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 =
| 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
See also
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- Phenolic content in wine
- Syringol
- Syringic acid
- Acetosyringone
- Sinapyl alcohol
- Sinapinic acid
- Sinapaldehyde
- Sinapine
- Canolol
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