Editing Vanillin (section)

{{Chembox
| Verifiedfields = changed
| Watchedfields = changed
| verifiedrevid = 456486843
| ImageFileL1 = Vanillin v3.svg
| ImageSizeL1 = 100px
| ImageFileL1_Ref = {{chemboximage|correct|??}}
| ImageNameL1 = Skeletal formula of vanillin 
| ImageFileR1 = Vanillin-3d.png
| ImageSizeR1 = 150px
| ImageFileR1_Ref = {{chemboximage|correct|??}}
| ImageNameR1 = Spacefill model of vanillin 
| ImageFile2 = Vanlilin vzorek.jpg
| PIN = 4-Hydroxy-3-methoxybenzaldehyde
| OtherNames = Vanillin<ref name=Vanillin>{{cite web|url = http://sci-toys.com/ingredients/vanillin.html |title = Vanillin|first = Simon Quellen|last =Field|website = sci-toys.com}}</ref><br />Methyl vanillin<ref name=Vanillin/><br />Vanillic aldehyde<ref name=PubChem>{{PubChem|1183}}.</ref>
|Section1={{Chembox Identifiers
| IUPHAR_ligand = 6412
| CASNo = 121-33-5
| CASNo_Ref = {{cascite|correct|CAS}}
| PubChem = 1183
| ChemSpiderID = 13860434
| ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}}
| UNII = CHI530446X
| UNII_Ref = {{fdacite|correct|FDA}}
| EINECS = 204-465-2
| KEGG = D00091
| KEGG_Ref = {{keggcite|correct|kegg}}
| MeSHName = vanillin
| ChEBI = 18346
| ChEBI_Ref = {{ebicite|correct|EBI}}
| ChEMBL = 13883
| ChEMBL_Ref = {{ebicite|correct|EBI}}
| RTECS = YW5775000
| Beilstein = 472792
| Gmelin = 3596
| 3DMet = B00167
| SMILES = c1(C=O)cc(OC)c(O)cc1
| StdInChI = 1S/C8H8O3/c1-11-8-4-6(5-9)2-3-7(8)10/h2-5,8H,1H3
| StdInChI_Ref = {{stdinchicite|changed|chemspider}}
| InChI = 1/C8H8O3/c1-11-8-4-6(5-9)2-3-7(8)10/h2-5,10H,1H3
| StdInChIKey = MWOOGOJBHIARFG-UHFFFAOYSA-N
| StdInChIKey_Ref = {{stdinchicite|changed|chemspider}}
| InChIKey = MWOOGOJBHIARFG-UHFFFAOYAS
}}
|Section2={{Chembox Properties
| C=8 | H=8 | O=3 
| Appearance = White solid
| Odor = Vanilla, sweet, balsamic, pleasant
| Density = 1.056 g/cm<sup>3</sup><ref name=crc1>{{cite book | editor= Haynes, William M. | date = 2016| title = [[CRC Handbook of Chemistry and Physics]] | edition = 97th | publisher = [[CRC Press]] | isbn = 978-1-4987-5429-3|page=3.310}}</ref>
| MeltingPtC = 81
| BoilingPtC = 285
| MeltingPt_ref=<ref name=crc1/>
| BoilingPt_ref=<ref name=crc1/>
| Solubility = 10 g/L
| LogP = 1.208
| VaporPressure = >1 Pa
| pKa = 7.781
| pKb = 6.216
}}
|Section3={{Chembox Structure
| CrystalStruct = Monoclinic
}}
|Section4={{Chembox Thermochemistry
| DeltaHc = −3.828 MJ/mol
}}
|Section5={{Chembox Hazards
| ExternalSDS = [https://www.inchem.org/documents/icsc/icsc/eics1740.htm ICSC 1740]
| GHSPictograms = {{GHS exclamation mark}}
| GHSSignalWord = '''WARNING'''
| HPhrases = {{H-phrases|302|317|319}}
| PPhrases = {{P-phrases|280|305+351+338}}
| NFPA-F = 1
| NFPA-H = 1
| NFPA-R = 0
| FlashPtC = 147
}}
|Section6={{Chembox Related
| OtherCompounds = [[Anisaldehyde]]<br/>[[Apocynin]]<br/>[[Eugenol]]<br/>[[Phenol]]<br/>[[Vanillyl alcohol]]
}}
}}

'''Vanillin''' is an [[organic compound]] with the molecular formula {{chem2|auto=1|C8H8O3}}.  It is a [[phenolic aldehyde]].  Its [[functional groups]] include [[aldehyde]], [[hydroxyl]], and [[ether]].  It is the primary component of the ethanolic extract of the [[vanilla bean]].  Synthetic vanillin is now used more often than natural vanilla extract as a [[flavoring]] in foods, beverages, and pharmaceuticals.

Vanillin and [[ethylvanillin]] are used by the food industry;  ethylvanillin is more expensive, but has a stronger [[Note (perfumery)|note]]. It differs from vanillin by having an ethoxy group (−O−CH<sub>2</sub>CH<sub>3</sub>) instead of a methoxy group (−O−CH<sub>3</sub>).

Natural [[vanilla extract]] is a mixture of several hundred different compounds in addition to vanillin.  Artificial vanilla flavoring is often a solution of pure vanillin, usually of synthetic origin. Because of the scarcity and expense of natural vanilla extract,  synthetic preparation of its predominant component has long been of interest.  The first commercial synthesis of vanillin began with the more readily available natural compound [[eugenol]] (4-allyl-2-methoxyphenol).  Today, artificial vanillin is made either from [[guaiacol]] or [[lignin]].

Lignin-based artificial vanilla flavoring is alleged to have a richer flavor profile than that from guaiacol-based artificial vanilla; the difference is due to the presence of [[acetovanillone]], a minor component in the lignin-derived product that is not found in vanillin synthesized from guaiacol.{{efn|name=lig-vanillone|According to [[#esposito1997|Esposito 1997]], blind taste-testing panels cannot distinguish between the flavors of synthetic vanillin from lignin and those from guaicol, but can distinguish the odors of these two types of synthetic vanilla extracts.  Guaiacol vanillin, adulterated with acetovanillone, has an odor indistinguishable from lignin vanillin.}}