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Product name: Cinnamic acid
Synonym name: trans-3-Phenylacrylic acid
Catalogue No.: BP0364
Cas No.: 140-10-3
Formula: C9H8O2
Mol Weight: 148.161
Botanical Source: Cinnamomum cassia Presl
Physical Description:
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
Storage: Store in a well closed container, protected from air and light. Put into refrigerate or freeze for long term storage.
Whenever possible, you should prepare and use solutions on the same day. However, if you need to make up stock solutions in advance, we recommend that you store the solution as aliquots in tightly sealed vials at -20℃. Generally, these will be useable for up to two weeks.
The product could be supplied from milligrams to grams
Inquire for bulk scale.
Chengdu Biopurify Phytochemicals Ltd. is a leading company in the research, development, manufacture and marketing of High Quality Phytochemicals and Extracts(especially Active Ingredients from Traditional Chinese Medicine，TCM), Natural Active Pharmaceutical Ingredients worldwide.
The main services:
A. Supply active ingredients and reference standards of TCM, from mgs to kgs scale
B. Custom extraction and purification, target Herb Active Ingredients
C. Custom synthesis and semi-synthesis for Natural Active Ingredients
D. CR(contract research), CM(contract manufacture) and PD(process development) services from lab scale, pilot scale to commercial scale(GMP is also available)
E. TCM compounds library for drug screen,more than 3000 compounds available, many of them are rare and unique.
NMR of Cinnamic acid
HPLC of Cinnamic acid
Storage conditions：Short-term storage at 2~8℃, long-term storage at -20 ~ -80℃
37.3000
2.1300
1.9100
.4000
High
90.0000
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No
No
No
No
No
No
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Cinnamic acid (CAS No.: 140-10-3) is a natural organic acid widely found in various plants and belongs to the aromatic carboxylic acid class. As one of the main components of cinnamon plants and many other spice plants, cinnamic acid has attracted widespread attention in the field of natural product pharmacology in recent years due to its unique chemical structure and diverse biological activities. Especially in cancer intervention and antioxidant damage, cinnamic acid has shown significant potential, involving inhibitory effects on multiple tumor cell lines and regulation of multiple antioxidant-related signaling pathways. This paper systematically reviews the chemical structure and physicochemical properties of cinnamic acid, plant origin and extraction methods, pharmacological activity and mechanism of action, druggability evaluation and pharmacokinetic characteristics, and, combined with current research progress, explores its clinical application prospects and future directions.
The chemical formula of cinnamic acid is C9H8O2, with a molecular weight of 148.1600. Its structure consists of a benzene ring and a carboxyl group connected by an unsaturated carbon chain, specifically 3-phenylacrylic acid (C6H5-CH=CH-COOH). This structure gives cinnamic acid its unique chemical and bioactive properties. The LogP value of cinnamic acid is 2.13, indicating moderate lipid solubility, which is beneficial for cell membrane penetration and bioavailability. The polar surface area (TPSA) is 37.3 Ų, with 3 hydrogen bond acceptors and low water solubility (0.4 mg/mL), indicating limited solubility in the aqueous phase but moderate lipid solubility, which is beneficial for distribution in vivo.
In the molecular structure of cinnamic acid, the conjugated structure of the benzene ring and unsaturated carboxyl chain gives it strong free radical scavenging ability and antioxidant properties. It has good chemical stability and can withstand conventional extraction and storage conditions. Cinnamic acid has a high blood-brain barrier penetration ability (BBB: High), suggesting its potential application value in central nervous system diseases.
Cinnamic acid is widely found in various plants, especially the bark, leaves, and roots of Cinnamon species (Cinnamum spp.). In addition, clove, licorice, fennel, and various spice plants also contain certain amounts of cinnamic acid. Its naturally occurring form is mostly in the free form or in combination with glycosides and esters.
Traditional extraction methods mainly include solvent extraction, distillation, and supercritical fluid extraction. Common solvents include polar solvents such as ethanol, methanol, and ethyl acetate, which can effectively extract cinnamic acid and its derivatives. In recent years, the application of ultrasound-assisted extraction and microwave-assisted extraction technologies has improved extraction efficiency and purity, reducing solvent usage and time costs. In addition, high-performance liquid chromatography (HPLC) and gas chromatography-mass spectrometry (GC-MS) techniques are widely used for qualitative and quantitative analysis of cinnamic acid.
Cinnamic acid exhibits inhibitory effects in various tumor cell lines. Studies have shown that its IC50 values for glioblastoma, melanoma, prostate cancer, and lung cancer cells range from 1 to 4.5 mM, suggesting certain cytotoxicity. Cinnamic acid exerts anti-cancer effects by inducing tumor cell apoptosis and inhibiting cell proliferation and migration. Some in vitro and in vivo experiments have shown that cinnamic acid can regulate tumor-related signaling pathways, inhibit tumor angiogenesis, and enhance the sensitivity of chemotherapy drugs.
Cinnamic acid has significant antioxidant capacity, scavenging free radicals and reducing cell damage caused by oxidative stress. Its antioxidant effects mainly involve activating intracellular antioxidant enzyme systems, including superoxide dismutase (SOD), catalase (CAT), and glutathione peroxidase (GPX). Additionally, cinnamic acid can upregulate the NFE2L2/NRF2 signaling pathway, enhancing cellular antioxidant defenses and slowing the progression of oxidative damage-related diseases. In terms of anti-inflammation, cinnamic acid exerts protective effects by inhibiting the release of inflammatory mediators and reducing the expression of inflammatory factors.
In addition to anticancer and antioxidant properties, cinnamic acid also exhibits multiple biological activities including antibacterial, antiviral, hypoglycemic, and neuroprotective effects. Its penetrating ability to the central nervous system has attracted attention for its potential applications in neurodegenerative diseases.
The biological activity of cinnamic acid is closely related to its regulation of multiple signaling pathways and molecular targets. Regarding antioxidant damage, cinnamic acid activates NFE2L2/NRF2 transcription factors, promoting the expression of downstream antioxidant enzyme genes such as SOD1, SOD2, CAT, GPX1, and HMOX1, enhancing cellular antioxidant capacity and reducing cellular damage caused by oxidative stress.
In its antitumor mechanisms, cinnamic acid regulates the cell cycle, induces apoptosis, and inhibits tumor cell migration through multi-target action. Its targets include modulating the Bcl-2 family proteins, activating the caspase enzyme system, inhibiting the NF-κB signaling pathway, and suppressing tumor-associated angiogenesis factors. Some studies also indicate that cinnamic acid can influence the tumor microenvironment, regulate immune responses, and enhance anti-tumor immune effects.
Additionally, cinnamic acid inhibits the expression of inflammatory factors such as TNF-α and IL-6, alleviating chronic inflammatory conditions and indirectly exerting anti-cancer and tissue-protective effects.
The molecular weight of cinnamic acid is 148.16, meeting the Lipinski rule requirement for molecular weight less than 500. Its LogP value is 2.13, indicating moderate lipid solubility, which is beneficial for oral absorption and cell membrane penetration. The TPSA is 37.3, and its low polarity surface area helps cross the blood-brain barrier, supporting its potential applications in central nervous system diseases.
Toxicological evaluation showed that cinnamic acid had low acute toxicity, with an LD50 of about 2500 mg/kg. There was no significant evidence of hepatotoxicity or cardiotoxicity. Both hERG channel inhibition and Ames-induced mutagenic tests were negative, suggesting high safety.
Pharmacokinetics, cinnamic acid is well absorbed orally but has limited bioavailability due to its low water solubility. Its metabolism in the body is mainly carried out through hepatic enzyme systems for hydroxylation and binding reactions, enhancing the water solubility of metabolites and facilitating excretion. Its high blood-brain barrier permeability allows for good distribution in the central nervous system. In the future, drug formulation improvements and structural modifications are expected to further enhance their pharmacokinetic performance.
As a natural product, cinnamic acid demonstrates broad clinical application potential due to its multi-target and multi-mechanism biological activity. Its application in cancer intervention is particularly prominent, particularly its inhibitory effect on malignant tumors such as glioblastoma, melanoma, prostate cancer, and lung cancer, providing important clues for the development of novel anti-tumor drugs.
Additionally, cinnamic acid's potential in antioxidant damage and neuroprotection makes it a strong candidate for treating neurodegenerative diseases, chronic inflammation, and metabolic syndrome. Its excellent safety profile and blood-brain barrier penetration ability lay the foundation for drug development for central nervous system diseases.
Future research should focus on structural optimization, formulation improvement, and combination therapy strategies to enhance its bioavailability and targeting. At the same time, in-depth analysis of its molecular mechanisms and systematic preclinical and clinical studies to verify efficacy and safety will provide a solid basis for clinical translation.
As a natural product with rich pharmacological activity, cinnamic acid holds an important position in the field of natural product pharmacology due to its anti-cancer, antioxidant, and multi-biological effects. Its excellent druggability parameters and safety provide favorable conditions for subsequent drug development and clinical application. In the future, through multidisciplinary collaboration and combining modern medicinal chemistry, molecular biology, and clinical medical methods, cinnamic acid is expected to become a novel drug for treating various diseases, especially cancer and neurological disorders. Systematic and in-depth research will drive cinnamic acid from the laboratory to clinical practice, benefiting a wide range of patients.
Shenshuai
Wenjing
Hedandan
