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Chemical Structure| 128-37-0 Chemical Structure| 128-37-0

Structure of Butylated hydroxytoluene
CAS No.: 128-37-0

Chemical Structure| 128-37-0

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Butylated hydroxytoluene is an antioxidant widely used in foods and in food-related products. Butylated hydroxytoluene is a Ferroptosis inhibitor.

Synonyms: BHT; NSC 6347

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Product Citations

Product Citations

Hamilton, Mason D ;

Abstract: compounds are some of the most synthetically versatile compounds in organic chemistry due to the many valuable transformations of the C-B bond. This synthetic versatility combined with the pharmacophoric nature of has led to an increased interest in the one-pot difunctionalization of vinyl arenes using CO2 and . Recently, much progress has been made to improve the scope and versatility of boracarboxylation reactions to now include electron-deficient and α-methyl substituted vinyl arenes. However, the potential transformations of boracarboxylated products have remained unexplored. Here, methodologies to transform the β-aryl alkylboronic ester into new C-C, C-N, and C-X bonds will be described. Medically relevant 2,3-diarylpropionic acids can now be accessed via a two-step protocol consisting of boracarboxylation of a vinyl arene followed by a palladium(0)-catalyzed . This methodology provides access to both the α- and β-regioisomers independently whereas traditional strategies to access these compounds afford only one regioisomer, and in most cases, a mixture of regioisomers. Interesting biaryl and heterocyclic products can be accessed and to demonstrate the synthetic utility of this protocol, a glucagon receptor antagonist was synthesized in 4 less steps than the previously reported method while maintaining similar yields. The transformative capability of boracarboxylated products is further demonstrated through a base-_x005f_x0002_and external oxidant-free copper(II)-catalyzed amination to generate β2-amino acid derivatives. While the β-carboxylic acid was intolerable to the conditions, protection via esterification or amidation allowed for successful amination of the alkylboronic ester to occur. Amination of two bora-NSAIDs, bora-ibuprofen and bora-naproxen, was successful and a number of cyclic and acyclic amines are suitable for the transformation. Preliminary mechanistic work suggests that this amination does not proceed through a free-radical intermediate but rather a two-electron pathway. Finally, a novel halogenation of boracarboxylated products is achieved to generate the corresponding β-aryl alkyl halides. This methodology is performed in a base, metal, and additive free manner that utilizes cheap and readily available sources of electrophilic halide. Both bromination and iodination are demonstrated and can be achieved on a variety of electron-rich and electron-poor boracarboxylated products and can subsequently undergo amination to provide an alternative route to β2-amino acid derivatives. Mechanistic experiments suggest that the β-carboxylic acid is required to achieve the activation of the C-B bond. Radical trapping experiments also indicate that this transformation may occur through the formation of an alkyl radical although this is unlikely.

Keywords: Boracarboxylation ; alkylboronic ester ; ; oxidative amination ; 2,3-diarylpropionic acid ; β2-amino acid

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Alternative Products

Product Details of Butylated hydroxytoluene

CAS No. :128-37-0
Formula : C15H24O
M.W : 220.35
SMILES Code : CC1=CC(=C(O)C(=C1)C(C)(C)C)C(C)(C)C
Synonyms :
BHT; NSC 6347
MDL No. :MFCD00011644
InChI Key :NLZUEZXRPGMBCV-UHFFFAOYSA-N
Pubchem ID :31404

Safety of Butylated hydroxytoluene

GHS Pictogram:
Signal Word:Danger
Hazard Statements:H302-H315-H319-H360-H373-H410
Precautionary Statements:P273-P260-P270-P202-P201-P264-P280-P302+P352-P391-P337+P313-P305+P351+P338-P308+P311-P362+P364-P332+P313-P301+P312+P330-P405-P501
Class:9
UN#:3077
Packing Group:

Isoform Comparison

Biological Activity

In Vitro:

Cell Line
Concentration Treated Time Description References
ELT-3 cells 0.1–25 μM 24 and 48 h To evaluate the effect of BHT on ELT-3 cell proliferation, results showed that all concentrations significantly increased cell viability after 48 h of treatment Nutrients. 2021 Aug 31;13(9):3074
SH-SY5Y human neuroblastoma cells 30 nM BHT prevented RSL3- and ML162-induced ferroptosis by inhibiting the oxidation of cellular membrane lipids Mol Med. 2024 Nov 8;30(1):204

In Vivo:

Species
Animal Model
Administration Dosage Frequency Description References
Mice A/J and BALB/cBy mice Intraperitoneal injection 150 mg/gm (week 1), 200 mg/gm (thereafter) Weekly for 6 weeks BHT elicits chronic inflammation, increases tumor multiplicity, and promotes the formation of Kras mutational spectra similar to those in human smokers and never-smokers. J Thorac Oncol. 2010 Feb;5(2):254-7

Protocol

Bio Calculators
Preparing Stock Solutions 1mg 5mg 10mg

1 mM

5 mM

10 mM

4.54mL

0.91mL

0.45mL

22.69mL

4.54mL

2.27mL

45.38mL

9.08mL

4.54mL

Dissolving Methods
Please choose the appropriate dissolution scheme according to your animal administration guide.For the following dissolution schemes, clear stock solution should be prepared according to in vitro experiments, and then cosolvent should be added in turn:

in order to ensure the reliability of the experimental results, the clarified stock solution can be properly preserved according to the storage conditions; The working fluid for in vivo experiment is recommended to be prepared now and used on the same day;

The percentage shown in front of the following solvent refers to the volume ratio of the solvent in the final solution; If precipitation or precipitation occurs in the preparation process, it can be assisted by heating and/or ultrasound.
Protocol 1
Protocol 2
The prepared working fluid is recommended to be prepared now and used up as soon as possible in a short period of time. The percentage shown in front of the following solvent refers to the volume ratio of the solvent in the final solution; If precipitation or precipitation occurs in the preparation process, it can be assisted by heating and/or ultrasound.
Protocol 1

References

 

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