Piperic acid
Encyclopedia
Piperic acid is a chemical often obtained by the base
-hydrolysis
of the alkaloid
piperine
from black pepper
, followed by acid
ification 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.
, 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.
or ozone
, or a halogen such as bromine
followed by sodium hydroxide causes the oxidative cleavage of the double-bonds, yielding piperonal
via ozonolysis
. Piperonal has many uses in industry and is itself a precursor to a good subsection of other chemicals, including the empathogenic amphetamines MDA
and MDMA, collectively known by the street name ecstasy.
Base (chemistry)
For the term in genetics, see base A base in chemistry is a substance that can accept hydrogen ions or more generally, donate electron pairs. A soluble base is referred to as an alkali if it contains and releases hydroxide ions quantitatively...
-hydrolysis
Hydrolysis
Hydrolysis is a chemical reaction during which molecules of water are split into hydrogen cations and hydroxide anions in the process of a chemical mechanism. It is the type of reaction that is used to break down certain polymers, especially those made by condensation polymerization...
of the alkaloid
Alkaloid
Alkaloids are a group of naturally occurring chemical compounds that contain mostly basic nitrogen atoms. This group also includes some related compounds with neutral and even weakly acidic properties. Also some synthetic compounds of similar structure are attributed to alkaloids...
piperine
Piperine
Piperine is the alkaloid responsible for the pungency of black pepper and long pepper, along with chavicine . It has also been used in some forms of traditional medicine and as an insecticide. Piperine forms monoclinic needles, is slightly soluble in water and more so in alcohol, ether or...
from black pepper
Black pepper
Black pepper is a flowering vine in the family Piperaceae, cultivated for its fruit, which is usually dried and used as a spice and seasoning. The fruit, known as a peppercorn when dried, is approximately in diameter, dark red when fully mature, and, like all drupes, contains a single seed...
, followed by acid
Acid
An acid is a substance which reacts with a base. Commonly, acids can be identified as tasting sour, reacting with metals such as calcium, and bases like sodium carbonate. Aqueous acids have a pH of less than 7, where an acid of lower pH is typically stronger, and turn blue litmus paper red...
ification of the corresponding salt
Salt
In chemistry, salts are ionic compounds that result from the neutralization reaction of an acid and a base. They are composed of cations and anions so that the product is electrically neutral...
. Piperic acid is an intermediate in the synthesis of other compounds such as piperonal
Piperonal
Piperonal, also known as heliotropin, is an aromatic aldehyde that comes as transparent crystals, C8H6O3, and has a floral odor commonly described as being similar to that of vanillin and cherry. It is used as flavoring and in perfume. It can be obtained by oxidation of piperonyl alcohol or the...
, and as-such may be used to produce fragrances, perfumes flavorants and drugs
DRUGS
Destroy Rebuild Until God Shows are an American post-hardcore band formed in 2010. They released their debut self-titled album on February 22, 2011.- Formation :...
as well as other useful compounds.
Preparation
Piperic acid can be prepared from the commercially-available alkaloid piperinePiperine
Piperine is the alkaloid responsible for the pungency of black pepper and long pepper, along with chavicine . It has also been used in some forms of traditional medicine and as an insecticide. Piperine forms monoclinic needles, is slightly soluble in water and more so in alcohol, ether or...
, a cyclic amide
Amide
In chemistry, an amide is an organic compound that contains the functional group consisting of a carbonyl group linked to a nitrogen atom . The term refers both to a class of compounds and a functional group within those compounds. The term amide also refers to deprotonated form of ammonia or an...
containing a piperidine
Piperidine
Piperidine is an organic compound with the molecular formula 5NH. This heterocyclic amine consists of a six-membered ring containing five methylene units and one nitrogen atom...
group, by reacting it with a hydroxide
Hydroxide
Hydroxide is a diatomic anion with chemical formula OH−. It consists of an oxygen and a hydrogen atom held together by a covalent bond, and carrying a negative electric charge. It is an important but usually minor constituent of water. It functions as a base, as a ligand, a nucleophile, and a...
such as potassium hydroxide
Potassium hydroxide
Potassium hydroxide is an inorganic compound with the formula KOH, commonly called caustic potash.Along with sodium hydroxide , this colorless solid is a prototypical strong base. It has many industrial and niche applications. Most applications exploit its reactivity toward acids and its corrosive...
, then acidifying the formed piperate salt with hydrochloric acid
Hydrochloric acid
Hydrochloric acid is a solution of hydrogen chloride in water, that is a highly corrosive, strong mineral acid with many industrial uses. It is found naturally in gastric 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.
Reactions
Reaction of piperic acid with strong oxidizers such as potassium permanganatePotassium permanganate
Potassium permanganate is an inorganic chemical compound with the formula KMnO4. It is a salt consisting of K+ and MnO4− ions. Formerly known as permanganate of potash or Condy's crystals, it is a strong oxidizing agent. It dissolves in water to give intensely purple solutions, the...
or ozone
Ozone
Ozone , or trioxygen, is a triatomic molecule, consisting of three oxygen atoms. It is an allotrope of oxygen that is much less stable than the diatomic allotrope...
, or a halogen such as bromine
Bromine
Bromine ") is a chemical element with the symbol Br, an atomic number of 35, and an atomic mass of 79.904. It is in the halogen element group. The element was isolated independently by two chemists, Carl Jacob Löwig and Antoine Jerome Balard, in 1825–1826...
followed by sodium hydroxide causes the oxidative cleavage of the double-bonds, yielding piperonal
Piperonal
Piperonal, also known as heliotropin, is an aromatic aldehyde that comes as transparent crystals, C8H6O3, and has a floral odor commonly described as being similar to that of vanillin and cherry. It is used as flavoring and in perfume. It can be obtained by oxidation of piperonyl alcohol or the...
via ozonolysis
Ozonolysis
Ozonolysis is the cleavage of an alkene or alkyne with ozone to form organic compounds in which the multiple carbon–carbon bond has been replaced by a double bond to oxygen...
. Piperonal has many uses in industry and is itself a precursor to a good subsection of other chemicals, including the empathogenic amphetamines MDA
3,4-Methylenedioxyamphetamine
3,4-Methylenedioxyamphetamine , also known as tenamfetamine , is a psychedelic and entactogenic drug of the phenethylamine and amphetamine chemical classes...
and MDMA, collectively known by the street name ecstasy.
See also
- PiperonalPiperonalPiperonal, also known as heliotropin, is an aromatic aldehyde that comes as transparent crystals, C8H6O3, and has a floral odor commonly described as being similar to that of vanillin and cherry. It is used as flavoring and in perfume. It can be obtained by oxidation of piperonyl alcohol or the...
- PiperinePiperinePiperine is the alkaloid responsible for the pungency of black pepper and long pepper, along with chavicine . It has also been used in some forms of traditional medicine and as an insecticide. Piperine forms monoclinic needles, is slightly soluble in water and more so in alcohol, ether or...
- SafroleSafroleSafrole, also known as shikimol, is a phenylpropene. It is a colorless or slightly yellow oily liquid. It is typically extracted from the root-bark or the fruit of sassafras plants in the form of sassafras oil , or synthesized from other related methylenedioxy...
- IsosafroleIsosafroleIsosafrole is a phenylpropene, a type of aromatic organic chemical with a smell similar to anise or licorice. It is found in small amounts in various essential oils, but is most commonly obtained by isomerizing the plant oil safrole....
- SesamolSesamolSesamol is a natural organic compound which is a component of sesame oil. It is a white crystalline solid that is a derivative of phenol. It is sparingly soluble in water, but miscible with most oils...
- Piperonyl butoxidePiperonyl butoxidePiperonyl butoxide is an organic compound used as pesticide synergist, especially for pyrethroids and rotenone. It does not by itself have pesticidal properties. However, when added to insecticide mixtures, typically pyrethrin, pyrethroid, and carbamate insecticides, their potency is increased...
- Cinnamic acidCinnamic acidCinnamic acid is a white crystalline organic acid, which is slightly soluble in water.It is obtained from oil of cinnamon, or from balsams such as storax. It is also found in shea butter and is the best indication of its environmental history and post-extraction conditions...