4-Isopropylbenzaldehyde

Safety and efficacy of cumin tincture (Cuminum cyminum L.) when used as a sensory additive for all animal species.[Pubmed:32625910]

EFSA J. 2018 May 17;16(5):e05273.

Following a request from the European Commission, the EFSA Panel on Additives and Products or Substances used in Animal Feed (FEEDAP) was asked to deliver a scientific opinion on the safety and efficacy of cumin tincture (Cuminum cyminum L.) when used as a sensory feed additive for all animal species. The product is a water ethanol solution, which contains 0.002-0.003% of 4-Isopropylbenzaldehyde (cuminaldehyde). The FEEDAP Panel concludes that the additive cumin tincture is safe at the maximum proposed use level (30 muL/kg complete feed or water for drinking) for all animal species. No safety concern would arise for the consumer from the use of cumin tincture up to the highest safe level in feeds. No specific data were provided by the applicant regarding the safety of the additive for users. In the absence of data, no conclusions can be drawn on the additive's potential to be a dermal/eye irritant or a skin sensitiser. The use of cumin tincture at the maximum proposed dose is not considered to be a risk for the environment. Since the major components of the additive are recognised to provide flavour in food and its function in feed would be essentially the same, no demonstration of efficacy is considered necessary.

Anaerobic activation of p-cymene in denitrifying betaproteobacteria: methyl group hydroxylation versus addition to fumarate.[Pubmed:25261521]

Appl Environ Microbiol. 2014 Dec;80(24):7592-603.

The betaproteobacteria "Aromatoleum aromaticum" pCyN1 and "Thauera" sp. strain pCyN2 anaerobically degrade the plant-derived aromatic hydrocarbon p-cymene (4-isopropyltoluene) under nitrate-reducing conditions. Metabolite analysis of p-cymene-adapted "A. aromaticum" pCyN1 cells demonstrated the specific formation of 4-isopropylbenzyl alcohol and 4-Isopropylbenzaldehyde, whereas with "Thauera" sp. pCyN2, exclusively 4-isopropylbenzylsuccinate and tentatively identified (4-isopropylphenyl)itaconate were observed. 4-Isopropylbenzoate in contrast was detected with both strains. Proteogenomic investigation of p-cymene- versus succinate-adapted cells of the two strains revealed distinct protein profiles agreeing with the different metabolites formed from p-cymene. "A. aromaticum" pCyN1 specifically produced (i) a putative p-cymene dehydrogenase (CmdABC) expected to hydroxylate the benzylic methyl group of p-cymene, (ii) two dehydrogenases putatively oxidizing 4-isopropylbenzyl alcohol (Iod) and 4-Isopropylbenzaldehyde (Iad), and (iii) the putative 4-isopropylbenzoate-coenzyme A (CoA) ligase (Ibl). The p-cymene-specific protein profile of "Thauera" sp. pCyN2, on the other hand, encompassed proteins homologous to subunits of toluene-activating benzylsuccinate synthase (termed [4-isopropylbenzyl]succinate synthase IbsABCDEF; identified subunits, IbsAE) and protein homologs of the benzylsuccinate beta-oxidation (Bbs) pathway (termed BisABCDEFGH; all identified except for BisEF). This study reveals that two related denitrifying bacteria employ fundamentally different peripheral degradation routes for one and the same substrate, p-cymene, with the two pathways apparently converging at the level of 4-isopropylbenzoyl-CoA.

Two different primary oxidation mechanisms during biotransformation of thymol by gram-positive bacteria of the genera Nocardia and Mycobacterium.[Pubmed:22828982]

Appl Microbiol Biotechnol. 2013 Feb;97(3):1289-97.

Thymol has antibacterial, antifungal, insecticidal, and antioxidative properties which are the basis for the wide use of this compound in the cosmetic, food, and pharmaceutical industries. Although thymol is a ubiquitously occurring substance in the environment, data about its degradation and detoxification by bacteria are sparse. Here, we show the existence of two different pathways for the biotransformation of thymol by Nocardia cyriacigeorgica and Mycobacterium neoaurum which were described for the first time for gram-positive bacteria. The first pathway starts with hydroxylation of thymol to thymohydroquinone (2-isopropyl-5-methylbenzene-1,4-diol) with subsequent oxidation to thymobenzoquinone (2-isopropyl-5-methyl-1,4-benzoquinone). The second pathway involves hydroxylation of the methyl group followed by oxidation to 3-hydroxy-4-isopropylbenzoic acid, possibly via the aldehyde 3-hydroxy-4-Isopropylbenzaldehyde. It is noteworthy that the branched side chain of thymol was not oxidized. Similarities and differences of these oxidation processes with those of the gram-negative bacterium Pseudomonas putida, fungi, and plants are discussed and, in addition, the toxicity of thymol towards N. cyriacigeorgica and M. neoaurum was tested. The experiments showed a temporary growth inhibition with 0.025 % thymol. This was explained by degradation of thymol and the formation of products which are less toxic than thymol itself.

Toxicological evaluation of paper mill sewage sediment treated by indigenous dibenzofuran-degrading Pseudomonas sp.[Pubmed:22326333]

Bioresour Technol. 2012 Apr;110:71-8.

Organic pollutants present in the pulp and paper mill sewage were extracted with dichloromethane/acetone (1:1v/v), and the extract was added to minimal salt medium to study the degrading and detoxifying potential of Pseudomonas sp. strain ISTDF1. GC-MS analysis performed after biodegradation showed removal of chlorinated compounds like dichloroacetic acid, heptadecyl ester (RT=28.99) and formation of simpler compounds like 4-Isopropylbenzaldehyde (RT=7.52). Methyltetrazolium (MTT) assay for cytotoxicity, 7-ethoxyresorufin-O-deethylase (EROD) assay for dioxin-like behaviour and alkaline comet assay for genotoxicity were carried out in human hepato-carcinoma cell line HuH7 before and after bacterial treatment. The bacterium reduced toxicity as shown by a 5-fold increase in LC(50) value, 2110-fold reduction in benzo (alpha) pyrene equivalent value and an 8-fold reduction in Olive Tail Moment after 240h treatment. The EROD assay was found to be a useful method which indicated positive correlation with MTT and comet assay in post-biodegradation toxicity evaluation.

Synthesis, spectroscopic, antimicrobial, DNA binding and cleavage studies of some metal complexes involving symmetrical bidentate N, N donor Schiff base ligand.[Pubmed:21855399]

Spectrochim Acta A Mol Biomol Spectrosc. 2011 Nov;82(1):191-9.

The Schiff base ligand, N,N'-bis-(4-isopropylbenzaldimine)-1,2-diaminoethane (L), obtained by the condensation of 4-Isopropylbenzaldehyde and 1,2-diaminoethane, has been used to synthesize the complexes of the type [ML(2)X(2)] [M = Co(II), Ni(II) and Zn(II); X = Cl and OAc]. The newly synthesized ligand (L) and its complexes have been characterized on the basis of elemental analyses, mass, (1)H and (13)C-NMR, molar conductance, IR, UV-vis, magnetic moment, CV and thermal analyses, powder XRD and SEM. IR spectral data show that the ligand is coordinated to the metal ions in a bidentate manner. The geometrical structures of these complexes are found to be octahedral. Interestingly, reaction with Cu(II) ion with this ligand undergoes hydrolytic cleavage to form ethylenediamine copper(II) complex and the corresponding aldehyde. The antimicrobial results indicate that the chloro complexes exhibit more activity than the acetato complexes. The complexes bind to CT-DNA by intercalation modes. Novel chloroform soluble ZnL(2)Cl(2) complex exhibits tremendous antimicrobial, DNA binding and cleaving properties.

Effects of cuminaldehyde on melanoma cells.[Pubmed:18412105]

Phytother Res. 2008 Jun;22(6):809-13.

Cuminaldehyde (4-Isopropylbenzaldehyde) suppressed melanin formation in cultured murine B16-F10 melanoma cells in a dose-dependent decrease up to 0.25 mm without affecting cell growth. Approximately 30% suppression in melanin production resulted when the cells were cultured with 0.25 mm of cuminaldehyde. This activity was not noticeable with cultured human A375 melanoma cells.

2-hydroxy-4-isopropylbenzaldehyde, a potent partial tyrosinase inhibitor.[Pubmed:14741268]

Bioorg Med Chem Lett. 2004 Feb 9;14(3):681-3.

Chamaecin (2-hydroxy-4-Isopropylbenzaldehyde) was synthesized and tested for its tyrosinase inhibitory activity. It partially inhibits the oxidation of L-3,4-dihydroxyphenylalanine (L-DOPA) catalyzed by mushroom tyrosinase with an IC(50) of 2.3 microM. The inhibition kinetics analyzed by Dixon plots found that chamaecin is a mixed type inhibitor. This inhibition may come in part from its ability to form a Schiff base with a primary amino group in the enzyme.