Product Name

  • Name

    Rhein

  • EINECS 207-521-4
  • CAS No. 478-43-3
  • Article Data48
  • CAS DataBase
  • Density 1.687 g/cm3
  • Solubility <0.1 g/100 mL at 17 °C in water
  • Melting Point ≥300 °C(lit.)
  • Formula C15H8O6
  • Boiling Point 597.8 °C at 760 mmHg
  • Molecular Weight 284.225
  • Flash Point 329.4 °C
  • Transport Information
  • Appearance Yellowish brown solid
  • Safety 26-37/39
  • Risk Codes 36/37/38
  • Molecular Structure Molecular Structure of 478-43-3 (Rhein)
  • Hazard Symbols IrritantXi
  • Synonyms Monorhein;4,5-DiOH-anthraquinone-2-COOH;Chrysazin-3-carboxylic acid;Rhein (1,8-dihydroxy-3-carboxyl anthraquinone);4, 5-Dihydroxyanthraquinone-2-carboxylic acid;Rheic acid;9,10-Dihydro-4,5-dihydroxy-9,10-dioxo-2-anthracene carboxylic acid;Rhubarb Yellow;1.8-Dihydroxy-3-Carboxy anthraquinone;4-10-00-04088 (Beilstein Handbook Reference);2-Anthroic acid, 9,10-dihydro-4,5-dihydroxy-9,10-dioxo- (8CI);4,5-dihydroxy-9,10-dioxo-anthracene-2-carboxylate;Cassic acid;2-Anthroic acid, 9,10-dihydro-4,5-dihydroxy-9,10-dioxo-;2-Anthracenecarboxylic acid, 9,10-dihydro-4,5-dihydroxy-9,10-dioxo-;1,8-Dihydroxyanthraquinone-3-carboxylic acid;9,10-Dihydro-4,5-dihydroxy-9,10-dioxo-2-anthracenecarboxylic acid;4,5-Dihydroxy-2-anthraquinonecarboxylic acid;
  • PSA 111.90000
  • LogP 1.57140

Synthetic route

diacetylrhein
13739-02-1

diacetylrhein

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

1,8-dihydroxy-3-carboxy-anthraquinone

Conditions
ConditionsYield
With sodium carbonate In water100%
Stage #1: diacetylrhein With water; sodium carbonate
Stage #2: With hydrogenchloride In water pH=2;
100%
With sodium hydroxide In water for 0.5h;60%
Chrysophanol
481-74-3

Chrysophanol

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

1,8-dihydroxy-3-carboxy-anthraquinone

Conditions
ConditionsYield
Stage #1: Chrysophanol With chromium(VI) oxide In acetic anhydride; acetic acid at 65℃; for 8h;
Stage #2: With sodium carbonate In water
98%
Stage #1: Chrysophanol With pyridine at 20℃;
Stage #2: With chromium(VI) oxide; acetic anhydride; acetic acid In water at 45 - 65℃; for 8h;
98%
Rhein methyl ester
6155-37-9

Rhein methyl ester

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

1,8-dihydroxy-3-carboxy-anthraquinone

Conditions
ConditionsYield
With sodium hydroxide In tetrahydrofuran for 0.5h;96%
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%
4-(2-methoxybenzoyl)-5-methoxybenzene-1,3-dicarboxylic acid
1019637-61-6

4-(2-methoxybenzoyl)-5-methoxybenzene-1,3-dicarboxylic acid

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

1,8-dihydroxy-3-carboxy-anthraquinone

Conditions
ConditionsYield
at 155 - 160℃; for 14h; Inert atmosphere;92%
rhein potassium
1402610-53-0

rhein potassium

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

1,8-dihydroxy-3-carboxy-anthraquinone

Conditions
ConditionsYield
With sulfuric acid In water pH=4.5 - 5;87%
Ethyl 9,10-dihydro-4,5-dihydroxy-9,10-dioxo-2-anthracenecarboxylate
109650-18-2

Ethyl 9,10-dihydro-4,5-dihydroxy-9,10-dioxo-2-anthracenecarboxylate

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

1,8-dihydroxy-3-carboxy-anthraquinone

Conditions
ConditionsYield
With sodium hydroxide for 24h; Ambient temperature;85%
C21H21OO4N

C21H21OO4N

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

1,8-dihydroxy-3-carboxy-anthraquinone

Conditions
ConditionsYield
With hydrogenchloride at 120℃; for 120h;74%
3-carboxy-1,8-dimethoxyanthracene-9,10-dione
72049-24-2

3-carboxy-1,8-dimethoxyanthracene-9,10-dione

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

1,8-dihydroxy-3-carboxy-anthraquinone

Conditions
ConditionsYield
With hydrogen bromide In toluene for 10h; Reflux;56%
5-hydroxy-4-(2-hydroxybenzoyl)isophthalic acid
820243-51-4

5-hydroxy-4-(2-hydroxybenzoyl)isophthalic acid

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

1,8-dihydroxy-3-carboxy-anthraquinone

Conditions
ConditionsYield
With aluminium trichloride; sodium chloride at 150℃; for 2h;50%
1,8,9-triacetoxy-3-methyl-anthracene
61446-06-8

1,8,9-triacetoxy-3-methyl-anthracene

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

1,8-dihydroxy-3-carboxy-anthraquinone

sennidin B
517-44-2

sennidin B

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

1,8-dihydroxy-3-carboxy-anthraquinone

Conditions
ConditionsYield
With chromium(VI) oxide; acetic acid
(+)-4,5,4',5'-tetrahydroxy-10,10'-dioxo-9,10,9',10'-tetrahydro-[9,9']bianthryl-2,2'-dicarboxylic acid
517-44-2, 641-12-3, 57762-62-6, 67479-20-3, 98461-42-8

(+)-4,5,4',5'-tetrahydroxy-10,10'-dioxo-9,10,9',10'-tetrahydro-[9,9']bianthryl-2,2'-dicarboxylic acid

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

1,8-dihydroxy-3-carboxy-anthraquinone

Conditions
ConditionsYield
With chromium(VI) oxide; acetic acid
sennidin A-8-monoglucoside
82334-26-7, 82373-27-1, 111144-51-5

sennidin A-8-monoglucoside

A

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

1,8-dihydroxy-3-carboxy-anthraquinone

B

sennidin B
517-44-2

sennidin B

Conditions
ConditionsYield
With supernatant fluid of rat feces at 37℃; for 2h; Product distribution; anaerobic incubation;
4-Acetoxy-5,9-dimethoxy-anthracene-2-carboxylic acid ethyl ester
155500-91-7

4-Acetoxy-5,9-dimethoxy-anthracene-2-carboxylic acid ethyl ester

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

1,8-dihydroxy-3-carboxy-anthraquinone

Conditions
ConditionsYield
With chromium(VI) oxide; hydrogen bromide 1.) AcOH,; Yield given. Multistep reaction;
4,5-dimethoxy-9,10-dioxo-9,10-dihydroanthracene-2-carbaldehyde

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

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

1,8-dihydroxy-3-carboxy-anthraquinone

Conditions
ConditionsYield
With sulfuric acid; bromine 1.) H2O; Yield given; Multistep reaction;
rhein-11-O-β-D-glucoside
67565-95-1

rhein-11-O-β-D-glucoside

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

1,8-dihydroxy-3-carboxy-anthraquinone

Conditions
ConditionsYield
With sodium hydroxide In methanol; water for 1h; Hydrolysis; Heating;4 mg
(+)-4,4'-dihydroxy-5,5'-di-D-glucopyranosyloxy-10,10'-dioxo-9,10,9',10'-tetrahydro-<9,9'>bianthryl-dicarboxylic acid-(2,2')

(+)-4,4'-dihydroxy-5,5'-di-D-glucopyranosyloxy-10,10'-dioxo-9,10,9',10'-tetrahydro-<9,9'>bianthryl-dicarboxylic acid-(2,2')

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

1,8-dihydroxy-3-carboxy-anthraquinone

Conditions
ConditionsYield
With water; iron(III) chloride
aloeemodin

aloeemodin

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

1,8-dihydroxy-3-carboxy-anthraquinone

Conditions
ConditionsYield
With chromium(VI) oxide; acetic acid
barbaloin

barbaloin

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

1,8-dihydroxy-3-carboxy-anthraquinone

Conditions
ConditionsYield
With chromic acid
With chromic acid Acetylieren des Oxydationsproduktes und Auskochen des Acetylierungsproduktes mit Benzol, man verseift mit verd. Kalilauge;
chrysophanic acid diacetate

chrysophanic acid diacetate

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

1,8-dihydroxy-3-carboxy-anthraquinone

Conditions
ConditionsYield
With acetic anhydride; chromic acid; acetic acid Behandeln des entstandenen Rheindiacetats mit Kalilauge;
chrysophanic acid dibenzoate

chrysophanic acid dibenzoate

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

1,8-dihydroxy-3-carboxy-anthraquinone

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

CrO2

CrO2

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

1,8-dihydroxy-3-carboxy-anthraquinone

meso-4,4'-dihydroxy-5,5'-di-D-glucopyranosyloxy-10,10'-dioxo-9,10,9',10'-tetrahydro-<9,9'>bianthryl-dicarboxylic acid-(2,2')

meso-4,4'-dihydroxy-5,5'-di-D-glucopyranosyloxy-10,10'-dioxo-9,10,9',10'-tetrahydro-<9,9'>bianthryl-dicarboxylic acid-(2,2')

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

1,8-dihydroxy-3-carboxy-anthraquinone

Conditions
ConditionsYield
With water; iron(III) chloride
8-O-β-D-glucosyl-10-C-β-D-glucosyl rhein-9-anthrone
111545-29-0, 111614-11-0

8-O-β-D-glucosyl-10-C-β-D-glucosyl rhein-9-anthrone

A

D-Glucose
2280-44-6

D-Glucose

B

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

1,8-dihydroxy-3-carboxy-anthraquinone

C

arabinose

arabinose

Conditions
ConditionsYield
With sulfuric acid; iron(III) chloride for 0.5h; Product distribution; Heating;
8-O-β-D-gucosyl-10-hydroxy-10-β-D-gycosyl rhein-9-anthrone
111545-28-9, 111614-10-9

8-O-β-D-gucosyl-10-hydroxy-10-β-D-gycosyl rhein-9-anthrone

A

D-Glucose
2280-44-6

D-Glucose

B

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

1,8-dihydroxy-3-carboxy-anthraquinone

C

arabinose

arabinose

Conditions
ConditionsYield
With sulfuric acid; iron(III) chloride for 0.5h; Product distribution; Heating;
(2,4-dibromo-6-hydroxyphenyl)-(2-hydroxyphenyl)methanone
820243-52-5

(2,4-dibromo-6-hydroxyphenyl)-(2-hydroxyphenyl)methanone

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

1,8-dihydroxy-3-carboxy-anthraquinone

Conditions
ConditionsYield
Multi-step reaction with 5 steps
1: 87 percent / K2CO3 / dimethylformamide / 12 h / 80 °C
2: 92 percent / Et3N; (dppf)PdCl2; dppf / dimethylformamide / 18 h / 80 °C / 750.06 Torr
3: KOH / methanol / 48 h / 60 °C
4: 414 mg / H2 / Pd/C / ethanol / 12 h / 20 °C / 750.06 Torr
5: 50 percent / AlCl3; NaCl / 2 h / 150 °C
View Scheme
(2-benzyloxy-4,6-dibromophenyl)-(2-benzyloxyphenyl)methanone
820243-54-7

(2-benzyloxy-4,6-dibromophenyl)-(2-benzyloxyphenyl)methanone

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

1,8-dihydroxy-3-carboxy-anthraquinone

Conditions
ConditionsYield
Multi-step reaction with 4 steps
1: 92 percent / Et3N; (dppf)PdCl2; dppf / dimethylformamide / 18 h / 80 °C / 750.06 Torr
2: KOH / methanol / 48 h / 60 °C
3: 414 mg / H2 / Pd/C / ethanol / 12 h / 20 °C / 750.06 Torr
4: 50 percent / AlCl3; NaCl / 2 h / 150 °C
View Scheme
5-benzyloxy-4-(2-benzyloxybenzoyl)isophthalic acid dimethyl ester
820243-55-8

5-benzyloxy-4-(2-benzyloxybenzoyl)isophthalic acid dimethyl ester

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

1,8-dihydroxy-3-carboxy-anthraquinone

Conditions
ConditionsYield
Multi-step reaction with 3 steps
1: KOH / methanol / 48 h / 60 °C
2: 414 mg / H2 / Pd/C / ethanol / 12 h / 20 °C / 750.06 Torr
3: 50 percent / AlCl3; NaCl / 2 h / 150 °C
View Scheme
1,8-dihydroxy-3-carboxy-anthraquinone
478-43-3

1,8-dihydroxy-3-carboxy-anthraquinone

acetic anhydride
108-24-7

acetic anhydride

diacetylrhein
13739-02-1

diacetylrhein

Conditions
ConditionsYield
With pyridine; dmap100%
With dmap; triethylamine In acetic anhydride at 20℃; for 1h;95%
With pyridine at 120℃; for 6h;93%
1,8-dihydroxy-3-carboxy-anthraquinone
478-43-3

1,8-dihydroxy-3-carboxy-anthraquinone

2-azidoethyl derivative

2-azidoethyl derivative

C21H17N9O6

C21H17N9O6

Conditions
ConditionsYield
Stage #1: 1,8-dihydroxy-3-carboxy-anthraquinone With potassium carbonate In N,N-dimethyl-formamide at 20℃; for 0.0833333h;
Stage #2: 2-azidoethyl derivative With sodium iodide In N,N-dimethyl-formamide at 60 - 70℃;
100%
1,8-dihydroxy-3-carboxy-anthraquinone
478-43-3

1,8-dihydroxy-3-carboxy-anthraquinone

2-methoxyethyl derivative

2-methoxyethyl derivative

C24H26O9

C24H26O9

Conditions
ConditionsYield
Stage #1: 1,8-dihydroxy-3-carboxy-anthraquinone With potassium carbonate In N,N-dimethyl-formamide at 20℃; for 0.0833333h;
Stage #2: 2-methoxyethyl derivative With sodium iodide In N,N-dimethyl-formamide at 60 - 70℃;
100%
1,8-dihydroxy-3-carboxy-anthraquinone
478-43-3

1,8-dihydroxy-3-carboxy-anthraquinone

3-methoxypropyl derivative

3-methoxypropyl derivative

C27H32O9

C27H32O9

Conditions
ConditionsYield
Stage #1: 1,8-dihydroxy-3-carboxy-anthraquinone With potassium carbonate In N,N-dimethyl-formamide at 20℃; for 0.0833333h;
Stage #2: 3-methoxypropyl derivative With sodium iodide In N,N-dimethyl-formamide at 60 - 70℃;
100%
1,8-dihydroxy-3-carboxy-anthraquinone
478-43-3

1,8-dihydroxy-3-carboxy-anthraquinone

allyl derivative

allyl derivative

BW-AQ-152
1537900-61-0

BW-AQ-152

Conditions
ConditionsYield
Stage #1: 1,8-dihydroxy-3-carboxy-anthraquinone With potassium carbonate In N,N-dimethyl-formamide at 20℃; for 0.0833333h;
Stage #2: allyl derivative With sodium iodide In N,N-dimethyl-formamide at 60 - 70℃;
100%
1,8-dihydroxy-3-carboxy-anthraquinone
478-43-3

1,8-dihydroxy-3-carboxy-anthraquinone

benzyl derivative

benzyl derivative

1,8-dibenzyloxy-9,10-anthraquinone-3-carboxylic acid benzyl ester
1537900-58-5

1,8-dibenzyloxy-9,10-anthraquinone-3-carboxylic acid benzyl ester

Conditions
ConditionsYield
Stage #1: 1,8-dihydroxy-3-carboxy-anthraquinone With potassium carbonate In N,N-dimethyl-formamide at 20℃; for 0.0833333h;
Stage #2: benzyl derivative With sodium iodide In N,N-dimethyl-formamide at 60 - 70℃;
100%
1,8-dihydroxy-3-carboxy-anthraquinone
478-43-3

1,8-dihydroxy-3-carboxy-anthraquinone

ethyl derivative

ethyl derivative

4,5-Diethoxy-9,10-dihydro-9,10-dioxoanthracene-2-carboxylic acid, ethyl ester

4,5-Diethoxy-9,10-dihydro-9,10-dioxoanthracene-2-carboxylic acid, ethyl ester

Conditions
ConditionsYield
Stage #1: 1,8-dihydroxy-3-carboxy-anthraquinone With potassium carbonate In N,N-dimethyl-formamide at 20℃; for 0.0833333h;
Stage #2: ethyl derivative With sodium iodide In N,N-dimethyl-formamide at 60 - 70℃;
100%
1,8-dihydroxy-3-carboxy-anthraquinone
478-43-3

1,8-dihydroxy-3-carboxy-anthraquinone

isobutyl derivative

isobutyl derivative

C27H32O6
1537900-69-8

C27H32O6

Conditions
ConditionsYield
Stage #1: 1,8-dihydroxy-3-carboxy-anthraquinone With potassium carbonate In N,N-dimethyl-formamide at 20℃; for 0.0833333h;
Stage #2: isobutyl derivative With sodium iodide In N,N-dimethyl-formamide at 60 - 70℃;
100%
1,8-dihydroxy-3-carboxy-anthraquinone
478-43-3

1,8-dihydroxy-3-carboxy-anthraquinone

isopentyl derivative

isopentyl derivative

C30H38O6
1537900-73-4

C30H38O6

Conditions
ConditionsYield
Stage #1: 1,8-dihydroxy-3-carboxy-anthraquinone With potassium carbonate In N,N-dimethyl-formamide at 20℃; for 0.0833333h;
Stage #2: isopentyl derivative With sodium iodide In N,N-dimethyl-formamide at 60 - 70℃;
100%
1,8-dihydroxy-3-carboxy-anthraquinone
478-43-3

1,8-dihydroxy-3-carboxy-anthraquinone

methyl derivative

methyl derivative

methyl 4,5-dimethoxy-9,10-dioxo-9,10-dihydroanthracene-2-carboxylate
6211-34-3

methyl 4,5-dimethoxy-9,10-dioxo-9,10-dihydroanthracene-2-carboxylate

Conditions
ConditionsYield
Stage #1: 1,8-dihydroxy-3-carboxy-anthraquinone With potassium carbonate In N,N-dimethyl-formamide at 20℃; for 0.0833333h;
Stage #2: methyl derivative With sodium iodide In N,N-dimethyl-formamide at 60 - 70℃;
100%
1,8-dihydroxy-3-carboxy-anthraquinone
478-43-3

1,8-dihydroxy-3-carboxy-anthraquinone

propyl derivative

propyl derivative

BW-AQ-147
1537900-55-2

BW-AQ-147

Conditions
ConditionsYield
Stage #1: 1,8-dihydroxy-3-carboxy-anthraquinone With potassium carbonate In N,N-dimethyl-formamide at 20℃; for 0.0833333h;
Stage #2: propyl derivative With sodium iodide In N,N-dimethyl-formamide at 60 - 70℃;
100%
1,8-dihydroxy-3-carboxy-anthraquinone
478-43-3

1,8-dihydroxy-3-carboxy-anthraquinone

methyl iodide
74-88-4

methyl iodide

Rhein methyl ester
6155-37-9

Rhein methyl ester

Conditions
ConditionsYield
With sodium hydrogencarbonate In N,N-dimethyl-formamide at 80℃;93%
With sodium hydrogencarbonate In N,N-dimethyl-formamide at 20℃;84%
1,8-dihydroxy-3-carboxy-anthraquinone
478-43-3

1,8-dihydroxy-3-carboxy-anthraquinone

ethylene glycol
107-21-1

ethylene glycol

2-hydroxyethyl 4,5-dihydroxy-9,10-dioxo-9,10-dihydroanthracene-2-carboxylate
1174523-49-9

2-hydroxyethyl 4,5-dihydroxy-9,10-dioxo-9,10-dihydroanthracene-2-carboxylate

Conditions
ConditionsYield
With sulfuric acid at 85℃; for 1h;92%
With sulfuric acid In toluene at 85℃; for 5h;72%
With sulfuric acid at 80 - 90℃;
1,8-dihydroxy-3-carboxy-anthraquinone
478-43-3

1,8-dihydroxy-3-carboxy-anthraquinone

benzyl chloride
100-44-7

benzyl chloride

1,8-dibenzyloxy-9,10-anthraquinone-3-carboxylic acid benzyl ester
1537900-58-5

1,8-dibenzyloxy-9,10-anthraquinone-3-carboxylic acid benzyl ester

Conditions
ConditionsYield
With potassium carbonate; sodium iodide In N,N-dimethyl-formamide at 60℃; Inert atmosphere;92%
With potassium carbonate; sodium iodide In N,N-dimethyl-formamide at 60℃; Inert atmosphere;92%
With potassium carbonate; sodium iodide In N,N-dimethyl-formamide at 60℃; for 48h; Inert atmosphere;92%
1 ,6-dibromohexane
629-03-8

1 ,6-dibromohexane

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

1,8-dihydroxy-3-carboxy-anthraquinone

6-bromohexyl 4,5-dihydroxy-9,10-dioxo-9,10-dihydroanthracene-2-carboxylate

6-bromohexyl 4,5-dihydroxy-9,10-dioxo-9,10-dihydroanthracene-2-carboxylate

Conditions
ConditionsYield
With tetrabutylammomium bromide; triethylamine In tetrahydrofuran at 20℃;91.6%
With tetrabutylammomium bromide; triethylamine In tetrahydrofuran at 20℃; for 18h;90.6%
With tetrabutylammomium bromide; triethylamine In tetrahydrofuran at 20℃; for 18h;89.8%
1,8-dihydroxy-3-carboxy-anthraquinone
478-43-3

1,8-dihydroxy-3-carboxy-anthraquinone

α-O,O'-diethyl amino(2-methoxyphenyl)methylphosphonate

α-O,O'-diethyl amino(2-methoxyphenyl)methylphosphonate

O,O'-diethyl {[2-(4,5-dihydroxy-9,10-dioxo-9,10-dihydroanthracen-2-yl)acetylamino](2-methoxyphenyl)methyl}phosphonate
1537944-47-0

O,O'-diethyl {[2-(4,5-dihydroxy-9,10-dioxo-9,10-dihydroanthracen-2-yl)acetylamino](2-methoxyphenyl)methyl}phosphonate

Conditions
ConditionsYield
Stage #1: 1,8-dihydroxy-3-carboxy-anthraquinone With benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride In dimethyl sulfoxide at 0℃; for 0.25h;
Stage #2: α-O,O'-diethyl amino(2-methoxyphenyl)methylphosphonate In dimethyl sulfoxide at 0 - 20℃; for 5h;
90%
Stage #1: 1,8-dihydroxy-3-carboxy-anthraquinone With benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride In methanol at 20℃; for 0.166667h; Cooling with ice;
Stage #2: α-O,O'-diethyl amino(2-methoxyphenyl)methylphosphonate In methanol; N,N-dimethyl-formamide at 35℃; for 4h;
90%
1,5-dibromo-pentane
111-24-0

1,5-dibromo-pentane

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

1,8-dihydroxy-3-carboxy-anthraquinone

5-bromopentyl 4,5-dihydroxy-9,10-dioxo-9,10-dihydroanthracene-2-carboxylate

5-bromopentyl 4,5-dihydroxy-9,10-dioxo-9,10-dihydroanthracene-2-carboxylate

Conditions
ConditionsYield
With tetrabutylammomium bromide; triethylamine In tetrahydrofuran at 20℃;89.8%
1,4-dibromo-butane
110-52-1

1,4-dibromo-butane

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

1,8-dihydroxy-3-carboxy-anthraquinone

4-bromobutyl 4,5-dihydroxy-9,10-dioxo-9,10-dihydroanthracene-2-carboxylate

4-bromobutyl 4,5-dihydroxy-9,10-dioxo-9,10-dihydroanthracene-2-carboxylate

Conditions
ConditionsYield
With tetrabutylammomium bromide; triethylamine In tetrahydrofuran at 20℃;89.2%
With tetrabutylammomium bromide; triethylamine In tetrahydrofuran at 20℃; for 18h;89.2%
1,8-dihydroxy-3-carboxy-anthraquinone
478-43-3

1,8-dihydroxy-3-carboxy-anthraquinone

diethyl [1-amine(4-methoxyphenyl)methyl]phosphonate
110470-34-3, 110548-53-3, 110548-54-4, 112564-56-4

diethyl [1-amine(4-methoxyphenyl)methyl]phosphonate

O,O'-diethyl {[2-(4,5-dihydroxy-9,10-dioxo-9,10-dihydroanthracen-2-yl)acetylamino](4-methoxyphenyl)methyl}phosphonate
1537944-50-5

O,O'-diethyl {[2-(4,5-dihydroxy-9,10-dioxo-9,10-dihydroanthracen-2-yl)acetylamino](4-methoxyphenyl)methyl}phosphonate

Conditions
ConditionsYield
Stage #1: 1,8-dihydroxy-3-carboxy-anthraquinone With benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride In dimethyl sulfoxide at 0℃; for 0.25h;
Stage #2: diethyl [1-amine(4-methoxyphenyl)methyl]phosphonate In dimethyl sulfoxide at 0 - 20℃; for 5h;
89%
With benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride In dimethyl sulfoxide at 20 - 60℃; for 3h; Cooling with ice;89%
1,8-dihydroxy-3-carboxy-anthraquinone
478-43-3

1,8-dihydroxy-3-carboxy-anthraquinone

diethylene glycol
111-46-6

diethylene glycol

2-(2-hydroxyethoxy)ethyl 4,5-dihydroxy-9,10-dioxo-9,10-dihydroanthracene-2-carboxylate
1174523-50-2

2-(2-hydroxyethoxy)ethyl 4,5-dihydroxy-9,10-dioxo-9,10-dihydroanthracene-2-carboxylate

Conditions
ConditionsYield
With sulfuric acid at 85℃; for 1h;88%
1,8-dihydroxy-3-carboxy-anthraquinone
478-43-3

1,8-dihydroxy-3-carboxy-anthraquinone

α-O,O'-diethyl amino(3-fluorophenyl)methylphosphonate
1005517-85-0

α-O,O'-diethyl amino(3-fluorophenyl)methylphosphonate

O,O'-diethyl {[2-(4,5-dihydroxy-9,10-dioxo-9,10-dihydroanthracen-2-yl)acetylamino](3-fluorophenyl)methyl}phosphonate
1537944-53-8

O,O'-diethyl {[2-(4,5-dihydroxy-9,10-dioxo-9,10-dihydroanthracen-2-yl)acetylamino](3-fluorophenyl)methyl}phosphonate

Conditions
ConditionsYield
Stage #1: 1,8-dihydroxy-3-carboxy-anthraquinone With benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride In dimethyl sulfoxide at 0℃; for 0.25h;
Stage #2: α-O,O'-diethyl amino(3-fluorophenyl)methylphosphonate In dimethyl sulfoxide at 0 - 20℃; for 5h;
88%
With benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride In methanol; dimethyl sulfoxide at 10 - 20℃; for 5h; Cooling with ice;88%
1,8-dihydroxy-3-carboxy-anthraquinone
478-43-3

1,8-dihydroxy-3-carboxy-anthraquinone

1,3-dibromo-propane
109-64-8

1,3-dibromo-propane

3-bromopropyl 4,5-dihydroxy-9,10-dioxo-9,10-dihydroanthracene-2-carboxylate

3-bromopropyl 4,5-dihydroxy-9,10-dioxo-9,10-dihydroanthracene-2-carboxylate

Conditions
ConditionsYield
With tetrabutylammomium bromide; triethylamine In tetrahydrofuran at 20℃;87.7%
With tetrabutylammomium bromide; triethylamine In tetrahydrofuran at 20℃; for 18.08h;87.5%

Rhein Chemical Properties

IUPAC Name:4,5-dihydroxy-9,10-dioxoanthracene-2-carboxylic acid
Molecular Formula:C15H8O6
Molecular Weight:284.220420 g/mol
Melting Point:≥300 °C(lit.)
storage temp.:2-8°C
Water Solubility:<0.1 g/100 mL at 17°C
Merck:13,8260
CAS DataBase Reference:478-43-3(CAS DataBase Reference)
EPA Substance Registry System:478-43-3(EPA Substance)
Synonyms of RHUBARB YELLOW(478-43-3):
9,10-dihydro-4,5-dihydroxy-9,10-dioxo-2-anthracenecarboxylicaci;9,10-dihydro-4,5-dihydroxy-9,10-dioxo-2-anthroicaci;chrysazin-3-carboxylicacid;monorhein;rheicacid;RHUBARBEXTRACT;RHUBARB YELLOW;RHEIN
Categories of RHUBARB YELLOW(478-43-3):
Anthraquinones, Hydroquinones and Quinones;Aromatics Compounds;Improve Organism Immunity;The group of Polydatin;Aromatics;Heterocycles;Intermediates & Fine Chemicals;Pharmaceuticals;Isotope Labeled Compounds

Rhein Uses

RHUBARB YELLOW(478-43-3) is used as a pharmaceutical intermediate and  health food ingredient.

Rhein Toxicity Data With Reference

1.   

orl-mus LD50:>5 g/kg

   PHTOEH    Pharmacology and Toxicology (Copenhagen). 61 (1987),153.
2.   

ivn-mus LD50:>25 mg/kg

   PHTOEH    Pharmacology and Toxicology (Copenhagen). 61 (1987),153.

Rhein Safety Profile

Safety Information of RHUBARB YELLOW(478-43-3):
Hazard Codes:Xi 
Risk Statements:36/37/38
36/37/38:Irritating to eyes, respiratory system and skin 
Safety Statements:26-37/39
26:In case of contact with eyes, rinse immediately with plenty of water and seek medical advice
37/39:Wear suitable gloves and eye/face protection   
WGK Germany:2
RTECS:CA9516000
A poison by intravenous route. Low toxicity by ingestion. When heated to decomposition it emits acrid smoke and irritating vapors.
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