Coniferyl alcohol

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Coniferyl alcohol
Coniferyl alcohol
Identifiers
CAS number 458-35-5 YesY
PubChem 1549095
ChemSpider 1266063 YesY
ChEBI CHEBI:17745 YesY
ChEMBL CHEMBL501870 YesY
Jmol-3D images Image 1
Properties
Molecular formula C10H12O3
Molar mass 180.20 g mol−1
Melting point 74 °C
Boiling point 163–165 °C
Except where noted otherwise, data are given for materials in their standard state (at 25 °C (77 °F), 100 kPa)
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Infobox references

Coniferyl alcohol is an organic compound. This colourless crystalline solid is a phytochemical, one of the monolignols. It is synthethized via the phenylpropanoid biochemical pathway. When copolymerized with related aromatic compounds, coniferyl alcohol forms lignin or lignans.[1] 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.

It is a queen retinue pheromone (QRP), a type of honey bee pheromone found in the mandibular glands.[2]

Pinoresinol biosynthesis[edit]

A first dirigent protein was discovered in Forsythia intermedia. This protein has been found to direct the stereoselective biosynthesis of (+)-pinoresinol from coniferyl alcohol monomers.[3] Recently, a second, enantiocomplementary dirigent protein was identified in Arabidopsis thaliana, which directs enantioselective synthesis of (-)-pinoresinol.[4]

Reaction of monolignol radicals in the presence of dirigent protein to form (+)-pinoresinol

References[edit]

  1. ^ Kenji liyama, Thi Bach-Tuyet Lam, and Bruce A. Stone (1994). "Covalent Cross-Links in the Cell Wall". Plant Physiology 104 (2): 315–320. PMC 159201. PMID 12232082. 
  2. ^ Keeling, C. I., Slessor, K. N., Higo, H. A. and Winston, M. L. (2003) Isolation and identification of new components of the honey bee (Apis mellifera L.) queen retinue pheromone. PNAS, April 15, 2003 vol. 100 no. 8 4486-4491, doi:10.1073/pnas.0836984100
  3. ^ Davin LB, Wang HB, Crowell AL, et al. (1997). "Stereoselective bimolecular phenoxy radical coupling by an auxiliary (dirigent) protein without an active center". Science 275 (5298): 362–6. doi:10.1126/science.275.5298.362. PMID 8994027. 
  4. ^ Pickel B, Constantin M-A, Pfannsteil J, Conrad J, Beifuss U, Schaffer A (March 2007). "An Enantiocomplementary Dirigent Protein for the Enantioselective Laccase-Catalyzed Oxidative Coupling of Phenols". Angewandte Chemistry 53 (4): 273–284. doi:10.1007/s10086-007-0892-x.