diacetylrhein
1,8-dihydroxy-3-carboxy-anthraquinone
Conditions | Yield |
---|---|
With sodium carbonate In water | 100% |
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% |
Conditions | Yield |
---|---|
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% |
Conditions | Yield |
---|---|
With sodium hydroxide In tetrahydrofuran for 0.5h; | 96% |
1,8-dihydroxy-3-hydroxymethyl-9,10-anthracenedione
1,8-dihydroxy-3-carboxy-anthraquinone
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% |
4-(2-methoxybenzoyl)-5-methoxybenzene-1,3-dicarboxylic acid
1,8-dihydroxy-3-carboxy-anthraquinone
Conditions | Yield |
---|---|
at 155 - 160℃; for 14h; Inert atmosphere; | 92% |
rhein potassium
1,8-dihydroxy-3-carboxy-anthraquinone
Conditions | Yield |
---|---|
With sulfuric acid In water pH=4.5 - 5; | 87% |
Ethyl 9,10-dihydro-4,5-dihydroxy-9,10-dioxo-2-anthracenecarboxylate
1,8-dihydroxy-3-carboxy-anthraquinone
Conditions | Yield |
---|---|
With sodium hydroxide for 24h; Ambient temperature; | 85% |
1,8-dihydroxy-3-carboxy-anthraquinone
Conditions | Yield |
---|---|
With hydrogenchloride at 120℃; for 120h; | 74% |
3-carboxy-1,8-dimethoxyanthracene-9,10-dione
1,8-dihydroxy-3-carboxy-anthraquinone
Conditions | Yield |
---|---|
With hydrogen bromide In toluene for 10h; Reflux; | 56% |
5-hydroxy-4-(2-hydroxybenzoyl)isophthalic acid
1,8-dihydroxy-3-carboxy-anthraquinone
Conditions | Yield |
---|---|
With aluminium trichloride; sodium chloride at 150℃; for 2h; | 50% |
1,8,9-triacetoxy-3-methyl-anthracene
1,8-dihydroxy-3-carboxy-anthraquinone
Conditions | Yield |
---|---|
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
1,8-dihydroxy-3-carboxy-anthraquinone
Conditions | Yield |
---|---|
With chromium(VI) oxide; acetic acid |
sennidin A-8-monoglucoside
A
1,8-dihydroxy-3-carboxy-anthraquinone
B
sennidin B
Conditions | Yield |
---|---|
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
1,8-dihydroxy-3-carboxy-anthraquinone
Conditions | Yield |
---|---|
With chromium(VI) oxide; hydrogen bromide 1.) AcOH,; Yield given. Multistep reaction; |
1,8-dihydroxy-3-carboxy-anthraquinone
Conditions | Yield |
---|---|
With sulfuric acid; bromine 1.) H2O; Yield given; Multistep reaction; |
rhein-11-O-β-D-glucoside
1,8-dihydroxy-3-carboxy-anthraquinone
Conditions | Yield |
---|---|
With sodium hydroxide In methanol; water for 1h; Hydrolysis; Heating; | 4 mg |
1,8-dihydroxy-3-carboxy-anthraquinone
Conditions | Yield |
---|---|
With water; iron(III) chloride |
1,8-dihydroxy-3-carboxy-anthraquinone
Conditions | Yield |
---|---|
With chromium(VI) oxide; acetic acid |
1,8-dihydroxy-3-carboxy-anthraquinone
Conditions | Yield |
---|---|
With chromic acid | |
With chromic acid Acetylieren des Oxydationsproduktes und Auskochen des Acetylierungsproduktes mit Benzol, man verseift mit verd. Kalilauge; |
1,8-dihydroxy-3-carboxy-anthraquinone
Conditions | Yield |
---|---|
With acetic anhydride; chromic acid; acetic acid Behandeln des entstandenen Rheindiacetats mit Kalilauge; |
1,8-dihydroxy-3-carboxy-anthraquinone
1,8-dihydroxy-3-hydroxymethyl-9,10-anthracenedione
acetic acid
1,8-dihydroxy-3-carboxy-anthraquinone
1,8-dihydroxy-3-carboxy-anthraquinone
Conditions | Yield |
---|---|
With water; iron(III) chloride |
8-O-β-D-glucosyl-10-C-β-D-glucosyl rhein-9-anthrone
A
D-Glucose
B
1,8-dihydroxy-3-carboxy-anthraquinone
Conditions | Yield |
---|---|
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
A
D-Glucose
B
1,8-dihydroxy-3-carboxy-anthraquinone
Conditions | Yield |
---|---|
With sulfuric acid; iron(III) chloride for 0.5h; Product distribution; Heating; |
(2,4-dibromo-6-hydroxyphenyl)-(2-hydroxyphenyl)methanone
1,8-dihydroxy-3-carboxy-anthraquinone
Conditions | Yield |
---|---|
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
1,8-dihydroxy-3-carboxy-anthraquinone
Conditions | Yield |
---|---|
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
1,8-dihydroxy-3-carboxy-anthraquinone
Conditions | Yield |
---|---|
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 |
Conditions | Yield |
---|---|
With pyridine; dmap | 100% |
With dmap; triethylamine In acetic anhydride at 20℃; for 1h; | 95% |
With pyridine at 120℃; for 6h; | 93% |
1,8-dihydroxy-3-carboxy-anthraquinone
Conditions | Yield |
---|---|
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
Conditions | Yield |
---|---|
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
Conditions | Yield |
---|---|
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
BW-AQ-152
Conditions | Yield |
---|---|
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
1,8-dibenzyloxy-9,10-anthraquinone-3-carboxylic acid benzyl ester
Conditions | Yield |
---|---|
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
Conditions | Yield |
---|---|
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
C27H32O6
Conditions | Yield |
---|---|
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
C30H38O6
Conditions | Yield |
---|---|
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
methyl 4,5-dimethoxy-9,10-dioxo-9,10-dihydroanthracene-2-carboxylate
Conditions | Yield |
---|---|
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
BW-AQ-147
Conditions | Yield |
---|---|
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% |
Conditions | Yield |
---|---|
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
ethylene glycol
2-hydroxyethyl 4,5-dihydroxy-9,10-dioxo-9,10-dihydroanthracene-2-carboxylate
Conditions | Yield |
---|---|
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
benzyl chloride
1,8-dibenzyloxy-9,10-anthraquinone-3-carboxylic acid benzyl ester
Conditions | Yield |
---|---|
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% |
Conditions | Yield |
---|---|
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
O,O'-diethyl {[2-(4,5-dihydroxy-9,10-dioxo-9,10-dihydroanthracen-2-yl)acetylamino](2-methoxyphenyl)methyl}phosphonate
Conditions | Yield |
---|---|
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% |
Conditions | Yield |
---|---|
With tetrabutylammomium bromide; triethylamine In tetrahydrofuran at 20℃; | 89.8% |
Conditions | Yield |
---|---|
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
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
Conditions | Yield |
---|---|
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
diethylene glycol
2-(2-hydroxyethoxy)ethyl 4,5-dihydroxy-9,10-dioxo-9,10-dihydroanthracene-2-carboxylate
Conditions | Yield |
---|---|
With sulfuric acid at 85℃; for 1h; | 88% |
1,8-dihydroxy-3-carboxy-anthraquinone
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
Conditions | Yield |
---|---|
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% |
Conditions | Yield |
---|---|
With tetrabutylammomium bromide; triethylamine In tetrahydrofuran at 20℃; | 87.7% |
With tetrabutylammomium bromide; triethylamine In tetrahydrofuran at 20℃; for 18.08h; | 87.5% |
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
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. |
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