Cinnamyl Cinnamate Research Articles

Inter-tree Variation in Chemical Components of North Sumatra Benzoin Gum (Styrax sp.)

Benzoin gum, which is known as Sumatra benzoin (Styrax sp), is widely used as an ingredient in the incense. Although these resins are widely used as flavours and fragrances, no studies have been made on inter-tree variation of its chemical composition. Therefore, benzoin gum samples were tapped from the 30 individual trees (age 10 years, 9~35 cm in diameter) grown in the community forest of Polung, Humbang Hasundutan Regency, North Sumatra. The gum chemical components were analyzed by GC-MS and identified by comparing the fragmentation pattern with the standard components and literature studies. It was found that the major compounds detected by GC-MS were cinnamic acid (51.48%), cinnamyl cinnamate (62.56%), benzoic acid (1.94%), chavicol (5.18%), benzyl cinnamic acid (7.8%), atropic acid (9.84%), and vanillin (1.47%). Two main constituents that were always detected from 30 benzoin trees were chavicol and cinnamic acid, followed by cinnamyl cinnamate (28 trees) and benzoic acid (14 trees). By cluster analysis, 30 samples of benzoin gum can be classified into clusters I - III based on the average chemical components. Cluster I consisted of 7 individual trees with a higher percentage of benzoic acid and chavicol but lower concentration of cinnamic acid compared to other clusters. Cluster II consisted of 18 individual trees with a high percentage of cinnamyl cinnamate whereas clusters III consisted of 5 individual trees characterized with a high percentage of cinnamic acid. By Pearson correlation, it was observed that no significant correlation between the values of diameter and the amount of chemical components of benzoin gum.

The Properties of Ethyl Acetate Extract of Frankincense (Styrax benzoin) Using the Maceration Method

This study aims to determine the standardization of ethyl acetate extract of frankincense gum using the maceration method. The method used in this study was to standardize the ethyl acetate extract of frankincense using specific and non-specific parameters. The results of standardization with specific parameters showed that the ethyl acetate extract of frankincense latex was blackish brown in color and had a distinctive odor of frankincense. It contained 86.5% soluble compound in ethanol. The results of standardization with non-specific parameters showed a specific gravity of 0.8213 g/ml and an average moisture content of 1.71%. The chemical components contained are Benzoic acid; Vanillin; transCinnamic acid; Phenol, 2-methoxy-4-propyl-; 2-Propanone, 1-(4) -hydroxy-3-methoxyphenyl)-; Benzoic acid, phenylmethyl ester; (Z)-Cinnamyl benzoate; 2-Propenoic acid, 3-phenyl-,phenylmethyl ester, (E) -; and Cinnamyl cinnamate.

Steglich Esterification of Activated Cinnamyl Cinnamate Derivatives and Computational Studies of Intramolecular Diels-Alder for Lignan Synthesis

A ryltetralin and arylnaphthalene lignans consisting of methylenedioxy or trimethoxy groups, such as podophyllotoxin and phyllanthusmin C, are known to have effective anticancer properties. The synthesis of these compounds can be achieved through intramolecular Diels-Alder reactions on cinnamyl cinnamate ester derivatives. Furthermore, this ester is commonly synthesized through an esterification reaction between cinnamoyl halide and cinnamyl alcohol. In this study, cinnamyl cinnamate only produced a 41% yield, while a nearly quantitative yield of 98% was obtained using the Steglich reaction with N,N’-dicyclohexylcarbodiimide and 4-dimethylaminopyridine. This reaction was used to synthesize eight cinnamyl cinnamate ester derivatives, which consisted of methylenedioxy and trimethoxy groups, following a combinatorial synthesis. 3,4-Methylenedioxy- and 3,4,5-trimethoxycinnamyl alcohols were obtained by reducing methyl 3,4-methylenedioxycinnamate and 3,4,5-trimethoxycinnamic acid, respectively. The results showed that the ester yields were excellent, except for the ester derivatives of 3,4,5-trimethoxycinnamyl alcohol. This alcohol was unstable during column chromatography, leading to the direct esterification of the crude reduction products. A side product with Rf adjacent to the ester was obtained, thereby reducing the ester yield. The identification of this by-product and the intramolecular Diels-Alder reaction on the products obtained were described in this study. Computational studies showed that transforming reactants into products led to the production of one intermediate compound and two transition states (TS). Each TS represented the intramolecular Diels-Alder cycloaddition reaction and migration of [1,3]-hydrogen. Thermodynamic studies consistently revealed that a solvent environment could effectively reduce the activation energy associated with a chemical process.

Chemical Composition and Evaluation of Antibacterial, Antibiofilm, and Mutagenic Potentials of a Propolis Sample from the Atlantic Forest of Midwest Brazil.

Sixteen triterpenoids with various skeletal types, five phenylpropanoid derivatives, and two flavonoids were isolated from a propolis sample produced by Apis mellifera collected in the Atlantic Forest of Midwest Brazil. Among these compounds, six triterpenes, namely 3β,20R-dihydroxylanost-24-en-3-yl-palmitate, (23E)-25-methoxycycloartan-23-en-3-one, 24-methylenecycloartenone, epi-lupeol, epi-α-amyrin, and epi-β-amyrin are being reported for the first time in propolis, while cycloartenone, (E)-cinnamyl benzoate, and (E)-cinnamyl cinnamate are new findings in Brazilian propolis. The presence of cycloartane- and lanostane-type triterpenoids, the latter being a class of compounds of restricted distribution in propolis worldwide, has not been reported in propolis from Midwest Brazil until now. The ethyl acetate phase obtained from the ethanol extract was effective in preventing biofilm formation by Staphylococcus aureus, with an inhibition rate of about 96 % at 0.5 mg.mL-1 , and with quercetin isolated as one of its active constituents. In contrast, the hexane phase exhibited notable antibacterial activity against Pseudomonas aeruginosa, inhibiting bacterial growth by 92 % at 0.5 mg.mL-1 ; however, none of the triterpenoids isolated from this phase proved active against this pathogen. The ethanol extract was neither toxic nor mutagenic at the concentrations tested, as determined by the in vivo SMART assay on Drosophila melanogaster, even under conditions of high metabolic activation.

Aryltetralin lignans from Hyptis brachiata inhibiting T lymphocyte proliferation

Increased activation and proliferation of T lymphocytes plays an essential role in the development of chronic inflammation and autoimmune diseases. Currently used immunosuppressive drugs often do not provide long-lasting relief of symptoms and show a gradual loss of efficacy over time, and are accompanied by various side effects. Therefore, novel immunosuppressive lead substances are needed. For this purpose, an in-house library consisting of 600 extracts of plants from Panama was screened for inhibition of human T lymphocyte proliferation. As one of the hits, an ethyl acetate extract from the aerial parts of Hyptis brachiata (Lamiaceae) exhibited strong inhibitory effects. Subsequent investigation resulted in the isolation of seven aryltetralin lignans, five arylnaphthalene lignans, two flavonoids, three triterpenes, and cinnamyl cinnamate. Aryltetralin lignans inhibited T lymphocyte proliferation in a concentration-dependent manner without induction of apoptosis. No relevant inhibition was observed for the arylnaphthalene lignans, flavonoids, and triterpenes. Additional cell cycle arrest investigations revealed that isolated aryltetralin lignans potently inhibited cell division in G2/M phase similarly to podophyllotoxin. Multifluorescence panel analyses of the extract also showed weak suppressive effects on the production of IL-2 and TNF-α. Therefore, preparations made out of H. brachiata could be further explored as an interesting herbal alternative in the treatment of autoimmune diseases.

Chemical Structure and Antifungal Activity of Agean Region of Propolis in Türkiye

The chemical composition of propolis from Aegean Uşak (Balcıdamı and Kaşbelen), Afyon ( Emirdağ and Dinar), Manisa (Salihli and Kula), Denizli (Merkez and Çivril), Muğla (Milas and Merkez), İzmir (Kemalpaşa and Menemen), Aydın (Söke and Kuşadası) and Kütahya (Hisarcık and Tavşanlı) was studied in order to determine the major compounds by using GC-MS. In this study, 8 % ethanol extract of propolis prepared by mixing 920 ml of 70 % ethanol and 80 g of propolis was used. Chemical analysis of propolis extracts indicated that the propolis samples had high concentrations of the aromatic acids, esters and other derivatives which are responsible for the antibacterial, antifungal, antiviral, anti-inflammatory and anti-cancer properties of propolis such as benzyl cinnamate, methyl cinnamate, caffeic acid, cinnamyl cinnamate and cinnamoylglcine besides the most common compounds as fatty acid, terpenoids, esters, alcohols hydrocarbons and aromatic acids. Also, in this research the antifungal effects of 7 concentrations (6.25, 12.5, 25, 50 ppm) of propolis ethanol extract (PEE) against Fusarium oxysporum was investigated in vitro conditions. Propolis was mixed alone or in combination with potato dextrose agar (PDA) medium at various concentrations. The results indicated that the mycelial growth of the tested fungi decreased with each increase in PEE concentrations. Propolis extract collected from Muğla province showed 77.81% antifungal effect against Fusarium oxysporum at the highest concentration (50 ppm). The lowest antifungal effect (64.52%) against the pathogen was detected in the propolis extract collected from Denizli province.

Stability of Styrax benzoin extract and fraction with the addition of glycerol and tween 80

This research to decide the consequences of expanding the steadiness of the concentrate and part of incense with the expansion of glycerol and tween 80 by contrasting the reference tests of frankincense separates available. The technique utilized in this examination depends on the expansion of glycerol and tween 80, just as directing boundaries of consistency, organoleptic, pH and investigation of substance content of concentrates and parts with GC-MS instruments. The outcomes got in this investigation demonstrate the actual properties of the concentrate and part of the incense sap as a thick fluid, earthy red and has an unmistakable fragrant smell. The consistency got from the thickness test was 277.68 Cp. In the meantime, the thickness estimation consequences of the reference test acquired a consistency worth of 326.54 cP. What's more, has a pH scope of 4.0-5.5. The fundamental synthetic parts of the extraction results and the isoprophyl part of styrax benzoin and the reference part of the reference styrax benzoin remove dependent on the consequences of the investigation discovered 6 mixtures that share practically speaking, in particular Benzoic corrosive, Vanillin, trans-Cinnamic corrosive, (Z) - Cinnamyl benzoate, 2-Propenoic corrosive , 3-phenyl-, phenylmethyl ester, (E) - and Cinnamyl cinnamate. Keywords: Styrax benzoin, Glycerol, Extract stability, Tween 80, Fractionation

Multi‐enzyme cascade reaction in a miniplant two‐phase‐system: Model validation and mathematical optimization

AbstractBiotechnological application of multiple enzymes in different phases for target compounds synthesis poses a significant challenge for industrial process development. At the same time, a growing demand for natural flavors and fragrances opens up possibilities for novel biotechnological processes to replace current chemical synthesis routes, with additional advantages such as avoiding harsh reaction conditions and toxic chemicals, and less by‐products in the system. Within complex biotechnological processes, the key for unfolding their industrial application potential in bioprocess engineering lies in their mathematical modeling. In this contribution, a multi‐enzyme cascade reaction in a two‐phase system implemented in a miniplant‐scale reactor setup is mathematically modeled for the example of the flavoring agent cinnamyl cinnamate. Using our validated model and a mathematical optimization tool based on a genetic algorithm, optimization runs are performed to demonstrate the potential of computer‐aided process development for complex biotechnological processes.

A Multi-Enzyme Cascade for the Production of High-Value Aromatic Compounds

Cascade reactions are the basis of life in nature and are adapted to research and industry in an increasing manner. The focus of this study is the production of the high-value aromatic ester cinnamyl cinnamate, which can be applied in flavors and fragrances. A three-enzyme cascade was established to realize the synthesis, starting from the corresponding aldehyde with in situ cofactor regeneration in a two-phase system. After characterization of the enzymes, a screening with different organic solvents was carried out, whereby xylene was found to be the most suitable solvent for the second phase. The reaction stability of the formate dehydrogenase (FDH) from Candida boidinii is the limiting step during cofactor regeneration. However, the applied enzyme cascade showed an overall yield of 54%. After successful application on lab scale, the limitation by the FDH was overcome by immobilization of the enzymes and an optimized downstream process, transferring the cascade into a miniplant. The upscaling resulted in an increased yield for the esterification, as well as overall yields of 37%.

Enzyme cascade reaction for the synthesis of cinnamyl cinnamate

Enzyme cascade reaction for the synthesis of cinnamyl cinnamate

Multi-Targeting Bioactive Compounds Extracted from Essential Oils as Kinase Inhibitors.

Essential oils (EOs) are popular in aromatherapy, a branch of alternative medicine that claims their curative effects. Moreover, several studies reported EOs as potential anti-cancer agents by inducing apoptosis in different cancer cell models. In this study, we have considered EOs as a potential resource of new kinase inhibitors with a polypharmacological profile. On the other hand, computational methods offer the possibility to predict the theoretical activity profile of ligands, discovering dangerous off-targets and/or synergistic effects due to the potential multi-target action. With this aim, we performed a Structure-Based Virtual Screening (SBVS) against X-ray models of several protein kinases selected from the Protein Data Bank (PDB) by using a chemoinformatics database of EOs. By evaluating theoretical binding affinity, 13 molecules were detected among EOs as new potential kinase inhibitors with a multi-target profile. The two compounds with higher percentages in the EOs were studied more in depth by means Induced Fit Docking (IFD) protocol, in order to better predict their binding modes taking into account also structural changes in the receptor. Finally, given its good binding affinity towards five different kinases, cinnamyl cinnamate was biologically tested on different cell lines with the aim to verify the antiproliferative activity. Thus, this work represents a starting point for the optimization of the most promising EOs structure as kinase inhibitors with multi-target features.

Pilot-scale Operation of a Multi-enzymatic Cascade Reaction in a Multiphase System

This work aims to emphasize the importance of scale-up in biotechnological research, in order to introduce more environmentally friendly bio-catalyzed processes to the industry. Here, a complex biotechnological reference reaction system is investigated, and, for the first time, a successful synthesis of cinnamyl cinnamate from cinnamyl aldehyde in a multiphase system is established. A multi-enzymatic cascade reaction sequence with integrated co factor regeneration and in situ intermediate separation is applied. This highly integrated reaction system is successfully implemented in a pilot-scale reactor plant. Experimental results show complex relationships between physically separated unit operations.

Quality evaluation of Styrax based on quantitative determination of 7 chemical components using HPLC wavelength switching method and chemometrics

In order to evaluate the quality of Styrax more comprehensively,this study attempted to establish an HPLC wavelength switching method to simultaneously determine the content of seven compounds in Styrax,and chemometrics were used to analyze the quality difference between different sources of Styrax,and finally establish a characteristic chromatogram of Styrax. The column was Agilent ZORBAX Extend C18( 4. 6 mm×250 mm,5 μm) with phase a mixture of acetonitrile-0. 1% phosphoric acid aqueous solution as the mobile phase in a gradient elution procedure; the detection wavelength was set as follows: 0-13. 5 min,194 nm( benzoic acid);13. 5-20. 5 min,278 nm( cinnamic acid); 20. 5-32 min,194 nm( benzyl benzoate,benzyl cinnamate,cinnamyl cinnamate,dehydroabietic acid); 32-55 min,241 nm( abietic acid). The methodological verification results showed that when the injection masses of benzoic acid,cinnamic acid,benzyl benzoate,benzyl cinnamate,cinnamyl cinnamate,dehydroabietic acid and abietic acid were0. 006 948-0. 694 8,0. 001 426-0. 142 6,0. 013 16-0. 658 0,0. 006 148-0. 614 8,0. 008 035-0. 803 5,0. 002 121-0. 212 1,and0. 010 172-1. 017 2 μg,respectively,there were good linear relationship between injection mass and peak area. The average recovery rates of seven compounds were in the range from 94. 34% to 105. 8%,and all RSD were less than 3. 0%( n = 6). The methodological verification results showed that the developed HPLC wavelength switching method has good accuracy and repeatability. The results of the sample analysis showed that the quality of Styrax from different sources was quite different. The chromatogram of Styrax reference material( S1) was used as the reference chromatogram to calculate the fingerprint similarity of each batch of samples. The results showed that the similarities of samples S2-S10 were 0. 952,0. 949,0. 981,0. 351,0. 751,0. 969,0. 979,0. 992 and 0. 971,respectively.The similarity values of other batches samples were satisfactory,except for sample S5 and S6,indicating that the quality difference among these samples is small. The similarity values of S11-S20 were 0. 060,0. 055,0. 054,0. 285,0. 092,0. 002,0. 044,0. 044,0. 044,and 0. 040,respectively. The results showed that compared with the sample S1,there was a large quality difference among S11-S20. Based on the chromatograms of S1-S10,the HPLC characteristic chromatograms of Styrax was established and the purpose is to give reference to other pharmaceutical researchers. The newly developed HPLC wavelength switching method have the advantages of simplicity,reproducibility and specificity,and the developed HPLC characteristic chromatograms provided a reference method for the overall quality evaluation of Styrax.

The Antibiotic Activity of Tea Tree, Eucalyptus, and Cinnamon Bark Oils

The emergence of antibiotic resistant bacteria is of pressing concern, especially given that the pharmaceutical industry has decreased funding for infectious disease drug discovery programs. It is estimated that over 2 million people are infected with antibiotic resistant strains of bacteria each year, resulting in over 23,000 deaths. Researchers are currently looking for novel antibiotics in alternative sources. Essential oils, derived from plants, are an ancient homeopathic remedy that are traditionally known to have antimicrobial properties. Therefore, several essential oils were examined in search of novel antibiotics. Tea tree (Melaleuca alternifela), eucalyptus (Eucalyptus globulus), and cinnamon bark (Cinnamomum cassia Blume) oils showed antibiotic activity in Kirby‐Bauer disk diffusion assays. The Minimum Inhibitory Concentration (MIC) values for tea tree, eucalyptus, and cinnamon bark oils were determined to be 1.25%, 0.313%, and 0.0391%, respectively. All three oils proved effective against both Gram‐positive Staphylococcus aureus and Gram‐negative Escherichia coli. Cinnamon bark oil was the most effective and was further characterized. Cinnamon bark oil retained its MIC in the presence of 10% human serum protein, indicating that it does not interact with proteins in the bloodstream. Cinnamon bark oil showed bactericidal activity in a time kill assay. To determine the active component within cinnamon bark oil, an analysis of its constituents was conducted. Three of the main components of cinnamon bark oil, trans‐cinnamaldehyde, cinnamyl cinnamate, and benzyl cinnamate, were subjected to preliminary testing via Kirby‐Bauer disk diffusion tests. Trans‐cinnamaldehyde appeared to be the only effective component against both S. aureus and E. coli. Results suggest that cinnamon bark oil may contain a promising novel antibiotic.Support or Funding InformationThis research was supported by Grand Valley State University's Student Summer Scholars program.

Evaluation of anti-inflammatory activity and standardisation of hydro-methanol extract of underground tuber of Dioscorea alata

abstractContext The underground edible tuber of Dioscorea alata L. (Dioscoreaceae) is a functional food with high nutritive value and therapeutic potential. The tuber is known to possess anti-inflammatory properties in traditional medicine.Objective The present study explores the anti-inflammatory activity and standardisation of D. alata tuber hydromethanol extract.Materials and methods Hydromethanol extract (70%) of D. alata tuber was chemically characterised using HPLC and GC-MS techniques. Murine lymphocytes were cultured for 48 h with six different concentrations (0–80 μg/mL) of the extract. The expression of nitric oxide (NO), TNF-α, COX-1, COX-2, and PGE2 were evaluated using colorimetric and ELISA methods.Results Dioscorea alata extract inhibited the expression of NO and TNF-α with an IC50 value of 134.51 ± 6.75 and 113.30 ± 7.44 μg/mL, respectively. The IC50 values for inhibition of total COX, COX-1, COX-2 activities and PGE2 level were 41.96 ± 3.07, 141.41 ± 8.99, 32.50 ± 1.69, and 186.34 ± 15.36 μg/mL, respectively. Inhibition of PGE2 level and COX-2 activity was positively correlated (R2 = 0.9393). Gallic acid (GA), 4-hydroxy benzoic acid (4HBA), syringic acid (SYA), p-coumaric acid (PCA), and myricetin (MY) were identified and quantified using HPLC. GC-MS analysis revealed the presence of 13 different phytocompounds such as hexadecanoic acid, methyl stearate, cinnamyl cinnamate, and squalene.Conclusion The D. alata extract significantly down-regulated the pro-inflammatory signals in a gradual manner compared with control (0 μg/mL). Different bioactive phytocompounds individually possessing anti-inflammatory activities contributed to the overall bioactivity of the D. alata tuber extract.

Effects of volatile chemical components of wood species on mould growth susceptibility and termite attack resistance of wood plastic composites

This study mainly aimed at investigating the effects of volatile chemical components of wood species on mould and termite resistance of wood plastic composites (WPC) using artificial accelerated tests. The morphology characterization of surface and fracture of WPC was estimated by SEM and digital instrument. Volatile chemical components of wood species extractives were analyzed by GC–MS. The results indicated that the sequences of mould resistance of WPC were ranked as: Cunninghamia lanceolata and Melaleuca leucadendra (level 0) > Eucalyptus grandis × Eucalyptus urophylla (level 1) > Pinus massoniana (level 2) > Liquidambar formosana and Ricinus communis (level 4). The sequences of termite resistance of WPC were ranked as: C. lanceolata (level 1, ML = 4.52%) > M. leucadendra (level 1, ML = 5.73%) > E. grandis × E. urophylla (level 1, ML = 6.48%) > L. formosana (level 2, ML = 6.72%) > P. massoniana (level 2, ML = 7.08%) > R. communis (level 3, ML = 10.40%). It was also suggested that 8-propoxy-cedrane, cedrol, α-cedrene and β-cedrene in C. lanceolata, 2,3-dihydro-2,2-dimethyl-3,7-benzofurandiol, 3-demethyl-colchicine and squalene in M. leucadendra; 2,3-dihydro-2,2-dimethyl-3,7-benzofurandiol and stigmast-4-en-3-one in E. grandis × E. urophylla were potentially crucial to provided positive effects on biodegradation resistance. Longifolene, caryophyllene and α-pinene in P. massoniana; 4-hydroxy-3,5-dimethoxy-benzaldehyde, 3,5-dimethoxy-4-hydroxycinnamaldehyde and cinnamyl cinnamate in L. formosana; 5-hydroxymethylfurfural and 1,6-anhydro-β-d-glucopyranose in R. communis led to the opposite results.

VOLATILE OIL COMPOSITION AND ANTIMICROBIAL ACTIVITY OF CURCUMA OLIGANTHA VAR. LUTEA RHIZOMES

Hydrodistilled volatile oil obtained from the rhizomes of Curcuma oligantha Trimen var. lutea (Zingiberaceae) was analyzed by GC and GC - MS. The volatile oil was composed main ly of cinnamyl cinnamate (48.9%), n - hexanal (14.0%) and n - octadecane (10.1%). Among the ten monoterpenes (7.1%) present in the oil, the prominent one was β - pinene (2.8%) followed by α - pinene (1.6%) and terpinen - 4 - ol (1.6%). The oil contained sixteen sesquiterpen es (9.7%) comprising mainly ar - turmerone (3.0%), c a dinol (1.3%), eudesmol (1.2%) and bisabolol oxide (1.1%). The predominant constituents were the aromatic esters (54.4%) including cinnamyl cinnamate (48.9%) and benzyl benzoate (2.9%). The important alipha tic constituents were characterized as n - hexanal (14.0%), n - octadecane (10.1%) and isoamyl pyruvate (1.9%). About 25 components occurred in trace amounts in the oil. The volatile oil and ethanolic extract of the rhizomes showed significant antimicrobial ac tivity.

Constituents of Hondurian Propolis with Inhibitory Effects on Saccharomyces cerevisiae Multidrug Resistance Protein Pdr5p

Chemical investigation of a propolis sample collected in Honduras has led to the isolation of the new (E,Z)-cinnamyl cinnamate (2) together with 14 known compounds: 6 cinnamic ester derivatives, 2 flavanones, 1 chalcone, 2 triterpenes, and 3 aromatic acids. Structural determination was accomplished by spectroscopic analysis, particularly two-dimensional (2D) nuclear magnetic resonance (NMR) and electrospray ionization-tandem mass spectrometry (ESI-MS/MS) techniques. Futhermore, we checked the ability of the propolis extract and the most representative compounds of each class (1, 5, 8, and 10) to inhibit the activity of Pdr5p, a protein responsible for a multidrug resistance phenotype in yeast. The present study appears to be the first report on Honduras propolis. Isolated cinnamic ester derivatives indicated the possible relation between Honduras propolis and the genus Liquidambar .

Immediate-type food allergy to balsam of Peru

A 48-year old woman presented with a 10-year history of rapid-onset adverse reactions to foods. Reactions involved discomfort in the lips, throat and tongue, throat tightness, an urticarial rash, and a 'sensation of doom'. Suspect triggers included butter toffee popcorn, the aperitif Pernod, cinnamon, toffee apples, ginger nut biscuits, honeycomb confectionary and a supermarket pizza. Additionally, she described contact hypersensitivity to jewellery and cosmetics. Certain soaps and household detergents also provoked urticaria. Skin tests and ImmunoCAP tests to aeroallergens and food allergens were negative; prick-prick testing to the same popcorn was also negative. Nonetheless, we felt her history was convincing, and were suspicious of a linking factor between the identified triggers. We subsequently referred her for patch testing. Patch tests produced a rapid onset urticarial response to myroxylon sulphate (Balsam of Peru); the delayed response was negative. Delayed responses were positive to nickel sulphate and Fragrance mix 1 and 2. We conclude that our patient had an acute-onset hypersensitivity to Balsam of Peru, an aromatic liquid derived from the Myroxolon balsamum tree used in cosmetics, foods, beverages and medicinal products. It contains cinnamic acid, cinnamyl cinnamate, benzyl benzoate, benzoic acid and vanilla, as well as essential oils similar to those found in citrus fruit peel. It most commonly causes a contact dermatitis; highly allergic individuals may suffer adverse reactions after consuming foods containing Balsam of Peru including soreness of the tongue and mouth. Implicated foods include spices, citrus fruit peel, baked goods, aperitifs, benzoic acid and related preservatives. Our patient is unusual in presenting with acute symptoms, mimicking IgE-mediated allergy. Of note, contact urticarial reactions have previously been described to patch testing with Balsam of Peru; the mechanism of such reactions is unclear. Clinicians should be aware of non-classical food ‘allergic’ reactions, especially to pre-prepared foods with complex ingredients.

Identification of the Constituents of Balsam of Peru in Tomatoes

Studies show that balsam-restricted diets result in significant improvement of systemic contact dermatitis in patients with contact allergy to balsam of Peru (BOP). While tomatoes have been implicated as a frequent cause of BOP-related dermatitis, the presence of BOP in tomatoes has never been confirmed. High-performance liquid chromatography coupled with mass spectrometry (liquid chromatography [LC]-MS) and UV spectrometry (LC-UV) was used to detect the possible presence of BOP constituents in tomatoes. Samples of beefsteak, cherry, and plum tomatoes were extracted in ethyl acetate and analyzed with LC-MS and LC-UV for the presence of the following sensitizing constituents of BOP: benzoic acid, benzyl alcohol, trans-cinnamic acid, cinnamic alcohol, cinnamyl cinnamate, coniferyl alcohol, eugenol, isoeugenol, and methyl cinnamate. The initial LC-MS analysis of each tomato extract showed multiple peaks. Two of these peaks had molecular weights of 134 and 180, which correspond to cinnamic alcohol and coniferyl alcohol, respectively. The analysis did not show peaks corresponding to the molecular weights of the remaining compounds. Cochromatography of tomato extract with cinnamic alcohol and coniferyl alcohol using LC-UV further suggested the presence of these compounds in the tomato extract. Coniferyl alcohol and cinnamic alcohol, constituents of BOP, are present in beefsteak, cherry, and plum tomatoes.