49508

Sinapic acid

matrix substance for MALDI-MS, ≥99.5%, Ultra pure

• Synonym(s): 3,5-Dimethoxy-4-hydroxycinnamic acid, 4-Hydroxy-3,5-dimethoxy-cinnamic acid, Sinapinic acid
• Empirical Formula (Hill Notation): C₁₁H₁₂O₅
• CAS Number: 530-59-6
• Molecular Weight: 224.21
• Beilstein: 2699118
• EC Number: 208-487-3
• MDL number: MFCD00004401
• UNSPSC Code: 12000000
• PubChem Substance ID: 329757465
• NACRES: NA.21

Properties

• grade: matrix substance for MALDI-MS
• Quality Level: 100
• Assay: ≥99.5% (HPLC); ≥99.5%
• analyte chemical class(es): dendrimers, fullerenes, peptides, proteins
• technique(s): MALDI-MS: suitable
• mp: ~202 °C
• solubility: dioxane: 1 g/10 mL at hot, clear, faintly yellow to yellow
• cation traces: Al: ≤1 mg/kg; Ba: ≤1 mg/kg; Ca: ≤2 mg/kg; Cd: ≤1 mg/kg; Co: ≤1 mg/kg; Cr: ≤1 mg/kg; Cu: ≤1 mg/kg; Fe: ≤1 mg/kg; K: ≤2 mg/kg; Li: ≤1 mg/kg; Mg: ≤1 mg/kg; Mn: ≤1 mg/kg; Na: ≤2 mg/kg; Ni: ≤1 mg/kg; Sr: ≤1 mg/kg; Zn: ≤1 mg/kg
• suitability: in accordance for UV test
• SMILES string: COc1cc(\C=C\C(O)=O)cc(OC)c1O
• InChI: 1S/C11H12O5/c1-15-8-5-7(3-4-10(12)13)6-9(16-2)11(8)14/h3-6,14H,1-2H3,(H,12,13)/b4-3+
• InChI key: PCMORTLOPMLEFB-ONEGZZNKSA-N

Description

General description

Sinapic acid is one of the 4 most common hydroxycinnamic acids. It is widespread in the plant kingdom (vegetables, fruits, oilseed crops, cereal grains and medicinal plants, and some spices). It is mostly found in the form of esters, but may exist in the free form too.

Application

• Metabolic Fate Characterization: Sinapic acid′s metabolic fate in biological systems is a significant area of research. Recent studies in rats have focused on identifying the metabolic pathways and by-products of sinapic acid, using advanced techniques such as liquid chromatography-mass spectrometry (LC-MS). These studies provide insights into its bioavailability and pharmacokinetics, which are crucial for understanding its therapeutic potential (Analytical and Bioanalytical Chemistry, 2023).


• Efficient Extraction from Plant Materials: Sinapic acid is extracted from various plant sources using molecularly imprinted polymers (MIPs) and deep eutectic solvents. These methods enhance the efficiency and selectivity of sinapic acid extraction, making it a valuable approach for analytical chemists working on natural product isolation and characterization. This application is particularly relevant in the food and pharmaceutical industries for quality control and standardization (Food Chemistry, 2023).


• Selective Sensing Applications: Sinapic acid is used in the development of nanocomposites for selective sensing applications. For instance, Ni-sinapic acid nanocomposites have been developed for the selective detection of permanganate ions. This research showcases the versatility of sinapic acid in creating sensitive and specific sensors for environmental monitoring and analytical applications (Journal of Photochemistry and Photobiology A: Chemistry, 2023).


• Bioactivity Studies: The bioactivity of sinapic acid extends to its anti-inflammatory and anticancer properties. Studies have shown that sinapic acid can modulate various biochemical pathways, providing protective effects against inflammation and cancer. These findings underscore its potential as a bioactive compound in therapeutic formulations and highlight the importance of analytical methods in quantifying its efficacy and safety (Stem Cell Research International, 2022).

Biochem/physiol Actions

On removal of amino group from phenylalanine, catalysing with enzyme phenylalanine ammonia-lyase forms cinnamic acid. The precursor of hydroxycinnamates is produced after hydroxylation of benzene ring. One of the precursors produced is sinapic acid. Sinapic acid exhibits antimicrobial, antioxidant, anticancer, anti-inflammatory, and anti-anxiety activity. Sinapine (sinapoyl choline) has been acknowledged as an acetylcholinesterase inhibitor, making it therapeutically applicable in treatment of various diseases. 4-Vinylsyringol (a decarboxylation product of sinapic acid) is a potent antimutagenic and antioxidative agent, involved in suppressing the induction of inflammatory cytokines and carcinogenesis. Owing to their anti-oxidative activity, these compounds have been considered to be potentially employed in the pharmaceutical industry, cosmetics and food processing.

Sinapic acid was suitable as phenolic standard for HPLC analysis in determination of Sinapic acid derivatives in Canola extracts. 10 g/L of sinapinic acid with solvent was suitable as matrix for ultraviolet laser desorption mass spectrometric determination of proteins. It was also suitable to use as matrix for MALDI-TOFMS and MALDI-ion mobility-TOFMS to determine phospholipids in tissue.

Packaging

Bottomless glass bottle. Contents are inside inserted fused cone.

Safety Information

• Pictograms: GHS07
• Signal Word: Warning
• Hazard Statements: H315 - H319 - H335
• Precautionary Statements: P261 - P264 - P271 - P280 - P302 + P352 - P305 + P351 + P338
• Hazard Classifications: Eye Irrit. 2 - Skin Irrit. 2 - STOT SE 3
• Target Organs: Respiratory system
• Storage Class Code: 11 - Combustible Solids
• WGK: WGK 3
• Flash Point(F): Not applicable
• Flash Point(C): Not applicable
• Personal Protective Equipment: dust mask type N95 (US), Eyeshields, Gloves