13331-20-9

Basic information

• Product Name: 2-butylbenzene-1,3-diol
• Synonyms: 1,3-benzenediol, 2-butyl-; 2-Butylbenzene-1,3-diol; Butylresorcinol
• CAS NO: 13331-20-9
• Molecular Formula: C₁₀H₁₄O₂
• Molecular Weight: 166.217
• Mol File: 13331-20-9.mol
• Article Data: 1

Chemical Properties

• Boiling Point: 315.412°C at 760 mmHg
• Flash Point: 153.414°C
• Density: 1.093g/cm³
• Vapor Pressure: 0mmHg at 25°C
• Refractive Index: 1.555
• CAS DataBase Reference: 2-butylbenzene-1,3-diol(CAS DataBase Reference)
• NIST Chemistry Reference: 2-butylbenzene-1,3-diol(13331-20-9)
• EPA Substance Registry System: 2-butylbenzene-1,3-diol(13331-20-9)

Safety Data

• Hazardous Substances Data: 13331-20-9(Hazardous Substances Data)

Upstream product

• 151-10-0 1,3-Dimethoxybenzene 
• 16929-66-1 1-n-butyl-2,6-dimethoxybenzene 

Downstream Products

• 152610-06-5 2-(3-hydroxy-2-butylphenoxy)-benzoic acid methyl ester 
• 152610-07-6 2-[2-butyl-3-[3-[2-ethyl-4-(4-fluorophenyl)-5-(phenylmethoxy)phenoxy]propoxy]phenoxy]-benzoic acid methyl ester 
• 1026727-09-2 2-{2-Butyl-3-[3-(5-ethyl-4'-fluoro-2-hydroxy-biphenyl-4-yloxy)-propoxy]-phenoxy}-benzoic acid methyl ester 

Relevant articles and documents

Synthetic and structure/activity studies on acid-substituted 2- arylphenols: Discovery of 2-[2-propyl-3-[3-[2-ethyl-4-(4-fluorophenyl)-5- hydroxyphenoxy]-propoxy]phenoxy]benzoic acid, a high-affinity leukotriene B4 receptor antagonist

Structural derivatives of LY255283 have been studied as receptor antagonists of leukotriene B4. Substitution of the 2-hydroxyacetophenone subunit of 1 (LY255283) with a 2-arylphenol group provided entry into several new series that feature various mono- and diacidic core functionality. These new analogues, the subject of a broad structure-activity investigation, displayed significantly increased in vitro and in vive activity as receptor antagonists of LTB4. A series of diaryl ether carboxylic acids demonstrated especially interesting activity and led to the discovery of compound 43b, 2- [2-propyl-3-[3-[2-ethyl-4-(4-fluorophenyl)-5-hydroxyphenoxy]- propoxy]phenoxy]benzoic acid (LY293111), a 2-arylphenol-substituted diaryl ether carboxylic acid which displayed potent binding to human neutrophils (IC50 = 17 ± 4.6 nM) and guinea pig lung membranes (IC50 = 6.6 ± 0.71 nM), inhibition of LTB4-induced expression of the CD11b/CD18 receptor on human neutrophils (IC50 = 3.3 ± 0.81 nM), and inhibition of LTB4-induced contraction of guinea pig lung parenchyma (pK(B) = 8.7 ± 0.16). In vivo, 43b demonstrated potent activity in inhibiting LTB4-induced airway obstruction in the guinea pig when dosed by the oral (ED50 = 0.40 mg/kg) or intravenous (ED50 = 0.014 mg/kg) routes. A specific LTB4 receptor antagonist, 43b had little effect on inhibiting contractions of guinea pig lung parenchyma induced by leukotriene D4 (LTD4), histamine, carbachol, or U46619. Compound 43b has been chosen as a clinical candidate and is currently in phase I studies for a variety of inflammatory diseases.