# Sinapaldehyde

> Mediated Wiki article. Canonical URL: https://mediated.wiki/source/Sinapaldehyde
> Markdown URL: https://mediated.wiki/source/Sinapaldehyde.md
> Source: https://en.wikipedia.org/wiki/Sinapaldehyde
> Source revision: 1301027777
> License: Creative Commons Attribution-ShareAlike 4.0 International (https://creativecommons.org/licenses/by-sa/4.0/)

{{Chembox
| ImageFile = Sinapaldehyde.svg
| ImageFile_Ref = {{chemboximage|correct|??}}
| ImageSize = 244
| ImageName = Kekulé skeletal formula of sinapaldehyde (2E)-2-en with some implicit hydrogens shown and one explicit hydrogen added
| SystematicName = (''E'')-3-(4-Hydroxy-3,5-dimethoxyphenyl)prop-2-enal<ref>{{Cite web|title = AC1L3OEQ - Compound Summary|url = https://pubchem.ncbi.nlm.nih.gov/compound/119216|work = The PubChem Project|location = USA|publisher = National Center for Biotechnology Information}}</ref>
| OtherNames = {{ubl|
* (''trans'')-3,5-Dimethoxy-4-hydroxycinnamaldehyde
* Sinapic aldehyde
* Sinapinaldehyde
* Sinapoyl aldehyde
* Sinapyl aldehyde
}}
|Section1={{Chembox Identifiers
| CASNo = 4206-58-0
| CASNo_Comment = 
| 3DMet = B00807
| Beilstein = 2215799
| ChemSpiderID = 4444359
| ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}}
| EINECS = 627-731-3
| KEGG = C05610
| MeSHName = Sinapaldehyde
| ChEBI = 27949
| ChEMBL = 225067
| ChEMBL_Ref = {{ebicite|correct|EBI}}
| PubChem = 5280802
| SMILES = COC1=CC(=CC(=C1O)OC)/C=C/C=O
| StdInChI = 1S/C11H12O4/c1-14-9-6-8(4-3-5-12)7-10(15-2)11(9)13/h3-7,13H,1-2H3/b4-3+
| StdInChIKey = CDICDSOGTRCHMG-ONEGZZNKSA-N
}}
|Section2={{Chembox Properties
| C = 11
| H = 12
| O = 4
| MeltingPtC = 104 to 106
| LogP = 1.686
| pKa = 9.667
| pKb = 4.330
}}
|Section3={{Chembox Hazards
| GHS_ref=<ref>{{cite web |title=C&L Inventory |url=https://www.echa.europa.eu/web/guest/information-on-chemicals/cl-inventory-database/-/discli/details/160751 |website=www.echa.europa.eu}}</ref>
| GHSPictograms = {{GHS07}}
| GHSSignalWord = Warning
| HPhrases = {{H-phrases|315|319|335}}
| PPhrases = {{P-phrases|}}
}}
|Section4={{Chembox Related
| OtherFunction_label = alkenals
| OtherFunction = [Cinnamaldehyde](/source/Cinnamaldehyde)<br />
[Coniferyl aldehyde](/source/Coniferyl_aldehyde)<br />
[DMACA reagent](/source/DMACA_reagent)<br />
[2-Nitrocinnamaldehyde](/source/2-Nitrocinnamaldehyde)
}}
}}

'''Sinapaldehyde''' is an [organic compound](/source/organic_compound) with the formula HO(CH<sub>3</sub>O)<sub>2</sub>C<sub>6</sub>H<sub>2</sub>CH=CHCHO.  It is a derivative of [cinnamaldehyde](/source/cinnamaldehyde), featuring one [hydroxy group](/source/hydroxy_group) and two [methoxy group](/source/methoxy_group)s as [substituent](/source/substituent)s. It is an intermediate in the formation of [sinapyl alcohol](/source/sinapyl_alcohol), a [lignol](/source/Monolignol) that is a major precursor to [lignin](/source/lignin).<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=TPC>{{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 }}</ref>

==Biosynthetic role==
In sweetgum (''[Liquidambar styraciflua](/source/Liquidambar_styraciflua)''), sinapaldehyde arises in two steps from [coniferyl aldehyde](/source/coniferyl_aldehyde) beginning with [hydroxylation](/source/hydroxylation) mediated by coniferyl aldehyde 5-hydroxylase.  The diphenol is then methylated at the 5-OH by the action of [caffeate ''O''-methyltransferase](/source/caffeate_O-methyltransferase).<ref>{{cite journal |doi=10.1073/pnas.96.16.8955|title=Coniferyl aldehyde 5-hydroxylation and methylation direct syringyl lignin biosynthesis in angiosperms |year=1999 |last1=Osakabe |first1=Keishi |last2=Tsao |first2=Cheng Chung |last3=Li |first3=Laigeng |last4=Popko |first4=Jacqueline L. |last5=Umezawa |first5=Toshiaki |last6=Carraway |first6=Daniel T. |last7=Smeltzer |first7=Richard H. |last8=Joshi |first8=Chandrashekhar P. |last9=Chiang |first9=Vincent L. |journal=Proceedings of the National Academy of Sciences |volume=96 |issue=16 |pages=8955–8960 |pmid=10430877 |pmc=17714 |bibcode=1999PNAS...96.8955O |doi-access=free }}</ref>

Sinapaldehyde is reduced to the alcohol by the action of [dehydrogenase](/source/dehydrogenase) enzymes.<ref name=TPC/> In ''[Arabidopsis thaliana](/source/Arabidopsis_thaliana)'', the enzyme [dihydroflavonol 4-reductase](/source/dihydroflavonol_4-reductase) uses NADP<sup>+</sup> to reduce sinapaldehyde to sinapyl alcohol.<ref>{{Cite web |url=http://arabidopsisreactome.org/cgi-bin/eventbrowser?DB=test_reactome_9_ath_all&FOCUS_SPECIES=Arabidopsis_thaliana&ID=43094& |title=Dihydroflavonol 4-reductase on arabidopsisreactome.org |access-date=2009-10-26 |archive-date=2016-01-30 |archive-url=https://web.archive.org/web/20160130221202/http://arabidopsisreactome.org/cgi-bin/eventbrowser?DB=test_reactome_9_ath_all&FOCUS_SPECIES=Arabidopsis_thaliana&ID=43094& |url-status=dead }}</ref>

It is found in ''[Senra incana](/source/Senra_incana)'' (Hibisceae). It is a low molecular weight [phenol](/source/natural_phenol) that is susceptible to extraction from [cork stopper](/source/Cork_(material))s into wine.<ref>Polyphenolic Composition of ''Quercus suber'' Cork from Different Spanish Provenances. Elvira Conde, Estrella Cadahía, María Concepción García-Vallejo and Brígida Fernández de Simón, J. Agric. Food Chem., 1998, volume 46, pp 3166–3171 {{doi|10.1021/jf970863k}}</ref>

== See also ==
{{Div col|colwidth=16em}}
*[Phenolic content in wine](/source/Phenolic_content_in_wine)
*[Syringaldehyde](/source/Syringaldehyde)
*[Syringol](/source/Syringol)
*[Syringic acid](/source/Syringic_acid)
*[Acetosyringone](/source/Acetosyringone)
*[Sinapinic acid](/source/Sinapinic_acid)
*[Sinapine](/source/Sinapine)
*[Canolol](/source/Canolol)
{{Div col end}}

== References ==
{{Reflist}}

Category:Natural phenols
Category:Aldehydes
Category:O-methylated phenylpropanoids

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Adapted from the Wikipedia article [Sinapaldehyde](https://en.wikipedia.org/wiki/Sinapaldehyde) by Wikipedia contributors ([contributor history](https://en.wikipedia.org/wiki/Sinapaldehyde?action=history)). Available under [Creative Commons Attribution-ShareAlike 4.0 International](https://creativecommons.org/licenses/by-sa/4.0/). Changes may have been made.