Vanillic acid

Structural formula
General
Surname	Vanillic acid
other names	4-hydroxy-3-methoxybenzoic acid
Molecular formula	C 8 H 8 O 4
Brief description	yellowish, odorless solid
External identifiers / databases
EC number	204-466-8
ECHA InfoCard	100.004.061
PubChem	8468
ChemSpider	8155
DrugBank	DB02130
Wikidata	Q419672
properties
Molar mass	168.15 g mol −1
Physical state	firmly
Melting point	208-210 ° C
pK s value	4.53 (25 ° C)
solubility	poorly soluble in water
safety instructions
GHS labeling of hazardous substances	no GHS pictograms
	no GHS pictograms
H and P phrases	H: no H-phrases
	P: no P-phrases
	As far as possible and customary, SI units are used. Unless otherwise noted, the data given apply to standard conditions .

Vanillic acid ( 4-hydroxy-3-methoxybenzoic acid ) is an organic chemical compound and belongs to the group of phenolic acids . The substance is structurally derived from both benzoic acid and guaiacol ( o -methoxyphenol).

Occurrence

There are traces of vanillic acid in various types of fruit such as strawberries , alcoholic beverages such as red wine and as a breakdown product of adrenaline and noradrenaline in the urine. The highest known occurrence of vanillic acid in plants is in the root of Angelica sinensis , commonly "dong quai", "dang gui" or "female ginseng" (Chinese: 当归), a Chinese herb used in traditional Chinese medicine becomes.

Extraction and presentation

Vanillin formed during lignin degradation by wood-destroying fungi or in the oxidation of vanillin .

Biochemically, vanillic acid is an intermediate in the production of vanillin from ferulic acid .

properties

Both vanillin and vanillic acid have antimicrobial properties. Vanillic acid inhibits the yeast Saccharomyces cerevisiae and the growth of Zymomonas mobilis . In vitro , vanillic acid inhibits the growth of Proteus mirabilis in urine and the kidney stones produced by the germ .

Web links

Entry to vanillic acid . In: P. J. Linstrom, W. G. Mallard (Eds.): NIST Chemistry WebBook, NIST Standard Reference Database Number 69 . National Institute of Standards and Technology , Gaithersburg MD, accessed December 14, 2012.

Individual evidence

↑ ^a ^b ^c ^d Entry on vanillic acid in the GESTIS substance database of the IFA , accessed on December 11, 2012(JavaScript required) .
^ D'Ans-Lax, paperback for chemists and physicists , 3rd edition, volume 1, Springer-Verlag, 1967.
^ W. Ternes: Food Lexicon.
↑ A. Hohmann: Lexicon of Dental Technology.
↑ Dr. Duke's Phytochemical and Ethnobotanical Databases: Vanillic Acid , accessed February 5, 2018.
↑ Laurence Lesage-Meessen, Michel Delattre, Mireille Haon, Jean-François Thibault, Benoit Colonna Ceccaldi, Pascal Brunerie, Marcel Asther: A two-step bioconversion process for vanillin production from ferulic acid combining “Aspergillus niger” and “Pycnoporus cinnabarinus” . In: J. Biotechnol. , 1996 , 50 (2-3), pp. 107-113 ( doi : 10.1016 / 0168-1656 (96) 01552-0 ; PMID 8987621 ).
↑ Claudio Civolani, Paolo Barghini, Anna Rita Roncetti, Maurizio Ruzzi, Alma Schiesser: Bioconversion of Ferulic Acid into Vanillic Acid by Means of a Vanillate-Negative Mutant of "Pseudomonas fluorescens" Strain BF13 . In: Appl. Environ. Microbiol. , 2000 , 66 (6), pp. 2311-2317 ( doi : 10.1128 / AEM.66.6.2311-2317.2000 ; PMID 10831404 ; PMC 110519 (free full text)).
↑ Yvonne Kirsch: Antibacterial effect of selected natural substances on the growth of Listeria monocytogenes , diploma thesis, Bonn 2006 ( abstract ).
↑ Agnieszka Torzewska, Antoni Rozalski: Inhibition of crystallization Caused by Proteus mirabilis during the development of infectious urolithiasis by various phenolic substances . In: Microbiological Research , 2013 , S., ( doi : 10.1016 / j.micres.2013.09.020 ).

[GESTIS-1] Entry on vanillic acid in the GESTIS substance database of the IFA , accessed on December 11, 2012(JavaScript required) .

[2] D'Ans-Lax, paperback for chemists and physicists , 3rd edition, volume 1, Springer-Verlag, 1967.

[3] W. Ternes: Food Lexicon.

[4] A. Hohmann: Lexicon of Dental Technology.

[5] Dr. Duke's Phytochemical and Ethnobotanical Databases: Vanillic Acid , accessed February 5, 2018.

[pmid8987621-6] Laurence Lesage-Meessen, Michel Delattre, Mireille Haon, Jean-François Thibault, Benoit Colonna Ceccaldi, Pascal Brunerie, Marcel Asther: A two-step bioconversion process for vanillin production from ferulic acid combining “Aspergillus niger” and “Pycnoporus cinnabarinus” . In: J. Biotechnol. , 1996 , 50 (2-3), pp. 107-113 ( doi : 10.1016 / 0168-1656 (96) 01552-0 ; PMID 8987621 ).

[pmid10831404-7] Claudio Civolani, Paolo Barghini, Anna Rita Roncetti, Maurizio Ruzzi, Alma Schiesser: Bioconversion of Ferulic Acid into Vanillic Acid by Means of a Vanillate-Negative Mutant of "Pseudomonas fluorescens" Strain BF13 . In: Appl. Environ. Microbiol. , 2000 , 66 (6), pp. 2311-2317 ( doi : 10.1128 / AEM.66.6.2311-2317.2000 ; PMID 10831404 ; PMC 110519 (free full text)).

[8] Yvonne Kirsch: Antibacterial effect of selected natural substances on the growth of Listeria monocytogenes , diploma thesis, Bonn 2006 ( abstract ).

[DOI10.1016/j.micres.2013.09.020-9] Agnieszka Torzewska, Antoni Rozalski: Inhibition of crystallization Caused by Proteus mirabilis during the development of infectious urolithiasis by various phenolic substances . In: Microbiological Research , 2013 , S., ( doi : 10.1016 / j.micres.2013.09.020 ).