4167-73-1

Usage

Uses

Used in Polymer and Plastics Industry:
2-(3-HYDROXY-3-METHYLBUTYL)PHENOL is used as an antioxidant and UV stabilizer for enhancing the durability and stability of polymers and plastics. Its presence helps protect materials from degradation caused by exposure to heat, light, and oxygen, thereby extending their service life and maintaining their physical properties.
Used in Pharmaceutical Synthesis:
In the pharmaceutical industry, 2-(3-HYDROXY-3-METHYLBUTYL)PHENOL serves as a key chemical intermediate in the synthesis of various drugs. Its unique structure allows for the development of new pharmaceutical compounds with potential therapeutic benefits.
Used in Organic Synthesis:
2-(3-HYDROXY-3-METHYLBUTYL)PHENOL is utilized as a chemical intermediate in organic synthesis, enabling the creation of a wide range of organic compounds for various applications, from specialty chemicals to advanced materials.
Used in Anti-Inflammatory Applications:
HMBP has been studied for its potential as an anti-inflammatory agent, making it a candidate for use in medical applications where reducing inflammation is necessary for treatment or symptom management.
Used in Research and Development:
2-(3-HYDROXY-3-METHYLBUTYL)PHENOL is also used in research and development settings to explore its therapeutic effects and potential applications in various medical fields, including the development of new drugs and therapies.

Upstream product

• 917-64-6 methyl magnesium iodide 
• 119-84-6 C₆H₄(CH₂CH₂C(O)O) 
• 78-79-5 isoprene 
• 108-95-2 phenol 
• 676-58-4 methylmagnesium chloride 
• 496-16-2 2.3-dihydrobenzofuran 
• 67-64-1 acetone 
• 91-64-5 coumarin 
• 75-24-1 trimethylaluminum 
• 157953-24-7 1-(3-hydroxy-3-methylbutynyl)-2-tosyloxybenzene 
• 20921-04-4 ethyl 3-(2-hydroxyphenyl)propanoate 
• 115-19-5 2-methyl-but-3-yn-2-ol 
• 84672-48-0 2-bromophenyl 4-methylbenzenesulfonate 

Downstream Products

• 1198-96-5 2,2-dimethylchroman 
• 61370-82-9 (2,2-dimethylchroman-6-yl)methanol 
• 61370-75-0 3,4-dihydro-2,2-dimethyl-2H-1-benzopyran-6-carboxaldehyde 
• 12772-83-7 3-[2,2-dimethyl-3,4-dihydro-(2H)-benzopyran-6-yl]-2E-propenoic acid 
• 1442439-46-4 4-[[[8-bromo-2,2-dimethyl-4-(4-methylphenyl)-6-chromanyl]carbonyl]amino]benzoic acid 
• 1442439-45-3 ethyl 4-[[[8-bromo-2,2-dimethyl-4-(4-methylphenyl)-6-chromanyl]carbonyl]amino]benzoate 
• 1234847-99-4 C₂₄H₂₈F₂O₄ 
• 1234841-45-2 3-(4-((2,2-dimethylchroman-8-yl)methoxy)-3,5-difluorophenyl)-2-methylpropanoic acid 
• 355837-47-7 (2,2-dimethylchroman-8-yl)methanol 
• 82553-56-8 3,4-dihydro-2,2-dimethyl-8-carboxy-2H-1-benzopyran 
• 157953-28-1 Benzoic acid 2-(3-methyl-but-2-enyl)-phenyl ester 
• 1128-92-3 2-prenylphenol 
• 192762-74-6 ethyl 2,6-difluoro-4-({[8-bromo-2,2-dimethyl-4-(4-methylphenyl)-6-chromanyl]carbonyl}amino)benzoate 
• 192762-73-5 ethyl 2-fluoro-4-[[[8-bromo-2,2-dimethyl-4-(4-methylphenyl)-6-chromanyl]carbonyl]amino]benzoate 

Relevant academic research and scientific papers

RAR-ALPHA COMPOUNDS FOR INFLAMMATORY DISEASE AND MALE CONTRACEPTION

Modulators of retinoid acid receptor-alpha (RARα) of formula (I) are provided herein, as well as pharmaceutical compositions and methods relating thereto.

Practical synthesis of a chromene analog for use as a retinoic acid receptor alpha antagonist lead compound

Retinoic acid receptor alpha (RARα) selective compounds may guide the design of drugs that can be used in conjunction with hormonal adjuvant therapy in the treatment of breast cancer. Herein we report a modified synthesis of a known RARα antagonist, 2-fluoro-4-[[[8-bromo-2,2-dimethyl-4-(4- methylphenyl)chroman-6-yl]carbonyl]amino]benzoic acid and a synthesis of its unknown, desfluoro analog, 4-[[[8-bromo-2,2-dimethyl-4-(4-methylphenyl)chroman- 6-yl]carbonyl]amino]benzoic acid. The modified route allows for facile reaction workups, increased yields, lower cost and incorporates a green alternative step. Structure-activity relationship studies determined through functional cell-based assays, demonstrated antagonism to RARα for both compounds. Molecular modeling within the RARα binding pocket was used to compare binding interactions of the desfluoro analog to a known RAR antagonist.

GPR120 RECEPTOR AGONISTS AND USES THEREOF

GPR120 agonists are provided. These compounds are useful for the treatment of metabolic diseases, including Type II diabetes and diseases associated with poor glycemic control.

GPR120 RECEPTOR AGONISTS AND USES THEREOF

GPR120 agonists are provided. These compounds are useful for the treatment of metabolic diseases, including Type II diabetes and diseases associated with poor glycemic control.

Reductive lithiation of cyclic benzofused ethers: A source of oxygen-functionalised organolithium compounds

The reaction of 2,3-dihydrobenzofuran (1) with lithium and a catalytic amount of 4,4′-di-tert-butylbiphenyl (DTBB, 5%) in THF at 0°C for 1.5h, followed by addition of an electrophile [E+=H2O, tBuCHO, PhCH2CHO, Ph(CH2)2CHO, PhCHO, furfural, Me2CO, Et2CO, cyclopentanone, cyclohexanone, cyclooctanone, (-)-menthone] in THF at -78°C gives, after hydrolysis, compounds 3. Some diols 3 are easily transformed into 2-substituted chromans 6 under acidic reaction conditions. The reductive lithiation of chroman (7) at 20°C for 3h leads exclusively to the intermediate 8, which is formed through a dearylation process, and isomerises to the apparently more stable benzylic intermediate 9. The reaction of these intermediates with different electrophiles {E+=tBuCHO, PhCHO, furfural, Me2CO, [CH3(CH2)4]2CO, cyclopentanone, cyclohexanone, (-)-menthone, Ph2CO}, at -78°C in THF leads, after hydrolysis, to a mixture of regioisomers 10 and 11. The reaction of 2,3-benzofuran (12) with an excess of lithium and a catalytic amount of DTBB (5%) in THF at 0°C for 45min leads to dianionic intermediate 13 through a dealkylation process, which after hydrolysis gives 2-vinylphenol 14. In the case of 4H-chromene (15), reductive opening is performed at 20°C for 45min, a mixture of dearylation and dealkylation intermediates 16 and 17, respectively, is obtained (2:1 ratio) giving, after hydrolysis, 3-phenylpropanal (18) and 2-allylphenol (19).

Addition of trialkylaluminum reagents to glyconolactones. Synthesis of 1-C-methyl GlcNAc oxazoline and thiazoline

Addition of carbon nucleophiles to 2-acetamido-2-deoxygluconolactones fails for many reagents, but trialkylaluminums add alkyl smoothly. The product of methyl addition to 2-acetamido-2-deoxy-D-gluconolactone has been converted to 1-C-methyl GlcNAc thiazoline, a potential N-acetylhexosaminidase inhibitor, and to an O-protected 1-C-Me GlcNAc oxazoline, a potential 1-C-Me GlcNAc donor.

Organolithium reagents from alkyl phenyl ethers

The reaction of primary alkyl or vinyl phenyl ethers (1) as well as 2,3- dihydrobenzofuran (3) with an excess of lithium powder and a catalytic amount of DTBB (5 %) in THF at room temperature leads to the corresponding organolithium intermediates, which by treatment with different electrophiles [H2O, D2O, Me3SiCl, Bu(t)CHO, PhCHO, Me2CO, Et2CO, (CH2)4CO, (CH2)5CO, PhCOMe] and final hydrolysis affords the expected products 2 and 4.

Identification of highly potent retinoic acid receptor α-selective antagonists

The syntheses and full retinoid receptor characterization of a novel series of retinoic acid receptor α (RARα) antagonists, 1-5, are described. These compounds bind with high affinity to RARα but were completely inactive in gene transactivation. They were also potent and effective antagonists of retinoic acid (RA) induced gene transcription at RARα. Compounds 1-5 exhibited varying degrees of selectivity for RARα relative to RARβ/γ, with compound 5 being the most selective in both binding and functional antagonism assays. These compounds will be invaluable tools in delineating the physiological roles of RARα in development and in the adult animal and may themselves be useful therapeutic agents in human diseases associated with RARα.

REGIOSELECTIVE PRENYLATION OF PHENOLS BY PALLADIUM CATALYST: SYNTHESES OF PRENYLPHENOLS AND CHROMANS

The palladium-catalyzed coupling reaction of iodophenols (1) with 2-methyl-3-butyn-2-ol gave alkynylphenols (2).Catalytic hydrogenation of 2 over Raney nickel and the subsequent dehydration of the resultant alkylphenols (3) gave regioselectively the desired prenylphenols (4).Dehydration of alkylphenols (3f-h) gave chromans (7).

Chroman esters of phenols and benzoic acids having retinoid-like activity

Retinoid like activity is exhibited by compounds of the formula STR1 wherein the R 1 -R 7 groups are independently H or straight chain or branched chain lower alkyl or cycloalkyl of 1 to 6 carbons; X symbolizes an ester or thioester linkage, Y is cycloalk