2-methyl-3-phenylprop-2-enal
[CAS# 101-39-3]

Identification

• Classification: Flavors and spices >> Synthetic spice >> Carboxylic acid and ester perfume >> Aromatic carboxylic acid ester
• Name: 2-methyl-3-phenylprop-2-enal
• Synonyms: Density|1.0±0.1 g/cm³, Calc.^*;Index of Refraction|1.563, Calc.^*, 1.605 (Expl.);Boiling Point|254.6±9.0 $degree$C (760 mmHg), Calc.^*, 138-140 $degree$C (14 mmHg) (Expl.);Flash Point|79.4±0.0 $degree$C, Calc.^*; (E)-2-methyl-3-phenylprop-2-enal
• Molecular Formula: C₁₀H₁₀O
• Molecular Weight: 146.19
• CAS Registry Number: 101-39-3
• EC Number: 202-938-8
• FEMA: 2697
• SMILES: C/C(=C\C1=CC=CC=C1)/C=O

Properties

• Density: 1.0±0.1 g/cm³, Calc.^*
• Index of Refraction: 1.563, Calc.^*, 1.605 (Expl.)
• Boiling Point: 254.6±9.0 ºC (760 mmHg), Calc.^*, 138-140 ºC (14 mmHg) (Expl.)
• Flash Point: 79.4±0.0 ºC, Calc.^*

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

Safety Data

• Hazard Symbols: GHS07 Warning
• Hazard Statements: H317
• Precautionary Statements: P261-P272-P280-P302+P352-P321-P333+P317-P362+P364-P501

Hazard Classification

Hazard	Class	Category Code	Hazard Statement
Skin sensitization	Skin Sens.	1	H317
Skin sensitization	Skin Sens.	1B	H317
Acute hazardous to the aquatic environment	Aquatic Acute	1	H400
Chronic hazardous to the aquatic environment	Aquatic Chronic	3	H412
Eye irritation	Eye Irrit.	2	H319
Skin irritation	Skin Irrit.	2	H315

Discovory and Applicatios

2-Methyl-3-phenylprop-2-enal, also known as α-methylcinnamaldehyde, is an aromatic aldehyde with the molecular formula C₁₀H₁₀O. This compound is characterized by its yellowish color and a sweet, spicy aroma reminiscent of cinnamon with floral undertones. It belongs to the cinnamaldehyde family, which has been extensively studied for its applications in flavors, fragrances, and chemical synthesis.

The discovery of α-methylcinnamaldehyde traces back to early 20th-century advancements in organic chemistry, where derivatives of natural cinnamaldehyde were synthesized to explore variations in reactivity and sensory properties. α-Methylcinnamaldehyde is commonly prepared through an aldol condensation reaction between benzaldehyde and isobutyraldehyde, followed by catalytic dehydration. This straightforward synthesis process ensures its availability for both industrial and research purposes.

In the fragrance industry, α-methylcinnamaldehyde is a valued component for its warm and spicy scent. It is widely incorporated into perfumes and personal care products to enhance aromatic profiles. Furthermore, it is used in air fresheners and household cleaning agents, offering a durable and appealing fragrance. Its ability to blend seamlessly with other aroma chemicals makes it a versatile choice for various scent formulations.

The compound also holds significance in the flavor industry due to its intense, spicy-sweet flavor profile. It is used sparingly in confectionery, baked goods, and beverages to impart a warm cinnamon-like taste. Regulatory bodies, such as the FDA, recognize α-methylcinnamaldehyde as a safe food additive when utilized within prescribed limits.

In chemical synthesis, α-methylcinnamaldehyde serves as a precursor for various organic reactions. Its reactive aldehyde group and conjugated double bond enable it to act as a building block for heterocyclic compounds, which are essential intermediates in pharmaceutical and agrochemical development. Research has explored its utility in synthesizing derivatives with antimicrobial, anti-inflammatory, and antioxidant properties, expanding its potential in biomedical applications.

Additionally, α-methylcinnamaldehyde has shown promise in polymer chemistry. Its unsaturated structure makes it reactive in polymerization processes, leading to the development of functionalized polymers with tailored mechanical and thermal properties. These materials find applications in coatings, adhesives, and other specialty products.

The compound has also been studied for its biological activities. Preliminary research suggests moderate antimicrobial efficacy against bacterial and fungal strains, indicating potential use in preservative systems. Its antioxidant capacity further supports its inclusion in cosmetic formulations where oxidative stability is crucial.

Although α-methylcinnamaldehyde is widely employed, precautions are necessary during its handling. It can cause irritation to the skin, eyes, and respiratory system, necessitating appropriate safety measures in industrial and laboratory environments. Regulations ensure its safe incorporation into consumer products.

Overall, 2-methyl-3-phenylprop-2-enal exemplifies the interplay between chemical reactivity and practical application, making it a cornerstone in multiple industries. Its versatility continues to drive research into new uses, ensuring its relevance in both commercial and scientific contexts.