Coniferyl alcohol 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. T ...

with the formula HO(CH₃O)C₆H₃CH=CHCH₂OH. A colourless or white solid, it is one of the

monolignol Monolignols, also called lignols, are the source materials for biosynthesis of both lignans and lignin and consist mainly of paracoumaryl alcohol (H), coniferyl alcohol (G) and sinapyl alcohol (S). These monolignols differ in their degree of me ...

s, produced via the phenylpropanoid biochemical pathway. When

copolymer In polymer chemistry, a copolymer is a polymer derived from more than one species of monomer. The polymerization of monomers into copolymers is called copolymerization. Copolymers obtained from the copolymerization of two monomer species are some ...

ized with related aromatic compounds, coniferyl alcohol forms lignin or

lignan The lignans are a large group of low molecular weight polyphenols found in plants, particularly seeds, whole grains, and vegetables. The name derives from the Latin word for "wood". Lignans are precursors to phytoestrogens. They may play a role ...

Coniferin Coniferin is a glucoside of coniferyl alcohol. This white crystalline solid is a metabolite in conifers, serving as an intermediate in cell wall lignification, as well as having other biological roles. It can also be found in the water root extrac ...

is a glucoside of coniferyl alcohol. Coniferyl alcohol is an intermediate in biosynthesis of eugenol and of

stilbenoid Stilbenoids are hydroxylated derivatives of stilbene. They have a C6–C2–C6 structure. In biochemical terms, they belong to the family of phenylpropanoids and share most of their biosynthesis pathway with chalcones. Most stilbenoids are prod ...

s and

coumarin Coumarin () or 2''H''-chromen-2-one is an aromatic organic chemical compound with formula . Its molecule can be described as a benzene molecule with two adjacent hydrogen atoms replaced by a lactone-like chain , forming a second six-membered h ...

Gum benzoin Benzoin or benjamin (corrupted pronunciation) is a balsamic resin obtained from the bark of several species of trees in the genus '' Styrax''. It is used in perfumes and some kinds of incense and as a flavoring and medicine (see tincture of ben ...

contains significant amount of coniferyl alcohol and its

ester In chemistry, an ester is a compound derived from an oxoacid (organic or inorganic) in which at least one hydroxyl group () is replaced by an alkoxy group (), as in the substitution reaction of a carboxylic acid and an alcohol. Glycerides a ...

s. It is found in both

gymnosperm The gymnosperms ( lit. revealed seeds) are a group of seed-producing plants that includes conifers, cycads, '' Ginkgo'', and gnetophytes, forming the clade Gymnospermae. The term ''gymnosperm'' comes from the composite word in el, γυμν ...

and angiosperm plants.

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 ...

and paracoumaryl alcohol, the other two lignin monomers, are found in angiosperm plants and grasses.

Occurrence

Coniferyl alcohol is produced from coniferyl aldehyde 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 ...

enzymes. It is a queen retinue pheromone (QRP), a type of honey bee pheromone found in the mandibular glands. In '' Forsythia intermedia'' a

dirigent protein 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 stere ...

was found to direct the stereoselective biosynthesis of (+)-

pinoresinol Pinoresinol is a tetrahydrofuran lignan found in ''Styrax sp.'', ''Forsythia suspensa, and in Forsythia koreana''. It is also found in the caterpillar of the cabbage butterfly, ''Pieris rapae'' where it serves as a defence against ants. In food, i ...

from coniferyl alcohol. Recently, a second, enantiocomplementary

was identified in '' Arabidopsis thaliana'', which directs enantioselective synthesis of (−)-pinoresinol. (+)-Pinoresinol Biosynthesis

References

{{Phenylpropanoids Monolignols O-methylated phenylpropanoids Semiochemicals Insect pheromones