ascaridol

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

CAS: 512-85-6 C10 H16 O2 MW: 168.23592000

Identification

Nameascaridol
IUPAC4-methyl-1-propan-2-yl-7,8-dioxabicyclo[2.2.2]oct-2-ene
CAS Number512-85-6
EINECS208-147-4
FDA UNII1718D0GEVJ
Molecular FormulaC10 H16 O2
Molecular Weight168.23592000
Nikkaji NumberJ6.277D

Regulatory

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, 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
Insoluble in water

No sensory data available

Safety Information

Oral/Parenteral Toxicityoral-rat LD50 200 mg/kg
Dermal ToxicityNot determined
Inhalation ToxicityNot determined

GHS Classification

['GHS Classification in accordance with 29 CFR 1910 (OSHA HCS)', 'GHS Label elements, including precautionary statements']

Safety in Use

Categorynatural substances and extractives
Recommendation for ascaridol usage levels up tonot for fragrance use.
Recommendation for ascaridol flavor usage levels up tonot for flavor use.

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Potential Uses

None Found

Natural Occurrence

boldo leaf oil italy @ 38.63% Data boldus leaf oil chile @ 21.25% Data cardamom fruit cardamom seed goosefoot plant wormseed oil wormseed oil america @ 1.98% Data wormseed oil spain @ 41.1% Data wormwood oil italy @ trace% Data yarrow oil greece @ 49.30% Data

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-epi dioxy-2-p-menthene 1,4-epi- dioxy-2-p-menthene 1,4-epi- dioxy-2-para-menthene 1,4-epi dioxy-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-iso propyl-4-methyl-2,3-dioxabicyclo[2.2.2]oct-5-ene 1,4- proxido-2-p-menthene 1,4- proxido-2-para-menthene 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.