1- Methoxy-4-allylbenzene

Nutmeg Oil - contains 0-3% safrole, and 0-13% myristicin (3,4-methylene-dioxy-5-methoxy allylbenzene. The boiling point at 15 torr is 150 °C. Yield MMDA, dosage 80 mg. 

Parsley Seed Oil - contains 0-80% parsley apiol (2-methoxy-3,4-methylene-dioxy-5-methoxy-allylbenzene). Its boiling point is 292 °C at normal pressure, and 179 C at 34 torr. It yields DMMDA, dosage about 75 mg. This oil may also contain 10-77% myristicin. 

Although l,2-methylenedioxy-4-allylbenzene and 1,2-methylenedioxy-4-prope-nylbenzene are really heterocyclic compounds, they are discussed here because of their close biogenetic relationship to the 2-methoxy-4-alkenylphenols. 

Another fraction of American sulfate turpentine oil (1% of the total) consists essentially of an azeotropic mixture of estragole (l-methoxy-4-allylbenzene / lOi.SkPa 216 °C) and a-terpineol. Treatment with potassium hydroxide yields a mixture of anethole isomers and a-terpineol, which can be separated by fractional distillation. 

The Mn(III) complex 31b was tested as a catalyst for the epoxidation of various alkenes using sodium hypochlorite or iodosylbenzene as oxidants. Although oxidation took place, no selectivity was observed. For example, allylresorcinol was not epoxidized with rates higher than that of allylbenzene. Presumably, the substrate is not bound in the cleft of 31b because the latter is occluded by methoxy groups. It is possible that the reaction occurs on the outside of the metalloclip, which cannot discriminate between guest molecules. 

EXTENSIONS AND COMMENTARY This is another of the essential amphetamines, because of the appearance of the 4-methoxy group in two most important essential oils. These are the allylbenzene (estragole or esdragol) and the propenyl isomer (anethole). Their natural sources have been discussed under TM A. 

Bis[2-methoxy-3-phenylpropyl] Ditellurium4 2.0 g tellurium dioxide (12.5 mmol) are dissolved in 10 ml concentrated hydrochloric acid. The yellow solution is diluted with 40 ml methanol. 1.75 mg (14.8 mmol) allylbenzene are addded, the mixture is refluxed for 24 h, and then cooled to 20°. The yellowish homogeneous solution is poured into a separatory funnel containing 5 g disodium disulfitc in 100 ml water and 100 m/ dichloromethane. The mixture is shaken, the red dichloromethane phase separated, dried, and evaporated. The red, oily residue is flash chromatographed on silica gel with dichloromethane as the mobile phase yield 80%. 

Methoxy-3-phenylpropyl Tellurium Trichloride1 2.0 g (12.5 mmol) tellurium dioxide are dissolved in 10 m/ concentrated hydrochloric acid and 40 ml methanol are added. 1.75 g (14.8 mmol) of allylbenzene are added. The mixture is refluxed for 24 h and then cooled to 20°. This solution containing the 2-methoxy-3-phenylpropyl tellurium trichloride was reduced with aqueous disodium disulfite to the ditellurium compound. 

SYNS 4-ALLYLGUAtACOL 4-ALLYL-l-HYDROXY-2-METHOXYBENZENE 4-ALLYL-2-METHOXYPHENOL CARYOPHYLLIC ACID EUGENIC ACID Fa 100 FEMA No. 2467 1-HYDROXY-2-METHOXY-4-ALLYLBENZENE 4-HYDROXY-3-METHOXYALLYLBENZENE 1-HYDROXY-2-METHOXY-4-PROP-2-ENYLBENZENE 2-METHOXY-4-ALLYLPHENOL 2-METHOXY-4-PROP-2-ENYLPHENOL 2-METHOXY-4-(2-PROPENYL)PHENOL 2-METOKSY-4-ALULOFENOL (POUSH) NCI-C50453 SYNTHETIC EUGENOL... 

SYNS ACETEUGENOL 1-ACETOXY-2-METHOXY-4-ALLYLBENZENE ACETYLEUGENOL 4-ALLYL-2-METHOXYPHENOL ACETATE 1,3,4-EUGENOL ACETATE EUGENYL ACETATE FEMA No. 2469... 

The volatile oils in nutmeg consist of allylbenzene derivatives and terpines. Myristicin, elemicin, and safrole comprise 80% of the allylbenzenes. Myristicin and elemicin may be biotransformed into MMDA (3-methoxy-4,5-dimethylene-dioxampheta-mine) and TMA (3,4,5-trimethoxyamphetamine), respectively, both consisting of a difference of only an amine group added to the side chain. Symptoms occur within 3-8 h, followed by 6-24 h of alternating periods of stupor and delirium. Recovery normally occurs within 24 h but may take several days. 

Another fraction of American sulfate turpentine oil (1 % of the total) consists essentially of an azeotropic mixture of estragole (l-methoxy-4-allylbenzene... 

Synonyms Allylguaiacol 4-Allylguaiacol 4-Allyl-1-hydroxy-2-methoxybenzene 4-Allyl-2-methoxyphenol Caryophyllic acid Eugenic acid 1-Hydroxy-2-methoxy-4-allylbenzene 4-Hydroxy-3-methoxyallylbenzene 1 -Hydroxy-2-methoxy-4-prop-2-enylbenzene 2-Methoxy-4-allylphenol 2-Methoxy-4-(2-propenyl) phenol 2-Methoxy-4-prop-2-enylphenol Phenol, 2-methoxy-4-(2-propenyl)-... 

Synonyms Aceteugenol 1-Acetoxy-2-methoxy-4-allylbenzene 3-(4-Acetoxy-3-methoxyphenyl) propene Acetyl eugenol 4-Allyl-2-methoxyphenyl acetate Eugenol acetate 1,3,4-Eugenol acetate 4-(2-Propenyl)-2-methoxyphenyl ethanoate Empirical C12H14O3... 

Hydroxymethanesulfinic acid monosodium salt Hydroxymethanesulfinic acid sodium salt. See Sodium formaldehyde sulfoxylate Hydroxymethanesulfonic acid, monosodium salt. See Sodium hydroxymethane sulfonate 1-Hydroxy-2-methoxy-4-allylbenzene 4-Hydroxy-3-methoxyallylbenzene. See Eugenol 4-Hydroxy-3-methoxybenzaldehyde. See Vanillin... 

Parsley fruit oil Petroselinum sativum Fruit SD Myristicine (methoxy safrole), apiole (dimethoxy safrole), 2,3,4,5-tetramethoxy allylbenzene... 

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