Perilla ketone is a natural
terpenoid
The terpenoids, also known as isoprenoids, are a class of naturally occurring organic chemicals derived from the 5-carbon compound isoprene and its derivatives called terpenes, diterpenes, etc. While sometimes used interchangeably with "terpenes" ...
that consists of a
furan ring with a six-carbon
side chain
In organic chemistry and biochemistry, a side chain is a chemical group that is attached to a core part of the molecule called the "main chain" or backbone. The side chain is a hydrocarbon branching element of a molecule that is attached to a ...
containing a
ketone functional group. It is a colorless oil that is sensitive to oxygen, becoming colored upon standing. The ketone was identified in 1943 by Sebe as the main component of the essential oil of Perilla frutescens. Perilla ketone is present in the leaves and seeds of purple mint (''
Perilla
''Perilla'' is a genus consisting of one major Asiatic crop species ''Perilla frutescens'' and a few wild species in nature belonging to the mint family, Lamiaceae. The genus encompasses several distinct varieties of Asian herb, seed, and veget ...
frutescens''), which is toxic to some animals.
[Perilla: Botany, Uses and Genetic Resources]
/ref> When cattle and horses consume purple mint when grazing in fields in which it grows, the perilla ketone causes pulmonary edema
Pulmonary edema, also known as pulmonary congestion, is excessive liquid accumulation in the tissue and air spaces (usually alveoli) of the lungs. It leads to impaired gas exchange and may cause hypoxemia and respiratory failure. It is due t ...
leading to a condition sometimes called perilla mint toxicosis.[
]
Synthesis
Perilla ketone was synthesized in 1957 by Matsuura from 3-furoyl chloride and an organocadmium compound
An organocadmium compound is an organometallic compound containing a carbon to cadmium chemical bond. Organocadmium chemistry describes physical properties, synthesis, reactions and use of these compounds. Cadmium shares group 12 with zinc and me ...
similar to the Gilman reagent
A Gilman reagent is a lithium and copper ( diorganocopper) reagent compound, R2CuLi, where R is an alkyl or aryl. These reagents are useful because, unlike related Grignard reagents and organolithium reagents, they react with organic halides to ...
made from an isoamyl Grignard reagent and cadmium chloride. Perilla ketone (3-Furyl isoamyl ketone) has been prepared in 74% yield via the Stille reaction
The Stille reaction is a chemical reaction widely used in organic synthesis. The reaction involves the coupling of two organic groups, one of which is carried as an organotin compound (also known as organostannanes). A variety of organic electroph ...
from a 3-furyl-organotin compound and isocaproyl chloride in tetrahydrofuran
Tetrahydrofuran (THF), or oxolane, is an organic compound with the formula (CH2)4O. The compound is classified as heterocyclic compound, specifically a cyclic ether. It is a colorless, water- miscible organic liquid with low viscosity. It is ...
solvent.
See also
* Perillene
References
{{Reflist
3-Furyl compounds
Ketones
Monoterpenes