Anethole Research Articles

Chemical composition and antifungal effect of anise (Pimpinella anisum L.) fruit oil at ripening stage

The composition of the essential oil ofPimpinella anisum L fruit is determined by GC and GC-MS. The volatile oil content obtained by hydrodistillation was 1.91%. Ten compounds representing 98.3% of the oil was identified. The main constituents of he oil obtained from dried fruits were trans-a nethole (93.9%) and estragole (2.4%). The olfactorially valuable constituents that were found with concentration higher than 0.06% were (E)-methyeugenol, α-cuparene, α-himachalene, β-bisabolene, p-anisaldehyde and cis-anethole. Also, the different concentrations of anise oil exerted varying levels of inhibitory effects on the mycelial growth off/ternaria alternata, Aspergillus niger andAspergillus parasiticus used in experimental. The results showed that the most effected fungus from anise oil wasA. parasiticus, which is followed byA. niger andA. alternata. Individual of this plant oil may provide a useful to achive adequate shelf-life of foods.

Screening for the effects of natural plant extracts at different pH on in vitro rumen microbial fermentation of a high-concentrate diet for beef cattle1

Six natural plant extracts and three secondary plant metabolites were tested at five doses (0, 0.3, 3, 30, and 300 mg/L) and two different pH (7.0 and 5.5) in a duplicate 9 x 5 x 2 factorial arrangement of treatments to determine their effects on in vitro microbial fermentation using ruminal fluid from heifers fed a high-concentrate finishing diet. Treatments were extracts of garlic (GAR), cinnamon (CIN), yucca (YUC), anise (ANI), oregano (ORE), and capsicum (CAP) and pure cinnamaldehyde (CDH), anethole (ATL), and eugenol (EUG). Each treatment was tested in triplicate and in two periods. Fifty milliliters of a 1:1 ruminal fluid-to-buffer solution were introduced into polypropylene tubes supplied with 0.5 g of DM of a 10:90 forage:concentrate diet (15.4% CP, 16.0% NDF; DM basis) and incubated for 24 h at 39 degrees C. Samples were collected for ammonia N and VFA concentrations. The decrease in pH from 7.0 to 5.5 resulted in lower (P < 0.05) total VFA, ammonia N, branched-chain VFA concentration, acetate proportion, and acetate:propionate, and in a higher (P < 0.05) propionate proportion. The interaction between pH and doses was significant for all measurements, except for ATL and CDH for butyrate, ATL and EUG for acetate:propionate ratio, and ORE for ammonia N concentration. The high dose of all plant extracts decreased (P < 0.05) total VFA concentrations. When pH was 7.0, ATL, GAR, CAP, and CDH decreased (P < 0.05) total VFA concentration, and ANI, ORE, CIN, CAP, and CDH increased (P < 0.05) the acetate:propionate. The CIN, GAR, CAP, CDH, ORE, and YUC decreased (P < 0.05), and EUG, ANI, and ATL increased (P < 0.05) ammonia N concentration. The effects of plant extracts on the fermentation profile when pH was 7.0 were not favorable for beef production. In contrast, when pH was 5.5, total VFA concentration did not change (ATL, ANI, ORE, and CIN) or increased (P < 0.05) (EUG, GAR, CAP, CDH, and YUC), and the acetate:propionate (ORE, GAR, CAP, CDH, and YUC) decreased (P < 0.05), which would be favorable for beef production. Ammonia N (ATL, ANI, CIN, GAR, CAP, and CDH) and branched-chain VFA (ATL, EUG, ANI, ORE, CAP, and CDH) concentrations also were decreased (P < 0.05), suggesting that deamination was inhibited. Results indicate that the effects of plant extracts on ruminal fermentation in beef cattle diets may differ depending on ruminal pH. When pH was 5.5, GAR, CAP, YUC, and CDH altered ruminal microbial fermentation in favor of propionate, which is more energetically efficient.

Influence of the Mobile and Stationary Phases on the Separation of Selected Essential Oil Components and Aroma Substances Investigated by TLC

Fifteen selected essential oil components and aroma substances were investigated using adsorption thin‐layer chromatography on silica gel 60 (E. Merck, #1.05744) and aluminum oxide (E. Merck, #1.05550) plates and the mobile phases benzene–chloroform, benzene–acetone, carbon tetrachloride–acetone, chloroform–acetone, and chlorobenzene–acetone in different volume compositions. The separations were evaluated on the basis of retention parameter RF and separation parameters values ΔRF, α, and RF α. None of the applied chromatographic conditions allowed for the complete separation of all the compounds examined. Aluminium oxide plates and carbon tetrachloride–acetone in volume composition 98:2 were optimal for the separation of the investigated alcohols: (+) borneol (B), geraniol (GR), menthol (M), and linalool (L). Aluminium oxide and carbon tetrachloride–acetone mobile phases in a volume composition of 85:15 were optimal for the separation of the investigated phenols: vanillin (V), guaiacol (G), eugenol (E), and thymol (T). Aluminium oxide and a chlorobenzene–acetone mobile phase in a volume composition of 95:5 was optimal for the separation of coumarin (C), cineole (CL), (R)‐(−) carvone (CR), cinnamic aldehyde (CA), camphor (CP), (1R)‐(−) fenchone (F), and trans anethole (A).

Content and Composition of Essential and Fatty Oil of Foeniculum Vulgare cv. Soroksari Cultivated Fruits

The essential oil from cultivated fruits of fennel (Foeniculum vulgare cv. soroksari) was extracted by hydrodistillation. The essential oil yield was 5.2% w/w based on dry weigth. The fatty oil content, after essential oil extraction and using Soxhlet-separation, was 8.2%. The essential oil was investigated by GC and GC/MS, while the fatty oil composition only by GC. Ninteen components were identified by GC/MS analyses. The main components of the essential oil were trans anethole (67.0%), fenchone (17.6%), methyl chavicol (3.7%), α-pinene (2.9%), limonene (2.6%) and γ-terpinene (1.5%). Seven fatty acids were determined from the fatty oil of fruits of fennel after essential oil extraction with major compounds oleic (59.0%), linoleic (19.0%), palmitic (10.3%), myristic (6.3%) and stearic acid (1.7%).

Free radical terpolymerization of three non-homopolymerizable monomers, 2. Terpolymerization ofN-ethylmaleimide, anethol andtrans-stilbene

The free radical terpolymerization of N-ethylmaleimide (NEMI), anethol (ANE) and trans-stilbene (Stb) in CCl4 at 60°C is described. For the first time, a new kinetic treatment has been applied to this ternary system in order to evaluate the degree of participation of free monomers and charge-transfer complexes in the polymerization process. It can be shown that at low monomer concentrations, free monomers dominate the polymerization process, at medium monomer concentrations, both species participate to the same extent and at high monomer concentrations, the participation of charge-transfer complexes increases strongly. The ternary system was also investigated according to the known terminal and complex model. The reactivity ratio according to the terminal model is k12 /k13 = 1,33, the reactivitity ratios according to the complex model are rI = 1,0 and rII = 0,7. The equilibrium constants for the formation of CT complexes between NEMI/ANE (CI) and NEMI/Stb (CII) at 25°C in CCl4 were determined to be KI = 0,34 L·mol–1 and KII = 0,21 L·mol–1, respectively.

Alternating terpolymerization of three non‐homopolymerizable monomers

AbstractThe free‐radical terpolymerization of maleic anhydride (MSA), isobutyl vinyl ether (VIBE) and anethol (ANE) at 60°C is described. These three monomers do not homopolymerize under the conditions used. Binary copolymers are only obtained from MSA and one of the two investigated donor monomers, whereas the binary copolymerization of VIBE with ANE is not possible. In all terpolymers from these three non‐homopolymerizable monomers the MSA content amounts to about 50 mol‐%; VIBE is about twice as reactive as ANE. The terpolymerization can formally also be described under the assumption that two binary complexes (MSA/ANE (I) and MSA/VIBE (II)) are copolymerized. For this case the reactivity ratios rI = 0,9 and rII = 1,7 are obtained.

Synthesis of a Nor-Neolignan from Krameria Ramosissima

The synthesis of the nomeolignan 2 , isolated from Krameria ramosissima, is described. It proceeds in seven steps from trans-anethol in an overall yield of 14%. The key step involves arylation of the benzofuranone 5 by 2,4,6-trimethoxyphenylle triacetate 8 .

Magnetic field effect on the exciplex luminescence as a probe for estimating the hyperfine interaction in a radical ion pair system

Magnetic field effect on 9-cyanophenanthrene —trans anethole exciplex gives theB 1/2 value, a measure of ‘average’ hyperfine interaction present in the system. This has been compared with the theoretically computed values of hyperfine coupling constants present in the component radical ions using the INDO-UHF method.

Copolymerization of maleic anhydride with ethyl cinnamate and with anethole in chloroform

The composition of the copolymers of maleic anhydride (MA) with ethyl cinnamate (EC) and with anethole (ANE) polymerized in chloroform solutions with a radical initiator is reported. A strong alternating tendency is observed in the ANE-MA copolymer but EC is incorporated dominantly into the EC-MA copolymer. Both ANE and EC form 1 : 1 charge-transfer complexes with MA with the equilibrium constants determined to be 0,0845 and 0,026 L/mol, respectively. Applicability of the terminal, the penultimate and the complex participation models of the copolymerization mechanism is examined by non-linear least-square minimization technique using the most general forms of the composition equations. The complex participation model is found to be slightly in favor for both EC-MA and ANE-MA copolymerizations in CHCl3.

Biosynthesis of anethole in [formula omitted][formula omitted] L.

Biosynthesis of anethole in [formula omitted][formula omitted] L.

Preparations du Trans‐P‐Methoxyphenyl‐1‐propene‐1‐14C‐3 (Trans Anethole 14C‐3) et du trans‐anethole (Noyau 14C‐U)

AbstractMethyl iodide 14C is reacted with lithium p‐methoxy phenylacetylenide to give with a 85% yield 1‐p‐methoxy‐phenyl‐1‐propyne‐3‐14C.Reduction of the latter with LiAlH4 leads to a mixture of trans anethole‐3‐14C (85%) and cis anethole (15%) with a 55% yield. After preparative gas chromatography pure trans anethole‐3‐14C is isolated with an overall yield of 20% based on methyl iodide 14C.Benzene 14C (U) is brominated into bromobenzene 14C (U) which by copper catalysed alcaline hydrolysis gives phenol 14C (U). Methylation of the latter leads to anisole 14C (U).Gattermann reaction with the latter gives a mixture of o‐and p‐méthoxy‐benzaldehyde 14C (U) in a 80% yield from which pure para isomere is isolated by colwmn chromatography with a 42% yield based on anisole 14C (U). Treated with ethyl magensium iodide p‐methoxybenzaldehyde leads to 1‐p‐methoxy‐phenyl‐1‐propanol (ring 14C‐U) the dehydration of which by heating with Al2O3 gives a mixture of trans anethole (ring 14C‐U) (80%) and cis anethole (ring 14C‐U) (20%). After preparative gas chromatography pure trans anethole (ring 14C‐U) is isolated with an overall yield of 5% based on barium carbonate 14C.

Potassium-Catalyzed Reactions of β-Alkylstyrenes and Anethol with Alkylbenzenes1

Potassium-Catalyzed Reactions of β-Alkylstyrenes and Anethol with Alkylbenzenes¹