111050-72-7

Basic information

• Product Name: 1-((3,5-dichloro)-2,6-dihydroxy-4-methoxyphenyl)-1-hexanone
• Synonyms: 1-((3,5-dichloro)-2,6-dihydroxy-4-methoxyphenyl)-1-hexanone;1-(3,5-Chloro-2,6-dihydroxy-4-methoxyphenyl)-1-Hexanone;1-(3,5-dichloro-2,6-dihydroxy-4-methoxyphenyl)hexan-1-one
• CAS NO: 111050-72-7
• Molecular Formula: C₁₃H₁₆Cl₂O₄
• Molecular Weight: 307.17
• Mol File: 111050-72-7.mol
• Article Data: 4

Chemical Properties

• Boiling Point: 434.3°Cat760mmHg
• Flash Point: 216.5°C
• Appearance: white to beige/
• Density: 1.325g/cm³
• Vapor Pressure: 3.77E-08mmHg at 25°C
• Refractive Index: 1.56
• Storage Temp.: 2-8°C
• Solubility: DMSO: soluble20mg/mL, clear
• CAS DataBase Reference: 1-((3,5-dichloro)-2,6-dihydroxy-4-methoxyphenyl)-1-hexanone(CAS DataBase Reference)
• NIST Chemistry Reference: 1-((3,5-dichloro)-2,6-dihydroxy-4-methoxyphenyl)-1-hexanone(111050-72-7)
• EPA Substance Registry System: 1-((3,5-dichloro)-2,6-dihydroxy-4-methoxyphenyl)-1-hexanone(111050-72-7)

Safety Data

• WGK Germany: 3
• Hazardous Substances Data: 111050-72-7(Hazardous Substances Data)

Usage

Description

1-((3,5-dichloro)-2,6-dihydroxy-4-methoxyphenyl)-1-hexanone, also known as DIF-1, is a hexaphenone compound characterized by the presence of two chloro substituents at positions 3 and 5, two hydroxy substituents at positions 2 and 6, and a single methoxy substituent at position 4. It is a secreted, chlorinated molecule that plays a crucial role in controlling cell fate during the development of Dictyostelium cells.

Uses

Used in Cell Growth Regulation:
DIF-1 is used as a cell growth suppressor, promoting differentiation in HL-60 cells. It is a differentiation-inducing factor that helps regulate cell growth and development.
Used in Developmental Processes:
In the field of developmental biology, DIF-1 is used as a signaling molecule to control cell fate during the development of Dictyostelium cells. It plays a vital role in the differentiation and development of these cells, making it an important tool for studying developmental processes.
Used in Pharmaceutical Research:
Due to its unique structure and properties, 1-((3,5-dichloro)-2,6-dihydroxy-4-methoxyphenyl)-1-hexanone has potential applications in pharmaceutical research. Its ability to regulate cell growth and promote differentiation makes it a promising candidate for the development of new drugs targeting various diseases and conditions.

InChI:InChI=1/C13H16Cl2O4/c1-3-4-5-6-7(16)8-11(17)9(14)13(19-2)10(15)12(8)18/h17-18H,3-6H2,1-2H3

Synthetic route

1-(2,6-dihydroxy-4-methoxyphenyl)hexan-1-one (142234-79-5) → 1-(3,5-dichloro-2,6-dihydroxy-4-methoxyphenyl)hexane-1-one (111050-72-7)

Conditions	Yield
With sulfuryl dichloride In methanol; dichloromethane at 20℃;	100%
With sulfuryl dichloride In ethanol; chloroform at 20℃; for 1h;	93%
With sulfuryl dichloride In ethanol; chloroform at 20℃; for 1h;	93%
With sulfuryl dichloride In methanol; dichloromethane at 20℃; for 0.333333h;

5-methoxyresorcinol (2174-64-3) → 1-(3,5-dichloro-2,6-dihydroxy-4-methoxyphenyl)hexane-1-one (111050-72-7)

Conditions	Yield
Multi-step reaction with 2 steps 1: 58 percent / AlCl3 / CH2Cl2 / 3 h / 20 °C 2: 93 percent / SO2Cl2 / ethanol; CHCl3 / 1 h / 20 °C View Scheme
Multi-step reaction with 2 steps 1: aluminum (III) chloride / dichloromethane / 20 °C 2: sulfuryl dichloride / ethanol; chloroform / 1 h / 20 °C View Scheme

Hexanoyl chloride (142-61-0) → 1-(3,5-dichloro-2,6-dihydroxy-4-methoxyphenyl)hexane-1-one (111050-72-7)

Conditions	Yield
Multi-step reaction with 2 steps 1: 58 percent / AlCl3 / CH2Cl2 / 3 h / 20 °C 2: 93 percent / SO2Cl2 / ethanol; CHCl3 / 1 h / 20 °C View Scheme
Multi-step reaction with 2 steps 1: aluminum (III) chloride / dichloromethane / 20 °C 2: sulfuryl dichloride / ethanol; chloroform / 1 h / 20 °C View Scheme

1-(3,5-dichloro-2,6-dihydroxy-4-methoxyphenyl)hexane-1-one (111050-72-7) → 4,6-dichloro-2-hexyl-5-methoxybenzene-1,3-diol

Conditions	Yield
With triethylsilane; trifluoroacetic acid at 20℃; for 8h;	96%

methyl p-toluene sulfonate (80-48-8) + 1-(3,5-dichloro-2,6-dihydroxy-4-methoxyphenyl)hexane-1-one (111050-72-7) → 1-(3,5-dichloro-2,4,6-trimethoxy-phenyl)-hexan-1-one

Conditions	Yield
With potassium carbonate In acetone at 20℃; for 16h;	95%
With potassium carbonate at 20℃; for 16h;	95%

1-(3,5-dichloro-2,6-dihydroxy-4-methoxyphenyl)hexane-1-one (111050-72-7) → (3,5-dichloro-2,4,6-trihydroxyphenyl)-1-hexan-1-one (118222-71-2)

Conditions	Yield
With boron tribromide In dichloromethane for 16h;	40%

Upstream product

• 142-61-0 Hexanoyl chloride 
• 2174-64-3 5-methoxyresorcinol 
• 142234-79-5 1-(2,6-dihydroxy-4-methoxyphenyl)hexan-1-one 

Downstream Products

• 118222-71-2 (3,5-dichloro-2,4,6-trihydroxyphenyl)-1-hexan-1-one 

Relevant articles and documents

Development of novel DIF-1 derivatives that selectively suppress innate immune responses

The multiple pharmacological activities of differentiation-inducing factor-1 (DIF-1) of the cellular slime mold Dictyostelium discoideum led us to examine the use of DIF-1 as a 'drug template' to develop promising seed compounds for drug discovery. DIF-1 and its derivatives were synthesized and evaluated for their regulatory activities in innate immune responses. We found two new derivatives (4d and 5e) with highly selective inhibitory activities against production of the antimicrobial peptide attacin in Drosophila S2 cells and against production of interleukin-2 in Jurkat cells.

Anti-viral compounds

A compound having the formula (I) wherein the substituents are defined herein. Also provided are pharmaceutical compositions including a compound of formula (I) in a pharmaceutical carrier, for treating a disease caused by a picornavirus. Also provided is a method of treating a subject with a disease caused by a picornavirus, including a compound of formula (I) in a pharmaceutical carrier.