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Cas Database

Name	Chrysophanic acid	EINECS	207-572-2
CAS No.	481-74-3	Density	1.476 g/cm³
PSA	74.60000	LogP	2.18160
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	N/A	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-;	Article Data	83

Chrysophanic acid 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%

: 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%

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- .

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