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Ubidecarenone

  • Synonyms: Coenzym Q, Ubiquinone-10
  • ATC: C01EB09
  • Use: Lorem  Lorem  Lorem 
  • Chemical name: Lorem ipsum dolor sit amet, consetetur sadipscing elitr, sed diam
  • Formula: Lorem ipsum dolor sit amet,
  • MW:863.37 g/mol
  • CAS-RN:303-98-0
  • InChI Key:ACTIUHUUMQJHFO-UPTCCGCDSA-N
  • InChI:InChI=1S/C59H90O4/c1-44(2)24-15-25-45(3)26-16-27-46(4)28-17-29-47(5)30-18-31-48(6)32-19-33-49(7)34-20-35-50(8)36-21-37-51(9)38-22-39-52(10)40-23-41-53(11)42-43-55-54(12)56(60)58(62-13)59(63-14)57(55)61/h24,26,28,30,32,34,36,38,40,42H,15-23,25,27,29,31,33,35,37,39,41,43H2,1-14H3/b45-26+,46-28+,47-30+,48-32+,49-34+,50-36+,51-38+,52-40+,53-42+
  • EINECS:206-147-9

Substance Classes

Enzymes

Synthesis Path
























  • a By fermentation from cultures of Sporidiobolus johnsonii (ATCC 20490), Sporidiobolus ruinenii (ATCC-20489), Oosporidium margaritiferum (ATCC 10676), Rhodotorula muciladinosa (AHM 3946), Xanthomonas stewartii (Pasteur-No. 1035 and 1036), Pseudomonas fluorescens, Candida novellus (ATCC 20275), Candida utilis (IAM 4200), bakers yeast, Gibberella fujikuroi or recombinant Escherichia coli.

Substances Referenced in Synthesis Path

CAS-RN Formula Chemical Name CAS Index Name
141-97-9 C6H10O3 acetoacetic acid ethyl ester Butanoic acid, 3-oxo-, ethyl ester
400010-23-3 C17H19ClO5S 2-(chloromethyl)-5,6-dimethoxy-3-methylphenol 4-methylbenzenesulfonate
400010-24-4 C51H85Al [(1E,5E,9E,13E,17E,21E,25E,29E,33E)-2,6,10,14,18,22,26,30,34,38-decamethyl-1,5,9,13,17,21,25,29,33,37-nonatriacontadecaenyl]dimethylaluminum
400010-26-6 C59H92O3 2-[(2E,6E,10E,14E,18E,22E,26E,30E,34E)-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-methylphenol
Lorem Lorem Lorem Lorem
Lorem Lorem Lorem Lorem
Lorem Lorem Lorem Lorem
Lorem Lorem Lorem Lorem
Lorem Lorem Lorem Lorem
Lorem Lorem Lorem Lorem
Lorem Lorem Lorem Lorem
Lorem Lorem Lorem Lorem
Lorem Lorem Lorem Lorem
Lorem Lorem Lorem Lorem
Lorem Lorem Lorem Lorem
Lorem Lorem Lorem Lorem
Lorem Lorem Lorem Lorem
Lorem Lorem Lorem Lorem
Lorem Lorem Lorem Lorem
Lorem Lorem Lorem Lorem
Lorem Lorem Lorem Lorem
Lorem Lorem Lorem Lorem
Lorem Lorem Lorem Lorem
Lorem Lorem Lorem Lorem

Trade Names

Country Trade Name Vendor Annotation
I Lorem Lorem
Lorem Lorem
Lorem Lorem
Lorem Lorem
Lorem Lorem
Lorem Lorem
J Lorem Lorem
USA Lorem ipsum Lorem
Lorem ipsum Lorem
Lorem Lorem
Lorem ipsum Lorem
Lorem Lorem
(wfm = withdrawn from market)

Formulations

  • Loremipsumdolorsitamet,consetetursadipscingelitr,seddiamnonumyeirmodtemporinviduntutlaboreetdoloremagnaaliquyamerat,seddiamvoluptua.Atveroeosetaccusam

References

    • a US 9 999 999 (Takeda; 24.1.1978; J-prior. 27.2.1976).
    •  DOS 9 999 999 (Kanegafuchi; appl. 9.9.1977; J-prior. 14.9.1976).
    •  US 9 999 999 (Kanegafuchi; 8.5.1984; J-prior. 14.9.1976).
    •  DOS 9 999 999 (Lab. Bellon; appl. 10.8.1978; GB-prior. 17.8.1977).
    •  WO 9 999 999 999 (DSM; 20.1.2005).
    •  WO 9 999 999 999 (Cargill; 10.6.2004).
  • fermentation with recombinant E. coli or other rec. strains:

    • US 9 999 999 (Kaneka Corp.; 8.10.2002; J-prior. 10.2.1999).
    • US 9 999 999 (Kaneka Corp.; 13.7.2004; J-prior. 24.8.1999).
    • US 9 999 999 (Kyowa Hakko; 19.10.2004; J-prior. 14.4.1998, 5.8.1998, 15.2.1999).
  • fermentation with Gibberella fujikuroi:

    • US 9 999 999 (Merck & Co.; 11.4.1967; prior. 15.3.1963, 29.6.1965).
    • US 9 999 999 (Merck & Co.; 11.4.1967; appl. 15.3.1963).
  • b1 improved synthesis by Nickel-catalyzed cross-coupling of 2-chloromethyl-5,6-dimethoxy-3-methyl-[1,4]benzoquinone (made from 3,4,5-trimethoxytoluene) with an in situ-derived vinyl alane (made from solanesol via solanesylchloride and propyne):

    • Lipshutz, B.H. et al.: Org. Lett. (ORLEF7) 7, 4095 (2005).
    • US 9 999 999 (B.H.Lipshutz; 8.4.2003; appl. 15.8.2000).
    • US 9 999 999 (B.H.Lipshutz; 8.2.2005; appl. 27.9.2002).
  • similar synthetic processes:

    • Lipshutz, B.H. et al.: J. Am. Chem. Soc. (JACSAT) 1999, 121, 11664.
  • Nickel-mediated coupling:

    • Lipshutz, B.H. et al.: J. Am. Chem. Soc. (JACSAT) 2002, 124, 14282.
  • b2 synthesis from 2,3,4,5-tetramethoxytoluene and Solanesol (via Isodecaprenol):

    • US 9 999 999 (D.D.West; 3.2.2004; appl. 19.4.2001).
  • synthesis from 2-methyl-4,5,6-trimethoxyphenol and decaprenol:

    • US 9 999 999 (Merck & Co.; 11.12.1962; appl. 3.9.1958).
  • synthesis from 2-bromo-5,6-dimethoxy-3-methyl-1,4-benzoquinone and decaprenylbromide with nickeltetracarbonyl:

    • US 9 999 999 (Eisai; 22.7.1975; J-prior. 6.4.1973).
  • synthesis from 2-methyl-4,5,6-trimethoxyphenol and decaprenol in presence of boric acid or boronic acids:

    • US 9 999 999 (Eisai; 13.12.1977; J-prior. 29.9.1975).
  • synthesis from 2,3,4,5-tetramethoxytoluene and geranylbromide:

    • US 9 999 999 (West, D.D.; 14.1.2003; appl. 14.6.2001).
  • Negishi synthesis of Q10 and geranylgeraniol:

    • Negishi, E. et al.: Org. Lett. (ORLEF7) 4, 261-264 (2002).
  • medical use as antihypertensive:

    • US 9 999 999 (Eisai; 30.4.1974; J-prior. 13.7.1972).
  • medical use for improvement of hearing:

    • US 9 999 999 (Eisai; 14.2.1978; J-prior. 5.3.1976).
  • medical use as gerontotherapeutic:

    • US 9 999 999 (The New England Institute; 29.5.1979; prior. 19.11.1976, 12.12.1977).