4-Allyl-l,2-methylenedioxybenzene

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]. 

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... 

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. 

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 —... 

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 l-allyl-2,5-dimethoxy-3,4-methylenedioxybenzene, is isolated directly from commercial Oil of Parsley, by... 

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