JP5313657B2 - テルペノイド化合物とカロテノイド化合物との分離方法 - Google Patents
テルペノイド化合物とカロテノイド化合物との分離方法 Download PDFInfo
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- JP5313657B2 JP5313657B2 JP2008330762A JP2008330762A JP5313657B2 JP 5313657 B2 JP5313657 B2 JP 5313657B2 JP 2008330762 A JP2008330762 A JP 2008330762A JP 2008330762 A JP2008330762 A JP 2008330762A JP 5313657 B2 JP5313657 B2 JP 5313657B2
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- compound
- carotenoid
- terpenoid
- synthetic adsorbent
- limonene
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- -1 terpenoid compound Chemical class 0.000 title claims description 100
- 235000021466 carotenoid Nutrition 0.000 title claims description 53
- 238000000926 separation method Methods 0.000 title claims description 7
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 58
- XMGQYMWWDOXHJM-UHFFFAOYSA-N limonene Chemical compound CC(=C)C1CCC(C)=CC1 XMGQYMWWDOXHJM-UHFFFAOYSA-N 0.000 claims description 48
- 239000003463 adsorbent Substances 0.000 claims description 41
- 229940087305 limonene Drugs 0.000 claims description 24
- 235000001510 limonene Nutrition 0.000 claims description 24
- 238000000034 method Methods 0.000 claims description 15
- 239000000243 solution Substances 0.000 claims description 13
- 235000020971 citrus fruits Nutrition 0.000 claims description 8
- 241000207199 Citrus Species 0.000 claims description 4
- 239000007864 aqueous solution Substances 0.000 claims description 4
- 125000005395 methacrylic acid group Chemical group 0.000 claims description 2
- 150000001747 carotenoids Chemical class 0.000 claims 1
- 150000001875 compounds Chemical class 0.000 claims 1
- 239000007788 liquid Substances 0.000 description 10
- DMASLKHVQRHNES-UPOGUZCLSA-N (3R)-beta,beta-caroten-3-ol Chemical compound C([C@H](O)CC=1C)C(C)(C)C=1/C=C/C(/C)=C/C=C/C(/C)=C/C=C/C=C(C)C=CC=C(C)C=CC1=C(C)CCCC1(C)C DMASLKHVQRHNES-UPOGUZCLSA-N 0.000 description 7
- NBZANZVJRKXVBH-ITUXNECMSA-N all-trans-alpha-cryptoxanthin Natural products CC(=C/C=C/C=C(C)/C=C/C=C(C)/C=C/C1=C(C)CC(O)CC1(C)C)C=CC=C(/C)C=CC2C(=CCCC2(C)C)C NBZANZVJRKXVBH-ITUXNECMSA-N 0.000 description 7
- DMASLKHVQRHNES-ITUXNECMSA-N beta-cryptoxanthin Natural products CC(=C/C=C/C=C(C)/C=C/C=C(C)/C=C/C1=C(C)CC(O)CC1(C)C)C=CC=C(/C)C=CC2=C(C)CCCC2(C)C DMASLKHVQRHNES-ITUXNECMSA-N 0.000 description 7
- 235000002360 beta-cryptoxanthin Nutrition 0.000 description 7
- 239000011774 beta-cryptoxanthin Substances 0.000 description 7
- 238000002290 gas chromatography-mass spectrometry Methods 0.000 description 7
- 241001672694 Citrus reticulata Species 0.000 description 6
- 239000011521 glass Substances 0.000 description 5
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 5
- 235000013305 food Nutrition 0.000 description 4
- ZWEHNKRNPOVVGH-UHFFFAOYSA-N 2-Butanone Chemical compound CCC(C)=O ZWEHNKRNPOVVGH-UHFFFAOYSA-N 0.000 description 3
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 3
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 3
- IMNFDUFMRHMDMM-UHFFFAOYSA-N N-Heptane Chemical compound CCCCCCC IMNFDUFMRHMDMM-UHFFFAOYSA-N 0.000 description 3
- 238000000605 extraction Methods 0.000 description 3
- 239000000126 substance Substances 0.000 description 3
- 241000283690 Bos taurus Species 0.000 description 2
- 239000004212 Cryptoxanthin Substances 0.000 description 2
- LCGLNKUTAGEVQW-UHFFFAOYSA-N Dimethyl ether Chemical compound COC LCGLNKUTAGEVQW-UHFFFAOYSA-N 0.000 description 2
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 2
- LRHPLDYGYMQRHN-UHFFFAOYSA-N N-Butanol Chemical compound CCCCO LRHPLDYGYMQRHN-UHFFFAOYSA-N 0.000 description 2
- 239000003480 eluent Substances 0.000 description 2
- 239000000706 filtrate Substances 0.000 description 2
- 238000001914 filtration Methods 0.000 description 2
- 239000000203 mixture Substances 0.000 description 2
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 2
- 239000003960 organic solvent Substances 0.000 description 2
- FDPIMTJIUBPUKL-UHFFFAOYSA-N pentan-3-one Chemical compound CCC(=O)CC FDPIMTJIUBPUKL-UHFFFAOYSA-N 0.000 description 2
- 230000001953 sensory effect Effects 0.000 description 2
- 238000001179 sorption measurement Methods 0.000 description 2
- CXBDYQVECUFKRK-UHFFFAOYSA-N 1-methoxybutane Chemical compound CCCCOC CXBDYQVECUFKRK-UHFFFAOYSA-N 0.000 description 1
- 229920000178 Acrylic resin Polymers 0.000 description 1
- 239000004925 Acrylic resin Substances 0.000 description 1
- 244000248349 Citrus limon Species 0.000 description 1
- 235000005979 Citrus limon Nutrition 0.000 description 1
- XOBKSJJDNFUZPF-UHFFFAOYSA-N Methoxyethane Chemical compound CCOC XOBKSJJDNFUZPF-UHFFFAOYSA-N 0.000 description 1
- VVQNEPGJFQJSBK-UHFFFAOYSA-N Methyl methacrylate Chemical compound COC(=O)C(C)=C VVQNEPGJFQJSBK-UHFFFAOYSA-N 0.000 description 1
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 1
- 229920002125 Sokalan® Polymers 0.000 description 1
- 230000000274 adsorptive effect Effects 0.000 description 1
- 238000004458 analytical method Methods 0.000 description 1
- 125000003118 aryl group Chemical group 0.000 description 1
- 238000009835 boiling Methods 0.000 description 1
- 239000012159 carrier gas Substances 0.000 description 1
- 229920001429 chelating resin Polymers 0.000 description 1
- 238000012790 confirmation Methods 0.000 description 1
- 238000007405 data analysis Methods 0.000 description 1
- 150000002170 ethers Chemical class 0.000 description 1
- 239000000284 extract Substances 0.000 description 1
- 238000007710 freezing Methods 0.000 description 1
- 230000008014 freezing Effects 0.000 description 1
- 239000005350 fused silica glass Substances 0.000 description 1
- 230000005484 gravity Effects 0.000 description 1
- 238000010438 heat treatment Methods 0.000 description 1
- 239000001307 helium Substances 0.000 description 1
- 229910052734 helium Inorganic materials 0.000 description 1
- SWQJXJOGLNCZEY-UHFFFAOYSA-N helium atom Chemical compound [He] SWQJXJOGLNCZEY-UHFFFAOYSA-N 0.000 description 1
- 238000007689 inspection Methods 0.000 description 1
- 150000002576 ketones Chemical class 0.000 description 1
- 230000014759 maintenance of location Effects 0.000 description 1
- 238000001819 mass spectrum Methods 0.000 description 1
- 239000000113 methacrylic resin Substances 0.000 description 1
- 239000004570 mortar (masonry) Substances 0.000 description 1
- 125000000962 organic group Chemical group 0.000 description 1
- 238000010525 oxidative degradation reaction Methods 0.000 description 1
- 238000010298 pulverizing process Methods 0.000 description 1
- 229930195734 saturated hydrocarbon Natural products 0.000 description 1
Images
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- Treatment Of Liquids With Adsorbents In General (AREA)
- Solid-Sorbent Or Filter-Aiding Compositions (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Description
尚、温州みかん等の柑橘類からβ−クリプトキサンチンを抽出する技術は、当業者が行う通常の技術であり、先行技術文献等は示さない。
これにより、テルペノイド化合物とカロテノイド化合物とを簡便に分離することができる。
温州みかん外皮(宮川早生)9.24gを細刻後、特級エタノール(99.5%(v/v))と共にホモジナイザーにかけた。減圧濾過し、残渣を乳鉢に入れ、特級エタノールを加え、さらにすり潰した。減圧濾過し、この作業を濾液の色がなくなるまで繰り返した。濾液を減圧濃縮し特級エタノールで20mlに定容した(試料A)。
合成吸着剤として三菱化学製ダイヤイオンHP2MGを用い、これを特級エタノールで膨潤させた後、ガラスカラムに充填し、そのヘッドから試料Aを2ml、70%(v/v)エタノール15ml、特級エタノール55mlの順に流した。70%(v/v)エタノール15mlを流している間にカラム下部から溶離してきた透明な溶離液は捨て、次に溶離してきた黄色い液を分画し、フラクション1とした。次いで、薄い黄色の溶離液をフラクション2とした。さらに、特級エタノール55mlをヘッドから流している間に溶離してきた薄く黄色に色づいた液をフラクション3とし、濃い黄色の液をフラクション4とした。その後、黄色みが減じた薄い黄色の液をフラクション5として分画した。
官能検査はフラクション1〜5の匂いを嗅ぎ、リモネン様の匂いを感じるかで確認した。その結果、フラクショ1〜3にリモネンが溶出していることが推察された。さらに、リモネンの確認のため、試料A及びフラクション4と5とをあわせたもの(試料B)を、GC-MS分析し、それぞれ図1、2に示した。
Hewlett Packard Chemistation Systemによりデータ解析及びライブラリーサーチを行った。マススペクトルとKovatsの保持指標が標準物質と一致する成分をリモネンと同定した。その結果、試料Aでは、図1に示すようにリモネンのピーク(20.48分)が認められたのに対し、試料Bでは、図2に示すようにリモネンのピークが認められなかった。
以上により、テルペノイド化合物とカロテノイド化合物とを含む溶液を、合成吸着剤を充填したカラムに1回通すだけで、テルペノイド化合物とカロテノイド化合物とを簡便に分離できることが分かった。
GC-MSにそれぞれの試料を1μL注入し同定した。
GC-MS:Hewlett Packard 6890シリーズGC/MSDシステム
カラム:DB-Wax(J&W Scientific)、長さ60m、内径0.25mm、膜厚0.25μm、溶融シリカキャピラリーカラム
キャリアーガス:ヘリウム、線速度25cm/sec
スプリット比:20:1
注入口温度:260℃
カラム温度:40℃、5分間保持、3℃/minで200℃まで昇温、200℃で30分間保持
トランスファーライン温度:250℃
イオン化EI:70eV
走査:m/z10−300、1秒間1.58回
Claims (5)
- 柑橘果皮からエタノールを使用して抽出された、テルペノイド化合物であるリモネンとカロテノイド化合物とを含む溶液を、脂肪族エステルの構造を有する合成吸着剤に接触させて前記リモネンと前記カロテノイド化合物とを前記合成吸着剤に吸着させた後、当該合成吸着剤から前記リモネンを脱離させるテルペノイド化合物とカロテノイド化合物との分離方法。
- 前記リモネンと前記カロテノイド化合物とを前記合成吸着剤に吸着させた後、当該合成吸着剤にエタノール水溶液を接触させて、前記合成吸着剤から前記リモネンを脱離させる請求項1に記載のテルペノイド化合物とカロテノイド化合物との分離方法。
- 前記リモネンを脱離させた後、前記合成吸着剤から前記カロテノイド化合物を脱離させる請求項1または2に記載のテルペノイド化合物とカロテノイド化合物との分離方法。
- 前記合成吸着剤に、エタノール水溶液をエタノールの濃度を段階的に変えて接触させることにより、前記合成吸着剤から前記リモネンと前記カロテノイド化合物とを順次脱離させる請求項3に記載のテルペノイド化合物とカロテノイド化合物との分離方法。
- 前記合成吸着剤は、メタクリル系の合成吸着剤である請求項1〜4のいずれか1項に記載のテルペノイド化合物とカロテノイド化合物との分離方法。
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AU562818B2 (en) * | 1982-02-17 | 1987-06-18 | Tropicana Products, Inc. | Treatment of citrus fruit peel |
JPS62190090A (ja) * | 1986-02-18 | 1987-08-20 | Lotte Co Ltd | 天然粉末色素の製造方法 |
JPH07304977A (ja) * | 1994-05-12 | 1995-11-21 | Sanei Gen F F I Inc | 安定性の優れたカロテノイド色素の製造法 |
JP3178803B2 (ja) * | 1997-08-20 | 2001-06-25 | 株式会社愛媛柑橘資源開発研究所 | カロチノイド高含有ジュースの製造方法 |
JP3944532B2 (ja) * | 1998-10-30 | 2007-07-11 | 独立行政法人農業・食品産業技術総合研究機構 | 高純度β−クリプトキサンチンの製造方法 |
JP2002047201A (ja) * | 2001-05-07 | 2002-02-12 | Kanebo Ltd | 植物代謝産物の製造方法 |
MY130618A (en) * | 2002-11-27 | 2007-07-31 | Malaysian Palm Oil Board | A method of extracting and isolating minor components from vegetable oil |
CN1956950A (zh) * | 2005-02-25 | 2007-05-02 | 雅马哈发动机株式会社 | 叶黄素的回收方法 |
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