GB802669A - Process for the preparation of 1, 4-dicaffeylquinic acid - Google Patents

Process for the preparation of 1, 4-dicaffeylquinic acid

Info

Publication number
GB802669A
GB802669A GB15272/55A GB1527255A GB802669A GB 802669 A GB802669 A GB 802669A GB 15272/55 A GB15272/55 A GB 15272/55A GB 1527255 A GB1527255 A GB 1527255A GB 802669 A GB802669 A GB 802669A
Authority
GB
United Kingdom
Prior art keywords
acid
dicaffeylquinic
lead
treated
barium
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
GB15272/55A
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.)
Pfizer Italia SRL
Original Assignee
Farmaceutici Italia SpA
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 Farmaceutici Italia SpA filed Critical Farmaceutici Italia SpA
Publication of GB802669A publication Critical patent/GB802669A/en
Expired legal-status Critical Current

Links

Classifications

    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D307/00—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K31/00—Medicinal preparations containing organic active ingredients
    • A61K31/185—Acids; Anhydrides, halides or salts thereof, e.g. sulfur acids, imidic, hydrazonic or hydroximic acids
    • A61K31/19—Carboxylic acids, e.g. valproic acid
    • A61K31/192—Carboxylic acids, e.g. valproic acid having aromatic groups, e.g. sulindac, 2-aryl-propionic acids, ethacrynic acid 
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K31/00—Medicinal preparations containing organic active ingredients
    • A61K31/21—Esters, e.g. nitroglycerine, selenocyanates
    • A61K31/215—Esters, e.g. nitroglycerine, selenocyanates of carboxylic acids
    • A61K31/216—Esters, e.g. nitroglycerine, selenocyanates of carboxylic acids of acids having aromatic rings, e.g. benactizyne, clofibrate
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K36/00—Medicinal preparations of undetermined constitution containing material from algae, lichens, fungi or plants, or derivatives thereof, e.g. traditional herbal medicines
    • A61K36/18—Magnoliophyta (angiosperms)
    • A61K36/185—Magnoliopsida (dicotyledons)
    • A61K36/28—Asteraceae or Compositae (Aster or Sunflower family), e.g. chamomile, feverfew, yarrow or echinacea
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C69/00—Esters of carboxylic acids; Esters of carbonic or haloformic acids
    • C07C69/76—Esters of carboxylic acids having a carboxyl group bound to a carbon atom of a six-membered aromatic ring

Landscapes

  • Health & Medical Sciences (AREA)
  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • Natural Medicines & Medicinal Plants (AREA)
  • Veterinary Medicine (AREA)
  • Medicinal Chemistry (AREA)
  • Animal Behavior & Ethology (AREA)
  • General Health & Medical Sciences (AREA)
  • Public Health (AREA)
  • Pharmacology & Pharmacy (AREA)
  • Epidemiology (AREA)
  • Alternative & Traditional Medicine (AREA)
  • Engineering & Computer Science (AREA)
  • Emergency Medicine (AREA)
  • Biotechnology (AREA)
  • Botany (AREA)
  • Medical Informatics (AREA)
  • Microbiology (AREA)
  • Mycology (AREA)
  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
  • Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)

Abstract

The invention comprises 1,4-dicaffeylquinic acid of the formula <FORM:0802669/IV (b)/1> and a process for its isolation from a decoction liquor containing it (preferably obtained from leaves of cardoon, Cynara cardunculus, or artichoke, Cynara scolymus) by treating the liquor with an excess of a water-soluble salt of barium or lead, respectively in the cold or with heating, and freeing the resulting separated precipitate, which contains the barium or lead salt of 1,4-dicaffeylquinic acid, from impurities by selective separation under acid conditions. Three methods for the selective separation are described: (a) fractional elution of precipitated lead salts with 30-50 per cent acetic acid at 60-80 DEG C., the active substance being recovered from the acid solution thus obtained by removal of lead with sulphuric acid and H2S, and concentration of the remaining liquid; (b) total dissolution of the barium or lead salt in a very slight excess of 10 per cent nitric acid, followed by fractional crystallization; (c) dissolution of the accompanying impurities in a slight excess of dilute sulphuric acid and then extraction of 1,4-dicaffeylquinic acid from the insoluble residue with an organic solvent, e.g. methanol, ethanol or dioxane. The crude caffeylquinic acid obtained by the above methods is further purified by crystallization from dilute acetic acid or water. In examples: (1) carbon leaves are boiled with water, the hot liquor treated with excess lead acetate solution, the precipitate separated by filtration or centrifugation and 1,4-dicaffeylquinic acid isolated by method (a) above; (2) artichloke leaves are boiled with water, filtered, the decoction concentrated under reduced pressure and treated with barium nitrate and barium hydroxide, yielding a yellow precipitate which is treated by method (c), extracting dicaffeylquinic acid with alcohol; (3) the yellow precipitate obtained as in (2) is treated with dilute nitric acid and allowed to stand, when the quinic acid crystallizes; (4) the precipitate obtained by treating a decoction of cardoon or artichoke leaves with lead acetate solution is treated by method (c), using ethanol as the organic solvent. The structure of 1,4-dicaffeylquinic acid is confirmed (a) by acetylation to a hexa-acetate, which on hydrogenation gives a tetrahydro derivative; (b) by alkaline fusion to 3,4-dihydroxybenzoic acid; (c) saponification of the substance and of its tetrahydro derivative giving quinic acid together with 3,4-dihydroxy cinnamic acid or b -(3,4-dihydroxyphenyl) propionic acid respectively; and (d) by methylation to 1,4 - di - (31,41 - dimethoxycinnamoyl) quinic acid methyl ester. Specification 802,668 is referred to.
GB15272/55A 1954-05-28 1955-05-26 Process for the preparation of 1, 4-dicaffeylquinic acid Expired GB802669A (en)

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
IT336819X 1954-05-28

Publications (1)

Publication Number Publication Date
GB802669A true GB802669A (en) 1958-10-08

Family

ID=11238053

Family Applications (1)

Application Number Title Priority Date Filing Date
GB15272/55A Expired GB802669A (en) 1954-05-28 1955-05-26 Process for the preparation of 1, 4-dicaffeylquinic acid

Country Status (5)

Country Link
BE (1) BE538205A (en)
CH (1) CH336819A (en)
FR (1) FR1212005A (en)
GB (1) GB802669A (en)
NL (1) NL98113C (en)

Cited By (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO2003013562A1 (en) * 2001-08-08 2003-02-20 Lichtwer Pharma Ag Artichoke leaf extracts
WO2003057655A1 (en) * 2002-01-07 2003-07-17 Biogaia Fermentation Ab Process for the isolation of polyhydroxy cyclic carboxylic acids
CN1301721C (en) * 2003-07-23 2007-02-28 昆明英之源农业科技开发有限公司 Artichoke natural antioxidant and its extraction method

Cited By (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO2003013562A1 (en) * 2001-08-08 2003-02-20 Lichtwer Pharma Ag Artichoke leaf extracts
WO2003057655A1 (en) * 2002-01-07 2003-07-17 Biogaia Fermentation Ab Process for the isolation of polyhydroxy cyclic carboxylic acids
CN1301721C (en) * 2003-07-23 2007-02-28 昆明英之源农业科技开发有限公司 Artichoke natural antioxidant and its extraction method

Also Published As

Publication number Publication date
CH336819A (en) 1959-03-15
FR1212005A (en) 1960-03-21
BE538205A (en) 1955-06-15
NL98113C (en) 1961-05-15

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