Isosafrole: Difference between revisions

Latest revision as of 10:48, 15 February 2025

Isosafrole[edit]

Isosafrole is an organic compound that is classified as a phenylpropene, a type of phenylpropanoid. It is a colorless to slightly yellow liquid with a characteristic odor. Isosafrole is primarily used in the synthesis of piperonal, which is a precursor for the production of fragrances and flavors.

Chemical Properties[edit]

Isosafrole is a member of the methylenedioxyphenyl family, which includes compounds such as safrole and myristicin. Its chemical formula is C10H10O2, and it has a molar mass of 162.19 g/mol. The compound is characterized by the presence of a methylenedioxy group attached to a phenyl ring, which is further connected to a propenyl side chain.

Synthesis[edit]

Isosafrole can be synthesized from safrole through an isomerization process. This involves the rearrangement of the allyl group in safrole to form the propenyl group in isosafrole. The reaction is typically catalyzed by acids or bases and can be carried out under various conditions to optimize yield and purity.

Uses[edit]

The primary use of isosafrole is in the production of piperonal, which is widely used in the fragrance industry. Piperonal, also known as heliotropin, has a floral scent reminiscent of vanilla and almond, making it a popular ingredient in perfumes and flavorings.

Safety and Regulation[edit]

Isosafrole is subject to regulation due to its potential use in the illicit synthesis of MDMA (3,4-methylenedioxy-N-methylamphetamine), a psychoactive drug. As a result, its production and distribution are monitored in many countries to prevent its diversion for illegal purposes.

Related Compounds[edit]

Related Pages[edit]

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-{{png-image}}
+== Isosafrole ==
-'''Isosafrole''' is an [[organic compound]] with the formula C<sub>10</sub>H<sub>10</sub>O<sub>2</sub>. It is a colorless or slightly yellow oily liquid with a characteristic smell and is one of the key components in the synthesis of the [[psychedelic]] drug [[MDMA]] (commonly known as ecstasy). Isosafrole is found naturally in small quantities in various essential oils, most notably in [[sassafras]] oil, from which it was historically derived. However, due to its use in the illicit manufacture of MDMA, the production and sale of isosafrole are regulated in many countries.
-==Properties==
+[[File:Isosafrole_acsv.svg|thumb|right|Chemical structure of Isosafrole]]
-Isosafrole is an isomer of [[safrole]], another compound found in sassafras oil. It has a boiling point of 253°C and a density of 1.122 g/cm³. Isosafrole is slightly soluble in water but mixes well with most organic solvents.
-==Synthesis==
+'''Isosafrole''' is an organic compound that is classified as a phenylpropene, a type of [[phenylpropanoid]]. It is a colorless to slightly yellow liquid with a characteristic odor. Isosafrole is primarily used in the synthesis of [[piperonal]], which is a precursor for the production of fragrances and flavors.
-Isosafrole can be synthesized from safrole through isomerization, which can be achieved using a strong base or by heating. In the industrial synthesis of MDMA, isosafrole is often oxidized to [[piperonal]], which then undergoes several more steps to produce the final product.
-==Regulation==
+== Chemical Properties ==
-Due to its association with the synthesis of MDMA, isosafrole is listed as a [[List I chemical]] under the United States Controlled Substances Act, meaning that sales and imports are tightly controlled. Similar regulations exist in other countries to prevent its misuse.
-==Uses==
+Isosafrole is a member of the [[methylenedioxyphenyl]] family, which includes compounds such as [[safrole]] and [[myristicin]]. Its chemical formula is C10H10O2, and it has a molar mass of 162.19 g/mol. The compound is characterized by the presence of a methylenedioxy group attached to a phenyl ring, which is further connected to a propenyl side chain.
-Historically, isosafrole was used in the manufacture of fragrances and as a flavoring agent due to its pleasant aroma. However, its use in the food and cosmetic industry has significantly declined due to health concerns and regulatory restrictions. Today, its legitimate use is primarily limited to research and industrial applications not related to drug synthesis.
-==Health Effects==
+== Synthesis ==
-Isosafrole has been shown to have hepatotoxic and carcinogenic effects in animal studies. The International Agency for Research on Cancer (IARC) has classified isosafrole as a Group 2B carcinogen, indicating it is possibly carcinogenic to humans. Exposure to isosafrole should be minimized, and safety precautions should be taken when handling it.
+Isosafrole can be synthesized from [[safrole]] through an isomerization process. This involves the rearrangement of the allyl group in safrole to form the propenyl group in isosafrole. The reaction is typically catalyzed by acids or bases and can be carried out under various conditions to optimize yield and purity.
+== Uses ==
+The primary use of isosafrole is in the production of [[piperonal]], which is widely used in the fragrance industry. Piperonal, also known as heliotropin, has a floral scent reminiscent of [[vanilla]] and [[almond]], making it a popular ingredient in perfumes and flavorings.
+== Safety and Regulation ==
+Isosafrole is subject to regulation due to its potential use in the illicit synthesis of [[MDMA]] (3,4-methylenedioxy-N-methylamphetamine), a psychoactive drug. As a result, its production and distribution are monitored in many countries to prevent its diversion for illegal purposes.
+== Related Compounds ==
+* [[Safrole]]
+* [[Piperonal]]
+* [[Myristicin]]
+* [[Eugenol]]
+== Related Pages ==
+* [[Phenylpropene]]
+* [[Fragrance]]
+* [[Organic chemistry]]
+[[Category:Phenylpropanoids]]
 [[Category:Organic compounds]]
-[[Category:Phenylpropanoids]]
-{{chemistry-stub}}