{{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 that occurs in trace amounts widely in nature. Some species of insects use syringaldehyde in their chemical communication systems. ''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 groups, it can be classified in many ways - aromatic, aldehyde, phenol. It is a colorless solid (impure samples appear yellowish) that is soluble in alcohol and polar organic solvents.
== Natural sources == Syringaldehyde can be found naturally in the wood of spruce and maple trees.<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. | volume = 63 | pages = 312 | year = 1941 | doi = 10.1021/ja01846a501 |bibcode=1941JAChS..63Q.312C }}</ref>
Syringaldehyde is also formed in oak barrels and extracted into whisky, which it gives spicy, smoky, hot and smoldering wood aromas.
== Preparation == This compound may be prepared from syringol by the 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 *Syringol *Syringic acid *Acetosyringone *Sinapyl alcohol *Sinapinic acid *Sinapaldehyde *Sinapine *Canolol {{Div col end}}
== References == <references/>
Category:Insect pheromones Category:O-methylated natural phenols Category:4-Hydroxybenzaldehyde derivatives Category:Phenol ethers