JP5526374B2 - (e,e)−ファルネシルアセトンの調製方法 - Google Patents
(e,e)−ファルネシルアセトンの調製方法 Download PDFInfo
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- JP5526374B2 JP5526374B2 JP2010519414A JP2010519414A JP5526374B2 JP 5526374 B2 JP5526374 B2 JP 5526374B2 JP 2010519414 A JP2010519414 A JP 2010519414A JP 2010519414 A JP2010519414 A JP 2010519414A JP 5526374 B2 JP5526374 B2 JP 5526374B2
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- nerolidol
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- farnesyl acetone
- acetone
- farnesylacetone
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- 238000000034 method Methods 0.000 title claims description 14
- LTUMRKDLVGQMJU-UHFFFAOYSA-N famesylacetone Natural products CC(C)=CCCC(C)=CCCC(C)=CCCC(C)=O LTUMRKDLVGQMJU-UHFFFAOYSA-N 0.000 title description 12
- LTUMRKDLVGQMJU-IUBLYSDUSA-N farnesyl acetone Chemical compound CC(C)=CCC\C(C)=C\CC\C(C)=C\CCC(C)=O LTUMRKDLVGQMJU-IUBLYSDUSA-N 0.000 title 1
- FQTLCLSUCSAZDY-UHFFFAOYSA-N (+) E(S) nerolidol Natural products CC(C)=CCCC(C)=CCCC(C)(O)C=C FQTLCLSUCSAZDY-UHFFFAOYSA-N 0.000 claims description 25
- LTUMRKDLVGQMJU-ACJRHICRSA-N (5e)-6,10,14-trimethylpentadeca-5,9,13-trien-2-one Chemical compound CC(C)=CCCC(C)=CCC\C(C)=C\CCC(C)=O LTUMRKDLVGQMJU-ACJRHICRSA-N 0.000 claims description 25
- YOWQWFMSQCOSBA-UHFFFAOYSA-N 2-methoxypropene Chemical compound COC(C)=C YOWQWFMSQCOSBA-UHFFFAOYSA-N 0.000 claims description 14
- NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 claims description 14
- WASNIKZYIWZQIP-AWEZNQCLSA-N nerolidol Natural products CC(=CCCC(=CCC[C@@H](O)C=C)C)C WASNIKZYIWZQIP-AWEZNQCLSA-N 0.000 claims description 13
- FQTLCLSUCSAZDY-ATGUSINASA-N Nerolidol Chemical compound CC(C)=CCC\C(C)=C\CC[C@](C)(O)C=C FQTLCLSUCSAZDY-ATGUSINASA-N 0.000 claims description 12
- 239000003054 catalyst Substances 0.000 claims description 10
- FQTLCLSUCSAZDY-SZGZABIGSA-N (E)-Nerolidol Natural products CC(C)=CCC\C(C)=C/CC[C@@](C)(O)C=C FQTLCLSUCSAZDY-SZGZABIGSA-N 0.000 claims description 9
- FQTLCLSUCSAZDY-SDNWHVSQSA-N (6E)-nerolidol Chemical compound CC(C)=CCC\C(C)=C\CCC(C)(O)C=C FQTLCLSUCSAZDY-SDNWHVSQSA-N 0.000 claims description 8
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 claims description 8
- 230000002378 acidificating effect Effects 0.000 claims description 8
- 238000006243 chemical reaction Methods 0.000 claims description 8
- 229910000147 aluminium phosphate Inorganic materials 0.000 claims description 7
- 238000004508 fractional distillation Methods 0.000 claims description 7
- 238000002360 preparation method Methods 0.000 claims description 6
- 239000011541 reaction mixture Substances 0.000 claims description 5
- 239000003960 organic solvent Substances 0.000 claims description 3
- 238000002955 isolation Methods 0.000 claims 1
- 239000000203 mixture Substances 0.000 description 8
- JOXIMZWYDAKGHI-UHFFFAOYSA-N toluene-4-sulfonic acid Chemical compound CC1=CC=C(S(O)(=O)=O)C=C1 JOXIMZWYDAKGHI-UHFFFAOYSA-N 0.000 description 4
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 3
- MUBZPKHOEPUJKR-UHFFFAOYSA-N Oxalic acid Chemical compound OC(=O)C(O)=O MUBZPKHOEPUJKR-UHFFFAOYSA-N 0.000 description 3
- -1 allyl halide Chemical class 0.000 description 3
- 230000015572 biosynthetic process Effects 0.000 description 3
- 238000004821 distillation Methods 0.000 description 3
- 239000003205 fragrance Substances 0.000 description 3
- 238000004817 gas chromatography Methods 0.000 description 3
- 239000000047 product Substances 0.000 description 3
- 238000000926 separation method Methods 0.000 description 3
- 239000000243 solution Substances 0.000 description 3
- LTUMRKDLVGQMJU-ADPXBSPTSA-N (5z,9e)-6,10,14-trimethylpentadeca-5,9,13-trien-2-one Chemical compound CC(C)=CCC\C(C)=C\CC\C(C)=C/CCC(C)=O LTUMRKDLVGQMJU-ADPXBSPTSA-N 0.000 description 2
- FQTLCLSUCSAZDY-KAMYIIQDSA-N (6Z)-nerolidol Chemical compound CC(C)=CCC\C(C)=C/CCC(C)(O)C=C FQTLCLSUCSAZDY-KAMYIIQDSA-N 0.000 description 2
- 238000001644 13C nuclear magnetic resonance spectroscopy Methods 0.000 description 2
- MICBIPJWKDDGNL-UHFFFAOYSA-N 7',8'-dihydro-beta,psi-carotene Chemical compound CC(C)=CCCC(C)=CCCC(C)=CC=CC(C)=CC=CC=C(C)C=CC=C(C)C=CC1=C(C)CCCC1(C)C MICBIPJWKDDGNL-UHFFFAOYSA-N 0.000 description 2
- WFDIJRYMOXRFFG-UHFFFAOYSA-N Acetic anhydride Chemical compound CC(=O)OC(C)=O WFDIJRYMOXRFFG-UHFFFAOYSA-N 0.000 description 2
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 2
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 2
- AFVFQIVMOAPDHO-UHFFFAOYSA-N Methanesulfonic acid Chemical compound CS(O)(=O)=O AFVFQIVMOAPDHO-UHFFFAOYSA-N 0.000 description 2
- VMHLLURERBWHNL-UHFFFAOYSA-M Sodium acetate Chemical compound [Na+].CC([O-])=O VMHLLURERBWHNL-UHFFFAOYSA-M 0.000 description 2
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 2
- 150000001875 compounds Chemical class 0.000 description 2
- 238000001816 cooling Methods 0.000 description 2
- WASQWSOJHCZDFK-UHFFFAOYSA-N diketene Chemical compound C=C1CC(=O)O1 WASQWSOJHCZDFK-UHFFFAOYSA-N 0.000 description 2
- 239000000543 intermediate Substances 0.000 description 2
- 150000002576 ketones Chemical class 0.000 description 2
- CDOSHBSSFJOMGT-UHFFFAOYSA-N linalool Chemical compound CC(C)=CCCC(C)(O)C=C CDOSHBSSFJOMGT-UHFFFAOYSA-N 0.000 description 2
- 230000035484 reaction time Effects 0.000 description 2
- 239000001632 sodium acetate Substances 0.000 description 2
- 235000017281 sodium acetate Nutrition 0.000 description 2
- UAKCMIIOSJFOTD-UHFFFAOYSA-M sodium;3-oxobutanoate Chemical compound [Na+].CC(=O)CC([O-])=O UAKCMIIOSJFOTD-UHFFFAOYSA-M 0.000 description 2
- 229910001220 stainless steel Inorganic materials 0.000 description 2
- 239000010935 stainless steel Substances 0.000 description 2
- 230000000707 stereoselective effect Effects 0.000 description 2
- 238000003786 synthesis reaction Methods 0.000 description 2
- 239000002699 waste material Substances 0.000 description 2
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 2
- FOFMBFMTJFSEEY-YFVJMOTDSA-N (2e,6e)-1-bromo-3,7,11-trimethyldodeca-2,6,10-triene Chemical compound CC(C)=CCC\C(C)=C\CC\C(C)=C\CBr FOFMBFMTJFSEEY-YFVJMOTDSA-N 0.000 description 1
- 239000001490 (3R)-3,7-dimethylocta-1,6-dien-3-ol Substances 0.000 description 1
- CDOSHBSSFJOMGT-JTQLQIEISA-N (R)-linalool Natural products CC(C)=CCC[C@@](C)(O)C=C CDOSHBSSFJOMGT-JTQLQIEISA-N 0.000 description 1
- 238000005160 1H NMR spectroscopy Methods 0.000 description 1
- ZGIGZINMAOQWLX-NCZFFCEISA-N 3,7,11-Trimethyl-2,6,10-dodecatrienyl acetate Chemical compound CC(C)=CCC\C(C)=C\CC\C(C)=C\COC(C)=O ZGIGZINMAOQWLX-NCZFFCEISA-N 0.000 description 1
- 238000006563 Carroll rearrangement reaction Methods 0.000 description 1
- ZGIGZINMAOQWLX-UHFFFAOYSA-N Farnesyl acetate Natural products CC(C)=CCCC(C)=CCCC(C)=CCOC(C)=O ZGIGZINMAOQWLX-UHFFFAOYSA-N 0.000 description 1
- 238000003747 Grignard reaction Methods 0.000 description 1
- 229910019142 PO4 Inorganic materials 0.000 description 1
- 239000004809 Teflon Substances 0.000 description 1
- 229920006362 Teflon® Polymers 0.000 description 1
- WDJHALXBUFZDSR-UHFFFAOYSA-M acetoacetate Chemical compound CC(=O)CC([O-])=O WDJHALXBUFZDSR-UHFFFAOYSA-M 0.000 description 1
- 239000002253 acid Substances 0.000 description 1
- 150000007513 acids Chemical class 0.000 description 1
- XXROGKLTLUQVRX-UHFFFAOYSA-N allyl alcohol Chemical group OCC=C XXROGKLTLUQVRX-UHFFFAOYSA-N 0.000 description 1
- 239000007864 aqueous solution Substances 0.000 description 1
- YRMTZGJDOCHJPY-UHFFFAOYSA-N beta-Zeacarotene Natural products CC(=CC=CC(=CCCC(=CCCC(=CC=CC=C(/C)C=CC=C(/C)C=CC1=C(C)CCCC1(C)C)C)C)C)C YRMTZGJDOCHJPY-UHFFFAOYSA-N 0.000 description 1
- 238000009835 boiling Methods 0.000 description 1
- 150000001728 carbonyl compounds Chemical class 0.000 description 1
- 235000021466 carotenoid Nutrition 0.000 description 1
- 150000001747 carotenoids Chemical class 0.000 description 1
- 238000009903 catalytic hydrogenation reaction Methods 0.000 description 1
- 238000003776 cleavage reaction Methods 0.000 description 1
- 239000012043 crude product Substances 0.000 description 1
- 238000006114 decarboxylation reaction Methods 0.000 description 1
- 229940007703 farnesyl acetate Drugs 0.000 description 1
- 238000001914 filtration Methods 0.000 description 1
- 239000012467 final product Substances 0.000 description 1
- 239000000796 flavoring agent Substances 0.000 description 1
- 235000019634 flavors Nutrition 0.000 description 1
- 238000005194 fractionation Methods 0.000 description 1
- 229910052739 hydrogen Inorganic materials 0.000 description 1
- 229910000039 hydrogen halide Inorganic materials 0.000 description 1
- 239000012433 hydrogen halide Substances 0.000 description 1
- 150000002484 inorganic compounds Chemical class 0.000 description 1
- 229910010272 inorganic material Inorganic materials 0.000 description 1
- 229910052500 inorganic mineral Inorganic materials 0.000 description 1
- 229930007744 linalool Natural products 0.000 description 1
- 239000012528 membrane Substances 0.000 description 1
- 229940098779 methanesulfonic acid Drugs 0.000 description 1
- 239000011707 mineral Substances 0.000 description 1
- SYSQUGFVNFXIIT-UHFFFAOYSA-N n-[4-(1,3-benzoxazol-2-yl)phenyl]-4-nitrobenzenesulfonamide Chemical class C1=CC([N+](=O)[O-])=CC=C1S(=O)(=O)NC1=CC=C(C=2OC3=CC=CC=C3N=2)C=C1 SYSQUGFVNFXIIT-UHFFFAOYSA-N 0.000 description 1
- 229910052757 nitrogen Inorganic materials 0.000 description 1
- 150000007524 organic acids Chemical class 0.000 description 1
- 235000005985 organic acids Nutrition 0.000 description 1
- 150000002894 organic compounds Chemical class 0.000 description 1
- 235000006408 oxalic acid Nutrition 0.000 description 1
- ALBOWYHOENOWIO-UHFFFAOYSA-N pentadeca-5,9,13-trien-2-one Chemical compound CC=CCCC=CCCC=CCCC(C)=O ALBOWYHOENOWIO-UHFFFAOYSA-N 0.000 description 1
- 239000002304 perfume Substances 0.000 description 1
- NBIIXXVUZAFLBC-UHFFFAOYSA-K phosphate Chemical compound [O-]P([O-])([O-])=O NBIIXXVUZAFLBC-UHFFFAOYSA-K 0.000 description 1
- 239000010452 phosphate Substances 0.000 description 1
- 238000010992 reflux Methods 0.000 description 1
- 150000003839 salts Chemical class 0.000 description 1
- 230000007017 scission Effects 0.000 description 1
- QDRKDTQENPPHOJ-UHFFFAOYSA-N sodium ethoxide Chemical compound [Na+].CC[O-] QDRKDTQENPPHOJ-UHFFFAOYSA-N 0.000 description 1
- 239000007858 starting material Substances 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- CRDAMVZIKSXKFV-UHFFFAOYSA-N trans-Farnesol Natural products CC(C)=CCCC(C)=CCCC(C)=CCO CRDAMVZIKSXKFV-UHFFFAOYSA-N 0.000 description 1
- YNJBWRMUSHSURL-UHFFFAOYSA-N trichloroacetic acid Chemical compound OC(=O)C(Cl)(Cl)Cl YNJBWRMUSHSURL-UHFFFAOYSA-N 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C45/00—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds
- C07C45/51—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by pyrolysis, rearrangement or decomposition
- C07C45/511—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by pyrolysis, rearrangement or decomposition involving transformation of singly bound oxygen functional groups to >C = O groups
- C07C45/513—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by pyrolysis, rearrangement or decomposition involving transformation of singly bound oxygen functional groups to >C = O groups the singly bound functional group being an etherified hydroxyl group
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- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
- Fats And Perfumes (AREA)
- Seasonings (AREA)
Description
E−ネロリドールからのE/E−ファルネシルアセトンのリン酸接触調製。
ジャケット付き電熱および水冷システム、圧力センサーおよびステンレス鋼プロペラを備えた1.0リットルのステンレス鋼バッチ反応器(Medimex−High Pressure)に、アセトン中18重量%のH3PO4溶液1.2885g(2.37ミリモル、0.3モル%)とE−ネロリドール179.5g(0.790モル)の混合物を添加した。225gのイソプロペニルメチルエーテル(IPM、3.01モル、3.81当量)を添加した。撹拌下(500rpm)、混合物を2時間以内で160℃まで加熱した。16時間の全反応時間後、反応混合物を25℃まで冷却し、減圧下、反応器から吸引し、そして30分間、酢酸ナトリウム2gと一緒に撹拌した。5μのTeflon膜上での濾過後、40℃のRota ベイパーで2段階(ポンプで10ミリバールおよび0.05ミリバール)で低ボイラーを除去した。粗製生成物(収率93.1%、選択性0.94)を、PT 100、磁気撹拌器、Liebig冷却器、Anschutz Thieleセパレーター、冷却トラップおよび油浴中の高真空ポンプを備えた500mlの2つ口丸底フラスコで蒸留した。140℃の浴温度、125〜127℃の内部温度、118〜122℃のヘッド温度、および0.03〜0.02ミリバール(ポンプで)の絶対圧で、86%の収率でE/E−および(5Z,9E)−ファルネシルアセトンの混合物が得られた。E/E−および(5Z,9E)−ファルネシルアセトンの混合物の前留分は、それぞれ、67〜140℃、44.5〜123℃、27.3〜111℃および0.03ミリバール(ポンプで)で、3.7%の収率で得られた。主留分および前留分の合計収率89.7%、選択性0.9)。(5Z/9E)−ファルネシルアセトンから蒸留によってE/E−ファルネシルアセトンを分離した。1Hおよび13C−NMR分光法によって生成物を特徴づけた。純度はガスクロマトグラフィーによって決定した。
E/E−FA 300MHz 13C−NMR(CDCl3):δ(ppm,TMS)=208.8,136.4,135.0,131.3,124.4,124.0,122.5,43.8,39.7,39.6,29.9,26.8,26.5,25.5,22.5,17.7,16.0(2C).
実施例1に記載されたものと同様の方法で、199gのE−ネロリドール、1.38gの触媒溶液、および3.15当量のIPMから開始して、89.8%の収率、選択性0.90(粗製)、ならびに87.4%の収率、選択性0.87(主留分および前留分の合計、低および高ボイラーの分離後)で、E/E−および(5Z,9E)−ファルネシルアセトンの混合物を得た。
実施例1に記載されたものと同様の方法で、224.4gのE−ネロリドール、1.56gの触媒溶液、および2.5当量のIPMから開始して、88.2%の収率、選択性0.88(粗製)、ならびに86.1%の収率、選択性0.86(主留分および前留分の合計、低および高ボイラーの分離後)で、E/E−および(5Z,9E)−ファルネシルアセトンの混合物を得た。
Claims (6)
- 酸性触媒の存在下におけるネロリドールとイソプロペニルメチルエーテルとの反応、および分画蒸留による単離を特徴とするE/E−ファルネシルアセトンの調製方法であって、
前記酸性触媒は、有機溶媒中の、前記ネロリドールに対して0.01〜0.5モル%のリン酸であり、
前記ネロリドールは、E−ネロリドールであり、
前記ネロリドールと前記イソプロペニルメチルエーテルとのモル比が、1:2.5〜5.0であり、
前記反応が、100〜200℃で8〜20時間実行される反応である、E/E−ファルネシルアセトンの調製方法。 - 前記ネロリドールと前記イソプロペニルメチルエーテルとのモル比が、1:3.8〜5.0である、請求項1に記載の方法。
- 前記有機溶媒中の前記リン酸の濃度が、10〜30重量%である、請求項1又は2に記載の方法。
- 前記酸性触媒がアセトン溶液中のリン酸である請求項1〜3のいずれか一項に記載の方法。
- 0.1ミリバール未満の絶対圧力下での反応混合物の分画蒸留によって純粋なE/E−ファルネシルアセトンが得られる請求項1〜4のいずれか一項に記載の方法。
- 少なくとも90%の立体純度でE/E−ファルネシルアセトンが得られる請求項1〜5のいずれか一項に記載の方法。
Applications Claiming Priority (3)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
EP07015579 | 2007-08-08 | ||
EP07015579.1 | 2007-08-08 | ||
PCT/EP2008/059601 WO2009019132A1 (en) | 2007-08-08 | 2008-07-22 | Process for the preparation of (e, e)-farnesyl acetone |
Publications (2)
Publication Number | Publication Date |
---|---|
JP2010535730A JP2010535730A (ja) | 2010-11-25 |
JP5526374B2 true JP5526374B2 (ja) | 2014-06-18 |
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Application Number | Title | Priority Date | Filing Date |
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JP2010519414A Active JP5526374B2 (ja) | 2007-08-08 | 2008-07-22 | (e,e)−ファルネシルアセトンの調製方法 |
Country Status (5)
Country | Link |
---|---|
US (1) | US8217203B2 (ja) |
EP (1) | EP2188240B1 (ja) |
JP (1) | JP5526374B2 (ja) |
CN (2) | CN101778810A (ja) |
WO (1) | WO2009019132A1 (ja) |
Families Citing this family (5)
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BRPI0920620A2 (pt) * | 2008-10-21 | 2015-12-22 | Dsm Ip Assets Bv | fabricação de cetonas gama-delta insaturadas |
WO2015001030A1 (en) | 2013-07-05 | 2015-01-08 | Dsm Ip Assets B.V. | Formation of chiral 4-chromanones using chiral pyrrolidines in the presence of ureas or thioureas |
WO2015001031A1 (en) | 2013-07-05 | 2015-01-08 | Dsm Ip Assets B.V. | Formation of chiral 4-chromanones using chiral pyrrolidines |
WO2017098048A1 (en) | 2015-12-11 | 2017-06-15 | Dsm Ip Assets B.V. | Process for the manufacture of 6,10,14-trimethylpentadecan-2-one |
WO2018108606A1 (en) | 2016-12-12 | 2018-06-21 | Dsm Ip Assets B.V. | Process for the manufacture of 6,10-dimethylundecan-2-one, isophytol, alpha-tocopherol (acetate) and further intermediates thereof |
Family Cites Families (11)
Publication number | Priority date | Publication date | Assignee | Title |
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US3453317A (en) * | 1962-07-11 | 1969-07-01 | Hoffmann La Roche | Unsaturated carbonyl compounds and processes |
NL295084A (ja) | 1962-07-11 | 1900-01-01 | ||
JPS4880509A (ja) * | 1972-02-04 | 1973-10-29 | ||
CH597125A5 (ja) * | 1973-07-05 | 1978-03-31 | Hoffmann La Roche | |
JPH024726A (ja) * | 1988-06-24 | 1990-01-09 | Takasago Internatl Corp | △↑6‐トランス−ネロリドール及び△↑5‐トランス,△↑9‐トランス−ファルネシルアセトンの製造法 |
DE19649564A1 (de) * | 1996-11-29 | 1998-06-04 | Basf Ag | Verfahren zur Herstellung von gamma,delta-ungesättigter Ketone durch Umsetzung tertiärer Allylalkohole mit Alkenylalkylethern |
JP2002121166A (ja) * | 2000-10-16 | 2002-04-23 | Kuraray Co Ltd | 不飽和ケトンの製造方法 |
JP2002121165A (ja) * | 2000-10-16 | 2002-04-23 | Kuraray Co Ltd | 不飽和ケトンの製造方法 |
JP2002331023A (ja) * | 2001-05-11 | 2002-11-19 | Lion Corp | 芳香消臭組成物 |
CN1308279C (zh) | 2004-02-06 | 2007-04-04 | 上海三维制药有限公司 | 6,10,14,-三甲基-5e,9e,13-十五碳三烯-2-酮的纯化方法 |
JP2005337946A (ja) * | 2004-05-28 | 2005-12-08 | Kuraray Co Ltd | 6,10,14−トリメチルペンタデカ−5,9,13−トリエン−2−オンの幾何異性体の分離方法 |
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2008
- 2008-07-22 CN CN200880102256A patent/CN101778810A/zh active Pending
- 2008-07-22 EP EP08775274.7A patent/EP2188240B1/en active Active
- 2008-07-22 WO PCT/EP2008/059601 patent/WO2009019132A1/en active Application Filing
- 2008-07-22 JP JP2010519414A patent/JP5526374B2/ja active Active
- 2008-07-22 CN CN201510679497.9A patent/CN105384615A/zh active Pending
- 2008-07-22 US US12/672,276 patent/US8217203B2/en active Active
Also Published As
Publication number | Publication date |
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WO2009019132A1 (en) | 2009-02-12 |
US8217203B2 (en) | 2012-07-10 |
US20100204520A1 (en) | 2010-08-12 |
EP2188240A1 (en) | 2010-05-26 |
EP2188240B1 (en) | 2016-04-13 |
JP2010535730A (ja) | 2010-11-25 |
CN101778810A (zh) | 2010-07-14 |
CN105384615A (zh) | 2016-03-09 |
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