Title:
METHOD FOR PRODUCING HIGH-PURITY CERAMIDE
Document Type and Number:
WIPO Patent Application WO/2013/094108
Kind Code:
A1
Abstract:
Provided is a method for producing an optically active ceramide by an N-acylation (amidation) reaction of an optically active aminodiol, wherein a crude ceramide produced therein is purified by an industrially advantageous process. Namely, provided is a method for producing a high-purity ceramide that has high diastereo purity with high yield.
A high-purity ceramide is produced by: a step wherein a ceramide represented by general formula (1) is produced by reacting an aminodiol with an alkyl ester having 1-5 carbon atoms of an aliphatic carboxylic acid having 12-24 carbon atoms, said aliphatic carboxylic acid optionally having a hydroxyl group, in a hydrocarbon solvent having 5-10 carbon atoms; and a step wherein an alcohol having 1-3 carbon atoms is added into the reaction mixture obtained in the preceding step, thereby causing crystals to precipitate.
(In the formula, R1 represents an alkyl group which has 13-17 carbon atoms and optionally has a carbon-carbon unsaturated bond; R2 represents an alkyl group which has 11-23 carbon atoms and optionally has a hydroxyl group; and * represents an optically active state.)
Inventors:
ISHIDA KENYA (JP)
YAGI KENJI (JP)
YAGI KENJI (JP)
Application Number:
PCT/JP2012/007122
Publication Date:
June 27, 2013
Filing Date:
November 07, 2012
Export Citation:
Assignee:
TAKASAGO PERFUMERY CO LTD (JP)
International Classes:
C07C231/02; C07C231/22; C07C233/18
Domestic Patent References:
| WO2008041571A1 | 2008-04-10 |
Foreign References:
| JPH10114732A | 1998-05-06 | |||
| JPH08283218A | 1996-10-29 | |||
| JPS62207247A | 1987-09-11 | |||
| US5618706A | 1997-04-08 | |||
| US5831125A | 1998-11-03 | |||
| US5840940A | 1998-11-24 | |||
| US5998668A | 1999-12-07 | |||
| US5872273A | 1999-02-16 | |||
| US6313317B1 | 2001-11-06 | |||
| US8207370B2 | 2012-06-26 |
Other References:
See also references of EP 2796444A4
SHAPIRO ET AL., J. AM. CHEM. SOC., vol. 80, 1958, pages 2170
G.I. GREGORY ET AL., J. CHEM. SOC., 1951, pages 2453
SHAPIRO ET AL., J. AM. CHEM. SOC., vol. 80, 1958, pages 2170
G.I. GREGORY ET AL., J. CHEM. SOC., 1951, pages 2453
Attorney, Agent or Firm:
SAEKI, NORIO (JP)
Norio Saeki (JP)
Norio Saeki (JP)
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Claims: