# Syringaldehyde

> Mediated Wiki article. Canonical URL: https://mediated.wiki/source/Syringaldehyde
> Markdown URL: https://mediated.wiki/source/Syringaldehyde.md
> Source: https://en.wikipedia.org/wiki/Syringaldehyde
> Source revision: 1324371105
> License: Creative Commons Attribution-ShareAlike 4.0 International (https://creativecommons.org/licenses/by-sa/4.0/)

{{chembox
| Verifiedfields = changed
| Watchedfields = changed
| verifiedrevid = 470475460
| ImageFile = Syringaldehyde.svg
| PIN = 4-Hydroxy-3,5-dimethoxybenzaldehyde
| OtherNames = 3,5-Dimethoxy-4-hydroxybenzene carbonal, Gallaldehyde 3,5-dimethyl ether, 4-Hydroxy-3,5-dimethoxybenzaldehyde, Syringic aldehyde
|Section1={{Chembox Identifiers
| ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}}
| ChemSpiderID = 8333
| InChI = 1/C9H10O4/c1-12-7-3-6(5-10)4-8(13-2)9(7)11/h3-5,11H,1-2H3
| InChIKey = KCDXJAYRVLXPFO-UHFFFAOYAW
| ChEBI_Ref = {{ebicite|correct|EBI}}
| ChEBI = 67380
| ChEMBL_Ref = {{ebicite|correct|EBI}}
| ChEMBL = 225303
| StdInChI_Ref = {{stdinchicite|correct|chemspider}}
| StdInChI = 1S/C9H10O4/c1-12-7-3-6(5-10)4-8(13-2)9(7)11/h3-5,11H,1-2H3
| StdInChIKey_Ref = {{stdinchicite|correct|chemspider}}
| StdInChIKey = KCDXJAYRVLXPFO-UHFFFAOYSA-N
| CASNo_Ref = {{cascite|correct|CAS}}
| CASNo = 134-96-3
| UNII_Ref = {{fdacite|correct|FDA}}
| UNII = 2ZR01KTT21
| EINECS = 205-167-5
| PubChem = 8655
| SMILES = COc1cc(cc(c1O)OC)C=O
| RTECS = CU5760000
  }}
|Section2={{Chembox Properties
| Formula = C<sub>9</sub>H<sub>10</sub>O<sub>4</sub>
| MolarMass = 182.17 g/mol
| Appearance = colorless solid
| Density = 1.01 g/cm<sup>3</sup>
| MeltingPtC = 110 to 113
| MeltingPt_notes = 
| BoilingPtC = 192 to 193
| BoilingPt_notes = at 19 kPa
| Solubility = Insoluble
  }}
|Section3={{Chembox Hazards
| ExternalSDS = [https://fscimage.fishersci.com/msds/64324.htm External MSDS]
| NFPA-H = 1
| NFPA-F = 0
| NFPA-R = 0
| NFPA-S = 
| GHS_ref=<ref>{{cite web |title=Syringaldehyde |url=https://pubchem.ncbi.nlm.nih.gov/compound/8655#section=Safety-and-Hazards |website=pubchem.ncbi.nlm.nih.gov |language=en}}</ref>
| GHSPictograms = {{GHS07}}
| GHSSignalWord = Warning
| HPhrases = {{H-phrases|302|315|319|335}}
| PPhrases = {{P-phrases|261|264|270|271|280|301+312|302+352|304+340|305+351+338|312|330|332+313|337+313|362|403+233|405|501}}
| FlashPt = >
| FlashPtC = 110
| FlashPt_notes = c.c.
| AutoignitionPt = 
 }}
}}

'''Syringaldehyde''' is an [organic compound](/source/organic_compound) that occurs in trace amounts widely in nature. Some species of insects use syringaldehyde in their chemical communication systems. ''[Scolytus multistriatus](/source/Scolytus_multistriatus)'' uses it as a signal to find a host tree during oviposition.<ref>Vanillin and Syringaldehyde as Attractants for Scolytus multistriatus (Coleoptera: Scolytidae). Meyer H.J. and Norris D.M., Annals of the Entomological Society of America, 17 July 1967, Volume 60, Number 4, pages 858-859, ([http://www.ingentaconnect.com/content/esa/aesa/1967/00000060/00000004/art00024#expand/collapse abstract])</ref>

Because it contains many [functional group](/source/functional_group)s, it can be classified in many ways -  [aromatic](/source/aromaticity), [aldehyde](/source/aldehyde), phenol. It is a colorless solid (impure samples appear yellowish) that is soluble in [alcohol](/source/ethanol) and polar organic solvents.

== Natural sources ==
Syringaldehyde can be found naturally in the wood of [spruce](/source/spruce) and [maple tree](/source/maple_tree)s.<ref>{{cite journal | title = Aromatic Aldehyde from Spruce and Maple Woods |author1=R.H.J. Creighton |author2=J.L. McCarthy |author3=H. Hibbert | journal = [J. Am. Chem. Soc.](/source/J._Am._Chem._Soc.) | volume = 63 | pages = 312 | year = 1941 | doi = 10.1021/ja01846a501 |bibcode=1941JAChS..63Q.312C }}</ref>

Syringaldehyde is also formed in [oak](/source/oak) barrels and extracted into [whisky](/source/whisky), which it gives spicy, smoky, hot and smoldering wood aromas.

== Preparation ==
This compound may be prepared from [syringol](/source/syringol) by the [Duff reaction](/source/Duff_reaction):<ref>{{OrgSynth | author = C. F. H. Allen and Gerhard W. Leubner | title = Syringic aldehyde | collvol = 4 | collvolpages = 866 | year = 1963 | prep = cv4p0866}}</ref>

:300px

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

== References ==
<references/>

Category:Insect pheromones
Category:O-methylated natural phenols
Category:4-Hydroxybenzaldehyde derivatives
Category:Phenol ethers

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