Syringaldehyde

{{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 = C9H10O4

| MolarMass = 182.17 g/mol

| Appearance = colorless solid

| Density = 1.01 g/cm3

| 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={{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}}

| 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.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])

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. Its refractive index is 1.53.{{citation needed|date=July 2014}}

Natural sources

Syringaldehyde can be found naturally in the wood of spruce and maple trees.{{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}}

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:{{OrgSynth | author = C. F. H. Allen and Gerhard W. Leubner | title = Syringic aldehyde | collvol = 4 | collvolpages = 866 | year = 1963 | prep = cv4p0866}}

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See also

References