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550-24-3

Basic Information
CAS No.: 550-24-3
Name: 2,5-Cyclohexadiene-1,4-dione,2,5-dihydroxy-3-undecyl-
Molecular Structure:
Molecular Structure of 550-24-3 (2,5-Cyclohexadiene-1,4-dione,2,5-dihydroxy-3-undecyl-)
Formula: C17H26 O4
Molecular Weight: 294.391
Synonyms: Embelin(6CI); p-Benzoquinone, 2,5-dihydroxy-3-undecyl- (7CI,8CI);2,5-Dihydroxy-3-undecyl-1,4-benzoquinone; Embelic acid; Emberine; NSC 91874
EINECS: N/A
Density: 1.131g/cm3
Melting Point: 142-143°C
Boiling Point: 431.9oC at 760 mmHg
Flash Point: 229.1oC
Solubility: N/A
Appearance: N/A
Hazard Symbols: N/A
Risk Codes: N/A
Safety: Poison by intraperitoneal route. Experimental reproductive effects. When heated to decomposition it emits acrid smoke and fumes.
Transport Information: N/A
PSA: 74.60000
LogP: 4.31310
Synthetic route
775350-90-8

2,5-bis-methylamino-3-undecyl-[1,4]benzoquinone

550-24-3

embelin

Conditions
ConditionsYield
With sulfuric acid; acetic acid
105-74-8

dilauryl peroxide

2.5-dihydroxy-benzoquinone-(1.4)

2.5-dihydroxy-benzoquinone-(1.4)

A

550-24-3

embelin

B

3.6-dihydroxy-2.5-diundecyl-benzoquinone-(1.4)

3.6-dihydroxy-2.5-diundecyl-benzoquinone-(1.4)

Conditions
ConditionsYield
With acetic acid at 92℃;
850878-20-5

3-undecyl-benzene-1,2,4,5-tetraol

alkali

alkali

air

air

550-24-3

embelin

56923-51-4

2-phenylamino-5-hydroxy-6-undecyl-1,4-naphthoquinone

alcoholic sulfate

alcoholic sulfate

A

550-24-3

embelin

B

62-53-3

aniline

112-16-3

n-dodecanoyl chloride

550-24-3

embelin

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1: sodium peroxide; petroleum ether; water / 0 - 10 °C
2: acetic acid / 92 °C
View Scheme
50-00-0

formaldehyd

550-24-3

embelin

109-92-2

ethyl vinyl ether

1063976-79-3

2-ethoxy-6-hydroxy-7-undecyl-3,4-dihydro-2H-chromene-5,8-dione

Conditions
ConditionsYield
In ethanol at 150℃; for 0.333333h; microwave irradiation;100%
550-24-3

embelin

5-chloro-2-((3-(3-nitrophenyl)prop-2-yn-1-yl)oxy)benzaldehyde

11-chloro-2-hydroxy-6-(3-nitrophenyl)-3-undecylchromeno[3,4-c]chromene-1,4(7H,12bH)dione

Conditions
ConditionsYield
With ethylenediaminediacetic acid In 1,2-dichloro-ethane at 120℃; for 0.166667h; Microwave irradiation; Sealed tube; regioselective reaction;100%
550-24-3

embelin

C17H28B2O8

Conditions
ConditionsYield
With borax In ethanol for 1h; Heating;98%
550-24-3

embelin

5220-49-5

3-amino-cyclohex-2-enone

456-48-4

3-Fluorobenzaldehyde

1448168-14-6

9-(3-fluorophenyl)-2-hydroxy-3-undecyl-6,7,9,10-tetrahydro-5H-acridine-1,4,8-trione

Conditions
ConditionsYield
In ethanol at 150℃; for 0.25h; Microwave irradiation;98%
550-24-3

embelin

5-chloro-2-((3-(3-methoxyphenyl)prop-2-yn-1-yl)oxy)benzaldehyde

11-chloro-2-hydroxy-6-(3-methoxyphenyl)-3-undecylchromeno-[3,4-c]chromene-1,4(7H,12bH)dione

Conditions
ConditionsYield
With ethylenediaminediacetic acid In 1,2-dichloro-ethane at 120℃; for 0.166667h; Microwave irradiation; Sealed tube; regioselective reaction;98%
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Chemistry

Molecular Structure of Embelic acid (CAS NO.550-24-3):


IUPAC: 2,5-Dihydroxy-3-undecylcyclohexa-2,5-diene-1,4-dione
Molecular Formula:C17H26O4
Molecular Weight:294.39
EINECS:208-979-8
Product Categories:Anthraquinones, Hydroquinones and Quinones;Caspases/Apoptosis
Density:1.131 g/cm3
Melting Point:142-143oC
Boiling Point:431.9oC at 760 mmHg
Flash Point:229.1oC
SMILES:O=C1/C=C(/O)C(=O)\C(=C1\O)CCCCCCCCCCC 
InChI:InChI=1/C17H26O4/c1-2-3-4-5-6-7-8-9-10-11-13-16(20)14(18)12-15(19)17(13)21/h12,18,21H,2-11H2,1H3 
InChIKey:IRSFLDGTOHBADP-UHFFFAOYAG 
Index of Refraction:1.537
Vapor pressure:2.85E-09 mmHg at 25oC
Molar Volume:260.1 cm3
Surface Tension:49.4 dyne/cm
Appearance:Orange crystals (MeOH or hexane/EtOH); Glistening orange plates (benzene, or acetic acid)
Molar Refractivity:81.33 cm3
Enthalpy of Vaporization:79.39 kJ/mol

Toxicity Data With Reference

1.    

ipr-uns LD50:44 mg/kg

    IJPPAZ    Indian Journal of Physiology and Pharmacology. 21 (1977),31.

Safety Profile

Poison by intraperitoneal route. Experimental reproductive effects. When heated to decomposition it emits acrid smoke and fumes.

Safty informations about Embelic acid (CAS NO.550-24-3):
WGK Germany:3
RTECS:DK4230000

Specification

 Embelic acid with cas registry number of 550-24-3 is also known as 2,5-Dihydroxy-3-undecyl-p-benzoquinon ; 4-Dione,2,5-dihydroxy-3-undecyl-5-cyclohexadiene-1 ; Embelicacid ; Emberine ; Apoptosis activator III ; Embelin ; 2,5-Dihydroxy-3-undecyl-1,4-benzoquinone ; 2,5-Dihydroxy-3-undecyl-2,5-cyclohexadiene-1,4-dione . It can be soluble in the usual hot organic solvents or in alkali hydroxide solvents but it is practically insoluble in water. Embelic acid is used as an anthelminthic and potent oral contraceptive.