2,4-Di-tert-butylphenol

2,4-Di-tert-butylphenol
Names
Preferred IUPAC name
2,4-Di-tert-butylphenol
Other names
  • 2,4-Bis(1,1-dimethylethyl)phenol
  • 2,4-Bis(tert-butyl)phenol
  • 2,4-Di-tert-butylhydroxybenzene
Identifiers
3D model (JSmol)
ChEBI
ChEMBL
ChemSpider
ECHA InfoCard 100.002.303
EC Number
  • 202-532-0
UNII
  • InChI=1S/C14H22O/c1-13(2,3)10-7-8-12(15)11(9-10)14(4,5)6/h7-9,15H,1-6H3
    Key: ICKWICRCANNIBI-UHFFFAOYSA-N
  • CC(C)(C)c1ccc(O)c(c1)C(C)(C)C
Properties
C14H22O
Molar mass 206.329 g·mol−1
Appearance White crystalline solid
Odor phenolic, medical
Density 0.887
Melting point 56.8 °C (134.2 °F; 329.9 K)
Boiling point 264.2 °C (507.6 °F; 537.3 K)
33 mg/L at 25 °C, pH 6 - 7
Vapor pressure 5 Pa @ 38°C
Acidity (pKa) 11.6
Hazards
GHS labelling:[1]
Warning
H315, H318, H410
P264, P273, P280, P302+P352, P305+P351+P338, P310, P332+P313, P362, P391, P501
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
Infobox references

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.[2]

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.[3]

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 [4]. 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-DTBP’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.[4]

See also

References

  1. ^ "Registration Dossier - ECHA". echa.europa.eu. Retrieved 31 August 2024.
  2. ^ Zhao, F; Wang, P; Lucardi, RD; Su, Z; Li, S (6 January 2020). "Natural Sources and Bioactivities of 2,4-Di-Tert-Butylphenol and Its Analogs". Toxins. 12 (1): 35. doi:10.3390/toxins12010035. PMC 7020479. PMID 31935944.
  3. ^ Yadav, Ganapati D; Doshi, Nirav S (September 2002). "Alkylation of phenol with methyl-tert-butyl ether and tert-butanol over solid acids: efficacies of clay-based catalysts". Applied Catalysis A: General. 236 (1–2): 129–147. Bibcode:2002AppCA.236..129Y. doi:10.1016/S0926-860X(02)00300-9.
  4. ^ a b 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". Nature Microbiology. 9 (11) (published 2024): 2862–2876. doi:10.1038/s41564-024-01781-z. ISSN 2058-5276.{{cite journal}}: CS1 maint: date and year (link)
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