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518-82-1

Basic Information
CAS No.: 518-82-1
Name: Emodin
Article Data: 56
Cas Database
Molecular Structure:
Molecular Structure of 518-82-1 (Emodin)
Formula: C15H10O5
Molecular Weight: 270.241
Synonyms: 6-Methyl-1,3,8-trihydroxyanthraquinone;Frangula emodin;1,3, 8-Trihydroxy-6-methylanthraquinone;6-Methyl-1,3,8-trihydroxy-9,10-anthracenedione;1,3, 8-Trihydroxy-6-methyl-9,10-anthraquinone;9,10-Anthracenedione,1,3,8-trihydroxy-6- methyl-;Anthraquinone, 6-methyl-1,3,8-trihydroxy-;Anthraquinone, 1,3,8-trihydroxy-6-methyl-;Rheum emodin;1,3,8-Trihydroxy-6-methyl-9,10-anthracenedione;9,10-Anthracenedione, 1,3,8-trihydroxy-6-methyl-;C.I. 75440;9,10-Anthracenedione, 1,3,8-trihydroxy-6-methyl- (9CI);1,3,8-Trihydroxy-6-methylanthraquinone;3-Methyl-1,6, 8-trihydroxyanthraquinone;Huperzines A;Polygonum Cuspidatum P.E;Emodine;
EINECS: 208-258-8
Density: 1.583 g/cm3
Melting Point: 255 °C (dec.)(lit.)
Boiling Point: 586.9 °C at 760 mmHg
Flash Point: 322.8 °C
Solubility: <0.1 g/100 mL at 19 °C in water
Appearance: red-orange powder
Hazard Symbols: IrritantXi
Risk Codes: 36/37/38
Safety: 26-36-37/39-36/37
Transport Information: N/A
PSA: 94.83000
LogP: 1.88720
Synthetic route
6030-60-0

1,6,8-triacetoxy-3-methyl-9,10-anthraquinone

518-82-1

1,6,8-trihydroxy-3-methyl-9,10-anthraquinone

Conditions
ConditionsYield
With sodium hydroxide at 80℃; for 2h;100%
With water; trifluoroacetic acid at 72℃; for 20h;42%
521-61-9

physcion

518-82-1

1,6,8-trihydroxy-3-methyl-9,10-anthraquinone

Conditions
ConditionsYield
With boron tribromide In dichloromethane at 0 - 20℃; Inert atmosphere;98%
With hydrogen bromide; acetic acid
With hydrogen bromide
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
ConditionsYield
With oxygen In aq. phosphate buffer; acetonitrile at 10℃; for 10h; pH=6; Solvent;A 10%
B n/a
C 72%
6414-42-2

1,3,8-trimethoxy-6-methyl-9,10-anthraquinone

518-82-1

1,6,8-trihydroxy-3-methyl-9,10-anthraquinone

Conditions
ConditionsYield
With sulfuric acid at 160℃;
481-70-9

endocrocin

518-82-1

1,6,8-trihydroxy-3-methyl-9,10-anthraquinone

Conditions
ConditionsYield
at 320℃;
With quinoline; copper oxide-chromium oxide at 170 - 190℃;
54130-71-1

2-(2-hydroxy-4-methyl-benzoyl)-3,5-dimethoxy-benzoic acid

518-82-1

1,6,8-trihydroxy-3-methyl-9,10-anthraquinone

Conditions
ConditionsYield
With sulfuric acid; sulfur trioxide; boric acid Erhitzen des Reaktionsprodukts mit KBr und H3PO4;
861790-72-9

1,3-diamino-8-hydroxy-6-methyl-anthraquinone

518-82-1

1,6,8-trihydroxy-3-methyl-9,10-anthraquinone

Conditions
ConditionsYield
With sulfuric acid Diazotization.Erhitzen des Reaktionsgemisches auf dem Wasserbad;
With sulfuric acid Diazotization.Erhitzen des Reaktionsgemisches auf dem Wasserbad;
4923-54-0

5,7-dihydroxy-1,4-naphthoquinone

155787-91-0

3-methyl-1-triethylsilyloxy-1-trimethylsilyloxy-1,3-butadiene

518-82-1

1,6,8-trihydroxy-3-methyl-9,10-anthraquinone

Conditions
ConditionsYield
With hydrogenchloride 1.) toluene, 80-100 deg C, 3 h; 2.) MeOH, rt., 10 h; Yield given. Multistep reaction;
5018-84-8

emodin-6,8-di-O-methyl ether

518-82-1

1,6,8-trihydroxy-3-methyl-9,10-anthraquinone

Conditions
ConditionsYield
With hydrogen bromide In acetic acid Heating;
With hydrogen bromide In acetic acid for 24h; Heating;6 mg
Multi-step reaction with 2 steps
1: AlCl3
2: HBr
View Scheme
81892-82-2

1,2,6,7,8-pentamethoxy-3-methylanthraquinone

518-82-1

1,6,8-trihydroxy-3-methyl-9,10-anthraquinone

Conditions
ConditionsYield
With chromium(VI) oxide; phosphorus; hydrogen iodide 1.) reflux, 5.5 h; 2.) Ac2O, AcOH, reflux, 2 h; Yield given. Multistep reaction;
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Chemistry

Molecular Structure of Emodin (CAS NO.518-82-1):

IUPAC Name: 1,3,8-trihydroxy-6-methylanthracene-9,10-dione 
Empirical Formula: C15H10O5
Molecular Weight: 270.2369
CAS Registry Number: 518-82-1
EINECS: 208-258-8
H bond acceptors: 5
H bond donors: 3
Freely Rotating Bonds: 3
Polar Surface Area: 61.83Å2
Index of Refraction: 1.744
Molar Refractivity: 69.13 cm3
Molar Volume: 170.6 cm3
Surface Tension: 85.4 dyne/cm
Density: 1.583 g/cm3
Flash Point: 322.8 °C
Enthalpy of Vaporization: 90.88 kJ/mol
Boiling Point: 586.9 °C at 760 mmHg
Vapour Pressure: 2.27E-14 mmHg at 25°C
Melting point: 253-257 oC
Water solubility: <0.1 g/100 mL at 19 oC
Storage temp: 2-8°C
Product Categories: Anthraquinones, Hydroquinones and Quinones; Anthraquinones; Hydroxyanthraquinones; Natural Plant Extract; The group of Polydatin; Protein Kinase; plant extract; Nutritional Ingredients

Toxicity Data With Reference

1.    

mmo-sat 50 µg/plate

    BCSTB5    Biochemical Society Transactions. 5 (1977),1489.
2.    

mma-sat 10 µg/plate

    MUREAV    Mutation Research. 125 (1984),135.
3.    

ipr-mus LD50:35 mg/kg

    JAFCAU    Journal of Agricultural and Food Chemistry. 27 (1979),1342.

Consensus Reports

EPA Genetic Toxicology Program.

Safety Profile

Poison by intraperitoneal route. Mutation data reported. When heated to decomposition it emits acrid smoke and irritating fumes.
Hazard Codes: IrritantXi
Risk Statements: 36/37/38
R36/37/38:Irritating to eyes, respiratory system and skin.
Safety Statements: 26-36-37/39-36/37
S26: In case of contact with eyes, rinse immediately with plenty of water and seek medical advice. 
S36:Wear suitable protective clothing. 
S37/39:Wear suitable gloves and eye/face protection. 
S36/37:Wear suitable protective clothing and gloves.
WGK Germany: 3
RTECS: CB7920600
F: 8-10-23

Specification

  Emodin , with CAS number of 518-82-1, can be called 1,3,8-Trihydroxy-6-methylanthraquinone ; 6-Methyl-1,3,8-trihydroxyanthraquinone ; C.I. 75440 ; C.I. Natural Yellow 14 ; 1,3,8-Trihydroxy-6-methylanthraquinone ; 1,3,8-trihydroxy-6-methylanthra-9,10-quinone . Emodin (CAS NO.518-82-1)  is a purgative resin from rhubarb and the buckthorn. The term may also refer to any one of a series of principles isomeric with the emodin of rhubarb. When heated to decomposition Emodin emits acrid smoke and irritating fumes.