(1,8-dihydroxy-9,10-dioxo-9,10-dihydroanthracen-3-yl)methyl acetate
1,8-dihydroxy-3-hydroxymethyl-9,10-anthracenedione
Conditions | Yield |
---|---|
With potassium hydroxide In ethanol for 0.166667h; Heating; | 100% |
With sodium hydroxide for 24h; Ambient temperature; | 94% |
1,8-dihydroxy-3-hydroxymethyl-9,10-anthracenedione
Conditions | Yield |
---|---|
With acetate buffer; β-glucosidase In water at 37℃; for 16h; pH=5.0; | 95% |
Enzymatic reaction; |
aloin
1,8-dihydroxy-3-hydroxymethyl-9,10-anthracenedione
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; |
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
1,8-dihydroxy-3-hydroxymethyl-9,10-anthracenedione
Conditions | Yield |
---|---|
With iron(III) chloride In water | 74% |
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 |
Conditions | Yield |
---|---|
With lithium aluminium tetrahydride In tetrahydrofuran at 0℃; for 2h; Reflux; | 65% |
A
1,8-dihydroxy-3-hydroxymethyl-9,10-anthracenedione
Conditions | Yield |
---|---|
With oxygen In aq. phosphate buffer; acetonitrile at 10℃; pH=6; | A 18% B 58% |
A
1,8-dihydroxy-3-hydroxymethyl-9,10-anthracenedione
Conditions | Yield |
---|---|
With lead(IV) tetraacetate; acetic acid at 0 - 20℃; | A 23% B 48% |
1,8-dihydroxy-3-(pivaloyloxymethyl)-9,10-antraquinone
1,8-dihydroxy-3-hydroxymethyl-9,10-anthracenedione
Conditions | Yield |
---|---|
With potassium tert-butylate; water In tetrahydrofuran; diethyl ether; dichloromethane at 20℃; for 12h; | 39% |
triacetyl aloe-emodin
1,8-dihydroxy-3-hydroxymethyl-9,10-anthracenedione
Conditions | Yield |
---|---|
With sulfuric acid |
1,8-dihydroxy-3-(hydroxymethyl)-9(10H)-anthracenone
1,8-dihydroxy-3-hydroxymethyl-9,10-anthracenedione
Conditions | Yield |
---|---|
With sodium hydroxide |
5-hydroxynaphtho-1,4-quinone
1,1-bis(trimethylsilyloxy)-3-trimethylsilyloxymethyl-1,3-butadiene
1,8-dihydroxy-3-hydroxymethyl-9,10-anthracenedione
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
1,8-dihydroxy-3-hydroxymethyl-9,10-anthracenedione
Conditions | Yield |
---|---|
With sodium methylate In methanol at 140 - 150℃; for 6h; |
water
iron(III) chloride
10-glucopyranosyl-1,8-dihydroxy-3-(hydroxymethyl)-9(10H)-anthracenone
1,8-dihydroxy-3-hydroxymethyl-9,10-anthracenedione
sulfuric acid
water
10-glucopyranosyl-1,8-dihydroxy-3-(hydroxymethyl)-9(10H)-anthracenone
1,8-dihydroxy-3-hydroxymethyl-9,10-anthracenedione
water
10-glucopyranosyl-1,8-dihydroxy-3-(hydroxymethyl)-9(10H)-anthracenone
1,8-dihydroxy-3-hydroxymethyl-9,10-anthracenedione
hydrogenchloride
ethanol
water
10-glucopyranosyl-1,8-dihydroxy-3-(hydroxymethyl)-9(10H)-anthracenone
A
D-Arabinose
B
1,8-dihydroxy-3-hydroxymethyl-9,10-anthracenedione
sulfuric acid
water
10-glucopyranosyl-1,8-dihydroxy-3-(hydroxymethyl)-9(10H)-anthracenone
A
1,8-dihydroxy-3-hydroxymethyl-9,10-anthracenedione
1,8-dihydroxy-3-hydroxymethyl-9,10-anthracenedione
Conditions | Yield |
---|---|
With ethanol; platinum; iron(II) chloride Hydrogenation; |
1,8-dihydroxy-3-hydroxymethyl-9,10-anthracenedione
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; |
1,8-dihydroxy-3-hydroxymethyl-9,10-anthracenedione
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
4,5-dihydroxy-9,10-dioxo-9,10-dihydroanthracene-2-carbaldehyde
1,8-dihydroxy-3-hydroxymethyl-9,10-anthracenedione
Conditions | Yield |
---|---|
Hydrogenation; |
1,8-dihydroxy-3-(hydroxymethyl)-9(10H)-anthracenone
1,8-dihydroxy-3-hydroxymethyl-9,10-anthracenedione
Conditions | Yield |
---|---|
Leiten von Luft; |
2-bromomethyl-9,10-dihydro-4,5-dihydroxy-9,10-dioxoanthracene
1,8-dihydroxy-3-hydroxymethyl-9,10-anthracenedione
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
1,8-dihydroxy-3-hydroxymethyl-9,10-anthracenedione
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 |
1,8-dihydroxy-3-hydroxymethyl-9,10-anthracenedione
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 |
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
1,8-dihydroxy-3-hydroxymethyl-9,10-anthracenedione
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
3-(chloromethyl)-1,8-dihydroxyanthracene-9,10-dione
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
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% |
1,8-dihydroxy-3-hydroxymethyl-9,10-anthracenedione
sodium methansulfinate
Conditions | Yield |
---|---|
With boron trifluoride diethyl etherate; acetic acid at 20℃; | 90% |
1,8-dihydroxy-3-hydroxymethyl-9,10-anthracenedione
2-bromomethyl-9,10-dihydro-4,5-dihydroxy-9,10-dioxoanthracene
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
dimethyl sulfate
3-(hydroxymethyl)-1,8-dimethoxy-9,10-anthracenedione
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
1,8-dihydroxy-3-hydroxymethyl-9,10-anthracenedione
A
3-hydroxymethyl-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
benzoyl chloride
1,8-bis-benzoyloxy-3-benzoyloxymethyl-anthraquinone
Conditions | Yield |
---|---|
With potassium carbonate In acetone at 60℃; for 24h; | 78% |
With pyridine |
1,8-dihydroxy-3-hydroxymethyl-9,10-anthracenedione
acetic anhydride
triacetyl aloe-emodin
Conditions | Yield |
---|---|
With pyridine at 50℃; for 24h; | 76% |
With sodium acetate |
1,8-dihydroxy-3-hydroxymethyl-9,10-anthracenedione
benzyl chloride
1,8-dibenzyloxy-3-(hydroxymethyl)anthraquinone
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
1,8-dihydroxy-3-hydroxymethyl-9,10-anthracenedione
3-hydroxymethyl-1,8-diisopropoxyanthraquinone
Conditions | Yield |
---|---|
With caesium carbonate In acetone for 96h; Heating; | 72% |
1,8-dihydroxy-3-hydroxymethyl-9,10-anthracenedione
p-toluenesulfonyl chloride
C29H22O9S2
Conditions | Yield |
---|---|
With potassium carbonate In acetone at 60℃; for 6h; | 70% |
1,8-dihydroxy-3-hydroxymethyl-9,10-anthracenedione
4,5-dihydroxy-9,10-dioxo-9,10-dihydroanthracene-2-carbaldehyde
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
3-(hydroxymethyl)-1,8-dimethoxy-9,10-anthracenedione
Conditions | Yield |
---|---|
With potassium carbonate In N,N-dimethyl-formamide at 55℃; for 20h; | 53.1% |
1,8-dihydroxy-3-hydroxymethyl-9,10-anthracenedione
acetic acid
A
Chrysophanol
B
(1,8-dihydroxy-9,10-dioxo-9,10-dihydroanthracen-3-yl)methyl acetate
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
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
Conditions | Yield |
---|---|
With 3 A molecular sieve; silver trifluoromethanesulfonate In dichloromethane for 4h; Ambient temperature; | 49% |
1-bromo-hexane
1,8-dihydroxy-3-hydroxymethyl-9,10-anthracenedione
1,8-di-O-hexylaloe-emodin
Conditions | Yield |
---|---|
With potassium carbonate In N,N-dimethyl-formamide Reflux; | 49% |
1-Iodododecane
1,8-dihydroxy-3-hydroxymethyl-9,10-anthracenedione
1,8-di-O-dodecylaloe-emodin
Conditions | Yield |
---|---|
With potassium carbonate In N,N-dimethyl-formamide Reflux; | 40% |
1,8-dihydroxy-3-hydroxymethyl-9,10-anthracenedione
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
1,8-dihydroxy-3-hydroxymethyl-9,10-anthracenedione
1,8-di-O-octadecylalor-emodin
Conditions | Yield |
---|---|
With potassium carbonate In N,N-dimethyl-formamide Reflux; | 36% |
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 cm3
Molar Volume: 169.7 cm3
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 (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.
Hazard Codes: Xi
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 (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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