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Chemical compound From Wikipedia, the free encyclopedia
Coniferyl alcohol is an organic compound with the formula HO(CH3O)C6H3CH=CHCH2OH. A colourless or white solid, it is one of the monolignols, produced via the phenylpropanoid biochemical pathway. When copolymerized with related aromatic compounds, coniferyl alcohol forms lignin or lignans.[1][2][3] 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.
Names | |
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Preferred IUPAC name
4-[(1E)-3-Hydroxyprop-1-en-1-yl]-2-methoxyphenol | |
Other names
4-hydroxy-3-methoxycinnamyl alcohol Coniferol | |
Identifiers | |
3D model (JSmol) |
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2048963 | |
ChEBI | |
ChEMBL | |
ChemSpider | |
ECHA InfoCard | 100.260.977 |
EC Number |
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KEGG | |
PubChem CID |
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UNII | |
CompTox Dashboard (EPA) |
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Properties | |
C10H12O3 | |
Molar mass | 180.203 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) |
Hazards | |
GHS labelling: | |
Warning | |
H315, H319, H335 | |
P261, P264, P271, P280, P302+P352, P304+P340, P305+P351+P338, P312, P321, P332+P313, P337+P313, P362, P403+P233, P405, P501 | |
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
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Coniferyl alcohol is produced from coniferyl aldehyde by the action of dehydrogenase enzymes.[3]
It is a queen retinue pheromone (QRP), a type of honey bee pheromone found in the mandibular glands.[4]
In Forsythia intermedia a dirigent protein was found to direct the stereoselective biosynthesis of (+)-pinoresinol from coniferyl alcohol.[5] Recently, a second, enantiocomplementary dirigent protein was identified in Arabidopsis thaliana, which directs enantioselective synthesis of (−)-pinoresinol.[6]
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