Coniferyl alcohol

Coniferyl alcohol
IUPAC name 4-(3-hydroxy-1-propenyl)- 2-methoxyphenol
Other names 4-hydroxy-3-methoxycinnamyl alcohol
Identifiers
CAS number	458-35-5 Y
PubChem	1549095
ChemSpider	1266063 Y
ChEBI	CHEBI:17745 Y
ChEMBL	CHEMBL501870 Y
Jmol-3D images	Image 1
SMILES Oc1ccc(cc1OC)/C=C/CO
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
Properties
Molecular formula	C10H12O3
Molar mass	180.2 g mol−1
Melting point	74 °C
Boiling point	163-165 °C
Y (verify) (what is: Y/N?) Except where noted otherwise, data are given for materials in their standard state (at 25 °C, 100 kPa)
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]

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. http://www.pubmedcentral.nih.gov/articlerender.fcgi?tool=pmcentrez&artid=159201. 
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