JP4235389B2 - 新規なピロール誘導体 - Google Patents
新規なピロール誘導体 Download PDFInfo
- Publication number
- JP4235389B2 JP4235389B2 JP2002029218A JP2002029218A JP4235389B2 JP 4235389 B2 JP4235389 B2 JP 4235389B2 JP 2002029218 A JP2002029218 A JP 2002029218A JP 2002029218 A JP2002029218 A JP 2002029218A JP 4235389 B2 JP4235389 B2 JP 4235389B2
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- JP
- Japan
- Prior art keywords
- absorption spectrum
- soluble
- nmr
- ppm
- ethanol
- 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 - Fee Related
Links
- 150000003233 pyrroles Chemical class 0.000 title description 4
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 claims description 60
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 44
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 claims description 42
- 229920002472 Starch Polymers 0.000 claims description 27
- 239000008107 starch Substances 0.000 claims description 27
- 235000019698 starch Nutrition 0.000 claims description 27
- 238000000862 absorption spectrum Methods 0.000 claims description 21
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 19
- 239000002904 solvent Substances 0.000 claims description 18
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 claims description 16
- 230000032683 aging Effects 0.000 claims description 16
- 239000000284 extract Substances 0.000 claims description 12
- 238000000605 extraction Methods 0.000 claims description 12
- 239000004480 active ingredient Substances 0.000 claims description 10
- SRPREECLSOIPNK-UHFFFAOYSA-N pyrraline Chemical class OCC1=CC=C(C=O)N1 SRPREECLSOIPNK-UHFFFAOYSA-N 0.000 claims description 10
- 238000005160 1H NMR spectroscopy Methods 0.000 claims description 8
- 238000002451 electron ionisation mass spectrometry Methods 0.000 claims description 8
- 239000011345 viscous material Substances 0.000 claims description 8
- 238000004587 chromatography analysis Methods 0.000 claims description 7
- 238000000034 method Methods 0.000 claims description 7
- 235000002566 Capsicum Nutrition 0.000 claims description 6
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 claims description 5
- 239000003242 anti bacterial agent Substances 0.000 claims description 5
- 235000013399 edible fruits Nutrition 0.000 claims description 5
- 239000003112 inhibitor Substances 0.000 claims description 5
- 239000000741 silica gel Substances 0.000 claims description 5
- 229910002027 silica gel Inorganic materials 0.000 claims description 5
- 238000001644 13C nuclear magnetic resonance spectroscopy Methods 0.000 claims description 4
- 208000033962 Fontaine progeroid syndrome Diseases 0.000 claims description 4
- 238000002290 gas chromatography-mass spectrometry Methods 0.000 claims description 4
- 238000004949 mass spectrometry Methods 0.000 claims description 4
- 238000005192 partition Methods 0.000 claims description 4
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 claims 6
- 241000208293 Capsicum Species 0.000 claims 3
- 239000001390 capsicum minimum Substances 0.000 claims 3
- 239000002798 polar solvent Substances 0.000 claims 3
- ZSKGQVFRTSEPJT-UHFFFAOYSA-N pyrrole-2-carboxaldehyde Chemical class O=CC1=CC=CN1 ZSKGQVFRTSEPJT-UHFFFAOYSA-N 0.000 claims 3
- 125000000218 acetic acid group Chemical group C(C)(=O)* 0.000 claims 2
- 239000002253 acid Substances 0.000 claims 1
- 239000004599 antimicrobial Substances 0.000 claims 1
- 150000001875 compounds Chemical class 0.000 description 40
- 240000004160 Capsicum annuum Species 0.000 description 10
- 235000008534 Capsicum annuum var annuum Nutrition 0.000 description 10
- 230000000844 anti-bacterial effect Effects 0.000 description 9
- 235000013305 food Nutrition 0.000 description 9
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 8
- 239000001511 capsicum annuum Substances 0.000 description 7
- 238000000746 purification Methods 0.000 description 7
- 239000000126 substance Substances 0.000 description 7
- WFDIJRYMOXRFFG-UHFFFAOYSA-N Acetic anhydride Chemical compound CC(=O)OC(C)=O WFDIJRYMOXRFFG-UHFFFAOYSA-N 0.000 description 6
- WORJEOGGNQDSOE-UHFFFAOYSA-N chloroform;methanol Chemical compound OC.ClC(Cl)Cl WORJEOGGNQDSOE-UHFFFAOYSA-N 0.000 description 6
- 239000003480 eluent Substances 0.000 description 6
- 238000000926 separation method Methods 0.000 description 5
- 238000010898 silica gel chromatography Methods 0.000 description 5
- -1 1,2,3-triazin-5-yl Chemical group 0.000 description 4
- 240000007594 Oryza sativa Species 0.000 description 4
- 235000007164 Oryza sativa Nutrition 0.000 description 4
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 4
- 238000004128 high performance liquid chromatography Methods 0.000 description 4
- 239000007788 liquid Substances 0.000 description 4
- 235000009566 rice Nutrition 0.000 description 4
- 241000894006 Bacteria Species 0.000 description 3
- 240000004808 Saccharomyces cerevisiae Species 0.000 description 3
- 125000002777 acetyl group Chemical group [H]C([H])([H])C(*)=O 0.000 description 3
- 239000012043 crude product Substances 0.000 description 3
- 230000002401 inhibitory effect Effects 0.000 description 3
- 238000004519 manufacturing process Methods 0.000 description 3
- 239000000843 powder Substances 0.000 description 3
- 230000001737 promoting effect Effects 0.000 description 3
- 239000012264 purified product Substances 0.000 description 3
- ISGQEBNHNUYCHL-UHFFFAOYSA-N (5-formyl-1H-pyrrol-2-yl)methyl acetate Chemical group CC(=O)OCC1=CC=C(C=O)N1 ISGQEBNHNUYCHL-UHFFFAOYSA-N 0.000 description 2
- 235000007862 Capsicum baccatum Nutrition 0.000 description 2
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 2
- 241000196324 Embryophyta Species 0.000 description 2
- 241000192125 Firmicutes Species 0.000 description 2
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 2
- 238000005481 NMR spectroscopy Methods 0.000 description 2
- 241000758706 Piperaceae Species 0.000 description 2
- 235000014680 Saccharomyces cerevisiae Nutrition 0.000 description 2
- PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 2
- 239000003463 adsorbent Substances 0.000 description 2
- 239000001728 capsicum frutescens Substances 0.000 description 2
- 230000000052 comparative effect Effects 0.000 description 2
- 238000001816 cooling Methods 0.000 description 2
- 238000012258 culturing Methods 0.000 description 2
- 239000005457 ice water Substances 0.000 description 2
- 230000005764 inhibitory process Effects 0.000 description 2
- 239000002609 medium Substances 0.000 description 2
- 239000000203 mixture Substances 0.000 description 2
- 230000002265 prevention Effects 0.000 description 2
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 2
- 239000002994 raw material Substances 0.000 description 2
- 238000011160 research Methods 0.000 description 2
- 238000003860 storage Methods 0.000 description 2
- 125000001424 substituent group Chemical group 0.000 description 2
- 235000019587 texture Nutrition 0.000 description 2
- 238000005406 washing Methods 0.000 description 2
- JYEUMXHLPRZUAT-UHFFFAOYSA-N 1,2,3-triazine Chemical group C1=CN=NN=C1 JYEUMXHLPRZUAT-UHFFFAOYSA-N 0.000 description 1
- ZCYVEMRRCGMTRW-UHFFFAOYSA-N 7553-56-2 Chemical compound [I] ZCYVEMRRCGMTRW-UHFFFAOYSA-N 0.000 description 1
- 229920001817 Agar Polymers 0.000 description 1
- 239000004382 Amylase Substances 0.000 description 1
- 102000013142 Amylases Human genes 0.000 description 1
- 108010065511 Amylases Proteins 0.000 description 1
- 229920001353 Dextrin Polymers 0.000 description 1
- 239000004375 Dextrin Substances 0.000 description 1
- 208000035859 Drug effect increased Diseases 0.000 description 1
- 239000006002 Pepper Substances 0.000 description 1
- 241000722363 Piper Species 0.000 description 1
- 235000016761 Piper aduncum Nutrition 0.000 description 1
- 235000017804 Piper guineense Nutrition 0.000 description 1
- 235000008184 Piper nigrum Nutrition 0.000 description 1
- 230000001133 acceleration Effects 0.000 description 1
- 238000007792 addition Methods 0.000 description 1
- 238000005377 adsorption chromatography Methods 0.000 description 1
- 239000008272 agar Substances 0.000 description 1
- 239000003513 alkali Substances 0.000 description 1
- 235000019418 amylase Nutrition 0.000 description 1
- 230000000845 anti-microbial effect Effects 0.000 description 1
- 238000009835 boiling Methods 0.000 description 1
- 235000008429 bread Nutrition 0.000 description 1
- 150000001720 carbohydrates Chemical class 0.000 description 1
- 238000004440 column chromatography Methods 0.000 description 1
- 238000010411 cooking Methods 0.000 description 1
- 238000004042 decolorization Methods 0.000 description 1
- 238000005238 degreasing Methods 0.000 description 1
- 230000018109 developmental process Effects 0.000 description 1
- 235000019425 dextrin Nutrition 0.000 description 1
- 235000019621 digestibility Nutrition 0.000 description 1
- 239000003814 drug Substances 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 238000010828 elution Methods 0.000 description 1
- 239000003995 emulsifying agent Substances 0.000 description 1
- 238000010931 ester hydrolysis Methods 0.000 description 1
- 239000002024 ethyl acetate extract Substances 0.000 description 1
- 235000015220 hamburgers Nutrition 0.000 description 1
- 125000004029 hydroxymethyl group Chemical group [H]OC([H])([H])* 0.000 description 1
- 235000008446 instant noodles Nutrition 0.000 description 1
- 229910052740 iodine Inorganic materials 0.000 description 1
- 239000011630 iodine Substances 0.000 description 1
- 239000012046 mixed solvent Substances 0.000 description 1
- 238000004810 partition chromatography Methods 0.000 description 1
- 239000001965 potato dextrose agar Substances 0.000 description 1
- 229920001592 potato starch Polymers 0.000 description 1
- 239000000047 product Substances 0.000 description 1
- 238000000425 proton nuclear magnetic resonance spectrum Methods 0.000 description 1
- 125000000168 pyrrolyl group Chemical group 0.000 description 1
- 238000011084 recovery Methods 0.000 description 1
- 235000013580 sausages Nutrition 0.000 description 1
- 239000007787 solid Substances 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- 238000006467 substitution reaction Methods 0.000 description 1
- 239000013076 target substance Substances 0.000 description 1
- 235000019640 taste Nutrition 0.000 description 1
- 238000002834 transmittance Methods 0.000 description 1
Landscapes
- Agricultural Chemicals And Associated Chemicals (AREA)
- Food Preservation Except Freezing, Refrigeration, And Drying (AREA)
- General Preparation And Processing Of Foods (AREA)
- Pyrrole Compounds (AREA)
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP2002029218A JP4235389B2 (ja) | 2002-02-06 | 2002-02-06 | 新規なピロール誘導体 |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP2002029218A JP4235389B2 (ja) | 2002-02-06 | 2002-02-06 | 新規なピロール誘導体 |
Publications (3)
| Publication Number | Publication Date |
|---|---|
| JP2003231676A JP2003231676A (ja) | 2003-08-19 |
| JP2003231676A5 JP2003231676A5 (enExample) | 2005-08-11 |
| JP4235389B2 true JP4235389B2 (ja) | 2009-03-11 |
Family
ID=27773601
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2002029218A Expired - Fee Related JP4235389B2 (ja) | 2002-02-06 | 2002-02-06 | 新規なピロール誘導体 |
Country Status (1)
| Country | Link |
|---|---|
| JP (1) | JP4235389B2 (enExample) |
Families Citing this family (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JP2005350370A (ja) * | 2004-06-08 | 2005-12-22 | Higashimaru Shoyu Co Ltd | 新規化合物 |
-
2002
- 2002-02-06 JP JP2002029218A patent/JP4235389B2/ja not_active Expired - Fee Related
Also Published As
| Publication number | Publication date |
|---|---|
| JP2003231676A (ja) | 2003-08-19 |
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