Coniferyl alcohol

Coniferyl alcohol

Names
IUPAC name 4-(3-hydroxy-1-propenyl)-2-methoxyphenol
Other names 4-hydroxy-3-methoxycinnamyl alcohol Coniferol
Identifiers
CAS Number	32811-40-8 N
3D model (Jmol)	Interactive image
ChEBI	CHEBI:17745 Y
ChemSpider	1266063 Y
ECHA InfoCard	100.006.617
PubChem CID	1549095
UNII	E7SM92591P N
InChI InChI=1S/C10H12O3/c1-13-10-7-8(3-2-6-11)4-5-9(10)12/h2-5,7,11-12H,6H2,1H3/b3-2+ Y Key: JMFRWRFFLBVWSI-NSCUHMNNSA-N Y InChI=1/C10H12O3/c1-13-10-7-8(3-2-6-11)4-5-9(10)12/h2-5,7,11-12H,6H2,1H3/b3-2+ Key: JMFRWRFFLBVWSI-NSCUHMNNBF
SMILES Oc1ccc(cc1OC)/C=C/CO
Properties
Chemical 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 otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
N  (what is YN ?)
Infobox references

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

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. Recently, a second, enantiocomplementary dirigent protein was identified in Arabidopsis thaliana, which directs enantioselective synthesis of (−)-pinoresinol.