Paracoumaryl alcohol

Last updated
Paracoumaryl alcohol
P-Coumaryl alcohol.svg
Names
Preferred IUPAC name
4-[(1E)-3-Hydroxyprop-1-en-1-yl]phenol
Other names
p-coumaryl alcohol, 4-coumaryl alcohol, 4-hydroxycinnamyl alcohol, 4-(3-hydroxy-1-propenyl)phenol
Identifiers
3D model (JSmol)
ChEBI
ChEMBL
ChemSpider
KEGG
PubChem CID
UNII
  • InChI=1S/C9H10O2/c10-7-1-2-8-3-5-9(11)6-4-8/h1-6,10-11H,7H2/b2-1+ X mark.svgN
    Key: PTNLHDGQWUGONS-OWOJBTEDSA-N X mark.svgN
  • InChI=1/C9H10O2/c10-7-1-2-8-3-5-9(11)6-4-8/h1-6,10-11H,7H2/b2-1+
    Key: PTNLHDGQWUGONS-OWOJBTEDBL
  • OC/C=C/c1ccc(O)cc1
Properties
C9H10O2
Molar mass 150.1745
AppearanceWhite solid
Melting point 114–116 °C (237–241 °F; 387–389 K)
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 ?)

Paracoumaryl alcohol is a phytochemical, one of the monolignols. It is a white solid. p-Coumaryl alcohol is a major precursor to lignin or lignans. [1]

Contents

Biosynthesis and occurrence

It is synthesized via the phenylpropanoid biochemical pathway.

Esters of p-coumaryl alcohol and fatty acids are the basis of epicuticular waxes covering the surfaces of apples.

p-Coumaryl alcohol is an intermediate in biosynthesis of chavicol, stilbenoids, and coumarin.

Related Research Articles

<span class="mw-page-title-main">Alcoholism</span> Problematic excessive alcohol consumption

Alcoholism is the continued drinking of alcohol despite negative results. Problematic use of alcohol has been mentioned in the earliest historical records, such as in ancient Egypt and in the Bible, and remains widespread; the World Health Organization (WHO) estimated there were 283 million people with alcohol use disorders worldwide as of 2016. The term alcoholism was first coined in 1852, but alcoholism and alcoholic are stigmatizing and discourage seeking treatment, so clinical diagnostic terms such as alcohol use disorder or alcohol dependence are used instead.

<span class="mw-page-title-main">Ethanol</span> Organic compound (CH₃CH₂OH)

Ethanol is an organic compound with the chemical formula CH3CH2OH. It is an alcohol, with its formula also written as C2H5OH, C2H6O or EtOH, where Et stands for ethyl. Ethanol is a volatile, flammable, colorless liquid with a characteristic wine-like odor and pungent taste. It is a psychoactive recreational drug, and the active ingredient in alcoholic drinks.

<span class="mw-page-title-main">Lignin</span> Structural phenolic polymer in plant cell walls

Lignin is a class of complex organic polymers that form key structural materials in the support tissues of most plants. Lignins are particularly important in the formation of cell walls, especially in wood and bark, because they lend rigidity and do not rot easily. Chemically, lignins are polymers made by cross-linking phenolic precursors.

<span class="mw-page-title-main">Cross-link</span> Bonds linking one polymer chain to another

In chemistry and biology a cross-link is a bond or a short sequence of bonds that links one polymer chain to another. These links may take the form of covalent bonds or ionic bonds and the polymers can be either synthetic polymers or natural polymers.

<span class="mw-page-title-main">Liquor</span> Alcoholic drink produced by distillation

Liquor is an alcoholic drink produced by the distillation of grains, fruits, vegetables, or sugar that have already gone through alcoholic fermentation. Other terms for liquor include: spirit, distilled beverage, spirituous liquor or hard liquor. The distillation process concentrates the liquid to increase its alcohol by volume. As liquors contain significantly more alcohol (ethanol) than other alcoholic drinks, they are considered "harder." In North America, the term hard liquor is sometimes used to distinguish distilled alcoholic drinks from non-distilled ones, whereas the term spirits is more commonly used in the UK. Some examples of liquors include vodka, rum, gin, and tequila. Liquors are often aged in barrels, such as for the production of brandy and whiskey, or are infused with flavorings to form flavored liquors, such as absinthe.

Guaiacol is an organic compound with the formula C6H4(OH)(OCH3). It is a phenolic compound containing a methoxy functional group. Guaiacol appears as a viscous colorless oil, although aged or impure samples are often yellowish. It occurs widely in nature and is a common product of the pyrolysis of wood.

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

Coniferyl alcohol is an organic compound with the formula HO(CH3O)C6H3CH=CHCH2OH. A colourless or white solid, it is one of the monolignols, produced via the phenylpropanoid biochemical pathway. When copolymerized with related aromatic compounds, coniferyl alcohol forms lignin or lignans. Coniferin is a glucoside of coniferyl alcohol. Coniferyl alcohol is an intermediate in biosynthesis of eugenol and of stilbenoids and coumarin. Gum benzoin contains significant amount of coniferyl alcohol and its esters. It is found in both gymnosperm and angiosperm plants. Sinapyl alcohol and paracoumaryl alcohol, the other two lignin monomers, are found in angiosperm plants and grasses.

<span class="mw-page-title-main">Dirigent protein</span>

Dirigent proteins are members of a class of proteins which dictate the stereochemistry of a compound synthesized by other enzymes. The first dirigent protein was discovered in Forsythia intermedia. This protein has been found to direct the stereoselective biosynthesis of (+)-pinoresinol from coniferyl alcohol monomers:

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

The phenylpropanoids are a diverse family of organic compounds that are synthesized by plants from the amino acids phenylalanine and tyrosine. Their name is derived from the six-carbon, aromatic phenyl group and the three-carbon propene tail of coumaric acid, which is the central intermediate in phenylpropanoid biosynthesis. From 4-coumaroyl-CoA emanates the biosynthesis of myriad natural products including lignols, flavonoids, isoflavonoids, coumarins, aurones, stilbenes, catechin, and phenylpropanoids. The coumaroyl component is produced from cinnamic acid.

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

Syringol is the organic compound with the formula HO(CH3O)2C6H3. The molecule is a phenol, with methoxy groups in the flanking (2 and 6) positions. It is the symmetrically dimethylated derivative of pyrogallol. It is a colorless solid, although typical samples are brown owing to air-oxidized impurities. Together with guaiacol, syringol and its derivatives are produced by the pyrolysis of lignin. Specifically, syringol is derived from the thermal decomposition of the sinapyl alcohol component. As such, syringol is an important component of wood smoke.

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

Sinapyl alcohol is an organic compound structurally related to cinnamic acid. It is biosynthetized via the phenylpropanoid biochemical pathway, its immediate precursor being sinapaldehyde. This phytochemical is one of the monolignols, which are precursor to lignin or lignans. It is also a biosynthetic precursor to various stilbenoids and coumarins.

In enzymology, a dihydrokaempferol 4-reductase (EC 1.1.1.219) is an enzyme that catalyzes the chemical reaction

<span class="mw-page-title-main">Cinnamoyl-CoA reductase</span>

Cinnamoyl-CoA reductase (EC 1.2.1.44), systematically named cinnamaldehyde:NADP+ oxidoreductase (CoA-cinnamoylating) but commonly referred to by the acronym CCR, is an enzyme that catalyzes the reduction of a substituted cinnamoyl-CoA to its corresponding cinnamaldehyde, utilizing NADPH and H+ and releasing free CoA and NADP+ in the process. Common biologically relevant cinnamoyl-CoA substrates for CCR include p-coumaroyl-CoA and feruloyl-CoA, which are converted into p-coumaraldehyde and coniferaldehyde, respectively, though most CCRs show activity toward a variety of other substituted cinnamoyl-CoA's as well. Catalyzing the first committed step in monolignol biosynthesis, this enzyme plays a critical role in lignin formation, a process important in plants both for structural development and defense response.

<span class="mw-page-title-main">Alcoholic beverage</span> Drink with a substantial ethanol amount

An alcoholic beverage is a drink that contains ethanol, a type of alcohol and is produced by fermentation of grains, fruits, or other sources of sugar. The consumption of alcoholic drinks, often referred to as "drinking", plays an important social role in many cultures. Alcoholic drinks are typically divided into three classes—beers, wines, and spirits—and typically their alcohol content is between 3% and 50%.

Isopropyl alcohol is a colorless, flammable organic compound with a pungent alcoholic odor. As an isopropyl group linked to a hydroxyl group it is the simplest example of a secondary alcohol, where the alcohol carbon atom is attached to two other carbon atoms. It is a structural isomer of propan-1-ol and ethyl methyl ether. They all have the formula C3H8O.

<span class="mw-page-title-main">Prohibition in the United States</span> 1920-1933 alcohol ban in United States

The Prohibition era was a period in the United States from 1920 to 1933 during which a nationwide constitutional law prohibiting the production, importation, transportation, and sale of alcoholic beverages was enacted. The alcohol industry was curtailed by a succession of state legislatures, and finally ended nationwide under the Eighteenth Amendment to the United States Constitution, ratified on January 16, 1919. Prohibition ended with the ratification of the Twenty-first Amendment, which repealed the Eighteenth Amendment on December 5, 1933.

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

Sinapaldehyde is an organic compound with the formula HO(CH3O)2C6H2CH=CHCHO. It is a derivative of cinnamaldehyde, featuring one hydroxy group and two methoxy groups as substituents. It is an intermediate in the formation of sinapyl alcohol, a lignol that is a major precursor to lignin.

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

Coniferyl aldehyde is an organic compound with the formula HO(CH3O)C6H3CH=CHCHO. It is a derivative of cinnamaldehyde, featuring 4-hydroxy and 3-methoxy substituents. It is a major precursor to lignin.

Eugenol synthase (EC 1.1.1.318, LtCES1, EGS1, EGS2) is an enzyme with systematic name eugenol:NADP+ oxidoreductase (coniferyl ester reducing). This enzyme catalyses the following chemical reaction: eugenol + a carboxylate + NADP+ a coniferyl ester + NADPH + H+

<span class="mw-page-title-main">Alcohol (drug)</span> Active ingredient in alcoholic beverages

Alcohol, sometimes referred to by the chemical name ethanol, is a depressant drug that is the active ingredient in fermented drinks such as beer, wine, and distilled spirits. It is one of the oldest and most commonly consumed recreational drugs, causing the characteristic effects of alcohol intoxication ("drunkenness"). Among other effects, alcohol produces happiness and euphoria, decreased anxiety, increased sociability, sedation, impairment of cognitive, memory, motor, and sensory function, and generalized depression of central nervous system (CNS) function.

References

  1. Withers, Saunia; Lu, Fachuang; Kim, Hoon; Zhu, Yimin; Ralph, John; Wilkerson, Curtis G. (2012). "Identification of Grass-specific Enzyme That Acylates Monolignols with p-Coumarate". Journal of Biological Chemistry. 287 (11): 8347–8355. doi: 10.1074/jbc.M111.284497 . PMC   3318722 . PMID   22267741. S2CID   24998478.