Vanillin

Vanillin

Names
Preferred IUPAC name 4-Hydroxy-3-methoxybenzaldehyde
Other names Vanillin Methyl vanillin Vanillic aldehyde
Identifiers
CAS Number	121-33-5 Y
3D model (Jmol)	Interactive image
3DMet	B00167
Beilstein Reference	472792
ChEBI	CHEBI:18346 Y
ChEMBL	ChEMBL13883 Y
ChemSpider	13860434 Y
ECHA InfoCard	100.004.060
EC Number	204-465-2
Gmelin Reference	3596
IUPHAR/BPS	6412
KEGG	D00091 Y
MeSH	vanillin
PubChem	1183
RTECS number	YW5775000
UNII	CHI530446X Y
InChI InChI=1S/C8H8O3/c1-11-8-4-6(5-9)2-3-7(8)10/h2-5,8H,1H3 N Key: DPRSTFFEDAVZJW-UHFFFAOYSA-N 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	152.15 g·mol−1
Appearance	White crystals
Odor	Vanilla, Sweet, Balsamic, Pleasant
Density	1.056 g cm−3
Melting point	81 to 83 °C; 178 to 181 °F; 354 to 356 K
Boiling point	285 °C (545 °F; 558 K)
Solubility in water	10 g dm−3
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 (ΔcHo298)	−3.828 MJ mol−1
Hazards
Safety data sheet	hazard.com
GHS pictograms
GHS signal word	WARNING
GHS hazard statements	H302, H317, H319
GHS precautionary statements	P280, P305+351+338
EU classification (DSD)	Xn
R-phrases	R22
NFPA 704	1 1 0
Flash point	147 °C (297 °F; 420 K)
Related compounds
Related compounds	Anisaldehyde Eugenol Phenol Vanillyl alcohol
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
N  (what is YN ?)
Infobox references

Vanillin is a phenolic aldehyde, which is an organic compound with the molecular formula C₈H₈O₃. 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 agent 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. Today, artificial vanillin is made either from guaiacol or lignin.

Lignin-based artificial vanilla flavoring is alleged to have a richer flavor profile than oil-based flavoring; 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.

Vanilla was cultivated as a flavoring by pre-Columbian Mesoamerican people; at the time of their conquest by Hernán Cortés, the Aztecs used it as a flavoring for chocolate. Europeans became aware of both chocolate and vanilla around 1520.