Perilla ketone

Last updated
Perilla ketone
Perilla ketone.png
Names
Preferred IUPAC name
1-(Furan-3-yl)-4-methylpentan-1-one
Other names
beta-Furyl isoamyl ketone
Identifiers
3D model (JSmol)
ChemSpider
PubChem CID
UNII
  • InChI=LVHLZMUFIYAEQB-UHFFFAOYSA-N
  • CC(C)CCC(C1=COC=C1)=O
Properties
C10H14O2
Molar mass 166.217
AppearanceLiquid
Density 0.9920 g/cm3
Melting point <25 °C
Boiling point 196 °C (385 °F; 469 K)
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
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Perilla ketone is a natural terpenoid that consists of a furan ring with a six-carbon side chain 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. [1] Perilla ketone is present in the leaves and seeds of purple mint ( Perilla frutescens), which is toxic to some animals. [2] When cattle and horses consume purple mint when grazing in fields in which it grows, the perilla ketone causes pulmonary edema leading to a condition sometimes called perilla mint toxicosis. [2]

Contents

Synthesis

Perilla ketone was synthesized in 1957 by Matsuura from 3-furoyl chloride and an organocadmium compound similar to the Gilman reagent made from an isoamyl Grignard reagent and cadmium chloride. [3] Perilla ketone (3-Furyl isoamyl ketone) has been prepared in 74% yield via the Stille reaction from a 3-furyl-organotin compound and isocaproyl chloride in tetrahydrofuran solvent. [4]

See also

Related Research Articles

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<span class="mw-page-title-main">Oxime</span> Organic compounds of the form >C=N–OH

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<span class="mw-page-title-main">Shiso</span> Variety of plant in the mint family

Perilla frutescensvar.crispa, also known by its Japanese name shiso, is a cultigen of Perilla frutescens, a herb in the mint family Lamiaceae. It is native to the mountainous regions of China and India, but is now found worldwide. The plant occurs in several forms, as defined by the characteristics of their leaves, including red, green, bicolor, and ruffled. Shiso is perennial and may be cultivated as an annual in temperate climates. Different parts of the plant are used in East Asian and Southeast Asian cuisine.

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<span class="mw-page-title-main">Methyllithium</span> Chemical compound

Methyllithium is the simplest organolithium reagent with the empirical formula CH3Li. This s-block organometallic compound adopts an oligomeric structure both in solution and in the solid state. This highly reactive compound, invariably used in solution with an ether as the solvent, is a reagent in organic synthesis as well as organometallic chemistry. Operations involving methyllithium require anhydrous conditions, because the compound is highly reactive toward water. Oxygen and carbon dioxide are also incompatible with MeLi. Methyllithium is usually not prepared, but purchased as a solution in various ethers.

<span class="mw-page-title-main">Organozinc compound</span>

Organozinc compounds in organic chemistry contain carbon (C) to zinc (Zn) chemical bonds. Organozinc chemistry is the science of organozinc compounds describing their physical properties, synthesis and reactions.

<span class="mw-page-title-main">Organocadmium compound</span>

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 mercury and their corresponding chemistries have much in common. The synthetic utility of organocadmium compounds is limited.

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<i>Perilla frutescens</i> Species of flowering plant

Perilla frutescens, commonly called deulkkae, perilla or Korean perilla, is a species of Perilla in the mint family Lamiaceae. It is an annual plant native to Southeast Asia and Indian highlands, and is traditionally grown in the Korean peninsula, southern China, Japan and India as a crop.

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<span class="mw-page-title-main">Tetramethyltin</span> Chemical compound

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Perilla may refer to any of the following subjects:

<span class="mw-page-title-main">Rosefuran</span> Chemical compound

Rosefuran (3-methyl-2-prenylfuran) is a liquid boiling at 103-104 °C, with a density of 0.9089 g/cm3, less than that of water. It is an aroma chemical which is a minor constituent of the aroma of the rose. Rosefuran is a 2,3-disubstituted furan. It has an odor threshold of 200 ppb and constitutes 0.16% of Bulgarian rose oil. Rosefuran has been established as a female sex pheromone of an acarid mite, Caloglyphus sp. Concentrations of less than 100 ng of synthetic rosefuran caused sexual excitation in males of the species.

<span class="mw-page-title-main">2-Acetylfuran</span> Chemical compound

2-Acetylfuran is a low melting solid or high boiling liquid, depending on temperature. The solid melts at 30 °C and has a density of 1.0975 g/ml at 20 °C, while the normal boiling point of the liquid is 168–169 °C. 2-Acetylfuran is a useful intermediate in the synthesis of fine chemicals and pharmaceuticals, and is used in the production of the generic cephalophosphorin antibiotic cefuroxime.

<span class="mw-page-title-main">Perillene</span> Chemical compound

Perillene is a natural monoterpene that consists of a furan ring with a six-carbon homoprenyl side chain. Perillene is a component of the essential oil obtained by extraction of the leaves of Perilla frutescens. Perillene has also been obtained by steam distillation of the leaves of Perilla frutescens. Perillene has been found to elicit distinct electrophysiological responses in the antennae of the apple blossom weevil. It has been suggested that perillene is one several terpene hydrocarbons in the emanation bouquet of apple tree buds which may be used by adult weevils as chemical cues to discrimination during host-searching behavior.

<span class="mw-page-title-main">Ynone</span> Organic compounds of the form RC≡CC(=O)R’

In organic chemistry, an ynone is an organic compound containing a ketone functional group and a C≡C triple bond. Many ynones are α,β-ynones, where the carbonyl and alkyne groups are conjugated. Capillin is a naturally occurring example. Some ynones are not conjugated.

References

  1. Sebe, Yeigai (1943). "Supplemental experiments on perilla ketone". Nippon Kagaku Kaishi (in Japanese). 64 (8): 1130–6. doi: 10.1246/nikkashi1921.64.1130 . Open Access logo PLoS transparent.svg
  2. 1 2 Perilla: Botany, Uses and Genetic Resources
  3. Matsuura, Teruo (1957). "Natural furan derivatives. I. The synthesis of perilla ketone". Bulletin of the Chemical Society of Japan . 30: 430–1. doi: 10.1246/bcsj.30.430 . Open Access logo PLoS transparent.svg
  4. Farina, Vittorio; Krishnamurthy, Venkat; Scott, William J. (1997). "The Stille reaction". Organic Reactions . 50: 1–652. doi:10.1002/0471264180.or050.01. ISBN   0471264180.