Record Information |
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Version | 1.0 |
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Created at | 2020-03-18 23:21:44 UTC |
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Updated at | 2022-12-13 19:31:28 UTC |
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CannabisDB ID | CDB006148 |
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Secondary Accession Numbers | Not Available |
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Cannabis Compound Identification |
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Common Name | Vanillic acid |
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Description | Vanillic acid, also known as vanillate, belongs to the class of organic compounds known as m-methoxybenzoic acids and derivatives. These are benzoic acids in which the hydrogen atom at position 3 of the benzene ring is replaced by a methoxy group. Vanillic acid is an extremely weak basic (essentially neutral) compound (based on its pKa). Vanillic acid is a phenolic acid or chlorogenic acid that is an oxidized form of vanillin. Vanillic acid is also an intermediate in the production of vanillin from ferulic acid. It is found in some forms of vanilla and many other plant extracts. It is a flavouring and scent agent that produces a pleasant, creamy odour. Açaí oil is particularly rich in vanillic acid (1,616 ± 94 mg/kg). Vanillic acid is also found in wine and vinegar.Vanillic acid is a metabolic by-product of caffeic acid and is often found in the urine of humans who have consumed coffee, chocolate, tea, and vanilla-flavoured confectionary. Vanillic acid selectively and specifically inhibits 5'-nucleotidase activity (PMID: 16899266 ). Vanillic acid is also a microbial metabolite found in several bacterial genera including Amycolatopsis, Delftia, and Pseudomonas (PMID: 11152072 , 10543794 , 11728709 , 9579070 ). |
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Structure | |
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Synonyms | Value | Source |
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4-HYDROXY-3-methoxybenzoATE | ChEBI | 4-HYDROXY-3-methoxybenzoic acid | Generator | Vanillate | Generator | Vanillic acid | Generator |
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Chemical Formula | C8H7O4 |
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Average Molecular Weight | 167.14 |
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Monoisotopic Molecular Weight | 167.0344 |
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IUPAC Name | 4-hydroxy-3-methoxybenzoate |
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Traditional Name | 4-hydroxy-3-methoxybenzoate |
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CAS Registry Number | 6746-48-1 |
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SMILES | COC1=CC(=CC=C1O)C([O-])=O |
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InChI Identifier | InChI=1S/C8H8O4/c1-12-7-4-5(8(10)11)2-3-6(7)9/h2-4,9H,1H3,(H,10,11)/p-1 |
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InChI Key | WKOLLVMJNQIZCI-UHFFFAOYSA-M |
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Chemical Taxonomy |
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Description | Belongs to the class of organic compounds known as m-methoxybenzoic acids and derivatives. These are benzoic acids in which the hydrogen atom at position 3 of the benzene ring is replaced by a methoxy group. |
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Kingdom | Organic compounds |
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Super Class | Benzenoids |
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Class | Benzene and substituted derivatives |
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Sub Class | Benzoic acids and derivatives |
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Direct Parent | M-methoxybenzoic acids and derivatives |
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Alternative Parents | |
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Substituents | - M-methoxybenzoic acid or derivatives
- Hydroxybenzoic acid
- Methoxyphenol
- Benzoic acid
- Phenoxy compound
- Anisole
- Methoxybenzene
- Benzoyl
- Phenol ether
- 1-hydroxy-2-unsubstituted benzenoid
- Alkyl aryl ether
- Phenol
- Carboxylic acid derivative
- Carboxylic acid
- Ether
- Monocarboxylic acid or derivatives
- Organic oxygen compound
- Organic oxide
- Organooxygen compound
- Hydrocarbon derivative
- Organic anion
- Aromatic homomonocyclic compound
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Molecular Framework | Aromatic homomonocyclic compounds |
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External Descriptors | |
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Ontology |
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Role | Industrial application: |
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Physical Properties |
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State | Solid |
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Experimental Properties | Property | Value | Reference |
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Melting Point | 210 - 213 °C | Wikipedia | Boiling Point | Not Available | Not Available | Water Solubility | Not Available | Not Available | logP | Not Available | Not Available |
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Predicted Properties | [] |
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Spectra |
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EI-MS/GC-MS | Not Available |
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MS/MS | Type | Description | Splash Key | View |
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Predicted MS/MS | Predicted LC-MS/MS Spectrum - 10V, Positive | splash10-014i-0900000000-35ba9477c2a80f8e5c53 | 2017-07-25 | View Spectrum | Predicted MS/MS | Predicted LC-MS/MS Spectrum - 20V, Positive | splash10-0aor-0900000000-eb2178b1865054dab1ce | 2017-07-25 | View Spectrum | Predicted MS/MS | Predicted LC-MS/MS Spectrum - 40V, Positive | splash10-052u-7900000000-dbf28dfc72f92a18a175 | 2017-07-25 | View Spectrum | Predicted MS/MS | Predicted LC-MS/MS Spectrum - 10V, Negative | splash10-014i-0900000000-626d449dddc4d2d47ec5 | 2017-07-26 | View Spectrum | Predicted MS/MS | Predicted LC-MS/MS Spectrum - 20V, Negative | splash10-014i-0900000000-6a319e19fb40b9ad2b59 | 2017-07-26 | View Spectrum | Predicted MS/MS | Predicted LC-MS/MS Spectrum - 40V, Negative | splash10-0a4l-9600000000-3f1b035788ad593819b9 | 2017-07-26 | View Spectrum |
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NMR | Not Available |
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Pathways |
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Pathways | Not Available |
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Protein Targets |
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Enzymes | |
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Transporters | Not Available |
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Metal Bindings | |
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Receptors | Not Available |
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Transcriptional Factors | Not Available |
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Concentrations Data |
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Alien Dawg | Detected and Quantified | 0.0063 mg/g dry wt | | details | Gabriola | Detected and Quantified | 0.0184 mg/g dry wt | | details | Island Honey | Detected and Quantified | 0.00485 mg/g dry wt | | details | Quadra | Detected and Quantified | 0.00965 mg/g dry wt | | details | Tangerine Dream | Detected and Quantified | 0.00742 mg/g dry wt | | details |
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External Links |
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HMDB ID | Not Available |
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DrugBank ID | DB02130 |
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Phenol Explorer Compound ID | Not Available |
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FoodDB ID | Not Available |
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KNApSAcK ID | Not Available |
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Chemspider ID | Not Available |
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KEGG Compound ID | Not Available |
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BioCyc ID | Not Available |
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BiGG ID | Not Available |
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Wikipedia Link | Vanillic acid |
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METLIN ID | Not Available |
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PubChem Compound | 23199 |
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PDB ID | Not Available |
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ChEBI ID | 16632 |
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References |
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General References | - Dhananjaya BL, Nataraju A, Rajesh R, Raghavendra Gowda CD, Sharath BK, Vishwanath BS, D'Souza CJ: Anticoagulant effect of Naja naja venom 5'nucleotidase: demonstration through the use of novel specific inhibitor, vanillic acid. Toxicon. 2006 Sep 15;48(4):411-21. doi: 10.1016/j.toxicon.2006.06.017. Epub 2006 Jul 7. [PubMed:16899266 ]
- Achterholt S, Priefert H, Steinbuchel A: Identification of Amycolatopsis sp. strain HR167 genes, involved in the bioconversion of ferulic acid to vanillin. Appl Microbiol Biotechnol. 2000 Dec;54(6):799-807. doi: 10.1007/s002530000431. [PubMed:11152072 ]
- Overhage J, Priefert H, Steinbuchel A: Biochemical and genetic analyses of ferulic acid catabolism in Pseudomonas sp. Strain HR199. Appl Environ Microbiol. 1999 Nov;65(11):4837-47. [PubMed:10543794 ]
- Plaggenborg R, Steinbuchel A, Priefert H: The coenzyme A-dependent, non-beta-oxidation pathway and not direct deacetylation is the major route for ferulic acid degradation in Delftia acidovorans. FEMS Microbiol Lett. 2001 Nov 27;205(1):9-16. doi: 10.1111/j.1574-6968.2001.tb10918.x. [PubMed:11728709 ]
- Venturi V, Zennaro F, Degrassi G, Okeke BC, Bruschi CV: Genetics of ferulic acid bioconversion to protocatechuic acid in plant-growth-promoting Pseudomonas putida WCS358. Microbiology. 1998 Apr;144 ( Pt 4):965-73. doi: 10.1099/00221287-144-4-965. [PubMed:9579070 ]
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