Sinapaldehyde is an

organic compound In chemistry, organic compounds are generally any chemical compounds that contain carbon-hydrogen or carbon-carbon bonds. Due to carbon's ability to catenate (form chains with other carbon atoms), millions of organic compounds are known. The ...

with the formula HO(CH₃O)₂C₆H₂CH=CHCHO. It is a derivative of

cinnamaldehyde Cinnamaldehyde is an organic compound with the formula(C9H8O) C6H5CH=CHCHO. Occurring naturally as predominantly the ''trans'' (''E'') isomer, it gives cinnamon its flavor and odor. It is a phenylpropanoid that is naturally synthesized by the shik ...

, featuring one

hydroxy group In chemistry, a hydroxy or hydroxyl group is a functional group with the chemical formula and composed of one oxygen atom covalently bonded to one hydrogen atom. In organic chemistry, alcohols and carboxylic acids contain one or more hydroxy ...

and two

methoxy group In organic chemistry, a methoxy group is the functional group consisting of a methyl group bound to oxygen. This alkoxy group has the formula . On a benzene ring, the Hammett equation classifies a methoxy substituent at the ''para'' position as ...

s as

substituent A substituent is one or a group of atoms that replaces (one or more) atoms, thereby becoming a moiety in the resultant (new) molecule. (In organic chemistry and biochemistry, the terms ''substituent'' and ''functional group'', as well as ''side ...

s. It is an intermediate in the formation of

sinapyl alcohol 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 ...

, a lignol that is a major precursor to

lignin 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 ...

Biosynthetic role

In sweetgum (''

Liquidambar styraciflua American sweetgum (''Liquidambar styraciflua''), also known as American storax, hazel pine, bilsted, redgum, satin-walnut, star-leaved gum, alligatorwood, or simply sweetgum, is a deciduous tree in the genus ''Liquidambar'' native to warm temper ...

''), sinapaldehyde arises in two steps from

coniferyl aldehyde 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. Biosynthetic role In sweetgum (''Liquidamba ...

beginning with

hydroxylation In chemistry, hydroxylation can refer to: *(i) most commonly, hydroxylation describes a chemical process that introduces a hydroxyl group () into an organic compound. *(ii) the ''degree of hydroxylation'' refers to the number of OH groups in a ...

mediated by coniferyl aldehyde 5-hydroxylase. The diphenol is then methylated at the 5-OH by the action of caffeate ''O''-methyltransferase. Sinapaldehyde is reduced to the alcohol by the action of

dehydrogenase A dehydrogenase is an enzyme belonging to the group of oxidoreductases that oxidizes a substrate by reducing an electron acceptor, usually NAD+/NADP+ or a flavin coenzyme such as FAD or FMN. Like all catalysts, they catalyze reverse as well as f ...

enzymes. In ''

Arabidopsis thaliana ''Arabidopsis thaliana'', the thale cress, mouse-ear cress or arabidopsis, is a small flowering plant native to Eurasia and Africa. ''A. thaliana'' is considered a weed; it is found along the shoulders of roads and in disturbed land. A winter a ...

'', the enzyme

dihydroflavonol 4-reductase In enzymology, a dihydrokaempferol 4-reductase () is an enzyme that catalyzes the chemical reaction :cis-3,4-leucopelargonidin + NADP+ \rightleftharpoons (+)-dihydrokaempferol + NADPH + H+ Thus, the two substrates of this enzyme are cis-3,4-l ...

uses NADP⁺ to reduce sinapaldehyde to sinapyl alcohol. It is found in ''

Senra incana ''Senra incana'' is a flowering plant species in the genus '' Senra''. The plant produces the phenolic compounds coniferaldehyde, scopoletin, sinapaldehyde and syringaldehyde Syringaldehyde is an organic compound that occurs in trace amounts wi ...

'' (Hibisceae). It is a low molecular weight

phenol Phenol (also called carbolic acid) is an aromatic organic compound with the molecular formula . It is a white crystalline solid that is volatile. The molecule consists of a phenyl group () bonded to a hydroxy group (). Mildly acidic, it req ...

that is susceptible to extraction from

cork stopper A stopper or cork is a cylindrical or conical closure used to seal a container, such as a bottle, tube or barrel. Unlike a lid or bottle cap, which encloses a container from the outside without displacing the inner volume, a bung is partially ...

s into wine.Polyphenolic Composition of ''Quercus suber'' Cork from Different Spanish Provenances. Elvira Conde, Estrella Cadahía, María Concepción García-Vallejo and Brígida Fernández de Simón, J. Agric. Food Chem., 1998, volume 46, pp 3166–3171

References

Natural phenols Aldehydes O-methylated phenylpropanoids {{Phenol-stub

Biosynthetic role

See also

References