Cinnamyl alcohol
[CAS# 104-54-1]

Identification

• Classification: Organic raw materials >> Alcohols, phenols, phenolic compounds and derivatives >> 2-Cycloalcohol
• Name: Cinnamyl alcohol
• Synonyms: 3-Phenyl-2-propene-1-ol
• Molecular Formula: C₉H₁₀O
• Molecular Weight: 134.18
• CAS Registry Number: 104-54-1
• EC Number: 203-212-3
• FEMA: 2294
• SMILES: C1=CC=C(C=C1)/C=C/CO

Properties

• Water solubility: 1.8 g/L (20 °C)
• Density: 1.0±0.1 g/mL, Calc.^*, 1.044 g/mL (Expl.)
• Melting point: 30-33 °C (Expl.)
• Index of Refraction: 1.599, Calc.^*
• Boiling Point: 250.0 °C (760 mmHg), Calc.^*, 250 °C (Expl.)
• Flash Point: 124.8±14.5 °C, Calc.^*, 126 °C (Expl.)

^* Calculated using Advanced Chemistry Development (ACD/Labs) Software.

Safety Data

• Hazard Symbols: GHS07 Warning
• Risk Statements: H302-H317
• Safety Statements: P261-P264-P264+P265-P270-P272-P280-P301+P317-P302+P352-P305+P354+P338-P317-P321-P330-P333+P317-P362+P364-P501

Hazard Classification

Hazard	Class	Category Code	Hazard Statement
Skin sensitization	Skin Sens.	1	H317
Acute toxicity	Acute Tox.	4	H302
Chronic hazardous to the aquatic environment	Aquatic Chronic	2	H411
Eye irritation	Eye Irrit.	2	H319
Skin sensitization	Skin Sens.	1B	H317
Skin irritation	Skin Irrit.	2	H315
Skin sensitization	Skin Sens.	1A	H317
Specific target organ toxicity - single exposure	STOT SE	3	H335

Discovery and Applications

Cinnamyl alcohol, also known as (E)-3-phenylprop-2-en-1-ol, is an organic compound with the chemical formula C9H10O. It is a naturally occurring substance that is primarily found in cinnamon oil and is responsible for the characteristic fragrance of cinnamon. It appears as a colorless to pale yellow liquid with a sweet, floral odor, often described as a spicy or cinnamon-like aroma.

Cinnamyl alcohol was first isolated from cinnamon oil in the 19th century and has since been studied for its chemical properties and potential applications. The compound can be synthesized through various methods, including the reduction of cinnamaldehyde, a major constituent of cinnamon oil. Other synthetic routes involve the alkylation of phenylpropene derivatives, followed by reduction to yield cinnamyl alcohol.

The primary applications of cinnamyl alcohol are in the fragrance and flavor industries, where it is used as a key ingredient in perfumes, soaps, and other scented products. It is valued for its pleasant odor, which is often used in combination with other aromatic compounds to create complex fragrances. In the food industry, cinnamyl alcohol can be used as a flavoring agent, typically imparting a cinnamon-like taste to baked goods, candies, and other products.

In addition to its use in fragrances and flavorings, cinnamyl alcohol has been explored for its potential therapeutic and biological properties. Studies have shown that cinnamyl alcohol exhibits antioxidant, anti-inflammatory, and antimicrobial activities, which may make it useful in the development of therapeutic agents or topical treatments. Some research has suggested its potential as a mild sedative or analgesic, though further investigation is required to confirm these effects.

Cinnamyl alcohol is also used in the synthesis of various chemical compounds, including cinnamic acid derivatives, and is a precursor to the production of certain resins and polymers. It is employed as a building block in the synthesis of various functionalized organic molecules used in industrial applications.

Due to its relatively low toxicity, cinnamyl alcohol is considered safe for use in consumer products, including cosmetics and food. However, as with any chemical compound, appropriate handling and safety precautions should be taken to avoid excessive exposure, particularly in industrial settings where large quantities are handled.

In summary, cinnamyl alcohol is a versatile compound with well-established uses in the fragrance, flavor, and chemical industries. Its applications are primarily related to its aromatic properties, and ongoing research into its biological activities continues to highlight its potential for further use in various fields.

References

1979. Antimicrobial activity of aroma chemicals and essential oils. Journal of the American Oil Chemists' Society, 56(5), 602.
DOI: 10.1007/bf02660245

2014. Catalysing sustainable fuel and chemical synthesis. Applied Petrochemical Research, 4(2), 56.
DOI: 10.1007/s13203-014-0056-z

2024. Highly selective alcohol oxidation by polyvinyl cyanuric chloride in DMSO: a metal-free approach. Research on Chemical Intermediates, 50(11), 5444.
DOI: 10.1007/s11164-024-05444-w