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 97% ^*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

ethyl vanillate

propyl vanillate

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

Refernces

Selective production of bio-based aromatics by aerobic oxidation of native soft wood lignin in tetrabutylammonium hydroxide

10.1039/d0ra03420g

The research focuses on the efficient production of bio-based aromatics, specifically vanillin, through the aerobic oxidation of native soft wood lignin. The experiments utilized an aqueous solution of tetrabutylammonium hydroxide (Bu4NOH) to oxidize Japanese cedar wood flour at 120°C for 4 hours under oxygen, yielding vanillin at 23.2 wt% based on the Klason lignin content. This yield is comparable to the alkaline nitrobenzene oxidation method, a benchmark for lignin oxidation processes. The study suggests that vanillin formation primarily occurs through successive reactions: alkaline-catalyzed degradation of lignin's β-ether linkages to form a glycerol end group, oxidation of this end group by O2 to an aldehyde group, and subsequent release of vanillin. The research also indicates that Bu4NOH's performance in vanillin production is superior to simple alkalis like NaOH, due to Bu4NOH being a stronger base and the cation Bu4N+ suppressing the disproportionation of vanillin precursors. The analyses involved high-performance liquid chromatography (HPLC) and gas chromatography/mass spectrometry (GC/MS) to quantify the yields of vanillin, vanillic acid, and other products.