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Cuminaldehyde

Cuminaldehyde, also known as 4-isopropylbenzaldehyde or p-cuminaldehyde, is a naturally occurring organic compound classified as an aromatic aldehyde with the molecular formula C₁₀H₁₂O and a molar mass of 148.205 g/mol.^[1] It features a benzaldehyde core substituted by an isopropyl group at the para position, appearing as a colorless to pale yellow liquid with a strong, pungent odor reminiscent of cumin.^[2] This volatile compound serves as the primary bioactive constituent in the essential oil of cumin seeds (Cuminum cyminum), contributing significantly to the plant's characteristic aroma and flavor.^[3] Chemically, cuminaldehyde exhibits key physical properties including a boiling point of 235–236 °C, a density of 0.977 g/mL at 25 °C, and a flash point of 200 °F, making it suitable for applications requiring thermal stability.^[2] It is sparingly soluble in water but miscible with organic solvents like ethanol and ether, and it can be synthesized through the reduction of 4-isopropylbenzoyl chloride or oxidation of p-cymene.^[3] Beyond cumin, trace amounts occur in essential oils from plants such as eucalyptus, myrrh, and cassia, where it acts as a volatile flavor contributor.^[4] Cuminaldehyde finds extensive commercial use as a flavoring agent in foods, imparting a warm, spicy note to products like taco seasonings and beverages, while its pleasant aroma supports applications in perfumes, cosmetics, and fragrances.^[5] It also demonstrates insecticidal properties, functioning as a natural repellent against pests.^[1] Pharmacologically, the compound exhibits diverse biological activities, including antimicrobial effects against food-borne pathogens like Staphylococcus aureus and Escherichia coli, antioxidant capabilities, and potential antidiabetic, anti-inflammatory, and anticancer benefits, positioning it as a promising candidate for therapeutic development.^[6]^[7] These attributes underscore its role in both traditional medicine and modern pharmaceutical research.^[8]

Natural occurrence and production

Occurrence in nature

Cuminaldehyde is primarily found as a major constituent in the essential oil of cumin seeds (Cuminum cyminum L.), where it comprises 20–40% of the total oil and imparts the characteristic spicy, earthy aroma to the spice.^[9]^[10] This compound occurs in the seeds of the cumin plant, an annual herb native to the Mediterranean region and widely cultivated in India, Turkey, and Iran for its aromatic properties. In addition to cumin, cuminaldehyde occurs in the essential oils of other plants, including eucalyptus species (Eucalyptus spp.), myrrh (Commiphora myrrha), and cassia (Cinnamomum cassia), typically as a minor or trace constituent. These amounts contribute subtly to the overall volatile profile of these oils, enhancing their complex scents used in traditional medicine and perfumery.^[5] Cuminaldehyde is biosynthesized in plants through the monoterpenoid pathway. It begins with the methylerythritol phosphate (MEP) pathway producing geranyl pyrophosphate (GPP), which is converted to γ-terpinene by terpene synthases. γ-Terpinene is then aromatized to p-cymene, followed by oxidation to cuminaldehyde via cytochrome P450 enzymes in specialized glandular tissues, such as those in cumin seeds.^[11]^[12] In its natural context, cuminaldehyde, as part of the plant's volatile profile, may contribute to ecological roles such as attracting pollinators and deterring herbivores, similar to other aromatic compounds. It also exhibits antimicrobial properties against bacterial pathogens, potentially aiding in seed protection and enhancing plant survival and propagation in arid environments.^[13]^[14]

Commercial production

Over 90% of commercial cuminaldehyde is produced synthetically due to its cost efficiency and ability to provide consistent quality and supply, with major producers including Mitsubishi Gas Chemical Company.^[5]^[15] Natural sourcing is limited to extraction from cumin essential oil, which meets less than 10% of market demand; global cumin seed production was estimated at 900,000–1,000,000 metric tons annually as of 2022, yielding approximately 3–4% essential oil by weight, of which cuminaldehyde constitutes 30–50%.^[16]^[17] The aroma chemicals industry produces cuminaldehyde on the scale of thousands of tons per year to support flavor and fragrance applications, with bulk pricing typically ranging from $20–50 per kilogram depending on purity and volume. As of 2024, the global cuminaldehyde market is valued at approximately USD 500 million.^[18]^[19] Commercial grades achieve 98–99% purity, supplied as colorless to pale yellow liquids suitable for industrial use in the flavor and fragrance sectors.^[15]^[20]

Chemical properties

Structure and nomenclature

Cuminaldehyde is an organic compound characterized by a benzaldehyde core featuring an isopropyl substituent at the para position, giving it the systematic name 4-isopropylbenzaldehyde.^[1] Its preferred IUPAC name is 4-(propan-2-yl)benzaldehyde, reflecting the standard nomenclature for substituted benzaldehydes where the propan-2-yl group denotes the branched isopropyl chain.^[3] The molecular formula of cuminaldehyde is C₁₀H₁₂O, consistent with its structure comprising a benzene ring, an aldehyde functional group, and the alkyl substituent.^[21] The common name "cuminaldehyde" originates from its association with cumin (Cuminum cyminum), the plant source from which it is chiefly derived, combined with the suffix "-aldehyde" in line with International Scientific Vocabulary conventions for naming aldehydes.^[22] In structural representation, cuminaldehyde is denoted by the SMILES string CC(C)c1ccc(C=O)cc1, which captures the para-substituted arrangement: the isopropyl group (CC(C)) attached to the benzene ring (c1ccc cc1) opposite the formyl group (C=O).^[23] This configuration positions the bulky isopropyl moiety to influence the molecule's aromatic profile without introducing asymmetry. Cuminaldehyde exists as the para isomer of isopropylbenzaldehyde, distinct from the ortho and meta isomers that may occur in trace amounts but are not typically utilized in the same applications due to differing steric and electronic properties.^[24] The isopropyl substituent lacks a chiral center, as its central carbon bears two identical methyl groups, rendering the molecule achiral overall.^[1]

Physical properties

Cuminaldehyde appears as a colorless to pale yellow oily liquid and possesses a strong, pungent, spicy, green, herbaceous odor characteristic of cumin.^[1] Its density is 0.978 g/cm³ at 20 °C.^[15] The boiling point is 235.5 °C at 760 mmHg.^[1] Cuminaldehyde is insoluble in water, with a solubility of less than 0.3 g/L at 20 °C, but it is miscible with ethanol, diethyl ether, and other organic solvents.^[25] Additional physical characteristics include a refractive index of 1.529–1.534 at 20 °C, a flash point of 93 °C, and low vapor pressure (approximately 0.02 mmHg at 25 °C, indicating stability under ambient conditions).^[2]^[26]^[27] In infrared (IR) spectroscopy, cuminaldehyde exhibits a characteristic carbonyl (C=O) stretch at approximately 1700 cm⁻¹, along with aromatic C-H stretches around 3000–3100 cm⁻¹ and aliphatic C-H stretches near 2960 cm⁻¹.^[28] In nuclear magnetic resonance (¹H NMR) spectroscopy (in CDCl₃), key signals include the aldehyde proton at δ 9.95 (s, 1H), aromatic protons at δ 7.3–7.9 (m, 4H), the isopropyl methine at δ 2.92 (septet, 1H), and the isopropyl methyl groups at δ 1.25 (d, 6H).^[29]

Synthesis

Natural extraction

Cuminaldehyde is primarily isolated from natural sources using laboratory and small-scale techniques, with the main approach being steam distillation of crushed seeds from Cuminum cyminum (cumin), the richest natural source. This method extracts the essential oil, which contains cuminaldehyde as its dominant component. The process begins with crushing the dried seeds to increase surface area and facilitate volatile release, followed by hydrodistillation where steam at 100-110°C is passed through the material for 3-4 hours. The vapors condense, separating the essential oil layer, which typically yields 2–3.5% oil by seed weight, with cuminaldehyde comprising 30–50% of that oil.^[30]^[31]^[32] To purify cuminaldehyde from the crude essential oil, fractional distillation is employed, targeting the compound's boiling range of 230-240°C under reduced pressure to minimize decomposition. This step achieves typical purities of 80-90%, suitable for analytical or small-scale applications. Yield optimization can be accomplished through pretreatments, such as enzymatic hydrolysis with cellulase, pectinase, or protease, which disrupt cell walls and enhance volatile liberation, boosting oil yields from a baseline of 2.7% to 3.2-3.3%. Solvent pretreatments, like brief exposure to non-polar solvents, may further aid release without altering the oil profile significantly.^[33]^[31] Alternative natural sources, such as eucalyptus (Eucalyptus spp.) and myrrh (Commiphora myrrha), contain cuminaldehyde in trace amounts and are extracted via solvent methods like hexane immersion followed by evaporation. These yield lower concentrations (<5% cuminaldehyde relative to total extract), making them less efficient than cumin for isolation.^[34]^[35]

Synthetic methods

Cuminaldehyde can be synthesized through formylation of cumene (isopropylbenzene) using the Gattermann-Koch reaction, which involves passing carbon monoxide and hydrogen chloride gases through cumene in the presence of aluminum chloride and cuprous chloride catalysts under high pressure. This electrophilic aromatic substitution introduces the formyl group para to the isopropyl substituent, yielding cuminaldehyde with reported efficiencies around 49-70% depending on conditions. An alternative formylation approach employs the Vilsmeier-Haack reaction with dimethylformamide and phosphorus oxychloride, though it is less commonly applied to alkylbenzenes like cumene due to moderate activation of the ring. Reduction-based routes provide another key pathway, such as the Rosenmund reduction of 4-isopropylbenzoyl chloride using hydrogen gas and palladium on barium sulfate (poisoned with sulfur or quinoline to prevent over-reduction to the alcohol), which selectively converts the acid chloride to the aldehyde. Yields for this method typically exceed 70% under controlled conditions. Similarly, diisobutylaluminum hydride (DIBAL-H) reduction of the corresponding benzoate esters, such as methyl 4-isopropylbenzoate, at low temperatures (-78°C) followed by hydrolytic workup affords cuminaldehyde by halting the reduction at the aldehyde stage, offering a milder alternative suitable for sensitive substrates. Synthesis from p-cymene (1-isopropyl-4-methylbenzene) involves selective side-chain oxidation of the methyl group to the aldehyde, often via anodic oxidation in methanolic solution to form the dimethyl acetal intermediate, which is then hydrolyzed under acidic conditions. This electrochemical method achieves moderate yields (up to 40%) while minimizing over-oxidation to the carboxylic acid, and may proceed through hydroperoxide-like intermediates analogous to those in ethylbenzene oxidations. Other approaches include manipulation of the side chain, such as initial bromination followed by controlled hydrolysis. Additional methods encompass the reaction of the Grignard reagent derived from 1-bromo-4-isopropylbenzene with N,N-dimethylformamide, yielding cuminaldehyde after acidic hydrolysis (overall yields ~60-70%), and variants involving Cannizzaro disproportionation of related non-enolizable aldehydes or gem-dichlorides to generate the target from precursors like cuminic acid derivatives. These synthetic routes are favored for industrial scalability over natural extraction, with multi-step processes generally providing overall yields of 60-80% and enabling cost-effective production from petroleum-derived starting materials like cumene.

Applications

In flavors and fragrances

Cuminaldehyde is widely utilized as a flavoring agent to impart a characteristic spicy, cumin-like profile to various food products. It is typically incorporated at concentrations of 0.4 to 4 ppm in baked goods, beverages, condiments, hard candies, and frozen dairy items, enhancing the herbal and green notes in spicy formulations such as curries, pickles, and oriental-style dishes.^[4] This application also extends to vegetable, dill, caraway, and cake flavors, where it contributes woody and herbaceous depth without overpowering other ingredients.^[36] In the fragrance sector, cuminaldehyde functions as a core component in perfumes, particularly masculine colognes, soaps, and lotions, employed at usage levels of 0.01 to 1% to deliver warm, spicy accords with animalic undertones.^[37] It excels in blending with citrus and herbal elements, providing stability and longevity in oriental, fougère, and chypre compositions, while adding a green, herbaceous edge to overall scent profiles.^[38] The compound's sensory attributes include a high-strength, spicy odor with cumin, green, and herbal facets, making it effective even at trace levels in formulations.^[4] Furthermore, cuminaldehyde supports antioxidant preservation in flavored products by scavenging free radicals and inhibiting lipid oxidation, thereby extending shelf life in spice-infused foods.^[10]^[39] Major suppliers like Givaudan and Firmenich provide cuminaldehyde for industrial applications, where it represents a primary active in many cumin-derived aroma compounds used across food and cosmetic sectors.^[38]^[40]

Biological and pharmaceutical uses

Cuminaldehyde displays notable antimicrobial activity against several bacterial pathogens, including Escherichia coli and Staphylococcus aureus, by disrupting cell membrane integrity and interfering with genomic DNA.^[41]^[42] This mechanism enables its application in food preservation, where it helps control microbial growth in products like sauced beef and peanuts, contributing to extended shelf life without synthetic additives.^[41]^[43] In addition to antibacterial effects, cuminaldehyde exhibits insecticidal properties, particularly as a larvicidal agent against mosquito species such as Culex pipiens, with reported LC₅₀ values around 50–100 ppm depending on formulation.^[44]^[45] It is incorporated into natural insect-repellent formulations, leveraging its toxicity to larvae and adults to support vector control efforts.^[44] Cuminaldehyde holds promise in neurological applications by inhibiting α-synuclein fibrillation, a key pathological process in Parkinson's disease, with an IC₅₀ of approximately 100 μM.^[46] Studies from 2015 demonstrated its ability to modulate fibrillation and reduce associated cytotoxicity, positioning it as a potential lead for neuroprotective therapies.^[46]^[47] Beyond these targeted effects, cuminaldehyde contributes to the antioxidant capacity observed in cumin extracts, scavenging free radicals and mitigating oxidative stress.^[48] Derivatives such as thiosemicarbazones have shown antiviral activity, including inhibition of viral enzymes in SARS-CoV-2.^[49] Recent reviews as of 2025 highlight its potential in novel delivery systems for enhanced bioavailability in antidiabetic and anticancer applications.^[50] It also presents potential as a drug candidate for gastrointestinal conditions like colic and dyspepsia, based on traditional uses supported by preliminary pharmacological evaluations.^[6] Overall, research on cuminaldehyde remains predominantly at the preclinical stage, with no approved pharmaceutical products as of 2025.^[6]

Safety and toxicology

Hazards

Cuminaldehyde exhibits moderate acute toxicity, with an oral LD50 of 1390 mg/kg in rats, classifying it as harmful if swallowed under GHS category H302.^[51] It causes skin irritation (H315) and serious eye damage or irritation (H319) upon contact.^[51] Additionally, it may provoke allergic skin reactions (H317) in sensitized individuals, particularly through dermal exposure in fragrance applications.^[1] Inhalation of cuminaldehyde vapors can lead to respiratory tract irritation at high concentrations, with a GHS classification of harmful if inhaled (H332); the no-observed-adverse-effect concentration for local respiratory effects is 217 mg/m³.^[51]^[52] Prolonged or repeated skin contact may result in dermatitis.^[53] As a combustible liquid (H227), cuminaldehyde has a flash point of 93°C, posing a fire hazard under conditions involving heat or open flames.^[54]^[51] Cuminaldehyde is harmful to aquatic life (H402), with a fish LC50 of 40.2 mg/L indicating potential acute toxicity to aquatic organisms.^[52] It exhibits moderate bioaccumulation potential, with a log Kow of 3.17 and a bioconcentration factor of 57 L/kg, and shows good biodegradability (86% in 28 days per OECD 301F), though low water solubility may contribute to persistence in sediment.^[52] Regarding chronic effects, cuminaldehyde is not classified as a carcinogen by the International Agency for Research on Cancer (IARC Group 3 or unclassified), with no evidence of genotoxicity in Ames tests or read-across from related compounds.^[52] Toxicology data on potential endocrine disruption remains limited, with exposures in fragrance use well below thresholds of toxicological concern.^[52]

Regulatory information

Cuminaldehyde is classified under the Globally Harmonized System (GHS) as a warning substance with the exclamation mark pictogram (GHS07). Its hazard statements include H302 (harmful if swallowed), H315 (causes skin irritation), H317 (may cause an allergic skin reaction), H319 (causes serious eye irritation), and H402 (harmful to aquatic life). Relevant precautionary statements are P264 (wash thoroughly after handling), P280 (wear protective gloves, protective clothing, eye protection, or face protection), and P305 + P351 + P338 (if in eyes: rinse cautiously with water for several minutes; remove contact lenses if present and easy to do; continue rinsing). In food and flavor applications, cuminaldehyde holds Generally Recognized as Safe (GRAS) status from the U.S. Food and Drug Administration (FDA) as a synthetic flavoring substance under 21 CFR 172.515.^[55] It is also approved in the European Union under the FLAVIS system (number 05.024) for use as a flavoring agent, with maximum levels typically up to 5 mg/kg in finished foods.^[4] For cosmetic use, the International Fragrance Association (IFRA) standards restrict cuminaldehyde to 0.47% in leave-on products due to its potential for skin sensitization.^[52] In the EU, it is registered under the REACH regulation with EC number 204-516-9, requiring compliance with safety data assessments for industrial and consumer applications. Environmentally, the U.S. Environmental Protection Agency (EPA) lists cuminaldehyde as active on the Toxic Substances Control Act (TSCA) inventory, indicating low concern for persistence and bioaccumulation, with no specific bans but subject to general wastewater discharge limits under TSCA reporting.^[56] Safe handling guidelines recommend storage in a cool, dry, well-ventilated area away from heat sources and incompatible materials. Personal protective equipment (PPE) includes chemical-resistant gloves, safety goggles, and protective clothing to prevent skin and eye contact.^[57] In case of ingestion, do not induce vomiting and seek immediate medical attention; for inhalation, move to fresh air and provide oxygen if breathing is difficult.

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Odour. No data available. Odour Threshold. No data available. pH. No data available. Melting point/freezing point. Melting point/range: -50,5 °C. Initial ...Missing: odor | Show results with:odor<|control11|><|separator|>
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Synthetic flavoring substances and adjuvants may be safely used in food in accordance with the following conditions.
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Signal word. Warning. Hazard statements. H302-Harmful if swallowed. H315-Causes skin irritation. H319-Causes serious eye irritation.