Syringaldehyde
title: "Syringaldehyde" type: doc version: 1 created: 2026-02-28 author: "Wikipedia contributors" status: active scope: public tags: ["insect-pheromones", "o-methylated-natural-phenols", "4-hydroxybenzaldehyde-derivatives", "phenol-ethers"] topic_path: "general/insect-pheromones" source: "https://en.wikipedia.org/wiki/Syringaldehyde" license: "CC BY-SA 4.0" wikipedia_page_id: 0 wikipedia_revision_id: 0
| 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 = | 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 = | ChEBI = 67380 | ChEMBL_Ref = | ChEMBL = 225303 | StdInChI_Ref = | StdInChI = 1S/C9H10O4/c1-12-7-3-6(5-10)4-8(13-2)9(7)11/h3-5,11H,1-2H3 | StdInChIKey_Ref = | StdInChIKey = KCDXJAYRVLXPFO-UHFFFAOYSA-N | CASNo_Ref = | CASNo = 134-96-3 | UNII_Ref = | 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 = External MSDS | NFPA-H = 1 | NFPA-F = 0 | NFPA-R = 0 | NFPA-S = | GHS_ref= | GHSPictograms = | GHSSignalWord = Warning | HPhrases = | PPhrases = | 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.
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.
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:
:[[File:Duff reaction syringaldehyde.svg|300px]]
References
References
- "Syringaldehyde".
- 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])
- (1941). "Aromatic Aldehyde from Spruce and Maple Woods". [[J. Am. Chem. Soc.]].
- C. F. H. Allen and Gerhard W. Leubner. (1963). "Syringic aldehyde".
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