55127-92-9

Usage

Uses

Used in Pharmaceutical Industry:
Vitamin Q is used as a dietary supplement for maintaining energy production, supporting heart health, and providing antioxidant protection against free radicals.
Used in Cosmetic Industry:
Vitamin Q is used as an ingredient in skincare products for its antioxidant properties, which help protect the skin from environmental damage and promote a youthful appearance.
Used in Food and Beverage Industry:
Vitamin Q is used as a fortifying agent in certain food and beverage products to enhance their nutritional value and support overall health and well-being.

Upstream product

• 75426-26-5 ubiquinol 
• 64634-91-9 1-[(2E,6E,10E,14E,18E,22E,26E,30E,34E)-3,7,11,15,19,23,27,31,35,39-decamethyltetraconta-2,6,10,14,18,22,26,30,34,38-decaen-1-yl]-3,4-dimethoxy-2,5-bis(methoxymethoxy)-6-methylbenzene 
• 947156-48-1 2-((2E,6E,10E,14E,18E,22E,26E,30E,34E)-3,7,11,15,19,23,27,31,35,39-Decamethyl-tetraconta-2,6,10,14,18,22,26,30,34,38-decaenyl)-5,6-dimethoxy-3-methyl-benzene-1,4-diol 
• 94828-17-8 (2'E,6'E,10'E,14'E,18'E,22'E,26'E,30'E,34'E,38'E)-1-(3',7',11',15',19',23',27',31',35',39'-decamethyltetraconta-2',6',10',14',18',22',26',30',34',38'-decaenyl)-6-methyl-2,3,4,5-tetramethoxybenzene 
• 605-94-7 2,3-Dimethoxy-5-methyl-1,4-benzoquinone 
• 68799-83-7 (all-E)-3,7,11,15,19,23,27,31,35,39-decamethyl-2,6,10,14,18,22,26,30,34,38-tetracontadecaenyl bromide 
• 70854-63-6 1,4-bis(benzyloxy)-2-{(2E,6E,10E,14E,18E,22E,26E,30E,34E)-3,7,11,15,19,23,27,31,35,39-decamethyl-5-[(4-methylphenyl)sulfonyl]tetraconta-2,6,10,14,18,22,26,30,34,38-decaenyl}-5,6-dimethoxy-3-methylbenzene 
• 13190-97-1 solanesol 
• 52610-77-2 solanesyl bromide 
• 82343-04-2 (2E)-4-(3,4-dimethoxy-2,5-bis(methoxymethoxy)-6-methylphenyl)-2-methylbut-2-en-1-ol 
• 66958-69-8 1,4-bis(benzyloxy)-2-[(2E)-4-bromo-3-methylbut-2-enyl]-5,6-dimethoxy-3-methylbenzene 
• 70854-64-7 solanesyl p-tolyl sulphone 
• 3066-90-8 2,3-dimethoxy-5-methylbenzene-1,4-diol 
• 78592-74-2 (E)-4-iodo-3-methyl-3-buten-1-ol 

Downstream Products

• 28645-33-2 Hydronbichinon-bis-methylcarbamat 
• 28527-67-5 diethoxy-CoQ₁₀ 
• 1974-58-9 2-(3,7,11,15,19,23,27,31,35,39-decamethyl-tetracontyl)-5,6-dimethoxy-3-methyl-[1,4]benzoquinone 

Relevant academic research and scientific papers

Method for synthesizing coenzyme Q10 from 5-demethoxy coenzyme Q10

The invention relates to a method for synthesizing a coenzyme Q10 from a 5-demethoxy coenzyme Q10. The method comprises the following steps of: taking the 5-demethoxy coenzyme Q10 as a raw material, and carrying out a 1,4-addition reaction, a methoxylation reaction and an oxidation reaction to finally prepare the coenzyme Q10. According to the method, the 5-demethoxy coenzyme Q10 is used as a rawmaterial, the process route is short, the yield is high, the product purity is high, the content detected by adopting HPLC (High Performance Liquid Chromatography) of a pharmacopoeia analysis method is 98% or more, and the problem of a byproduct 5-demethoxy coenzyme Q10 generated in a production fermentation process of the coenzyme Q10 is solved, thereby changing wastes into valuables.

Synthesis of coenzyme Q10

A practical synthesis of coenzyme Q10 has been developed. The route features an improved Friedel-Crafts allylation of tetramethoxytoluene with a para-chlorobenzenesulfonyl-substituted C5 allylic chloride at 40 °C. Replacement of the methyl ether protecting groups of the para-hydroquinone by methoxymethyl groups at Q1 stage proceeded efficiently, and allowed the facile final oxidation to coenzyme Q10 to occur under mild acidic conditions. The overall yield of coenzyme Q 10 from commercially available tetramethoxytoluene reached 53 % in this improved procedure. An improved synthesis gave CoQ10 in 53 % overall yield from tetramethoxytoluene through Friedel-Crafts allylation with a para-chlorobenzenesulfonyl-substituted C5 allylic chloride and a modified oxidation procedure. Copyright

Novel Intermediates, Process for Their Preparation and Process for the Preparation of Coq10 Employing the Said Novel Intermediates

The present invention relates to an improved process for the preparation of Coenzyme Q. Coenzyme Q10 or CoQ10 has the chemical name 2-[(all-trans)-3,7,11,15,19,23,27,31,35,39-decamethyl-2,6,10,14,18,22,26,30,34,38-tetracontadecaenyl]-5,6-dimethoxy-3-methyl-1,4-benzoquinone and has the formula I. The invention also provides new intermediates useful for the preparation of CoQ10 and processes for their preparation.

NOVEL INTERMEDIATES, PROCESS FOR THEIR PREPARATION AND PROCESS FOR THE PREPARATION OF COQ10 EMPLOYING THE SAID NOVEL INTERMEDIATES

The present invention relates to an improved process for the preparation of Coenzyme Q. Coenzyme QlO or CoQlO has the chemical name 2- [(all -trans)- 3, 7,l l,15,19,23,27,31,35,39-decamethyl-2, 6, 10, 14, 18, 22, 26, 30, 34, 38 - tetracontadecaenyl]-5-6-dimethoxy -3- methyl -1,4-benzoquinone and has the formula 1. The invention also provides new intermediates useful for the preparation of CoQlO and processes for their preparation.

Enhancing regiocontrol in carboaluminations of terminal alkynes. Application to the one-pot synthesis of coenzyme Q10

Two new "generations" of methodological advances are reported for the Negishi carboalumination of terminal alkynes. Use of simple, inexpensive additives that alter the Al-Zr complex formed between Me3Al and Cp2ZrCl2 give rise to an especially effective reagent mix that results in virtually complete control of regiochemistry upon carboalumination of 1-alkynes. One timely application to coenzyme Q10 is highlighted. Regioisomers from subsequent coupling, which would otherwise be very difficult to separate, are avoided.

Synthetic studies on coenzyme Q10: Part 31) - An improved C5 + C45 approach to the stereoselective synthesis of coenzyme Q10 via metal-halogen exchange strategy

An efficient and stereoselective approach to the synthesis of coenzyme Q10 is described (Scheme). The MeOCH2-protected p-hydroquinone 4 containing the C5 (E)-allyl (tert-butyl) dimethylsilyl ether moiety was obtained via a halogen-lithium exchange of the MeOCH2-proctected 2-bromo-5,6-dimethoxy-3-methylhydroquinone 2 and subsequent addition to (E)-(tBuMe2Si)-OCH 2C(Me)= CHCH2Br (3). The reductive desulfonylation of compound 8, obtained from 4 via 5-7, was successfully carried out by employing Li/EtNH2.

IMPROVED PROCESS FOR THE SYNTHESIS OF COQ10

The present invention relates to an improved process for the preparation of Coenzyme Q. Coenzyme Q10 or CoQ10 has the chemical name 2- [(all -trans)- 3, 7,l l,15,19,23,27,31,35,39-decamethyl-2, 6, 10, 14, 18, 22, 26, 30, 34, 38 - tetracontadecaenyl]-5,6-dimethoxy -3- methyl -1,4-benzoquinone and has the formula 1.

PROCESS FOR THE PREPARATION OF UBIHYDROQUINONES AND UBIQUINONES

A process for the preparation of ubihydroquinones and ubiquinones by condensation of a prenol or isoprenol with a hydroquinone or derivative thereof in the presence of 0.005 - 1.0 mol% of a catalyst which is a Broensted-acid, a Lewis-acid from the group consisting of a derivative of Bi or In or an element of group 3 of the periodic table of the elements, a heteropolyacid, an NH- or a CH-acidic compound, and optionally oxidizing the ubihydroquinone obtained.

Friedel-Crafts allylation of 2-(benzyloxy)-3,4,5-trimethoxytoluene catalysed by a metal trifluoromethanesulfonic salt: Synthesis of coenzyme Q10

In the presence of a catalytic amount of scandium triflate, 2-benzyloxy-3,4,5-trimethoxytoluene reacted with allylic derivatives 4, giving the key intermediate 3 (R = benzyl) which was used for preparing coenzyme Q10, in moderate to high yields.

Synthetic studies on coenzyme Q10: Part 2 - A efficient and improved synthesis of coenzyme Q10 via the C5 + C 45 approach

An improved route to coenzyme Q10 (1) starting from commercially available coenzyme Q1 is described. The key steps in this synthesis are the SeO2-mediated oxidation of the protected isoprenylhydroquinone 3 into the (E)-allyl alcohol 5 without the formation of undesired stereoisomer and the one-pot reductive elimination of the phenylsulfonyl and dibenzyl groups in 7 by using naphthalenyllithium.