530-57-4

Basic information

• Product Name: Syringic acid
• Synonyms: RARECHEM AL BE 0102;SYRINGIC ACID;4-HYDROXY-3,5-DIMETHOXYBENZOIC ACID / SYRINGIC ACID;Syringlicacid;Syringic acid,97%;4-Hydroxy-3,5-dimethoxybenzoic acid ,98%;Syringic acid, 97% 10GR;Gallic Acid 3,5-Dimethyl Ether 4-Hydroxy-3,5-dimethoxybenzoic Acid
• CAS NO: 530-57-4
• Molecular Formula: C₉H₁₀O₅
• Molecular Weight: 198.17
• EINECS: 208-486-8
• Product Categories: Aromatic Carboxylic Acids, Amides, Anilides, Anhydrides & Salts;Benzoic acid;Organic acids;Acids & Esters;Anisoles, Alkyloxy Compounds & Phenylacetates;Phenols;Pharmaceutical Intermediate;chemical reagent;phytochemical;reference standards from Chinese medicinal herbs (TCM).;standardized herbal extract;Inhibitors;FINE Chemical & INTERMEDIATES
• Mol File: 530-57-4.mol

Chemical Properties

• Melting Point: 205-209 °C(lit.)
• Boiling Point: 192-193°C 14mm
• Flash Point: 192-193°C/14mm
• Appearance: Grayish-beige to light brown/Powder
• Density: 1.2539 (rough estimate)
• Vapor Pressure: 1.96E-06mmHg at 25°C
• Refractive Index: 1.4570 (estimate)
• Storage Temp.: Store below +30°C.
• Solubility: DMSO (Slightly), Methanol (Slightly)
• PKA: 4.33±0.10(Predicted)
• Water Solubility: 5780 mg/L (25 ºC)
• Stability: Stable. Incompatible with strong bases, strong oxidizing agents.
• BRN: 2115262
• CAS DataBase Reference: Syringic acid(CAS DataBase Reference)
• NIST Chemistry Reference: Syringic acid(530-57-4)
• EPA Substance Registry System: Syringic acid(530-57-4)

Safety Data

• Hazard Codes: Xi
• Statements: 36/37/38
• Safety Statements: 26-36-37/39
• WGK Germany: 3
• RTECS: DH2090000
• TSCA: Yes
• Hazardous Substances Data: 530-57-4(Hazardous Substances Data)

Usage

Uses

1. Used in Anticancer Applications:
Syringic acid is used as an antiproliferative agent for its ability to inhibit cancer cell proliferation, making it a potential candidate in the development of cancer treatments.
2. Used in Antifungal Applications:
Syringic acid is utilized as an antifungal agent, providing protection against fungal infections due to its antimicrobial properties.
3. Used in Biological Studies:
Syringic acid is employed in biological studies for electron transfer from plant phenolates to carotenoid radical cations, with antioxidant interaction entering the Marcus theory inverted region. This application aids in understanding the complex interactions between plant phenolates and carotenoids, which can have implications in various biological processes.
4. Used in Enzymatic Degradation:
Syringic acid is used as a substrate for enzymatic degradation by certain bacteria, which can convert it into methane or methanol. This process has potential applications in bioenergy production and waste management.
5. Used in Phenolic Extracts:
Syringic acid is a component of phenolic extracts from various plants, which are used for their antioxidant and prooxidant activities. These extracts have potential applications in the pharmaceutical, cosmetic, and food industries, where their antioxidant properties can be harnessed for various health and preservation purposes.
6. Used in Inhibiting Enzyme Activities:
Syringic acid is used to inhibit α-amylase and α-glucosidase activities, which can help in managing blood sugar levels and reducing the risk of diabetes-related complications. This application can be particularly useful in the development of drugs and supplements for diabetes management.
7. Used in Reducing Lipid Peroxidation:
Syringic acid is utilized to reduce lipid peroxidation in vitro, which can help in preventing cellular damage and maintaining overall health. This application can be beneficial in the development of antioxidants and other products aimed at promoting health and wellness.

Purification Methods

Recrystallise syringic acid from H2O using charcoal [Bogert & Coyne J Am Chem Soc 51 571 1929, Anderson & Nabenhauer J Am Chem Soc 48 3001 1926.] The methyl ester has m 107o (from MeOH), the 4-acetyl derivative has m 190o and the 4-benzoyl derivative has m 229-232o. [Hahn & Wassmuth Chem Ber 67 2050 1934, UV: Lemon J Am Chem Soc 69 2998 1947 and Pearl & Beyer J Am Chem Soc 72 1743 1950, Beilstein 10 IV 1995.]

InChI:InChI=1/C9H10O5/c1-13-6-3-5(9(11)12)4-7(14-2)8(6)10/h3-4,10H,1-2H3,(H,11,12)

Upstream product

• 7647-01-0 hydrogenchloride 
• 118-41-2 Eudesmic acid 
• 7664-93-9 sulfuric acid 
• 10035-10-6 hydrogen bromide 
• 623-11-0 1-methyl-4-nitrosobenzene 
• 6925-65-1 1-(4-hydroxy-3,5-dimethoxyphenyl)propane-1,2-dione 
• 1132-21-4 3,5-dimethoxybenzoic acid 
• 530-56-3 syringic alcohol 
• 92409-34-2 1-(4-hydroxy-3,5-dimethoxyphenyl)-2-(2'-methoxyphenoxy)-1,3-propanediol 
• 18470-06-9 malvidin 3-O-glucoside 
• 643-84-5 malvidin chloride 
• 186581-53-3 diazomethane 
• 1359001-19-6 4-O-(3,5-di-O-methylgalloyl)bergenin 
• 134-96-3 syringic aldehyde 

Downstream Products

• 99463-09-9 (5-formylfuran-2-yl)methyl 4-<(5'-formylfuran-2'-yl)methoxy>-3,5-dimethoxybenzoate 
• 66922-68-7 4-allyloxy-3,5-dimethoxyacetophenone 
• 954-85-8 4-Allyloxy-3.5-dimethoxy-benzoylchlorid 
• 75332-45-5 ethyl 3,5-dimethoxy-4-ethoxybenzoate 
• 67-56-1 methanol 
• 6318-20-3 O-acetylsyringic acid 
• 14588-60-4 4-(benzyloxy)-3,5-dimethoxybenzoic acid 
• 935527-16-5 2-propynyl 4-(2-propynyloxy)-3,5-dimethoxybenzoate 
• 69114-12-1 1-(4-ethoxycarbonyl-2,6-dimethoxy)phenoxy-2,3-epoxy-propane 
• 40638-65-1 4-acetoxy-3,5-dimethoxy-2-nitrobenzoic acid 
• 866998-57-4 4-hydroxy-3,5-dimethoxy-2-nitro-benzoic acid 
• 860755-14-2 2-amino-4-hydroxy-3,5-dimethoxy-benzoic acid methyl ester 
• 146715-70-0 4-Amino-pyrogallol-1.3-dimethylaether 
• 860743-02-8 2-(4-acetoxy-3,5-dimethoxy-benzoyl)-3-oxo-butyric acid ethyl ester 

Relevant articles and documents

Interaction of anthocyanins and anthocyanidins with α-hydroxyethyl radicals

The products of interaction of anthocyanins and anthocyanidins with α-hydroxyethyl radicals have been studied using spectrophotometry and liquid chromatography-mass spectrometry. It has been shown that anthocyanins and anthocyanidins oxidize the hydroxyethyl radical. The anthocyanin transformation products are oxidized with oxygen to the parent anthocyanins. Anthocyanidins irreversibly react to form the corresponding hydroxybenzoic acid and presumably 4-(2-hydroxyethyl)resorcinol.

Iron-catalyzed arene C-H hydroxylation

The sustainable, undirected, and selective catalytic hydroxylation of arenes remains an ongoing research challenge because of the relative inertness of aryl carbon-hydrogen bonds, the higher reactivity of the phenolic products leading to over-oxidized by-products, and the frequently insufficient regioselectivity. We report that iron coordinated by a bioinspired L-cystine-derived ligand can catalyze undirected arene carbon-hydrogen hydroxylation with hydrogen peroxide as the terminal oxidant. The reaction is distinguished by its broad substrate scope, excellent selectivity, and good yields, and it showcases compatibility with oxidation-sensitive functional groups, such as alcohols, polyphenols, aldehydes, and even a boronic acid. This method is well suited for the synthesis of polyphenols through multiple carbon-hydrogen hydroxylations, as well as the late-stage functionalization of natural products and drug molecules.

Method for promoting iron-catalyzed oxidation of aromatic compound carbon - hydrogen bond to synthesize phenol by ligand

The method comprises the following steps: iron is used as - a catalyst metal; a sulfur-containing amino acid or cystine-derived dipeptide is a ligand; and under the common action of hydrogen peroxide as an oxidizing agent, an aromatic compound is synthesized to prepare a phenol. Under the action of an acid as an accelerant and hydrogen peroxide as an oxidizing agent, the aryl carbon - hydrogen bond is directly hydroxylated to form a phenolic compound, and the method for preparing the phenol by the catalytic oxidation reaction has a plurality of advantages. The reaction raw materials, the oxidant and the promoter are wide in source, low in price, environment-friendly and good in stability. The aromatic compound carbon - hydrogen bonds directly participate in the reaction to react in one step to form phenol. The reaction condition is mild, the functional group compatibility and the application range are wide. The reaction selectivity is good; under the optimized reaction conditions, the target product separation yield can reach 85%.

Polycarboxylated compounds and compositions containing same

Methods of selectively modifying lignin, polycarboxylated products thereof, and methods of deriving aromatic compounds therefrom. The methods comprise electrochemically oxidizing lignin using stable nitroxyl radicals to selectively oxidize primary hydroxyls on β-O-4 phenylpropanoid units to corresponding carboxylic acids while leaving the secondary hydroxyls unchanged. The oxidation results in polycarboxylated lignin in the form of a polymeric β-hydroxy acid. The polymeric β-hydroxy acid has a high loading of carboxylic acid and can be isolated in acid form, deprotonated, and/or converted to a salt. The β-hydroxy acid, anion, or salt can also be subjected to acidolysis to generate various aromatic monomers or oligomers. The initial oxidation of lignin to the polycarboxylated form renders the lignin more susceptible to acidolysis and thereby enhances the yield of aromatic monomers and oligomers obtained through acidolysis.

Terpenoid and phenolic constituents from the roots of Ilex pubescens

Five new metabolites, including two monoterpene glycosides Pubescenosides L–M (1–2) and three phenolic glycosides, Pubescenosides N-P (3–5), along with nineteen known ones, including liganoids, hemiterpenoids and caffeoylquinic acid derivates, were isolated from the roots of Ilex pubescens. Their structures were elucidated from extensive spectroscopic analysis, including 1D and 2D NMR experiments. This study is the first to report monoterpene glycosides with β-pinene aglycone in Aquifoliaceae. Nine of these compounds were evaluated in vitro for their anti-platelet aggregation activities. Among them, compounds 3 and 4 showed moderate inhibitory activities on ADP-induced blood platelet aggregation [inhibition (%): 32.3 and 33.6, respectively] as compared to aspirin.

Transition-metal-free conversion of lignin model compounds to high-value aromatics: Scope and chemoselectivity

An efficient and straightforward reaction protocol for the conversion of lignin model compounds was developed based on a simple system consisting of a base, oxygen, and a green solvent under mild conditions in the absence of metals. This protocol was successfully applied to the cleavage of both 'β-O-4' dimeric and trimeric compounds, and a controlled selective degradation was achieved depending on the bond type. The feasibility of this method to provide aromatic compounds in high yields from lignin by a sequential oxidative dehomologation reaction was clearly demonstrated.

Bis(methoxypropyl) ether-promoted oxidation of aromatic alcohols into aromatic carboxylic acids and aromatic ketones with O2 under metal- and base-free conditions

We describe an eco-friendly, practical and operationally simple procedure for the bis(methoxypropyl) ether-promoted oxidation of aromatic alcohols into aromatic carboxylic acids and aromatic ketones with atmospheric dioxygen as the sole oxidant. This chemical process is clean with high conversion and good selectivity, and an external initiator, catalyst, additive and base are not required. The virtue of this reaction is highlighted by its easily available and economical raw materials and excellent functional group tolerance (acid-, base- and oxidant-labile groups).

Ruticarpsides A–C, three new ester glycosides from the fruits of Tetradium ruticarpum

In the course of our ongoing phytochemical investigation on the n-butanol extract of the fruits of Tetradium ruticarpum (Rutaceae), three new compounds, ruticarpsides A–C (1–3), were obtained and their structures were elucidated by a comprehensive analysis of NMR and MS data. Compound 3 showed a weak inhibition effect on nitric oxide production in BV-2 microglial cells stimulated with lipopolysaccharide.

A process for the preparation of eugenol

The invention relates to the technical field of chemical synthesis, and in particular relates to a preparation method of a syringic acid. According to the method, a reaction can be carried out in a normal-temperature environment or at a low temperature value (40 DEG C) by selecting and matching raw materials, so that the preparation process of the syringic acid is low in energy consumption, and thus the production cost of the syringic acid is lowered. The method is simple in reaction aftertreatment, i.e., a catalyst, a solvent and a small amount of polyhydroxy benzoic acid generated in a reaction process, which have good water solubility, can be separated from the syringic acid product via a simple extraction operation, so that a purification operation does not need to be further carried out. Thus, the synthetic cost is lowered.

Method for selective demethylation of ortho-trimethoxybenzene compounds

The invention relates to a method for selective demethylation of ortho-trimethoxybenzene compounds and provides a method for preparation of 2,6-dimethoxyphenol derivatives by selective demethylation of ortho-trimethoxybenzene in different substitution types. By taking substitutional or non-substitutional ortho-trimethoxybenzene as a raw material, taking ZrCl4 as a catalyst and taking anisole as an additive, a ratio of the raw material to the catalyst to the additive is optimized in a reaction process to realize selective demethylation at a low reaction temperature ranging from the room temperature to 60 DEG C. The method has the advantages of mild reaction conditions, safety, reliability, low cost and easiness in operation and acquisition of the additive and the catalyst for reaction, simplicity and easiness in separation of reaction products, wide substrate application range and the like. The method effectively improves reaction safety and controllability and has an extensive application prospect in preparation of medicines, material intermediates and fine chemicals.