&agr;-crystal of cyclopentenone

Details &agr;-crystal of cyclopentenone &agr;-crystal of cyclopentenone

1999-12-29

2002-02-26

Padmanabhan, Sreeni (Department: 1621)

Organic compounds -- part of the class 532-570 series

Organic compounds

Oxygen containing

C568S338000, C568S343000, C568S347000, C568S361000

Reexamination Certificate

active

06350917

ABSTRACT:

TECHNICAL FIELD OF THE INVENTION
The present invention relates to crystals of trans-4,5-dihydroxy-2-cyclopenten-1-one of an &agr;-type having a physiological activity such as anticancer action useful in the fields of pharmaceuticals, foods and beverages.
PRIOR ART
trans-4,5-dihydroxy-2-cyclopenten-1-one has a physiological activity such as anticancer action and is a compound useful in the fields of pharmaceuticals, foods and beverages.
With regard to a method for the manufacture of trans-4,5-dihydroxy-2-cyclopenten-1-one, a chemical synthesis [Carbohydrate Research, pages 217-222 (1993) ] has been known. In addition, with regard to a practical manufacturing method, a method where uronic acid or uronic acid derivative (s) is/are heated and trans-4, 5-dihydroxy-2-cyclopenten-1-one is collected from the heated products is mentioned in WO98/13328. There is no description on crystals in trans-4,5-dihydroxy-2-cyclopenten-1-one obtained in the above-mentioned methods. With regard to a method for the manufacture of cis-4,5-dihydroxy-2-cyclopenten-1-one, there is a description in
Helvetica Chimica Acta,
volume 55, pages 2838-2844 (1972) and said compound was finally obtained as a sublimed substance.
Problems to be Solved by the Invention
Residue after concentration in vacuo and freeze-dried product of the aqueous solution of trans-4,5-dihydroxy-2-cyclopenten-1-one obtained by the above practical method are reddish brown syrupy substances usually containing 10-20% of water and they are difficult to handle and have no good thermostability.
An object of the present invention is to improve purity, thermostability and handling of trans-4,5-dihydroxy-2-cyclopenten-1-one.
Means to Solve the Problems
The present inventors have found that stable crystals having a specific X-ray diffraction pattern can be prepared when trans-4,5-dihydroxy-2-cyclopenten-1-one (hereinafter, just referred to as “the cyclopenten one”) is extracted from an aqueous solution of the cyclopenten one with an organic solvent and the extract concentrated in vacuo is crystallized, when the cyclopentenone is extracted from a residue after concentration in vacuo or a freeze-dried substance of an aqueous solution of the cyclopentenone with an organic solvent and crystallization is conducted for the extract, or when a residue after concentration in vacuo or a freeze-dried substance of an aqueous solution of the cyclopentenone is dissolved in alcohol and then an organic solvent is added to said alcoholic solution whereupon the present inventors have named said crystals as “the cyclopentenone crystals of an &agr;-type”.
As compared with the conventional residue after concentration in vacuo or a freeze-dried substance of an aqueous solution of the cyclopentenone, this crystals of an &agr;-type have been found to have significantly improved purity and much improved thermostability whereupon the present invention has been accomplished.
To sum up, the present invention relates to crystals of trans-4, 5-dihydroxy-2-cyclopenten-1-one of an &agr;-type.


REFERENCES:
patent: 6087401 (2000-07-01), Koyama et al.
Recherches dans la serie des cyclitols XLIV, Syntheses de cycloses derives du cyclopentrane; Helvectica Chimica Acta 1972, vol. 55 pp. 2838-2844 (Translation of summary only).
On the formation of reductic acid from pentoses or hexuronic acids; Carbohydrate Research 1993, vol. 274, pp. 217-222.

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