GB738612A - Process for the production of a heteroside of meadow saffron and new product obtained in the course thereof - Google Patents

Process for the production of a heteroside of meadow saffron and new product obtained in the course thereof

Info

Publication number
GB738612A
GB738612A GB8086/53A GB808653A GB738612A GB 738612 A GB738612 A GB 738612A GB 8086/53 A GB8086/53 A GB 8086/53A GB 808653 A GB808653 A GB 808653A GB 738612 A GB738612 A GB 738612A
Authority
GB
United Kingdom
Prior art keywords
colchicoside
acetate
production
heteroside
course
Prior art date
Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
Expired
Application number
GB8086/53A
Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)
Sanofi Aventis France
Original Assignee
Roussel Uclaf SA
Priority date (The priority date is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the date listed.)
Filing date
Publication date
Application filed by Roussel Uclaf SA filed Critical Roussel Uclaf SA
Publication of GB738612A publication Critical patent/GB738612A/en
Expired legal-status Critical Current

Links

Classifications

    • CCHEMISTRY; METALLURGY
    • C07ORGANIC CHEMISTRY
    • C07HSUGARS; DERIVATIVES THEREOF; NUCLEOSIDES; NUCLEOTIDES; NUCLEIC ACIDS
    • C07H15/00Compounds containing hydrocarbon or substituted hydrocarbon radicals directly attached to hetero atoms of saccharide radicals
    • C07H15/20Carbocyclic rings
    • C07H15/24Condensed ring systems having three or more rings
    • C07H15/248Colchicine radicals, e.g. colchicosides

Landscapes

  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Health & Medical Sciences (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • Engineering & Computer Science (AREA)
  • Biochemistry (AREA)
  • Biotechnology (AREA)
  • General Health & Medical Sciences (AREA)
  • Genetics & Genomics (AREA)
  • Molecular Biology (AREA)
  • Saccharide Compounds (AREA)

Abstract

The invention comprises: (a) the acetate of colchicoside, having one of the constitutions represented by the formula <FORM:0738612/IV (b)/1> (wherein one of the symbols R1 represents <FORM:0738612/IV (b)/2> and the other two represent methyl groups); (b) the production thereof from the constituent of meadow saffron named "Substance C" (Santavy and Reichstein) by condensing its free phenolic group with a -acetobromoglucose; (c) the preparation of colchicoside by alcoholysis of the acetate in the presence of an alkali and a lower (1-5 C) aliphatic alcohol. The alcoholysis in (c) may be effected with methanol, ethanol or propanol and dilute caustic soda or caustic potash, and if the resulting colchicoside does not crystallize out directly it may be extracted with a mixture of a lower aliphatic alcohol and an aliphatic chlorinated hydrocarbon (e.g. a 1 : 3 mixture of ethanol and chloroform). The acetate is also obtainable by direct acetylation of colchicoside obtained from natural sources by the process of Specification 732,265. An example is given of processes (b) and (c) above.
GB8086/53A 1952-03-28 1953-03-24 Process for the production of a heteroside of meadow saffron and new product obtained in the course thereof Expired GB738612A (en)

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
FR738612X 1952-03-28

Publications (1)

Publication Number Publication Date
GB738612A true GB738612A (en) 1955-10-19

Family

ID=9132357

Family Applications (1)

Application Number Title Priority Date Filing Date
GB8086/53A Expired GB738612A (en) 1952-03-28 1953-03-24 Process for the production of a heteroside of meadow saffron and new product obtained in the course thereof

Country Status (1)

Country Link
GB (1) GB738612A (en)

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