Perillaldehyde

• CAS: 2111-75-3
• Catalog Number: ACM2111753
• Category: Main Products
• Molecular Weight: 150.22
• Molecular Formula: C₁₀H₁₄O
• IUPAC Name: 4-prop-1-en-2-ylcyclohexene-1-carbaldehyde
• Canonical SMILES: CC(=C)C1CCC(=CC1)C=O
• InChI Key: RUMOYJJNUMEFDD-UHFFFAOYSA-N
• Boiling Point: 238ºC at 760 mmHg
• Flash Point: 95.6ºC
• Density: 0.967 g/mL at 20ºC(lit.)
• Appearance: Pale, yellowish oily liquid; powerful, fatty-spicy, oily-herbaceous odour
• EC Number: 218-302-8
• Exact Mass: 150.10400
• Hazard Statements: Xi: Irritant
• Safety Description: 26

Case Study

Genotoxicity evaluation of the flavoring agent perillaldehyde

Hobbs, Cheryl A., et al. Food and Chemical Toxicology 97 (2016): 232-242.

Perillaldehyde, a natural monocyclic terpenoid most abundant in the perilla herb, has long been used as a flavoring ingredient to add spicy and citrus flavors to foods. Perillaldehyde was tested in bacterial reverse mutation assays, in vitro micronucleus assays in human lymphocytes, HPRT assays in mouse lymphoma cells, and micronucleus/comet assays in Han Wistar rats. In contrast to previously published results, perillaldehyde induced mutations in the TA98 strain of Salmonella typhimurium in the absence of metabolic activation. The comet assay was negative for the duodenum and weakly positive for the liver, but only at hepatotoxic doses of perillaldehyde. All other genotoxicity test results were negative. These data do not indicate any genotoxicity of perillaldehyde and they provide the main basis for the recent scientific opinions on the genotoxicity of perillaldehyde issued by several international organizations responsible for the safety assessment of food additives and flavorings.
For pre-incubation tests, perillaldehyde or control preparations, bacteria, and 10% S9 mixture were mixed and incubated at 37 ± 1°C for 1 hour before adding molten agar and inoculation. After setting, three plates of each concentration (five plates for vehicle control) were incubated at 37°C in the dark for 3 days. Colonies were counted when confounding factors such as precipitation affected the accuracy of the automated counter. Background was checked for signs of toxicity.

In vivo and in vitro mutagenicity studies of perillaldehyde

Honma, Masamitsu, et al. Genes and Environment 43 (2021): 1-11.

Perillaldehyde and cinnamaldehyde are natural substances found in plants and used as flavoring ingredients. These compounds are expected to be DNA reactive due to the presence of α,β-unsaturated aldehydes in their structures. Their genotoxic potential is currently controversial. To elucidate the mutagenicity of perillaldehyde and cinnamaldehyde, we performed in silico quantitative structure-activity relationship (QSAR) analysis, in vitro Ames test, and in vivo transgenic rodent gene mutation (TGR) assay. The data clearly showed that there was no evidence that perillaldehyde and cinnamaldehyde (administered up to 1000 mg/kg/day) had mutagenic potential in mice in vivo; however, cinnamaldehyde was mutagenic in vitro.
Administration of perillaldehyde began at 9 weeks of age. Six mice were treated with 125, 250, 500, or 1000 mg/kg/day of perillaldehyde by oral gavage using corn oil as a vehicle for 28 days. Three days after the last treatment, the liver and glandular stomach were each collected and stored. As a positive control group, mice were injected intraperitoneally (i.p.) with N-ethyl N-nitrosourea (ENU) 100 mg/kg/day for 2 consecutive days. Genomic DNA was extracted from the liver and glandular stomach (whole tissue) using the phenol/chloroform method.

Study on the antibacterial effect and mechanism of perillaldehyde and its stabilization and encapsulation technology for fruit preservation

Kang, Chen, et al. Postharvest Biology and Technology 207 (2024): 112613.

Perillaldehyde (PAE) is an essential oil extracted from Perilla frutescens with excellent antioxidant and antibacterial activities. In this study, the antifungal mechanism of perillaldehyde was attributed to the stimulation of ROS levels, the destruction of mitochondrial function and the induction of spore apoptosis. Transcriptome analysis showed that the gene expression pattern of Botrytis cinerea changed significantly after perillaldehyde treatment, and the differentially expressed genes (DEGs) were mainly involved in the MAPK signaling pathway and the cell wall integrity pathway. In order to better utilize perillaldehyde for fruit preservation, the inclusion complex (IC) of PAE and hydroxypropyl-β-cyclodextrin was successfully synthesized by ultrasound-assisted method, and the inclusion complex was proved to be feasible by UV-visible spectroscopy, Fourier transform infrared spectroscopy, thermal property analysis, scanning electron microscopy and H NMR. The results showed that the water solubility and thermal stability of perillaldehyde/HPβCD-IC were significantly improved compared with pure perillaldehyde. Both in vitro and in vivo antibacterial tests showed that perillaldehyde/HPβCD-IC had a good inhibitory effect on B. cinerea, indicating that perillaldehyde/HPβCD-IC had good antibacterial effect, water solubility and thermal stability, which provided a theoretical basis for the use of perillaldehyde/HPβCD-IC in fruit preservation.
The perillaldehyde/HPβCD inclusion complex was prepared by ultrasonic-assisted method. First, 67.82 g HPβCD was added to 200 mL 20% ethanol phosphate buffer (pH = 6.8) and stirred, and then 13.22 mL perillaldehyde-ethanol solution (containing 6.61 g perillaldehyde) was added under magnetic stirring. Then, ultrasonic treatment was performed for 30 minutes to form the inclusion complex. Finally, the mixed solution was freeze-dried for 3 days and ground into fine powder for further experiments. The in vitro antifungal activity of perillaldehyde/HPβCD-IC was evaluated on PDA plates, and the in vivo antifungal activity of perillaldehyde/HPβCD-IC was performed on tomato and strawberry fruits.

Study on the photochemical reaction of perillaldehyde under different conditions

Tateba, Hideki, et al. Bioscience, biotechnology, and biochemistry 56.4 (1992): 614-619.

Perillaldehyde was photoirradiated by a 400 W high pressure mercury lamp under various conditions. In MeOH, it was degraded under N2 flow to obtain two new MeOH adducts and a new methyl ether, while perillaldehyde was also converted to dimethyl acetal and oxidation products. In EtOAc, perillaldehyde disappeared and two new dimers were produced under flow, while perillaldehyde was converted to two oxygenated products, including a new compound under O2 flow. In the presence of Bengal rose, perillaldehyde was converted by visible light in MeOH under stream. Photosensitization of RB was observed under O2 flow, and two new oxygenated products were formed. Perillaldehyde was relatively stable in n-hexane under N2 flow or in the presence of RB under O2 flow.
Methanol solution (300 ml) containing perillaldehyde (1.0 g) was irradiated in a container with a water-cooled 400 W high pressure mercury lamp under N2 flow for 5 h. After evaporation of the solvent, the residual oil was subjected to HPLC. The eluent was separated into MW 350, MW 350-250 and MW <250.

Custom Q&A

What is the IUPAC name of (-)-Perillaldehyde?

The IUPAC name of (-)-Perillaldehyde is (4S)-4-prop-1-en-2-ylcyclohexene-1-carbaldehyde.

What is the molecular weight of (-)-Perillaldehyde?

The molecular weight of (-)-Perillaldehyde is 150.22 g/mol.

What is the InChIKey of (-)-Perillaldehyde?

The InChIKey of (-)-Perillaldehyde is RUMOYJJNUMEFDD-SNVBAGLBSA-N.

What is the CAS number of (-)-Perillaldehyde?

The CAS number of (-)-Perillaldehyde is 18031-40-8.

How many hydrogen bond donor count does (-)-Perillaldehyde have?

(-)-Perillaldehyde has 0 hydrogen bond donor count.

How many hydrogen bond acceptor count does (-)-Perillaldehyde have?

(-)-Perillaldehyde has 1 hydrogen bond acceptor count.

How many rotatable bond count does (-)-Perillaldehyde have?

(-)-Perillaldehyde has 2 rotatable bond count.

What is the topological polar surface area of (-)-Perillaldehyde?

The topological polar surface area of (-)-Perillaldehyde is 17.1Ų.

How many heavy atoms does (-)-Perillaldehyde have?

(-)-Perillaldehyde has 11 heavy atoms.

Is (-)-Perillaldehyde a canonicalized compound?

Yes, (-)-Perillaldehyde is a canonicalized compound.