Contact Urticaria Caused by Preservatives and Disinfectants
Ana M. Giménez-Arnau, Howard I. Maibach in Contact Urticaria Syndrome, 2014
Benzoic acid is a metabolite of benzyl alcohol and sodium benzoate is the sodium salt of benzoic acid. These three related compounds are used as preservatives in a variety of products, such as cosmetics, toothpastes, hair products, medication preparations, and emollients, and in foods. They are well-recognized to cause nonimmu- nological CoU and reactions are concentration-dependent.[10] Both oral intake and cutaneous contact of benzyl alcohol, benzoic acid, or sodium benzoate can cause immediate reactions; however, there is a lack of correlation between the two and skin tests should not be used to predict sensitivity to oral intake of these preservatives.[10] Immediate reactions to the oral ingestion of these preservatives are rare. Nettis et al. investigated 47 patients with a history of urticaria after the ingestion of meals or products containing sodium benzoate, and only one patient had a generalized urticarial reaction to an oral challenge test of 50 mg of sodium benzoate.[11]
Toxicokinetics
Frank A. Barile in Barile’s Clinical Toxicology, 2019
The associated and dissociated structures of a base and an acid are illustrated in Figure 10.3 with aniline and benzoic acid, which possess strong basic and acidic characteristics, respectively. The structure of benzoic acid shows the carboxyl anion after dissociation. Since its pKa = 4, the Ka = 1 × 10−4, resulting in a higher dissociation constant and strong acidic properties. Similarly, aniline is a highly protonated species, with a pKb of 10 and corresponding Kb of 1 × 10−10 (pKa + pKb = 14; thus, although it is a base, the pKa of aniline can also be expressed as 4). The low dissociation constant of the base indicates that the H+ ions are closely held to the nitrogen and contribute to its strongly basic nature. Structures of aniline and benzoic acid.
Monographs of fragrance chemicals and extracts that have caused contact allergy / allergic contact dermatitis
Anton C. de Groot in Monographs in Contact Allergy, 2021
The clue to the cause of the acidosis came from examination of the urinary organic acid profile by gas-liquid chromatography. All samples contained huge quantities of benzoic and hippuric acid. Serum benzoic acid values have been measured in five of the infants; values range from 8.4 to 28.7 mmol/l (normal zero). The authors postulated that the benzyl alcohol is metabolized to benzoic acid which is then converted by the liver to hippuric acid. The quantity of the benzoic acid exceeded the capacity of the immature liver for detoxification so that the benzoic acid accumulated in serum, causing the metabolic acidosis (69). When preparations containing benzyl alcohol were removed from nurseries for premature infants, reports of the gasping syndrome and related deaths stopped (83).
Lingonberries and their two separated fractions differently alter the gut microbiota, improve metabolic functions, reduce gut inflammatory properties, and improve brain function in ApoE−/− mice fed high-fat diet
Published in Nutritional Neuroscience, 2020
Nittaya Marungruang, Tatiana Kovalenko, Iryna Osadchenko, Ulrikke Voss, Fang Huang, Stephen Burleigh, Galyna Ushakova, Galyna Skibo, Margareta Nyman, Olena Prykhodko, Frida Fåk Hållenius
Approximately 70% of total dietary fibre in wLB are insoluble, and 30% are soluble14. Hence, it is plausible that the effects of wLB are more similar to those seen with insLB than with solLB. LB contain high concentration of benzoic acid (0.6–1.3 g/l), giving their low pH (pH 2.6–2.9)38. Benzoic acid is highly soluble in water39, and most likely present in the solLB fraction. Ingestion of benzoic acid at higher doses than 500 mg/kg (body weight) in rodents, and 5 mg/kg in humans have been reported to cause acute toxicity, gastrointestinal disturbances, and weight loss40. The solLB diet included 15 g/kg dietary fibre from the solLB fraction, which corresponds to approximately 136 g/kg solLB fraction in the diet (Table 1). This means that approximately 200 mg/kg benzoic acid was received by each mouse, which was below the tolerance limit. A period of 2-week feeding of solLB in a HF diet prevented weight gain, reduced epidydimal fat pad weight, and improved glucose metabolism, without showing signs of diarrhoea or illness. In humans, it is difficult to obtain the toxic dose of benzoic acid from lingonberries, since approximately 3 kg of lingonberries may have to be consumed in a person with 60 kg body weight to reach the same toxic level of benzoic acid. A low dose of the solLB fraction may be used as a potential weight loss diet, but this needs further evaluation.
Synthesis and anti-rheumatoid arthritis activities of 3-(4-aminophenyl)-coumarin derivatives
Published in Journal of Enzyme Inhibition and Medicinal Chemistry, 2021
Yuhang Miao, Jie Yang, Yinling Yun, Jie Sun, Xiaojing Wang
The 3-(4-aminophenyl)-coumarin derivatives were synthesised using the synthesis method previously reported by our group, and the synthesis route is shown in Scheme 2. The intermediate 2 was synthesised from substituted p-amino-phenylacetic acid and o-hydroxybenzaldehyde by Perkin reaction and acidified with hydrochloric acid to give 3-(4-aminophenyl)-coumarin intermediate 3. In the next step, a series of substituted benzoyl chlorides were synthesised from benzoic acid. The target compound was obtained by amide condensation of 3 with substituted benzoyl chloride in the mixed solution of pyridine and acetone (Table 1, 4a–4q). The synthetic route of 3-(4-aminophenyl)-coumarin derivatives with heterocycles is shown in Scheme 3. Hydroxy benzotriazole (HOBt) and dicyclohexylcarbodiimide (DCC) were added to the anhydrous toluene solution containing compound A-E. Then the intermediate 3 was put into the reaction solution, and the reaction mixture was stirred at room temperature for 8–16 h to obtain 5a–5h34.
Synthesis and biological activity evaluation of 3-(hetero) arylideneindolin-2-ones as potential c-Src inhibitors
Published in Journal of Enzyme Inhibition and Medicinal Chemistry, 2022
Salvatore Princiotto, Loana Musso, Fabrizio Manetti, Valentina Marcellini, Giovanni Maga, Emmanuele Crespan, Cecilia Perini, Nadia Zaffaroni, Giovanni Luca Beretta, Sabrina Dallavalle
4-((6-chloro-2-oxoindolin-3-ylidene)methyl)benzoic acid (36) was prepared from 31 and 4-formylbenzoic acid. Purification by column chromatography (hexane/EtOAc 90:10 → 75:25, CH2Cl2/CH3OH 95:5 → 80:20, EtOAc/CH3OH 80:20) gave the title compound in 22% yield, as a yellow solid (m.p. 271–272 °C, dec.). 1H NMR (600 MHz, DMSO-d6), major isomer (E), δ: 10.86 (1H, bs); 8.10–8.03 (2H, m); 7.81–7.73 (2H, m); 7.71 (1H, s); 7.48 (1H, d, J = 7.48 Hz); 6.96–6.89 (2H, m). 13 C NMR (150 MHz, DMSO-d6), major isomer (E), δ: 168.4, 168.0, 144.5, 137.5, 135.6, 134.4, 131.6, 129.7 (× 2 C), 129.1 (× 2 C), 127.5, 123.8, 121.0, 119.6, 110.2.
Related Knowledge Centers
- Aromaticity
- Benzene
- Benzoin
- Carboxylic Acid
- Chemical Structure
- Organic Compound
- Secondary Metabolite
- Substituent
- Benzoyl Group
- Salt