Ortho-vanillin

Chembox new
Name = Ortho-Vanillin
ImageFile = ortho vanillin.png ImageSize = 150px
IUPACName= 2-Hydroxy-3-methoxybenzaldehyde
OtherNames = o-vanillin
3-methoxysalicylaldehyde

CASNo= 148-53-8
ChemSpiderID = 21105848
Section2 = Chembox Properties
Formula = C₈H₈O₃
MolarMass = 152.15 g/mol
Appearance = Yellow, fibrous solid
MeltingPt = 40-42 °C (313-315 K)
BoilingPt = 265-266 °C (458-459 K)
Section7 = Chembox Hazards
ExternalMSDS = [http://msds.chem.ox.ac.uk/VA/o-vanillin.html External MSDS]
MainHazards = May cause irritation to skin,
eyes, and respiratory tract
FlashPt = >110 °C
RPhrases = R20 R21 R22 R36 R37 R38
SPhrases = S26 S36 S37 S39
OtherFunctn = aromatics
OtherCpds = Eugenol, Anisaldehyde, Phenol, Vanillin

"Ortho"-vanillin, "3-methoxysalicylaldehyde", or "2-hydroxy-3-methoxybenzaldehyde ", is an organic solid present in the extracts and essential oils of many plants. [ cite journal
author = Abou Zeid, A. H.; Sleem, A. A.
title = Natural and stress constituents from Spinacia oleracea L. leaves and their biological activities
journal = Bulletin of the Faculty of Pharmacy (Cairo University)
year = 2002
volume = 40
issue = 2
pages = 153–167] [ cite journal
author = Barbe, Jean-Christophe; Bertrand, Alain.
title = Quantitative analysis of volatile compounds stemming from oak wood. Application to the aging of wines in barrels
journal = Journal des Sciences et Techniques de la Tonnellerie
year = 1996
volume = 2
pages = 77–88] [cite journal
author = Brunke, E. J.; Hammerschmidt, F. J.; Schmaus, G.
title = Das etherische Öl von Santolina chamaecyparissus L. (Santolina chamaecyparissus essential oil)
journal = Parfümerie und Kosmetik
year =1992
volume = 73
issue =9
pages = 617–18, 623–4, 626, 628–30, 632, 634–7] Its functional groups include aldehyde, ether and phenol. "Ortho"-vanillin, a compound of the formula C₈H₈O₃, is distinctly different from its more prevalent isomer, vanillin. The "ortho"-" prefix refers the to position of the compound’s hydroxyl moiety, which is found in the "para-" position in vanillin.

"Ortho"-vanillin is a fibrous, light-yellow, crystalline solid. Unlike its better-known analogue, "o"-vanillin does not have the characteristic and intense odor of vanilla. Present in a variety of food products, it is not specifically sought after, and is therefore a less-commonly produced and encountered food additive.

History

Ortho-vanillin was first isolated, in 1876, by renowned German chemist Ferdinand Tiemann. [cite journal
author = Tiemann, Ferdinand
title = Ueber die der Coniferyl- und Vanillinreihe angehörigen Verbindungen (Coniferyl- and vanillin series-related compounds)
journal = Berichte der Deutschen Chemischen Gesellschaft
year = 1876
volume = 9
pages = 409–423
url = http://gallica.bnf.fr/ark:/12148/bpt6k90682n/f416.chemindefer
doi = 10.1002/cber.187600901133 ] By 1910, methods for its purification had been developed by Francis Noelting, who similarly demonstrated its versatility as a general synthetic precursor for a diverse array of compounds, such as the coumarins. [Noelting, Francis A. M. o-Hydroxy-m-methoxybenzaldehyde (Orthovanillin). Annales de Chimie et de Physique (1910), 19 476-550.]

By 1920, the compound began to show use as a dye for hides. [Gerngross, Otto. Dyeing hide with o-vanillin and o-protocatechualdehyde and the aldehyde tanning. Angewandte Chemie (1920), 33, I 136-8. ]

Biological properties

O-vanillin is harmful if ingested, irritating to eyes, skin and respiratory system, but has an unmistakable high LD₅₀ of 1330 mg/kg in mice. [http://msds.chem.ox.ac.uk/VA/o-vanillin.html]

It is a weak inhibitor of tyrosinase, [Kubo, Isao; Kinst-Hori, Ikuyo. Tyrosinase inhibitory activity of the olive oil flavor compounds. Journal of Agricultural and Food Chemistry (1999), 47(11), 4574-4578. ] and displays both antimutagenic and comutagenic properties in Escherichia Coli. [Watanabe, Kazuko; Ohta, Toshihiro; Shirasu, Yasuhiko. Enhancement and inhibition of mutation by o-vanillin in Escherichia coli. Mutation Research, DNA Repair (1989), 218(2), 105-9. ] However, its net effect makes it a “potent comutagen.” [Takahashi, Kazuhiko; Sekiguchi, Mutsuo; Kawazoe, Yutaka. A specific inhibition of induction of adaptive response by o-vanillin, a potent comutagen. Biochemical and Biophysical Research Communications (1989), 162(3), 1376-81.]

O-vanillin possesses moderate antifungal and antibacterial properties. [Leifertova, I.; Hejtmankova, N.; Hlava, H.; Kudrnacova, J.; Santavy, F. Antifungal and antibacterial effects of phenolic substances. A study of the relation between the biological activity and the constitution of the investigated compounds. Acta Universitatis Palackianae Olomucensis, Facultatis Medicae (1975), 74 83-101. ]

Uses

Today, most o-vanillin is used in the study of mutagenesis and as a synthetic precursor for pharmaceuticals.Fact|date=August 2008

Notes