Coniferyl alcohol: Difference between revisions

| 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-[(1''E'')-3-Hydroxyprop-1-en-1-yl]-2-methoxyphenol

| OtherNames = 4-hydroxy-3-methoxycinnamyl alcohol<br>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

| ChEBI_Ref = {{ebicite|correct|EBI}}

| EC_number = 207-277-9

| Beilstein = 2048963

| KEGG = C00590

|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 [[monolignol]]s, produced via the [[phenylpropanoid biochemical pathway]]. When [[copolymer]]ized with related [[aromatic compound]]s, coniferyl alcohol forms [[lignin]] or [[lignan]]s.<ref>{{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}}</ref><ref>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}}</ref><ref name=PNAS>{{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 }}</ref> [[Coniferin]] is a [[glucoside]] of coniferyl alcohol. Coniferyl alcohol is an intermediate in [[biosynthesis]] of [[eugenol]] and of [[stilbenoid]]s and [[coumarin]]. [[Gum benzoin]] contains significant amount of coniferyl alcohol and its [[ester]]s. 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.<ref name=PNAS/>

It is a [[queen retinue pheromone]] (QRP), a type of [[honey bee pheromone]] found in the [[mandibular glands]].<ref>{{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}}</ref>

In ''[[Forsythia intermedia]]'' a [[dirigent protein]] was found to direct the stereoselective biosynthesis of (+)-[[pinoresinol]] from coniferyl alcohol.<ref>{{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}}</ref> Recently, a second, enantiocomplementary [[dirigent protein]] was identified in ''[[Arabidopsis thaliana]]'', which directs enantioselective synthesis of (−)-pinoresinol.<ref>{{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 }}</ref>

[[File:(+)-Pinoresinol Biosynthesis.svg|450px|alt=(+)-Pinoresinol biosynthesis|Reaction of monolignol radicals in the presence of dirigent protein to form (+)-pinoresinol]]

== References ==

{{reflist|30em}}

[[Category:O-methylated phenylpropanoids]]

[[Category:Semiochemicals]]

[[Category:Insect pheromones]]