157360-23-1

Basic information

• Product Name: 4,6-Di-tert-butyl-2,2-dipentyl-2,3-dihydrobenzofuran-5-ol
• Synonyms: BO-653
• CAS NO: 157360-23-1
• Molecular Formula: C₂₆H₄₄O₂
• Molecular Weight: 388.63938
• Mol File: 157360-23-1.mol

Chemical Properties

• CAS DataBase Reference: 4,6-Di-tert-butyl-2,2-dipentyl-2,3-dihydrobenzofuran-5-ol(CAS DataBase Reference)
• NIST Chemistry Reference: 4,6-Di-tert-butyl-2,2-dipentyl-2,3-dihydrobenzofuran-5-ol(157360-23-1)
• EPA Substance Registry System: 4,6-Di-tert-butyl-2,2-dipentyl-2,3-dihydrobenzofuran-5-ol(157360-23-1)

Safety Data

• Hazardous Substances Data: 157360-23-1(Hazardous Substances Data)

Upstream product

• 75169-17-4 4-acetoxy-3,5-di-tert-butylanisole 
• 1252024-18-2 C₂₆H₄₆O₃ 
• 173662-47-0 4-acetoxy-3,5-di-tert-butyl-2-(1-hydroxy-2-pentylheptyl)phenol 
• 157360-60-6 4-acetoxy-2-aminomethyl-3,5-di-tert-butylphenol 
• 157360-29-7 5-acetoxy-4,6-di-tert-butyl-2-hydroxybenzaldehyde 
• 489-01-0 2,6-Di-t-butyl-4-methoxyphenol 
• 390393-99-4 5-acetoxy-4,6-di-tert-butyl-2,3-dihydro-2,2-dipenthylbenzofuran 
• 32102-41-3 4-acetoxy-3,5-di-tert-butylphenol 

Relevant articles and documents

A new strategy for the synthesis of 4,6-di-tert-butyl-2,2-dipentyl-2,3- dihydro-5-benzofuranol (BO-653), a potent antiatherogenic antioxidant

An efficient alternative route to 4,6-di-tert-butyl-2,2-dipentyl-2,3- dihydro-5-benzofuranol (BO-653), a potent antiatherogenic antioxidant, has been developed by the application of the base-promoted dienone- phenol rearrangement reaction. A decisive effect of MgBr2 in the reaction of Grignard reagents is also described.

Design and synthesis of 4,6-di-tert-butyl-2,3-dihydro-5-benzofuranols as a novel series of antiatherogenic antioxidants

Antioxidants have been considered as potential antiatherogenic agents by inhibiting oxidation of low-density lipoprotein (LDL), albeit vitamin E, a natural antioxidant, has failed to show reduction on atherosclerosis in clinical trials. We have rationally

Process for preparation of a benzofuran derivative

An industrially useful process for producing benzofuran derivatives of formula (1) by formylating a compound of formula (2) (where A1 is a protective group), followed by reaction with a compound of formula (4) (where X1 is a halogen atom), then performing a cyclizing reaction and subsequently performing a reaction for hydroxyl group deprotection.

Intimal thickening inhibitory agent

An intimal thickening inhibitory agent comprising, as an active ingredient, a compound represented by formula (1): STR1 wherein X represents an oxygen atom or a group of formula (2): STR2 wherein n represents an integer of from 0 to 2, R1 represents a hydrogen atom or an acyl group; R2 represents a hydrogen atom, a lower alkyl group or a lower alkenyl group; R3 represents a lower alkyl group; and R4, R5, and R6, which may be the same or different, each represent a hydrogen atom or a substituted or unsubstituted alkyl group; or R3 and R4 may be taken together to form a 5-membered ring; or R5 and R6 may be taken together to form a cycloalkyl group; provided that R6 is nil when R3 and R4 are taken together to form benzofuran or benzo[b]thiophene.

Prophylactic/therapeutic agents for atherosclerosis

PCT No. PCT/JP98/01861 Sec. 371 Date Nov. 8, 1999 Sec. 102(e) Date Nov. 8, 1999 PCT Filed Apr. 23, 1998 PCT Pub. No. WO98/50025 PCT Pub. Date Nov. 12, 1998Herein disclosed are prophylactic/therapeutic agents for atherosclerosis containing a compound of general formula (1): wherein R1 represents a hydrogen atom or an acyl group, R2 represents a lower alkyl group, R3 represents a hydrogen atom or a lower alkyl group, and R4, R5 and R6 represent a hydrogen atom, an alkyl group, an alkenyl group, an alkynyl group or an aryl group, or R2 and R4 together with the oxygen atom may form a furan or dihydrofuran ring, or R5 and R6 may combine to form a cycloalkyl group or a heterosubstituted cycloalkyl group in which one or more methylene groups of the cycloalkyl group are replaced by oxygen, sulfur or alkyl-substituted nitrogen atoms, a possible optically active isomer or a pharmaceutically acceptable salt thereof, as an active ingredient.

Stability and reactivity of aryloxyl radicals derived from a novel antioxidant BO-653 and related compounds. Effects of substituent and side chain in solution and membranes

2,3-Dihydro-5-hydroxy-2,2-dipentyl-4,6-di-tert-butylbenzofuran (BO-653) is a novel antioxidant designed as a drug for inhibition of lipid peroxidation in vivo. To understand the dynamics of action of BO-653 as an antioxidant, the effects of substituents and side chains on the stability and reactivity of the BO-653 derived radical were studied and compared with the aryloxyl radicals derived from related compounds including α-tocopherol. The rate constants for the reactions of the aryloxyl radicals with themselves, lipid, hydroperoxide, and ascorbate were measured with a stopped-flow electron spin resonance (ESR) spectroscope equipped with a rapid mixing device. The ortho substituents exerted profound effects on the rate of bimolecular decay reactions and the reaction with ascorbic acid, while the effects on the reactions with methyl linoleate and tert-butyl hydroperoxide were much less significant. The side chain at the 2-position did not exert any effect in organic solution but the two pentyl side chains, when compared with two methyl side chains, diminished the apparent reactivities in the liposomal membranes.

4,6-Di-t-butyl-dihydrobenzofuran-5-ol and its derivatives

Compounds represented by the general formula as well as intermediates for the synthesis of thereof: STR1 where R1 is a hydrogen atom or an acyl group; R2 is a lower alkyl group; R3 is a hydrogen atom or a lower alkyl group