Coniferyl alcohol
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| Space-filling model of the coniferyl alcohol molecule | |
| Names | |
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| IUPAC names
4-(3-hydroxy-1-propenyl)-
2-methoxyphenol |
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| Other names
4-hydroxy-3-methoxycinnamyl alcohol
Coniferol |
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| Identifiers | |
458-35-5  |
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| ChEBI | CHEBI:17745 |
| ChEMBL | ChEMBL501870 |
| ChemSpider | 1266063 |
| Jmol 3D model | Interactive image |
| PubChem | 1549095 |
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| Properties | |
| 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) |
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Except where otherwise noted, 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
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
- ↑ Lua error in package.lua at line 80: module 'strict' not found.
- ↑ 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
- ↑ Lua error in package.lua at line 80: module 'strict' not found.
- ↑ Lua error in package.lua at line 80: module 'strict' not found.
- REDIRECT Template:Monolignol
- REDIRECT Template:Phenylpropanoid
