Title:
METHOD FOR PRODUCING GLUTARALDEHYDE DERIVATIVE ORIGINATING IN NATURAL MATERIAL
Document Type and Number:
WIPO Patent Application WO/2019/151299
Kind Code:
A1
Abstract:
Provided is a method for relatively efficiently producing a glutaraldehyde derivative using an iridoid compound occurring in nature as a starting material, said glutaraldehyde derivative holding a substituent which is attached to the pyran ring in the starting iridoid compound.
The method for producing a glutaraldehyde derivative using an iridoid compound occurring in nature as a starting material, said glutaraldehyde derivative holding at least one substituent structure which is attached to the pyran ring in the starting iridoid compound, is characterized by comprising using as a catalyst a solid acid or a liquid acid having a pKa of 5 or lower. The solid acid catalyst is at least one member selected from among silica alumina, zeolite, sulfated zirconia, bentonite and polystyrene sulfonic acid.
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Inventors:
TOMINAGA KEN-ICHI (JP)
SHIMAMOTO YASUHIRO (JP)
ISODA HIROKO (JP)
ASAKAWA MASUMI (JP)
SATO KAZUHIKO (JP)
SHIMAMOTO YASUHIRO (JP)
ISODA HIROKO (JP)
ASAKAWA MASUMI (JP)
SATO KAZUHIKO (JP)
Application Number:
PCT/JP2019/003098
Publication Date:
August 08, 2019
Filing Date:
January 30, 2019
Export Citation:
Assignee:
AIST (JP)
International Classes:
C07C67/313; C07C45/60; C07C47/36; C07C69/73; B01J21/12; B01J21/16; B01J27/053; B01J29/08; B01J31/02; C07B61/00
Domestic Patent References:
| WO2008136037A2 | 2008-11-13 |
Foreign References:
| JP2013216628A | 2013-10-24 |
Other References:
HAYES, ROY ET AL.: "Stereo-and enantioselective routes to functionalized cyclohexenes via heterodiene cycloadditions of 6-oxocyclohexene-1- carbaldehydes with ketene acetals", TETRAHEDRON, vol. 55, no. 44, 1999, pages 12907 - 12928, XP004180382, doi:10.1016/S0040-4020(99)00764-4
BECKETT, JOEL S. ET AL.: "A Divergent Approach to the Diastereoselective Synthesis of Several Ant- Associated Iridoids", ORGANIC LETTERS, vol. 12, no. 7, 2010, pages 1408 - 1411, XP055627930
PAIVA-MARTINS ET AL.: "Isolation and Characterization of a New Hydroxytyrosol Derivative from Olive (Olea europa ea) Leaves", JOURNAL OF AGRICULTURAL AND FOOD CHEMISTRY, vol. 56, no. 14, 2008, pages 5582 - 5588, XP055627933
BIANCO, ARMANDODORIANO ET AL.: "Acid rearrangement of secoiridoids related to oleuropein and secologanin", EUROPEAN JOURNAL OF ORGANIC CHEMISTRY, 2003, pages 4349 - 4354
VOUGOGIANNOPOULOU, KONSTANTINA ET AL.: "One-Step Semisynthesis of Oleacein and the Determination as a 5-Lipoxygenase Inhibitor", JOURNAL OF NATURAL PRODUCTS, vol. 77, no. 3, 2014, pages 441 - 445, XP055368058, doi:10.1021/np401010x
BECKETT, JOEL S. ET AL.: "A Divergent Approach to the Diastereoselective Synthesis of Several Ant- Associated Iridoids", ORGANIC LETTERS, vol. 12, no. 7, 2010, pages 1408 - 1411, XP055627930
PAIVA-MARTINS ET AL.: "Isolation and Characterization of a New Hydroxytyrosol Derivative from Olive (Olea europa ea) Leaves", JOURNAL OF AGRICULTURAL AND FOOD CHEMISTRY, vol. 56, no. 14, 2008, pages 5582 - 5588, XP055627933
BIANCO, ARMANDODORIANO ET AL.: "Acid rearrangement of secoiridoids related to oleuropein and secologanin", EUROPEAN JOURNAL OF ORGANIC CHEMISTRY, 2003, pages 4349 - 4354
VOUGOGIANNOPOULOU, KONSTANTINA ET AL.: "One-Step Semisynthesis of Oleacein and the Determination as a 5-Lipoxygenase Inhibitor", JOURNAL OF NATURAL PRODUCTS, vol. 77, no. 3, 2014, pages 441 - 445, XP055368058, doi:10.1021/np401010x
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