Hydrolytic metabolism of phenyl and benzyl salicylates, fragrances and flavoring agents in foods, by microsomes of rat and human tissues

Ozaki, Hitomi; Sugihara, Kazumi; Tamura, Yukie; Fujino, Chieri; Watanabe, Yoko; Uramaru, Naoto; Sone, Tomomichi; Ohta, Shigeru; Kawa, Shigeyuki

doi:10.1016/j.fct.2015.08.024

Cited by 7 publications

(3 citation statements)

References 35 publications

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“…Carboxylesterases (CEs) are present in microsomal fractions of various tissues, including liver, intestine and skin [57]. CEs play crucial roles in the metabolism of various ester xenobiotics including drugs [56] and cosmetic ingredients such as parabens [58,59], or salicylates [60]. On the contrary to CYP450 enzymes no catalytic cofactors are involved in the CEs-catalyzed reactions [59].…”

Section: Resultsmentioning

confidence: 99%

Discovery of Novel UV-Filters with Favorable Safety Profiles in the 5-Arylideneimidazolidine-2,4-dione Derivatives Group

et al. 2019

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Effective protection from the harmful effects of UV radiation may be achieved by using sunscreens containing organic or inorganic UV filters. The number of currently available UV filters is limited and some of the allowed molecules possess limitations such as systemic absorption, endocrine disruption properties, contact and photocontact allergy induction, and low photostability. In the search for new organic UV filters we designed and synthesized a series consisting of 5-benzylidene and 5-(3-phenylprop-2-en-1-ylidene)imidazolidine-2,4-dione (hydantoin) derivatives. The photoprotective activity of the tested compounds was confirmed in methanol solutions and macrogol formulations. The most promising compounds possessed similar UV protection parameter values as selected commercially available UV filters. The compound diethyl 2,2′-((Z)-4-((E)-3-(4-methoxyphenyl)allylidene)-2,5-dioxoimidazolidine-1,3-diyl)diacetate (4g) was characterized as an especially efficient UVA photoprotective agent with a UVA PF of 6.83 ± 0.05 and favorable photostability. Diethyl 2,2′-((Z)-4-(4-methoxybenzylidene)-2,5-dioxo- imidazolidine-1,3-diyl)diacetate (3b) was the most promising UVB-filter, with a SPFin vitro of 3.07 ± 0.04 and very good solubility and photostability. The main photodegradation products were geometric isomers of the parent compounds. These compounds were also shown to be non-cytotoxic at concentrations up to 50 µM when tested on three types of human skin cells and possess no estrogenic activity, according to the results of a MCF-7 breast cancer model.

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Section: Resultsmentioning

confidence: 99%

Discovery of Novel UV-Filters with Favorable Safety Profiles in the 5-Arylideneimidazolidine-2,4-dione Derivatives Group

et al. 2019

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“…This also indicates that the very weak but statistically significant effect observed in the rat study by Zhang et al [ 7 ] at 3.7–100 mg/kg bw/d is unlikely to be caused by the estrogenic mode-of action of BS due to the low potency of BS. Furthermore, BS is an ester which is rapidly hydrolyzed by carboxyl esterases in microsomes isolated from different tissues, with highest activities in microsomes isolated from the intestine and the liver [ 21 ]. Thus actual exposure to the parent molecule in an in vivo situation will be significantly reduced by first-pass metabolism in the intestine and the liver as compared to the in vitro situation, which will further decrease potency of BS in vivo .…”

Section: Discussionmentioning

confidence: 99%

A critical assessment of the estrogenic potency of benzyl salicylate

et al. 2021

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Highlights Benzyl salicylate (BS) is on priority lists for evaluation of estrogenic effects. New data in both MCF7 (E-screen) and luciferase transactivation assays. Potency of BS is 21′000′000-fold lower than estradiol in transactivation assay. Potency of BS is 36′000′000-fold lower than estradiol in E-screen. Potency is > 1000-fold below human relevant potency threshold.

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“…It is also used as an anaesthetic in aquaculture. The non-toxic effect of this ester has extended its utility as a flavoring agent in food and commercial products (Ozaki et al, 2015). The vast significance of such esters has enhanced the interest in exploring their structure-activity relationships and to search for esters as biological lead compounds.…”

Section: Structure Descriptionmentioning

confidence: 99%

Methyl 2-(benzoyloxy)benzoate

Naveen

Zabiulla

et al. 2016

IUCr Data

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In the title compound, C 15 H 12 O 4 , the arene rings are inclined at an angle of 65.97 (6) . The pendant methyl ester substituent has an extended conformation. In the crystal, molecules are linked by C-HÁ Á Á interactions, forming chains propagating along the b-axis direction. The chains are linked via offsetinteractions [intercentroid distance = 3.640 (1) Å ], forming sheets parallel to (101). Structure descriptionEsters are a class of organic compounds which are of synthetic interest. Esters of salicylic acid such as acetyl salicylic acid (phenolic ester), phenyl salicylate and methyl salicylate (carboxylic esters) are widely used as drugs (Khanum et al., 2005). Methyl salicylate is a volatile organic compound which is used for the post-harvest treatment of fruits to protect them from chilling injury by protecting the cell wall of the lipid from oxidative affects. It is also used as an anaesthetic in aquaculture. The non-toxic effect of this ester has extended its utility as a flavoring agent in food and commercial products (Ozaki et al., 2015). The vast significance of such esters has enhanced the interest in exploring their structure-activity relationships and to search for esters as biological lead compounds. With these observations in mind, and as a part of our ongoing research on such molecules (Mohammed et al., 2016), we report here the synthesis and crystal structure of the title ester derivative.The molecular structure of the title compound is shown in Fig. 1. The molecule is nonplanar, the arene rings (C1-C6 and C8-C13) being inclined at a dihedral angle of 65.97 (6) . The pendant methyl ester chain has an extended conformation, as indicated by

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Hydrolytic metabolism of phenyl and benzyl salicylates, fragrances and flavoring agents in foods, by microsomes of rat and human tissues

Cited by 7 publications

References 35 publications

Discovery of Novel UV-Filters with Favorable Safety Profiles in the 5-Arylideneimidazolidine-2,4-dione Derivatives Group

Discovery of Novel UV-Filters with Favorable Safety Profiles in the 5-Arylideneimidazolidine-2,4-dione Derivatives Group

A critical assessment of the estrogenic potency of benzyl salicylate

Methyl 2-(benzoyloxy)benzoate

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