481-72-1

Basic information

• Product Name: Aloe emodin
• Synonyms: 3-HydroxyMethylchrysazine;1H-Indazole-3-carboxylic acid,4,5,6,7-tetrahydro-, ethyl ester;Aloe-eModol;NSC 38628;Diacerein IMpurity B;Aloe-eModine, froM RheuM palMatuM;1,8-dihydroxy-3-(hydroxymethyl)-10-anthracenedione;1,8-dihydroxy-3-hydroxymethyl-anthraquinon
• CAS NO: 481-72-1
• Molecular Formula: C₁₅H₁₀O₅
• Molecular Weight: 270.24
• EINECS: 207-571-7
• Product Categories: Intermediates & Fine Chemicals;Pharmaceuticals;Herb extract;chemical reagent;pharmaceutical intermediate;phytochemical;reference standards from Chinese medicinal herbs (TCM).;standardized herbal extract;natural product;Aloe-emodin;Anthraquinones, Hydroquinones and Quinones;Aromatics Compounds;Aromatics;Inhibitors
• Mol File: 481-72-1.mol

Chemical Properties

• Melting Point: 223-224°C
• Boiling Point: 373.35°C (rough estimate)
• Flash Point: 311.9 °C
• Appearance: orange solid
• Density: 1.3280 (rough estimate)
• Vapor Pressure: 8.9E-14mmHg at 25°C
• Refractive Index: 1.5000 (estimate)
• Storage Temp.: 2-8°C
• Solubility: Chloroform (Slightly), DMSO (Slightly), Methanol (Slightly, Heated)
• PKA: 6.30±0.20(Predicted)
• Stability: Hygroscopic
• Merck: 14,306
• BRN: 2059062
• CAS DataBase Reference: Aloe emodin(CAS DataBase Reference)
• NIST Chemistry Reference: Aloe emodin(481-72-1)
• EPA Substance Registry System: Aloe emodin(481-72-1)

Safety Data

• Hazard Codes: Xi
• Statements: 36/37/38
• Safety Statements: 26-36
• WGK Germany: 3
• RTECS: CB6712200
• F: 10
• Hazardous Substances Data: 481-72-1(Hazardous Substances Data)

Usage

Physical and Chemical Properties

Aloe emodin aloe is one the major components of the aloe essential oils. It is either presented in aloe in the free form or presented in rhubarb, senna, and aloe in the form of glycosides. The compound precipitated from toluene or ethanol is yellow-orange needles with a relative molecular mass of 270.25 and the melting point of 223~224 ℃. It can be subject to sublimation in the carbon dioxide gas stream. It is easily soluble in hot ethanol, ether, benzene, with the solution exhibiting yellow color. It is also soluble in aqueous ammonia and sulfuric acid with the solution exhibiting crimson color. The main active ingredient of aloe is the barbaloin and aloe emodin. The aloe juice has anti-inflammatory effect and can promote healing of skin damage. The above information is edited by the lookchem of Dai Xiongfeng.

Rhubarb

Rhubarb is a kind of commonly used traditional Chinese medicine. It was initially recorded in the "Shen Nong's Herbal Classic", low-grade product. It is recorded in every generations of Ancient herbal medicine. Rhubarb is the Polygonaceae plant rhubarb Rheum, Rheum tanguticum and the dried roots or rhizomes of medicinal rhubarb Rheum officinale Baill. It is mainly produced in Sichuan, Gansu, Qinghai and other places. Rhubarb has effects such as purge heating and intestine cleaning, blood cooling and detoxification effect, and blood stasis dredging and can be applied to the treatment of the internal heating and constipation, Indigestion, abdominal pain, diarrhea, heat jaundice, vomiting blood, red eyes, swollen throat, abdominal pain, appendicitis, carbuncle swollen boils, blood stasis amenorrhea, and bruises. It can also be applied to external treatment of fire burns, upper gastrointestinal bleeding and so on. We can apply it with raw use or wine-processing, wine steaming or fried carbon. Rhubarb has inhibitory effect on most Gram-positive bacteria as well as some Gram-negative bacteria in vitro. Its main active ingredient is anthraquinone derivative with the aloe emodin, emodin and rhein yielding the best efficacy. It has inhibition on the murine leukemia P388: people extracted rhein, emodin and aloe emodin from rhubarb. These three kinds of anthraquinone can all reduce the number of cancer cells and the amount of ascites in tumor mice with different extent, in which the effect of rhein is the most significant and the effect of aloe emodin is relatively poor; the effect is generally correlated with the prolonged survival period. Emodin, rhein has a strong inhibitory effect on the biosynthesis of DNA, RNA and protein while aloe emodin strong has a weak inhibitory effect. Figure 1 Rheum officinale Baill.

Chemical Properties

Orange Solid

Uses

Different sources of media describe the Uses of 481-72-1 differently. You can refer to the following data:
1. Shows significant inhibitory activity against the P-388 leukemia in mice when administered as a suspension in acetone-Tween 80. Has a specific in vitro and in vivo antineuroectodermal tumor activity. Cathartic.
2. Aloe-emodin has been used as a standard in high performance liquid chromatography (HPLC) for separation and identification of phenolic compounds in Aloe arborescens Miller var. natalensis Berger (Kidachi aloe).
3. Aloe-emodin may be used as an analytical reference standard for the determination of the analyte in plant and animal samples by high-performance liquid chromatography technique.

Definition

ChEBI: A dihydroxyanthraquinone that is chrysazin carrying a hydroxymethyl group at position 3. It has been isolated from plant species of the genus Aloe.

General Description

Diacerein is known to be a suitable drug to treat osteoarthritis and prevent vascular diseases. It is a semi-synthetic anthraquinone derivative which acts by inhibiting the production of interleukin-1 and secretion of metalloproteases.

Biochem/physiol Actions

Laxative/cathartic compound; increases the contraction of intestinal smooth muscle by releasing endogenous acetylcholine. Anti-tumor activity is associated with an increased production of reactive oxygen species (ROS) that, in turn, reduces the mitochondrial transmembrane electrical potential, thus inducing a permeability transition that sets in motion a series of events culminating in cellular apoptosis. Genotoxicity and mutagenicity appear to be due to the inhibition of topoisomerase II activity by aloe emodin.

InChI:InChI=1/C15H10O5/c16-6-7-4-9-13(11(18)5-7)15(20)12-8(14(9)19)2-1-3-10(12)17/h1-5,16-18H,6H2

Synthetic route

(1,8-dihydroxy-9,10-dioxo-9,10-dihydroanthracen-3-yl)methyl acetate (65615-58-9) → 1,8-dihydroxy-3-hydroxymethyl-9,10-anthracenedione (481-72-1)

Conditions	Yield
With potassium hydroxide In ethanol for 0.166667h; Heating;	100%
With sodium hydroxide for 24h; Ambient temperature;	94%

Aloe-emodin 1-O-beta-D-glucopyranoside → 1,8-dihydroxy-3-hydroxymethyl-9,10-anthracenedione (481-72-1)

Conditions	Yield
With acetate buffer; β-glucosidase In water at 37℃; for 16h; pH=5.0;	95%
Enzymatic reaction;

aloin (452311-56-7) → 1,8-dihydroxy-3-hydroxymethyl-9,10-anthracenedione (481-72-1)

Conditions	Yield
Stage #1: aloin With hydrogenchloride In water at 20 - 80℃; for 1.41667h; Stage #2: With oxygen; copper(l) chloride In water at 90℃; for 7h; Product distribution / selectivity;	92%
With oxygen; nitric acid In ethylene glycol at 120℃; for 6.33333h; Product distribution / selectivity;	75%
With oxygen; nitric acid In ethylene glycol at 120℃; for 0.333333 - 6.33333h; Conversion of starting material;
With oxygen; nitric acid In ethylene glycol at 105℃; under 1125.11 Torr; for 5.25h; Product distribution / selectivity;

citreorosein (481-73-2) → 1,8-dihydroxy-3-hydroxymethyl-9,10-anthracenedione (481-72-1) + (R)-3,8,9,10-tetrahydroxy-6-(hydroxymethyl)-3,4-dihydroanthracen-1(2H)-one

Conditions	Yield
With glucose dehydrogenase; sodium dithionite; β-D-glucose; Talaromyces islandicus anthrol reductase; nicotinamide adenine dinucleotide phosphate In aq. phosphate buffer; dimethyl sulfoxide for 14h; pH=7; Inert atmosphere; Enzymatic reaction; stereoselective reaction;	A 10% B 79%
With glucose dehydrogenase; sodium dithionite; β-D-glucose; polyhydroxyanthracene reductase from Cochliobolus lunatus; NADPH In aq. phosphate buffer; dimethyl sulfoxide for 24h; Solvent; Inert atmosphere; Enzymatic reaction;	A 8% B 74%

(10S)-1,8-dihydroxy-3-(hydroxymethyl)-10-[(2S,3R,4R,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]-10H-anthracen-9-one (1415-73-2, 28371-16-6, 73649-93-1) → 1,8-dihydroxy-3-hydroxymethyl-9,10-anthracenedione (481-72-1)

Conditions	Yield
With iron(III) chloride In water	74%

Chrysophanol (481-74-3) → 1,8-dihydroxy-3-hydroxymethyl-9,10-anthracenedione (481-72-1)

Conditions	Yield
Stage #1: Chrysophanol With N-Bromosuccinimide; dibenzoyl peroxide In tetrachloromethane for 6h; Heating; Stage #2: With water; calcium carbonate In 1,4-dioxane at 120℃; for 7h;	71%
Multi-step reaction with 2 steps 1: NBS; (PhCO2)2 / CCl4 / 6 h / Heating 2: 756 mg / H2O; CaCO3 / dioxane / 7 h / 120 °C View Scheme

Rhein methyl ester (6155-37-9) → 1,8-dihydroxy-3-hydroxymethyl-9,10-anthracenedione (481-72-1)

Conditions	Yield
With lithium aluminium tetrahydride In tetrahydrofuran at 0℃; for 2h; Reflux;	65%

(R)-3,8,9,10-tetrahydroxy-6-(hydroxymethyl)-3,4-dihydroanthracen-1(2H)-one → 1,8-dihydroxy-3-hydroxymethyl-9,10-anthracenedione (481-72-1) + (−)-flavoskyrin C

Conditions	Yield
With oxygen In aq. phosphate buffer; acetonitrile at 10℃; pH=6;	A 18% B 58%

(R)-3,8,9,10-tetrahydroxy-6-(hydroxymethyl)-3,4-dihydroanthracen-1(2H)-one → 1,8-dihydroxy-3-hydroxymethyl-9,10-anthracenedione (481-72-1) + (–)-flavoskyrin C

Conditions	Yield
With lead(IV) tetraacetate; acetic acid at 0 - 20℃;	A 23% B 48%

1,8-dihydroxy-3-(pivaloyloxymethyl)-9,10-antraquinone (439290-04-7) → 1,8-dihydroxy-3-hydroxymethyl-9,10-anthracenedione (481-72-1)

Conditions	Yield
With potassium tert-butylate; water In tetrahydrofuran; diethyl ether; dichloromethane at 20℃; for 12h;	39%

triacetyl aloe-emodin (25395-11-3) → 1,8-dihydroxy-3-hydroxymethyl-9,10-anthracenedione (481-72-1)

Conditions	Yield
With sulfuric acid

1,8-dihydroxy-3-(hydroxymethyl)-9(10H)-anthracenone (6247-99-0) → 1,8-dihydroxy-3-hydroxymethyl-9,10-anthracenedione (481-72-1)

Conditions	Yield
With sodium hydroxide

5-hydroxynaphtho-1,4-quinone (481-39-0) + 1,1-bis(trimethylsilyloxy)-3-trimethylsilyloxymethyl-1,3-butadiene (155787-92-1) → 1,8-dihydroxy-3-hydroxymethyl-9,10-anthracenedione (481-72-1)

Conditions	Yield
With hydrogenchloride 1.) toluene, 80-100 deg C, 12 h; 2.) MeOH, rt., 10 h; Yield given. Multistep reaction;

4-Bromo-3-carboxy-1,8-dimethoxy-9,10-anthraquinone (72049-23-1) → 1,8-dihydroxy-3-hydroxymethyl-9,10-anthracenedione (481-72-1)

Conditions	Yield
With sodium methylate In methanol at 140 - 150℃; for 6h;

water (7732-18-5) + iron(III) chloride (7705-08-0) + 10-glucopyranosyl-1,8-dihydroxy-3-(hydroxymethyl)-9(10H)-anthracenone (1415-73-2, 28371-16-6, 73649-93-1) → 1,8-dihydroxy-3-hydroxymethyl-9,10-anthracenedione (481-72-1)

sulfuric acid (7664-93-9) + water (7732-18-5) + 10-glucopyranosyl-1,8-dihydroxy-3-(hydroxymethyl)-9(10H)-anthracenone (1415-73-2, 28371-16-6, 73649-93-1) + potassium peroxo disulfate → 1,8-dihydroxy-3-hydroxymethyl-9,10-anthracenedione (481-72-1)

water (7732-18-5) + 10-glucopyranosyl-1,8-dihydroxy-3-(hydroxymethyl)-9(10H)-anthracenone (1415-73-2, 28371-16-6, 73649-93-1) + sodium peroxide → 1,8-dihydroxy-3-hydroxymethyl-9,10-anthracenedione (481-72-1)

hydrogenchloride (7647-01-0) + ethanol (64-17-5) + water (7732-18-5) + 10-glucopyranosyl-1,8-dihydroxy-3-(hydroxymethyl)-9(10H)-anthracenone (1415-73-2, 28371-16-6, 73649-93-1) → D-Arabinose (10323-20-3) + 1,8-dihydroxy-3-hydroxymethyl-9,10-anthracenedione (481-72-1)

sulfuric acid (7664-93-9) + water (7732-18-5) + 10-glucopyranosyl-1,8-dihydroxy-3-(hydroxymethyl)-9(10H)-anthracenone (1415-73-2, 28371-16-6, 73649-93-1) + potassium dichromate → 1,8-dihydroxy-3-hydroxymethyl-9,10-anthracenedione (481-72-1) + 4,5-dihydroxy-9,10-dihydro-anthracene-2-carboxylic acid

4.5-dihydroxy-9.10-dioxo-9.10-dihydro-anthracene-carbaldehyde-(2) → 1,8-dihydroxy-3-hydroxymethyl-9,10-anthracenedione (481-72-1)

Conditions	Yield
With ethanol; platinum; iron(II) chloride Hydrogenation;

barbaloin → 1,8-dihydroxy-3-hydroxymethyl-9,10-anthracenedione (481-72-1)

Conditions	Yield
With sodium peroxide; water at 80 - 85℃;
With potassium hydroxide; air man ansaeuert die Fluessigkeit mit H2SO4 und der Loesung das Aloeemodin mit Benzol entzieht; die Benzolloesung schuettelt man mit waessr.Ammoniak und faellt aus der ammoniakalischen Loesung mit Salzsaeure das Aloeemodin aus;
With hydrogenchloride bei Siedetemperatur,dann bei Zimmertemperatur;

isobarbaloin → 1,8-dihydroxy-3-hydroxymethyl-9,10-anthracenedione (481-72-1)

Conditions	Yield
With sodium peroxide; water at 80 - 85℃;
With hydrogenchloride bei Siedetemperatur,dann bei Zimmertemperatur;
With sodium peroxide; water bei Siedetemperatur,dann bei Zimmertemperatur;

ethanol (64-17-5) + 4,5-dihydroxy-9,10-dioxo-9,10-dihydroanthracene-2-carbaldehyde (154658-30-7) + platinum + FeCl2 → 1,8-dihydroxy-3-hydroxymethyl-9,10-anthracenedione (481-72-1)

Conditions	Yield
Hydrogenation;

1,8-dihydroxy-3-(hydroxymethyl)-9(10H)-anthracenone (6247-99-0) + aqueous KOH → 1,8-dihydroxy-3-hydroxymethyl-9,10-anthracenedione (481-72-1)

Conditions	Yield
Leiten von Luft;

2-bromomethyl-9,10-dihydro-4,5-dihydroxy-9,10-dioxoanthracene (72036-12-5) → 1,8-dihydroxy-3-hydroxymethyl-9,10-anthracenedione (481-72-1)

Conditions	Yield
With water; calcium carbonate In 1,4-dioxane at 120℃; for 7h;	756 mg
Multi-step reaction with 3 steps 1: 780 mg / H2 / 10percent Pd/C / methanol / 1 h / 3000.3 Torr 2: NBS; (PhCO2)2 / CCl4 / 6 h / Heating 3: 756 mg / H2O; CaCO3 / dioxane / 7 h / 120 °C View Scheme
Multi-step reaction with 2 steps 1: acetic acid / 0.5 h / Heating 2: 100 percent / 2percent KOH / ethanol / 0.17 h / Heating View Scheme

2,2-dimethyl-propionic acid 4-hydroxy-5-methoxy-9,10-dioxo-9,10-dihydro-anthracen-2-ylmethyl ester (439290-07-0) → 1,8-dihydroxy-3-hydroxymethyl-9,10-anthracenedione (481-72-1)

Conditions	Yield
Multi-step reaction with 2 steps 1: 84 percent / AlCl3 / CH2Cl2 / 20 °C 2: 39 percent / tBuOK; H2O / diethyl ether; CH2Cl2; tetrahydrofuran / 12 h / 20 °C View Scheme

C11H24O3Si2 → 1,8-dihydroxy-3-hydroxymethyl-9,10-anthracenedione (481-72-1)

Conditions	Yield
Multi-step reaction with 2 steps 1: BuLi/i-Pr2NH / tetrahydrofuran / - 20 deg C, 30 min, then rt., 12 h 2: 2.) 5percent HCl / 1.) toluene, 80-100 deg C, 12 h; 2.) MeOH, rt., 10 h View Scheme

1-methoxy-1,3-cyclohexadiene (2161-90-2) → 1,8-dihydroxy-3-hydroxymethyl-9,10-anthracenedione (481-72-1)

Conditions	Yield
Multi-step reaction with 3 steps 1: 95 percent / Et3N / CH2Cl2 / 24 h / Ambient temperature 2: 99 percent / AlCl3 / CH2Cl2 / 24 h / Ambient temperature 3: 94 percent / 10percent aq. NaOH / 24 h / Ambient temperature View Scheme

Ethyl 4-(acetyloxy)-6-chloro-5,8-dimethoxy-2-naphthalenecarboxylate (124010-11-3) → 1,8-dihydroxy-3-hydroxymethyl-9,10-anthracenedione (481-72-1)

Conditions

Yield

Multi-step reaction with 6 steps 1: 78 percent / LiAlH4 / tetrahydrofuran / 24 h / Ambient temperature 2: 90 percent / Et3N, DMAP / CH2Cl2 / 5 h / Ambient temperature 3: 90 percent / cerium(IV) ammonium nitrate / acetonitrile; H2O / 3 h / Ambient temperature 4: 95 percent / Et3N / CH2Cl2 / 24 h / Ambient temperature 5: 99 percent / AlCl3 / CH2Cl2 / 24 h / Ambient temperature 6: 94 percent / 10percent aq. NaOH / 24 h / Ambient temperature View Scheme

1,8-dihydroxy-3-hydroxymethyl-9,10-anthracenedione (481-72-1) → 3-(chloromethyl)-1,8-dihydroxyanthracene-9,10-dione (75694-01-8)

Conditions	Yield
With thionyl chloride In dichloromethane; N,N-dimethyl-formamide for 3h; Heating;	94%
With thionyl chloride In N,N-dimethyl-formamide at 20℃;	90%
With thionyl chloride In N,N-dimethyl-formamide at 20℃; for 12h;	90%

1,8-dihydroxy-3-hydroxymethyl-9,10-anthracenedione (481-72-1) → 1,8-dihydroxy-3-carboxy-anthraquinone (478-43-3)

Conditions	Yield
With oxygen at 120℃; for 14h; Green chemistry;	93%
With sulfuric acid; sodium nitrite at 120℃; for 3h;	85%
With water; pyridinium chlorochromate In N,N-dimethyl-formamide at 20℃; for 24h;	62%

1,8-dihydroxy-3-hydroxymethyl-9,10-anthracenedione (481-72-1) + sodium methansulfinate (20277-69-4) → 1,8-dihydroxy-3-((methylsulfonyl)methyl)anthracene-9,10-dione

Conditions	Yield
With boron trifluoride diethyl etherate; acetic acid at 20℃;	90%

1,8-dihydroxy-3-hydroxymethyl-9,10-anthracenedione (481-72-1) → 2-bromomethyl-9,10-dihydro-4,5-dihydroxy-9,10-dioxoanthracene (72036-12-5)

Conditions	Yield
With HBr(aq.) In hydrogen bromide for 3h; Heating;	89%
With carbon tetrabromide; triphenylphosphine In tetrahydrofuran at 20℃; for 2h;	81.9%
With phosphorus tribromide In tetrachloromethane for 48h; Reflux;	72.1%

1,8-dihydroxy-3-hydroxymethyl-9,10-anthracenedione (481-72-1) + dimethyl sulfate (77-78-1) → 3-(hydroxymethyl)-1,8-dimethoxy-9,10-anthracenedione (50488-95-4)

Conditions	Yield
With potassium carbonate In acetone Reflux;	85%
With potassium carbonate In acetone at 60℃; for 12h;	78%
With potassium carbonate In acetone at 56℃; for 12h;	78%

2-iodo-propane (75-30-9) + 1,8-dihydroxy-3-hydroxymethyl-9,10-anthracenedione (481-72-1) → 3-hydroxymethyl-1,8-diisopropoxyanthraquinone (355022-16-1) + 3-isopropoxymethyl-1,8-diisopropoxyanthraquinone

Conditions	Yield
With caesium carbonate In acetone for 12h; Heating;	A 82% B 7%

1,8-dihydroxy-3-hydroxymethyl-9,10-anthracenedione (481-72-1) + benzoyl chloride (98-88-4) → 1,8-bis-benzoyloxy-3-benzoyloxymethyl-anthraquinone (69232-86-6)

Conditions	Yield
With potassium carbonate In acetone at 60℃; for 24h;	78%
With pyridine

1,8-dihydroxy-3-hydroxymethyl-9,10-anthracenedione (481-72-1) + acetic anhydride (108-24-7) → triacetyl aloe-emodin (25395-11-3)

Conditions	Yield
With pyridine at 50℃; for 24h;	76%
With sodium acetate

1,8-dihydroxy-3-hydroxymethyl-9,10-anthracenedione (481-72-1) + benzyl chloride (100-44-7) → 1,8-dibenzyloxy-3-(hydroxymethyl)anthraquinone (1204745-87-8)

Conditions	Yield
Stage #1: 1,8-dihydroxy-3-hydroxymethyl-9,10-anthracenedione With potassium carbonate; tetrabutylammomium bromide; potassium iodide In N,N-dimethyl-formamide at 80℃; for 1h; Stage #2: benzyl chloride In N,N-dimethyl-formamide at 50 - 80℃;	74%
Stage #1: 1,8-dihydroxy-3-hydroxymethyl-9,10-anthracenedione With potassium carbonate; tetrabutylammomium bromide; potassium iodide In N,N-dimethyl-formamide at 60 - 80℃; for 1h; Stage #2: benzyl chloride In N,N-dimethyl-formamide at 50 - 80℃; for 1.75 - 2h;

2-iodo-propane (75-30-9) + 1,8-dihydroxy-3-hydroxymethyl-9,10-anthracenedione (481-72-1) → 3-hydroxymethyl-1,8-diisopropoxyanthraquinone (355022-16-1)

Conditions	Yield
With caesium carbonate In acetone for 96h; Heating;	72%

1,8-dihydroxy-3-hydroxymethyl-9,10-anthracenedione (481-72-1) + p-toluenesulfonyl chloride (98-59-9) → C29H22O9S2 (1425440-98-7)

Conditions	Yield
With potassium carbonate In acetone at 60℃; for 6h;	70%

1,8-dihydroxy-3-hydroxymethyl-9,10-anthracenedione (481-72-1) → 4,5-dihydroxy-9,10-dioxo-9,10-dihydroanthracene-2-carbaldehyde (154658-30-7)

Conditions	Yield
With pyridinium chlorochromate In dichloromethane at 20℃; for 6h;	60%
With pyridinium chlorochromate In dichloromethane at 20℃; for 6h;	60%
With pyridinium chlorochromate In acetone for 24h; Reflux;	60.7%

1,8-dihydroxy-3-hydroxymethyl-9,10-anthracenedione (481-72-1) + methyl halide → 3-(hydroxymethyl)-1,8-dimethoxy-9,10-anthracenedione (50488-95-4)

Conditions	Yield
With potassium carbonate In N,N-dimethyl-formamide at 55℃; for 20h;	53.1%

1,8-dihydroxy-3-hydroxymethyl-9,10-anthracenedione (481-72-1) + acetic acid (64-19-7) → Chrysophanol (481-74-3) + (1,8-dihydroxy-9,10-dioxo-9,10-dihydroanthracen-3-yl)methyl acetate (65615-58-9)

Conditions	Yield
With tin(ll) chloride In hydrogenchloride at 120℃; for 1h;	A 25% B 52%

3,4,6-tri-O-acetyl-2-deoxy-2-trifluoroacetamido-α-D-glucospyranosyl bromide (6736-63-6) + 1,8-dihydroxy-3-hydroxymethyl-9,10-anthracenedione (481-72-1) → 2-<<3,4,6-tri-O-acetyl-2-deoxy-2-<(trifluoroacetyl)amino>-β-D-glucosyloxy>methyl>-9,10-dihydro-9,10-anthracenedione (102830-97-7)

Conditions	Yield
With 3 A molecular sieve; silver trifluoromethanesulfonate In dichloromethane for 4h; Ambient temperature;	49%

1-bromo-hexane (111-25-1) + 1,8-dihydroxy-3-hydroxymethyl-9,10-anthracenedione (481-72-1) → 1,8-di-O-hexylaloe-emodin (1041365-92-7)

Conditions	Yield
With potassium carbonate In N,N-dimethyl-formamide Reflux;	49%

1-Iodododecane (4292-19-7) + 1,8-dihydroxy-3-hydroxymethyl-9,10-anthracenedione (481-72-1) → 1,8-di-O-dodecylaloe-emodin (1041365-96-1)

Conditions	Yield
With potassium carbonate In N,N-dimethyl-formamide Reflux;	40%

1,8-dihydroxy-3-hydroxymethyl-9,10-anthracenedione (481-72-1) + phenyl-4-O-benzoyl-3-deoxy-3-azido-2-deoxy-thio-β-L-xylopyranose → C27H21N3O8

Conditions	Yield
With 2,6-di-tert-butyl-4-methylpyridine; silver(I) hexafluorophosphate In dichloromethane at 20℃; for 16h; Inert atmosphere; Molecular sieve;	37%

n-iodooctadecane (629-93-6) + 1,8-dihydroxy-3-hydroxymethyl-9,10-anthracenedione (481-72-1) → 1,8-di-O-octadecylalor-emodin (1041366-00-0)

Conditions	Yield
With potassium carbonate In N,N-dimethyl-formamide Reflux;	36%

Upstream product

• 25395-11-3 triacetyl aloe-emodin 
• 6247-99-0 1,8-dihydroxy-3-(hydroxymethyl)-9(10H)-anthracenone 
• 481-39-0 5-hydroxynaphtho-1,4-quinone 
• 155787-92-1 1,1-bis(trimethylsilyloxy)-3-trimethylsilyloxymethyl-1,3-butadiene 
• 65615-58-9 (1,8-dihydroxy-9,10-dioxo-9,10-dihydroanthracen-3-yl)methyl acetate 
• 72049-23-1 4-Bromo-3-carboxy-1,8-dimethoxy-9,10-anthraquinone 
• 7732-18-5 water 
• 7705-08-0 iron(III) chloride 
• 1415-73-2 10-glucopyranosyl-1,8-dihydroxy-3-(hydroxymethyl)-9(10H)-anthracenone 
• 7664-93-9 sulfuric acid 
• 7647-01-0 hydrogenchloride 
• 64-17-5 ethanol 
• 154658-30-7 4,5-dihydroxy-9,10-dioxo-9,10-dihydroanthracene-2-carbaldehyde 
• 481-74-3 Chrysophanol 

Downstream Products

• 25395-11-3 triacetyl aloe-emodin 
• 613-12-7 2-methylanthracene 
• 478-43-3 1,8-dihydroxy-3-carboxy-anthraquinone 
• 491-58-7 1,8-dihydroxy-3-methylanthracen-9(10H)-one 
• 481-74-3 Chrysophanol 
• 65615-58-9 (1,8-dihydroxy-9,10-dioxo-9,10-dihydroanthracen-3-yl)methyl acetate 
• 1204745-87-8 1,8-dibenzyloxy-3-(hydroxymethyl)anthraquinone 
• 1425440-98-7 C₂₉H₂₂O₉S₂ 
• 1425441-33-3 C₂₉H₂₁ClO₈S₂ 
• 1425441-06-0 (E)-1,8-dimethoxy-3-((phenylimino)methyl)anthracene-9,10-dione 
• 1425441-21-9 N-((4,5-dihydroxy-9,10-dioxo-9,10-dihydroanthracen-2-yl)methyl)-N,N-dimethylbenzenaminium chloride 
• 1425441-27-5 N-((4,5-dimethoxy-9,10-dioxo-9,10-dihydroanthracen-2-yl)methyl)-N,N-dimethylbenzenaminium chloride 
• 13739-02-1 diacetylrhein 
• 50488-89-6 aloe-emodin 3-O-β-D-glucoside 

Relevant articles and documents

An efficient total synthesis of chrysophanol and the sennoside C aglycon

A rapid synthetic approach to the naturally occurring chrysophanol and the sennoside C aglycon is reported. The method involves a three-step protocol starting with commercially available aloin-A to give the two title compounds.

An expedient and efficient synthesis of naturally occurring hydroxy substituted anthraquinones

A general method for the synthesis of naturally occurring anthraquinones in high yield via Diels-Alder reaction is reported.

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.

Synthesis of (-)-Flavoskyrins by Catalyst-Free Oxidation of (R)-Configured Dihydroanthracenones in Aqueous Media and Its (Bio)synthetic Implications

A catalyst-free method for the synthesis of dimeric (-)-flavoskyrins has been developed. It involves the autoxidation of chemoenzymatically synthesized (R)-configured dihydroanthracenones in the presence of molecular oxygen in buffer of pH 6.0 followed by spontaneous [4 + 2] cycloaddition in stereocontrolled exo-anti fashion to form (-)-flavoskyrins. The method is applied to obtain several homo- A s well as heterodimerized flavoskyrins (nine examples) in 27-72% yield and implies the involvement of a similar pathway in the (bio)synthesis of modified bisanthraquinones and their analogues.

An efficient approach for the synthesis of novel methyl sulfones in acetic acid medium and evaluation of antimicrobial activity

A series of nine methyl sulphones (3a-3i) starting from the aldehydes (1a-1i) were synthesized in two consecutive steps. In the first step, preparation of allyl alcohols (2a-2i) from their corresponding aldehydes by the reaction of sodium borohydride in methanol at room temperature is reported. Finally, methyl sulphones are synthesized by condensing sodium methyl sulfinates with allyl alcohols in the presence of BF3.Et2O in acetic acid medium at room temperature for about 2-3 h. The reaction conditions are simple, yields are high (85%-95%), and the products were obtained with good purity. All the synthesized compounds were characterized by their 1H, 13C NMR, and mass spectral analysis. All the title compounds were screened for antimicrobial activity. Among the compounds tested, the compound 3f has inhibited both Gram positive and Gram negative bacteria effectively and compound 3i has shown potent antifungal activity. These promising components may help to develop more potent drugs in the near future for the treatment of bacterial and fungal infections.

Inducing apoptosis through upregulation of p53: structure–activity exploration of anthraquinone analogs

We previously reported a series of p53-elevating anthraquinone compounds with considerable cytotoxicity for acute lymphoblastic leukemia (ALL) cells. To further develop this class of compounds, we examined the effect of a few key structural features on the anticancer structure–activity relationship (SAR) in ALL cells. The active analogs showed comparable cytotoxicity and upregulation of p53 but did not induce significant downregulation of MDM2 as seen with the lead compound AQ-101, indicating the importance of the anthraquinone core scaffold for MDM2 regulation. The result from the current study not only contributes to the SAR framework of these anthraquinone derivatives but also opens up new chemical space for further optimization work.

Chemoenzymatic, biomimetic total synthesis of (-)-rugulosin B, C and rugulin analogues and their biosynthetic implications

Herein, we report the chemoenzymatic synthesis of a heterodimeric (-)-rugulosin B, homodimeric (-)-rugulosin C, and several rugulin analogues in three to four steps starting from anthraquinones. This work supports dimerization between variously substituted putative monomeric intermediates during the biosynthesis of naturally occurring (+)-rugulosin B and C.

Chemoenzymatic reduction of citreorosein and its implications on aloe-emodin and rugulosin C (bio)synthesis

A chemoenzymatic reduction of citreorosein by the NADPH-dependent polyhydroxyanthracene reductase from Cochliobolus lunatus or MdpC from Aspergillus nidulans in the presence of Na2S2O4 gave access to putative biosynthetic intermediates, (R)-3,8,9,10-tetrahydroxy-6-(hydroxymethyl)-3,4-dihydroanthracene-1(2H)-one and its oxidized form, (R)-3,4-dihydrocitreorosein. Herein, we discuss the implications of these results towards the (bio)synthesis of aloe-emodin and (+)-rugulosin C in fungi.

PROCESS FOR THE PREPARATION OF ALOE-EMODIN

Process for the preparation of aloe-emodin from aloin comprising oxidizing aloin by treatment with an oxygen containing gas, in an acid reaction medium, in the presence of a copper salt catalyst.

PROCESS FOR PREPARING ALOE-EMODIN

A process for preparing aloe-emodin from aloin by oxidizing aloin by treatment with an oxygen-containing gas in the presence of an acid. The aloe-emodin may be used for the production of rhein and diacerein by oxidizing aloe-emodin by treatment with a chromium-free oxidizing medium to obtain rhein and purifying the rhein obtained. The rhein may be acetylated to obtain diacerein.