Eugenol - CAS 97-53-0
Catalog number: 97-53-0
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Eugenol is used in antiseptic and anaesthetic.Eugenol has sedative, antioxidant, anti-inflammatory, and analgesic effects.Eugenol kills certain human colon cancer cell lines in vitro and in vivo.
SYNTHETIC CLOVE OIL; PHENOL, 4-ALLYL-2-METHOXY; 1,3,4-Eugenol; 1-Allyl-4-hydroxy-3-methoxybenzene; 1-Hydroxy-2-methoxy-4-allylbenzene; 1-Hydroxy-2-methoxy-4-prop-2-enylbenzene; 2-Hydroxy-5-allylanisole; 2-Methoxy-1-hydroxy-4-allylbenzene
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1. Biotransformation of Eugenol to Bis-eugenol by Kalopanax pictus Cell Culture
Bong-Gyu Kim, Jae Young Kim, Yongsub Yi, Yoongho Lim. J Korean Soc Appl Biol Chem (2012) 55, 677−680
Eugenol (4-allyl-2-methoxyphenol) is a member of the phenylpropanoid class compounds, and commonly used as a flavoring agent in cosmetic and food products and as a dental material such as temporary filling and root canal sealer by zinc oxide eugenol cements. In addition, several studies demonstrated that eugenol show the positive properties of antioxidant and anti-inflammatory activities, as well as antigenotoxic and anticarcinogenic potentials (Fotos et al., 1986; Feng and Lipton, 1987; Hashimoto et al., 1988; Zheng et al., 1992; Rompelberg et al., 1996; Nagababu and Lakshmaiah, 1997). However, eugenol has adverse effects of causing inflammatory and allergic reactions such as allergic contact dermatitis at higher concentrations, due to the formation of phenoxyl radicals, quinone methide intermediates via its pro-oxidant activity (Atsumi et al., 2000). To reduce the adverse effects, some researches proposed that eugenol was synthesized into various dimers of eugenol-related compounds, and the dimers showed lower cytotoxicity and had a significantly higher antioxidant activity than eugenol (Satoh et al., 1998; Atsumi et al., 2000). Up to now, chemical synthesis has been used to produce bis-eugenol; however, it has limiting factors such as regioselectivity of the synthesis products and usage of harmful reagents. If it is possible to produce the rational amount of biseugenol by biotransformation with cell derived from plants, this method could be a solution that can replace chemical synthesis. Therefore, we attempted to produce bis-eugenol by biotransformation using Kalopanax. pictus callus (KACs) and successfully achieved the production of bis-eugenol from eugenol (Fig. 1).
2. Eugenol as a renewable feedstock for the production of polyfunctional alkenes via olefin cross-metathesis
Hallouma Bilel, Naceur Hamdi, Fethi Zagrouba, Cedric Fischmeister* and Christian Bruneau*. RSC Adv., 2012, 2, 9584–9589
Compound 23, obtained by O-acylation of eugenol, was also submitted to cross-metathesis under the best conditions identified during the experiments with eugenol for each olefin partner (Scheme 5). The best results are gathered in Table 4. As depicted for the cross-metathesis of 17, all reactions proceeded with high to full conversion and the cross-metathesis products were isolated in moderate to good yields. Again, the slow addition of catalyst was necessary to ensure high conversion with acrylonitrile and acrylamide derivatives. Products 24, 25, 27 and 28 were obtained as (E)-isomers whereas 26 was obtained as a mixture of (Z)/(E) isomers in a 3 : 1 ratio.
3. Electrochemical behavior of eugenol on TiO2 nanotubes improved with Cu2O clusters
Shi-Zhao Kang, Hong Liu, Xiangqing Li, Mojie Sun and Jin Mu*. RSC Adv.,2014, 4, 538–543
Now, electrochemical technique has attracted increasing attention in the field of trace detection due to its fast response, low cost, simple operation, on-line detection and ease of miniaturization. A series of electrochemical sensors have been fabricated to monitor trace organics, such as bisphenol A, uric acid, penicillamine, magnolol and honokiol. These results reported previously show that electrochemical sensors are highly qualified for meeting the requirements of sensitivity, size, fast response and cost for the routine monitoring of eugenol in personal care products, foods and environmental samples. Therefore, it is significant to explore the electro-chemical detection of trace eugenol. TiO2 nanotubes (TiNTs) with 1D tubular structure have been widely used in the fields of solar cell, direct methanol fuel cell, photocatalysis, lithium battery, supercapacitor, sensor, and so on, because of their high surface-to-volume ratio, high degree of electron mobility along the tube and strong adsorption capability. A lot of electrochemical sensors based on TiNTs have been successfully fabricated for the detection of various molecules and biomolecules, such as H2O2, microcystin-LR, formaldehyde, CO etc. Therefore, it can be expected that the TiNTs-based electrochemical sensors would exhibit excellent performance for the detection of trace eugenol. However, to our best knowledge, there are limited reports on the electro-chemical sensor based on the TiNTs for the detection of trace eugenol so far. The electrochemical behavior of eugenol on the electrodes modified with TiNTs is also not clear. Hence, a systematic investigation on the electrochemical behavior of eugenol on the TiNTs modified electrodes is essential.
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CAS 97-53-0 Eugenol

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