Cyclamen aldehyde
[CAS# 103-95-7]

Identification

• Classification: Pharmaceutical intermediate >> Heterocyclic compound intermediate >> Pyrimidine compound >> Aldehyde intermediate
• Name: Cyclamen aldehyde
• Synonyms: 2-methyl-3-(4-propan-2-ylphenyl)propanal
• Molecular Formula: C₁₃H₁₈O
• Molecular Weight: 190.28
• CAS Registry Number: 103-95-7
• EC Number: 203-161-7
• SMILES: CC(C)C1=CC=C(C=C1)CC(C)C=O

Properties

• Density: 0.9±0.1 g/cm³ Calc.^*
• Boiling point: 266.1±9.0 ºC 760 mmHg (Calc.)^*, 270 ºC (Expl.)
• Flash point: 116.7±10.2 ºC (Calc.)^*
• Index of refraction: 1.497 (Calc.)^*, 1.505 (Expl.)

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

Safety Data

• Hazard Symbols: GHS07;GHS08;GHS09 Warning
• Hazard Statements: H315-H317-H361-H411-H412
• Precautionary Statements: P203-P261-P264-P272-P273-P280-P302+P352-P318-P321-P332+P317-P333+P317-P362+P364-P391-P405-P501

Hazard Classification

Hazard	Class	Category Code	Hazard Statement
Skin irritation	Skin Irrit.	2	H315
Skin sensitization	Skin Sens.	1B	H317
Chronic hazardous to the aquatic environment	Aquatic Chronic	3	H412
Skin sensitization	Skin Sens.	1	H317
Chronic hazardous to the aquatic environment	Aquatic Chronic	2	H411
Reproductive toxicity	Repr.	2	H361
Chronic hazardous to the aquatic environment	Aquatic Chronic	1	H410
Acute hazardous to the aquatic environment	Aquatic Acute	1	H400
Eye irritation	Eye Irrit.	2	H319
Reproductive toxicity	Repr.	2	H361fd

Discovory and Applicatios

Cyclamen aldehyde, also known by its IUPAC name 3-(4-isopropylphenyl)-2-methylpropanal, is an aromatic aldehyde widely used in the fragrance and flavor industry. It belongs to the family of aliphatic-aromatic aldehydes and is recognized for its pleasant floral scent, which closely resembles the aroma of the cyclamen flower—hence its name. Its molecular structure comprises a substituted benzene ring bearing an isopropyl group and a side chain consisting of a methyl group and an aldehyde function on a three-carbon backbone.

Cyclamen aldehyde was first synthesized in the early 20th century during investigations into aromatic aldehydes for perfumery applications. It emerged from a broader effort to identify synthetic alternatives to natural floral scents, particularly those that could replicate the delicate and fresh odor of cyclamen. The compound became commercially important after it was discovered that its scent was not only pleasing and stable but also suitable for a wide range of consumer products. It gained favor among perfumers for its long-lasting and soft floral-woody profile.

The main use of cyclamen aldehyde is as a fragrance ingredient. It is a common component in perfumes, soaps, shampoos, and other personal care products. Due to its ability to impart a clean and subtly sweet scent, it is often used in combination with other aldehydes, musks, or floral notes to create complex fragrance compositions. The compound is valued not just for its individual odor but also for its performance in various formulations, especially in terms of stability and compatibility with other ingredients.

In addition to personal care products, cyclamen aldehyde is utilized in household cleaning agents and air fresheners. It helps mask undesirable odors and provides a sense of cleanliness and freshness. Because of its relatively low volatility and good tenacity, it remains effective over time in both water-based and alcohol-based formulations. Its performance in these applications has been validated by repeated use in commercial cleaning and hygiene products over decades.

Cyclamen aldehyde is also used, to a lesser extent, in the flavor industry, although its applications here are more limited compared to fragrances. It may be included in trace amounts in certain food products or beverages where floral notes are desired. However, its use in flavors is tightly regulated due to its classification and required safety assessments by food safety authorities.

The safety and toxicological profile of cyclamen aldehyde have been extensively studied. It has been evaluated by the International Fragrance Association (IFRA) and other regulatory bodies, which have established usage guidelines and concentration limits to ensure consumer safety. When used within these regulatory frameworks, the compound is considered safe for use in cosmetics and personal care products. Nonetheless, like many fragrance compounds, it may cause sensitization or allergic reactions in some individuals, and thus, appropriate labeling and formulation precautions are taken by manufacturers.

Overall, cyclamen aldehyde represents a successful example of a synthetic fragrance ingredient that combines desirable olfactory characteristics with versatility in application. Its discovery and development have significantly contributed to modern perfumery and product formulation, offering a stable, cost-effective, and appealing alternative to natural floral extracts. Through decades of use, it has maintained a strong presence in both fine and functional fragrance sectors, highlighting its lasting value and reliability in the fragrance industry.

References

2014. Functionalized MCM-41 as a catalyst for the aldol condensation of 4-isopropylbenzaldehyde and propanal. Reaction Kinetics, Mechanisms and Catalysis, 114(1).
DOI: 10.1007/s11144-014-0811-2

2015. Cyclamen aldehyde synthesis: aldol condensation followed by hydrogenation over ruthenium catalyst. Research on Chemical Intermediates, 41(11).
DOI: 10.1007/s11164-015-1948-y

2016. A synthetic route to 4-alkyl-alpha-methylhydrocinnamylaldehydes. Research on Chemical Intermediates, 43(5).
DOI: 10.1007/s11164-016-2782-6