101432-05-7

Basic information

• Product Name: 1,4-BIS(3,4-DIHYDROXYPHENYL)BUTANE
• Synonyms: 1,4-BIS(3,4-DIHYDROXYPHENYL)BUTANE
• CAS NO: 101432-05-7
• Molecular Formula: C₁₆H₁₈O₄
• Molecular Weight: 0
• Mol File: 101432-05-7.mol
• Article Data: 5

Chemical Properties

• Appearance: /
• CAS DataBase Reference: 1,4-BIS(3,4-DIHYDROXYPHENYL)BUTANE(CAS DataBase Reference)
• NIST Chemistry Reference: 1,4-BIS(3,4-DIHYDROXYPHENYL)BUTANE(101432-05-7)
• EPA Substance Registry System: 1,4-BIS(3,4-DIHYDROXYPHENYL)BUTANE(101432-05-7)

Safety Data

• Hazardous Substances Data: 101432-05-7(Hazardous Substances Data)

Usage

Chemical compound

Yes

Type

Bisphenol

Usage

a. Production of epoxy resins
b. Manufacturing of coatings, adhesives, and electrical insulators
c. Synthesis of certain types of polycarbonate plastics
d. Starting material for the production of flame retardants

Environmental concerns

Potential for endocrine disruption and persistence in the environment

Health concerns

Potential endocrine disruption

Interest in alternatives

Increasing interest in developing alternative chemical compounds with similar properties but with reduced environmental and health impacts.

Upstream product

• 855242-51-2 1,4-bis-benzo[1,3]dioxol-5-yl-butane 
• 3929-47-3 3-(3,4-dimethoxyphenyl)-1-propanol 
• 57293-20-6 <3-(3,4-dimethoxyphenyl)propyl>triphenylphosphonium bromide 
• 3945-85-5 1-bromo-3-(3,4-dimethoxyphenyl)propane 
• 120-14-9 3,4-dimethoxy-benzaldehyde 
• 121152-99-6 1t,4t-bis-benzo[1,3]dioxol-5-yl-buta-1,3-diene 
• 94757-25-2 1,4-bis-(3,4-dimethoxy-phenyl)-buta-1,3-diene 
• 120-57-0 piperonal 
• 611211-74-6 5-[4-(3,4-dimethoxyphenyl)butyl]benzo[1,3]dioxole 
• 52417-29-5 4-(3,4-dimethoxyphenyl)butanal 
• 56880-86-5 4-(3,4-dimethoxyphenyl)butan-1-ol 
• 946412-85-7 4-[4-(4-chlorophenyl)butyl]-1,2-dimethoxybenzene 
• 946412-81-3 1-(1,3-benzodioxol-5-yl)-4-(3,4-dimethoxyphenyl)butan-1-one 
• 946412-79-9 1-(3,4-dichlorophenyl)-4-(3,4-dimethoxyphenyl)butan-1-one 

Downstream Products

• 1018685-52-3 1,4-bis{3,4-bis[2-(1-methyl-piperazin-4-yl)-ethoxy]phenyl}-butane 
• 1018685-49-8 1,4-bis{3,4-bis[3-(piperidin-1-yl)propoxy]phenyl}-butane 
• 1018685-54-5 1,4-bis{3,4-bis(2-(N,N'-dimethylamino)-ethoxy)phenyl}-butane 
• 1018685-48-7 1,4-bis-(3,4-ethoxyphenyl) butane 

Relevant articles and documents

Structural optimization of natural product nordihydroguaretic acid to discover novel analogues as AcrB inhibitors

Drug efflux pumps confer multidrug resistance to dangerous bacterial pathogens which makes these proteins promising drug targets. Herein, we present initial chemical optimization and structure-activity relationship (SAR) data around a previously described efflux pump inhibitor, nordihydroguaretic acid (NDGA). Four series of novel NDGA analogues that target Escherichia coli AcrB were designed, synthesized and evaluated for their ability to potentiate the activity of antibiotics, to inhibit AcrB-mediated substrate efflux and reduce off-target activity. Nine novel structures were identified that increased the efficacy of a panel of antibiotics, inhibited drug efflux and reduced permeabilization of the bacterial outer and inner membranes. Among them, WA7, WB11 and WD6 possessing broad-spectrum antimicrobial sensitization activity were identified as NDGA analogues with favorable properties as potential AcrB inhibitors, demonstrating moderate improvement in potency as compared to NDGA. In particular, WD6 was the most broadly active analogue improving the activity of all four classes of antibacterials tested.

TETRA-O-SUBSTITUTED BUTANE-BRIDGE MODIFIED NDGA DERIVATIVES, THEIR SYNTHESIS AND PHARMACEUTICAL USE

The present invention relates to nordihydroguaiaretic acid derivative compounds, namely, butane bridge modified nordihydroguaiaretic acid (NDGA) compounds and butane bridge modified tetra-O-substituted NDGA compounds, pharmaceutical compositions containing them, methods of making them, and methods of using them and kits including them for the treatment of diseases and disorders, in particular, diseases resulting from or associated with a virus infection, such as HIV infection, HPV infection, or HSV infection, an inflammatory disease, such as various types of arthritis and inflammatory bowel diseases, metabolic diseases, such as diabetes and hypertension, or a proliferative disease, such as diverse types of cancers.

1,4-bis (dihydroxyphenyl) butane and analogs

A grignard synthesis of pharmacologically active 1,4-bis(dihydroxyphenyl)butane and analogs, as well as novel intermediates, is provided, comprising preparing a grignard reagent preferably, a 3,4-dialkoxyphenyl propyl magnesium bromide, which may be reacted with carbonyl compounds to form intermediates of desired end products, said carbonyl compounds preferably being 3,4-dialkoxybenzaldehydes. The resulting alcohol is converted to a corresponding ether or siloxy compound, at the carbonyl site. The oxy-substituent is cleaved off; and the benzene ring or rings dealkylated to leave hydroxy substituents on the rings.