Syringic acid

Base Information

• Chemical Name: Syringic acid
• CAS No.: 530-57-4
• Molecular Formula: C9H10O5
• Molecular Weight: 198.175
• Hs Code.: 29189090
• European Community (EC) Number: 208-486-8
• NSC Number: 2129
• UNII: E390O181H5
• DSSTox Substance ID: DTXSID0060191
• Nikkaji Number: J11.712I
• Wikipedia: Syringic_acid
• Wikidata: Q408428
• Metabolomics Workbench ID: 38012
• ChEMBL ID: CHEMBL1414
• Mol file: 530-57-4.mol

Synonyms:syringic acid;syringic acid Cu (+2) salt (1:1)

Chemical Property of Syringic acid

Chemical Property:

• Appearance/Colour: light brown powder
• Vapor Pressure: 1.96E-06mmHg at 25°C
• Melting Point: 205-209 °C(lit.)
• Refractive Index: 1.566
• Boiling Point: 379.5 °C at 760 mmHg
• PKA: 4.33±0.10(Predicted)
• Flash Point: 155 °C
• PSA: 75.99000
• Density: 1.335 g/cm³
• LogP: 1.10760
• Storage Temp.: Store below +30°C.
• Solubility.: DMSO (Slightly), Methanol (Slightly)
• Water Solubility.: 5780 mg/L (25 ºC)
• XLogP3: 1
• Hydrogen Bond Donor Count: 2
• Hydrogen Bond Acceptor Count: 5
• Rotatable Bond Count: 3
• Exact Mass: 198.05282342
• Heavy Atom Count: 14
• Complexity: 191

Purity/Quality:

99% ^*data from raw suppliers

Syringic acid ^*data from reagent suppliers

Safty Information:

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

MSDS Files:

Useful:

• Chemical Classes: Other Classes -> Benzoic Acid Derivatives
• Canonical SMILES: COC1=CC(=CC(=C1O)OC)C(=O)O
• Description: Syringic acid is a naturally occurring O-methylated phenolic acid that can be enzymatically degraded by some bacteria as a source of methane or methanol. It is also a component of phenolic extracts from various plants that have antioxidant and prooxidant activities. Syringic acid has been shown to inhibit aldose reductase (IC50 = 213 μg/ml), proteasome activity, and cancer cell proliferation. Phenolic extracts containing syringic acid have been shown to inhibit α-amylase and α-glucosidase activities and reduce lipid peroxidation in vitro.
• Uses: antiproliferative; antifungal Syringic Acid is used in biological studies for electron transfer from plant phenolates to carotenoid radical cations with antioxidant interaction entering the Marcus theory inverted region.

Technology Process of Syringic acid

There total 40 articles about Syringic 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: 93.0%

syringic alcohol (530-56-3) → 3,5-dimethoxy-4-hydroxybenzoic acid (530-57-4)

Guidance literature:

With oxygen; at 120 ℃; for 12h; Green chemistry;

DOI:10.1039/c8gc00223a

Reference yield: 78.0%

methyl 3,5-dimethoxy-4-methoxymethoxybenzoate → 3,5-dimethoxy-4-hydroxybenzoic acid (530-57-4) + methyl syringate (884-35-5)

Guidance literature:

With ethylene glycol; at 120 ℃; for 1h;

DOI:10.1016/j.tetlet.2004.08.035

Reference yield: 65.0%

3,5-dimethoxybenzoic acid (1132-21-4) → 3,5-dimethoxy-4-hydroxybenzoic acid (530-57-4)

Guidance literature:

With C₂₈H₄₆N₄O₁₀S₂; dihydrogen peroxide; acetic acid; iron(II) chloride; In water; acetonitrile; at 80 ℃; for 1h; regioselective reaction;

DOI:10.1126/science.abj0731

upstream raw materials:

1-methyl-4-nitrosobenzene

1-(4-hydroxy-3,5-dimethoxyphenyl)propane-1,2-dione

O-acetylsyringic acid

delphinidin chloride

Downstream raw materials:

4-benzoyloxy-3,5-dimethoxy-benzoyl chloride

4-benzyloxy-3,5-dimethoxy benzoic acid-3-(1,2,3-tri-tert-butoxycarbonyl-3-(2 mercaptoethyl)guanidino)propyl ester

2-(4-benzyloxy-3,5-dimethoxyphenyl)ethylamine

4-benzyloxy-3,5-dimethoxyphenylacetonitrile

Refernces

• 1、 -. "Polycarboxylated compounds and compositions containing same". Page/Page column 17-22. . Retrieved 2021/06/09.
• 2、 -. "Method for promoting iron-catalyzed oxidation of aromatic compound carbon - hydrogen bond to synthesize phenol by ligand". Paragraph 0072-0073; 0127. . Retrieved 2021/09/21.