Vanillic Acid

Base Information

• Chemical Name: Vanillic Acid
• CAS No.: 121-34-6
• Molecular Formula: C8H8O4
• Molecular Weight: 168.149
• Hs Code.: 29189090
• European Community (EC) Number: 204-466-8
• NSC Number: 674322,3987
• UNII: GM8Q3JM2Y8
• DSSTox Substance ID: DTXSID6059522
• Nikkaji Number: J5.337F
• Wikipedia: Vanillic acid
• Wikidata: Q419672
• Metabolomics Workbench ID: 37271
• ChEMBL ID: CHEMBL120568
• Mol file: 121-34-6.mol

Synonyms:4 Hydroxy 3 methoxybenzoic Acid;4-Hydroxy-3-methoxybenzoic Acid;Acid, 4-Hydroxy-3-methoxybenzoic;Acid, p-Hydroxy-m-methoxy-benzoic;Acid, Vanillic;p Hydroxy m methoxy benzoic Acid;p-Hydroxy-m-methoxy-benzoic Acid;Vanillic Acid

Chemical Property of Vanillic Acid

Chemical Property:

• Appearance/Colour: white odourless crystals or powder
• Vapor Pressure: 1.32E-05mmHg at 25°C
• Melting Point: 208-210 ºC
• Refractive Index: Health: 1; Flammability: 0; Reactivity: 0
• Boiling Point: 353.4 ºC at 760 mmHg
• PKA: pKa 4.53(H2O t = 25 c = 0.016–0.001) (Uncertain)
• Flash Point: 149.4 ºC
• PSA: 66.76000
• Density: 1.351 g/cm³
• LogP: 1.09900
• Storage Temp.: Store below +30°C.
• Solubility.: Acetonitrile (Slightly), Aqueous Base (Slightly), DMSO (Slightly), Methanol (Slightly）
• Water Solubility.: Soluble in water, alcohol and ether.
• XLogP3: 1.4
• Hydrogen Bond Donor Count: 2
• Hydrogen Bond Acceptor Count: 4
• Rotatable Bond Count: 2
• Exact Mass: 168.04225873
• Heavy Atom Count: 12
• Complexity: 168

Purity/Quality:

99% ^*data from raw suppliers

Vanillic acid ^*data from reagent suppliers

Safty Information:

• Pictogram(s): Xi
• Hazard Codes: Xi
• Statements: 36/37/38
• Safety Statements: 37/39-26-36

MSDS Files:

SDS file from LookChem

Total 1 MSDS from other Authors

Useful:

• Chemical Classes: Biological Agents -> Plant Oils and Extracts
• Canonical SMILES: COC1=C(C=CC(=C1)C(=O)O)O
• Recent ClinicalTrials: To Evaluate the Efficacy and Safety in Patients With Dyslipidemia and Hypertension
• Description: Vanillic acid is a dihydroxybenzoic acid that can be used as a flavoring agent. As an oxidized form of vanillin, it is the intermediate product during the two-step bioconversion process from ferulic acid to vanillin. It exists in high amount in the root of Angelica sinenisis, which is a plant used in traditional Chinese medicine. It also exists in acal oil, argan oil as well as wine and vinegar. It can be used in the synthesis of the analeptic drug etamivan, modecainide, brovanexine, vanitiolide, and vanyldisulfamide. It can be manufactured through the oxidation of vanillin to the carboxylic acid.
• Uses: Vanillin, a compound widely used in foods, beverages, cosmetics and drugs, has been reported to exhibit multifunctional effects such as antimutagenic, antiangiogenetic, anti-colitis, anti-sickling, an d antianalgesic effects. However, results of studies on the antioxidant activity of vanillin are not consistent. A flavoring agent. Vanillic acid is used as a flavoring agent in food. It acts as an intermediate in the production of vanillin from ferulic acid. Further, it is used in wine and vinegar.

Technology Process of Vanillic Acid

There total 206 articles about Vanillic Acid which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield: 11.0%

2-(4-(1,3-dihydroxy-2-(4-methoxyphenoxy)propyl)-2-methoxyphenoxy)-1-(3,4-dimethoxyphenyl)propane-1,3-diol → coniferaldehyde (20649-42-7,458-36-6) + 3-methoxy-4-hydroxybenzoic acid (121-34-6) + vanillin (121-33-5,8014-42-4) + 4-methoxy-phenol (150-76-5) + Veratric acid (93-07-2)

Guidance literature:

With oxygen; sodium t-butanolate; In tert-butyl alcohol; at 30 ℃; for 16h; under 760.051 Torr; chemoselective reaction; Green chemistry;

DOI:10.1039/c8gc01886c

Reference yield:

C14H12FNO2 (3382-69-2,1799917-17-1) → 3-methoxy-4-hydroxybenzoic acid (121-34-6) + bis-(4-fluorophenyl)diazene (332-07-0,51788-93-3,51789-00-5)

Guidance literature:

With potassium bromate; sulfuric acid; mercury(II) diacetate; In water; at 39.84 ℃; Kinetics;

DOI:10.1016/j.jics.2021.100233

Reference yield:

6’’’-vanilloylspinosin (1343403-87-1) → D-glucose (50-99-7) + 3-methoxy-4-hydroxybenzoic acid (121-34-6) + swertisin (6991-10-2)

Guidance literature:

With hydrogenchloride; In water; at 100 ℃; for 2h;

DOI:10.1007/s10600-011-9936-y

upstream raw materials:

3-(4-hydroxy-3-methoxyphenyl)acrylic acid

4-acetoxy-3-methoxybenzoic acid

3-methoxy-4-hydroxybenzonitrile

1-methyl-4-nitrosobenzene

Downstream raw materials:

4-(2-hydroxyethoxyl)-3-methoxybenzoic acid

4,4’-(pentane-1,5-diylbis(oxy))bis(3-methoxybenzoic acid)

4-hydroxy-3-methoxy-benzoic acid isobutyl ester

3-formyl-4-hydroxy-5-methoxybenzoic acid

Refernces

• 1、 Schuerch. "-". . p. 2293. Retrieved 1948.
• 2、 Gon?alves, Danielle R.,Manthey, John A.,Da Costa, Paulo I.,Rodrigues, Marilia C. M.,Cesar, Thais B.. "Analysis of Fluorescence Spectra of Citrus Polymethoxylated Flavones and Their Incorporation into Mammalian Cells". . p. 7531 - 7541. Retrieved 2018.
• 3、 Kupchan,S.M. et al.. "". . p. 5756 - 5758. Retrieved 1970.
• 4、 Elbermawi, Ahmed,Halim, Ahmed F.,Mansour, El-Sayed S.,Ahmad, Kadria F.,Ashour, Ahmed,Amen, Yhiya,Shimizu, Kuniyoshi. "A new glucoside with a potent α-glucosidase inhibitory activity from Lycium schweinfurthii". . p. 976 - 983. Retrieved 2021.
• 5、 Sridevi,Ramaswamy. "A dual-phase oscillatory behavior in Belousov Zhabotinsky system with vanillin as the substrate". . p. 201 - 206. Retrieved 1998.
• 6、 Hiremath,Kiran,Nandibewoor. "Oxidation of vanillin by diperiodatocuprate(III) in aqueous alkaline medium: A kinetic and mechanistic study by stopped flow technique". . p. 236 - 244. Retrieved 2007.
• 7、 Colovina et al.. "". . . Retrieved 1978.
• 8、 Englis,Manchester. "-". . p. 591. Retrieved 1949.
• 9、 Wu, Yi,He, Feng,Pan, Qin,Shi, Yao,Min, Zhida,Liang, Jingyu. "C-glucosyl flavones from the seeds of ziziphus jujuba var. spinosa". . p. 369 - 372. Retrieved 2011.
• 10、 Thea, Sergio,Cevasco, Giorgio,Guanti, Giuseppe,Kashefi-Naini, Nasrin,Willams, Andrew. "Reactivity in the Para Oxo Ketene Route of Ester Hydrolysis. The Effect of Internal Nucleophilicity and the Irrelevance of B Strain". . p. 1867 - 1872. Retrieved 1985.