trans-Cinnamic acid
[CAS# 140-10-3]

Identification

• Classification: Pharmaceutical intermediate >> Heterocyclic compound intermediate >> Pyrimidine compound >> Carboxylic acid
• Name: trans-Cinnamic acid
• Synonyms: 3-Phenyl-2-propenoic acid; trans-3-Phenylacrylic acid
• Molecular Formula: C₉H₈O₂
• Molecular Weight: 148.16
• CAS Registry Number: 140-10-3
• EC Number: 205-398-1
• SMILES: C1=CC=C(C=C1)/C=C/C(=O)O

Properties

• Density: 1.248
• Melting point: 131-136 °C
• Boiling point: 300 °C
• Water solubility: 0.4 g/L (20 °C)

Safety Data

• Hazard Symbols: GHS07 Warning
• Risk Statements: H315-H319-H335
• Safety Statements: P261-P264-P264+P265-P271-P280-P302+P352-P304+P340-P305+P351+P338-P319-P321-P332+P317-P337+P317-P362+P364-P403+P233-P405-P501

Hazard Classification

Hazard	Class	Category Code	Hazard Statement
Eye irritation	Eye Irrit.	2	H319
Skin irritation	Skin Irrit.	2	H315
Specific target organ toxicity - single exposure	STOT SE	3	H335
Eye irritation	Eye Irrit.	2A	H319

Discovery and Applications

Trans-cinnamic acid is a naturally occurring organic compound first isolated from cinnamon oil in 1831 by French chemist Auguste Bussy. Trans-cinnamic acid is found in various plants including cinnamon, shea butter, and Peru balsam. Its unique aroma and chemical properties have attracted the interest of the scientific community, leading to research into its synthesis, biological activity, and multiple applications.

Trans-cinnamic acid is widely used in the flavor and fragrance industry and is a key ingredient in perfumes, cosmetics, and food flavorings. Its sweet, balsamic aroma is reminiscent of cinnamon, adding warmth and depth to perfume compositions. In the food industry, trans-cinnamic acid is used as a flavoring agent to add a spicy, aromatic flavor to baked goods, confectionery, and beverages.

Trans-cinnamic acid has a variety of pharmacological properties, including antioxidant, anti-inflammatory, and antimicrobial effects. It is used in pharmaceutical formulations and has potential efficacy in the treatment of inflammatory diseases, skin diseases, and microbial infections. Derivatives of trans-cinnamic acid are also being studied extensively as novel drug candidates in drug development.

Trans-cinnamic acid is used as a UV absorber in sunscreen formulations and cosmetics to protect the skin from harmful UV rays. Its conjugated double bond structure absorbs UV-B and UV-C wavelengths, reducing the risk of sunburn, premature aging, and skin cancer caused by excessive sun exposure. Trans-cinnamic acid enhances the photoprotective efficacy of sunscreen products.

Trans-cinnamic acid and its derivatives have antimicrobial properties and are used as preservatives in food and beverage products to inhibit microbial growth and extend shelf life. They help prevent spoilage and foodborne illness caused by bacteria, fungi, and yeasts. Trans-cinnamic acid derivatives such as cinnamaldehyde are commonly used in food preservation due to their strong antimicrobial activity.

Trans-cinnamic acid is a versatile building block used in organic synthesis to prepare a variety of fine chemicals, pharmaceutical intermediates, and agrochemicals. Its functional group reactivity allows the synthesis of a variety of compounds through chemical transformations such as esterification, hydrogenation, and oxidation for the synthesis of flavors, fragrances, and pharmaceuticals.

Trans-cinnamic acid plays a role in plant physiology as a signaling molecule and plant growth regulator. It regulates plant development, photosynthesis, and defense responses to biotic and abiotic stresses. Trans-cinnamic acid derivatives (such as methyl cinnamate) are used as growth regulators and crop protection agents in agriculture to promote plant growth and increase productivity.

References

2012. Amelioration of cyclophosphamide induced myelosuppression and oxidative stress by cinnamic acid. Chemico-Biological Interactions.
DOI: 10.1016/j.cbi.2012.01.001

2024. Unraveling the phytochemical complexity and antimicrobial potency of introduced versus native Argania spinosa trees in Eastern Morocco. Chemical Papers.
DOI: 10.1007/s11696-024-03739-1

2010. Cinnamon extract induces tumor cell death through inhibition of NFkappaB and AP1. BMC Cancer.
DOI: 10.1186/1471-2407-10-392