2,4-Di-tert-butylphenol

2,4-di-tert-butylphenol.svg 2,4-Di-tert-butylphenol 2,4-Bis(1,1-dimethylethyl)phenol 2,4-Bis(tert-butyl)phenol 2,4-Di-tert-butylhydroxybenzene 96-76-4 89188 29873 7037 202-532-0 7311 FOB94G6HZT InChI=1S/C14H22O/c1-13(2,3)10-7-8-12(15)11(9-10)14(4,5)6/h7-9,15H,1-6H3 ICKWICRCANNIBI-UHFFFAOYSA-N CC(C)(C)c1ccc(O)c(c1)C(C)(C)C 14 22 1 White crystalline solid phenolic, medical 0.887 56.8 264.2 33 mg/L at 25 °C, pH 6 - 7 11.6 5 Pa @ 38°C Registration Dossier - ECHA https://echa.europa.eu/registration-dossier/-/registered-dossier/14828 echa.europa.eu 31 August 2024 05 09 Warning 315 318 410 264 273 280 302+352 305+351+338 310 332+313 362 391 501 2,4-Di-tert-butylphenol (2,4-DTBP) is a white solid with a phenolic odour. It is primarily used as a raw material for the production of several commercially important antioxidants and phenolic benzotriazole-type UV absorbers. It also finds use as a starting material in the synthesis of agrochemicals, fragrances and catalysts (i.e. Jacobsen's catalyst). Despite its toxicity against most tested organisms, it is made by a wide range of living organisms: 169 species of bacteria, fungi, plants, and animals.Zhao F Wang P Lucardi RD Su Z Li S Natural Sources and Bioactivities of 2,4-Di-Tert-Butylphenol and Its Analogs. Toxins 6 January 2020 12 1 35 10.3390/toxins12010035 free 31935944 7020479 Synthesis The butylation of phenol is typically achieved by a Friedel–Crafts alkylation with isobutylene catalysed by a strong acid. These acids can be either liquids like triflic acid, or solid acids such as zeolites. The isobutylene can be generated in situ by the dehydration of tert-butyl alcohol or methyl tert-butyl ether, which being liquids are simpler to handle than the highly flammable isobutylene gas.Yadav Ganapati D Doshi Nirav S Alkylation of phenol with methyl-tert-butyl ether and tert-butanol over solid acids: efficacies of clay-based catalysts Applied Catalysis A: General September 2002 236 1–2 129–147 10.1016/S0926-860X(02)00300-9 2002AppCA.236..129Y Applications 2,4-DTBP is used in the production of antioxidants like tris(2,4-di-tert-butylphenyl)phosphite and bis(2,4-di-tert-butylphenyl) pentaerythritol diphosphite. Phytopathogen defense 2,4-DTBP produced by phyllosphere-associated Aspergillus cvjetkovicii has been found to enhance the resistance of host rice cultivars to the fungal pathogen Rhizoctonia solani.Fan Xiaoyan Matsumoto Haruna Xu Haorong Fang Hongda Pan Qianqian Lv Tianxing Zhan Chengfang Feng Xiaoxiao Liu Xiaoyu Su Danrui Fan Mengyuan Ma Zhonghua Berg Gabriele Li Shaojia Cernava Tomislav 2024-08-05 Aspergillus cvjetkovicii protects against phytopathogens through interspecies chemical signalling in the phyllosphere https://www.nature.com/articles/s41564-024-01781-z Nature Microbiology en 9 11 2862–2876 10.1038/s41564-024-01781-z 2058-5276 2024 2024 subscription Exogenous application of 2,4-DTBP has also been shown to provide similar protective effects against R. solani in cucumber, maize, soybean and tomato to varying degrees. 2,4-DTB's antioxidant activity has a direct scavenging effect on reactive oxygen species (ROS) in R. solani, leading to the repression of RsAMT1 (an ammonium transporter gene) transcription. RsAMT1 is essential for R. solani pathogenicity, hyphal growth and sclerotia formation. RsAMT1 is activated by RsbZIP, a transcription factor dependent on ROS homeostasis. ROS deficiency caused by 2,4-DTBP suppresses the transcriptional switch of the bZIP-AMT1 pathway, leading to a reduction in R. solani pathogenicity. Rice leaf cultivars enriched with Aspergillus cvjetkovicii and 2,4-DTBP demonstrate a reduced area of R. solani-associated necrotic lesions. 2,4-DTBP has shown defensive activity against other rice phytopathogens, including Fusarium fujikuroi, and is non-toxic to resistant host plants. See also 2,6-Di-tert-butylphenol References Category:Antioxidants Category:Alkylphenols Category:Tert-butyl compounds