605-32-3

Basic information

• Product Name: 2-HYDROXYANTHRAQUINONE
• Synonyms: 10-Anthracenedione,2-hydroxy-9;2-hydroxy-10-anthracenedione;2-hydroxy-9,10-anthracenedione;2-Hydroxy-9,10-anthraquinone;2-hydroxy-anthraquinon;2-Osyanthrachinon;Anthraquinone, 2-hydroxy-;beta-Hydroxyanthraquinone
• CAS NO: 605-32-3
• Molecular Formula: C₁₄H₈O₃
• Molecular Weight: 224.21
• EINECS: 210-085-8
• Product Categories: Anthraquinones;Hydroxyanthraquinones
• Mol File: 605-32-3.mol
• Article Data: 23

Chemical Properties

• Melting Point: 314℃ (acetic acid )
• Boiling Point: 325.61°C (rough estimate)
• Flash Point: 215.7°C
• Appearance: /
• Density: 1.2337 (rough estimate)
• Vapor Pressure: 2.69E-07mmHg at 25°C
• Refractive Index: 1.5400 (estimate)
• Storage Temp.: Inert atmosphere,Room Temperature
• PKA: 7.41±0.20(Predicted)
• CAS DataBase Reference: 2-HYDROXYANTHRAQUINONE(CAS DataBase Reference)
• NIST Chemistry Reference: 2-HYDROXYANTHRAQUINONE(605-32-3)
• EPA Substance Registry System: 2-HYDROXYANTHRAQUINONE(605-32-3)

Safety Data

• Hazard Codes: N
• Statements: 36/37/38-51/53
• Safety Statements: 26-36/37/39-61
• RIDADR: UN 3077 9 / PGIII
• RTECS: CB7250000
• Hazardous Substances Data: 605-32-3(Hazardous Substances Data)

Usage

Description

2-Hydroxyanthraquinone is a red-orange crystalline chemical compound belonging to the anthraquinone group, characterized by its solubility in organic solvents and insolubility in water. It is recognized for its versatile applications, including acting as a photosensitizer in photocatalyst production and serving as an intermediate in chemical synthesis. Its potential extends to pharmaceutical development, antifungal and antibacterial properties, and antioxidant capabilities for managing oxidative stress-related disorders.

Uses

Used in Dye and Pigment Production:
2-Hydroxyanthraquinone is utilized as a key component in the creation of dyes and pigments due to its vibrant red-orange color, providing a wide range of color options for various industries.
Used as a Photosensitizer in Photocatalyst Production:
In the field of photocatalysis, 2-Hydroxyanthraquinone is employed as a photosensitizer, enhancing the efficiency of light-induced chemical reactions, which is crucial for environmental and energy-related applications.
Used as an Intermediate in Chemical Synthesis:
2-Hydroxyanthraquinone serves as an intermediate in the synthesis of other chemicals, contributing to the development of a diverse array of chemical products.
Used in Pharmaceutical Development:
2-HYDROXYANTHRAQUINONE is explored for its potential in pharmaceuticals, indicating its capacity to be a precursor or active ingredient in the formulation of new medications.
Used as an Antifungal and Antibacterial Agent:
2-Hydroxyanthraquinone is studied for its antifungal and antibacterial properties, suggesting its use in healthcare and sanitation to combat microbial infections.
Used in Antioxidant Formulations:
Given its antioxidant properties, 2-Hydroxyanthraquinone is considered for use in formulations aimed at treating or preventing oxidative stress-related disorders, highlighting its potential in the health and wellness sector.

InChI:InChI=1/C14H8O3/c15-8-5-6-11-12(7-8)14(17)10-4-2-1-3-9(10)13(11)16/h1-7,15H

Synthetic route

2-aminoanthraquinone (117-79-3) → 2-hydroxy-9,10-anthraquinone (605-32-3)

Conditions	Yield
Stage #1: 2-aminoanthraquinone With sodium nitrite at 20℃; for 3.5h; Stage #2: With water for 0.5h; Heating; Further stages.;	96%
Stage #1: 2-aminoanthraquinone With sulfuric acid; sodium nitrite Stage #2: With water Reflux;	90%
With sulfuric acid; sodium nitrite 0 deg C, 5 min then rt 30 min; 160 deg C, 12 h;	86%

9,10-phenanthrenequinone (84-65-1) → 2-hydroxy-9,10-anthraquinone (605-32-3) + 1,4-dihydroxy-9,10-anthracenedione (81-64-1)

Conditions	Yield
With sulfuric acid; boric acid for 5h; Product distribution; Mechanism; Irradiation; other time;	A n/a B 81%

9,10-phenanthrenequinone (84-65-1) → 2-hydroxy-9,10-anthraquinone (605-32-3) + anthracen-9(10H)-one (90-44-8) + 1-hydroxyanthraquinone (129-43-1) + bianthronyl (434-84-4)

Conditions	Yield
In sulfuric acid at 15℃; Product distribution; Mechanism; Quantum yield; Irradiation; N2;	A 80% B n/a C n/a D n/a
In sulfuric acid at 15℃; Irradiation;	A 80% B n/a C n/a D n/a

2-(5,5-dimethyl-[1,3,2]dioxaborinan-2-yl)-anthraquinone (867306-40-9) → 2-hydroxy-9,10-anthraquinone (605-32-3)

Conditions	Yield
With sodium hydroxide; dihydrogen peroxide In tetrahydrofuran at 20℃; for 0.25h;	77%

2-carbomethoxy-9,10-anthraquinone (32114-48-0) → 2-hydroxy-9,10-anthraquinone (605-32-3)

Conditions	Yield
With sodium hydroxide; dihydrogen peroxide In tetrahydrofuran at 20℃; for 0.25h;	77%

(anthracene)chromium tricarbonyl → 2-hydroxy-9,10-anthraquinone (605-32-3)

Conditions	Yield
With boric acid tributyl ester; 2,2,6,6-tetramethylpiperidinyl-lithium In tetrahydrofuran at -78℃; for 0.5h;	71%

9,10-phenanthrenequinone (84-65-1) → 2-hydroxy-9,10-anthraquinone (605-32-3) + 1-hydroxyanthraquinone (129-43-1) + 1,4-dihydroxy-9,10-anthracenedione (81-64-1)

Conditions	Yield
With sulfuric acid at 25℃; Irradiation;	A 70% B n/a C n/a
With sulfuric acid at 25℃; Irradiation; prolonged irradiation;	A n/a B 55% C 6%

9,10-phenanthrenequinone (84-65-1) → 2-hydroxy-9,10-anthraquinone (605-32-3) + 1-hydroxyanthraquinone (129-43-1)

Conditions	Yield
With air; sulfuric acid at 25℃; Irradiation;	A n/a B 60%
With air In water; isopropyl alcohol for 0.5h; Product distribution; Ambient temperature; Irradiation; other solvents: CHCl3 + water, dioxane + water, other reaction time: 15 min;
With air; sulfuric acid at 25℃; for 7h; Product distribution; Mechanism; Quantum yield; Irradiation; without air (argon), other time, other concentration of H2SO4, other temperature, other intensity of the light, other wavelenght;

sodium anthraquinone-2-sulfonate → 2-hydroxy-9,10-anthraquinone (605-32-3)

Conditions	Yield
With sodium hydride; Benzaldoxime In tetrahydrofuran; vaseline; N,N-dimethyl acetamide at 60℃; for 3h; Inert atmosphere;	55%

2,3-bis(trimethylsilyloxy)-1,3-butadiene (31411-71-9) + [1,4]naphthoquinone (130-15-4) → 2-hydroxy-9,10-anthraquinone (605-32-3) + hystazarin (483-35-2)

Conditions	Yield
In toluene for 24h; Heating; Yields of byproduct given;	A 54% B n/a
In toluene for 24h; Heating; Yield given. Yields of byproduct given;

(4α,4aβ,9aβ)-9a-acetoxy-4a-chloro-4-methoxy-3,4,4a,9a-tetrahydroanthracene-2,9,10(1H)-trione → 2-hydroxy-9,10-anthraquinone (605-32-3)

Conditions	Yield
With acetic acid; zinc at 20℃; for 3h; Reduction; aromatization;	54%

phthalic anhydride (85-44-9) + 4-bromo-phenol (106-41-2) → 3-bromo-1-hydroxy-9,10-anthraquinone (1116690-18-6) + 2-hydroxy-9,10-anthraquinone (605-32-3) + 1-hydroxyanthraquinone (129-43-1) + 2-hydroxy-3-bromoanthraquinone (72668-05-4) + 1-Bromo-4-hydroxyanthraquinone (6374-82-9)

Conditions	Yield
With aluminum (III) chloride; sodium chloride at 165 - 170℃; for 0.75h; Friedel-Crafts Acylation;	A 24% B 3% C 4% D 8% E 11%

tetrachloromethane (56-23-5) + 2-hydroxy-2,4a-dihydro-anthraquinone → 2-hydroxy-9,10-anthraquinone (605-32-3) + bianthrone (434-85-5)

Conditions	Yield
beim Erhitzen auf Temperaturen oberhalb des Schmelzpunkts;

phthalic anhydride (85-44-9) + phenol (108-95-2) → 2-hydroxy-9,10-anthraquinone (605-32-3) + 1-hydroxyanthraquinone (129-43-1)

Conditions	Yield
With sulfuric acid

1-methyl-4-nitrosobenzene (623-11-0) + 2-hydroxy-2,4a-dihydro-anthraquinone → 2-hydroxy-9,10-anthraquinone (605-32-3) + 1,2-dihydroxy-9,10-anthracenedione (72-48-0)

Conditions	Yield
at 215℃; und Leiten von Luft durch die Reaktionsloesung;

1,2-dihydroxy-9,10-anthracenedione (72-48-0) → 2-hydroxy-9,10-anthraquinone (605-32-3)

Conditions	Yield
With tin(ll) chloride

2-chloroanthracene-9,10-dione (131-09-9) → 2-hydroxy-9,10-anthraquinone (605-32-3)

Conditions	Yield
With ammonia at 215℃; unter Druck;

2-bromoanthracene-9,10-dione (572-83-8) → 2-hydroxy-9,10-anthraquinone (605-32-3) + 1,2-dihydroxy-9,10-anthracenedione (72-48-0)

Conditions	Yield
With potassium hydroxide

2-nitroanthraquinone (605-27-6) + potassium ethoxide (917-58-8) → 2-hydroxy-9,10-anthraquinone (605-32-3) + 2-methoxy-9,10-anthraquinone (3274-20-2)

Conditions	Yield
With methanol

2-nitroanthraquinone (605-27-6) → 2-hydroxy-9,10-anthraquinone (605-32-3) + 2-methoxy-9,10-anthraquinone (3274-20-2)

Conditions	Yield
With methanol; potassium ethoxide

2-sulfo-anthraquinone (84-48-0) → 2-hydroxy-9,10-anthraquinone (605-32-3)

Conditions	Yield
Multi-step reaction with 2 steps 1: ammonia / 190 °C 2: alcohol; nitrous acid / man kocht den erhaltenen Niederschlag mit Wasser View Scheme
With alkaline earth hydroxide

2-sulfo-anthraquinone (84-48-0) → 2-hydroxy-9,10-anthraquinone (605-32-3) + 1,2-dihydroxy-9,10-anthracenedione (72-48-0)

Conditions	Yield
With potassium hydroxide

2-acetoxyanthracene (16433-87-7) → 2-hydroxy-9,10-anthraquinone (605-32-3)

Conditions	Yield
With chromium(VI) oxide; acetic acid man verseift das entstandene Acetat durch Kochen mit waessr.Alkalien;

1-amino-2-hydroxy-9,10-anthracenedione (568-98-9) → 2-hydroxy-9,10-anthraquinone (605-32-3)

Conditions	Yield
With ethanol; cis-nitrous acid

2-hydroxy-anthrone (5452-86-8) → 2-hydroxy-9,10-anthraquinone (605-32-3)

Conditions	Yield
With sodium dichromate; acetic acid

2-hydroxy-9,10-dioxo-9,10-dihydro-anthracene-1-carboxylic acid (374705-59-6) → 2-hydroxy-9,10-anthraquinone (605-32-3)

Conditions	Yield
at 237℃;
beim Erhitzen auf den Schmelzpunkt;

2-(3-hydroxy-benzoyl)-benzoic acid (634602-13-4) → 2-hydroxy-9,10-anthraquinone (605-32-3) + 1-hydroxyanthraquinone (129-43-1)

Conditions	Yield
With sulfuric acid at 100℃;

sodium anthraquinone-2-sulfonate (131-08-8) → 2-hydroxy-9,10-anthraquinone (605-32-3)

Conditions	Yield
With sodium hydroxide at 160 - 165℃; unter Druck; man loest die Schmelze in Wasser, faellt siedend heiss mit Salzsaeure, filtriert und behandelt den Niederschlag mit siedender Barytloesung, um Alizarin abzuscheiden; die erkaltete Barytloesung faellt man mit Salzsaeure;

9,10-phenanthrenequinone (84-65-1) → 2-hydroxy-9,10-anthraquinone (605-32-3)

Conditions	Yield
With ammonium persulfate; sulfuric acid
With quicklime; nitric acid; sodium sulfite at 190℃; Reagens 4:Wasser;unter Druck und Behandeln des Reaktionsproduktes mit Luft;

3-Carboxyphenol (99-06-9) + benzoic acid (65-85-0) → 2-hydroxy-9,10-anthraquinone (605-32-3) + 1-hydroxyanthraquinone (129-43-1)

Conditions	Yield
With sulfuric acid at 180 - 200℃;
With sulfuric acid; water at 180 - 200℃;

2-hydroxy-9,10-anthraquinone (605-32-3) + 3-[(6-bromohexyl)oxy]-9H-xanthen-9-one (473000-09-8) → 2-({6-[(9-oxo-9H-xanthen-3-yl)oxy]hexyl}oxy)anthracene-9,10-dione

Conditions	Yield
With potassium carbonate In N,N-dimethyl-formamide at 20℃; for 24h;	96%

2-hydroxy-9,10-anthraquinone (605-32-3) → 2-hydroxyanthracene (613-14-9)

Conditions	Yield
With sodium tetrahydroborate; sodium carbonate In isopropyl alcohol for 0.333333h; Heating;	93%
With aluminium amalgam; ammoniaque In water for 1h; Heating;	76%
With phosphorus; hydrogen iodide

2-hydroxy-9,10-anthraquinone (605-32-3) + 2-Bromo-4'-phenylacetophenone (135-73-9) → 2-(2-(biphenyl-4-yl)-2-oxoethoxy)anthracene-9,10-dione

Conditions	Yield
Stage #1: 2-hydroxy-9,10-anthraquinone With potassium carbonate In N,N-dimethyl-formamide at 20℃; for 0.5h; Stage #2: 2-Bromo-4'-phenylacetophenone In N,N-dimethyl-formamide at 20℃; for 24h;	92%

1-bromo dodecane (112-29-8) + 2-hydroxy-9,10-anthraquinone (605-32-3) → 2-n-decyloxy-9,10-anthraquinone

Conditions	Yield
With potassium carbonate In N,N-dimethyl-formamide for 12h; Heating;	91%

2-hydroxy-9,10-anthraquinone (605-32-3) + methyl iodide (74-88-4) → 2-methoxy-9,10-anthraquinone (3274-20-2)

Conditions	Yield
With sodium hydride In tert-butyl methyl ether; N,N-dimethyl-formamide at 20℃; for 20h;	90%

2-hydroxy-9,10-anthraquinone (605-32-3) + 2-Bromo-4'-methoxyacetophenone (2632-13-5) → 2-(2-(4-methoxyphenyl)-2-oxoethoxy)anthracene-9,10-dione

Conditions	Yield
Stage #1: 2-hydroxy-9,10-anthraquinone With potassium carbonate In N,N-dimethyl-formamide at 20℃; for 0.5h; Stage #2: 2-Bromo-4'-methoxyacetophenone In N,N-dimethyl-formamide at 20℃; for 24h;	89%

2-hydroxy-9,10-anthraquinone (605-32-3) + 2-Bromo-2'-acetonaphthone (613-54-7) → 2-(2-(naphthalen-2-yl)-2-oxoethoxy)anthracene-9,10-dione

Conditions	Yield
Stage #1: 2-hydroxy-9,10-anthraquinone With potassium carbonate In N,N-dimethyl-formamide at 20℃; for 0.5h; Stage #2: 2-Bromo-2'-acetonaphthone In N,N-dimethyl-formamide at 20℃; for 24h;	89%

1-bromo-6-hexanol (4286-55-9) + 2-hydroxy-9,10-anthraquinone (605-32-3) → hydroxyhexyloxyanthraquinone

Conditions	Yield
With potassium carbonate In N,N-dimethyl-formamide at 80℃;	89%

1,4-dibromo-2-butene (6974-12-5) + 2-hydroxy-9,10-anthraquinone (605-32-3) → 3-[(E)-4-bromobut-2-enyloxy]-9,10-anthraquinone

Conditions	Yield
Stage #1: 2-hydroxy-9,10-anthraquinone With potassium carbonate at 20℃; for 0.5h; Stage #2: 1,4-dibromo-2-butene for 4h; Reflux;	88%

2-hydroxy-9,10-anthraquinone (605-32-3) + 2-(chloromethyl)-5-(benzyloxy)-1-methylpyridin-4(1H)-one (586345-73-5) → 2-[(5-benzyloxy-1,4-dihydro-1-methyl-4-oxopyridin-2-yl)methoxy]anthrequinone (586345-84-8)

Conditions	Yield
With potassium carbonate; potassium iodide In acetone Heating;	87%

2-hydroxy-9,10-anthraquinone (605-32-3) → 1,3-diiodo-2-hydroxyanthraquinone (117638-46-7)

Conditions	Yield
With iodine; sodium acetate; iodic acid In acetic acid for 0.833333h; Heating;	86%

2-hydroxy-9,10-anthraquinone (605-32-3) + 1-dodecylbromide (143-15-7) → 2-n-dodecyloxy-9,10-anthraquinone

Conditions	Yield
With potassium carbonate In N,N-dimethyl-formamide for 12h; Heating;	86%

2-hydroxy-9,10-anthraquinone (605-32-3) + α-bromoacetophenone (70-11-1) → 2-(2-oxo-2-phenylethoxy)anthracene-9,10-dione

Conditions	Yield
Stage #1: 2-hydroxy-9,10-anthraquinone With potassium carbonate In N,N-dimethyl-formamide at 20℃; for 0.5h; Stage #2: α-bromoacetophenone In N,N-dimethyl-formamide at 20℃; for 24h;	86%

1-Bromotetradecane (112-71-0) + 2-hydroxy-9,10-anthraquinone (605-32-3) → 2-n-tetradecyloxyanthraquinone (1430074-42-2)

Conditions	Yield
Stage #1: 2-hydroxy-9,10-anthraquinone With potassium carbonate In N,N-dimethyl-formamide at 20℃; Stage #2: 1-Bromotetradecane In N,N-dimethyl-formamide at 79.84℃; for 24h;	82%

2-hydroxy-9,10-anthraquinone (605-32-3) + 2-bromo-4'-fluoroacetophenone (403-29-2) → 2-(2-(4-fluorophenyl)-2-oxoethoxy)anthracene-9,10-dione

Conditions	Yield
Stage #1: 2-hydroxy-9,10-anthraquinone With potassium carbonate In N,N-dimethyl-formamide at 20℃; for 0.5h; Stage #2: 2-bromo-4'-fluoroacetophenone In N,N-dimethyl-formamide at 20℃; for 24h;	82%

pentadecyl bromide (629-72-1) + 2-hydroxy-9,10-anthraquinone (605-32-3) → 2-n-pentadecyloxyanthraquinone (1430074-43-3)

Conditions	Yield
Stage #1: 2-hydroxy-9,10-anthraquinone With potassium carbonate In N,N-dimethyl-formamide at 20℃; Stage #2: pentadecyl bromide In N,N-dimethyl-formamide at 79.84℃; for 24h;	80%

1 ,6-dibromohexane (629-03-8) + 2-hydroxy-9,10-anthraquinone (605-32-3) → 2-[(6-bromohexyl)oxy]anthracene-9,10-dione

Conditions	Yield
With potassium carbonate at 110℃; for 72h; Inert atmosphere;	79%

2-hydroxy-9,10-anthraquinone (605-32-3) → C14H7IO3

Conditions	Yield
With iodine In pyridine for 2h; Inert atmosphere;	78%

2-hydroxy-9,10-anthraquinone (605-32-3) + hexadecanyl bromide (112-82-3) → 2-n-hexadecyloxyanthraquinone

Conditions	Yield
Stage #1: 2-hydroxy-9,10-anthraquinone With potassium carbonate In N,N-dimethyl-formamide at 20℃; Stage #2: hexadecanyl bromide In N,N-dimethyl-formamide at 79.84℃; for 24h;	75%
With potassium carbonate In N,N-dimethyl-formamide for 12h; Heating;	41%

4-Nitrophthalonitrile (31643-49-9) + 2-hydroxy-9,10-anthraquinone (605-32-3) → 4-[(9,10-dioxo-9,10-dihydroanthracen-2-yl)oxy]phthalonitrile

Conditions	Yield
With sodium carbonate In dimethyl sulfoxide at 45℃; for 48h;	75%

2-hydroxy-9,10-anthraquinone (605-32-3) + 1-Bromooctadecane (112-89-0) → 2-n-octadecyloxyanthraquinone (1430074-45-5)

Conditions	Yield
Stage #1: 2-hydroxy-9,10-anthraquinone With potassium carbonate In N,N-dimethyl-formamide at 20℃; Stage #2: 1-Bromooctadecane In N,N-dimethyl-formamide at 79.84℃; for 24h;	73%

3,4-dihydro-2H-pyran (110-87-2) + 2-hydroxy-9,10-anthraquinone (605-32-3) → 2-((tetrahydro-2H-pyran-2-yl)oxy)anthraquinone

Conditions	Yield
With toluene-4-sulfonic acid In tetrahydrofuran at 20℃; for 17h;	72%

1-Bromoeicosane (4276-49-7) + 2-hydroxy-9,10-anthraquinone (605-32-3) → 2-n-icosyloxyanthraquinone (1430074-46-6)

Conditions	Yield
Stage #1: 2-hydroxy-9,10-anthraquinone With potassium carbonate In N,N-dimethyl-formamide at 20℃; Stage #2: 1-Bromoeicosane In N,N-dimethyl-formamide at 79.84℃; for 24h;	71%

Upstream product

• 131-09-9 2-chloroanthracene-9,10-dione 
• 7664-41-7 ammonia 
• 16433-87-7 2-acetoxyanthracene 
• 85-44-9 phthalic anhydride 
• 108-95-2 phenol 
• 56-23-5 tetrachloromethane 
• 100-83-4 meta-hydroxybenzaldehyde 
• 6268-18-4 2-(3-amino-benzoyl)-benzoic acid 
• 2159-38-8 2-(3'-nitrobenzoyl)benzoic acid 
• 106-41-2 4-bromo-phenol 
• 95-56-7 2-hydroxybromobenzene 
• 540-38-5 p-Iodophenol 
• 860746-46-9 2-hydroxy-1-[(2,2,2-trichloro-acetylamino)-methyl]-anthraquinone 
• 17205-33-3 2-acetoxy-3-chloro-1,4-naphthoquinone 

Downstream Products

• 81-64-1 1,4-dihydroxy-9,10-anthracenedione 
• 72-48-0 1,2-dihydroxy-9,10-anthracenedione 
• 42298-28-2 2-methoxyanthracene 
• 408337-71-3 9,10-diphenyl-anthracene-2-ol 
• 15248-70-1 2-(naphthalen-2-yl)anthracene 
• 1609021-30-8 C₂₉H₂₁F₃O₂ 
• 1609021-29-5 C₂₇H₁₉N₃O 
• 1609021-28-4 C₂₈H₂₂O₂ 
• 1609021-34-2 2-methoxy-3-(diphenylhydroxymethyl)anthracene 
• 1609021-27-3 2-hydroxy-3-(diphenylhydroxymethyl)anthracene 

Relevant articles and documents

Synthesis of bi- and tricyclic arylboronates via Cp*RuCl-catalyzed cycloaddition of α,ω-diynes with ethynylboronate

In the presence of 5-10 mol% Cp*RuCl(cod), 1,6- ana 1,7-diynes were allowed to react with an ethynylboronate at ambient temperature to give rise to bi- and tricyclic arylboronates in 64-93% isolated yields. The Royal Society of Chemistry 2005.

Design, Synthesis, Molecular Docking, and Biological Evaluation of New Emodin Anthraquinone Derivatives as Potential Antitumor Substances

The emodin anthraquinone derivatives are generally used in traditional Chinese medicine due to their various pharmacological activities. In the present study, a series of emodin anthraquinone derivatives have been designed and synthesized, among which 1,3-dihydroxy-6,8-dimethoxyanthracene-9,10-dione is a natural compound that has been synthesized for the very first time, and 1,3-dimethoxy-5,8-dimethylanthracene-9,10-dione is a compound that has never been reported earlier. Interestingly, while total seven of these compounds showed neuraminidase inhibitory activity in influenza virus with inhibition rate more than 50 %, specific four compounds exhibited significant inhibition of tumor cell proliferation. The further results demonstrate that 1,3-dimethoxy-5,8-dimethylanthracene-9,10-dione showed the best anticancer activity among all the synthesized compounds by inducing highest apoptosis rate to HCT116 cancer cells and arresting their G0/G1 cell cycle phase, through elevation of intracellular level of reactive oxygen species (ROS). Moreover, the binding of 1,3-dimethoxy-5,8-dimethylanthracene-9,10-dione with BSA protein has thoroughly been investigated. Altogether, this study suggests the neuraminidase inhibitory activity and antitumor potential of the new emodin anthraquinone derivatives.

Palladium-Catalyzed Direct Acylation: One-Pot Relay Synthesis of Anthraquinones

A bis-acylation strategy to access functionalized anthraquinones via one-pot relay process, is presented. The first acylation was feasible under [Pd]-catalyzed intermolecular direct acylation reaction, while, the second acylation was accomplished by using intramolecular Friedel-Crafts acylation. Notably, benchtop aldehydes have been utilized as non-toxic acylation agents in the key [Pd]-catalyzed acylation.