117-10-2

Usage

Uses

Used in Dye Industry:
1,8-Dihydroxyanthraquinone is used as an intermediate in the manufacture of alizarin and indanthrene dyestuffs for its ability to form insoluble lakes with calcium, barium, and lead.
Used in Lubricant Industry:
1,8-Dihydroxyanthraquinone is used as an antioxidant in synthetic lubricants to improve their performance and extend their lifespan.
Used in Agricultural Industry:
1,8-Dihydroxyanthraquinone is used as a fungicide to protect crops from fungal infections.
Used in Pharmaceutical Industry:
1,8-Dihydroxyanthraquinone is used as a stimulant laxative and a cathartic, although its use is limited due to its carcinogenic properties.
Used in Chemical Synthesis:
1,8-Dihydroxyanthraquinone is used as a starting material in the synthesis of 1,4,5,8-tetramethoxyanthracene.
Used in Analytical Chemistry:
1,8-Dihydroxyanthraquinone can be used to prepare an inclusion complex with β-cyclodextrin, applicable as a sensor in the estimation of Cu2+ ions in an aqueous solution.
Used in Material Science:
1,8-Dihydroxyanthraquinone acts as an aromatic scavenger in the modification of lignin, which serves as a corrosion inhibitor for steel.
General Description:
1,8-Dihydroxyanthraquinone is an orange crystalline powder that is almost odorless and tasteless. It is also available under various brand names such as Dorbane (3M Pharmaceuticals), Istizin (Sterling Winthrop), Doss, Normax, and Regulex-d.

World Health Organization (WHO)

Dantron, an anthroquinone derivative, has been available for over twenty years and is widely used as a laxative. The results of two chronic toxicity studies in rodents, published in 1985 and 1986, have shown that administration of high doses is associated with the development of intestinal and liver tumours.

Air & Water Reactions

Insoluble in water.

Reactivity Profile

1,8-Dihydroxyanthraquinone is incompatible with strong reducing substances such as hydrides, nitrides, alkali metals, and sulfides.

Fire Hazard

Flash point data for 1,8-Dihydroxyanthraquinone are not available; however, 1,8-Dihydroxyanthraquinone is probably combustible.

Safety Profile

Confirmed carcinogen with experimental carcinogenic data. Moderately toxic by intraperitoneal route. An eye irritant. Questionable carcinogen with experimental carcinogenic and neoplastigenic data. Human mutation data reported. A laxative. When heated to decomposition it emits acrid smoke and irritating fumes.

Potential Exposure

A potential liver carcinogen and possible narcotic, 1,8-Dihydroxyanthraquinone is no longer sold or marketed in the United States Nervous system toxin-acute effects; Respiratory toxin-acute effects other than severe or moderate irritation; Liver-acute effects; Eye irritant-mild.

Carcinogenicity

Danthron is reasonably anticipated to be a human carcinogen based on sufficient evidence of carcinogenicity from studies in experimental animals.

Environmental Fate

Danthron can cause DNA damage particularly at guanines in the 5'-GG-3', 5'-GGGG-3', 5'-GGGGG-3' sequences in the presence of Cu(II), cytochrome P450 reductase and the nicotinamide adenine dinucleotide phosphate (NADPH)-generating system. H2O2 and Cu(I) may also be involved because this DNA damage can be inhibited by catalase and bathocuproine. The further mechanism is danthron is reduced by P450 reductase and generate reactive oxygen species through the redox cycle, leading to extensive Cu(II)-mediated DNA damage. The DNA damage also comes from similar topoisomerase II inhibitor behavior of danthron.

Shipping

UN2811 Toxic solids, organic, n.o.s., Hazard Class: 6.1; Labels: 6.1-Poisonous materials, Technical Name Required.

Purification Methods

Crystallise Danthrone from EtOH and sublime it in a vacuum. [Beilstein 8 IV 3217.]

Toxicity evaluation

Danthron is discovered in several species of plants and insects. It has been isolated from dried leaves and stems of Xyris semifuscata harvested in Madagascar, and roots of Da Huang, a Chinese traditional herbal medicine. Danthron also appears to be biosynthesized by some insects. The presence of danthron in insects may be a way of protection from predators. Danthron can be manually synthesized by many countries. In the United States, danthron was available from 12 suppliers. If released to the atmosphere, danthron will exist in both the vapor phase and the particulate phase. Vapor phase danthron has an estimated half-life of 11 days. Particulate phase danthron can be physically removed from air by wet and dry deposition. It is expected to biodegrade with 68% degradation within 3 months. If released to water, danthron is expected to adsorb to the surface of solid particle and sediment. Biodegradation is also a major pathway processed in water. It was reported that 82% of the added danthron was degraded by fresh water within 3 days. If added to seawater, 91% of danthron was reported as degraded. Danthron may bioconcentrate in aquatic organisms, such as fish and shrimps.

Incompatibilities

Keep away from strong reducing agents, such as hydrides, nitrides, alkali metals, and sulfides.

Waste Disposal

It is inappropriate and possibly dangerous to the environment to dispose of expired or waste drugs and pharmaceuticals by flushing them down the toilet or discarding them to the trash. Household quantities of expired or waste pharmaceuticals may be mixed with wet cat litter or coffee grounds, double- bagged in plastic, discard in trash. Larger quantities shall carefully take into consideration applicable DEA, EPA, and FDA regulations. If possible return the pharmaceutical to the manufacturer for proper disposal being careful to prop- erly label and securely package the material. Alternatively, the waste pharmaceutical shall be labeled, securely packaged and transported by a state licensed medical waste contractor to dispose by burial in a licensed hazardous or toxic waste landfill or incinerator.

InChI:InChI=1/C14H8O4/c15-9-5-1-3-7-11(9)14(18)12-8(13(7)17)4-2-6-10(12)16/h1-6,15-16H

Synthetic route

1,8-diacetoxy-9,10-anthraquinone (1963-82-2) → 1,8-dihydroxy-9,10-anthracenedione (117-10-2)

Conditions	Yield
With water; trifluoroacetic acid at 65℃; for 1h;	100%

1,4-dioxo-1,2,3,4-tetrahydro-5,9,10-trihydroxyanthracene(leuco 1,4,5-trihydroxy-9,10-anthraquinone) (69043-83-0) → 1,5-dihydroxyanthraquinone (117-12-4) + 1,8-dihydroxy-9,10-anthracenedione (117-10-2)

Conditions	Yield
With pyrrolidine In toluene for 1.5h; Heating;	A 93% B n/a

1,8-bis(2-phenylselenoethoxy)anthracene-9,10-dione (1432067-68-9) → 1,8-dihydroxy-9,10-anthracenedione (117-10-2) + 1-hydroxy-8-(2-phenylselenoethoxy)anthracene-9,10-dione (1432067-84-9)

Conditions	Yield
With iron (III) perchlorate monohydrate In dichloromethane for 2h;	A n/a B 90%
With copper(II) perchlorate hexahydrate In dichloromethane for 2h;	A n/a B 70%

4-hydroxy-10-imino-5-methoxymethoxy-10H-anthracen-9-one (577975-52-1) → 1,8-dihydroxy-9,10-anthracenedione (117-10-2)

Conditions	Yield
With sulfuric acid In 1,4-dioxane; methanol at 20℃; for 96h;	86%

1,8-bis(prop-2-ynyloxy)anthracene-9,10-dione (1182282-39-8) → 1,8-dihydroxy-9,10-anthracenedione (117-10-2) + 2,10-dimethyl-6,12-dihydroanthra[1,2-b:8,7-b']difuran-6,12-dione

Conditions	Yield
With iron at 160℃; for 0.0666667h; Claisen Rearrangement; Ionic liquid;	A 16% B 73%

1-hydroxy-8-(prop-2'-ynyloxy)anthraquinone (1393091-17-2) → 1,8-dihydroxy-9,10-anthracenedione (117-10-2) + 10-hydroxy-2-methyl-6,11-dihydroanthra[1,2-b]furan-6,11-dione

Conditions	Yield
With iron at 160℃; for 0.2h; Claisen Rearrangement; Ionic liquid;	A 15% B 73%

8-Hydroxy-1,1,4-trimethoxy-1,4,4a,9a-tetrahydro-anthraquinone (84399-87-1) → 1,8-dihydroxy-9,10-anthracenedione (117-10-2)

Conditions	Yield
With sulfuric acid	67%

1,1-ethylenedioxy-6-hydroxy-1,4,4α,9aα-tetrahydro-9,10-anthraquinone (78526-20-2) → 1,8-dihydroxy-9,10-anthracenedione (117-10-2)

Conditions	Yield
With acetic acid at 100℃; for 0.333333h;	40%

3-Hydroxy-2-(2-hydroxybenzoyl)-benzoesaeure (89646-25-3) → 1,8-dihydroxy-9,10-anthracenedione (117-10-2)

Conditions	Yield
With sulfuric acid; sulfur trioxide; boric acid at 120℃; for 0.5h;	38.4%
With boron trioxide; sulfuric acid at 100℃;

1',8',10'-trihydroxy-1,8-bis(methoxymethoxy)-[2,10'-bianthracen]-9'(10'H)-one → 1,8-dihydroxy-9,10-anthracenedione (117-10-2) + 1',8',10'-trihydroxy-8-(methoxymethoxy)-[2,10'-bianthracene]-1,4,9'(10'H)-trione

Conditions	Yield
With sodium acetate; pyridinium chlorochromate In dichloromethane at 20℃; for 26h; Inert atmosphere;	A n/a B 34%

1',8',10'-trihydroxy-1,8-bis(methoxymethoxy)-[2,10'-bianthracen]-9'(10'H)-one → 1,8-dihydroxy-9,10-anthracenedione (117-10-2) + 1',8',10'-trihydroxy-[2,10'-bianthracene]-1,4,5,8,9'(10'H)-pentaone

Conditions	Yield
With chromium(VI) oxide; acetic acid In water at 20℃; for 1.5h;	A n/a B 23%

1-hydroxy-8-methoxyanthraquinone (5539-66-2) → 1,8-dihydroxy-9,10-anthracenedione (117-10-2)

Conditions	Yield
With hydrogen bromide; acetic acid

1,2-diamino-9,10-anthraquinone (1758-68-5) → 1,5-dihydroxyanthraquinone (117-12-4) + 1,8-dihydroxy-9,10-anthracenedione (117-10-2)

Conditions	Yield
With sulfuric acid; sodium nitrite at 90 - 120℃;

1,8-anthraquinonedisulphonic acid (82-48-4) → 1,8-dihydroxy-9,10-anthracenedione (117-10-2)

Conditions	Yield
With potassium carbonate
With quicklime; water at 180 - 200℃;
With calcium hydroxide; calcium chloride at 195 - 200℃; Darstellung; im Autoklaven;

1,8-dihydroxy-3-carboxy-anthraquinone (478-43-3) → 1,8-dihydroxy-9,10-anthracenedione (117-10-2)

1,8-dinitroanthraquinone (129-39-5) → 1,8-dihydroxy-9,10-anthracenedione (117-10-2)

Conditions	Yield
With potassium acetate; acetic acid at 170℃;
Multi-step reaction with 2 steps 1: water; alkali sulfite 2: quicklime; water / 180 - 200 °C View Scheme
With pyridine
With quicklime; water at 190 - 200℃;

2,4,5,7-tetraamino-1,8-dihydroxy-anthraquinone → 1,8-dihydroxy-9,10-anthracenedione (117-10-2)

Conditions	Yield
With mixture of gaseous nitrogen oxides; sulfuric acid Erwaermen das Diazoniumsulfat mit Alkohol auf 60grad;

3-Bromojuglone (52431-65-9) + 1-<(trimethylsilyl)oxy>-1-methoxy-1,3-butadiene (110362-30-6) → 1,8-dihydroxy-9,10-anthracenedione (117-10-2)

Conditions	Yield
With hydrogenchloride 1) THF, -78 deg C, 6 h, 2) -78 deg C to r.t., 2 h; Yield given. Multistep reaction;

1,8-dihydroxy-9(10H)-anthracenone (1143-38-0) → 1,8-dihydroxy-9,10-anthracenedione (117-10-2)

Conditions	Yield
With oxygen In methanol for 1.5h; Rate constant; Mechanism; different pH; half lives of decomposition;
With oxygen In ethanol at 25℃; for 240h; Mechanism; other solvent; determinations of half-lives;
With pyridinum sulfonate fluorochromate for 0.0222222h; Neat (no solvent); Microwave irradiation;

1,8-dihydroxy-9(10H)-anthracenone (1143-38-0) → 1,8-dihydroxy-9,10-anthracenedione (117-10-2) + 1,8,1',8'-tetrahydroxy-10,10'-bianthrone (31991-54-5)

Conditions	Yield
With tetraphenylporphyrine; oxygen In methanol at -10℃; for 4h; Product distribution; Irradiation; other reagents, other solvents, other temp., no irradiation; inhibition by β-carotene;	A 67 % Chromat. B 19 % Chromat.
With 4-hydroxy-TEMPO benzoate; oxygen In dimethyl sulfoxide at 20℃; Kinetics; Further Variations:; Reagents;

1,8-dihydroxy-9(10H)-anthracenone (1143-38-0) → 1,8-dihydroxy-9,10-anthracenedione (117-10-2) + 1,8,1',8'-tetrahydroxy-10,10'-bianthrone (31991-54-5) + 1,8,10-Trihydroxy-9-anthron (64817-79-4)

Conditions	Yield
With salcomine; oxygen In dichloromethane for 1h; Product distribution; Mechanism; in the dark; further complexes of transition metals, other solvents;

1,8,9,10-anthracenetetrol (59945-68-5) + 1,8-dihydroxy-9,10-anthraquinone semiquinone (121151-81-3) → 1,8-dihydroxy-9,10-anthracenedione (117-10-2)

Conditions	Yield
In isopropyl alcohol Rate constant; Equilibrium constant;

10-bromo-1,8-dihydroxy-9(10H)-anthracenone (2891-30-7) → 1,8-dihydroxy-9,10-anthracenedione (117-10-2)

Conditions	Yield
With rac-cysteine

1,8-dihydroxy-10-(1'-oxobutyl)-9(10H)-anthracenone (75464-11-8) → 1,8-dihydroxy-9,10-anthracenedione (117-10-2)

Conditions	Yield
With oxygen In methanol for 1.5h; Rate constant; Mechanism; different pH; half lives of decomposition;

(4α,4aβ,9aβ)-8-hydroxy-1,1,4-trimethoxy-1,4,4a,9a-tetrahydroanthraquinone (84399-87-1) → 1,8-dihydroxy-9,10-anthracenedione (117-10-2)

Conditions	Yield
With sulfuric acid In tetrahydrofuran Ambient temperature;	1.4 mg

1-Amino-4,5-dihydroxy-9,10-anthracenedione (78112-67-1) → 1,8-dihydroxy-9,10-anthracenedione (117-10-2)

Conditions	Yield
With sodium hydroxide; hypophosphorous acid; sodium nitrite 1.) water, dioxan, 2.) 0 deg C, 20 min; 70 deg C, 2 h; room temperature, 10 h; Multistep reaction;

(E)-1,8-dihydroxy-10-(1-oxo-3-phenyl-2-propenyl)-9(10H)-anthracenone → (E)-3-phenylacrylic acid (140-10-3) + 1,8-dihydroxy-9,10-anthracenedione (117-10-2)

Conditions	Yield
With oxygen In ethanol at 25℃; for 240h; Mechanism; other solvent; determinations of half-lives;

1,8-dihydroxy-10-(1-oxo-2-phenylethy)-9(10H)-anthracenone (151562-41-3) → phenylacetic acid (103-82-2) + 1,8-dihydroxy-9,10-anthracenedione (117-10-2)

Conditions	Yield
With oxygen In ethanol at 25℃; for 240h; Mechanism; other solvent; determinations of half-lives;

1,8-Dihydroxy-10-(1-oxo-3-phenylpropyl)-9(10H)-anthracenone (151562-48-0) → 1,8-dihydroxy-9,10-anthracenedione (117-10-2) + 3-Phenylpropionic acid (501-52-0)

Conditions	Yield
With oxygen In ethanol at 25℃; for 240h; Mechanism; other solvent; determinations of half-lives;

1,8-dihydroxy-9,10-anthracenedione (117-10-2) + propionyl chloride (79-03-8) → Propionic acid 9,10-dioxo-8-propionyloxy-9,10-dihydro-anthracen-1-yl ester

Conditions	Yield
In pyridine for 3h; Ambient temperature;	100%

1,8-dihydroxy-9,10-anthracenedione (117-10-2) + 1-Adamantanecarbonyl chloride (2094-72-6) → C36H36O6

Conditions	Yield
In pyridine for 3h; Ambient temperature;	100%

1,8-dihydroxy-9,10-anthracenedione (117-10-2) + chloromethyl methyl ether (107-30-2) → 1,8-bis(methoxymethoxy)-9,10-anthraquinone (134112-14-4)

Conditions	Yield
With N-ethyl-N,N-diisopropylamine In chloroform for 16h; Heating;	100%
With N-ethyl-N,N-diisopropylamine In chloroform; acetic acid methyl ester for 40h; Reflux;	99%

1,8-dihydroxy-9,10-anthracenedione (117-10-2) + acetyl chloride (75-36-5) → 1,8-diacetoxy-9,10-anthraquinone (1963-82-2)

Conditions	Yield
In pyridine for 3h; Ambient temperature;	100%
With pyridine	87%

1,8-dihydroxy-9,10-anthracenedione (117-10-2) + butyryl chloride (141-75-3) → Butyric acid 8-butyryloxy-9,10-dioxo-9,10-dihydro-anthracen-1-yl ester

Conditions	Yield
In pyridine for 3h; Ambient temperature;	100%

1,8-dihydroxy-9,10-anthracenedione (117-10-2) + acetic anhydride (108-24-7) → 1,8-diacetoxy-9,10-anthraquinone (1963-82-2)

Conditions	Yield
With sodium acetate Reflux;	98%
at 170℃;
With sodium acetate

1,8-dihydroxy-9,10-anthracenedione (117-10-2) + copper(II) acetate monohydrate (6046-93-1) → bis(1,8-dihydroanthraquinonato)dicopper(II) (83533-69-1)

Conditions	Yield
In ethanol mixture was boiled for 10 min, left stirring for 1 h at room temp.; ppt. was filtered, washed several times with ethanol, acetone, finally diethyl ether, dried in vac. over P2O5; elem. anal.;	98%

lead(II) nitrate + 1,8-dihydroxy-9,10-anthracenedione (117-10-2) + water (7732-18-5) → lead 1,8-dihydroxyanthraquinone monohydride

Conditions	Yield
With sodium hydroxide at 70℃; for 2h; pH=9; Reagent/catalyst; Temperature;	97.8%

diethyl sulfate (64-67-5) + 1,8-dihydroxy-9,10-anthracenedione (117-10-2) → 1,8-diethoxyanthracene-9,10-dione (16294-26-1)

Conditions	Yield
With potassium carbonate In N,N-dimethyl-formamide at 100℃; for 2h;	97%
With potassium carbonate; acetone

1,8-dihydroxy-9,10-anthracenedione (117-10-2) + propan-1-ol-3-amine (156-87-6) → 11-hydroxy-2-(2-hydroxyethyl)anthra[9,1-de][1,3]oxazin-7(2H)-one (858519-37-6)

Conditions	Yield
With pyridine; copper(I) bromide at 20 - 80℃;	97%

1,8-dihydroxy-9,10-anthracenedione (117-10-2) + methyl p-toluene sulfonate (80-48-8) → 1,8-dimethoxy-9,10-anthracenedione (6407-55-2)

Conditions	Yield
With sodium carbonate at 320℃; for 0.0833333h;	95%
With sodium carbonate In 1,2-dichloro-benzene Heating;	87%
With sodium carbonate In various solvent(s) Yield given;

1,8-dihydroxy-9,10-anthracenedione (117-10-2) + benzyl bromide (100-39-0) → 1-(benzyloxy)-8-hydroxyanthracene-9,10-dione (22516-60-5)

Conditions	Yield
With potassium carbonate In N,N-dimethyl-formamide; butanone for 15h; Reflux;	94.8%
With potassium carbonate In N,N-dimethyl-formamide; butanone for 20h; Inert atmosphere; Reflux;

1,8-dihydroxy-9,10-anthracenedione (117-10-2) + acetic anhydride (108-24-7) → 8-hydroxy-9,10-dioxo-9,10-dihydroanthracen-1-yl acetate (43101-75-3)

Conditions	Yield
With boric acid at 90℃; for 21h;	94%
With boric acid at 95℃; for 5h;	94%
With boric acid at 90℃;
With water; boric acid 1) 90 deg C, 10 h 2) room temp., 1 h; Yield given. Multistep reaction;
With boron trioxide; (2S)-N-methyl-1-phenylpropan-2-amine hydrate; sulfuric acid 1) 3 h, 110 deg C; 2) 3 h; Yield given. Multistep reaction;

1,8-dihydroxy-9,10-anthracenedione (117-10-2) + tert-butyldimethylsilyl chloride (18162-48-6) → 1,8-bis((tert-butyldimethylsilyl)oxy)-9,10-anthraquinone

Conditions	Yield
With triethylamine In dichloromethane at 0℃; for 45h; Reflux; Inert atmosphere;	94%
With 1H-imidazole In N,N-dimethyl-formamide at 25℃; for 1.25h; silylation;	73%

1,8-dihydroxy-9,10-anthracenedione (117-10-2) → 1,8-dihydroxy-9(10H)-anthracenone (1143-38-0)

Conditions	Yield
	93.7%
With hydrogenchloride; acetic acid; tin(ll) chloride In water at 60 - 65℃; for 3h;	92%
With hydrogenchloride; tin(ll) chloride In acetic acid Heating;	90%

1,8-dihydroxy-9,10-anthracenedione (117-10-2) + N-methyl-N-tert-butyldimethylsilyl-1,1,1-trifluoroacetamide (77377-52-7) → 1,8-bis((tert-butyldimethylsilyl)oxy)-9,10-anthraquinone

Conditions	Yield
With tert-butyldimethylsilyl chloride In acetonitrile at 80℃; for 0.333333h; silylation;	93%

1,8-dihydroxy-9,10-anthracenedione (117-10-2) + methyl p-toluene sulfonate (80-48-8) → 1-hydroxy-8-methoxyanthraquinone (5539-66-2)

Conditions	Yield
With sodium carbonate In various solvent(s) for 2h; Heating;	93%
With sodium carbonate In various solvent(s) at 120℃; for 2h;	81%
With sodium carbonate	75%

1,8-dihydroxy-9,10-anthracenedione (117-10-2) + dimethyl sulfate (77-78-1) → 1,8-dimethoxy-9,10-anthracenedione (6407-55-2)

Conditions	Yield
With potassium carbonate In acetone for 12h; Heating;	92%
With potassium carbonate In acetone for 24.5h; Reflux; Inert atmosphere;	90%
Stage #1: 1,8-dihydroxy-9,10-anthracenedione With potassium carbonate In acetone Reflux; Stage #2: dimethyl sulfate In acetone for 54h; Reflux;	85%

1,8-dihydroxy-9,10-anthracenedione (117-10-2) + acetylenedicarboxylic acid diethyl ester (762-21-0) → diethyl 2-(9,10-dihydro-1,8-dihydroxy-9,10-dioxo-anthracen-2-yl)fumarate (1018327-05-3)

Conditions	Yield
With triphenylphosphine In toluene for 24h; Heating;	92%

copper(II) choride dihydrate + 1,8-dihydroxy-9,10-anthracenedione (117-10-2) → C28H14CuO8*2H2O

Conditions	Yield
Stage #1: copper(II) choride dihydrate; 1,8-dihydroxy-9,10-anthracenedione In methanol at 60℃; for 1h; Stage #2: With potassium hydroxide In methanol for 4h; Reflux;	91.7%

Di-tert-butyl acetylenedicarboxylate (66086-33-7) + 1,8-dihydroxy-9,10-anthracenedione (117-10-2) → di-tert-butyl 2-(9,10-dihydro-1,8-dihydroxy-9,10-dioxo-anthracen-2-yl)fumarate (1018327-07-5)

Conditions	Yield
With triphenylphosphine In toluene for 24h; Heating;	91%

1,8-dihydroxy-9,10-anthracenedione (117-10-2) + propargyl bromide (106-96-7) → 1,8-bis(prop-2-ynyloxy)anthracene-9,10-dione (1182282-39-8)

Conditions	Yield
With potassium carbonate In N,N-dimethyl-formamide at 100℃; for 24h;	91%
With potassium carbonate In N,N-dimethyl-formamide at 20℃; for 24h;	89%
With sodium carbonate In N,N-dimethyl-formamide at 20℃;	88%

1,8-dihydroxy-9,10-anthracenedione (117-10-2) + 1-dodecylbromide (143-15-7) → C38H56O4 (1429868-49-4)

Conditions	Yield
With caesium carbonate In N,N-dimethyl-formamide; acetone for 120h; Inert atmosphere; Reflux;	91%

1,8-dihydroxy-9,10-anthracenedione (117-10-2) + allyl bromide (106-95-6) → 10-[1-(prop-2-enyl)]-1,8,10-trihydroxy-9(10H)-anthracenone + 9-[1-(prop-2-enyl)]-1,8,9-trihydroxy-10(9H)-anthracenone

Conditions	Yield
With indium; water In tetrahydrofuran; methanol at 30 - 32℃; Barbier allylation;	A 90% B 4%

1,8-dihydroxy-9,10-anthracenedione (117-10-2) + allyl bromide (106-95-6) → 10-[1-(prop-2-enyl)]-1,8,10-trihydroxy-9(10H)-anthracenone

Conditions	Yield
With indium In tetrahydrofuran; methanol; water at 29.85 - 31.85℃;	90%

1,8-dihydroxy-9,10-anthracenedione (117-10-2) + (2,4-dinitro-phenyl)-hydrazine (119-26-6) → 10-[(2,4-dinitrophenyl)hydrazono]-1,8-dihydroxy-10H-anthracen-9-one (156383-28-7)

Conditions	Yield
With sulfuric acid In methanol at 50℃; for 0.5h;	90%

1,8-dihydroxy-9,10-anthracenedione (117-10-2) + copper(II) acetate monohydrate (6046-93-1) → bis(1,8-dihydroanthraquinonato)copper(II) (109837-65-2, 109837-66-3, 58806-62-5)

Conditions	Yield
In ethanol 1,8-DHAQ was dissolved in abs. ethanol, warmed to boiling, filtered, slow addn. of ethanolic soln. of Cu(CH3COO)2*H2O, mixture was stirred at room temp. for 1 h, kept in refrigerator overnight; ppt. was washed with ethanol, acetone, finally diethyl ether, dried in vac. over P2O5; elem. anal.;	90%

1,8-dihydroxy-9,10-anthracenedione (117-10-2) → 1,8-dihydroxy-9,10-dihydroanthracene (64817-82-9)

Conditions	Yield
With lithium aluminium tetrahydride In tetrahydrofuran at 0℃; for 4.25h; Reflux;	90%
With aluminum (III) chloride; lithium aluminium tetrahydride In tetrahydrofuran Cooling with ice; Reflux;	80%
With water; sodium hydroxide; zinc
With aluminum (III) chloride; lithium aluminium tetrahydride In tetrahydrofuran Reflux;
Multi-step reaction with 2 steps 1.1: acetic acid; potassium iodide; iodine / 2 h / 80 °C / Large scale 1.2: 8.5 h / 85 - 115 °C / Large scale 2.1: sodium tetrahydroborate; trifluoroacetic acid / tert-butyl methyl ether / -15 °C / Reflux View Scheme

Upstream product

• 82-48-4 1,8-anthraquinonedisulphonic acid 
• 129-39-5 1,8-dinitroanthraquinone 
• 1963-82-2 1,8-diacetoxy-9,10-anthraquinone 
• 1143-38-0 1,8-dihydroxy-9(10H)-anthracenone 
• 59945-68-5 1,8,9,10-anthracenetetrol 
• 121151-81-3 1,8-dihydroxy-9,10-anthraquinone semiquinone 
• 78526-20-2 1,1-ethylenedioxy-6-hydroxy-1,4,4α,9aα-tetrahydro-9,10-anthraquinone 
• 129-37-3 8-nitro-9,10-dioxo-9,10-dihydro-anthracene-1-sulfonic acid 
• 7732-18-5 water 
• 567-95-3 4,5-dihydroxy-2-hydroxymethyl-1,3,6,8-tetranitro-anthraquinone 
• 64-19-7 acetic acid 
• 86911-90-2 2-(2'-Methoxybenzoyl)-6-methoxybenzoic acid 
• 80764-46-1 2-(2-methoxybenzoyl)-3-methoxybenzoic acid 
• 1182282-39-8 1,8-bis(prop-2-ynyloxy)anthracene-9,10-dione 

Downstream Products

• 16294-26-1 1,8-Diethoxyanthrachinon 
• 480-22-8 1,8,9 trihydroxyanthracene 
• 1143-38-0 1,8-dihydroxy-9(10H)-anthracenone 
• 81-55-0 1,8-dihydroxy-4,5-dinitro-anthraquinone 
• 2961-04-8 1,4,5-trihydroxy-9,10-anthracenedione 
• 51030-24-1 1,2,8-trihydroxyanthraquinone 
• 66227-51-8 1,8-dichloro-4,5-dihydroxyanthraquinone 
• 517-92-0 1,8-dihydroxy-2,4,5,7-tetranitro-anthraquinone 
• 1963-82-2 1,8-diacetoxy-9,10-anthraquinone 
• 59900-16-2 1-hydroxy-8-(tetra-O-acetyl-β-D-galactopyranosyloxy)-anthraquinone 
• 58352-80-0 Trityloxy-acetic acid 8-hydroxy-9,10-dioxo-9,10-dihydro-anthracen-1-yl ester 
• 58352-83-3 3-Trityloxy-butyric acid 8-hydroxy-9,10-dioxo-9,10-dihydro-anthracen-1-yl ester 
• 115083-92-6 5-<3-<1-(8-hydroxy-9,10-anthraquinonyl)oxy>tetramethyleneoxyphenyl>-10,15,20-triphenylporphine 
• 39003-36-6 1,8-Dihydroxy-2,5-dinitro-9,10-anthracenedione 

Related news

NotesComparison of Effects of 1,8-Dihydroxyanthraquinone (cas 117-10-2) and 1,5-Dihydroxyanthraquinone on Different Segments of Rabbit Gastrointestinal Tract08/29/2019

Using an isolated muscle bath technique, five different segments of the rabbit gastrointestinal tract (duodenum, jejunum, ileum, and ascending and descending colon) were used to record the effects of two doses of 1,5-dihydroxyanthraquinone. Transducer-recorded tracings were made of contractions ...detailed

ArticlesInclusion Complex Formation of 1,8-Dihydroxyanthraquinone (cas 117-10-2) with Cyclodextrins in Aqueous Solution and in Solid State08/28/2019

Complex formation between cyclodextrins and 1,8-dihy-droxyanthraquinone in buffer solution has been investigated using absorption, its second derivative (D2), and fluorescence spectroscopy. The results showed that whereas the self-association process was found for 1,8-dihydroxyanthraquinone alon...detailed

Raman excitation profiles of 1,8-Dihydroxyanthraquinone (cas 117-10-2) at 8 K08/27/2019

The Raman spectra and excitation profiles of solid 1,8-dihydroxyanthraquinone at 8 K have been measured. Their analysis together with the absorption and fluorescence spectra allowed us to individuate the existence of four electronic transitions in the visible region. For the two highest energy t...detailed

Characterization of the products derived from the nitration of 1,5-dihydroxyanthraquinone (anthrarufin) and 1,8-Dihydroxyanthraquinone (cas 117-10-2) (chrysazin)08/25/2019

When 1,5-dihydroxyanthraquinone (Anthrarufin) and 1,8-dihydroxyanthraquinone (Chrysazin) were nitrated using a mixture of concentrated sulfuric and nitric acids in the presence of boric acid at 10–25° C, three major products formed in each reaction. The products were separated by low-pressure ...detailed

Electron transfer reactions between 1,8-Dihydroxyanthraquinone (cas 117-10-2) and pyrimidines: A laser flash photolysis study08/23/2019

Electron transfer (ET) and hydrogen abstraction (HA) reactions between a photosensitizer, 1,8-dihydroxyanthraquinone (DHAQ), and three pyrimidines, cytosine (C), thymine (T) and uracil (U), have been investigated with a method of nanosecond time-resolved laser flash photolysis. Under photo-irrad...detailed

Relevant academic research and scientific papers

Oxygenation of Dithranol by complexes of transition elements

The oxygen activation in the dark by complexes of transition metals in the presence of the antipsoriatic compound dithranol (1a) is described.With the system CuCl/O2 an electron transfer oxygenation occurs, which simulates a 1O2-reaction, without an attack of 1O2.In the presence of Co-Salen/O2 the mechanism depends on the solvent and substrate, as already shown in the naphthalene-series.In methylenchloride dantrone (2), the radical product bisanthrone 3 and 1,8,10-trihydroxy-9-anthrone (4) are identified.The mechanistic particularity of this reaction in methylenchloride is discussed.

REGIOSPECIFIC SYNTHESIS OF QUINIZARIN DERIVATIVES BY CYCLOADDITION

Cycloaddition of (E)-1,1,4-trimethoxy-1,3-butadiene (1) to naphthoquinones affords regiospecific syntheses of derivatives of 1,4-dihydroxyanthraquinone including the mould metabolites helminthosporin (21) and cynodontin (22).

The Synthesis and Diels-Alder Reactions of 2-Prop-2-enylidene-1,3-dioxolan

The synthesis and regiospecific Diels-Alder reactions of 2-prop-2-enylidene-1,3-dioxolan (1) are described.Reactions with 1,4-naphthoquinones (5) gave tetrahydroanthraquinones (6).The adduct of (1) with juglone (5d) could be further hydrolysed to 1,8-dihydroxy-9,10-anthraquinone (7).

Total Synthesis of the Antimalarial Ascidian Natural Product Albopunctatone

The first approaches to the 10′-anthronyl-2-anthraquinone skeleton have been devised, allowing two syntheses of the marine natural product albopunctatone. Both routes involve regioselective addition of a nucleophilic masked anthraquinone to a protected chrysazin derivative; the best affords albopunctatone in five steps and 35% overall yield. Albopunctatone exhibits potent inhibitory activity against Plasmodium falciparum and negligible toxicity to a range of other microbial pathogens and mammalian cells.

The Formal Oxidative Addition of Electron-Rich Transoid Dienes to Bromonaphthoquinones

This work established the idea that a halogen atom, such as bromine, will act as a control element in the regiospecific formation of a new carbon-carbon bond.The addition of the electron-rich end of a transoid diene to a bromojuglone dervative occurred exclusively at the unsubstituted carbon of the quinone.Thus, 2,2-dimethyl-4-methoxy-6-methylene-1,3-dioxa-2-sila-4-cyclohexene (3) and either 2- or 3-bromo-5-hydroxy-1,4-naphthoquinone (1 or 2) afforded the adducts 19 or 20 in 57percent or 71percent yield.Similarly, 2,2-dimethyl-6-methylene-4-(trimethylsiloxy)-1,3-diox-4-ene (4) and 1 gave 21 in 77percent yield.

One-electron Reactions of 1,5- and 1,8-Dihydroxy-9,10-anthraquinones. A Pulse Radiolysis Study

Absorption characteristics of the semiquinone free radicals formed by one-electron reduction (using e-aq, CO2.- and CH3C.COHCH3 as the reductant) as well as the oxidation (using OH., O.- and N3. as the oxidants) of 1,5-dihydroxy-9,10-anthraquinone (1,5-DHAQ) and 1,8-dihydroxy-9,10-anthraquinone (1,8-DHAQ) have been studied by pulse radiolysis in pure isopropyl alcohol and in aqueous solutions containing various appropriate additives.The first acid dissociation constants for the reduced semiquinones were measured as pKa = 3.65 and 3.95 for 1,5-DHAQ and 1,8-DHAQ, respectively.Second-order rate constants for various formation and decay reactions have been determined.The one-electron reduction potentials (vs.NHE) were determined at pH 11, as E111 = -350 mV (for 1,5-DHAQ) and E111 = -377 mV (for 1,8-DHAQ), respectively.Differences with 1,4-dihydroxy-9,10-anthraquinone (quinizarin) are discussed.

Inhibition of the prototropic tautomerism in chrysazine by p-sulfonatocalixarene hosts

This study explores the interesting effect of p-sulfonatocalix[n]arene hosts (SCXn) on the excited-state tautomeric equilibrium of Chrysazine (CZ), a model antitumour drug molecule. Detailed photophysical investigations reveal that conversion of CZ from its more dipolar, excited normal form (N*) to the less dipolar, tautomeric form (T*) is hindered in SCXn-CZ host-guest complexes, which is quite unexpected considering the nonpolar cavity of the hosts. The atypical effect of SCXn is proposed to arise due to the partial inclusion or external binding of CZ with the hosts, which facilitates H-bonding interactions between CZ and the sulfonate groups present at the portals of the hosts. The intermolecular H-bonding subsequently leads to weakening of the pre-existing intramolecular H-bond network within CZ, and thus hinders the tautomerizaion process. Our results suggest that rather than the binding affinity, it is the orientation of CZ in the SCXn-CZ complexes, and its proximity to the portals of the host that plays a predominant role in influencing the tautomeric equilibrium. These observations are supported by quantum chemical calculations. Thermodynamic studies validate that SCXn-CZ interaction is essentially enthalpy driven and accompanied by small entropy loss, which is consistent with the binding mechanisms.

Electron Paramagnetic Resonance, ENDOR and TRIPLE Resonance of some 9,10-Anthraquinone Radicals in Solution. Part 3. - Hydroxyanthraquinones

EPR, ENDOR and TRIPLE resonance spectra have been recorded for 1,4-dihydroxy-9,10-anthraquinone, 1,5-dihydroxy-9,10-anthraquinone, 1,8-dihydroxy-9,10-anthraquinone, 2,6-dihydroxy-9,10-anthraquinone, 1,2-dihydroxy-9,10-anthraquinone, 1,2-dihydroxy-9,10-anthraquinone-3-sodium sulphonate and 1,2,5,8-tetrahydroxy-9,10-anthraquinone anion radicals.The hyperfine coupling constants and g factors ar given.Use of a modified additivity relationship allowed assignment of the constants.The spectra of deuterated radicals are discussed.

A biocatalytic approach towards the preparation of natural deoxyanthraquinones and their impact on cellular viability

Herein, a two-step chemoenzymatic process for the synthesis of medicinally important 3-deoxygenated anthra-9,10-quinones is developed. It involves a regio- and stereoselective reduction of hydroanthraquinones to (R)-configured dihydroanthracenones using an anthrol reductase of T. islandicus, followed by oxidation and dehydration to obtain deoxyanthraquinones in 65-80% yield. Comparison of the cell viability of normal human kidney HEK293 cells between anthraquinones and their deoxy derivatives revealed less toxicity for the latter.

Anthraquinones as Photoredox Catalysts for the Reductive Activation of Aryl Halides

Quinones are ubiquitous in nature as structural motifs in natural products and redox mediators in biological electron-transfer processes. Although their oxidation properties have already been used widely in chemical and photochemical reactions, the applications of quinones in reductive photoredox catalysis are less explored. We report the visible-light photoreduction of aryl halides (Ar–X; X = Cl, Br, I) by 1,8-dihydroxyanthraquinone. The resulting aryl radical anions fragment into halide anions and aryl radicals, which react through hydrogen abstraction or C–C bond-forming reactions. The active photocatalyst is generated from 1,8-dihydroxyanthraquinone by photoinduced single-electron reduction to the radical anion or subsequent protonation and further reduction (or vice versa) to the semiquinone anion. Subsequent visible-light excitation of the anthraquinone radical anion or semiquinone anion converts them into very potent single-electron donors. A plausible mechanism for the reaction is proposed on the basis of control experiments and spectroscopic investigations.