1173-76-8

Usage

Uses

Used in Pharmaceutical Applications:
2,5-Cyclohexadiene-1,4-dione,2,3-dimethoxy-5-methyl-6-[(2E,6E)-3,7,11-trimethyl-2,6,10-dodecatrien-1-yl]is used as a potential pharmaceutical agent for its antioxidant properties. Its presence in algae and seafood suggests that it may have health benefits, making it a candidate for further research and development in the pharmaceutical industry.
Used in Nutraceutical Applications:
In the nutraceutical industry, 2,5-Cyclohexadiene-1,4-dione,2,3-dimethoxy-5-methyl-6-[(2E,6E)-3,7,11-trimethyl-2,6,10-dodecatrien-1-yl]is used as a dietary supplement or functional food ingredient due to its antioxidant properties. Its natural occurrence in certain foods and its potential health benefits make it a valuable component in the development of nutraceutical products.

Upstream product

• 69422-80-6 2,3-Dimethoxy-5-methyl-6-((2E,6E)-3,7,11-trimethyl-dodeca-2,6,10-trienyl)-benzene-1,4-diol 
• 22850-55-1 (E)-6,10-dimethyl-5,9-undecadien-1-yne 
• 75-24-1 trimethylaluminum 
• 202843-56-9 2-chloromethyl-5,6-dimethoxy-3-methyl-[1,4]benzoquinone 
• 212564-12-0 2,3-dichloro-5-methyl[5,6-13C₂]-1,4-benzoquinone 
• 264870-35-1 2,3-dimethoxy-5-methyl-[5,6-13C₂]-1,4-benzoquinone 
• 72132-89-9 farnesyl trimethyltin 
• 83626-21-5 2,3-Dimethoxy-6-methyl-4-((2E,6E)-3,7,11-trimethyl-dodeca-2,6,10-trienyloxy)-phenol 
• 488115-81-7 (2E/Z,6E)-farnesyl bromide 
• 56194-28-6 3,7,11-trimethyl-2ξ,6E,10-dodecatrien-1-ol 
• 36776-51-9 2,3,6-tribromo-4-methyl-phenol 
• 35896-58-3 2,3,4,5-tetramethoxytoluene 
• 106-44-5 p-cresol 
• 605-94-7 2,3-Dimethoxy-5-methyl-1,4-benzoquinone 

Downstream Products

• 77878-70-7 6-(12-hydroxy-3,7,11-trimethyl-2,6,10-dodecatrienyl)-2,3-dimethoxy-5-methylhydroquinone diacetate 
• 122907-50-0 6-(12-hydroxy-3,7,11-trimethyl-2,6,10-dodecatrienyl)-2,3-dimethoxy-5-methyl-1,4-benzoquinone 
• 69422-80-6 ubiquinol-3 

Relevant academic research and scientific papers

A novel, highly selective, and general methodology for the synthesis of 1,5-diene-containing oligoisoprenoids of all possible geometrical combinations exemplified by an iterative and convergent synthesis of coenzyme Q10

Chemical equation presented A truly general, versatile, and highly regio- and stereoselective methodology for the synthesis of terpenoids containing 1,5-diene units of E and/or Z geometry critically involves Pd-catalyzed homoallyl- and homopropargyl-alkenyl coupling and Zr-catalyzed carboalumination of alkynes. By using this methodology, coenzyme Q10, (E,Z,E)-geranylgeranoil, and other natural or unnatural compounds have been synthesized efficiently.

New efficient synthesis of ubiquinones

A strategy for the ecofriendly and high-yielding synthesis of ubiquinones starting from simple materials and using mild conditions is reported. CoQ1, CoQ2, CoQ3, and CoQ9 were prepared. Copyright Taylor & Francis Group, LLC.

Radical-scavenging polyphenols: New strategies for their synthesis

New strategies for the synthesis of polyphenols, compounds with antioxidant properties contained in every kind of plants, are discussed. Syntheses of different classes of polyphenols, namely ubiquinones, present in many natural systems in which electron-transfer mechanisms are involved, hydroxytyrosol, one of the main components of the phenol fraction in olives, and flavonoids, widespread in the plant kingdom, were approached by simple and environmentally sustainable methods.

New convenient synthesis of iridol. An approach to the synthesis of ubiquinones

A strategy for the synthesis of ubiquinones, in which iridol is the key intermediate, has been developed, together with a new convenient synthesis of iridol (2,3-dimethoxy-5-methylphenol) starting from the easily available 4-methylphenol and using mild conditions and friendly and high-yielding reactions.

Synthesis of [3-D3]-, [3-13C]-, and [1,2-13C2]propynes and their use for the synthesis of [5-D3-methyl]-, [5-13C-methyl]-, and [5,6- 13,C2-2,5-cyclohexadienyl]ubiquinones 3

Three selectively labeled propynes were prepared either with deuterium or carbon-13 at position 3 and doubly labeled with carbon-13 at positions 1 and 2 by an alkylation reaction from the corresponding labeled or unlabeled monolithio acetylides and dimethylsulfates. Their lithiation with nBuLi gave the corresponding propynyllithium derivatives which reacted with dimethyl squarate to afford the corresponding propargylic alcohols. These were thermolysed in p-xylene to furnish [5-D3-methyl]-, [5-13C-methyl]-, and [5,6-13C2-2,5-cyclohexadienyl]ubiquinone. The farnesyl side chain was introduced onto the labeled quinones with farnesyl trimethyltin under BF3 catalysis to provide [5-D3-methyl]-, [5-13C-methyl]-, and [5,6-13C2- 2,5-cyclohexadienyl]ubiquinone 3 (6c, 6b, 6a, respectively).

A convergent approach to coenzyme Q

Syntheses of coenzyme Q3-8 are described, as well as related systems such as plastoquinone-5. Preparation of the higher homologues of the ubiquinones relies on two new conjunctive reagents, or "linchpins", each of which ultimately corresponds to two or three prenyl units. These allow for attachment of a polyprenyl halide at one end, followed by a Ni(0)-catalyzed cross-coupling at the other terminus with a chloromethylated p-quinone.

Synthesis of [2, 3-13c2-2,5-cyclohexadienyl] ubiquinone 3

Diethyl [2,3-13C2] succinate was prepared by the oxidative dimerization of ethyl lithio [2-13C] acetate in the presence of CuBr2. Its dienolate was generated with lithium diisopropylamide (LDA) and methylated wi

Synthesis of ubiquinones-3 specifically labelled with 13C at C(5)- or C(6)-positions

(5-13C) and (6-13C) ubiquinones-3 (20a and 20b) were synthesised from (1-13C) trichloroacetic acid (8a) in 12 steps. The key step was a Diels Alder reaction between 2,5-bis (trimethylsilyloxy)-3-methylfuran (2) and (2-sup

Total Synthesis of Linear Polyprenoids. 2. Improved preparation of the Aromatic Nucleus of Ubiquinone

Highly efficient copper-catalyzed polymethoxylation of tribromocresol is the key process in a three-step, practical approach to obtain ubiquinone 0 from p-cresol.Short syntheses of several ubiquinones were achieved via direct, copper-mediated coupling of 2-lithio-3,4,5,6-tetramethoxytoluene to the appropriate polyprenyl bromide.

REGIOSELECTIVE POLYPRENYL REARRANGEMENT OF POLYPRENYL 2,3,4,5-TETRASUBSTITUTED PHENYL ETHERS PROMOTED BY BORON TRIFLUORIDE

4-Acetoxy-6-polyprenyl-2,3,5-trimethylphenols or 2,3-dimethoxy-5-methyl-6-polyprenylhydroquinones were obtained selectively by the BF3*OEt2 catalyzed polyprenyl rearrangement of polyprenyl 4-acetoxy-2,3,5-trimethylphenyl ethers or polyprenyl 2,3-dimethoxy-4-hydroxy-5-methylphenyl ethers.