2-Methyl-3-(3,4-methylenedioxyphenyl)propanal
[CAS# 1205-17-0]

Identification

• Classification: Flavors and spices >> Synthetic spice >> Aldehyde fragrance >> Aromatic aldehyde
• Name: 2-Methyl-3-(3,4-methylenedioxyphenyl)propanal
• Synonyms: helional
• Molecular Formula: C₁₁H₁₂O₃
• Molecular Weight: 192.21
• CAS Registry Number: 1205-17-0
• EC Number: 214-881-6
• SMILES: CC(CC1=CC2=C(C=C1)OCO2)C=O

Properties

• Density: 1.2±0.1 g/cm³, Calc.^*
• Index of Refraction: 1.538, Calc.^*, 1.534 (Expl.)
• Boiling Point: 286.0±9.0 ºC (760 mmHg), Calc.^*, 282 ºC (Expl.)
• Flash Point: 117.6±5.1 ºC, Calc.^*, 100 ºC (Expl.)

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

Safety Data

• Hazard Symbols: GHS07;GHS09 Warning
• Hazard Statements: H317-H411
• Precautionary Statements: P261-P272-P273-P280-P302+P352-P321-P333+P317-P362+P364-P391-P501

Hazard Classification

Hazard	Class	Category Code	Hazard Statement
Chronic hazardous to the aquatic environment	Aquatic Chronic	2	H411
Skin sensitization	Skin Sens.	1	H317
Skin sensitization	Skin Sens.	1B	H317
Reproductive toxicity	Repr.	2	H361
Reproductive toxicity	Repr.	2	H361fd
Eye irritation	Eye Irrit.	2	H319
Skin irritation	Skin Irrit.	2	H315
Specific target organ toxicity - single exposure	STOT SE	3	H335
Chronic hazardous to the aquatic environment	Aquatic Chronic	1	H411
Specific target organ toxicity - repeated exposure	STOT RE	2	H373

Discovory and Applicatios

2-Methyl-3-(3,4-methylenedioxyphenyl)propanal is an aromatic aldehyde that contains a methylenedioxyphenyl moiety, which is a common structural feature in various naturally occurring and synthetic compounds. It is a colorless to pale yellow liquid with an aldehyde functional group, contributing to its reactivity and applications in fragrance chemistry. The compound's molecular structure includes a substituted propanal framework, which influences its physicochemical properties such as volatility and solubility.

The discovery of 2-methyl-3-(3,4-methylenedioxyphenyl)propanal can be linked to research in fragrance chemistry and organic synthesis, where structurally related aldehydes have been identified and studied for their olfactory properties. Compounds containing the methylenedioxyphenyl moiety are commonly found in essential oils and natural extracts, leading to interest in their synthetic analogs for use in perfumery and flavoring. The synthesis of this aldehyde typically involves selective functionalization of precursor molecules, often employing methods such as alkylation, oxidation, and condensation reactions to achieve the desired structural configuration.

One of the primary applications of 2-methyl-3-(3,4-methylenedioxyphenyl)propanal is in the fragrance industry, where it is valued for its warm, woody, and slightly spicy aroma. It is used as a component in fine fragrances, personal care products, and household items to enhance scent profiles. Its olfactory characteristics make it suitable for blending with floral, woody, and balsamic notes, contributing to complex and long-lasting fragrance formulations. The aldehyde functional group in its structure also allows it to participate in various chemical reactions that modify its scent profile, making it a versatile ingredient in perfumery.

Beyond its role in fragrance applications, the compound may also be utilized in the synthesis of other aromatic compounds. The presence of the methylenedioxy group can influence its chemical reactivity, allowing for modifications that produce derivatives with tailored properties. Such modifications are relevant in the development of specialty chemicals used in different industrial applications, including fine chemicals and potentially pharmaceutical intermediates.

Research on structurally related compounds suggests that methylenedioxy-substituted aldehydes exhibit specific physicochemical behaviors, such as moderate volatility and stability under standard conditions. These properties make them suitable for controlled-release fragrance formulations and for applications requiring compounds with prolonged olfactory effects. The compound’s stability and compatibility with other fragrance ingredients contribute to its widespread use in commercial formulations.

Due to its presence in perfumery and related industries, 2-methyl-3-(3,4-methylenedioxyphenyl)propanal has been evaluated for its safety profile in consumer products. Regulatory agencies assess such compounds for potential sensitization, toxicity, and environmental impact to ensure their safe use. The compound's structural similarity to naturally occurring aromatic aldehydes suggests that it is used within established safety guidelines in fragrance formulations.

Overall, 2-methyl-3-(3,4-methylenedioxyphenyl)propanal is a significant compound in the field of fragrance chemistry. Its synthesis, olfactory properties, and applications in perfumery highlight its importance in the formulation of consumer products. Its reactivity and structural attributes continue to make it a subject of interest in organic synthesis and applied fragrance research.

References

2007. In vitro penetration and subchronic toxicity of alpha-methyl-1,3-benzodioxole-5-propionaldehyde. Food and chemical toxicology : an international journal published for the British Industrial Biological Research Association, 45(5).
DOI: 10.1016/j.fct.2006.09.017

2006. Evaluation of the Developmental Toxicity of a-Methyl-3,4-Methylene-Dioxyhydrocinnamic Aldehyde in Rats. International Journal of Toxicology, 25(2).
DOI: 10.1080/10915810600609312

2019. Optimal patch test concentration for three widely used sensitizing fragrance substances without mandatory labelling in cosmetics. Contact Dermatitis, 80(4).
DOI: 10.1111/cod.13202