Allyl-3,4-methylenedioxybenzene

The 3,4-methylenedioxy pattern. One of the most famous essential oils is safrole, or 4-allyl-1,2-methylenedioxybenzene. This is the mainstay of sassafras oil, and it and its conjugated isomer isosafrole have a smell that is immediately familiar root beer These are among the most widely distributed essential oils, being present in most of... 

Allyl 3-methyl butyrate. See Allyl isovalerate 1-Allyl-3,4-methylenedioxybenzene 4-Allyl-1,2-methylenedioxybenzene. See Safrol (1S)-3-Allyl-2-methyl-4-oxocyclopent-2-enyl-(1 R)-trans-chrysanthemate. See,S-Bioallethrin 3-Allyl-2-methyl-4-oxo-2-cyclopenten-1-yl chrysanthemate dl-3-Allyl-2-methyl-4-... 

CAS 94-59-7 EINECS/ELINCS 202-345-4 Synonyms 5-Allyl-1,3-benzodioxole Allylcatechol methylene ether Allyidioxybenzene methylene ether 1-Allyl-3,4-methylenedioxybenzene 4-Allyl-1,2-methylenedioxybenzene m-Allylpyrocatechin methylene ether Allylpyrocatechol methylene ether 1,2-Methylenedioxy-4-allylbenzene 3,4-Methylenedioxy allylbenzene 3,4-Methylenedioxy-1-allylbenzene 5-(2-Propenyl)-1,3-benzodioxole Safrole Empiricai C10H10O2 Formuia C3H5C6H3O2CH2 Properties Colorless vise. liq. orcryst. sassafras odor very sol. in alcohol misc. with chloroform, ether, chlorinated solvs. insol. in water m.w. 162.20 dens. 1.0960 (20 C) m.p. 11 C b.p. 234.5 C flash pt. 100 C ref. index 1.5360-1.5385 Toxicoiogy LD50 (oral, rat) 1950 mg/kg,... 

Fumigatin [484-89-9] (3-hydroxy-2-methoxy-5-methyl-y)-benzoquiQone) is isolated from metaboHsm oiyispergillusfumigatus and is used as an antimicrobial. 5-Allyl-1,6-dimethoxy-2,3-methylenedioxybenzene (diUapiole) (62) is a synergist for pyrethmm. Derivatives have been prepared and evaluated (216). 

Safrole (5-allyl-l,3-benzodioxole, 4-allyl-l,2-methylenedioxybenzene) [94-59-7] M 162.1, m- 11 , b 69-70 /1.5mm, 104-105 /6mm, 231.5-232 /atm, 235-237 /atm, dj 1.0993, n, 1.53738. It has been purified by fractional distn, although it has also been recrystd from low boiling pet ether at low temperatures. [IR Briggs et al. Anal Chem 29 904 19S7 UV Patterson and Hibbert J Am Chem Soc 65 1962 1943.] The maleic anhydride adduct forms yellow crystals from toluene m 257° [Hickey J Org Chem 13 443 1948], and the picrate forms orange-red crystals from CHCI3 [Baril and Magrdichian 7/4m Chem Soc 5S 1415 1936]. 

Myristicin, CjjHjgOg, is 4-allyl-6-methoxy-l. 2-methylenedioxybenzene. It is found in oil of nutmeg and in parsley oil. It is a fragrant compound having the following characters —... 

The edible parts of parsnips (Pastimea sativa L.), which have been consumed for centuries by humans without causing any obvious harm, were found to contain a chemical of insecticidal and strong synergistic nature (1). The insecticidal constituent, present at about 200 p.p.m., was isolated and identified as 5-allyl-l-methoxy-2, 3-methylenedioxybenzene or myristicin. Its toxicity to various insects [vinegar flies, houseflies, Mediterranean fruit flies, mosquito larvae, Mexican bean beetles, and pea aphids] was established and compared with pyrethrum and aldrin (Tables I and II). The knockdown effect, although definite, was not as great as that of pyrethrum. In tests... 

SYNTHESIS Apiole, as the crystalline essential oil l-allyl-2,5-dimethoxy-3,4-methylenedioxybenzene, is isolated directly from commercial Oil of Parsley, by... 

The 3,4-methylenedioxy pattern. One of the most famous essential oils is safrole, or 4-allyl-l,2-methylenedioxybenzene. This is the mainstay of sassafras... 

ALLYL 3-METHYLBUTYRATE see ISVOOO l-ALLYL-3,4-METHYLENEDIOXYBENZENE see SADOOO... 

Beilstein Handbook Reference) 1-Allyl-2,5-dimethoxy-3,4-methylenedioxybenzene 5-Allyl-4,7-dimethoxy-1,3-benzodioxol 5-Allyl-4,7-dimethoxy-1,3-benzodioxole AI3-14843 Apiol Apiole Apiole (parsley) Apioline Benzene. 1-allyl-2.5-dimethoxy-3,4-(methyl-enedioxy)- I. Benzodioxole, 4,7-dimethoxy-5- 2-propenyl)- BRN 0195747 EINECS 208-349-2 NSC 9070 Parsley apiol Parsley apiole Parsley camphor Petersiliencampher. Is synergistic with insecticides. Needles mp n 29.5° bp = 294°, bp35... 

METHYLENE ETHER l-ALLYL-3,4-METHYLENEDIOXYBENZENE 4-ALLYL-1,2-METHYLENEDI0XYBENZENE m-ALLYLPYROCATECHIN METHYLENE ETHER 4-ALLYLPYROCATECHOL FORMALDEHYDE ACETAL ALLYLPYROCATECHOL METHYLENE ETHER l,2-METHYLENEDIOXY-4-ALLYLBENZENE 3,4-METHYLENEDIOXY-ALLYBENZENE 5-(2-PROPENYL)-l,3-BENZODIOXOLE RHYUNO OIL SAFROLE SAFROLE ME SHIKIMOLE SHDCOMOL... 

SYNTHESIS Apiole, as the crystalline essential oil 1-allyl-2,5-dimethoxy-3,4-methylenedioxybenzene, is isolated directly from commercial Oil of Parsley, by careful fractional distillation. It is the fraction that boils at 165-167 °C at 27 mm/Hg. A solution of 19.8 g apiole in a mixture of 43 g KOH and 60 mL hot EtOH was heated in the steam bath for 24 h. With vigorous stirring, it was diluted with H20, at a rate which the crystals that formed spontaneously could accumulate from the turbidity that was generated. When no more H20 could be added (there was persistent oiling out of material) the reaction mixture was filtered to give 12.1 g of an amber solid material. This was recrystallized from 20 mL boiling hexane, which was filtered while hot to remove insolubles. From the cooled filtrate, there was obtained 9.3 g of 2,5-dimethoxy-3,4-methylenedioxy-1-propenylbenzene, isoapiole, as pale cream-colored solids. 

The 2,3-dimethoxy-4,5-methylenedioxy pattern. The second of the three tetraoxygenated essential oils is 1-allyl-2,3-dimethoxy-4,5-methylenedioxybenzene, commonly called dillapiole and it comes, not surprisingly, from the oils of any of the several dill plants around the world. It is a thick, almost colorless liquid, but its isomerization product, isodillapiole, is a white crystalline product which melts sharply. This, by the theoretical addition of ammonia, gives DMMDA-2. 

The 3-methoxy-4,5-methylenedioxy pattern. The parent compound is myristicin, 5-allyl-1-methoxy-2,3-methylenedioxybenzene, and the source of this is nutmeg (or the botanically parallel material, mace). 

A 1961 report, "Toxic and possible carcinogenic effects of 4-allyl-l,2-methylenedioxybenzene (safrole) in rats," led to further in vitro studies that culminated in a ban by the FDA (CFR 2011 Homburger et al. 1961). Safrole s potential damage of DNA has not been confirmed in humans, yet it is of such substantial consequence that public health agencies are inclined to err on the side of safety. Safrole is also used as a precursor in the synthesis of the insecticide synergist piperonyl butoxide and for the clandestine manufacture of MDMA (ecstasy) (Barceloux 2008), which raises suspicions about politicization of the regulation. 

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