Sinapine

• CAS: 18696-26-9
• Catalog Number: ACM18696269
• Category: Main Products
• Molecular Weight: 310.36
• Molecular Formula: [C₁₆H₂₄NO₅]+
• Synonyms: 2-[[3-(4-Hydroxy-3,5-dimethoxyphenyl)-1-oxo-2-propenyl]oxy]-N,N,N-trimethylethanaminium
• IUPAC Name: 2-[(E)-3-(4-hydroxy-3,5-dimethoxyphenyl)prop-2-enoyl]oxyethyl-trimethylazanium
• Canonical SMILES: C[N+](C)(C)CCOC(=O)C=CC1=CC(=C(C(=C1)OC)O)OC
• InChI: InChI=1S/C16H23NO5/c1-17(2,3)8-9-22-15(18)7-6-12-10-13(20-4)16(19)14(11-12)21-5/h6-7,10-11H,8-9H2,1-5H3/p+1
• InChI Key: HUJXHFRXWWGYQH-UHFFFAOYSA-O
• Melting Point: 178 °C
• Appearance: White or light-tan solid.
• Complexity: 363
• Covalently-Bonded Unit Count: 1
• Defined Atom Stereocenter Count: 0
• Exact Mass: 310.16544787
• Heavy Atom Count: 22
• Hydrogen Bond Acceptor Count: 5
• Hydrogen Bond Donor Count: 1
• Isomeric SMILES: C[N+](C)(C)CCOC(=O)/C=C/C1=CC(=C(C(=C1)OC)O)OC
• Monoisotopic Mass: 310.16544787
• Physical State: Powder
• Rotatable Bond Count: 8
• Topological Polar Surface Area: 65 Ų

Case Study

Sinapine for the Preparation of Sinapine-Protein Complexes

Li Y, et al. Journal of Molecular Liquids, 2024, 414(B), 126249.

The preparation of protein-sinapine complexes involves a methodical approach to enhance the bioactivity and potential applications of both sinapine and proteins in various functional systems. Zein colloidal particles were synthesized through a classical anti-solvent technique, wherein corn protein (1 g) was dissolved in 80% ethanol and mixed with ultrapure water under sonication at 40 kHz for 10 minutes. This procedure resulted in a concentrated protein suspension (25 mL) at a 4% (w/v) concentration. Similarly, SPI and WPI protein complexes were prepared by dissolving 2 g of protein in 50 mL deionized water, followed by magnetic stirring at 500 rpm for 2 hours at room temperature and overnight hydration at 4°C.
Sinapine-protein complexes were formed by incubating the prepared protein solutions with varying sinapine concentrations (0.05%, 0.1%, 0.2% w/v) for 24 hours at 4°C. The system's pH was adjusted to 3, 7, and 9 to study the effect of pH on complex formation. Free sinapine was removed via dialysis using 3 KDa bags, and the complexes were lyophilized for subsequent analyses.

Sinapine as a Stabilizing Agent for Protein-Based Oleogels with Adjustable Rheological and Textural Properties

Li Y, et al. Food Bioscience, 2024, 58, 103622.

Sinapine has emerged as a promising compound in the development of oleogels, which serve as potential substitutes for saturated or trans fats. In this study, sinapine was utilized to enhance the stability of protein-based oleogels through a capillary suspension method. The incorporation of sinapine in varying concentrations (4-8 μg/mL) facilitated the formation of capillary bridges between protein particles, significantly improving the oil constraint capacity of whey protein isolate (WPI)-based oleogels by approximately 20%.
The structural integrity of the oleogels was found to be highly dependent on both the protein's hydrophilic capacity and the sinapine concentration in the secondary fluid. Notably, the stabilized oleogels demonstrated a high energy storage modulus and notable thixotropic recovery, underscoring the stabilizing effect of sinapine. These properties contribute to the dense structure of the oleogels, which is formed by the synergistic interaction of interfacially adsorbed particles and a polymer gel network. The results suggest that sinapine-protein oleogels, prepared via the capillary suspension method, offer adjustable rheological and textural properties, making them suitable for food applications.

Sinapine as a Protective Agent Against Oxidative Stress in Hepatocytes Induced by LPS

Li D, et al. Life Sciences, 2022, 306, 120828.

Sinapine has demonstrated significant potential in mitigating oxidative stress in hepatocytes, particularly in models of non-alcoholic fatty liver disease (NAFLD). This study investigates its protective effects in THLE-2 cells exposed to lipopolysaccharide (LPS), an inducer of oxidative stress. Sinapine at concentrations of 5, 20, and 80 µM was shown to reduce malondialdehyde (MDA) levels by 27.67% compared to the LPS-only group, indicating its antioxidant potential. Moreover, sinapine treatment notably increased the activity of antioxidant enzymes, such as superoxide dismutase (SOD) and glutathione peroxidase (GSH-Px), by 40.61% and 49.60%, respectively. It also effectively reduced reactive oxygen species (ROS) levels by up to 40.31%, further confirming its antioxidative properties. Mechanistically, sinapine down-regulated the expression of mitochondrial uncoupling protein MCJ, a key regulator of oxidative stress, contributing to the restoration of mitochondrial function. These findings support the therapeutic potential of sinapine in protecting liver cells from oxidative damage, positioning it as a promising candidate for the management of liver diseases associated with oxidative stress.

Custom Q&A

What is the molecular formula of sinapine?

The molecular formula of sinapine is C16H24NO5+.

What is the molecular weight of sinapine?

The molecular weight of sinapine is 310.36 g/mol.

What is the IUPAC name of sinapine?

The IUPAC name of sinapine is 2-[(E)-3-(4-hydroxy-3,5-dimethoxyphenyl)prop-2-enoyl]oxyethyl-trimethylazanium.

What is the InChIKey of sinapine?

The InChIKey of sinapine is HUJXHFRXWWGYQH-UHFFFAOYSA-O.

What are the synonyms for sinapine?

The synonyms for sinapine are O-sinapoylcholine, Sinapoylcholine, sinapin.

What is the role of sinapine in plants?

Sinapine functions as a photosynthetic electron-transport chain inhibitor, an antioxidant, and a plant metabolite.

What are the natural sources of sinapine?

Sinapine is found in Alliaria petiolata, Isatis quadrialata, and other organisms.

Does sinapine have any occurrence in Lotus, the natural products occurrence database?

Yes, sinapine has occurrence data in Lotus, the natural products occurrence database.

What is the CAS number of sinapine?

The CAS number of sinapine is 18696-26-9.

Is sinapine a canonicalized compound?

Yes, sinapine is a canonicalized compound.