Piperic acid

Last updated
Piperic acid
Piperinsaure.svg
Names
IUPAC name
(2E,4E)-5-(3,4-Methylenedioxyphenyl)-2,4-pentadienoic acid
Identifiers
3D model (JSmol)
ChEBI
ChEMBL
ChemSpider
EC Number
  • 226-118-4
MeSH C017637
PubChem CID
UNII
Properties
C12H10O4
Molar mass 218.208 g·mol−1
Boiling point decomposes
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
X mark.svgN  verify  (what is  Yes check.svgYX mark.svgN ?)
Infobox references

Piperic acid is a chemical often obtained by the base-hydrolysis of the alkaloid piperine [1] from black pepper, [2] followed by acidification of the corresponding salt. Piperic acid is an intermediate in the synthesis of other compounds such as piperonal, and as-such may be used to produce fragrances, perfumes flavorants and drugs as well as other useful compounds.

Contents

Preparation

Piperic acid can be prepared from the commercially-available alkaloid piperine, a cyclic amide containing a piperidine group, by reacting it with a hydroxide such as potassium hydroxide, then acidifying the formed piperate salt with hydrochloric acid or another acid. The toxic compound piperidine is given off during the base-hydrolysis of piperine and as-such, safety precautions should be taken.

Piperic acid from piperine.jpg

Reactions

Reaction of piperic acid with strong oxidizers such as potassium permanganate or ozone, or a halogen such as bromine followed by sodium hydroxide causes oxidative cleavage of the double-bonds, yielding piperonal and piperonylic acid. [3] Piperonal has many uses in industry and is itself a precursor to a good subsection of other chemicals. On reduction with sodium amalgam piperic acid forms α- and β-dihydropiperic acid, C12H12O4, and the latter can take up two further atoms of hydrogen to produce tetrahydropiperic acid.

See also

Related Research Articles

Hydroxide Family of the hydroxide salts

Hydroxide is a diatomic anion with chemical formula OH. It consists of an oxygen and hydrogen atom held together by a covalent bond, and carries a negative electric charge. It is an important but usually minor constituent of water. It functions as a base, a ligand, a nucleophile, and a catalyst. The hydroxide ion forms salts, some of which dissociate in aqueous solution, liberating solvated hydroxide ions. Sodium hydroxide is a multi-million-ton per annum commodity chemical. A hydroxide attached to a strongly electropositive center may itself ionize, liberating a hydrogen cation (H+), making the parent compound an acid.

Hydrolysis is any chemical reaction in which a molecule of water ruptures one or more chemical bonds. The term is used broadly for substitution, elimination, and fragmentation reactions in which water is the nucleophile.

Piperidine chemical compound

Piperidine is an organic compound with the molecular formula (CH2)5NH. This heterocyclic amine consists of a six-membered ring containing five methylene bridges (–CH2–) and one amine bridge (–NH–). It is a colorless liquid with an odor described as objectionable, and typical of amines. The name comes from the genus name Piper, which is the Latin word for pepper. Although piperidine is a common organic compound, it is best known as a representative structure element within many pharmaceuticals and alkaloids, such as natural-occurring solenopsins.

Salt (chemistry) Ionic compound consisting of cations and anions

In chemistry, a salt is a chemical compound consisting of an ionic assembly of cations and anions. Salts are composed of related numbers of cations and anions so that the product is electrically neutral. These component ions can be inorganic, such as chloride (Cl), or organic, such as acetate ; and can be monatomic, such as fluoride (F) or polyatomic, such as sulfate.

Sodium cyanide chemical compound

Sodium cyanide is an inorganic compound with the formula NaCN. It is a white, water-soluble solid. Cyanide has a high affinity for metals, which leads to the high toxicity of this salt. Its main application, in gold mining, also exploits its high reactivity toward metals. It is a moderately strong base. When treated with acid, it forms the toxic gas hydrogen cyanide:

Sodium hydroxide Chemical compound with formula NaOH

Sodium hydroxide, also known as lye and caustic soda, is an inorganic compound with the formula NaOH. It is a white solid ionic compound consisting of sodium cations Na+
and hydroxide anions OH
.

Base (chemistry) substance that can react with an acid, accepting hydrogen ions (protons) or more generally, donating a pair of valence electrons

In chemistry, bases are substances that, in aqueous solution, release hydroxide (OH) ions, are slippery to the touch, can taste bitter if an alkali, change the color of indicators (e.g., turn red litmus paper blue), react with acids to form salts, promote certain chemical reactions (base catalysis), accept protons from any proton donor or contain completely or partially displaceable OH ions. Examples of bases are the hydroxides of the alkali metals and the alkaline earth metals (NaOH, Ca(OH)2, etc.—see alkali hydroxide and alkaline earth hydroxide).

Potassium chloride

Potassium chloride is a metal halide salt composed of potassium and chlorine. It is odorless and has a white or colorless vitreous crystal appearance. The solid dissolves readily in water, and its solutions have a salt-like taste. KCl is used as a fertilizer, in medicine, in scientific applications, and in food processing, where it may be known as E number additive E508.

Potassium ferricyanide Chemical compound

Potassium ferricyanide is the chemical compound with the formula K3[Fe(CN)6]. This bright red salt contains the octahedrally coordinated [Fe(CN)6]3− ion. It is soluble in water and its solution shows some green-yellow fluorescence. It was discovered in 1822 by Leopold Gmelin, and was initially used in the production of ultramarine dyes.

Potassium hydroxide chemical compound

Potassium hydroxide is an inorganic compound with the formula KOH, and is commonly called caustic potash.

Corrosive substance Strong alkaline chemicals that destroy soft body tissues resulting in a deep, penetrating type of burn, in contrast to corrosives, that result in a more superficial type of damage via chemical means or inflammation. Caustics are usually hydroxides.

A corrosive substance is one that will damage or destroy other substances with which it comes into contact by means of a chemical reaction.

Diethyl malonate chemical compound

Diethyl malonate, also known as DEM, is the diethyl ester of malonic acid. It occurs naturally in grapes and strawberries as a colourless liquid with an apple-like odour, and is used in perfumes. It is also used to synthesize other compounds such as barbiturates, artificial flavourings, vitamin B1, and vitamin B6.

Potassium cyanide inorganic compound

Potassium cyanide is a compound with the formula KCN. This colorless crystalline salt, similar in appearance to sugar, is highly soluble in water. Most KCN is used in gold mining, organic synthesis, and electroplating. Smaller applications include jewelry for chemical gilding and buffing.

Piperine chemical compound

Piperine, along with its isomer chavicine, is the alkaloid responsible for the pungency of black pepper and long pepper. It has been used in some forms of traditional medicine.

The Cannizzaro reaction, named after its discoverer Stanislao Cannizzaro, is a chemical reaction that involves the base-induced disproportionation of two molecules of a non-enolizable aldehyde to give a primary alcohol and a carboxylic acid.

Potassium nitrite chemical compound

Potassium nitrite (distinct from potassium nitrate) is the inorganic compound with the chemical formula KNO2. It is an ionic salt of potassium ions K+ and nitrite ions NO2, which forms a white or slightly yellow, hygroscopic crystalline powder that is soluble in water.

Sodium bisulfate sodium bisulfate

Sodium bisulfate, also known as sodium hydrogen sulfate, is the sodium salt of the bisulfate anion, with the molecular formula NaHSO4. Sodium bisulfate is an acid salt formed by partial neutralization of sulfuric acid by an equivalent of sodium base, typically in the form of either sodium hydroxide (lye) or sodium chloride (table salt). It is a dry granular product that can be safely shipped and stored. The anhydrous form is hygroscopic. Solutions of sodium bisulfate are acidic, with a 1M solution having a pH of around 1.

Antimony pentoxide chemical compound

Antimony pentoxide (molecular formula: Sb2O5) is a chemical compound of antimony and oxygen. It always occurs in hydrated form, Sb2O5·nH2O. It contains antimony in the +5 oxidation state.

The total synthesis of quinine, a naturally-occurring antimalarial drug, was developed over a 150-year period. The development of synthetic quinine is considered a milestone in organic chemistry although it has never been produced industrially as a substitute for natural occurring quinine. The subject has also been attended with some controversy: Gilbert Stork published the first stereoselective total synthesis of quinine in 2001, meanwhile shedding doubt on the earlier claim by Robert Burns Woodward and William Doering in 1944, claiming that the final steps required to convert their last synthetic intermediate, quinotoxine, into quinine would not have worked had Woodward and Doering attempted to perform the experiment. A 2001 editorial published in Chemical & Engineering News sided with Stork, but the controversy was eventually laid to rest once and for all when Williams and coworkers successfully repeated Woodward's proposed conversion of quinotoxine to quinine in 2007.

Potassium hypochlorite is the potassium salt of hypochlorous acid. It is used in variable concentrations, often diluted in water solution. It has a light grey color and a strong chlorine smell. It can be used as a disinfectant.

References

  1. Paul M. Dewick. (2009). Medicinal natural products : a biosynthetic approach. Chichester: A John Wiley & Sons. p. 327. ISBN   978-0-470-74167-2.
  2. E. Gildemeister. The Volatile Oils. Volume 1.
  3. US 5095128,"Preparation process for piperonal"