Vanillin

Vanillin
Skeletal formula of a vanillin minor tautomer	Spacefill model of a vanillin minor tautomer
Names
	Preferred IUPAC name 4-Hydroxy-3-methoxybenzaldehyde
	Other names Vanillin; Methyl vanillin; Vanillic aldehyde
Identifiers
CAS Number	121-33-5 ;
3D model (JSmol)	Interactive image;
3DMet	B00167;
Beilstein Reference	472792
ChEBI	CHEBI:18346 ;
ChEMBL	ChEMBL13883 ;
ChemSpider	13860434 ;
ECHA InfoCard	100.004.060
EC Number	204-465-2;
Gmelin Reference	3596
IUPHAR/BPS	6412;
KEGG	D00091 ;
MeSH	vanillin
PubChem CID	1183;
RTECS number	YW5775000;
UNII	CHI530446X ;
CompTox Dashboard (EPA)	DTXSID0021969 ;
	InChI InChI=1S/C8H8O3/c1-11-8-4-6(5-9)2-3-7(8)10/h2-5,8H,1H3 Key: MWOOGOJBHIARFG-UHFFFAOYSA-N ; InChI=1/C8H8O3/c1-11-8-4-6(5-9)2-3-7(8)10/h2-5,10H,1H3 Key: MWOOGOJBHIARFG-UHFFFAOYAS;
	SMILES c1(C=O)cc(OC)c(O)cc1;
Properties
Chemical formula	C8H8O3
Molar mass	152.149 g·mol−1
Appearance	White solid
Odor	Vanilla, sweet, balsamic, pleasant
Density	1.056 g/cm3
Melting point	81 °C (178 °F; 354 K)
Boiling point	285 °C (545 °F; 558 K)
Solubility in water	10 g/L
log P	1.208
Vapor pressure	>1 Pa
Acidity (pKa)	7.781
Basicity (pKb)	6.216
Structure
Crystal structure	Monoclinic
Thermochemistry
Std enthalpy of; combustion (ΔcH⦵298)	−3.828 MJ/mol
Hazards
	GHS labelling:
Pictograms
Signal word	Warning
Hazard statements	H302, H317, H319
Precautionary statements	P280, P305+P351+P338
NFPA 704 (fire diamond)	1 1 0
Flash point	147 °C (297 °F; 420 K)
Safety data sheet (SDS)	ICSC 1740
Related compounds
Related compounds	Anisaldehyde; Apocynin; Eugenol; Phenol; Vanillyl alcohol
	Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa). verify (what is ?) Infobox references

Vanillin is an organic compound with the molecular formula C₈H₈O₃. It is a phenolic aldehyde. Its functional groups include aldehyde, hydroxyl, and ether. It is the primary component of the 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. It differs from vanillin by having an ethoxy group (−O−CH₂CH₃) instead of a methoxy group (−O−CH₃).

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 guiacol-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.^[4]

^ ^a ^b Field, Simon Quellen. "Vanillin". sci-toys.com.
^ CID 1183 from PubChem.
^ ^a ^b ^c Haynes, William M., ed. (2016). CRC Handbook of Chemistry and Physics (97th ed.). CRC Press. p. 3.310. ISBN 978-1-4987-5429-3.
^ According to 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.

[Vanillin-1] Field, Simon Quellen. "Vanillin". sci-toys.com.

[PubChem-2] CID 1183 from PubChem.

[crc1-3] Haynes, William M., ed. (2016). CRC Handbook of Chemistry and Physics (97th ed.). CRC Press. p. 3.310. ISBN 978-1-4987-5429-3.

[4] According to 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.

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