Product name: Cinnamyl cinnamate
Synonym name:
Catalogue No.: SBP02512
Cas No.: 122-69-0
Formula: C₁₈H₁₆O₂
Mol Weight: 264.324
Botanical Source:
Physical Description: Powder
Type of Compound: Phenylpropanoids

Purity: 95%~99%
Analysis Method: HPLC-DAD or/and HPLC-ELSD
Identification Method: Mass, NMR
Packing: Brown vial or HDPE plastic bottle
The product could be supplied from milligrams to grams. Inquire for bulk scale.
We provide solution to improve the water-solubility of compounds, thereby facilitating the variety of activity tests and clinic uses.

For Reference Standard and R&D, Not for Human Use Directly.

NMR of Cinnamyl cinnamate

HPLC of Cinnamyl cinnamate

Storage conditions：Short-term storage at 2~8℃, long-term storage at -20 ~ -80℃

Introduction/Overview

Cinnamyl cinnamate (CAS No.: 122-69-0), commonly known as Styracin, is a naturally occurring ester compound, mainly formed by the esterification reaction between cinnamic acid and cinnamonyl alcohol. This compound has attracted widespread attention in the field of natural product pharmacology in recent years due to its unique aromatic structure and diverse bioactivity. Cinnamate cinnamate is mainly found in plants such as Liquidambar orientalis Mill (Eurasian maple aroma). As a plant secondary metabolite, it possesses potential anti-inflammatory, antioxidant, antibacterial, and neuroprotective multiple pharmacological activities. With in-depth research into the pharmacological mechanisms of natural products, the biological functions and molecular targets of cinnamate have gradually been revealed, providing a theoretical foundation for its development into novel drugs.

This paper aims to systematically review the chemical structure and physicochemical properties of cinnamate cinnamate, plant origin and extraction methods, pharmacological activity and mechanism of action, druggability evaluation, and pharmacokinetic characteristics. Combined with current research progress, it explores its clinical application prospects and future directions, providing references for researchers and drug developers in related fields.

Chemical structure and physicochemical properties

The molecular formula of cinnamate cinnamon ester is C18H16O2, with a molecular weight of 266.32. Its structure consists of a cinnamic acid molecule and a cinnamol molecule connected by ester bonds, forming typical aromatic ester compounds. The structure contains conjugated double bonds and aromatic rings, giving it strong chemical stability and biological activity. Its LogP value is 3.5, indicating that the compound has moderate lipid solubility, which may facilitate membrane penetration and distribution in vivo. The topological pole surface area (TPSA) is 26.3 Ų, and the number of hydrogen bond acceptors is 2, suggesting that it has a certain affinity for binding to biomacromolecules.

The physicochemical properties of cinnamate include good thermal stability and relatively low polarity, which make it easy to accumulate within the plant and facilitate its extraction and purification. Its aromatic structure gives it characteristic UV absorption peaks, facilitating qualitative and quantitative analysis using spectroscopic methods.

Plant Origins and Extraction Methods

Cinnamyl ester mainly comes from Liquidambar orientalis mill, a plant widely distributed in the Mediterranean region and an important member of the Eurasian Cinnamon genus. The plant's resin and leaves are rich in various phenolic and ester natural products, with cinnamic acid being particularly high.

Common methods for extracting cinnamon ester include solvent extraction, ultrasound-assisted extraction, and distillation. Solvent extraction typically uses organic solvents such as ethanol, methanol, or ethyl acetate, and combined with ultrasound-assisted technology, can significantly improve extraction efficiency. After rotary evaporation and concentration, the extract was separated and purified using techniques such as column chromatography, thin-layer chromatography (TLC), and high-performance liquid chromatography (HPLC). In recent years, supercritical CO2 extraction technology, due to its green environmental friendliness and efficient selectivity, has gradually been applied to the extraction of cinnamate cinnamate, significantly improving purity and yield.

Moreover, research on plant tissue culture and biosynthetic pathways provides a theoretical basis for the biosynthesis of cinnamate ester and holds promise for large-scale production through genetic engineering methods.

Pharmacological activity research

Cinnamate exhibits a variety of biological activities, including anti-inflammatory, antioxidant, antibacterial, antitumor, and neuroprotective properties.

1. Anti-inflammatory activity
   Multiple in vitro and in vivo studies have shown that cinnamate can significantly inhibit the production of inflammatory mediators such as tumor necrosis factor-α (TNF-α), interleukin-6 (IL-6), and nitric oxide (NO). By inhibiting the nuclear factor κB (NF-κB) signaling pathway, it reduces the cascading amplification of inflammatory responses, demonstrating good anti-inflammatory effects.

2. Antioxidant activity
   Cinnamate has the ability to scavenge free radicals, effectively inhibiting lipid peroxidation and protecting cells from oxidative stress damage. Both the DPPH and ABTS free radical scavenging experiments demonstrated strong antioxidant capacity, suggesting its potential application value in the prevention and treatment of oxidation-related diseases.

3. Antibacterial activity
   Research shows that cinnamate inhibits various Gram-positive and Gram-negative bacteria, especially showing lower minimum inhibitory concentrations (MIC) against Staphylococcus aureus and Escherichia coli. Its antibacterial mechanism may involve destruction of bacterial cell membranes and metabolic inhibition.

4. Antitumor activity
   Preliminary cell experiments have shown that cinnamate can induce apoptosis in tumor cells and inhibit cell proliferation. Its mechanism involves regulating cyclins and activating mitochondria-dependent apoptosis pathways, demonstrating potential anticancer value.

5. Neuroprotective effects
   Some studies suggest that cinnamate may have potential neuroprotective effects by inhibiting neuroinflammation and oxidative stress, reducing nerve cell damage, and showing especially positive effects in Parkinson's and Alzheimer's disease models.

Mechanism of action and molecular targets

The biological activity of cinnamate is closely related to its mechanism of action, mainly involving the following molecular targets and signaling pathways:

1. NF-κB signaling pathway
   As a core regulator of inflammatory response, activation of NF-κB promotes the expression of various inflammatory factors. Cinnamate exerts its anti-inflammatory effect by inhibiting the phosphorylation and degradation of IκBα, blocking NF-κB nuclear translocation, and reducing the release of pro-inflammatory factors.

2. Nrf2-ARE antioxidant pathway
   Cinnamyl can activate nuclear factor 2-related factor 2 (Nrf2), promoting the expression of antioxidant enzymes such as superoxide dismutase (SOD) and glutathione peroxidase (GPx), thereby enhancing cellular antioxidant defense.

3. Mitochondrial apoptosis pathway
   In tumor cells, cinnamate regulates the expression of Bcl-2 family proteins, promotes cytochrome c release, activates the caspase cascade, induces apoptosis, and inhibits tumor cell proliferation.

4. Cell membrane integrity and inhibition of metabolic enzymes
   Its antibacterial effect is partly attributed to damage to bacterial cell membranes and inhibition of key metabolic enzymes, leading to disordered energy metabolism and cell death.

Currently, research on the interactions between cinnamate and other molecular targets remains limited. In the future, it is necessary to combine molecular docking, proteomics, and genomics techniques to deeply analyze its network of actions.

Druggability evaluation and pharmacokinetics

From the perspective of druggability, cinnamate cinnamyl has relatively ideal physicochemical properties. Its molecular weight is 266.32, meeting the requirement of a molecular weight less than 500 in Lipinski's "Five Rules"; A LogP value of 3.5 indicates moderate lipid solubility, which facilitates cell membrane penetration and oral absorption; TPSA is 26.3 Ų, and low polarity helps biofilm permeability.

However, safety indicators such as blood-brain barrier penetration, hepatotoxicity, cardiotoxicity (including hERG channel inhibition), and genotoxicity (Ames assay) remain unclear, requiring further systematic evaluation. Preliminary in vitro cytotoxicity studies show a broad safety window, but there is a lack of systematic in vivo toxicology data.

Pharmacokinetics, related research is relatively scarce. It is speculated that it has high lipophilusity and may have good oral bioavailability, but its metabolic pathway, half-life, tissue distribution, and excretion mode remain unclear. Future studies on absorption, distribution, metabolism, and excretion (ADME) are needed in animal models to clarify their in vivo behavioral characteristics.

Prospects and outlooks for clinical applications

Given the good activity of cinnamate in anti-inflammatory, antioxidant, antibacterial, and antitumor aspects, its clinical application prospects are broad. Especially in adjunctive therapy for chronic inflammatory diseases, infectious diseases, and certain tumors, cinnamate is expected to play a role as a natural drug or a drug-lead compound.

Moreover, its potential neuroprotective effects offer new approaches for the treatment of neurodegenerative diseases. By combining modern drug design techniques and optimizing efficacy and safety through structural modification, it is expected that derivatives with greater clinical value will be developed.

Future research should focus on the following directions:

1. Systematic pharmacological and toxicological evaluation
   Improving in vivo and in vitro safety and efficacy studies to clarify drug dosage ranges and potential toxicities.

2. Pharmacokinetics and pharmacokinetic studies
   Revealing its metabolic pathways in vivo and the time-concentration relationship of action to provide a basis for clinical medication.

3. In-depth analysis of molecular mechanisms
   Using multi-omics techniques and computational biology methods, the targets of action and signal networks are systematically clarified.

4. Dosage form development and clinical translation
   Exploring delivery methods suitable for their physicochemical properties, such as nanocarriers and sustained-release formulations, to improve bioavailability and targeting.

5. Clinical trial design
   Promoting early clinical research to verify its safety and efficacy in specific diseases.

Conclusion

Cinnamyl cinnalate, a natural ester compound derived from Liquidambar orientalis Mill, demonstrates broad drug development potential due to its unique chemical structure and diverse pharmacological activities. Current research has preliminarily revealed its multiple biological functions and some molecular mechanisms including anti-inflammatory, antioxidant, antibacterial, and antitumor properties, but its safety, pharmacokinetics, and clinical applications still require further exploration.

In the future, through multidisciplinary collaboration and modern drug development technologies, cinnamate is expected to become an important candidate molecule for new natural drugs, providing new strategies and methods for treating related diseases. Researchers should continuously focus on its mechanisms and clinical translation to advance its transition from laboratory to clinical application.