Coniferyl alcohol

Coniferyl alcohol
Skeletal formula of coniferyl alcohol
Space-filling model of the coniferyl alcohol molecule
Names
IUPAC names
4-(3-hydroxy-1-propenyl)-
2-methoxyphenol
Other names
4-hydroxy-3-methoxycinnamyl alcohol
Coniferol
Identifiers
458-35-5 Yes
ChEBI CHEBI:17745 Yes
ChEMBL ChEMBL501870 Yes
ChemSpider 1266063 Yes
Jmol-3D images Image
PubChem 1549095
Properties
Molecular formula
 C10H12O3
Molar mass 180.20 g·mol−1
Melting point 74 °C (165 °F; 347 K)
Boiling point 163 to 165 °C (325 to 329 °F; 436 to 438 K)
Except where noted otherwise, data is 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

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]

References

  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.