Ascaridol

Ascamycin [91432-48-3] Ascaridole [512-85-6] Aschelminthes Ascochyta cucumis Ascochyta sp. Ascomycetes Ascorbic acid... 

Aucordiug toSch immel i Co, normal American worm-seed oil con lams from 63 to 63 per cent. oI ascaridol, and about 22 per cent, ol cymene. Light oils o( iufcrior qnalitv, duo probably to the quality ol the material distilled, having a specific gravity abont 0 942, contain Item 45 to 50 per cent, of ascaridol aod aboal 36 per cent, ol hvdrooaibons. ii... 

Nelson finds that when ascaridol sutlers rearrangement, cither by healing or by treatment with ferrous snlpbate, there are Iwo other bodies formed besides the glycol described by Schimmel. One of these is also a glyco), which he terms /I-glycoI, to distinguish it from the other one, It has the formula sod is decomposed with the... 

Aceoiaiiig to nci .imine a (. n. tbis oil contain y-eynunic, cineol, and ascaridol, I r.ices of lei penos aiit) plieiiols ain also... 

Ascaridol is the principal constituent of the oil of Chsnopodium ambrosoides, var. anthelminticum. 

On oxidation the glycol yields a dibasic acid, CjgHjgO, called ascaridolic acid (melting-point, 116-5° to 117° C.), and another solid acid, melting at 186° to 187° C., to which Nelson attributes the formula... 

Nelson regards ascaridol as a peroxide possessing the constitution I see below). 

O. Wallach has also examined the constitution of ascaridol. He considers it to be an oxide having the formula II—... 

Using a single-channel chip micro reactor, singlet oxygen is generated by photochemical means in presence of catalytic amounts of Rose Bengal [21]. By [4 -i- 2] cycloaddition of this oxygen species to a-terpinene, the product ascaridole is obtained. 

GL 25] [R 8] [P 27] Continuous micro flow processing avoiding enrichment of the explosive endoperoxide ascaridole was established [21]. 

This review is concerned with the synthesis, spectroscopic characterisation, and reactions of saturated bicyclic peroxides. Four years ago such compounds were virtually unknown, yet the first example 2a had been prepared as early as 1938 by catalytic hydrogenation of the naturally occurring peroxide ascaridole 1 (Eq. 1) l). 

Singlet oxygen adds to cyclic 1,3-dienes to afford 1,4-endoperoxides 609). This type of reaction has first been applied successfully to the synthesis of ascaridole from a-terpinene 610) (6.4) and of the vesicatory compound cantharidine 6U) (6.5) some 25 years ago. 

Dienic hydrocarbons are photooxidized to cyclic peroxides. For example, terpinene is photooxidized to ascaridole peroxide [217] ... 

In the literature, there are also several examples where the specific oxidation reaction is dependent on the presence of a diene. Often the substrates are conjugated dienes where there is simultaneous oxidation of both double bonds. An important prototype of this reaction is the well-known singlet oxygen oxidation of dienes to endoperoxides, for example the oxidation of a-terpinene (4) to ascaridole (5) (equation 1). 

Photooxygenation of a-terpinene 155 in the presence of eosin (equation 87) produces ascaridole 156, a constituent of the essential oil Chenopodium ambrosioides L 1. The ewrfo-peroxide 157 derived from cyclopentadiene is a crystalline solid, stable at —100 °C78 above this temperature it rearranges to a mixture of the bis-epoxide 158 and the epoxyaldehyde 159 (equation 88)79,80. 

Triethyl- and triphenylphosphine have been used for deoxygenation not only of hydroperoxides to alcohols but also of dialkyl peroxides to ethers, of diacyl peroxides to acid anhydrides, of peroxy acids and their esters to acids or esters, respectively, and of endoperoxides to oxides [290] in good to excellent yields. The deoxygenation of ascaridole to l-methyl-4-isopropyl-l,4-oxido-2-cyclohexene [290] was later challenged the product is claimed to be p-cymene instead [668]). 

Arylidene-,6-ionones, triplet oxygen cycloaddition, 199, 201 Aryl phosphites, ozone adducts, 732 Aryl-substituted olefins, selenide-catalyzed epoxidation, 384-5 Ascaridole... 

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