Acid Vanillique — Wikipedia

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Vanillic acid
Image illustrative de l’article Acide vanillique
Identification
UICPA name 4-hydroxy-3-methoxybenzoic acid
N O CAS 121-34-6
N O Echa 100.004.061
N O THIS 204-466-8
N O RTECS YW5300000
Pubchem 8468
SMILES
Inches
Appearance odorless yellowish powder [ first ]
Chemicals
Formula C 8 H 8 O 4 [Isomers]
Molar mass [ 3 ] 168,146 7 ± 0.008 2 g/mol
C 57,14 %, H 4,8 %, O 38,06 %,
p K a 4.53 To 25 °C [ 2 ]
Physical properties
T° fusion 208 To 210 °C [ first ]
Solubility slightly soluble in water [ first ]
Precautions
NFPA 704 [ 4 ]
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Symbole NFPA 704.

Directive 67/548/EEC [ 4 ]
Irritant
Xi
Ecotoxicology
DL 50 > 2 691 mg · kg -first (Mouse, I.P.) [ 5 ]
LogP 1.43 [ first ]
IS units and CNTP , unless otherwise stated.
modifier Consultez la documentation du modèle

L’ vanillic acid or 4-hydroxy-3-methoxybenzoic acid is an aromatic compound of Formula C 8 H 8 O 4 , belonging to the family acids, more precisely hydroxybenzoic acids. It consists of a cycle of benzene substituted by a carboxyl group, a hydroxyl group and a handguns in hairs 1, 3 and 4, which makes it a vanilloid. It is an oxidized form of vanillin (4-hydroxy-3-methoxybenzaldehyde). It is also an intermediary in the production of vanillin from férulic acid [ 6 ] , [ 7 ] .

We find the largest amount of vanillic acid in the root of the angelica of China ( Angelica sinensis ) [ 8 ] , called “Danggui”, “Dong Quai” or “female ginseng” (当归 / 當歸 in Chinese), a grass from China, used in traditional Chinese medicine. There is also vanillic acid in strawberries or certain alcoholic beverages such as red wine [ 9 ] . It is also a metabolite of adrenaline and noradrenaline present in the urine [ ten ] . Vanillic acid also comes from the degradation of lignin by lignivorous mushrooms and the oxidation of vanillin.

Vanillic acid, like vanillin, has anti-microbial properties. Vanillic acid inhibits the yeast Saccharomyces cerevisiae and the growth of Zymomonas Mobilis [ 11 ] .

Secondary metabolites of vanillic acid are often used as aromas.

  1. ↑ A B C and D “Vanillic Acid” input in the chemical product database Achievement IFA (German organization responsible for occupational safety and health) ( German , English ), access on July 10, 2011 (Javascript required)
  2. ↑ D’Ans-Lax, paperback for chemists and physicists, 3rd edition, Volume 1, Springer-Verlag, 1967.
  3. ↑ Molar mass calculated after ‘ Atomic weights of the elements 2007 » , on www.chem.qmul.ac.uk .
  4. ↑ a et b Fiche alfa aesar , consulted on July 10, 2011
  5. ↑ Yakugaku Zasshi. Journal of pharmacy. Vol. 104, pg. 793, 1984
  6. ↑ (in) Leseage-Messes L, DELTATTY M, HABAULT JF, CECCALDI BC, Brunerie P, Astherm ‘ A two-step bioconversion process for vanillin production from ferulic acid combining Aspergillus niger and Pycnoporus cinnabarinus » , J. Biotechnol. , vol. 50, n you 2–3, , p. 107–13 (PMID  8987621, DOI  10.1016/0168-1656(96)01552-0)
  7. ↑ (in) Civolaniats, Barghini pie Noncetti Ar, Ruzziz M, Squesser a, ‘ Bioconversion of ferulic acid into vanillic acid by means of a vanillate-negative mutant of Pseudomonas fluorescens strain BF13 » , Appl. Environ. Microbiol. , vol. 66, n O 6, , p. 2311–7 (PMID  10831404, PMCID  110519, DOI  10.1128/AEM.66.6.2311-2317.2000)
  8. ↑ (in) Duke, me, Handbook of phytochemical constituents of GRAS herbs and other economic plants , Boca Raton, CRC Press, 999 edition, (ISBN  978-0-8493-3865-6 , LCCN 00049359, read online )
  9. ↑ W. Ternes: Food Exexicon.
  10. ↑ A. Hohmann: Lexicon of dental technology.
  11. ↑ Yvonne Kirsch: Antibacterial effect of selected natural substances on the growth of Listeria Monocytogenes, diploma thesis, Bonn 2006; Abstract .

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