ortho-Vanillin

ortho-Vanillin
IUPAC name 2-Hydroxy-3-methoxybenzaldehyde
Other names o-Vanillin 3-Methoxysalicylaldehyde
Identifiers
CAS number	148-53-8 Y
ChemSpider	21105848 Y
ChEMBL	CHEMBL13859 Y
Jmol-3D images	Image 1
SMILES Oc1c(cccc1OC)C=O
InChI InChI=1S/C8H8O3/c1-11-7-4-2-3-6(5-9)8(7)10/h2-5,10H,1H3 Y Key: JJVNINGBHGBWJH-UHFFFAOYSA-N Y
Properties
Molecular formula	C8H8O3
Molar mass	152.15 g/mol
Appearance	Yellow, fibrous solid
Melting point	40–42 °C (313–315 K)
Boiling point	265–266 °C (458–459 K)
Hazards
MSDS	External MSDS
R-phrases	R20 R21 R22 R36 R37 R38
S-phrases	S26 S36 S37 S39
Main hazards	May cause irritation to skin, eyes, and respiratory tract
Flash point	>110 °C
Y (verify) (what is: Y/N?) Except where noted otherwise, data are given for materials in their standard state (at 25 °C, 100 kPa)
Infobox references

ortho-Vanillin (2-Hydroxy-3-methoxybenzaldehyde) is an organic solid present in the extracts and essential oils of many plants.^[1][2][3] 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.^[4] 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.^[5]

By 1920, the compound began to show use as a dye for hides.^[6]

Biological properties

ortho-Vanillin is harmful if ingested, irritating to eyes, skin and respiratory system, but has an unmistakable high LD₅₀ of 1330 mg/kg in mice.^[7]

It is a weak inhibitor of tyrosinase,^[8] and displays both antimutagenic and comutagenic properties in Escherichia coli.^[9] However, its net effect makes it a “potent comutagen.”^[10]

ortho-Vanillin possesses moderate antifungal and antibacterial properties.^[11]

Uses

Today, most ortho-vanillin is used in the study of mutagenesis and as a synthetic precursor for pharmaceuticals.^{[citation needed]}

Notes

1. ^ Abou Zeid, A. H.; Sleem, A. A. (2002). "Natural and stress constituents from Spinacia oleracea L. leaves and their biological activities". Bulletin of the Faculty of Pharmacy (Cairo University) 40 (2): 153–167. 
2. ^ Barbe, Jean-Christophe; Bertrand, Alain. (1996). "Quantitative analysis of volatile compounds stemming from oak wood. Application to the aging of wines in barrels". Journal des Sciences et Techniques de la Tonnellerie 2: 77–88. 
3. ^ Brunke, E. J.; Hammerschmidt, F. J.; Schmaus, G. (1992). "Das etherische Öl von Santolina chamaecyparissus L. (Santolina chamaecyparissus essential oil)". Parfümerie und Kosmetik 73 (9): 617–618, 623–624, 626, 628–630, 632, 634–637. 
4. ^ Tiemann, Ferdinand (1876). "Ueber die der Coniferyl- und Vanillinreihe angehörigen Verbindungen (Coniferyl- and vanillin series-related compounds)". Berichte der Deutschen Chemischen Gesellschaft 9: 409–423. doi:10.1002/cber.187600901133. http://gallica.bnf.fr/ark:/12148/bpt6k90682n/f416.chemindefer. 
5. ^ Noelting, Francis A. M. o-Hydroxy-m-methoxybenzaldehyde (Orthovanillin). Annales de Chimie et de Physique (1910), 19, 476–550.
6. ^ Gerngross, Otto. Dyeing hide with o-vanillin and o-protocatechualdehyde and the aldehyde tanning. Angewandte Chemie (1920), 33 (44), 136–138.
7. ^ http://msds.chem.ox.ac.uk/VA/o-vanillin.html
8. ^ 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.
9. ^ Watanabe, Kazuko; Ohta, Toshihiro; Shirasu, Yasuhiko. Enhancement and inhibition of mutation by o-vanillin in Escherichia coli. Mutation Research, DNA Repair (1989), 218 (2), 105–109.
10. ^ 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), 1376–1381.
11. ^ 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.