58186-27-9

Basic information

• Product Name: CV-2619
• Synonyms: 2,3-Dimethoxy-6-(10-hydroxydecyl)-5-methyl-1,4-benzoquinone;Avan;Daruma;Mnesis;IDEBENONE(PATENTED-NOSUPPLY);5,6-Dimethoxy-2-(10-hydroxydecyl)-3-methyl-1,4-benzoquinone;5,6-dimethoxy-2-(10-hydroxydecyl)-3-methyl-5-cyclohexadiene-1,4-dione;cv 2619 idebenone
• CAS NO: 58186-27-9
• Molecular Formula: C₁₉H₃₀O₅
• Molecular Weight: 338.44
• EINECS: 1308068-626-2
• Product Categories: Anthraquinones, Hydroquinones and Quinones;Cnbio;Intermediates & Fine Chemicals;Pharmaceuticals;Aromatics;API;Other APIs;AP
• Mol File: 58186-27-9.mol

Chemical Properties

• Melting Point: 52-550C
• Boiling Point: 497.3 °C at 760 mmHg
• Flash Point: 170.1 °C
• Appearance: Yellow-orange crystalline powder
• Density: 1.08 g/cm³
• Vapor Pressure: 5.67E-12mmHg at 25°C
• Refractive Index: 1.502
• Storage Temp.: Room temp
• Solubility: Soluble in DMSO (up to 25 mg/ml).
• PKA: 15.20±0.10(Predicted)
• Stability: Stable for 1 year from date of purchase as supplied. Solutions in DMSO may be stored at -20°C for up to 3 months.
• Merck: 14,4888
• CAS DataBase Reference: CV-2619(CAS DataBase Reference)
• NIST Chemistry Reference: CV-2619(58186-27-9)
• EPA Substance Registry System: CV-2619(58186-27-9)

Safety Data

• Hazard Codes: Xi
• WGK Germany: 3
• RTECS: GU5290000
• Hazardous Substances Data: 58186-27-9(Hazardous Substances Data)

Usage

Uses

Used in Pharmaceutical Industry:
Idebenone is used as a drug for the treatment of cognitive defects, such as Alzheimer's disease and Friedreich's ataxia, for its positive effects on cardiac hypertrophy and neurological function.
Used in Skincare Industry:
Idebenone is used as an antioxidant for protecting the skin from free-radical attacks, improving intrinsic and extrinsic skin damage caused by free-radical formation. Its smaller molecular structure allows it to penetrate the skin and cellular membrane, leading to visible improvement in photodamaged skin, reduced skin roughness and dryness, decreased fine lines and wrinkles, and increased skin hydration. Additionally, idebenone helps improve hyperpigmentation due to its molecular structure similarity to hydroquinone, with some increase in dermal collagen also confirmed.
Used in Health-related Applications:
Idebenone has been used for addressing health-related problems such as Alzheimer's disease and heart disease.

Originator

Takeda (Japan)

Biological Activity

Antioxidant and neuroprotective agent. Protects mitochondrial membranes against lipid peroxidation and blocks glutamate neurotoxicity in vitro and in vivo . Inhibits apoptosis of astrocytes via increased NGF production.

Biochem/physiol Actions

Idebenone is used in the treatment of visual impairment in adolescents and adults with Leber′s hereditary optic neuropathy (LHON). It serves as an antioxidant. It helps to guard the heart muscle against oxidative stress. A short-chain Coenzyme Q analog that enhances superoxide formation, presumably by mediating electron transfer from N2 to oxygen.

References

1) Zs-Nagy (1990) Chemistry, toxicology, pharmacology and pharmacokinetics of idebenone: a review; Gerontol. Geriatr., 11, 1772) Civenni et al. (1999) Inhibitory effect of the neuroprotetive agent idebenone on arachidonic acid metabolism in astrocytes; Eur. J. Pharmacol., 370 1613) Takuma et al. (2000) CV-2619 protects cultured astrocytes against reperfusion injury via nerve growth factor production; Eur. J. Pharmacol., 406 3334) Gerhardt et al. (2011) Idebenone and resveratrol extend lifespan and improve motor function of HtrA2 knockout mice; PloS One, 6 e28855

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

Synthetic route

10-(2,3,4-trimethoxy-6-methylphenyl)decan-1-ol (1286209-74-2) → Idebenone (58186-27-9)

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 + 6-(10-hydroxydecyl)-2,3-dimethoxy-5-methylphenol (77712-29-9) → Idebenone (58186-27-9)

Conditions	Yield
In methanol; water	96.9%

6-(10-hydroxydecyl)-2,3-dimethoxy-5-methylphenol (77712-29-9) → Idebenone (58186-27-9)

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;

2,3-dimethoxy-6-methyl-5-benzyloxydecyl-p-benzoquinone (1251831-79-4) → Idebenone (58186-27-9)

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%

2,3-dimethoxy-5-methyl-6-(10'-acetoxydecyl)-1,4-benzoquinone (58186-28-0) → Idebenone (58186-27-9)

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

11-hydroxyundecanoic acid (3669-80-5) + 2,3-Dimethoxy-5-methyl-1,4-benzoquinone (605-94-7) → Idebenone (58186-27-9)

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 → Idebenone (58186-27-9)

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%

2,3-dimethoxy-5-methyl-6-(9'-methoxycarbonylnonyl)-1,4-benzoquinone (58186-02-0) → Idebenone (58186-27-9)

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

ester of 6-(9-carboxynonyl)-2,3-dimethoxy-5-methyl-1,4-benzoquinone → Idebenone (58186-27-9)

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

methyl 10-chloro-10-oxodecanoate (14065-32-8) → Idebenone (58186-27-9)

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

sebacic acid mono methyl ester (818-88-2) → Idebenone (58186-27-9)

Conditions

Yield

Multi-step reaction with 8 steps 1: thionyl chloride 2: 71 percent / AlCl3 / CH2Cl2 / 24 h / Heating 3: 92 percent / LiAlH4 / tetrahydrofuran / 1 h / 0 °C 4: 96 percent / Et3N; DMAP / CH2Cl2 / 7 h / 20 °C 5: 49 percent / LiBr / dimethylformamide / 24 h / 120 °C 6: 99 percent / H2 / Pd/C / methanol / 1 h / 20 °C 7: 88 percent / CAN / acetonitrile; H2O / 0.25 h / 0 °C 8: 61 percent / Na2CO3; H2O / methanol / 36 h / 0 °C View Scheme

1-(2,3,4,5-tetramethoxy-6-methylphenyl)-1,10-decenediol (374622-25-0) → Idebenone (58186-27-9)

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

methyl 10-(2,3,4,5-tetramethoxy-6-methylphenyl)-10-undecenoate (374622-17-0) → Idebenone (58186-27-9)

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

10-(2,3,4,5-tetramethoxy-6-methylphenyl)-9-decenylacetate → Idebenone (58186-27-9)

Conditions	Yield
Multi-step reaction with 3 steps 1: 99 percent / H2 / Pd/C / methanol / 1 h / 20 °C 2: 88 percent / CAN / acetonitrile; H2O / 0.25 h / 0 °C 3: 61 percent / Na2CO3; H2O / methanol / 36 h / 0 °C View Scheme

10-(2,3,4,5-tetramethoxy-6-methylphenyl)decylacetate (374622-20-5) → Idebenone (58186-27-9)

Conditions	Yield
Multi-step reaction with 2 steps 1: 88 percent / CAN / acetonitrile; H2O / 0.25 h / 0 °C 2: 61 percent / Na2CO3; H2O / methanol / 36 h / 0 °C View Scheme

10-methylcarbonyloxy-1-(2,3,4,5-tetramethoxy-6-methylphenyl)decylacetate (374622-18-1) → Idebenone (58186-27-9)

Conditions	Yield
Multi-step reaction with 4 steps 1: 49 percent / LiBr / dimethylformamide / 24 h / 120 °C 2: 99 percent / H2 / Pd/C / methanol / 1 h / 20 °C 3: 88 percent / CAN / acetonitrile; H2O / 0.25 h / 0 °C 4: 61 percent / Na2CO3; H2O / methanol / 36 h / 0 °C View Scheme

methyl 10-(2'-hydroxy-3',4'-dimethoxy-6'-methylphenyl)decanoate (58185-89-0) → Idebenone (58186-27-9)

Conditions	Yield
Multi-step reaction with 2 steps 1: LiAlH4 / tetrahydrofuran; diethyl ether / 1 h / Ambient temperature 2: 67 percent / ON(SO3K)2 / aq. NaOH / 1 h / Ambient temperature View Scheme

methyl 9-(2'-hydroxy-3',4'-dimethoxy-6'-methylbenzoyl)nonanoate (58185-88-9) → Idebenone (58186-27-9)

Conditions	Yield
Multi-step reaction with 3 steps 1: 1.) NaBH4, 2.) H2 / 2.) Pd/C 2: LiAlH4 / tetrahydrofuran; diethyl ether / 1 h / Ambient temperature 3: 67 percent / ON(SO3K)2 / aq. NaOH / 1 h / Ambient temperature View Scheme
Multi-step reaction with 2 steps 1: potassium dihydrogenphosphate; potassium nitrososulfonate 2: (i) LiAlH4, (ii) aq. FeCl3 View Scheme

9-bromononan-1-ol (55362-80-6) → Idebenone (58186-27-9)

Conditions	Yield
Multi-step reaction with 9 steps 2: 95 percent / dimethylsulfoxide / 15 h / 80 °C 3: 86 percent / NaOH, 3N HCl / ethanol / 19 h / Heating 4: PCl5 / CH2Cl2 / 2 h / 25 °C 5: 44 percent / AlCl3 / 1,2-dichloro-ethane / 72 h / 20 °C 6: 79 percent / NaOH / methanol / 2 h / Ambient temperature 7: H2, 70percent HClO4 / 5percent Pd-C / 24 h / Ambient temperature 8: NaOH / methanol / 24 h / 5 °C 9: O2 / salcomine / dimethylformamide / Ambient temperature; reaction time, additive View Scheme
Multi-step reaction with 9 steps 2: 95 percent / dimethylsulfoxide / 15 h / 80 °C 3: 86 percent / NaOH, 3N HCl / ethanol / 19 h / Heating 4: PCl5 / CH2Cl2 / 2 h / 25 °C 5: 44 percent / AlCl3 / 1,2-dichloro-ethane / 72 h / 20 °C 6: 79 percent / NaOH / methanol / 2 h / Ambient temperature 7: H2, 70percent HClO4 / 5percent Pd-C / 24 h / Ambient temperature 8: NaOH / methanol / 24 h / 5 °C 9: O2 / salcomine / dimethylformamide / Ambient temperature; reaction time, additive View Scheme
Multi-step reaction with 9 steps 2: 95 percent / dimethylsulfoxide / 15 h / 80 °C 3: 86 percent / NaOH, 3N HCl / ethanol / 19 h / Heating 4: PCl5 / CH2Cl2 / 2 h / 25 °C 5: AlCl3 / 1,2-dichloro-ethane / 5 degC, 2 h; 20 degC, 70 h 6: 79 percent / NaOH / methanol / 2 h / Ambient temperature 7: H2, 70percent HClO4 / 5percent Pd-C / 24 h / Ambient temperature 8: NaOH / methanol / 24 h / 5 °C 9: O2 / salcomine / dimethylformamide / Ambient temperature; reaction time, additive View Scheme
Multi-step reaction with 9 steps 2: 95 percent / dimethylsulfoxide / 15 h / 80 °C 3: 86 percent / NaOH, 3N HCl / ethanol / 19 h / Heating 4: PCl5 / CH2Cl2 / 2 h / 25 °C 5: 29 percent / AlCl3 / 1,2-dichloro-ethane / 72 h / 20 °C 6: 79 percent / NaOH / methanol / 2 h / Ambient temperature 7: H2, 70percent HClO4 / 5percent Pd-C / 24 h / Ambient temperature 8: NaOH / methanol / 24 h / 5 °C 9: O2 / salcomine / dimethylformamide / Ambient temperature; reaction time, additive View Scheme

9-bromononyl acetate (53596-82-0) → Idebenone (58186-27-9)

Conditions	Yield
Multi-step reaction with 8 steps 1: 95 percent / dimethylsulfoxide / 15 h / 80 °C 2: 86 percent / NaOH, 3N HCl / ethanol / 19 h / Heating 3: PCl5 / CH2Cl2 / 2 h / 25 °C 4: 44 percent / AlCl3 / 1,2-dichloro-ethane / 72 h / 20 °C 5: 79 percent / NaOH / methanol / 2 h / Ambient temperature 6: H2, 70percent HClO4 / 5percent Pd-C / 24 h / Ambient temperature 7: NaOH / methanol / 24 h / 5 °C 8: O2 / salcomine / dimethylformamide / Ambient temperature; reaction time, additive View Scheme
Multi-step reaction with 8 steps 1: 95 percent / dimethylsulfoxide / 15 h / 80 °C 2: 86 percent / NaOH, 3N HCl / ethanol / 19 h / Heating 3: PCl5 / CH2Cl2 / 2 h / 25 °C 4: 44 percent / AlCl3 / 1,2-dichloro-ethane / 72 h / 20 °C 5: 79 percent / NaOH / methanol / 2 h / Ambient temperature 6: H2, 70percent HClO4 / 5percent Pd-C / 24 h / Ambient temperature 7: NaOH / methanol / 24 h / 5 °C 8: O2 / salcomine / dimethylformamide / Ambient temperature; reaction time, additive View Scheme
Multi-step reaction with 8 steps 1: 95 percent / dimethylsulfoxide / 15 h / 80 °C 2: 86 percent / NaOH, 3N HCl / ethanol / 19 h / Heating 3: PCl5 / CH2Cl2 / 2 h / 25 °C 4: AlCl3 / 1,2-dichloro-ethane / 5 degC, 2 h; 20 degC, 70 h 5: 79 percent / NaOH / methanol / 2 h / Ambient temperature 6: H2, 70percent HClO4 / 5percent Pd-C / 24 h / Ambient temperature 7: NaOH / methanol / 24 h / 5 °C 8: O2 / salcomine / dimethylformamide / Ambient temperature; reaction time, additive View Scheme
Multi-step reaction with 8 steps 1: 95 percent / dimethylsulfoxide / 15 h / 80 °C 2: 86 percent / NaOH, 3N HCl / ethanol / 19 h / Heating 3: PCl5 / CH2Cl2 / 2 h / 25 °C 4: 29 percent / AlCl3 / 1,2-dichloro-ethane / 72 h / 20 °C 5: 79 percent / NaOH / methanol / 2 h / Ambient temperature 6: H2, 70percent HClO4 / 5percent Pd-C / 24 h / Ambient temperature 7: NaOH / methanol / 24 h / 5 °C 8: O2 / salcomine / dimethylformamide / Ambient temperature; reaction time, additive View Scheme

methyl 10-hydroxydecanoate (2640-94-0) → Idebenone (58186-27-9)

Conditions	Yield
Multi-step reaction with 7 steps 1: 1.) NaOH / p-TsOH / 1.) MeOH, reflux, 3 h; 2.) 60 degC, 2 h 2: PCl5 / CH2Cl2 / 2 h / 25 °C 3: 44 percent / AlCl3 / 1,2-dichloro-ethane / 72 h / 20 °C 4: 79 percent / NaOH / methanol / 2 h / Ambient temperature 5: H2, 70percent HClO4 / 5percent Pd-C / 24 h / Ambient temperature 6: NaOH / methanol / 24 h / 5 °C 7: O2 / salcomine / dimethylformamide / Ambient temperature; reaction time, additive View Scheme
Multi-step reaction with 7 steps 1: 1.) NaOH / p-TsOH / 1.) MeOH, reflux, 3 h; 2.) 60 degC, 2 h 2: PCl5 / CH2Cl2 / 2 h / 25 °C 3: 44 percent / AlCl3 / 1,2-dichloro-ethane / 72 h / 20 °C 4: 79 percent / NaOH / methanol / 2 h / Ambient temperature 5: H2, 70percent HClO4 / 5percent Pd-C / 24 h / Ambient temperature 6: NaOH / methanol / 24 h / 5 °C 7: O2 / salcomine / dimethylformamide / Ambient temperature; reaction time, additive View Scheme
Multi-step reaction with 7 steps 1: 1.) NaOH / p-TsOH / 1.) MeOH, reflux, 3 h; 2.) 60 degC, 2 h 2: PCl5 / CH2Cl2 / 2 h / 25 °C 3: AlCl3 / 1,2-dichloro-ethane / 5 degC, 2 h; 20 degC, 70 h 4: 79 percent / NaOH / methanol / 2 h / Ambient temperature 5: H2, 70percent HClO4 / 5percent Pd-C / 24 h / Ambient temperature 6: NaOH / methanol / 24 h / 5 °C 7: O2 / salcomine / dimethylformamide / Ambient temperature; reaction time, additive View Scheme
Multi-step reaction with 7 steps 1: 1.) NaOH / p-TsOH / 1.) MeOH, reflux, 3 h; 2.) 60 degC, 2 h 2: PCl5 / CH2Cl2 / 2 h / 25 °C 3: 29 percent / AlCl3 / 1,2-dichloro-ethane / 72 h / 20 °C 4: 79 percent / NaOH / methanol / 2 h / Ambient temperature 5: H2, 70percent HClO4 / 5percent Pd-C / 24 h / Ambient temperature 6: NaOH / methanol / 24 h / 5 °C 7: O2 / salcomine / dimethylformamide / Ambient temperature; reaction time, additive View Scheme

10-acetoxydecanoic acid (92038-37-4) → Idebenone (58186-27-9)

Conditions	Yield
Multi-step reaction with 6 steps 1: PCl5 / CH2Cl2 / 2 h / 25 °C 2: 44 percent / AlCl3 / 1,2-dichloro-ethane / 72 h / 20 °C 3: 79 percent / NaOH / methanol / 2 h / Ambient temperature 4: H2, 70percent HClO4 / 5percent Pd-C / 24 h / Ambient temperature 5: NaOH / methanol / 24 h / 5 °C 6: O2 / salcomine / dimethylformamide / Ambient temperature; reaction time, additive View Scheme
Multi-step reaction with 6 steps 1: PCl5 / CH2Cl2 / 2 h / 25 °C 2: 44 percent / AlCl3 / 1,2-dichloro-ethane / 72 h / 20 °C 3: 79 percent / NaOH / methanol / 2 h / Ambient temperature 4: H2, 70percent HClO4 / 5percent Pd-C / 24 h / Ambient temperature 5: NaOH / methanol / 24 h / 5 °C 6: O2 / salcomine / dimethylformamide / Ambient temperature; reaction time, additive View Scheme
Multi-step reaction with 6 steps 1: PCl5 / CH2Cl2 / 2 h / 25 °C 2: AlCl3 / 1,2-dichloro-ethane / 5 degC, 2 h; 20 degC, 70 h 3: 79 percent / NaOH / methanol / 2 h / Ambient temperature 4: H2, 70percent HClO4 / 5percent Pd-C / 24 h / Ambient temperature 5: NaOH / methanol / 24 h / 5 °C 6: O2 / salcomine / dimethylformamide / Ambient temperature; reaction time, additive View Scheme
Multi-step reaction with 6 steps 1: PCl5 / CH2Cl2 / 2 h / 25 °C 2: 29 percent / AlCl3 / 1,2-dichloro-ethane / 72 h / 20 °C 3: 79 percent / NaOH / methanol / 2 h / Ambient temperature 4: H2, 70percent HClO4 / 5percent Pd-C / 24 h / Ambient temperature 5: NaOH / methanol / 24 h / 5 °C 6: O2 / salcomine / dimethylformamide / Ambient temperature; reaction time, additive View Scheme

10-acetoxydecanoyl chloride (104967-12-6) → Idebenone (58186-27-9)

Conditions	Yield
Multi-step reaction with 5 steps 1: 44 percent / AlCl3 / 1,2-dichloro-ethane / 72 h / 20 °C 2: 79 percent / NaOH / methanol / 2 h / Ambient temperature 3: H2, 70percent HClO4 / 5percent Pd-C / 24 h / Ambient temperature 4: NaOH / methanol / 24 h / 5 °C 5: O2 / salcomine / dimethylformamide / Ambient temperature; reaction time, additive View Scheme
Multi-step reaction with 5 steps 1: 44 percent / AlCl3 / 1,2-dichloro-ethane / 72 h / 20 °C 2: 79 percent / NaOH / methanol / 2 h / Ambient temperature 3: H2, 70percent HClO4 / 5percent Pd-C / 24 h / Ambient temperature 4: NaOH / methanol / 24 h / 5 °C 5: O2 / salcomine / dimethylformamide / Ambient temperature; reaction time, additive View Scheme
Multi-step reaction with 5 steps 1: AlCl3 / 1,2-dichloro-ethane / 5 degC, 2 h; 20 degC, 70 h 2: 79 percent / NaOH / methanol / 2 h / Ambient temperature 3: H2, 70percent HClO4 / 5percent Pd-C / 24 h / Ambient temperature 4: NaOH / methanol / 24 h / 5 °C 5: O2 / salcomine / dimethylformamide / Ambient temperature; reaction time, additive View Scheme
Multi-step reaction with 5 steps 1: 29 percent / AlCl3 / 1,2-dichloro-ethane / 72 h / 20 °C 2: 79 percent / NaOH / methanol / 2 h / Ambient temperature 3: H2, 70percent HClO4 / 5percent Pd-C / 24 h / Ambient temperature 4: NaOH / methanol / 24 h / 5 °C 5: O2 / salcomine / dimethylformamide / Ambient temperature; reaction time, additive View Scheme
Multi-step reaction with 2 steps 1.1: aluminum (III) chloride / dichloromethane / 72 h / 4 °C 1.2: 8 h / 25 °C 2.1: dipotassium hydrogenphosphate; potassium hydroxylamine-N,N-disulphonate / N,N-dimethyl-formamide / 8 h / 50 °C 2.2: 8 h / 50 °C 2.3: 3 h / 80 °C View Scheme

9-acetoxydecanenitrile (104967-00-2) → Idebenone (58186-27-9)

Conditions	Yield
Multi-step reaction with 7 steps 1: 86 percent / NaOH, 3N HCl / ethanol / 19 h / Heating 2: PCl5 / CH2Cl2 / 2 h / 25 °C 3: 44 percent / AlCl3 / 1,2-dichloro-ethane / 72 h / 20 °C 4: 79 percent / NaOH / methanol / 2 h / Ambient temperature 5: H2, 70percent HClO4 / 5percent Pd-C / 24 h / Ambient temperature 6: NaOH / methanol / 24 h / 5 °C 7: O2 / salcomine / dimethylformamide / Ambient temperature; reaction time, additive View Scheme
Multi-step reaction with 7 steps 1: 86 percent / NaOH, 3N HCl / ethanol / 19 h / Heating 2: PCl5 / CH2Cl2 / 2 h / 25 °C 3: 44 percent / AlCl3 / 1,2-dichloro-ethane / 72 h / 20 °C 4: 79 percent / NaOH / methanol / 2 h / Ambient temperature 5: H2, 70percent HClO4 / 5percent Pd-C / 24 h / Ambient temperature 6: NaOH / methanol / 24 h / 5 °C 7: O2 / salcomine / dimethylformamide / Ambient temperature; reaction time, additive View Scheme
Multi-step reaction with 7 steps 1: 86 percent / NaOH, 3N HCl / ethanol / 19 h / Heating 2: PCl5 / CH2Cl2 / 2 h / 25 °C 3: AlCl3 / 1,2-dichloro-ethane / 5 degC, 2 h; 20 degC, 70 h 4: 79 percent / NaOH / methanol / 2 h / Ambient temperature 5: H2, 70percent HClO4 / 5percent Pd-C / 24 h / Ambient temperature 6: NaOH / methanol / 24 h / 5 °C 7: O2 / salcomine / dimethylformamide / Ambient temperature; reaction time, additive View Scheme
Multi-step reaction with 7 steps 1: 86 percent / NaOH, 3N HCl / ethanol / 19 h / Heating 2: PCl5 / CH2Cl2 / 2 h / 25 °C 3: 29 percent / AlCl3 / 1,2-dichloro-ethane / 72 h / 20 °C 4: 79 percent / NaOH / methanol / 2 h / Ambient temperature 5: H2, 70percent HClO4 / 5percent Pd-C / 24 h / Ambient temperature 6: NaOH / methanol / 24 h / 5 °C 7: O2 / salcomine / dimethylformamide / Ambient temperature; reaction time, additive View Scheme

6-(10-hydroxy-1-oxodecyl)-2,3-dimethoxy-5-methylphenol (104966-97-4) → Idebenone (58186-27-9)

Conditions	Yield
Multi-step reaction with 3 steps 1: H2, 70percent HClO4 / 5percent Pd-C / 24 h / Ambient temperature 2: NaOH / methanol / 24 h / 5 °C 3: O2 / salcomine / dimethylformamide / Ambient temperature; reaction time, additive View Scheme

6-(10-acetoxydecyl)-2,3-dimethoxy-5-methylphenol (77712-30-2) → Idebenone (58186-27-9)

Conditions	Yield
Multi-step reaction with 2 steps 1: NaOH / methanol / 24 h / 5 °C 2: O2 / salcomine / dimethylformamide / Ambient temperature; reaction time, additive View Scheme

Acetic acid 10-(2-hydroxy-3,4-dimethoxy-6-methyl-phenyl)-10-oxo-decyl ester (104966-92-9) → Idebenone (58186-27-9)

Conditions	Yield
Multi-step reaction with 4 steps 1: 79 percent / NaOH / methanol / 2 h / Ambient temperature 2: H2, 70percent HClO4 / 5percent Pd-C / 24 h / Ambient temperature 3: NaOH / methanol / 24 h / 5 °C 4: O2 / salcomine / dimethylformamide / Ambient temperature; reaction time, additive View Scheme

9-ethoxycarbonylnonanoic acid chloride (6946-46-9) → Idebenone (58186-27-9)

Conditions	Yield
Multi-step reaction with 4 steps 1: (i) AlCl3, (ii) (hydrolysis) 2: hydrogenchloride 3: potassium dihydrogenphosphate; potassium nitrososulfonate 4: (i) LiAlH4, (ii) aq. FeCl3 View Scheme

3,4,5-trimethoxytoluene (6443-69-2) → Idebenone (58186-27-9)

Conditions	Yield
Multi-step reaction with 5 steps 1.1: nitric acid; potassium bromide / acetic anhydride / 1.25 h / 20 °C 2.1: palladium diacetate; triethylamine; triphenylphosphine / 72 h / 120 °C / Inert atmosphere 2.2: 3 h / 25 °C 3.1: iodine / 1 h / 25 °C 4.1: dihydrogen peroxide; toluene-4-sulfonic acid / acetic acid / 0.42 h / 75 °C 5.1: sodium carbonate / methanol; water / 20 h / 25 °C View Scheme
Multi-step reaction with 4 steps 1: (i) AlCl3, (ii) (hydrolysis) 2: hydrogenchloride 3: potassium dihydrogenphosphate; potassium nitrososulfonate 4: (i) LiAlH4, (ii) aq. FeCl3 View Scheme

9-(2-hydroxy-3,4-dimethoxy-6-methylbenzoyl)nonanoic acid (58185-79-8) → Idebenone (58186-27-9)

Conditions	Yield
Multi-step reaction with 3 steps 1: hydrogenchloride 2: potassium dihydrogenphosphate; potassium nitrososulfonate 3: (i) LiAlH4, (ii) aq. FeCl3 View Scheme

nonanoic acid (112-05-0) + Idebenone (58186-27-9) → 10-(4,5-dimethoxy-2-methyl-3,6-dioxocyclohexa-1,4-dien-1-yl)decyl nonanoate

Conditions	Yield
With dicyclohexyl-carbodiimide In tetrahydrofuran for 24h; Reflux;	100%

Idebenone (58186-27-9) + [bromo(difluoro)methyl](trimethyl)silane (115262-01-6) → 2-(10-(difluoromethoxy)decyl)-5,6-dimethoxy-3-methylcyclohexa-2,5-diene-1,4-dione

Conditions	Yield
With potassium hydrogen difluoride In dichloromethane; water at 20℃; for 10h; Reagent/catalyst;	98%

Idebenone (58186-27-9) + 1-hexadecylcarboxylic acid (57-10-3) → C35H60O6

Conditions	Yield
With dicyclohexyl-carbodiimide In tetrahydrofuran for 24h; Reflux;	97.4%

Idebenone (58186-27-9) → 2-(10-iododecyl)-5,6-dimethoxy-3-methylcyclohexa-2,5-diene-1,4-dione

Conditions	Yield
With 1H-imidazole; iodine; triphenylphosphine In dichloromethane at 0 - 20℃; for 4h; Inert atmosphere;	96%

Octanoic acid (124-07-2) + Idebenone (58186-27-9) → Idebenone octanoate (1177393-72-4)

Conditions	Yield
With novozym 435 In toluene at 20℃; for 48h; 4A molecular sieves;	92%
In ethyl acetate; toluene	630 mg (92%)
silica gel In ethyl acetate; toluene	630 mg (92%)

Idebenone (58186-27-9) + methanesulfonyl chloride (124-63-0) → 10-(4,5-dimethoxy-2-methyl-3,6-dioxocyclohexa-1,4-dienyl)decyl methanesulfonate (845959-53-7)

Conditions	Yield
With dmap; triethylamine In dichloromethane at 0 - 20℃; for 16h;	91%
With dmap; triethylamine In dichloromethane at 0 - 20℃; for 16h;	91%
With triethylamine In dichloromethane at 10 - 15℃; for 1.5 - 1.75h;

Idebenone (58186-27-9) + acetic anhydride (108-24-7) → 2,3-dimethoxy-5-methyl-6-(10'-acetoxydecyl)-1,4-benzoquinone (58186-28-0)

Conditions	Yield
With pyridine In dichloromethane for 15h; Ambient temperature;	90.7%
In pyridine
With pyridine

1-decanoic acid (334-48-5) + Idebenone (58186-27-9) → 10-(4,5-dimethoxy-2-methyl-3,6-dioxocyclohexa-1,4-dien-1-yl)decyl decanoate

Conditions	Yield
With dicyclohexyl-carbodiimide In tetrahydrofuran for 24h; Reflux;	90.2%

valproic acid (99-66-1) + Idebenone (58186-27-9) → C27H44O6

Conditions	Yield
With dicyclohexyl-carbodiimide In tetrahydrofuran for 24h; Reflux;	90.2%

linoleic acid (60-33-3) + Idebenone (58186-27-9) → Idebenone Linoleate (1177393-70-2)

Conditions	Yield
With novozym 435 In toluene at 20℃; for 48h; 4A molecular sieves;	87%

Idebenone (58186-27-9) + Ag(1+)*CF3S(1-)*(x)C2H3N → 2,3-dimethoxy-5-methyl-6-(10-((trifluoromethyl)thio)decyl)cyclohexa-2,5-diene-1,4-dione

Conditions	Yield
With 1,2-Diiodoethane; tetra-(n-butyl)ammonium iodide; Diphenylvinylphosphine In N,N-dimethyl-formamide; acetonitrile at 80℃; for 0.25h; Inert atmosphere; Sealed tube;	86%

Idebenone (58186-27-9) → 10-(4,5-dimethoxy-2-methyl-3,6-dioxocyclohexa-1,4-dienyl)decanal (89048-27-1)

Conditions	Yield
Stage #1: Idebenone With oxalyl dichloride; dimethyl sulfoxide In dichloromethane for 0.166667h; Stage #2: With triethylamine In dichloromethane for 1h;	84%
With oxalyl dichloride; triethylamine In dichloromethane; dimethyl sulfoxide at -78℃; for 1.5h;	84%
With sodium acetate; pyridinium chlorochromate In dichloromethane for 2.5h; Ambient temperature;	38.7%
With Dess-Martin periodane In dichloromethane at 0℃; for 4h; Inert atmosphere;

Idebenone (58186-27-9) → 10-(2,3-Dimethoxy-5-methyl-1,4-benzoquinon-6-yl)decanoic acid (58185-99-2)

Conditions	Yield
With Jones reagent In acetone	83%
With phosphate buffer; D-glucose; rat liver slices at 37℃; for 1h; incubation, pH=7.4;
With Jones reagent In acetone at 0℃; for 0.333333h;

oxalyl dichloride (79-37-8) + Idebenone (58186-27-9) → C40H58O12

Conditions	Yield
With N-ethyl-N,N-diisopropylamine In dichloromethane at 25℃; for 3h; Inert atmosphere; Cooling with ice;	83%

Idebenone (58186-27-9) + trolox (56305-04-5, 53188-07-1) → 3,4-dihydro-6-hydroxy-2,5,7,8-tetramethyl-2H-1-benzopyran-2-carboxylic acid 10-(4,5-dimethoxy-2-methyl-3,6-dioxo-1,4-cyclohexadien-1-yl)decyl ester

Conditions	Yield
With dmap; dicyclohexyl-carbodiimide In acetonitrile at 0 - 20℃; for 1.5h; Inert atmosphere;	82%

Idebenone (58186-27-9) → 2-(10-fluorodecyl)-5,6-dimethoxy-3-methylcyclohexa-2,5-diene-1,4-dione

Conditions	Yield
With tetrabutylammonium tetra(tert-butyl alcohol) coordinate fluoride; N-tosyl-4-chlorobenzenesulfonimidoyl fluoride; 1,8-diazabicyclo[5.4.0]undec-7-ene In toluene at 20℃; for 0.5h; Sealed tube;	82%

lauric acid (143-07-7) + Idebenone (58186-27-9) → 10-(4,5-dimethoxy-2-methyl-3,6-dioxocyclohexa-1,4-dien-1-yl)decyl dodecanoate

Conditions	Yield
With dicyclohexyl-carbodiimide In tetrahydrofuran for 24h; Reflux;	81.1%

Idebenone (58186-27-9) + trimethyl(pentafluoroethyl)silane (124898-13-1) → 2,3-dimethoxy-5-methyl-6-(10-(perfluoroethoxy)decyl)cyclohexa-2,5-diene-1,4-dione

Conditions	Yield
With potassium fluoride; 2-fluoropyridine; silver trifluoromethanesulfonate; lithium trifluoromethanesulfonate; Selectfluor In ethyl acetate at 20℃; for 12h; Inert atmosphere;	80%

di-tert-butyl dicarbonate (24424-99-5) + Idebenone (58186-27-9) → di-tert-butyl 2-(10-hydroxydecyl)-5,6-dimethoxy-3-methyl-1,4-phenylene dicarbonate (1431987-50-6)

Conditions	Yield
With triethylamine In tetrahydrofuran at 0 - 20℃;	79%

Idebenone (58186-27-9) + C19H16ClNO4 → C38H44ClNO8

Conditions	Yield
With sulfuric acid In cyclohexane at 25 - 65℃; Reflux;	78%

Idebenone (58186-27-9) + difluoromethyl-(4-nitrophenyl) bis(carbomethoxy) methylide sulfonium ylide → 2-(10-(difluoromethoxy)decyl)-5,6-dimethoxy-3-methylcyclohexa-2,5-diene-1,4-dione

Conditions	Yield
With lithium tetrafluoroborate In dichloromethane at 30℃; for 1h;	77%

Idebenone (58186-27-9) + tetramethylammonium trifluoromethylselenate(0) (75264-92-5) → 2,3-dimethoxy-5-methyl-6-(10-((trifluoromethyl)selanyl)decyl)cyclohexa-2,5-diene-1,4-dione

Conditions	Yield
With calcium chloride In acetonitrile at 60℃; Temperature; Inert atmosphere; Sealed tube; Glovebox;	77%

Idebenone (58186-27-9) → 10-(4,5-dimethoxy-2-methyl-3,6-dioxocyclohexa-1,4-dienyl)decyl nitrate (1431986-91-2)

Conditions	Yield
With 2,6-di-tert-butyl-4-methylpyridine; trifluoromethylsulfonic anhydride; tetrabutylammonium nitrate In dichloromethane at -70℃; for 2h;	75%
With 2,6-di-tert-butyl-4-methylpyridine; trifluoromethylsulfonic anhydride; tetrabutylammonium nitrate In dichloromethane at -70℃; for 2h;	75%
Multi-step reaction with 2 steps 1: triethylamine; dmap / dichloromethane / 16 h / 0 - 20 °C 2: tetrabutylammonium nitrate; sodium nitrate / acetic acid butyl ester; acetonitrile / 18 h / 80 °C View Scheme
Multi-step reaction with 2 steps 1: dmap; triethylamine / dichloromethane / 16 h / 0 - 20 °C 2: sodium nitrate; tetrabutylammonium nitrate / acetic acid butyl ester; acetonitrile / 18 h / 80 °C View Scheme

Idebenone (58186-27-9) + (trifluoromethyl)trimethylsilane (81290-20-2) → 2,3-dimethoxy-5-methyl-6-(10-(trifluoromethoxy)decyl)cyclohexa-2,5-diene-1,4-dione

Conditions	Yield
With potassium fluoride; 2-fluoropyridine; silver trifluoromethanesulfonate; Selectfluor In ethyl acetate at 20℃; for 12h; Glovebox; Inert atmosphere;	64%

Upstream product

• 58186-02-0 2,3-dimethoxy-5-methyl-6-(9'-methoxycarbonylnonyl)-1,4-benzoquinone 
• 77712-29-9 6-(10-hydroxydecyl)-2,3-dimethoxy-5-methylphenol 
• 58186-28-0 2,3-dimethoxy-5-methyl-6-(10'-acetoxydecyl)-1,4-benzoquinone 
• 818-88-2 sebacic acid mono methyl ester 
• 374622-20-5 10-(2,3,4,5-tetramethoxy-6-methylphenyl)decylacetate 
• 374622-18-1 10-methylcarbonyloxy-1-(2,3,4,5-tetramethoxy-6-methylphenyl)decylacetate 
• 58185-89-0 methyl 10-(2'-hydroxy-3',4'-dimethoxy-6'-methylphenyl)decanoate 
• 58185-88-9 methyl 9-(2'-hydroxy-3',4'-dimethoxy-6'-methylbenzoyl)nonanoate 
• 55362-80-6 9-bromononan-1-ol 
• 53596-82-0 9-bromononyl acetate 
• 104967-12-6 10-acetoxydecanoyl chloride 
• 77712-30-2 6-(10-acetoxydecyl)-2,3-dimethoxy-5-methylphenol 
• 104966-92-9 Acetic acid 10-(2-hydroxy-3,4-dimethoxy-6-methyl-phenyl)-10-oxo-decyl ester 
• 58185-79-8 9-(2-hydroxy-3,4-dimethoxy-6-methylbenzoyl)nonanoic acid 

Downstream Products

• 58186-28-0 2,3-dimethoxy-5-methyl-6-(10'-acetoxydecyl)-1,4-benzoquinone 
• 58185-99-2 10-(2,3-Dimethoxy-5-methyl-1,4-benzoquinon-6-yl)decanoic acid 
• 116460-82-3 6-(10-hydroxydecyl)-3-methoxy-5-methyl-1,4-benzoquinone 
• 116460-81-2 6-(10-hydroxydecyl)-2-methoxy-5-methyl-1,4-benzoquinone 
• 88543-33-3 2-hydroxy-6-(10-hydroxydecyl)-3-methoxy-5-methyl-1,4-benzoquinone 
• 88543-34-4 3-hydroxy-6-(10-hydroxydecyl)-2-methoxy-5-methyl-1,4-benzoquinone 
• 89048-27-1 10-(4,5-dimethoxy-2-methyl-3,6-dioxocyclohexa-1,4-dienyl)decanal 
• 58186-26-8 2-(10-hydroxydecyl)-5,6-dimethoxy-3-methylbenzene-1,4-diol 
• 95233-55-9 6-(10-Acetoxydecyl)-2,3-dimethoxy-5-methylhydroquinone 
• 96012-40-7 10-<3,4-dimethoxy-2,5-di(methoxymethoxy)-6-methylphenyl>-1-decanol 
• 86515-60-8 10-<3,4-dimethoxy-2,5-di(methoxymethoxy)-6-methylphenyl>decanal 
• 86515-55-1 2-<10-<3,4-dimethoxy-2,5-di(methoxymethoxy)-6-methylphenyl>decyl>-3-hydroxytetracosanoic acid 
• 96012-42-9 ethyl 2-<10-<3,4-dimethoxy-2,5-di(methoxymethoxy)-6-methylphenyl>decyl>-3-hydroxytetracosanoate 
• 96022-21-8 ethyl 2-<10-<3,4-dimethoxy-2,5-di(methoxymethoxy)-6-methylphenyl>decylidene>-3-oxotetracosanoate 

Relevant articles and documents

AgNO3-catalyzed decarboxylative cross-coupling reaction: an approach to coenzyme Q

An efficient and general method for the synthesis of coenzyme Q compounds through the activation of the 1,4-benzoquinone Csp2-H bond has been developed. This C-C bond formation reaction proceeds readily in an open flask by the direct cross-coupling reaction of coenzyme Q0with commercially available aliphatic carboxylic acids utilizing AgNO3as a catalyst and K2S2O8as an oxidant in aqueous solution. This radical reaction is operationally simple and amenable to gram-scale synthesis.

Coenzyme Q compound synthesis method

The invention relates to a coenzyme Q compound synthesis method, which comprises the steps of: dissolving substituted or unsubstituted 3, 4, 5-trimethoxytoluene in an organic solvent, carrying out a reaction on the obtained solution and an oxidant aqueous solution for 1-2h at a temperature of 20-80 DEG C under the catalysis of an acid, and carrying out extraction, water washing, reduced pressure distillation and recrystallization on the obtained crude product to obtain a coenzyme Q compound. Raw materials used in the method are cheap and easy to obtain, and no toxic or harmful waste gas or waste residue is generated in the reaction process; and reaction steps are few, the operation is easy and convenient, the product yield is high, and the method is suitable for industrial large-scale production.

COMPOUND CONTAINING INDOLEACETIC ACID CORE STRUCTURE AND USE THEREOF

Disclosed are a compound as shown by the following formula 1, and a pharmaceutically acceptable salt, an ester, a hydrate and an organic solvate thereof. In the formula (1), the groups R1 to R17 are independently selected from the group consisting of hydrogen, fluorine, chlorine, bromine, iodine, C1-C8 alkyl, C1-C8 alkoxy, carbonyl, hydroxyl, amino, azido, carboxyl and C1-C8 alkylsulfinyl, respectively; and X is a carbon or nitrogen atom; Y is selected from the following groups: a single bond, C1-C8 alkylene, C6-C20 arylene and C4-C20 heteroarylene; and n is an integer from 5 to 20. Also provided in the present invention are a pharmaceutical composition containing the compound, and use thereof in the field of tumor therapy.

A preparation method of idebenone (by machine translation)

The invention relates to a preparation method of idebenone, the method comprises: to coenzyme Q0 and 11 - hydroxy undecanoic acid as the raw material, the choice of copper chloride, copper sulfate, copper acetate, silver carbonate, silver oxide, palladium chloride or palladium acetate in a metal salt as a catalyst, in the protection of the next adds oxygen oxidizing agent hydrogen peroxide, alkylation of the free radical reaction. The reaction system by extraction, water washing, drying, reduced pressure distillation, column chromatography, get the yellow needle-like crystal, 6 - (10 - hydroxyl decyl) - 2, 3 - dimethoxy - 5 - methyl - 1, 4 - benzoquinone, namely idebenone. This preparation method has a simple operation, low cost, and the yield and the like, suitable for large-scale industrial production of idebenone. (by machine translation)

Single-step synthesis of idebenone from Coenzyme Q0 via free-radical alkylation under silver catalysis

Idebenone was synthesized directly by free-radical alkylation of 2,3-dimethyl-1,4-benzoquinone (Coenzyme Q0) with commercially available 11-hydroxyundecanoic acid in the presence of potassium peroxodisulfate and silver nitrate in a mixed solvent (CH3CN-H2O, 1:1) under mild condition in good yields (65%, based on Coenzyme Q0). The reaction is operationally simple and could be used in the preparation of other biologically Coenzyme Q analogues.

Synthetic route discovery and introductory optimization of a novel process to idebenone

An environmentally benign, convenient, high yielding, and cost-effective synthesis leading to idebenone is disclosed. The synthesis includes a bromination process for the preparation of 2-bromo-3,4,5-trimethoxy-1- methylbenzene, a protocol for the Heck cross-coupling reaction using either thermal or microwave heating, olefin reduction by palladium catalyzed hydrogenation, and a green oxidation protocol with hydrogen peroxide as oxidant to achieve the benzoquinone framework. The total synthesis is composed of six steps that provide an overall yield of 20% that corresponds to a step yield of 76%.

Synthesis and characterization of mitoQ and idebenone analogues as mediators of oxygen consumption in mitochondria

Analogues of mitoQ and idebenone were synthesized to define the structural elements that support oxygen consumption in the mitochondrial respiratory chain. Eight analogues were prepared and fully characterized, then evaluated for their ability to support oxygen consumption in the mitochondrial respiratory chain. While oxygen consumption was strongly inhibited by mitoQ analogues 2-4 in a chain length-dependent manner, modification of idebenone by replacement of the quinone methoxy groups by methyl groups (analogues 6-8) reduced, but did not eliminate, oxygen consumption. Idebenone analogues 6-8 also displayed significant cytoprotective properties toward cultured mammalian cells in which glutathione had been depleted by treatment with diethyl maleate.

Esters of long-chain alcohols and preparation thereof

Disclosed are esters and a process for the preparation of the esters represented by formula 1: The process includes reacting an alcohol with a long-chain acid R2COOH or long-chain ester R2COOR4 in the presence of an organic solvent and an enzyme with or without the removal of water.

ESTERS OF LONG-CHAIN ALCOHOLS AND PREPARATION THEREOF

Disclosed is a composition and methods of treating a skin condition. The ester includes an ester and a dermatologically acceptable carrier. The ester is represented by the general formula 1: