CAS No.58186-27-9,Idebenone Suppliers

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Basic Information

Molecular Structure:
CAS No.:	58186-27-9
Name:	Idebenone
Article Data:	18

Formula:	C₁₉H₃₀O₅
Molecular Weight:	338.444
Synonyms:	2,5-Cyclohexadiene-1,4-dione,2-(10-hydroxydecyl)- 5,6-dimethoxy-3-methyl-;Idebenone (JAN);2,5-Cyclohexadiene-1,4-dione, 5,6-dimethoxy-2-(10-hydroxydecyl)-3-methyl-;6-(10-Hydroxydecyl)-2,3-dimethoxy-5-methyl-1,4-benzoquinone;CV 2619;Idebenone [GMP];2-(10-Hydroxydecyl)-5,6-dimethoxy-3-methyl-p-benzoquinone;Idebenonum [Latin];Idebenone [INN:JAN];Idebenona [GMP];Idebenona [Spanish];2-(10-hydroxydecyl)-5,6-dimethoxy-3-methyl-cyclohexa-2,5-diene-1,4-dione;Idenbenone;
EINECS:	1308068-626-2
Density:	1.08 g/cm³
Melting Point:	52-55 °C
Boiling Point:	497.3 °C at 760 mmHg
Flash Point:	170.1 °C
Appearance:	Yellow-orange crystalline powder
Hazard Symbols:	Xi
Risk Codes:	Xi
PSA:	72.83000
LogP:	3.46230

Synthetic route

: 1286209-74-2
10-(2,3,4-trimethoxy-6-methylphenyl)decan-1-ol

: 58186-27-9
Idebenone

Conditions

Conditions	Yield
With ammonium peroxydisulfate; nitric acid In water; acetone at 50℃; for 2.16h;	98%
Multi-step reaction with 3 steps 1: iodine / 1 h / 25 °C 2: dihydrogen peroxide; toluene-4-sulfonic acid / acetic acid / 0.42 h / 75 °C 3: sodium carbonate / methanol; water / 20 h / 25 °C View Scheme

disodium nitrosodisulfonate: disodium nitrosodisulfonate

: 77712-29-9
6-(10-hydroxydecyl)-2,3-dimethoxy-5-methylphenol

: 58186-27-9
Idebenone

Conditions

Conditions	Yield
In methanol; water	96.9%

: 77712-29-9
6-(10-hydroxydecyl)-2,3-dimethoxy-5-methylphenol

: 58186-27-9
Idebenone

Conditions

Conditions	Yield
With oxygen; salcomine In N,N-dimethyl-formamide for 72h; Ambient temperature;	87%
With potassium nitrososulfonate In sodium hydroxide for 1h; Ambient temperature;	67%
With oxygen; salcomine In N,N-dimethyl-formamide Quantum yield; Ambient temperature; reaction time, additive;

: 1251831-79-4
2,3-dimethoxy-6-methyl-5-benzyloxydecyl-p-benzoquinone

: 58186-27-9
Idebenone

Conditions

Conditions	Yield
Stage #1: 2,3-dimethoxy-6-methyl-5-benzyloxydecyl-p-benzoquinone With palladium 10% on activated carbon; hydrogen In methanol at 23℃; for 24h; Stage #2: With palladium 10% on activated carbon; oxygen In methanol at 23℃; for 24h;	82%

: 58186-28-0
2,3-dimethoxy-5-methyl-6-(10'-acetoxydecyl)-1,4-benzoquinone

: 58186-27-9
Idebenone

Conditions

Conditions	Yield
With sodium carbonate In methanol; water at 25℃; for 20h;	80%
With water; sodium carbonate In methanol at 0℃; for 36h;	61%
With hydrogenchloride; sodium chloride In methanol

: 3669-80-5
11-hydroxyundecanoic acid

: 605-94-7
2,3-Dimethoxy-5-methyl-1,4-benzoquinone

: 58186-27-9
Idebenone

Conditions

Conditions	Yield
With dihydrogen peroxide; oxygen In water; acetone at 75℃; Catalytic behavior; Reagent/catalyst; Temperature;	80%
With dipotassium peroxodisulfate; oxygen; silver nitrate In water; acetonitrile at 80℃; for 4h; Catalytic behavior; Reagent/catalyst; Solvent;	80%
With dipotassium peroxodisulfate; silver nitrate In water; acetonitrile at 80℃; for 4h;	75%
Stage #1: 11-hydroxyundecanoic acid; 2,3-Dimethoxy-5-methyl-1,4-benzoquinone With silver nitrate In water; acetonitrile Stage #2: With dipotassium peroxodisulfate In water; acetonitrile at 75℃; for 3h; Solvent; Reagent/catalyst;	65%

: C19H30O5

: 58186-27-9
Idebenone

Conditions

Conditions	Yield
Stage #1: C19H30O5 With dipotassium hydrogenphosphate; potassium hydroxylamine-N,N-disulphonate In N,N-dimethyl-formamide at 50℃; for 8h; Stage #2: With hydrogenchloride In ethanol; N,N-dimethyl-formamide at 50℃; for 8h; Stage #3: With lithium aluminium tetrahydride In N,N-dimethyl-formamide at 80℃; for 3h;	63%

: 58186-02-0
2,3-dimethoxy-5-methyl-6-(9'-methoxycarbonylnonyl)-1,4-benzoquinone

: 58186-27-9
Idebenone

Conditions

Conditions	Yield
(i) LiAlH4, (ii) aq. FeCl3; Multistep reaction;

ester of 6-(9-carboxynonyl)-2,3-dimethoxy-5-methyl-1,4-benzoquinone: ester of 6-(9-carboxynonyl)-2,3-dimethoxy-5-methyl-1,4-benzoquinone

: 58186-27-9
Idebenone

Conditions

Conditions	Yield
With lithium aluminium tetrahydride; iron(III) chloride 1.) diethyl ether, RT, 1 h, 2.) diethyl ether; Yield given. Multistep reaction;

: 14065-32-8
methyl 10-chloro-10-oxodecanoate

: 58186-27-9
Idebenone

Conditions

Conditions	Yield
Multi-step reaction with 7 steps 1: 71 percent / AlCl3 / CH2Cl2 / 24 h / Heating 2: 92 percent / LiAlH4 / tetrahydrofuran / 1 h / 0 °C 3: 96 percent / Et3N; DMAP / CH2Cl2 / 7 h / 20 °C 4: 49 percent / LiBr / dimethylformamide / 24 h / 120 °C 5: 99 percent / H2 / Pd/C / methanol / 1 h / 20 °C 6: 88 percent / CAN / acetonitrile; H2O / 0.25 h / 0 °C 7: 61 percent / Na2CO3; H2O / methanol / 36 h / 0 °C View Scheme

Yield

Multi-step reaction with 7 steps
1: 71 percent / AlCl3 / CH2Cl2 / 24 h / Heating
2: 92 percent / LiAlH4 / tetrahydrofuran / 1 h / 0 °C
3: 96 percent / Et3N; DMAP / CH2Cl2 / 7 h / 20 °C
4: 49 percent / LiBr / dimethylformamide / 24 h / 120 °C
5: 99 percent / H2 / Pd/C / methanol / 1 h / 20 °C
6: 88 percent / CAN / acetonitrile; H2O / 0.25 h / 0 °C
7: 61 percent / Na2CO3; H2O / methanol / 36 h / 0 °C
View Scheme

Raw Materials

818-88-2

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Chemistry

The Molecular Structure of Idebenone (CAS NO.58186-27-9):

Empirical Formula: C₁₉H₃₀O₅
Molecular Weight: 338.4385
IUPAC Name: 2-(10-hydroxydecyl)-5,6-dimethoxy-3-methylcyclohexa-2,5-diene-1,4-dione
Appearance: Yellow-Orange Crystalline Solid
Nominal Mass: 338 Da
Average Mass: 338.4385 Da
Monoisotopic Mass: 338.209324 Da
Index of Refraction: 1.502
Molar Refractivity: 92.13 cm³
Molar Volume: 312 cm³
Surface Tension: 41 dyne/cm
Density: 1.08 g/cm³
Flash Point: 170.1 °C
Enthalpy of Vaporization: 88.13 kJ/mol
Boiling Point: 497.3 °C at 760 mmHg
Melting Point: 52-550 °C
Vapour Pressure: 5.67E-12 mmHg at 25°C
Storage temp: Room temp
Product Categories: Anthraquinones, Hydroquinones and Quinones;Cnbio;Intermediates & Fine Chemicals;Pharmaceuticals
InChI
InChI=1/C19H30O5/c1-14-15(12-10-8-6-4-5-7-9-11-13-20)17(22)19(24-3)18(23-2)16(14)21/h20H,4-13H2,1-3H3
Smiles
C1(=C(C(C(C)=C(C1=O)CCCCCCCCCCO)=O)OC)OC

History

On July 23, 2008, Health Canada issued a Notice of Compliance under the Notice of Compliance with Conditions (NOC/c) Policy to Santhera Pharmaceuticals (Switzerland) Ltd. for the drug product Catena. The product was authorized under the NOC/c Policy on the basis of the promising nature of the clinical evidence, and the need for a confirmatory study to verify its clinical benefit. Patients should be advised of the fact that the market authorization was issued with conditions.

Uses

Idebenone (CAS NO.58186-27-9) is a synthetic analogue of coenzyme Q10 used in Europe in the treatment of vascular and degenerative diseases of the central nervous system. It has been used in the treatment of Friedreich's ataxia and also in topical applications to treat wrinkles.

Toxicity Data With Reference

Organism	Test Type	Route	Reported Dose (Normalized Dose)	Effect	Source
mammal (species unspecified)	LD50	unreported	> 1gm/kg (1000mg/kg)		Chemical and Pharmaceutical Bulletin. Vol. 39, Pg. 367, 1991.
mouse	LD50	intraperitoneal	757mg/kg (757mg/kg)	BEHAVIORAL: SOMNOLENCE (GENERAL DEPRESSED ACTIVITY) LUNGS, THORAX, OR RESPIRATION: RESPIRATORY DEPRESSION	Yakuri to Chiryo. Pharmacology and Therapeutics. Vol. 13, Pg. 3931, 1985.
mouse	LD50	oral	> 10gm/kg (10000mg/kg)		Yakuri to Chiryo. Pharmacology and Therapeutics. Vol. 13, Pg. 3931, 1985.
mouse	LD50	subcutaneous	> 10gm/kg (10000mg/kg)		Yakuri to Chiryo. Pharmacology and Therapeutics. Vol. 13, Pg. 3931, 1985.
rat	LD50	intraperitoneal	830mg/kg (830mg/kg)	BEHAVIORAL: SOMNOLENCE (GENERAL DEPRESSED ACTIVITY) LUNGS, THORAX, OR RESPIRATION: RESPIRATORY DEPRESSION	Yakuri to Chiryo. Pharmacology and Therapeutics. Vol. 13, Pg. 3931, 1985.
rat	LD50	oral	10gm/kg (10000mg/kg)	SENSE ORGANS AND SPECIAL SENSES: LACRIMATION: EYE LUNGS, THORAX, OR RESPIRATION: OTHER CHANGES GASTROINTESTINAL: "HYPERMOTILITY, DIARRHEA"	Yakuri to Chiryo. Pharmacology and Therapeutics. Vol. 13, Pg. 3931, 1985.
rat	LD50	subcutaneous	> 10gm/kg (10000mg/kg)		Yakuri to Chiryo. Pharmacology and Therapeutics. Vol. 13, Pg. 3931, 1985.

Safety Profile

Although studies in animals have shown no harmful effects, this product should not be taken during the first three months of pregnancy and during nursing, only when absolutely necessary and always under a doctor's supervision.
Hazard Codes: Irritant Xi
RTECS: GU5290000

Specification

Idebenone (CAS NO.58186-27-9) is also called as Idebenone [INN:JAN] ; 6-(10-Hydroxydecyl)-2,3-dimethoxy-5-methyl-1,4-benzoquinone ; Idebenona ; Idebenona [Spanish] ; Idebenone ; Idebenonum ; Idebenonum [Latin] ; 2,5-Cyclohexadiene-1,4-dione, 2-(10-hydroxydecyl)-5,6-dimethoxy-3-methyl- ; 2,5-Cyclohexadiene-1,4-dione, 5,6-dimethoxy-2-(10-hydroxydecyl)-3-methyl- ; 2-(10-Hydroxydecyl)-5,6-dimethoxy-3-methyl-p-benzoquinone .It is an organic compound of the quinone family and promoted commercially as a synthetic analog of coenzyme Q10 (CoQ₁₀).