IRONE

Описание

α-Irone has a characteristic orris and violet-like odor. The commercially prepared product corresponds generally to the α-isomer.

Химические свойства

Yellowish liquid; Soluble in alcohol. A mixture of three isomers (α-, βand γ-irone).

Вхождение

Reported found in orris root, raspberry and flowers of Pittosporum sp

Использование

Perfumery, violet odor. The α isomer is also used as a flavoring agent.

Подготовка

By intramolecular thermal H-ene reaction of an allysilane.

Определение

ChEBI: A methyl ketone that is alpha-ionone in which a hydrogen at position 5 of the cyclohex-2-en-1-yl ring is substituted by a methyl group.

Общее описание

Irone is a bioactive compound that is produced by an endophytic fungus in the rhizomes of Iris germanica.

Синтез

Alpha-n-Methy lionone is synthesized by condensation of Methylethyl ketone with Citral, and cyclization of the resulting Pseudomethylionone. Cyclization may be carried out with Boron trifluoride or other agent.

Методы очистки

If large amounts are available, then fractionate through a Podbielniak column (p 10) or an efficient spinning band column, but small amounts are distilled using a Kügelrohr apparatus. The 4-phenylsemicarbazone has m 174-175o (165-165.5o). [IR: Seidel & Ruzicka Helv Chim Acta 35 1826 1952, Naves Helv Chim Acta 31 1280 1948, Lecomte & Naves J Chim Phys 53 462 1956, Beilstein 7 IV 378.]