Common NameVanillin
DescriptionVanillin, also known as vanillaldehyde or lioxin, belongs to the class of organic compounds known as methoxyphenols. Methoxyphenols are compounds containing a methoxy group attached to the benzene ring of a phenol moiety. It is used by the food industry as well as ethylvanillin. Vanillin exists in all living species, ranging from bacteria to humans. Vanillin is a sweet, chocolate, and creamy tasting compound. Vanillin is found, on average, in the highest concentration within a few different foods, such as corns, ryes, and sherries and in a lower concentration in beers, rums, and oats. Vanillin has also been detected, but not quantified, in several different foods, such as gooseberries, other bread, brazil nuts, shea tree, and ohelo berries. This could make vanillin a potential biomarker for the consumption of these foods. Vanillin is a potentially toxic compound. Synthetic vanillin, instead of natural Vanillin extract, is sometimes used as a flavouring agent in foods, beverages, and pharmaceuticals. Vanillin is the primary component of the extract of the Vanillin bean. Because of the scarcity and expense of natural Vanillin extract, there has long been interest in the synthetic preparation of its predominant component. Artificial Vanillin flavoring is a solution of pure vanillin, usually of synthetic origin. Today, artificial vanillin is made from either guaiacol or from lignin, a constituent of wood which is a byproduct of the paper industry. The first commercial synthesis of vanillin began with the more readily available natural compound eugenol.
Structure
Molecular FormulaC8H8O3
Average Mass152.14730
Monoisotopic Mass152.04734
IUPAC Name4-hydroxy-3-methoxybenzaldehyde
Traditional NameVanillin
CAS Registry Number121-33-5
SMILESCOc1cc(C=O)ccc1O
InChI IdentifierInChI=1S/C8H8O3/c1-11-8-4-6(5-9)2-3-7(8)10/h2-5,10H,1H3
InChI KeyMWOOGOJBHIARFG-UHFFFAOYSA-N
CHEBI IDCHEBI:18346
HMDB IDHMDB0012308
StateNot Available
Water Solubility5.05e+00 g/l
logP1.31
logS-1.48
pKa (Strongest Acidic)7.81
pKa (Strongest Basic)-4.90
Hydrogen Acceptor Count3
Hydrogen Donor Count1
Polar Surface Area46.53 Ų
Rotatable Bond Count2
Physiological Charge0
Formal Charge0
Refractivity41.09 m³·mol⁻¹
Polarizability14.82

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