Heliotropin ( piperonal , 3,4-methylenedioxybenzaldehyde ) - aromatic aldehyde C 8 H 6 O 3 . In its pure form, it represents colorless crystals with the smell of a heliotrope - intermediate between the smells of vanilla and cinnamon.
| Heliotropin | |
|---|---|
 | |
 | |
| Are common | |
| Chem. formula | C 8 H 6 O 3 |
| Physical properties | |
| Molar mass | 150.13 g / mol |
| Thermal properties | |
| T. melt. | 36.5—37 ° C |
| T. bale. | 263 ° C |
| Classification | |
| Reg. CAS number | 120-57-0 |
| PubChem | |
| Reg. EINECS number | |
| Smiles | |
| Inchi | |
| Chebi | |
| ChemSpider | |
Crystals are poorly soluble in water, better in organic solvents, easily distilled with water vapor.
Used for the manufacture of cosmetics and perfumes.
Content
Getting
It can be obtained from plant materials ( vanilla , heliotrope , lilac ), or synthetically from safrole . An interesting method is the oxidation of piperic acid , which in turn is obtained by alkaline hydrolysis of piperine contained in black pepper .
The main production method is the alkaline isomerization of safrole, and then the oxidation of the isosafrol formed by ozone or a chromium mixture (for example, sodium dichromate ) [1] [2] [3] .
There are also methods for producing heliotropin from catechol . Pyrocatechol interacts with glyoxylic acid , 3,4-dioxibenzaldehyde is formed, which is then converted to heliotropin.
According to another method, pyrocatechol is converted to 1,2-methylenedioxybenzene, which then reacts with glyoxylic acid to produce heliotropin.
Legal Status
In Russia, piperonal is included in Table II of Schedule IV of the List of narcotic drugs, psychotropic substances and their precursors to be controlled in the Russian Federation as one of the precursors whose circulation in the Russian Federation is limited and with respect to which general control measures are established (turnover at a concentration of 15% and more prohibited). This is due to the fact that piperonal can be used for the synthesis of 3,4-methylenedioxy derivatives of amphetamine (in particular, MDA ).
Literature
- Knunyants I.L. et al. 1 A-Darzan // Chemical Encyclopedia. - M .: Soviet Encyclopedia, 1988 .-- 623 p. - 100,000 copies.
- Kheifits L.A., Dashunin V.M. Fragrances and other perfumery products. - M .: Chemistry, 1994 .-- 256 p. - 2000 copies. - ISBN 5-7245-0967-9 .
Notes
- ↑ Karl-Georg Fahlbusch, Franz-Josef Hammerschmidt, Johannes Panten, Wilhelm Pickenhagen, Dietmar Schatkowski, Kurt Bauer, Dorothea Garbe and Horst Surburg “Flavors and Fragrances” in Ullmann's Encyclopedia of Industrial Chemistry, Wiley-VCH, 2003, DO 10.1002 / 14356007.a11_141
- ↑ Fatiadi, Alexander; Schaffer, Robert. An Improved Procedure for Synthesis of DL-4-Hydroxy-3-methoxymandelic Acid (DL- "Vanillyl" -mandelic Acid, VMA ) // Journal of Research of the National Bureau of Standards - A. Physics and Chemistry: journal. - 1974. - Vol. 78A , no. 3 . - P. 411-412 . - DOI : 10.6028 / jres.078A.024 .
- ↑ Nwaukwa, Stephen; Keehn, Philip. Oxidative cleavage of α-diols, α-diones, α-hydroxy-ketones and α-hydroxy- and α-keto acids with calcium hypochlorite [Ca (OCl) 2 ] (English) // Tetrahedron Letters : journal. - 1982. - Vol. 23 , no. 31 . - P. 3135-3138 . - DOI : 10.1016 / S0040-4039 (00) 88578-0 .