Coniferyl alcohol
{{chembox
| Verifiedfields = changed
| Watchedfields = changed
| verifiedrevid = 460106847
| Name = Coniferyl alcohol
| ImageFile = Coniferol.svg
| ImageSize =
| ImageAlt = Skeletal formula of coniferyl alcohol
| ImageFile1 = Coniferyl alcohol 3D spacefill.png
| ImageSize1 =
| ImageAlt1 = Space-filling model of the coniferyl alcohol molecule
| ImageName = Coniferyl alcohol
| PIN = 4-[(1E)-3-Hydroxyprop-1-en-1-yl]-2-methoxyphenol
| OtherNames = 4-hydroxy-3-methoxycinnamyl alcohol
Coniferol
|Section1={{Chembox Identifiers
| ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}}
| ChemSpiderID = 1266063
| 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+
| InChIKey = JMFRWRFFLBVWSI-NSCUHMNNBF
| StdInChI_Ref = {{stdinchicite|correct|chemspider}}
| StdInChI = 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+
| StdInChIKey_Ref = {{stdinchicite|correct|chemspider}}
| StdInChIKey = JMFRWRFFLBVWSI-NSCUHMNNSA-N
| CASNo_Ref = {{cascite|correct|CAS}}
| CASNo = 458-35-5
| UNII_Ref = {{fdacite|changed|FDA}}
| UNII = E7SM92591P
| ChEMBL_Ref = {{ebicite|correct|EBI}}
| ChEMBL = 501870
| PubChem = 1549095
| ChEBI_Ref = {{ebicite|correct|EBI}}
| ChEBI = 17745
| EC_number = 207-277-9
| Beilstein = 2048963
| KEGG = C00590
| SMILES = Oc1ccc(cc1OC)/C=C/CO
}}
|Section2={{Chembox Properties
| C=10 | H=12 | O=3
| Density =
| MeltingPtC = 74
| BoilingPtC = 163 to 165
| BoilingPt_notes =
}}
| Section7 = {{Chembox Hazards
| GHSPictograms = {{GHS07}}
| GHSSignalWord = Warning
| HPhrases = {{H-phrases|315|319|335}}
| PPhrases = {{P-phrases|261|264|271|280|302+352|304+340|305+351+338|312|321|332+313|337+313|362|403+233|405|501}}
}}
}}
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.{{Cite journal | first1 = Kenji | last1 = Iiyama | first2 = Thi Bach-Tuyet | last2 = Lam | first3 = Bruce A. | last3 = Stone | title = Covalent Cross-Links in the Cell Wall | journal = Plant Physiology | year = 1994 | volume = 104 | issue = 2 | pages = 315–320 | pmid = 12232082 | pmc = 159201 | doi = 10.1104/pp.104.2.315}}Wout Boerjan, John Ralph, Marie Baucher "Lignin Biosynthesis" Annu. Rev. Plant Biol. 2003, vol. 54, pp. 519–46. {{doi|10.1146/annurev.arplant.54.031902.134938}}{{cite journal |doi=10.1105/tpc.010111|title=The Last Step of Syringyl Monolignol Biosynthesis in Angiosperms is Regulated by a Novel Gene Encoding Sinapyl Alcohol Dehydrogenase |year=2001 |last1=Li |first1=Laigeng |last2=Cheng |first2=Xiao Fei |last3=Leshkevich |first3=Jacqueline |last4=Umezawa |first4=Toshiaki |last5=Harding |first5=Scott A. |last6=Chiang |first6=Vincent L. |journal=The Plant Cell |volume=13 |issue=7 |pages=1567–1586 |pmid=11449052 |pmc=139549 |bibcode=2001PlanC..13.1567L }} 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.
Occurrence
Coniferyl alcohol is produced from coniferyl aldehyde by the action of dehydrogenase enzymes.
It is a queen retinue pheromone (QRP), a type of honey bee pheromone found in the mandibular glands.{{cite journal|last1=Keeling|first1=C. I.|last2=Slessor|first2=K. N.|last3=Higo|first3=H. A.|last4=Winston|first4=M. L.|date=2003|title=Isolation and identification of new components of the honey bee (Apis mellifera L.) queen retinue pheromone|journal=Proc. Natl. Acad. Sci. U.S.A.|volume=100|issue=8|pages=4486–4491|doi=10.1073/pnas.0836984100|pmc=153582|pmid=12676987|bibcode=2003PNAS..100.4486K |doi-access=free}}
In Forsythia intermedia a dirigent protein was found to direct the stereoselective biosynthesis of (+)-pinoresinol from coniferyl alcohol.{{cite journal |last1=Davin |first1=L. B. |last2=Wang |first2=H. B. |last3=Crowell |first3=A. L. |title=Stereoselective bimolecular phenoxy radical coupling by an auxiliary (dirigent) protein without an active center |journal=Science |volume=275 |issue=5298 |pages=362–366 |year=1997 |pmid=8994027 |doi=10.1126/science.275.5298.362|s2cid=41957412 |display-authors=etal}} Recently, a second, enantiocomplementary dirigent protein was identified in Arabidopsis thaliana, which directs enantioselective synthesis of (−)-pinoresinol.{{cite journal|last1=Pickel |first1=B. |last2=Constantin |first2=M.-A. |last3=Pfannsteil |first3=J. |last4=Conrad |first4=J. |last5=Beifuss |first5=U. |last6=Schaffer |first6=A. |title=An Enantiocomplementary Dirigent Protein for the Enantioselective Laccase-Catalyzed Oxidative Coupling of Phenols |journal=Angewandte Chemie |volume=53 |issue=4 |pages=273–284 |date=March 2007 |doi=10.1007/s10086-007-0892-x|s2cid=195313754 |doi-access=free }}
