ortho-Vanillin
{{DISPLAYTITLE:ortho-Vanillin}}
{{chembox
| Verifiedfields = changed
| Watchedfields = changed
| verifiedrevid = 415883798
| Name = ortho-Vanillin
| ImageFile = Ortho-Vanillin.svg
| ImageSize = 150px
| PIN = 2-Hydroxy-3-methoxybenzaldehyde
| OtherNames = o-Vanillin
3-Methoxysalicylaldehyde
|Section1={{Chembox Identifiers
| CASNo_Ref = {{cascite|correct|CAS}}
| CASNo = 148-53-8
| ChEBI_Ref = {{ebicite|correct|EBI}}
| ChEBI = 78339
| ChEMBL_Ref = {{ebicite|correct|EBI}}
| ChEMBL = 13859
| ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}}
| ChemSpiderID = 21105848
| PubChem = 8991
| UNII_Ref = {{fdacite|correct|FDA}}
| UNII = 008LR748FI
| StdInChI_Ref = {{stdinchicite|correct|chemspider}}
| StdInChI = 1S/C8H8O3/c1-11-7-4-2-3-6(5-9)8(7)10/h2-5,10H,1H3
| StdInChIKey_Ref = {{stdinchicite|correct|chemspider}}
| StdInChIKey = JJVNINGBHGBWJH-UHFFFAOYSA-N
| SMILES = Oc1c(cccc1OC)C=O
}}
|Section2={{Chembox Properties
| Formula = C8H8O3
| MolarMass = 152.15 g/mol
| Appearance = Yellow, fibrous solid
| Density = 1.231 g/mL
| MeltingPtC = 40 to 42
| MeltingPt_notes =
| BoilingPtC = 265 to 266
| BoilingPt_notes =
}}
|Section7={{Chembox Hazards
| ExternalSDS = [http://msds.chem.ox.ac.uk/VA/o-vanillin.html External MSDS]
| MainHazards = May cause irritation to skin,
eyes, and respiratory tract
| FlashPt = >
| FlashPtC = 110
| GHSPictograms = {{GHS05}}{{GHS07}}
| GHSSignalWord = Danger
| HPhrases = {{H-phrases|302|315|317|318|319|335}}
| PPhrases = {{P-phrases|261|264|270|271|272|280|301+312|302+352|304+340|305+351+338|310|312|321|330|332+313|333+313|337+313|362|363|403+233|405|501}}
}}
|Section8={{Chembox Related
| OtherFunction_label = aromatics
| OtherFunction =
| OtherCompounds = Eugenol, Anisaldehyde, Phenol, Vanillin
}}
}}
ortho-Vanillin (2-hydroxy-3-methoxybenzaldehyde) is an organic solid present in the extracts and essential oils of many plants.{{cite journal
|author1=Abou Zeid, A. H. |author2=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
{{cite journal
|author1=Barbe, Jean-Christophe |author2=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
{{cite journal
|author1=Brunke, E. J. |author2=Hammerschmidt, F. J. |author3=Schmaus, G. | title = Das etherische Öl von Santolina chamaecyparissus L. |trans-title= The essential oil of Santolina chamaecyparissus L.
| journal = Parfümerie und Kosmetik
| year = 1992
| volume = 73
| issue = 9
| pages = 617–637}} Its functional groups include aldehyde, ether and phenol. ortho-Vanillin, a compound of the formula C8H8O3, is distinctly different from its more prevalent isomer, para-vanillin. The "ortho-" prefix refers to the 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. 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 |trans-title=On 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.{{cite journal|author=Noelting, Francis A. M. |title=o-Hydroxy-m-methoxybenzaldehyde (Orthovanillin) |journal=Annales de Chimie et de Physique |date=1910 |volume=19 |pages=476–550}}
By 1920, the compound began to show use as a dye for hides.{{cite journal|author=Gerngross, Otto |title=Dyeing hide with o-vanillin and o-protocatechualdehyde and aldehyde tanning |journal=Angewandte Chemie |date=1920 |volume=33 |issue=44 |pages=136–138|doi=10.1002/ange.19200334403 |url=https://zenodo.org/record/1424480 }}
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.http://msds.chem.ox.ac.uk/VA/o-vanillin.html {{Dead link|date=August 2022}}
It is a weak inhibitor of tyrosinase,{{cite journal|author1=Kubo, Isao |author2=Kinst-Hori, Ikuyo |title=Tyrosinase inhibitory activity of the olive oil flavor compounds |journal=Journal of Agricultural and Food Chemistry |date=1999 |volume=47 |issue=11 |pages=4574–4578 |doi=10.1021/jf990165v |pmid=10552852 }} and displays both antimutagenic and comutagenic properties in Escherichia coli.{{cite journal|author1=Watanabe, Kazuko |author2=Ohta, Toshihiro |author3=Shirasu, Yasuhiko |title=Enhancement and inhibition of mutation by o-vanillin in Escherichia coli |journal=Mutation Research/DNA Repair |date=1989 |volume=218 |issue=2 |pages=105–9 |doi=10.1016/0921-8777(89)90016-5 |pmid=2671704 }} However, its net effect makes it a “potent comutagen”.{{cite journal|author1=Takahashi, Kazuhiko |author2=Sekiguchi, Mutsuo |author3=Kawazoe, Yutaka |title=A specific inhibition of induction of adaptive response by o-vanillin, a potent comutagen |journal=Biochemical and Biophysical Research Communications |date=1989 |volume=162 |issue=3 |pages=1376–81 |doi=10.1016/0006-291X(89)90826-7 |pmid=2669748 }}
ortho-Vanillin possesses moderate antifungal and antibacterial properties.{{cite journal|author1=Leifertova, I. |author2=Hejtmankova, N. |author3=Hlava, H. |author4=Kudrnacova, J. |author5=Santavy, F. |title=Antifungal and antibacterial effects of phenolic substances. A study of the relation between the biological activity and the constitution of the investigated compounds |journal=Acta Universitatis Palackianae Olomucensis, Facultatis Medicae |date=1975 |volume=74 |pages=83–101}}
Uses
Today, most ortho-vanillin is used in the study of mutagenesis and as a synthetic precursor for pharmaceuticals, for example, benafentrine{{cite journal|last1=Press|first1=Jeffery B.|last2=Bandurco|first2=Victor T.|last3=Wong|first3=Elizabeth M.|last4=Hajos|first4=Zoltan G.|last5=Kanojia|first5=Ramesh M.|last6=Mallory|first6=Robert A.|last7=Deegan|first7=Edward G.|last8=Mcnally|first8=James J.|last9=Roberts|first9=Jerry R.|last10=Cotter|first10=Mary Lou|last11=Graden|first11=David W.|last12=Lloyd|first12=John R.|title=Synthesis of 5,6-dimethoxyquinazolin-2(1H)-ones|journal=Journal of Heterocyclic Chemistry|volume=23|issue=6|year=1986|pages=1821–1828|issn=0022-152X|doi=10.1002/jhet.5570230643}} and an antiandrogen compound called Pentomone.
See also
Notes
{{reflist}}
{{DEFAULTSORT:Vanillin, ortho-}}