Product Name

  • Name

    Aloe emodin

  • EINECS 207-571-7
  • CAS No. 481-72-1
  • Article Data49
  • CAS DataBase
  • Density 1.592 g/cm3
  • Solubility
  • Melting Point 223-224 °C
  • Formula C15H10O5
  • Boiling Point 568.8 °C at 760 mmHg
  • Molecular Weight 270.241
  • Flash Point 311.9 °C
  • Transport Information
  • Appearance orange solid
  • Safety 26-36
  • Risk Codes 36/37/38
  • Molecular Structure Molecular Structure of 481-72-1 (Aloe emodin)
  • Hazard Symbols IrritantXi
  • Synonyms Anthraquinone,1,8-dihydroxy-3-(hydroxymethyl)- (6CI,7CI,8CI);1,8-Dihydroxy-3-hydroxymethylanthraquinone;3-Hydroxymethylchrysazin;3-Hydroxymethylchrysazine;Aloe emodin;Aloe-emodol;9,10-Anthracenedione,1,8-dihydroxy-3-(hydroxymethyl)-;Rhabarberone;Aloeemodin;Aloe-emodine;
  • PSA 94.83000
  • LogP 1.36550

Synthetic route

(1,8-dihydroxy-9,10-dioxo-9,10-dihydroanthracen-3-yl)methyl acetate
65615-58-9

(1,8-dihydroxy-9,10-dioxo-9,10-dihydroanthracen-3-yl)methyl acetate

1,8-dihydroxy-3-hydroxymethyl-9,10-anthracenedione
481-72-1

1,8-dihydroxy-3-hydroxymethyl-9,10-anthracenedione

Conditions
ConditionsYield
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

Aloe-emodin 1-O-beta-D-glucopyranoside

1,8-dihydroxy-3-hydroxymethyl-9,10-anthracenedione
481-72-1

1,8-dihydroxy-3-hydroxymethyl-9,10-anthracenedione

Conditions
ConditionsYield
With acetate buffer; β-glucosidase In water at 37℃; for 16h; pH=5.0;95%
Enzymatic reaction;
1,8-dihydroxy-3-hydroxymethyl-9,10-anthracenedione
481-72-1

1,8-dihydroxy-3-hydroxymethyl-9,10-anthracenedione

Conditions
ConditionsYield
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

citreorosein

A

1,8-dihydroxy-3-hydroxymethyl-9,10-anthracenedione
481-72-1

1,8-dihydroxy-3-hydroxymethyl-9,10-anthracenedione

B

(R)-3,8,9,10-tetrahydroxy-6-(hydroxymethyl)-3,4-dihydroanthracen-1(2H)-one

(R)-3,8,9,10-tetrahydroxy-6-(hydroxymethyl)-3,4-dihydroanthracen-1(2H)-one

Conditions
ConditionsYield
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

(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

1,8-dihydroxy-3-hydroxymethyl-9,10-anthracenedione
481-72-1

1,8-dihydroxy-3-hydroxymethyl-9,10-anthracenedione

Conditions
ConditionsYield
With iron(III) chloride In water74%
Chrysophanol
481-74-3

Chrysophanol

1,8-dihydroxy-3-hydroxymethyl-9,10-anthracenedione
481-72-1

1,8-dihydroxy-3-hydroxymethyl-9,10-anthracenedione

Conditions
ConditionsYield
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

Rhein methyl ester

1,8-dihydroxy-3-hydroxymethyl-9,10-anthracenedione
481-72-1

1,8-dihydroxy-3-hydroxymethyl-9,10-anthracenedione

Conditions
ConditionsYield
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

(R)-3,8,9,10-tetrahydroxy-6-(hydroxymethyl)-3,4-dihydroanthracen-1(2H)-one

A

1,8-dihydroxy-3-hydroxymethyl-9,10-anthracenedione
481-72-1

1,8-dihydroxy-3-hydroxymethyl-9,10-anthracenedione

B

(−)-flavoskyrin C

(−)-flavoskyrin C

Conditions
ConditionsYield
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

(R)-3,8,9,10-tetrahydroxy-6-(hydroxymethyl)-3,4-dihydroanthracen-1(2H)-one

A

1,8-dihydroxy-3-hydroxymethyl-9,10-anthracenedione
481-72-1

1,8-dihydroxy-3-hydroxymethyl-9,10-anthracenedione

B

(–)-flavoskyrin C

(–)-flavoskyrin C

Conditions
ConditionsYield
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-(pivaloyloxymethyl)-9,10-antraquinone

1,8-dihydroxy-3-hydroxymethyl-9,10-anthracenedione
481-72-1

1,8-dihydroxy-3-hydroxymethyl-9,10-anthracenedione

Conditions
ConditionsYield
With potassium tert-butylate; water In tetrahydrofuran; diethyl ether; dichloromethane at 20℃; for 12h;39%
triacetyl aloe-emodin
25395-11-3

triacetyl aloe-emodin

1,8-dihydroxy-3-hydroxymethyl-9,10-anthracenedione
481-72-1

1,8-dihydroxy-3-hydroxymethyl-9,10-anthracenedione

Conditions
ConditionsYield
With sulfuric acid
1,8-dihydroxy-3-(hydroxymethyl)-9(10H)-anthracenone
6247-99-0

1,8-dihydroxy-3-(hydroxymethyl)-9(10H)-anthracenone

1,8-dihydroxy-3-hydroxymethyl-9,10-anthracenedione
481-72-1

1,8-dihydroxy-3-hydroxymethyl-9,10-anthracenedione

Conditions
ConditionsYield
With sodium hydroxide
5-hydroxynaphtho-1,4-quinone
481-39-0

5-hydroxynaphtho-1,4-quinone

1,1-bis(trimethylsilyloxy)-3-trimethylsilyloxymethyl-1,3-butadiene
155787-92-1

1,1-bis(trimethylsilyloxy)-3-trimethylsilyloxymethyl-1,3-butadiene

1,8-dihydroxy-3-hydroxymethyl-9,10-anthracenedione
481-72-1

1,8-dihydroxy-3-hydroxymethyl-9,10-anthracenedione

Conditions
ConditionsYield
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

4-Bromo-3-carboxy-1,8-dimethoxy-9,10-anthraquinone

1,8-dihydroxy-3-hydroxymethyl-9,10-anthracenedione
481-72-1

1,8-dihydroxy-3-hydroxymethyl-9,10-anthracenedione

Conditions
ConditionsYield
With sodium methylate In methanol at 140 - 150℃; for 6h;
water
7732-18-5

water

iron(III) chloride
7705-08-0

iron(III) chloride

10-glucopyranosyl-1,8-dihydroxy-3-(hydroxymethyl)-9(10H)-anthracenone
1415-73-2, 28371-16-6, 73649-93-1

10-glucopyranosyl-1,8-dihydroxy-3-(hydroxymethyl)-9(10H)-anthracenone

1,8-dihydroxy-3-hydroxymethyl-9,10-anthracenedione
481-72-1

1,8-dihydroxy-3-hydroxymethyl-9,10-anthracenedione

sulfuric acid
7664-93-9

sulfuric acid

water
7732-18-5

water

10-glucopyranosyl-1,8-dihydroxy-3-(hydroxymethyl)-9(10H)-anthracenone
1415-73-2, 28371-16-6, 73649-93-1

10-glucopyranosyl-1,8-dihydroxy-3-(hydroxymethyl)-9(10H)-anthracenone

potassium peroxo disulfate

potassium peroxo disulfate

1,8-dihydroxy-3-hydroxymethyl-9,10-anthracenedione
481-72-1

1,8-dihydroxy-3-hydroxymethyl-9,10-anthracenedione

water
7732-18-5

water

10-glucopyranosyl-1,8-dihydroxy-3-(hydroxymethyl)-9(10H)-anthracenone
1415-73-2, 28371-16-6, 73649-93-1

10-glucopyranosyl-1,8-dihydroxy-3-(hydroxymethyl)-9(10H)-anthracenone

sodium peroxide

sodium peroxide

1,8-dihydroxy-3-hydroxymethyl-9,10-anthracenedione
481-72-1

1,8-dihydroxy-3-hydroxymethyl-9,10-anthracenedione

hydrogenchloride
7647-01-0

hydrogenchloride

ethanol
64-17-5

ethanol

water
7732-18-5

water

10-glucopyranosyl-1,8-dihydroxy-3-(hydroxymethyl)-9(10H)-anthracenone
1415-73-2, 28371-16-6, 73649-93-1

10-glucopyranosyl-1,8-dihydroxy-3-(hydroxymethyl)-9(10H)-anthracenone

A

D-Arabinose
10323-20-3

D-Arabinose

B

1,8-dihydroxy-3-hydroxymethyl-9,10-anthracenedione
481-72-1

1,8-dihydroxy-3-hydroxymethyl-9,10-anthracenedione

sulfuric acid
7664-93-9

sulfuric acid

water
7732-18-5

water

10-glucopyranosyl-1,8-dihydroxy-3-(hydroxymethyl)-9(10H)-anthracenone
1415-73-2, 28371-16-6, 73649-93-1

10-glucopyranosyl-1,8-dihydroxy-3-(hydroxymethyl)-9(10H)-anthracenone

potassium dichromate

potassium dichromate

A

1,8-dihydroxy-3-hydroxymethyl-9,10-anthracenedione
481-72-1

1,8-dihydroxy-3-hydroxymethyl-9,10-anthracenedione

B

4,5-dihydroxy-9,10-dihydro-anthracene-2-carboxylic acid

4,5-dihydroxy-9,10-dihydro-anthracene-2-carboxylic acid

4.5-dihydroxy-9.10-dioxo-9.10-dihydro-anthracene-carbaldehyde-(2)

4.5-dihydroxy-9.10-dioxo-9.10-dihydro-anthracene-carbaldehyde-(2)

1,8-dihydroxy-3-hydroxymethyl-9,10-anthracenedione
481-72-1

1,8-dihydroxy-3-hydroxymethyl-9,10-anthracenedione

Conditions
ConditionsYield
With ethanol; platinum; iron(II) chloride Hydrogenation;
barbaloin

barbaloin

1,8-dihydroxy-3-hydroxymethyl-9,10-anthracenedione
481-72-1

1,8-dihydroxy-3-hydroxymethyl-9,10-anthracenedione

Conditions
ConditionsYield
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

isobarbaloin

1,8-dihydroxy-3-hydroxymethyl-9,10-anthracenedione
481-72-1

1,8-dihydroxy-3-hydroxymethyl-9,10-anthracenedione

Conditions
ConditionsYield
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

ethanol

4,5-dihydroxy-9,10-dioxo-9,10-dihydroanthracene-2-carbaldehyde
154658-30-7

4,5-dihydroxy-9,10-dioxo-9,10-dihydroanthracene-2-carbaldehyde

platinum

platinum

FeCl2

FeCl2

1,8-dihydroxy-3-hydroxymethyl-9,10-anthracenedione
481-72-1

1,8-dihydroxy-3-hydroxymethyl-9,10-anthracenedione

Conditions
ConditionsYield
Hydrogenation;
1,8-dihydroxy-3-(hydroxymethyl)-9(10H)-anthracenone
6247-99-0

1,8-dihydroxy-3-(hydroxymethyl)-9(10H)-anthracenone

aqueous KOH

aqueous KOH

1,8-dihydroxy-3-hydroxymethyl-9,10-anthracenedione
481-72-1

1,8-dihydroxy-3-hydroxymethyl-9,10-anthracenedione

Conditions
ConditionsYield
Leiten von Luft;
2-bromomethyl-9,10-dihydro-4,5-dihydroxy-9,10-dioxoanthracene
72036-12-5

2-bromomethyl-9,10-dihydro-4,5-dihydroxy-9,10-dioxoanthracene

1,8-dihydroxy-3-hydroxymethyl-9,10-anthracenedione
481-72-1

1,8-dihydroxy-3-hydroxymethyl-9,10-anthracenedione

Conditions
ConditionsYield
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

2,2-dimethyl-propionic acid 4-hydroxy-5-methoxy-9,10-dioxo-9,10-dihydro-anthracen-2-ylmethyl ester

1,8-dihydroxy-3-hydroxymethyl-9,10-anthracenedione
481-72-1

1,8-dihydroxy-3-hydroxymethyl-9,10-anthracenedione

Conditions
ConditionsYield
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

C11H24O3Si2

1,8-dihydroxy-3-hydroxymethyl-9,10-anthracenedione
481-72-1

1,8-dihydroxy-3-hydroxymethyl-9,10-anthracenedione

Conditions
ConditionsYield
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-methoxy-1,3-cyclohexadiene

1,8-dihydroxy-3-hydroxymethyl-9,10-anthracenedione
481-72-1

1,8-dihydroxy-3-hydroxymethyl-9,10-anthracenedione

Conditions
ConditionsYield
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

Ethyl 4-(acetyloxy)-6-chloro-5,8-dimethoxy-2-naphthalenecarboxylate

1,8-dihydroxy-3-hydroxymethyl-9,10-anthracenedione
481-72-1

1,8-dihydroxy-3-hydroxymethyl-9,10-anthracenedione

Conditions
ConditionsYield
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

1,8-dihydroxy-3-hydroxymethyl-9,10-anthracenedione

3-(chloromethyl)-1,8-dihydroxyanthracene-9,10-dione
75694-01-8

3-(chloromethyl)-1,8-dihydroxyanthracene-9,10-dione

Conditions
ConditionsYield
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-hydroxymethyl-9,10-anthracenedione

1,8-dihydroxy-3-carboxy-anthraquinone
478-43-3

1,8-dihydroxy-3-carboxy-anthraquinone

Conditions
ConditionsYield
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

1,8-dihydroxy-3-hydroxymethyl-9,10-anthracenedione

sodium methansulfinate
20277-69-4

sodium methansulfinate

1,8-dihydroxy-3-((methylsulfonyl)methyl)anthracene-9,10-dione

1,8-dihydroxy-3-((methylsulfonyl)methyl)anthracene-9,10-dione

Conditions
ConditionsYield
With boron trifluoride diethyl etherate; acetic acid at 20℃;90%
1,8-dihydroxy-3-hydroxymethyl-9,10-anthracenedione
481-72-1

1,8-dihydroxy-3-hydroxymethyl-9,10-anthracenedione

2-bromomethyl-9,10-dihydro-4,5-dihydroxy-9,10-dioxoanthracene
72036-12-5

2-bromomethyl-9,10-dihydro-4,5-dihydroxy-9,10-dioxoanthracene

Conditions
ConditionsYield
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

1,8-dihydroxy-3-hydroxymethyl-9,10-anthracenedione

dimethyl sulfate
77-78-1

dimethyl sulfate

3-(hydroxymethyl)-1,8-dimethoxy-9,10-anthracenedione
50488-95-4

3-(hydroxymethyl)-1,8-dimethoxy-9,10-anthracenedione

Conditions
ConditionsYield
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

2-iodo-propane

1,8-dihydroxy-3-hydroxymethyl-9,10-anthracenedione
481-72-1

1,8-dihydroxy-3-hydroxymethyl-9,10-anthracenedione

A

3-hydroxymethyl-1,8-diisopropoxyanthraquinone
355022-16-1

3-hydroxymethyl-1,8-diisopropoxyanthraquinone

B

3-isopropoxymethyl-1,8-diisopropoxyanthraquinone

3-isopropoxymethyl-1,8-diisopropoxyanthraquinone

Conditions
ConditionsYield
With caesium carbonate In acetone for 12h; Heating;A 82%
B 7%
1,8-dihydroxy-3-hydroxymethyl-9,10-anthracenedione
481-72-1

1,8-dihydroxy-3-hydroxymethyl-9,10-anthracenedione

benzoyl chloride
98-88-4

benzoyl chloride

1,8-bis-benzoyloxy-3-benzoyloxymethyl-anthraquinone
69232-86-6

1,8-bis-benzoyloxy-3-benzoyloxymethyl-anthraquinone

Conditions
ConditionsYield
With potassium carbonate In acetone at 60℃; for 24h;78%
With pyridine
1,8-dihydroxy-3-hydroxymethyl-9,10-anthracenedione
481-72-1

1,8-dihydroxy-3-hydroxymethyl-9,10-anthracenedione

acetic anhydride
108-24-7

acetic anhydride

triacetyl aloe-emodin
25395-11-3

triacetyl aloe-emodin

Conditions
ConditionsYield
With pyridine at 50℃; for 24h;76%
With sodium acetate
1,8-dihydroxy-3-hydroxymethyl-9,10-anthracenedione
481-72-1

1,8-dihydroxy-3-hydroxymethyl-9,10-anthracenedione

benzyl chloride
100-44-7

benzyl chloride

1,8-dibenzyloxy-3-(hydroxymethyl)anthraquinone
1204745-87-8

1,8-dibenzyloxy-3-(hydroxymethyl)anthraquinone

Conditions
ConditionsYield
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

2-iodo-propane

1,8-dihydroxy-3-hydroxymethyl-9,10-anthracenedione
481-72-1

1,8-dihydroxy-3-hydroxymethyl-9,10-anthracenedione

3-hydroxymethyl-1,8-diisopropoxyanthraquinone
355022-16-1

3-hydroxymethyl-1,8-diisopropoxyanthraquinone

Conditions
ConditionsYield
With caesium carbonate In acetone for 96h; Heating;72%
1,8-dihydroxy-3-hydroxymethyl-9,10-anthracenedione
481-72-1

1,8-dihydroxy-3-hydroxymethyl-9,10-anthracenedione

p-toluenesulfonyl chloride
98-59-9

p-toluenesulfonyl chloride

C29H22O9S2
1425440-98-7

C29H22O9S2

Conditions
ConditionsYield
With potassium carbonate In acetone at 60℃; for 6h;70%
1,8-dihydroxy-3-hydroxymethyl-9,10-anthracenedione
481-72-1

1,8-dihydroxy-3-hydroxymethyl-9,10-anthracenedione

4,5-dihydroxy-9,10-dioxo-9,10-dihydroanthracene-2-carbaldehyde
154658-30-7

4,5-dihydroxy-9,10-dioxo-9,10-dihydroanthracene-2-carbaldehyde

Conditions
ConditionsYield
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

1,8-dihydroxy-3-hydroxymethyl-9,10-anthracenedione

methyl halide

methyl halide

3-(hydroxymethyl)-1,8-dimethoxy-9,10-anthracenedione
50488-95-4

3-(hydroxymethyl)-1,8-dimethoxy-9,10-anthracenedione

Conditions
ConditionsYield
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

1,8-dihydroxy-3-hydroxymethyl-9,10-anthracenedione

acetic acid
64-19-7

acetic acid

A

Chrysophanol
481-74-3

Chrysophanol

B

(1,8-dihydroxy-9,10-dioxo-9,10-dihydroanthracen-3-yl)methyl acetate
65615-58-9

(1,8-dihydroxy-9,10-dioxo-9,10-dihydroanthracen-3-yl)methyl acetate

Conditions
ConditionsYield
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

3,4,6-tri-O-acetyl-2-deoxy-2-trifluoroacetamido-α-D-glucospyranosyl bromide

1,8-dihydroxy-3-hydroxymethyl-9,10-anthracenedione
481-72-1

1,8-dihydroxy-3-hydroxymethyl-9,10-anthracenedione

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

2-<<3,4,6-tri-O-acetyl-2-deoxy-2-<(trifluoroacetyl)amino>-β-D-glucosyloxy>methyl>-9,10-dihydro-9,10-anthracenedione

Conditions
ConditionsYield
With 3 A molecular sieve; silver trifluoromethanesulfonate In dichloromethane for 4h; Ambient temperature;49%
1-bromo-hexane
111-25-1

1-bromo-hexane

1,8-dihydroxy-3-hydroxymethyl-9,10-anthracenedione
481-72-1

1,8-dihydroxy-3-hydroxymethyl-9,10-anthracenedione

1,8-di-O-hexylaloe-emodin
1041365-92-7

1,8-di-O-hexylaloe-emodin

Conditions
ConditionsYield
With potassium carbonate In N,N-dimethyl-formamide Reflux;49%
1-Iodododecane
4292-19-7

1-Iodododecane

1,8-dihydroxy-3-hydroxymethyl-9,10-anthracenedione
481-72-1

1,8-dihydroxy-3-hydroxymethyl-9,10-anthracenedione

1,8-di-O-dodecylaloe-emodin
1041365-96-1

1,8-di-O-dodecylaloe-emodin

Conditions
ConditionsYield
With potassium carbonate In N,N-dimethyl-formamide Reflux;40%
1,8-dihydroxy-3-hydroxymethyl-9,10-anthracenedione
481-72-1

1,8-dihydroxy-3-hydroxymethyl-9,10-anthracenedione

phenyl-4-O-benzoyl-3-deoxy-3-azido-2-deoxy-thio-β-L-xylopyranose

phenyl-4-O-benzoyl-3-deoxy-3-azido-2-deoxy-thio-β-L-xylopyranose

C27H21N3O8

C27H21N3O8

Conditions
ConditionsYield
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

n-iodooctadecane

1,8-dihydroxy-3-hydroxymethyl-9,10-anthracenedione
481-72-1

1,8-dihydroxy-3-hydroxymethyl-9,10-anthracenedione

1,8-di-O-octadecylalor-emodin
1041366-00-0

1,8-di-O-octadecylalor-emodin

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

Aloe-emodin Chemical Properties


IUPAC Name: 1,8-Dihydroxy-3-(hydroxymethyl)anthracene-9,10-dione
Molecular Formula: C15H10O5
Molecular Weight: 270.24 g/mol
SMILES: c12c(C(c3c(cccc3C1=O)O)=O)c(cc(c2)CO)O
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
EINECS: 207-571-7
Classification Code: Mutation data
Product Categories: Anthraquinones, Hydroquinones and Quinones; Aromatics Compounds; Aromatics; Inhibitors
Melting Point: 223-224 °C
storage temperature: 2-8 °C
Index of Refraction: 1.746 
Molar Refractivity: 68.88 cm
Molar Volume: 169.7 cm 
Surface Tension: 88.4 dyne/cm 
Density: 1.592 g/cm3 
Flash Point: 311.9 °C 
Enthalpy of Vaporization: 89.8 kJ/mol 
Boiling Point: 568.8 °C at 760 mmHg
Vapour Pressure of Aloe-emodin (CAS NO.481-72-1): 8.9E-14 mmHg at 25 °C

Aloe-emodin Uses

 Aloe-emodin (CAS NO.481-72-1) shows significant inhibitory activity against the P-388 leukemia in mice when administered as a suspension in acetone-Tween 80. It has a specific in vitro and in vivo antineuroectodermal tumor activity.

Aloe-emodin Safety Profile

Hazard Codes: IrritantXi
Risk Statements: 36/37/38 
R36/37/38:Irritating to eyes, respiratory system and skin.
Safety Statements: 26-36 
S26: In case of contact with eyes, rinse immediately with plenty of water and seek medical advice. 
S36:Wear suitable protective clothing.
WGK Germany: 3
RTECS of Aloe-emodin (CAS NO.481-72-1): CB6712200

Aloe-emodin Specification

 Aloe-emodin (CAS NO.481-72-1), its Synonyms are 1,8-Dihydroxy-3-(hydroxymethyl)-9,10-anthracenedione ; 1,8-Dihydroxy-3-hydroxymethylanthraquinone ; 3-Hydroxymethylchrysazin ; Emodine ; Rhabarberone ; 9,10-Anthracenedione, 1,8-dihydroxy-3-(hydroxymethyl)- (9CI) . It is orange solid.

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