation of alpha-terpinene & ascaridol in the presence of furo [2,3-g] coumarin & other photodynamic drugs].
PubMed: Analyses of drugs and chemicals by infrared absorption spectra. I. Quantitative analyses of santonin, thymol, tetrachloroethylene, and ascaridol in mixed drugs.
PubMed: [Determination of ascaridol in oleum Chenopodii. I. Determination by ultrared absorption spectroscopy].
PubMed: Ascaridole studies. II. An examination of the iodimetric and polarographic methods of determination of ascaridole.
PubMed: Ascaridole studies. III. The purification and characterisation of ascaridole.
PubMed: A note on the determination of ascaridole in oil of chenopodium.
PubMed: The determination of ascaridole in oil of chenopodium and in solution of oil of chenopodium in castor oil.
PubMed: Note on a micromethod for the estimation of ascaridole.
PubMed: [Iodometric determination of ascaridole and Chenopodium oil].
PubMed: A note on the assay of ascaridole in castor oil solution.
PubMed: Evaluation of Essential Oil and its Three Main Active Ingredients of Chinese Chenopodium ambrosioides (Family: Chenopodiaceae) against Blattella germanica.
PubMed: Composition of seed essential oils of Rhododendron tomentosum.
PubMed: Composition of essential oil of Chinese Chenopodium ambrosioides and insecticidal activity against maize weevil, Sitophilus zeamais.
PubMed: Bioactivities of volatile components from Nepalese Artemisia species.
PubMed: Immobilized organic photosensitizers with versatile reactivity for various visible-light applications.
PubMed: π-Conjugated polyHIPEs as highly efficient and reusable heterogeneous photosensitizers.
PubMed: HPLC determination of the major active flavonoids and GC-MS analysis of volatile components of Dysphania graveolens (Amaranthaceae).
PubMed: Chemical composition and insecticidal activity of plant essential oils from Benin against Anopheles gambiae (Giles).
PubMed: Studies on the traditional herbal anthelmintic Chenopodium ambrosioides L.: ethnopharmacological evaluation and clinical field trials.
PubMed: Photoactive, porous honeycomb films prepared from Rose Bengal-grafted polystyrene.
PubMed: Detection and identification of 1-methylethyl and methyl radicals generated by irradiating tea tree (Melaleuca alternifolia) oil with visible light (436 nm) in the presence of flavin mononucleotide and ferrous ion.
PubMed: Composition and Antimicrobial Activity of the Essential Oil from Leaves of Curcuma longa L. Kasur Variety.
PubMed: Chemometric profile of root extracts of Rhodiola imbricata Edgew. with hyphenated gas chromatography mass spectrometric technique.
PubMed: Sensitization assays: monocyte-derived dendritic cells versus a monocytic cell line (THP-1).
PubMed: Larvicidal and nematicidal activities of the leaf essential oil of Croton regelianus.
PubMed: Essential oil composition of five collections of Achillea biebersteinii from central Turkey and their antifungal and insecticidal activity.
PubMed: Degradation products of monoterpenes are the sensitizing agents in tea tree oil.
PubMed: Composition and antifungal activity of the essential oil of the Brazilian Chenopodium ambrosioides L.
PubMed: Comparative chemical, cytotoxicity and antileishmanial properties of essential oils from Chenopodium ambrosioides.
PubMed: Herbicidal activity of Peumus boldus and Drimys winterii essential oils from Chile.
PubMed: Monoterpene hydroperoxides with trypanocidal activity from Chenopodium ambrosioides.
PubMed: Volatile constituents and antibacterial screening of the essential oil of Chenopodium ambrosioides L. growing in Nigeria.
PubMed: Seasonal and phenological variations of the essential oil from the narrow endemic species Artemisia molinieri and its biological activities.
PubMed: Misidentification of tansy, Tanacetum macrophyllum, as yarrow, Achillea grandifolia: a health risk or benefit?
PubMed: [Fatal poisoning caused by oil of epazote, Chenopodium graveolens].
PubMed: Terpenes and the lipid-protein-partitioning theory of skin penetration enhancement.
PubMed: Studies of Genetic Variation of Essential Oil and Alkaloid Content in Boldo (Peumus boldus).
PubMed: On agents favoring prostaglandin f formation during biosynthesis.
PubMed: Homogeneous photochemical oxidation via singlet O2 in supercritical CO2.
PubMed: Hydroquinone derivatives and monoterpenoids from the Neotropical liverwort Plagiochila rutilans.
PubMed: The chemotherapy of rodent malaria. XLVIII. The activities of some synthetic 1,2,4-trioxanes against chloroquine-sensitive and chloroquine-resistant parasites. Part 1: Studies leading to the development of novel cis-fused cyclopenteno derivatives.
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