Chrysophanic acid supplier

Name
Chrysophanic acid
EINECS 207-572-2
CAS No. 481-74-3
Article Data83
CAS DataBase
Density 1.476 g/cm³
Solubility water: <0.1 g/100 mL at 18 °C
Melting Point 194-198 °C
Formula C₁₅H₁₀O₄
Boiling Point 489.495 °C at 760 mmHg
Molecular Weight 254.242
Flash Point 263.939 °C
Transport Information
Appearance yellow crystalline solid or brown powder
Safety 26-37/39
Risk Codes 36/37/38
Molecular Structure
Hazard Symbols Xi
Synonyms 1,8-Dihydroxy-3-methylanthraquinone;9,10-Anthracenedione, 1,8-dihydroxy-3-methyl- (9CI);1,8-dihydroxy-3-methyl-9,10-anthraquinone;C.I. Natural Yellow 23;Anthraquinone, 1,8-dihydroxy-3-methyl-;Chrysophansaeure;9,10-Anthracenedione, 1, 8-dihydroxy-3-methyl-;3-Methyl-1, 8-dihydroxyanthraquinone;9,10-Anthracenedione,1,8-dihydroxy-3- methyl-;
PSA 74.60000
LogP 2.18160

Synthetic route

: 67116-22-7
8-hydroxy-1-methoxy-3-methylanthracene-9,10-dione

: 481-74-3
Chrysophanol

Conditions

Conditions	Yield
With hydrogen bromide In acetic acid for 5h; Heating;	100%
With hydrogen bromide In acetic acid for 5h; Heating;	100%
With hydrogen bromide; acetic acid Yield given;

: 13241-28-6, 67492-66-4
Chrysophanol 8-O-beta-D-glucopyranoside

: 481-74-3
Chrysophanol

Conditions

Conditions	Yield
With acetate buffer; β-glucosidase In water at 37℃; for 16h; pH=5.0;	98%

: 108637-78-1
(1R,4aS,9aR)-9a-Chloro-8-hydroxy-1-methoxy-3-methyl-1-trimethylsilanyloxy-1,4,4a,9a-tetrahydro-anthraquinone

A: 481-74-3
Chrysophanol

B: 67116-22-7
8-hydroxy-1-methoxy-3-methylanthracene-9,10-dione

Conditions

Conditions	Yield
1,8-diazabicyclo[5.4.0]undec-7-ene In methanol; dichloromethane Ambient temperature;	A n/a B 96%
sodium acetate In methanol; dichloromethane Ambient temperature; Yield given. Yields of byproduct given;

: 71013-35-9
1,8-dimethoxy-3-methyl-9,10-anthraquinone

: 481-74-3
Chrysophanol

Conditions

Conditions	Yield
With hydrogen bromide; acetic acid for 0.5h; Heating;	94%
With hydrogen bromide In acetic acid for 0.5h; Heating;	94%
With nicotinic acid; sulfuric acid; boric acid at 120℃; for 2h;	45%

: 3300-25-2
8-O-methylchrysophanol

: 481-74-3
Chrysophanol

Conditions

Conditions	Yield
With boron tribromide In dichloromethane at -50℃; for 7h;	93%
With aluminium trichloride In dichloromethane at 20℃;	91%
With hydrogen bromide; acetic acid
With hydrogen bromide for 0.5h;

: 52431-65-9
3-Bromojuglone

: 99097-63-9
(1E,3Z)-1-Methoxy-3-methyl-1,4-bis-trimethylsilanyloxy-buta-1,3-diene

: 481-74-3
Chrysophanol

Conditions

Conditions	Yield
Stage #1: 3-Bromojuglone; (1E,3Z)-1-Methoxy-3-methyl-1,4-bis-trimethylsilanyloxy-buta-1,3-diene In benzene for 5h; Heating; Stage #2: With hydrogenchloride In tetrahydrofuran for 2h; Heating; Further stages.;	79%

: 76695-94-8
1,4,4a,9a-Tetrahydro-1,8-dihydroxy-3-methyl-9,10-anthrachinon

: 481-74-3
Chrysophanol

Conditions

Conditions	Yield
With pyridinium chlorochromate In dichloromethane for 4h;	76%
With pyridinium chlorochromate

: 518-82-1
1,6,8-trihydroxy-3-methyl-9,10-anthraquinone

A: 481-74-3
Chrysophanol

B: 1396259-15-6
(R)-3,4-dihydro-3,8,9,10-tetrahydroxy-6-methylanthracen-1(2H)-one

Conditions

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 12% B 74%
With glucose dehydrogenase; sodium dithionite; D-glucose; anthrol reductase of Talaromyces islandicus WF-38-12; NADP In aq. buffer for 14h; pH=7; Catalytic behavior; Kinetics; pH-value; Enzymatic reaction; stereoselective reaction;	A n/a B 74%
Stage #1: 1,6,8-trihydroxy-3-methyl-9,10-anthraquinone With sodium dithionite Stage #2: With N-terminally His-tagged 17β-hydroxysteroid dehydrogenase from the filamentous fungus Curvularia lunata (teleomorph Cochlioboluslunatus) cloned into pET19b; NADPH Enzymatic reaction;	A 8% B 32%
With sodium dithionite; D-glucose; his-tagged AflM from Aspergillus parasiticus; C21H27N7O17P3(1-)*Na(1+) In aq. phosphate buffer at 20℃; for 24h; pH=7; Inert atmosphere; Enzymatic reaction;	A 8 %Spectr. B 20%

: 1396259-15-6
(R)-3,4-dihydro-3,8,9,10-tetrahydroxy-6-methylanthracen-1(2H)-one

A: 481-74-3
Chrysophanol

B: 518-82-1
1,6,8-trihydroxy-3-methyl-9,10-anthraquinone

C: 39546-16-2, 115729-00-5
(−)-flavoskyrin

Conditions

Conditions	Yield
With oxygen In aq. phosphate buffer; acetonitrile at 10℃; for 10h; pH=6; Solvent;	A 10% B n/a C 72%

...Expand

: 1396259-15-6
(R)-3,4-dihydro-3,8,9,10-tetrahydroxy-6-methylanthracen-1(2H)-one

A: 481-74-3
Chrysophanol

B: (-)-flavoskyrin

Conditions

Conditions	Yield
With lead(IV) tetraacetate; acetic acid at 0 - 20℃; for 0.333333h;	A 8% B 68%

: 18855-92-0
3-chlorojuglone

: 76927-59-8
(E)-((1-methoxy-3-methylbuta-1,3-dien-1-yl)oxy)trimethylsilane

A: 481-74-3
Chrysophanol

B: 67116-22-7
8-hydroxy-1-methoxy-3-methylanthracene-9,10-dione

Conditions

Conditions	Yield
In neat (no solvent) Ambient temperature;	A 63% B 4%

...Expand

: 18855-92-0
3-chlorojuglone

: 76927-59-8
(E)-((1-methoxy-3-methylbuta-1,3-dien-1-yl)oxy)trimethylsilane

A: 481-74-3
Chrysophanol

B: 67116-22-7
8-hydroxy-1-methoxy-3-methylanthracene-9,10-dione

C: 95393-72-9
methyl 3-methyl-4-<3-chloro-5-hydroxynaphthoquinonyl-2>-2-butenoate

Conditions

Conditions	Yield
In neat (no solvent) Product distribution; Ambient temperature; different solvent, reaction times and temperatures;	A 63% B 4% C n/a

...Expand

: bulbine-knipholone

A: 481-74-3
Chrysophanol

B: 7507-89-3
2,6-dihydroxy-4-methoxy-acetophenone

Conditions

Conditions	Yield
With sodium dithionite In sodium hydroxide at 70℃; for 1h;	A 61% B n/a

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

: 64-19-7
acetic acid

A: 481-74-3
Chrysophanol

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

Conditions

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

...Expand

: 1396259-15-6
(R)-3,4-dihydro-3,8,9,10-tetrahydroxy-6-methylanthracen-1(2H)-one

A: 481-74-3
Chrysophanol

B: (R)-3,8-dihydroxy-6-methyl-3,4-dihydroanthracene-1,9,10(2H)-trione

C: (-)-flavoskyrin

Conditions

Conditions	Yield
With lead(IV) tetraacetate; acetic acid at 20℃; for 0.333333h;	A 21% B 41% C 35%

...Expand

: 18855-92-0
3-chlorojuglone

: 76927-59-8
(E)-((1-methoxy-3-methylbuta-1,3-dien-1-yl)oxy)trimethylsilane

A: 481-74-3
Chrysophanol

B: 95393-72-9
methyl 3-methyl-4-<3-chloro-5-hydroxynaphthoquinonyl-2>-2-butenoate

Conditions

Conditions	Yield
In tetrahydrofuran -30 deg C, 30 min, -30 deg C to RT, 1h;	A 22% B 14%

...Expand

: 1313-13-9
manganese dioxide

: 1-acetoxy-3-methyl-5-hydroxy-9,10-dioxo-1,4,4a,9,9a,10-hexahydroanthracene

1-acetoxy-3-methyl-1,1a,4,4a-tetrahydroanthranone: 1-acetoxy-3-methyl-1,1a,4,4a-tetrahydroanthranone

: 52062-24-5
(E)-1-acetoxy-3-methyl-1,3-butadiene

: 481-39-0
5-hydroxynaphtho-1,4-quinone

: 481-74-3
Chrysophanol

Conditions

Conditions	Yield
With acetic anhydride; hydroquinone In sodium carbonate; toluene	9%

...Expand

: 18713-45-6
1,8-diacetoxy-3-methyl-anthraquinone

: 481-74-3
Chrysophanol

Conditions

Conditions	Yield
With potassium hydroxide

: 491-58-7
1,8-dihydroxy-3-methylanthracen-9(10H)-one

: 481-74-3
Chrysophanol

Conditions

Conditions	Yield
With chromium(VI) oxide; acetic acid
Product distribution; Mechanism; biotransformation by emodinanthrone oxygenase from Aspergillus terreus: relative activity;

: 857537-29-2
cephalanone F

: 481-74-3
Chrysophanol

Conditions

Conditions	Yield
With aluminium trichloride; sodium chloride at 175℃;
With sulfuric acid; boric acid

: 871893-24-2
8-amino-1-hydroxy-3-methyl-anthraquinone

: 481-74-3
Chrysophanol

Conditions

Conditions	Yield
With sulfuric acid Diazotization.und Erwaermen der Reaktions-Loesung auf 120grad;
With sulfuric acid Diazotization.und Erwaermen der Reaktions-Loesung auf 120grad;

: 39546-16-2, 115729-00-5
(−)-flavoskyrin

: 481-74-3
Chrysophanol

Conditions

Conditions	Yield
at 210℃;

: 518-82-1
1,6,8-trihydroxy-3-methyl-9,10-anthraquinone

: 481-74-3
Chrysophanol

Conditions

Conditions	Yield
With mercaptoethyl alcohol; cell-free extract from Pyenochaeta terrestris; ATP; NADPH; iron(II) chloride at 25℃; for 5h;
With glycerol; 2-hydroxyethanethiol; NADPH; emodin deoxygenase In water at 25℃; Equilibrium constant; Kinetics; effect of ATP, dithiothreitol, p-hydroxymercuribenzoic acid, diamide, N-ethylmaleimide, Fe2+, or Cd2+ on catalyst activity;
Multi-step reaction with 3 steps 1.1: sodium tetrahydroborate; sodium dithionite / water; dimethyl sulfoxide / 0.17 h / 20 °C / Inert atmosphere; Green chemistry 1.2: 20 °C / Inert atmosphere; Green chemistry 2.1: Chiralcel OD-H / hexane; isopropyl alcohol / 20 °C / Resolution of racemate 3.1: (S)-(+)-2-methoxy-2-trifluoromethyl-2-phenylacetyl chloride; pyridine / 24 h / 20 °C View Scheme

: 481-39-0
5-hydroxynaphtho-1,4-quinone

: 73311-51-0
1-methoxy-3-methyl-1-trimethylsilyloxy-1,3-butadiene

A: 481-74-3
Chrysophanol

B: 67116-22-7
8-hydroxy-1-methoxy-3-methylanthracene-9,10-dione

Conditions

Conditions	Yield
With 2,3-dicyano-5,6-dichloro-p-benzoquinone 1) CH2Cl2, 6 h, 2) 2 h; Yield given. Multistep reaction. Yields of byproduct given;

...Expand

: 481-39-0
5-hydroxynaphtho-1,4-quinone

: 155787-91-0
3-methyl-1-triethylsilyloxy-1-trimethylsilyloxy-1,3-butadiene

: 481-74-3
Chrysophanol

Conditions

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

: 112683-58-6
emodin

: 481-74-3
Chrysophanol

Conditions

Conditions	Yield
With emodin deoxygenase; NADPH Mechanism; rate of conversion;

: 108637-74-7
(1R,4aR,9aS)-8-Hydroxy-1-methoxy-3-methyl-1-trimethylsilanyloxy-1,4,4a,9a-tetrahydro-anthraquinone

A: 481-74-3
Chrysophanol

B: 67116-22-7
8-hydroxy-1-methoxy-3-methylanthracene-9,10-dione

Conditions

Conditions	Yield
With hydrogenchloride In methanol; dichloromethane Ambient temperature; Yield given. Yields of byproduct given;
With 2,3-dicyano-5,6-dichloro-p-benzoquinone In dichloromethane Ambient temperature; Yield given. Yields of byproduct given;

: 94450-08-5, 778648-08-1, 949907-88-4
(+)-knipholone

A: 481-74-3
Chrysophanol

B: 3602-54-8
4,6-dihydroxy-2-methoxyacetophenone

Conditions

Conditions	Yield
With sodium dithionate; sodium hydroxide at 80℃; for 1h;

: (R)-prechrysophanol

: 481-74-3
Chrysophanol

Conditions

Conditions	Yield
With potassium hydroxide In methanol for 72h;	6 mg

: isofoliosone

A: 481-74-3
Chrysophanol

B: 3602-54-8
4,6-dihydroxy-2-methoxyacetophenone

Conditions

Conditions	Yield
With potassium hydroxide; sodium dithionite In methanol

: 481-74-3
Chrysophanol

: 108-24-7
acetic anhydride

: 18713-45-6
1,8-diacetoxy-3-methyl-anthraquinone

Conditions

Conditions	Yield
With sulfuric acid for 0.5h; Ambient temperature;	100%
With sulfuric acid
With sodium acetate

: 481-74-3
Chrysophanol

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

Conditions

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%

: 481-74-3
Chrysophanol

: 98-59-9
p-toluenesulfonyl chloride

: C29H22O8S2

Conditions

Conditions	Yield
With potassium carbonate In acetone at 70℃; for 20h;	98%

: 481-74-3
Chrysophanol

: 77-78-1
dimethyl sulfate

: 71013-35-9
1,8-dimethoxy-3-methyl-9,10-anthraquinone

Conditions

Conditions	Yield
With potassium carbonate In acetone for 16h; Heating;	96%
With potassium carbonate In acetone for 6h; Heating;	89%
With potassium carbonate at 75℃; for 12h;	65%
With potassium hydroxide
With potassium carbonate In acetone for 10h; Heating; Yield given;

: 481-74-3
Chrysophanol

: C15H8Cl6O5P2

Conditions

Conditions	Yield
With phosphorus pentachloride; water In benzene Rearrangement; phosphorylation; hydrolysis;	95%

: 481-74-3
Chrysophanol

: 491-58-7
1,8-dihydroxy-3-methylanthracen-9(10H)-one

Conditions

Conditions	Yield
With hydrogenchloride; acetic acid; tin(ll) chloride at 80℃; for 5h;	94%
With hydrogenchloride; tin; acetic acid
With ammonia; zinc
With hydrogen iodide

: 481-74-3
Chrysophanol

: 620-05-3
iodomethylbenzene

: 1612770-48-5
1,8-bis(benzyloxy)-3-methylanthracene-9,10-dione

Conditions

Conditions	Yield
With potassium carbonate In acetone for 12h; Reflux;	94%

: 481-74-3
Chrysophanol

: 74-88-4
methyl iodide

: 71013-35-9
1,8-dimethoxy-3-methyl-9,10-anthraquinone

Conditions

Conditions	Yield
With potassium carbonate In acetone for 12h; Reflux;	89%
With silver(l) oxide

: 481-74-3
Chrysophanol

: 287208-66-6
1-iodo-4-(iodomethyl)benzene

: 1612770-50-9
1,8-bis(4-iodobenzyloxy)-3-methylanthracene-9, 10-dione

Conditions

Conditions	Yield
With potassium carbonate In acetone for 12h; Reflux;	87%

: 481-74-3
Chrysophanol

: 542-69-8
1-iodo-butane

: 1612770-46-3
1,8-dibutoxy-3-methylanthracene-9,10-dione

Conditions

Conditions	Yield
With potassium carbonate In acetone for 12h; Reflux;	84%

: 481-74-3
Chrysophanol

: 107-08-4
1-iodo-propane

: 20317-77-5
1,8-dipropyloxy-3-methylanthracene-9,10-dione

Conditions

Conditions	Yield
With potassium carbonate In acetone for 12h; Reflux;	82%

: 481-74-3
Chrysophanol

: 81206-50-0
1-(iodomethyl)-2-bromobenzene

: 1612770-51-0
1,8-bis(2-bromobenzyloxy)-3-methylanthracene-9, 10-dione

Conditions

Conditions	Yield
With potassium carbonate In acetone for 12h; Reflux;	80%

: 481-74-3
Chrysophanol

: 556-56-9
allyl iodid

: 1612770-47-4
1,8-bis(allyloxy)-3-methylanthracene-9, 10-dione

Conditions

Conditions	Yield
With potassium carbonate In acetone for 12h; Reflux;	80%

: 481-74-3
Chrysophanol

: 75-03-6
ethyl iodide

: 1,8-diethoxy-3-methylanthracene-9,10-dione

Conditions

Conditions	Yield
With potassium carbonate In acetone for 12h; Reflux;	73%
With silver(l) oxide

: 481-74-3
Chrysophanol

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

Conditions

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

: 481-74-3
Chrysophanol

: 70450-41-8
1-chloro-3-(iodomethyl)benzene

: 1612770-49-6
1,8-bis(3-chlorobenzyloxy)-3-methylanthracene-9, 10-dione

Conditions

Conditions	Yield
With potassium carbonate In acetone for 12h; Reflux;	70%

Chrysophanic acid Chemical Properties

IUPAC Name: 1,8-Dihydroxy-3-methylanthracene-9,10-dione
Molecular formula: C₁₅H₁₀O₄
Molecular Weight: 254.24
EINECS: 207-572-2
Melting point: 194-198 °C
Boiling Point: 489.5 °C at 760 mmHg
Flash Point: 263.9 °C
Index of Refraction: 1.709
Molar Refractivity: 67.25 cm³
Molar Volume: 172.2 cm³
Surface Tension: 73.1 dyne/cm
Density: 1.476 g/cm³
Enthalpy of Vaporization: 78.46 kJ/mol
Vapour Pressure: 3.31E-10 mmHg at 25 °C
Water Solubility: <0.1 g/100 mL at 18 °C
Stability: Stable. Incompatible with strong oxidizing agents.
Appearance: yellow crystalline solid or brown powder
Classification Code of Chrysophanol (CAS NO.481-74-3): Mutagens; Mutation data; Noxae

Chrysophanic acid Safety Profile

Hazard Codes of Chrysophanol (CAS NO.481-74-3): Xi
Risk Statements:
36/37/38: Irritating to eyes, respiratory system and skin
36/38: Irritating to eyes and skin
Safety Statements:
26: In case of contact with eyes, rinse immediately with plenty of water and seek medical advice
36: Wear suitable protective clothing
36: Wear suitable protective clothing
WGK Germany: 3
RTECS: CB6725000

Chrysophanic acid Specification

Chrysophanol (CAS NO.481-74-3), its Synonyms are 1,8-Dihydroxy-3-methyl-9,10-anthracenedione ; 1,8-Dihydroxy-3-methylanthraquinone ; 3-Methylchrysazin ; 4,5-Dihydroxy-2-methylanthraquinone ; Chrysophanic acid ; Turkey rhubarb ; 9,10-Anthracenedione, 1,8-dihydroxy-3-methyl- ; 9,10-Anthracenedione, 1,8-dihydroxy-3-methyl- (9CI) ; Anthraquinone, 1,8-dihydroxy-3-methyl- .

Product Name

Chrysophanic acid

Synthetic route

Chrysophanic acid Chemical Properties

Chrysophanic acid Safety Profile

Chrysophanic acid Specification

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