Sassafras oil, also referred to as Safrole Oil is an organic compound with the formula CH2O2C6H3CH2CH=CH2. It is a colorless oily fluid, albeit debased examples can seem yellow. Safrole Oil can synthesized from the phenylpropanoid, group of common items, it is found in sassafras plants among others. Modest quantities are found in a wide assortment of plants, where it capacities as a characteristic antifeedant. Ocotea pretiosa, which develops in Brazil, and Sassafras albidum, which develops in eastern North America, are the principle normal wellsprings of safrole. It has a trademark “sweet-shop” fragrance. Safrole is also used for synthesis of MDMA (a.k.a. XTC, E, X, Molly) – a psychoactive drug, primarily used recreationally.
Molecular Formula: C10H10O2
IUPAC Name: 5-prop-2-enyl-1,3-benzodioxole
Boiling Point: 255 °C
Melting Point: 8 – 12 °C
Water Solubility: Insoluble
Density: 1.0085 g/cu cm at 22 deg C
Appearance: Pale yellow to yellowish brown liquid
Occurrence of Safrole
Safrole is the principal component of brown camphor (Ocotea cymbarum) oil made from Ocotea pretiosa, a plant growing in Brazil, and sassafras oil made from Sassafras albidum.
Safrole was acquired from various plants, however particularly from the sassafras tree (Sassafras albidum), which is local to North America, and from Japanese star anise (Illicium anisatum, called shikimi in Japan). In 1844, the French scientific expert Édouard Saint-Evre decided safrole’s observational formula. In 1869, the French physicists Édouard Grimaux (1835–1900) and J. Ruotte examined and named safrole. They watched its response with bromine, recommending the nearness of an allyl group. By 1884, the German physicist Theodor Poleck (1821–1906) proposed that safrole was a subsidiary of benzene, to which two oxygen particles were joined as epoxides (cyclic ethers).
In 1885, the Dutch scientific expert Johann Frederik Eijkman (1851–1915) examined shikimol, the fundamental oil that is gotten from Japanese star anise, and he found that, upon oxidation, shikimol framed piperonylic acid, whose essential structure had been resolved in 1871 by the German physicist Wilhelm Rudolph Fittig (1835–1910) and his understudy, the American scientist Ira Remsen (1846–1927). Thus Eijkman induced the right essential structure for shikimol. He additionally noticed that shikimol and safrole had the equivalent experimental formula and had other comparative properties, and accordingly he proposed that they were presumably identical. In 1886, Poleck indicated that upon oxidation, safrole likewise shaped piperonylic corrosive, and in this manner shikimol and safrole were to be sure identical. It stayed to be resolved whether the particle’s C3H5 bunch was a propenyl gathering (R-CH=CH-CH3) or an allyl gathering (R-CH2-CH=CH2). In 1888, the German scientific expert Julius Wilhelm Brühl (1850–1911) discovered that the C3H5 bunch was an allyl gathering.
How safrole is made?
It can be synthesized from catechol first by conversion to methylenedioxybenzene, which is brominated and coupled with allyl bromide.
Safrole is a versatile precursor to many compounds. Examples are N-acylarylhydrazones, isosters, aryl-sulfonamide derivatives, acidic sulfonylhydrazone derivatives, benzothiazine derivatives, and many more.
MDMA Synthesis using Safrole
Safrole is used as a precursor in the synthesis of the drug N-methyl-3,4-methylenedioxyamphetamine (MDMA, Ecstasy). The original MDMA synthesis described in Merck’s patent involves brominating safrole to 1-(3,4-methylenedioxyphenyl)-2-bromopropane and then reacting this adduct with methylamine. Before safrole was banned by the FDA in 1960 for use in food, it was used as a food flavour for its characteristic ‘candy-shop’ aroma. It was used as an additive in root beer, chewing gum, toothpaste, soaps, and certain pharmaceutical preparations.
Safrole exhibits antibiotic and anti-angiogenic functions.
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