US20060167319A1 - Methods for the synthesis of unsaturated ketone intermediates useful for the synthesis of carotenoids - Google Patents
Methods for the synthesis of unsaturated ketone intermediates useful for the synthesis of carotenoids Download PDFInfo
- Publication number
- US20060167319A1 US20060167319A1 US11/242,609 US24260905A US2006167319A1 US 20060167319 A1 US20060167319 A1 US 20060167319A1 US 24260905 A US24260905 A US 24260905A US 2006167319 A1 US2006167319 A1 US 2006167319A1
- Authority
- US
- United States
- Prior art keywords
- compound
- carotenoids
- synthesis
- carotenoid
- solution
- 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.)
- Abandoned
Links
- 0 *C1C=C(C)C(=O)C(C)(C)C1 Chemical compound *C1C=C(C)C(=O)C(C)(C)C1 0.000 description 65
- KDVSENMOYRCKRD-BVUSFOFSSA-N C.C=CC(C)(C)C(C)(C)C.CC/C=C(\C)C(C)(C)C Chemical compound C.C=CC(C)(C)C(C)(C)C.CC/C=C(\C)C(C)(C)C KDVSENMOYRCKRD-BVUSFOFSSA-N 0.000 description 3
- YHCIKUXPWFLCFN-QHUUTLAPSA-N [H]C(=O)/C(C)=C/C=C/C(C)=C/C=C/C=C(C)/C=C/C=C(\C)C([H])=O Chemical compound [H]C(=O)/C(C)=C/C=C/C(C)=C/C=C/C=C(C)/C=C/C=C(\C)C([H])=O YHCIKUXPWFLCFN-QHUUTLAPSA-N 0.000 description 3
- DQOSYBXDYDSYJX-ZZVNVUPSSA-N C.C.C=CC(C)(C)C(C)(C)C.CC/C=C(\C)C(C)(C)C Chemical compound C.C.C=CC(C)(C)C(C)(C)C.CC/C=C(\C)C(C)(C)C DQOSYBXDYDSYJX-ZZVNVUPSSA-N 0.000 description 2
- BMIDNPXQJYOYAG-QHUUTLAPSA-N CC(/C=C/C=C(\C)CO)=C\C=C\C=C(C)\C=C\C=C(/C)CO Chemical compound CC(/C=C/C=C(\C)CO)=C\C=C\C=C(C)\C=C\C=C(/C)CO BMIDNPXQJYOYAG-QHUUTLAPSA-N 0.000 description 2
- JUXCOEPWUBCLCC-WJDWGLJXSA-N CC(=O)CCC(=O)OC/C(C)=C/CC/C(C)=C/C=C/C(C)=C/C=C/C(C)=C/C=C/C=C(C)/C=C/C=C(C)/C=C/C=C(\C)CC/C=C(\C)COC(=O)CCC(C)=O Chemical compound CC(=O)CCC(=O)OC/C(C)=C/CC/C(C)=C/C=C/C(C)=C/C=C/C(C)=C/C=C/C=C(C)/C=C/C=C(C)/C=C/C=C(\C)CC/C=C(\C)COC(=O)CCC(C)=O JUXCOEPWUBCLCC-WJDWGLJXSA-N 0.000 description 2
- OAIJSZIZWZSQBC-GYZMGTAESA-N CC(C)=CCC/C(C)=C/C=C/C(C)=C/C=C/C(C)=C/C=C/C=C(C)/C=C/C=C(C)/C=C/C=C(\C)CCC=C(C)C Chemical compound CC(C)=CCC/C(C)=C/C=C/C(C)=C/C=C/C(C)=C/C=C/C=C(C)/C=C/C=C(C)/C=C/C=C(\C)CCC=C(C)C OAIJSZIZWZSQBC-GYZMGTAESA-N 0.000 description 2
- PVBQGYKWZCRYPV-UHFFFAOYSA-N CC1=C(O)C(=O)CC(C)(C)C1=O.COC1=C(C)C(=O)C(C)(C)CC1=O.CS(C)(=O)(O)OO Chemical compound CC1=C(O)C(=O)CC(C)(C)C1=O.COC1=C(C)C(=O)C(C)(C)CC1=O.CS(C)(=O)(O)OO PVBQGYKWZCRYPV-UHFFFAOYSA-N 0.000 description 2
- JMLOUMNEOMOAGA-GZTXQBDSSA-N CC1=C2OC(C)(C)O[C@H]2CC(C)(C)C1=O.COC1=C(C)C(=O)C(C)(C)C[C@@H]1O Chemical compound CC1=C2OC(C)(C)O[C@H]2CC(C)(C)C1=O.COC1=C(C)C(=O)C(C)(C)C[C@@H]1O JMLOUMNEOMOAGA-GZTXQBDSSA-N 0.000 description 2
- ICLASYLYHJLVTR-YZIORBTBSA-N CCOC(=O)/C(C)=C/C=C/C(C)=C/C=C/C=C(C)/C=C/C=C(\C)C(=O)OCC Chemical compound CCOC(=O)/C(C)=C/C=C/C(C)=C/C=C/C=C(C)/C=C/C=C(\C)C(=O)OCC ICLASYLYHJLVTR-YZIORBTBSA-N 0.000 description 2
- VKFMOZPLJUSLLU-GQCTYLIASA-N CCOC(=O)/C(C)=C/CBr Chemical compound CCOC(=O)/C(C)=C/CBr VKFMOZPLJUSLLU-GQCTYLIASA-N 0.000 description 2
- YDWPUVHDHXXEMK-NIBSWVOWSA-N [H]C(=O)/C(C)=C/C=C/C(C)=C/C=C/C=C(C)/C=C/C=C(\C)C(C)=O Chemical compound [H]C(=O)/C(C)=C/C=C/C(C)=C/C=C/C=C(C)/C=C/C=C(\C)C(C)=O YDWPUVHDHXXEMK-NIBSWVOWSA-N 0.000 description 2
- LKFRCJJBOANVAA-UHFFFAOYSA-N B.CC1=CC(=O)CC(C)(C)C1=O Chemical compound B.CC1=CC(=O)CC(C)(C)C1=O LKFRCJJBOANVAA-UHFFFAOYSA-N 0.000 description 1
- QOKQHAFMXVOAJJ-UHFFFAOYSA-N B.COC1=C(C)C(=O)C(C)(C)CC1=O.COC1=C(C)C(=O)C(C)(C)CC1O.[NaH] Chemical compound B.COC1=C(C)C(=O)C(C)(C)CC1=O.COC1=C(C)C(=O)C(C)(C)CC1O.[NaH] QOKQHAFMXVOAJJ-UHFFFAOYSA-N 0.000 description 1
- KEVHXFVJRWETRH-SLNOCBGISA-N BrC(Br)(Br)Br.C.CCOC(=O)/C(C)=C/CO Chemical compound BrC(Br)(Br)Br.C.CCOC(=O)/C(C)=C/CO KEVHXFVJRWETRH-SLNOCBGISA-N 0.000 description 1
- FLDNRRKTIHTGRJ-YYKNYCDFSA-N BrC(Br)(Br)Br.C/C(C=O)=C\C=C\C=C(/C)C=O.CC(/C=C/C=C(\C)CO)=C\C=C\C=C(C)\C=C\C=C(/C)CO.CC(C)=C/C=C/C(C)=C/C=C/C=C(C)/C=C/C=C(\C)C=O.CCOC(=O)/C(C)=C/C=C/C(C)=C/C=C/C=C(C)/C=C/C=C(\C)C(=O)OCC.CCOC(=O)/C(C)=C/CBr.CCOC(=O)/C(C)=C/CO.CCOC(=O)/C(C)=C/CP(Br)(C1=CC=CC=C1)(C1=CC=CC=C1)C1=CC=CC=C1.CCOC(=O)C(C)=P(C1=CC=CC=C1)(C1=CC=CC=C1)C1=CC=CC=C1.CCOC(=O)C(C)Br.OC1COC(O)CO1 Chemical compound BrC(Br)(Br)Br.C/C(C=O)=C\C=C\C=C(/C)C=O.CC(/C=C/C=C(\C)CO)=C\C=C\C=C(C)\C=C\C=C(/C)CO.CC(C)=C/C=C/C(C)=C/C=C/C=C(C)/C=C/C=C(\C)C=O.CCOC(=O)/C(C)=C/C=C/C(C)=C/C=C/C=C(C)/C=C/C=C(\C)C(=O)OCC.CCOC(=O)/C(C)=C/CBr.CCOC(=O)/C(C)=C/CO.CCOC(=O)/C(C)=C/CP(Br)(C1=CC=CC=C1)(C1=CC=CC=C1)C1=CC=CC=C1.CCOC(=O)C(C)=P(C1=CC=CC=C1)(C1=CC=CC=C1)C1=CC=CC=C1.CCOC(=O)C(C)Br.OC1COC(O)CO1 FLDNRRKTIHTGRJ-YYKNYCDFSA-N 0.000 description 1
- HYEHSSLNGPYURB-KMXZHCNGSA-N C#C/C(C)=C/CC.CC#CCC.[H]C#C[H] Chemical compound C#C/C(C)=C/CC.CC#CCC.[H]C#C[H] HYEHSSLNGPYURB-KMXZHCNGSA-N 0.000 description 1
- QIVUFCBDRCOFKV-UHFFFAOYSA-N C#CC(C)(C)C=C Chemical compound C#CC(C)(C)C=C QIVUFCBDRCOFKV-UHFFFAOYSA-N 0.000 description 1
- CACZJRTZWJUMPS-UHFFFAOYSA-N C#CC(C)(C)C=C.C=CC(C)=O.[H]C#C[H] Chemical compound C#CC(C)(C)C=C.C=CC(C)=O.[H]C#C[H] CACZJRTZWJUMPS-UHFFFAOYSA-N 0.000 description 1
- FOJKZCFHTJYOFL-UHFFFAOYSA-N C#CC(C)(C=C)OC(C)OCC.C#CC(C)(O)C=C.CC1=CC=C(S(=O)(=O)O)C=C1 Chemical compound C#CC(C)(C=C)OC(C)OCC.C#CC(C)(O)C=C.CC1=CC=C(S(=O)(=O)O)C=C1 FOJKZCFHTJYOFL-UHFFFAOYSA-N 0.000 description 1
- KLFIBZQFUKAHFO-UJRZSSDVSA-N C#CC(C)(C=C)OC(C)OCC.C=CC(C)(C#CC1(O)C(C)=C[C@@H](O[Si](C)(C)C(C)(C)C)CC1(C)C)OC(C)OCC.CC1=C[C@@H](O[Si](C)(C)C(C)(C)C)CC(C)(C)C1=O Chemical compound C#CC(C)(C=C)OC(C)OCC.C=CC(C)(C#CC1(O)C(C)=C[C@@H](O[Si](C)(C)C(C)(C)C)CC1(C)C)OC(C)OCC.CC1=C[C@@H](O[Si](C)(C)C(C)(C)C)CC(C)(C)C1=O KLFIBZQFUKAHFO-UJRZSSDVSA-N 0.000 description 1
- KTYAYUCRAPYZPI-UHFFFAOYSA-N C.CC1(C)CC(=O)C2OC2(C)C1=O.CO.COC1=C(C)C(=O)C(C)(C)CC1=O Chemical compound C.CC1(C)CC(=O)C2OC2(C)C1=O.CO.COC1=C(C)C(=O)C(C)(C)CC1=O KTYAYUCRAPYZPI-UHFFFAOYSA-N 0.000 description 1
- JLDKTATZGJLQIG-UHFFFAOYSA-N C.CC1=C(O)C(=O)CC(C)(C)C1=O.CC1=CC(C)=C(OC2=C(C)C(=O)C(C)(C)CC2=O)C(C)=C1.CO.COC1=C(C)C(=O)C(C)(C)CC1=O.CO[Na].CS(=O)(=O)Cl Chemical compound C.CC1=C(O)C(=O)CC(C)(C)C1=O.CC1=CC(C)=C(OC2=C(C)C(=O)C(C)(C)CC2=O)C(C)=C1.CO.COC1=C(C)C(=O)C(C)(C)CC1=O.CO[Na].CS(=O)(=O)Cl JLDKTATZGJLQIG-UHFFFAOYSA-N 0.000 description 1
- ODBZUFXECLJCJM-UHFFFAOYSA-N C.CC1=C(O)C(=O)CC(C)(C)C1=O.CO.COC1=C(C)C(=O)C(C)(C)CC1=O Chemical compound C.CC1=C(O)C(=O)CC(C)(C)C1=O.CO.COC1=C(C)C(=O)C(C)(C)CC1=O ODBZUFXECLJCJM-UHFFFAOYSA-N 0.000 description 1
- RKCUJGXEQAKBHF-UHFFFAOYSA-N C.CC1=C(O)C(=O)CC(C)(C)C1=O.COC1=C(C)C(=O)C(C)(C)CC1=O Chemical compound C.CC1=C(O)C(=O)CC(C)(C)C1=O.COC1=C(C)C(=O)C(C)(C)CC1=O RKCUJGXEQAKBHF-UHFFFAOYSA-N 0.000 description 1
- BHWUYTHBYRZWRB-IIVSPQRNSA-N C.CC1=C2OC(C)(C)O[C@H]2CC(C)(C)C1=O.COC1=C(C)C(=O)C(C)(C)C[C@@H]1O Chemical compound C.CC1=C2OC(C)(C)O[C@H]2CC(C)(C)C1=O.COC1=C(C)C(=O)C(C)(C)C[C@@H]1O BHWUYTHBYRZWRB-IIVSPQRNSA-N 0.000 description 1
- OFKHODXKVQXQLT-VBNBHSRSSA-N C.CC1=C[C@@H](O)CC(C)(C)[C@H]1O.[2HH] Chemical compound C.CC1=C[C@@H](O)CC(C)(C)[C@H]1O.[2HH] OFKHODXKVQXQLT-VBNBHSRSSA-N 0.000 description 1
- WKDKYTWNRJBTKA-KLXURFKVSA-N C.COC1=C(C)C(=O)C(C)(C)CC1=O.COC1=C(C)C(=O)C(C)(C)C[C@@H]1O Chemical compound C.COC1=C(C)C(=O)C(C)(C)CC1=O.COC1=C(C)C(=O)C(C)(C)C[C@@H]1O WKDKYTWNRJBTKA-KLXURFKVSA-N 0.000 description 1
- PRTVHFOAYUYHCV-NSXCKHOWSA-N C/C(C=O)=C\C=C\C(C)=C\C=C\C=C(C)\C=C\C=C(/C)C=O.C/C(O)=C\CC/C(C)=C/C=C/C(C)=C/C=C/C(C)=C/C=C/C=C(C)/C=C/C=C(C)/C=C/C=C(\C)CC/C=C(\C)CO.COC(=O)/C(C)=C/CC/C(C)=C/C=C/C(C)=C/C=C/C(C)=C/C=C/C=C(C)/C=C/C=C(C)/C=C/C=C(\C)CC/C=C(\C)C(=O)OC.[HH] Chemical compound C/C(C=O)=C\C=C\C(C)=C\C=C\C=C(C)\C=C\C=C(/C)C=O.C/C(O)=C\CC/C(C)=C/C=C/C(C)=C/C=C/C(C)=C/C=C/C=C(C)/C=C/C=C(C)/C=C/C=C(\C)CC/C=C(\C)CO.COC(=O)/C(C)=C/CC/C(C)=C/C=C/C(C)=C/C=C/C(C)=C/C=C/C=C(C)/C=C/C=C(C)/C=C/C=C(\C)CC/C=C(\C)C(=O)OC.[HH] PRTVHFOAYUYHCV-NSXCKHOWSA-N 0.000 description 1
- GOUMLEKGFFBXRU-PHWOBDGISA-N C/C(C=O)=C\C=C\C=C(/C)C=O.CC1=C(/C=C/C(C)=C/C=C/C(C)=C/C=C/C=C(C)/C=C/C=C(C)/C=C/C2=C(C)C(=O)[C@@H](O)CC2(C)C)C(C)(C)C[C@H](O)C1=O.CC1=C(/C=C/C(C)=C/C[P+](C2=CC=CC=C2)(C2=CC=CC=C2)C2=CC=CC=C2)C(C)(C)C[C@H](O)C1=O.[Br-] Chemical compound C/C(C=O)=C\C=C\C=C(/C)C=O.CC1=C(/C=C/C(C)=C/C=C/C(C)=C/C=C/C=C(C)/C=C/C=C(C)/C=C/C2=C(C)C(=O)[C@@H](O)CC2(C)C)C(C)(C)C[C@H](O)C1=O.CC1=C(/C=C/C(C)=C/C[P+](C2=CC=CC=C2)(C2=CC=CC=C2)C2=CC=CC=C2)C(C)(C)C[C@H](O)C1=O.[Br-] GOUMLEKGFFBXRU-PHWOBDGISA-N 0.000 description 1
- ULAHPWLAZZVJSC-YLWKZGMQSA-N C/C(C=O)=C\C=C\C=C(/C)C=O.CCOC(=O)/C(C)=C/CP(Br)(C1=CC=CC=C1)(C1=CC=CC=C1)C1=CC=CC=C1 Chemical compound C/C(C=O)=C\C=C\C=C(/C)C=O.CCOC(=O)/C(C)=C/CP(Br)(C1=CC=CC=C1)(C1=CC=CC=C1)C1=CC=CC=C1 ULAHPWLAZZVJSC-YLWKZGMQSA-N 0.000 description 1
- VQJBNPIWRSNNEF-CNXQYKSLSA-N C1CCOC1.CC1=C[C@@H](O)CC(C)(C)C1=O.CC1=C[C@@H](O[Si](C)(C)C(C)(C)C)CC(C)(C)C1=O Chemical compound C1CCOC1.CC1=C[C@@H](O)CC(C)(C)C1=O.CC1=C[C@@H](O[Si](C)(C)C(C)(C)C)CC(C)(C)C1=O VQJBNPIWRSNNEF-CNXQYKSLSA-N 0.000 description 1
- YXTKMIHIHJKZMI-FNKGFAACSA-N C=CC(C)(C#CC1(O)C(C)=C[C@@H](O[Si](C)(C)C(C)(C)C)CC1(C)C)OC(C)OCC.C=CC(C)(C#CC1=C(C)C(=O)[C@@H](O[Si](C)(C)C(C)(C)C)CC1(C)C)OC(C)OCC Chemical compound C=CC(C)(C#CC1(O)C(C)=C[C@@H](O[Si](C)(C)C(C)(C)C)CC1(C)C)OC(C)OCC.C=CC(C)(C#CC1=C(C)C(=O)[C@@H](O[Si](C)(C)C(C)(C)C)CC1(C)C)OC(C)OCC YXTKMIHIHJKZMI-FNKGFAACSA-N 0.000 description 1
- NFZGLVGJKOSEEF-FAKNJAACSA-N C=CC(C)(C#CC1=C(C)C(=O)[C@@H](O[Si](C)(C)C(C)(C)C)CC1(C)C)OC(C)OCC.C=CC(C)(O)C#CC1=C(C)C(=O)[C@@H](O)CC1(C)C Chemical compound C=CC(C)(C#CC1=C(C)C(=O)[C@@H](O[Si](C)(C)C(C)(C)C)CC1(C)C)OC(C)OCC.C=CC(C)(O)C#CC1=C(C)C(=O)[C@@H](O)CC1(C)C NFZGLVGJKOSEEF-FAKNJAACSA-N 0.000 description 1
- ZVKAMVMVLITQPA-QILVJMBDSA-N C=CC(C)(O)/C=C/C1=C(C)C(=O)[C@@H](O)CC1(C)C.C=CC(C)(O)C#CC1=C(C)C(=O)[C@@H](O)CC1(C)C.CC1=C(/C=C/C(C)=C/C[P+](C2=CC=CC=C2)(C2=CC=CC=C2)C2=CC=CC=C2)C(C)(C)C[C@H](O)C1=O.[Br-] Chemical compound C=CC(C)(O)/C=C/C1=C(C)C(=O)[C@@H](O)CC1(C)C.C=CC(C)(O)C#CC1=C(C)C(=O)[C@@H](O)CC1(C)C.CC1=C(/C=C/C(C)=C/C[P+](C2=CC=CC=C2)(C2=CC=CC=C2)C2=CC=CC=C2)C(C)(C)C[C@H](O)C1=O.[Br-] ZVKAMVMVLITQPA-QILVJMBDSA-N 0.000 description 1
- USAGAQKFISDHBF-KVUSFRGBSA-N CC(/C=C/C=C(C)/C=C/C=C(\C)CC/C=C(\C)COP(C)(C)=O)=C\C=C\C=C(C)\C=C\C=C(C)\C=C\C=C(/C)CC/C=C(\C)COP(C)(C)=O Chemical compound CC(/C=C/C=C(C)/C=C/C=C(\C)CC/C=C(\C)COP(C)(C)=O)=C\C=C\C=C(C)\C=C\C=C(C)\C=C\C=C(/C)CC/C=C(\C)COP(C)(C)=O USAGAQKFISDHBF-KVUSFRGBSA-N 0.000 description 1
- KHVOLRZLWHZZNL-ATZSSNJPSA-N CC(/C=C/C=C(\C)C[Y])=C\C=C\C=C(C)\C=C\C=C(/C)C[Y] Chemical compound CC(/C=C/C=C(\C)C[Y])=C\C=C\C=C(C)\C=C\C=C(/C)C[Y] KHVOLRZLWHZZNL-ATZSSNJPSA-N 0.000 description 1
- BSRFZJMVFOPNKR-UHFFFAOYSA-N CC(C)(CC(C(O)=C1C)=O)C1=O Chemical compound CC(C)(CC(C(O)=C1C)=O)C1=O BSRFZJMVFOPNKR-UHFFFAOYSA-N 0.000 description 1
- AYJXHIDNNLJQDT-UHFFFAOYSA-N CC(C)(CC(C=C1C)=O)C1=O Chemical compound CC(C)(CC(C=C1C)=O)C1=O AYJXHIDNNLJQDT-UHFFFAOYSA-N 0.000 description 1
- RLDREDRZMOWDOA-QMMMGPOBSA-N CC(C)(CC(C=C1C)=O)[C@H]1O Chemical compound CC(C)(CC(C=C1C)=O)[C@H]1O RLDREDRZMOWDOA-QMMMGPOBSA-N 0.000 description 1
- CZWSBAFIAZKCRV-SSDOTTSWSA-N CC(C)(C[C@@H](C=C1C)O)C1=O Chemical compound CC(C)(C[C@@H](C=C1C)O)C1=O CZWSBAFIAZKCRV-SSDOTTSWSA-N 0.000 description 1
- VPVXKZXWZZXZTG-OAZHBLANSA-N CC(C)=CCC/C(C)=C/C[Y] Chemical compound CC(C)=CCC/C(C)=C/C[Y] VPVXKZXWZZXZTG-OAZHBLANSA-N 0.000 description 1
- UJBVTLDSWOYLBC-AYASFPIZSA-N CC(C)=O.CC1=C(/C=C/C(C)=C/C=C/C(C)=C/C=C/C=C(C)/C=C/C=C(C)/C=C/C2C(C)C(=O)[C@@H](C)CC2(C)C)C(C)(C)C[C@H](O)C1=O.CC1=C(/C=C/C(C)=C/C[P+](C2=CC=CC=C2)(C2=CC=CC=C2)C2=CC=CC=C2)C(C)(C)C[C@H](O)C1=O.CC1=C(O)C(=O)CC(C)(C)C1=O.CC1=C(O)[C@@H](O)CC(C)(C)C1=O.CC1=C2OC(C)(C)O[C@H]2CC(C)(C)C1(O)/C=C/C(C)=C/CO.CC1=C2OC(C)(C)O[C@H]2CC(C)(C)C1=O.CC1=CC(=O)CC(C)(C)C1=O.[Br-] Chemical compound CC(C)=O.CC1=C(/C=C/C(C)=C/C=C/C(C)=C/C=C/C=C(C)/C=C/C=C(C)/C=C/C2C(C)C(=O)[C@@H](C)CC2(C)C)C(C)(C)C[C@H](O)C1=O.CC1=C(/C=C/C(C)=C/C[P+](C2=CC=CC=C2)(C2=CC=CC=C2)C2=CC=CC=C2)C(C)(C)C[C@H](O)C1=O.CC1=C(O)C(=O)CC(C)(C)C1=O.CC1=C(O)[C@@H](O)CC(C)(C)C1=O.CC1=C2OC(C)(C)O[C@H]2CC(C)(C)C1(O)/C=C/C(C)=C/CO.CC1=C2OC(C)(C)O[C@H]2CC(C)(C)C1=O.CC1=CC(=O)CC(C)(C)C1=O.[Br-] UJBVTLDSWOYLBC-AYASFPIZSA-N 0.000 description 1
- ALTUHJOOGOCSMX-BGSVYHRFSA-N CC/C(C)=C/C=C/C=C(\C)CC Chemical compound CC/C(C)=C/C=C/C=C(\C)CC ALTUHJOOGOCSMX-BGSVYHRFSA-N 0.000 description 1
- VOFRQXZPJRQJIW-UHFFFAOYSA-N CC1(C(C(C)(C)C2)=O)OC1C2=O Chemical compound CC1(C(C(C)(C)C2)=O)OC1C2=O VOFRQXZPJRQJIW-UHFFFAOYSA-N 0.000 description 1
- SPAYZJGRCNAIPF-UHFFFAOYSA-N CC1(C)CC(=O)C2OC2(C)C1=O.CC1=C(O)C(=O)CC(C)(C)C1=O Chemical compound CC1(C)CC(=O)C2OC2(C)C1=O.CC1=C(O)C(=O)CC(C)(C)C1=O SPAYZJGRCNAIPF-UHFFFAOYSA-N 0.000 description 1
- BVCFHMYHLDFQIX-UHFFFAOYSA-M CC1(C)CC(=O)C2OC2(C)C1=O.CC1=C(O)C(=O)CC(C)(C)C1=O.O[Na] Chemical compound CC1(C)CC(=O)C2OC2(C)C1=O.CC1=C(O)C(=O)CC(C)(C)C1=O.O[Na] BVCFHMYHLDFQIX-UHFFFAOYSA-M 0.000 description 1
- XAXGQOPXWNYDAB-UHFFFAOYSA-N CC1(C)CC(=O)C2OC2(C)C1=O.CC1=CC(=O)CC(C)(C)C1=O Chemical compound CC1(C)CC(=O)C2OC2(C)C1=O.CC1=CC(=O)CC(C)(C)C1=O XAXGQOPXWNYDAB-UHFFFAOYSA-N 0.000 description 1
- NNPJSMBDZHDLNB-UHFFFAOYSA-N CC1(C)CC(=O)C2OC2(C)C1=O.CC1=CC(=O)CC(C)(C)C1=O.OO Chemical compound CC1(C)CC(=O)C2OC2(C)C1=O.CC1=CC(=O)CC(C)(C)C1=O.OO NNPJSMBDZHDLNB-UHFFFAOYSA-N 0.000 description 1
- UISVKQMQBDGWGR-UHFFFAOYSA-N CC1(C)CC(=O)C2OC2(C)C1=O.CO.COC1=C(C)C(=O)C(C)(C)CC1=O.CO[Na] Chemical compound CC1(C)CC(=O)C2OC2(C)C1=O.CO.COC1=C(C)C(=O)C(C)(C)CC1=O.CO[Na] UISVKQMQBDGWGR-UHFFFAOYSA-N 0.000 description 1
- SGHOCDMGSIYFIA-UHFFFAOYSA-N CC1(C)CC(=O)C2OC2(C)C1=O.COC1=C(C)C(=O)C(C)(C)CC1=O Chemical compound CC1(C)CC(=O)C2OC2(C)C1=O.COC1=C(C)C(=O)C(C)(C)CC1=O SGHOCDMGSIYFIA-UHFFFAOYSA-N 0.000 description 1
- STAIZLDUTRDGKV-FZZCSYBRSA-N CC1=C(/C=C/C(C)=C/C=C/C(C)=C/C=C/C=C(C)/C=C/C=C(C)/C=C/C2=C(C)C(=O)C(O)C(O)C2(C)C)C(C)(C)C(C)C(O)C1=O Chemical compound CC1=C(/C=C/C(C)=C/C=C/C(C)=C/C=C/C=C(C)/C=C/C=C(C)/C=C/C2=C(C)C(=O)C(O)C(O)C2(C)C)C(C)(C)C(C)C(O)C1=O STAIZLDUTRDGKV-FZZCSYBRSA-N 0.000 description 1
- MQZIGYBFDRPAKN-UWFIBFSHSA-N CC1=C(/C=C/C(C)=C/C=C/C(C)=C/C=C/C=C(C)/C=C/C=C(C)/C=C/C2=C(C)C(=O)[C@@H](O)CC2(C)C)C(C)(C)C[C@H](O)C1=O Chemical compound CC1=C(/C=C/C(C)=C/C=C/C(C)=C/C=C/C=C(C)/C=C/C=C(C)/C=C/C2=C(C)C(=O)[C@@H](O)CC2(C)C)C(C)(C)C[C@H](O)C1=O MQZIGYBFDRPAKN-UWFIBFSHSA-N 0.000 description 1
- KZYCDNDRFNRJAG-OYNNRINPSA-N CC1=C(/C=C/C(C)=C/C=C/C(C)=C/C=C/C=C(C)/C=C/C=C(C)/C=C/C2=C(C)C(C)C([Y])C(C)C2(C)C)C(C)(C)C(C)C([Y])C1C Chemical compound CC1=C(/C=C/C(C)=C/C=C/C(C)=C/C=C/C=C(C)/C=C/C=C(C)/C=C/C2=C(C)C(C)C([Y])C(C)C2(C)C)C(C)(C)C(C)C([Y])C1C KZYCDNDRFNRJAG-OYNNRINPSA-N 0.000 description 1
- GXLJMSJMXSSYQD-WEYXYWBQSA-N CC1=C(/C=C/C(C)=C/C=O)C(C)(C)CC(O)C1=O Chemical compound CC1=C(/C=C/C(C)=C/C=O)C(C)(C)CC(O)C1=O GXLJMSJMXSSYQD-WEYXYWBQSA-N 0.000 description 1
- LKEXBNIWPUQGNP-UHFFFAOYSA-N CC1=C(C)C(=O)C(C)(C)CC1=O.CC1=C(C)C(O)CC(C)(C)C1=O.CC1=C2OC(C)(C)OC2CC(C)(C)C1=O Chemical compound CC1=C(C)C(=O)C(C)(C)CC1=O.CC1=C(C)C(O)CC(C)(C)C1=O.CC1=C2OC(C)(C)OC2CC(C)(C)C1=O LKEXBNIWPUQGNP-UHFFFAOYSA-N 0.000 description 1
- FRBPOONZDUFWNF-OWJCAWTQSA-N CC1=C(C)C(=O)C(C)(C)CC1=O.CC1=C(C)[C@@H](O)CC(C)(C)C1=O.CC1=C2OC(C)(C)O[C@H]2CC(C)(C)C1=O.[C-4] Chemical compound CC1=C(C)C(=O)C(C)(C)CC1=O.CC1=C(C)[C@@H](O)CC(C)(C)C1=O.CC1=C2OC(C)(C)O[C@H]2CC(C)(C)C1=O.[C-4] FRBPOONZDUFWNF-OWJCAWTQSA-N 0.000 description 1
- PCEIDCDZLWUQGK-UHFFFAOYSA-N CC1=C(C)C(=O)C(C)(C)CC1=O.CC1=CC(=O)CC(C)(C)C1=O Chemical compound CC1=C(C)C(=O)C(C)(C)CC1=O.CC1=CC(=O)CC(C)(C)C1=O PCEIDCDZLWUQGK-UHFFFAOYSA-N 0.000 description 1
- QRWOPXUEQCDTRL-GKEHKEAQSA-M CC1=C(C)[C@@H](O)CC(C)(C)C1=O.CC1=CC=C(C(C)C)C=C1.CC1=CC=C(S(=O)(=O)N2[C@@H](C3=CC=CC=C3)[C@H](C3=CC=CC=C3)N[Ru@]2(C)Cl)C=C1.COC1=C(C)C(=O)C(C)(C)CC1=O Chemical compound CC1=C(C)[C@@H](O)CC(C)(C)C1=O.CC1=CC=C(C(C)C)C=C1.CC1=CC=C(S(=O)(=O)N2[C@@H](C3=CC=CC=C3)[C@H](C3=CC=CC=C3)N[Ru@]2(C)Cl)C=C1.COC1=C(C)C(=O)C(C)(C)CC1=O QRWOPXUEQCDTRL-GKEHKEAQSA-M 0.000 description 1
- XBNFDXPRHKFBNC-WDBKTSHHSA-N CC1=C(C)[C@@H](O)CC(C)(C)C1=O.COC1=C(C)C(=O)C(C)(C)CC1=O Chemical compound CC1=C(C)[C@@H](O)CC(C)(C)C1=O.COC1=C(C)C(=O)C(C)(C)CC1=O XBNFDXPRHKFBNC-WDBKTSHHSA-N 0.000 description 1
- UAYUDVYNKVUCIN-QSOZJIPRSA-N CC1=CC(=O)CC(C)(C)C1=O.CC1=CC(=O)CC(C)(C)[C@H]1O.C[C@H](N)[C@H](O)C1=CC=CC=C1 Chemical compound CC1=CC(=O)CC(C)(C)C1=O.CC1=CC(=O)CC(C)(C)[C@H]1O.C[C@H](N)[C@H](O)C1=CC=CC=C1 UAYUDVYNKVUCIN-QSOZJIPRSA-N 0.000 description 1
- PXNSYCYXDLNDDW-CTWWJBIBSA-N CC1=CC(=O)CC(C)(C)C1=O.CC1=C[C@@H](C)CC(C)(C)C1=O.CC1=C[C@@H](O)CC(C)(C)C1=O Chemical compound CC1=CC(=O)CC(C)(C)C1=O.CC1=C[C@@H](C)CC(C)(C)C1=O.CC1=C[C@@H](O)CC(C)(C)C1=O PXNSYCYXDLNDDW-CTWWJBIBSA-N 0.000 description 1
- JLZFYMOPHWAASQ-QMMMGPOBSA-N CC1=CC(=O)CC(C)(C)[C@H]1C Chemical compound CC1=CC(=O)CC(C)(C)[C@H]1C JLZFYMOPHWAASQ-QMMMGPOBSA-N 0.000 description 1
- RIZFCAVZUJPSAR-NLDWQNQMSA-N CC1=CC(=O)CC(C)(C)[C@H]1O.CC1=C[C@@H](O)CC(C)(C)[C@H]1O Chemical compound CC1=CC(=O)CC(C)(C)[C@H]1O.CC1=C[C@@H](O)CC(C)(C)[C@H]1O RIZFCAVZUJPSAR-NLDWQNQMSA-N 0.000 description 1
- IDOKJIKFUJLBES-GOPWMECQSA-M CC1=CC=C(C(C)C)C=C1.CC1=CC=C(S(=O)(=O)N2[C@@H](C3=CC=CC=C3)[C@H](C3=CC=CC=C3)N[Ru@]2(C)Cl)C=C1 Chemical compound CC1=CC=C(C(C)C)C=C1.CC1=CC=C(S(=O)(=O)N2[C@@H](C3=CC=CC=C3)[C@H](C3=CC=CC=C3)N[Ru@]2(C)Cl)C=C1 IDOKJIKFUJLBES-GOPWMECQSA-M 0.000 description 1
- WOFKWEHTMFXTGO-JVAWPFSQSA-M CC1=CC=C(C(C)C)C=C1.CC1=CC=C(S(=O)(=O)N2[C@@H](C3=CC=CC=C3)[C@H](C3=CC=CC=C3)N[Ru@]2(C)Cl)C=C1.COC1=C(C)C(=O)C(C)(C)CC1=O.COC1=C(C)C(=O)C(C)(C)C[C@@H]1O Chemical compound CC1=CC=C(C(C)C)C=C1.CC1=CC=C(S(=O)(=O)N2[C@@H](C3=CC=CC=C3)[C@H](C3=CC=CC=C3)N[Ru@]2(C)Cl)C=C1.COC1=C(C)C(=O)C(C)(C)CC1=O.COC1=C(C)C(=O)C(C)(C)C[C@@H]1O WOFKWEHTMFXTGO-JVAWPFSQSA-M 0.000 description 1
- JHNSOCUZCNYJJC-KPYSKOJTSA-N CC1=C[C@@H](O)CC(C)(C)[C@H]1O.CC1=C[C@@H](O[Si](C)(C)C(C)(C)C)CC(C)(C)[C@H]1O Chemical compound CC1=C[C@@H](O)CC(C)(C)[C@H]1O.CC1=C[C@@H](O[Si](C)(C)C(C)(C)C)CC(C)(C)[C@H]1O JHNSOCUZCNYJJC-KPYSKOJTSA-N 0.000 description 1
- POOOTPCCECOICT-GFCCVEGCSA-N CC1=C[C@@H](O[Si](C)(C)C(C)(C)C)CC(C)(C)C1=O Chemical compound CC1=C[C@@H](O[Si](C)(C)C(C)(C)C)CC(C)(C)C1=O POOOTPCCECOICT-GFCCVEGCSA-N 0.000 description 1
- AHPZDZDQCSXHPM-BQLTXLDDSA-N CC1=C[C@@H](O[Si](C)(C)C(C)(C)C)CC(C)(C)C1=O.CC1=C[C@@H](O[Si](C)(C)C(C)(C)C)CC(C)(C)[C@H]1O Chemical compound CC1=C[C@@H](O[Si](C)(C)C(C)(C)C)CC(C)(C)C1=O.CC1=C[C@@H](O[Si](C)(C)C(C)(C)C)CC(C)(C)[C@H]1O AHPZDZDQCSXHPM-BQLTXLDDSA-N 0.000 description 1
- HZYYGRVQBOFLQP-UONOGXRCSA-N CC1=C[C@@H](O[Si](C)(C)C(C)(C)C)CC(C)(C)[C@H]1C Chemical compound CC1=C[C@@H](O[Si](C)(C)C(C)(C)C)CC(C)(C)[C@H]1C HZYYGRVQBOFLQP-UONOGXRCSA-N 0.000 description 1
- PLKAMKXQJQQXJV-GQCTYLIASA-N CCOC(=O)/C(C)=C/CO Chemical compound CCOC(=O)/C(C)=C/CO PLKAMKXQJQQXJV-GQCTYLIASA-N 0.000 description 1
- LQZNNYLKVXQNBT-XUTLUUPISA-N CCOC(=O)/C(C)=C/CP(Br)(C1=CC=CC=C1)(C1=CC=CC=C1)C1=CC=CC=C1 Chemical compound CCOC(=O)/C(C)=C/CP(Br)(C1=CC=CC=C1)(C1=CC=CC=C1)C1=CC=CC=C1 LQZNNYLKVXQNBT-XUTLUUPISA-N 0.000 description 1
- BEJDDQUWNKNBEW-UHFFFAOYSA-N CCOC(=O)C(C)=P(C1=CC=CC=C1)(C1=CC=CC=C1)C1=CC=CC=C1.CCOC(=O)C(C)Br Chemical compound CCOC(=O)C(C)=P(C1=CC=CC=C1)(C1=CC=CC=C1)C1=CC=CC=C1.CCOC(=O)C(C)Br BEJDDQUWNKNBEW-UHFFFAOYSA-N 0.000 description 1
- XLKDPIPGOFBPAS-UHFFFAOYSA-N CCOC(=O)C(C)=P(C1=CC=CC=C1)(C1=CC=CC=C1)C1=CC=CC=C1.OC1COC(O)CO1 Chemical compound CCOC(=O)C(C)=P(C1=CC=CC=C1)(C1=CC=CC=C1)C1=CC=CC=C1.OC1COC(O)CO1 XLKDPIPGOFBPAS-UHFFFAOYSA-N 0.000 description 1
- HSMCNUFVDLMIHZ-FJXQXJEOSA-N COC1=C(C)C(=O)C(C)(C)CC1=O.COC1=C(C)C(=O)C(C)(C)C[C@@H]1O Chemical compound COC1=C(C)C(=O)C(C)(C)CC1=O.COC1=C(C)C(=O)C(C)(C)C[C@@H]1O HSMCNUFVDLMIHZ-FJXQXJEOSA-N 0.000 description 1
- DLNKOYKMWOXYQA-CBAPKCEASA-N C[C@@H]([C@@H](c1ccccc1)O)N Chemical compound C[C@@H]([C@@H](c1ccccc1)O)N DLNKOYKMWOXYQA-CBAPKCEASA-N 0.000 description 1
- ATFVTAOSZBVGHC-UHFFFAOYSA-N OC1COC(O)CO1 Chemical compound OC1COC(O)CO1 ATFVTAOSZBVGHC-UHFFFAOYSA-N 0.000 description 1
- AYODHZHFDRRQEZ-XLKYRCCQSA-N [H]C(=O)/C(C)=C/C=C/C=C(\C)C([H])=O Chemical compound [H]C(=O)/C(C)=C/C=C/C=C(\C)C([H])=O AYODHZHFDRRQEZ-XLKYRCCQSA-N 0.000 description 1
- WTEVQBCEXWBHNA-JXMROGBWSA-N [H]C(=O)/C=C(\C)CCC=C(C)C Chemical compound [H]C(=O)/C=C(\C)CCC=C(C)C WTEVQBCEXWBHNA-JXMROGBWSA-N 0.000 description 1
- BTDCWVSWXWVYPY-UQFPWVGQSA-N [H]C1C(=O)C(C)=C(/C=C/C(C)=C/C=C/C(C)=C/C=C/C=C(C)/C=C/C=C(C)/C=C/C2=C(C)C(=O)C(C)C([H])C2(C)C)C(C)(C)C1[H] Chemical compound [H]C1C(=O)C(C)=C(/C=C/C(C)=C/C=C/C(C)=C/C=C/C=C(C)/C=C/C=C(C)/C=C/C2=C(C)C(=O)C(C)C([H])C2(C)C)C(C)(C)C1[H] BTDCWVSWXWVYPY-UQFPWVGQSA-N 0.000 description 1
- POTXOFBBPGHRRO-OIRRSCHYSA-N [H]C1C(=O)C(C)=C(/C=C/C(C)=C/C=C/C(C)=C/C=C/C=C(C)/C=C/C=C(C)/C=C/C2=C(C)C(=O)C([H])C(O)C2(C)C)C(C)(C)C1C Chemical compound [H]C1C(=O)C(C)=C(/C=C/C(C)=C/C=C/C(C)=C/C=C/C=C(C)/C=C/C=C(C)/C=C/C2=C(C)C(=O)C([H])C(O)C2(C)C)C(C)(C)C1C POTXOFBBPGHRRO-OIRRSCHYSA-N 0.000 description 1
- YFDKYEHAKZRMTI-OIRRSCHYSA-N [H]C1C(C)C(=O)C(C)=C(/C=C/C(C)=C/C=C/C(C)=C/C=C/C=C(C)/C=C/C=C(C)/C=C/C2=C(C)C(=O)C(O)C([H])C2(C)C)C1(C)C Chemical compound [H]C1C(C)C(=O)C(C)=C(/C=C/C(C)=C/C=C/C(C)=C/C=C/C=C(C)/C=C/C=C(C)/C=C/C2=C(C)C(=O)C(O)C([H])C2(C)C)C1(C)C YFDKYEHAKZRMTI-OIRRSCHYSA-N 0.000 description 1
- JQEUDOQYHFBJRD-OIRRSCHYSA-N [H]C1C(C)C(O)C(C)=C(/C=C/C(C)=C/C=C/C(C)=C/C=C/C=C(C)/C=C/C=C(C)/C=C/C2=C(C)C(O)C(O)C([H])C2(C)C)C1(C)C Chemical compound [H]C1C(C)C(O)C(C)=C(/C=C/C(C)=C/C=C/C(C)=C/C=C/C=C(C)/C=C/C=C(C)/C=C/C2=C(C)C(O)C(O)C([H])C2(C)C)C1(C)C JQEUDOQYHFBJRD-OIRRSCHYSA-N 0.000 description 1
- NCLIEZTYUHUSSJ-UQFPWVGQSA-N [H]C1C(O)C(C)=C(/C=C/C(C)=C/C=C/C(C)=C/C=C/C=C(C)/C=C/C=C(C)/C=C/C2=C(C)C(O)C(C)C([H])C2(C)C)C(C)(C)C1[H] Chemical compound [H]C1C(O)C(C)=C(/C=C/C(C)=C/C=C/C(C)=C/C=C/C=C(C)/C=C/C=C(C)/C=C/C2=C(C)C(O)C(C)C([H])C2(C)C)C(C)(C)C1[H] NCLIEZTYUHUSSJ-UQFPWVGQSA-N 0.000 description 1
- VMKAFJQFKBASMU-QGZVFWFLSA-N [H][C@]12CCCN1B(C)OC2(C1=CC=CC=C1)C1=CC=CC=C1 Chemical compound [H][C@]12CCCN1B(C)OC2(C1=CC=CC=C1)C1=CC=CC=C1 VMKAFJQFKBASMU-QGZVFWFLSA-N 0.000 description 1
Images
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C403/00—Derivatives of cyclohexane or of a cyclohexene or of cyclohexadiene, having a side-chain containing an acyclic unsaturated part of at least four carbon atoms, this part being directly attached to the cyclohexane or cyclohexene or cyclohexadiene rings, e.g. vitamin A, beta-carotene, beta-ionone
- C07C403/24—Derivatives of cyclohexane or of a cyclohexene or of cyclohexadiene, having a side-chain containing an acyclic unsaturated part of at least four carbon atoms, this part being directly attached to the cyclohexane or cyclohexene or cyclohexadiene rings, e.g. vitamin A, beta-carotene, beta-ionone having side-chains substituted by six-membered non-aromatic rings, e.g. beta-carotene
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C29/00—Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom not belonging to a six-membered aromatic ring
- C07C29/132—Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom not belonging to a six-membered aromatic ring by reduction of an oxygen containing functional group
- C07C29/136—Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom not belonging to a six-membered aromatic ring by reduction of an oxygen containing functional group of >C=O containing groups, e.g. —COOH
- C07C29/143—Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom not belonging to a six-membered aromatic ring by reduction of an oxygen containing functional group of >C=O containing groups, e.g. —COOH of ketones
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C403/00—Derivatives of cyclohexane or of a cyclohexene or of cyclohexadiene, having a side-chain containing an acyclic unsaturated part of at least four carbon atoms, this part being directly attached to the cyclohexane or cyclohexene or cyclohexadiene rings, e.g. vitamin A, beta-carotene, beta-ionone
- C07C403/06—Derivatives of cyclohexane or of a cyclohexene or of cyclohexadiene, having a side-chain containing an acyclic unsaturated part of at least four carbon atoms, this part being directly attached to the cyclohexane or cyclohexene or cyclohexadiene rings, e.g. vitamin A, beta-carotene, beta-ionone having side-chains substituted by singly-bound oxygen atoms
- C07C403/08—Derivatives of cyclohexane or of a cyclohexene or of cyclohexadiene, having a side-chain containing an acyclic unsaturated part of at least four carbon atoms, this part being directly attached to the cyclohexane or cyclohexene or cyclohexadiene rings, e.g. vitamin A, beta-carotene, beta-ionone having side-chains substituted by singly-bound oxygen atoms by hydroxy groups
-
- 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
- C07C45/27—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by oxidation
- C07C45/29—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by oxidation of hydroxy groups
- C07C45/298—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by oxidation of hydroxy groups with manganese derivatives
-
- 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
-
- 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
- C07C45/61—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by reactions not involving the formation of >C = O groups
-
- 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
- C07C45/61—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by reactions not involving the formation of >C = O groups
- C07C45/64—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by reactions not involving the formation of >C = O groups by introduction of functional groups containing oxygen only in singly bound form
-
- 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
- C07C45/61—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by reactions not involving the formation of >C = O groups
- C07C45/67—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by reactions not involving the formation of >C = O groups by isomerisation; by change of size of the carbon skeleton
- C07C45/673—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by reactions not involving the formation of >C = O groups by isomerisation; by change of size of the carbon skeleton by change of size of the carbon skeleton
-
- 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
- C07C45/61—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by reactions not involving the formation of >C = O groups
- C07C45/67—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by reactions not involving the formation of >C = O groups by isomerisation; by change of size of the carbon skeleton
- C07C45/68—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by reactions not involving the formation of >C = O groups by isomerisation; by change of size of the carbon skeleton by increase in the number of carbon atoms
- C07C45/70—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by reactions not involving the formation of >C = O groups by isomerisation; by change of size of the carbon skeleton by increase in the number of carbon atoms by reaction with functional groups containing oxygen only in singly bound form
-
- 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
- C07C45/61—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by reactions not involving the formation of >C = O groups
- C07C45/67—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by reactions not involving the formation of >C = O groups by isomerisation; by change of size of the carbon skeleton
- C07C45/68—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by reactions not involving the formation of >C = O groups by isomerisation; by change of size of the carbon skeleton by increase in the number of carbon atoms
- C07C45/70—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by reactions not involving the formation of >C = O groups by isomerisation; by change of size of the carbon skeleton by increase in the number of carbon atoms by reaction with functional groups containing oxygen only in singly bound form
- C07C45/71—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by reactions not involving the formation of >C = O groups by isomerisation; by change of size of the carbon skeleton by increase in the number of carbon atoms by reaction with functional groups containing oxygen only in singly bound form being hydroxy groups
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C47/00—Compounds having —CHO groups
- C07C47/20—Unsaturated compounds having —CHO groups bound to acyclic carbon atoms
- C07C47/21—Unsaturated compounds having —CHO groups bound to acyclic carbon atoms with only carbon-to-carbon double bonds as unsaturation
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C49/00—Ketones; Ketenes; Dimeric ketenes; Ketonic chelates
- C07C49/587—Unsaturated compounds containing a keto groups being part of a ring
- C07C49/703—Unsaturated compounds containing a keto groups being part of a ring containing hydroxy groups
- C07C49/713—Unsaturated compounds containing a keto groups being part of a ring containing hydroxy groups a keto group being part of a six-membered ring
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C49/00—Ketones; Ketenes; Dimeric ketenes; Ketonic chelates
- C07C49/587—Unsaturated compounds containing a keto groups being part of a ring
- C07C49/753—Unsaturated compounds containing a keto groups being part of a ring containing ether groups, groups, groups, or groups
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D319/00—Heterocyclic compounds containing six-membered rings having two oxygen atoms as the only ring hetero atoms
- C07D319/04—1,3-Dioxanes; Hydrogenated 1,3-dioxanes
- C07D319/06—1,3-Dioxanes; Hydrogenated 1,3-dioxanes not condensed with other rings
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
- C07F7/00—Compounds containing elements of Groups 4 or 14 of the Periodic System
- C07F7/02—Silicon compounds
- C07F7/08—Compounds having one or more C—Si linkages
- C07F7/18—Compounds having one or more C—Si linkages as well as one or more C—O—Si linkages
- C07F7/1804—Compounds having Si-O-C linkages
- C07F7/1872—Preparation; Treatments not provided for in C07F7/20
- C07F7/188—Preparation; Treatments not provided for in C07F7/20 by reactions involving the formation of Si-O linkages
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
- C07F7/00—Compounds containing elements of Groups 4 or 14 of the Periodic System
- C07F7/02—Silicon compounds
- C07F7/08—Compounds having one or more C—Si linkages
- C07F7/18—Compounds having one or more C—Si linkages as well as one or more C—O—Si linkages
- C07F7/1804—Compounds having Si-O-C linkages
- C07F7/1872—Preparation; Treatments not provided for in C07F7/20
- C07F7/1892—Preparation; Treatments not provided for in C07F7/20 by reactions not provided for in C07F7/1876 - C07F7/1888
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
- C07F9/00—Compounds containing elements of Groups 5 or 15 of the Periodic System
- C07F9/02—Phosphorus compounds
- C07F9/06—Phosphorus compounds without P—C bonds
- C07F9/08—Esters of oxyacids of phosphorus
- C07F9/09—Esters of phosphoric acids
- C07F9/113—Esters of phosphoric acids with unsaturated acyclic alcohols
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
- C07F9/00—Compounds containing elements of Groups 5 or 15 of the Periodic System
- C07F9/02—Phosphorus compounds
- C07F9/28—Phosphorus compounds with one or more P—C bonds
- C07F9/54—Quaternary phosphonium compounds
- C07F9/5442—Aromatic phosphonium compounds (P-C aromatic linkage)
-
- C—CHEMISTRY; METALLURGY
- C12—BIOCHEMISTRY; BEER; SPIRITS; WINE; VINEGAR; MICROBIOLOGY; ENZYMOLOGY; MUTATION OR GENETIC ENGINEERING
- C12P—FERMENTATION OR ENZYME-USING PROCESSES TO SYNTHESISE A DESIRED CHEMICAL COMPOUND OR COMPOSITION OR TO SEPARATE OPTICAL ISOMERS FROM A RACEMIC MIXTURE
- C12P23/00—Preparation of compounds containing a cyclohexene ring having an unsaturated side chain containing at least ten carbon atoms bound by conjugated double bonds, e.g. carotenes
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07B—GENERAL METHODS OF ORGANIC CHEMISTRY; APPARATUS THEREFOR
- C07B2200/00—Indexing scheme relating to specific properties of organic compounds
- C07B2200/07—Optical isomers
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07B—GENERAL METHODS OF ORGANIC CHEMISTRY; APPARATUS THEREFOR
- C07B2200/00—Indexing scheme relating to specific properties of organic compounds
- C07B2200/09—Geometrical isomers
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C2601/00—Systems containing only non-condensed rings
- C07C2601/12—Systems containing only non-condensed rings with a six-membered ring
- C07C2601/16—Systems containing only non-condensed rings with a six-membered ring the ring being unsaturated
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Life Sciences & Earth Sciences (AREA)
- Health & Medical Sciences (AREA)
- Biochemistry (AREA)
- General Health & Medical Sciences (AREA)
- Engineering & Computer Science (AREA)
- Molecular Biology (AREA)
- Wood Science & Technology (AREA)
- Zoology (AREA)
- Biotechnology (AREA)
- General Chemical & Material Sciences (AREA)
- Microbiology (AREA)
- Bioinformatics & Cheminformatics (AREA)
- General Engineering & Computer Science (AREA)
- Genetics & Genomics (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Priority Applications (1)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
US11/242,609 US20060167319A1 (en) | 2004-10-01 | 2005-10-03 | Methods for the synthesis of unsaturated ketone intermediates useful for the synthesis of carotenoids |
Applications Claiming Priority (8)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
US61503204P | 2004-10-01 | 2004-10-01 | |
US67595705P | 2005-04-29 | 2005-04-29 | |
US69151805P | 2005-06-17 | 2005-06-17 | |
US69268205P | 2005-06-21 | 2005-06-21 | |
US69965305P | 2005-07-15 | 2005-07-15 | |
US70238005P | 2005-07-26 | 2005-07-26 | |
US71235005P | 2005-08-30 | 2005-08-30 | |
US11/242,609 US20060167319A1 (en) | 2004-10-01 | 2005-10-03 | Methods for the synthesis of unsaturated ketone intermediates useful for the synthesis of carotenoids |
Publications (1)
Publication Number | Publication Date |
---|---|
US20060167319A1 true US20060167319A1 (en) | 2006-07-27 |
Family
ID=36042942
Family Applications (8)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
US11/242,609 Abandoned US20060167319A1 (en) | 2004-10-01 | 2005-10-03 | Methods for the synthesis of unsaturated ketone intermediates useful for the synthesis of carotenoids |
US11/242,615 Abandoned US20060155150A1 (en) | 2004-10-01 | 2005-10-03 | Methods for the synthesis of lutein |
US11/242,627 Abandoned US20060111580A1 (en) | 2004-10-01 | 2005-10-03 | Methods for the synthesis of chiral dihydroxy ketone intermediates useful for the chiral synthesis of carotenoids |
US11/242,591 Abandoned US20060088904A1 (en) | 2004-10-01 | 2005-10-03 | Methods for the synthesis of astaxanthin |
US11/242,645 Abandoned US20060183185A1 (en) | 2004-10-01 | 2005-10-03 | Method for the synthesis of astaxanthin |
US11/242,641 Abandoned US20060178538A1 (en) | 2004-10-01 | 2005-10-03 | Methods for the synthesis of chiral dihydroxy intermediates useful for the chiral synthesis of carotenoids |
US11/242,639 Abandoned US20060088905A1 (en) | 2004-10-01 | 2005-10-03 | Methods for the synthesis of zeazanthin |
US11/242,643 Active US7247752B2 (en) | 2004-10-01 | 2005-10-03 | Methods for the synthesis of astaxanthin |
Family Applications After (7)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
US11/242,615 Abandoned US20060155150A1 (en) | 2004-10-01 | 2005-10-03 | Methods for the synthesis of lutein |
US11/242,627 Abandoned US20060111580A1 (en) | 2004-10-01 | 2005-10-03 | Methods for the synthesis of chiral dihydroxy ketone intermediates useful for the chiral synthesis of carotenoids |
US11/242,591 Abandoned US20060088904A1 (en) | 2004-10-01 | 2005-10-03 | Methods for the synthesis of astaxanthin |
US11/242,645 Abandoned US20060183185A1 (en) | 2004-10-01 | 2005-10-03 | Method for the synthesis of astaxanthin |
US11/242,641 Abandoned US20060178538A1 (en) | 2004-10-01 | 2005-10-03 | Methods for the synthesis of chiral dihydroxy intermediates useful for the chiral synthesis of carotenoids |
US11/242,639 Abandoned US20060088905A1 (en) | 2004-10-01 | 2005-10-03 | Methods for the synthesis of zeazanthin |
US11/242,643 Active US7247752B2 (en) | 2004-10-01 | 2005-10-03 | Methods for the synthesis of astaxanthin |
Country Status (2)
Country | Link |
---|---|
US (8) | US20060167319A1 (US20060167319A1-20060727-C00027.png) |
WO (1) | WO2006039685A2 (US20060167319A1-20060727-C00027.png) |
Cited By (9)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US20050009930A1 (en) * | 2002-07-29 | 2005-01-13 | Lockwood Samuel Fournier | Carotenoid analogs or derivatives for controlling connexin 43 expression |
US20050037995A1 (en) * | 2002-07-29 | 2005-02-17 | Lockwood Samuel Fournier | Carotenoid ester analogs or derivatives for the inhibition and amelioration of ischemic reperfusion injury |
US20050065096A1 (en) * | 2002-07-29 | 2005-03-24 | Lockwood Samuel Fournier | Pharmaceutical compositions including carotenoid ether analogs or derivatives for the inhibition and amelioration of disease |
US20050090469A1 (en) * | 2002-07-29 | 2005-04-28 | Lockwood Samuel F. | Carotenoid ester analogs or derivatives for the inhibition and amelioration of liver disease |
US20050113372A1 (en) * | 2002-07-29 | 2005-05-26 | Lockwood Samuel F. | Carotenoid analogs or derivatives for the inhibition and amelioration of disease |
US20060088905A1 (en) * | 2004-10-01 | 2006-04-27 | Lockwood Samuel F | Methods for the synthesis of zeazanthin |
US20090099061A1 (en) * | 2006-01-27 | 2009-04-16 | Foss Bente J | Synthesis of carotenoid analogs or derivatives with improved antioxidant characteristics |
US20090124574A1 (en) * | 2007-03-23 | 2009-05-14 | Lockwood Samuel F | Carotenoid analogs and derivatives for the prevention of platelet aggregation |
CN101906445A (zh) * | 2010-06-18 | 2010-12-08 | 西南大学 | 2h-1-苯并吡喃-2-酮衍生物的合成方法 |
Families Citing this family (34)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
NZ535323A (en) | 2002-02-25 | 2008-02-29 | Diffusion Pharmaceuticals Llc | Bipolar trans carotenoid salts and their uses |
US7759506B2 (en) | 2002-02-25 | 2010-07-20 | Diffusion Pharmaceuticals Llc | Bipolar trans carotenoid salts and their uses |
US20050059635A1 (en) * | 2002-07-29 | 2005-03-17 | Lockwood Samuel Fournier | Carotenoid ester analogs or derivatives for controlling C-reactive protein levels |
US20050059659A1 (en) * | 2002-07-29 | 2005-03-17 | Lockwood Samuel Fournier | Carotenoid analogs or derivatives for controlling C-reactive protein levels |
US20050148517A1 (en) * | 2002-07-29 | 2005-07-07 | Lockwood Samuel F. | Carotenoid ether analogs or derivatives for controlling connexin 43 expression |
US20050049248A1 (en) * | 2002-07-29 | 2005-03-03 | Lockwood Samuel Fournier | Carotenoid ether analogs or derivatives for controlling C-reactive protein levels |
EP2540696B1 (en) | 2005-02-24 | 2020-01-01 | Diffusion Pharmaceuticals LLC | Trans carotenoids, formulation and uses |
WO2006119125A2 (en) * | 2005-04-29 | 2006-11-09 | Cardax Pharmaceuticals, Inc. | Methods for synthesis of carotenoids, including analogs, derivatives, and synthetic and biological intermediates |
US20080221377A1 (en) * | 2006-06-16 | 2008-09-11 | Lockwood Samuel F | Methods for synthesis of carotenoids, including analogs, derivatives, and synthetic and biological intermediates |
CN101148433B (zh) * | 2006-09-20 | 2011-01-12 | 浙江医药股份有限公司新昌制药厂 | 十五碳醇的合成方法 |
CN101646642A (zh) * | 2007-03-28 | 2010-02-10 | 巴斯夫欧洲公司 | 对映选择性制备光学活性4-羟基-2,6,6-三甲基环己-2-烯酮衍生物的方法 |
JP2011502125A (ja) | 2007-10-31 | 2011-01-20 | ディフュージョン・ファーマシューティカルズ・エルエルシー | 小分子拡散を促進する新しい種類の治療法 |
EP2130833A1 (en) | 2008-06-05 | 2009-12-09 | DSM IP Assets B.V. | Process for the preparation of zeacarotenes |
CA2765697C (en) | 2009-06-22 | 2019-11-12 | Diffusion Pharmaceuticals Llc | Diffusion enhancing compounds and their use alone or with thrombolytics |
US9913810B2 (en) | 2009-07-23 | 2018-03-13 | U.S. Nutraceuticals, LLC | Composition and method to alleviate joint pain using phospholipids and astaxanthin |
US8557275B2 (en) | 2009-07-23 | 2013-10-15 | U.S. Nutraceuticals, LLC | Composition and method to alleviate joint pain using a mixture of fish oil and fish oil derived, choline based, phospholipid bound fatty acid mixture including polyunsaturated EPA and DHA |
US9238043B2 (en) | 2009-07-23 | 2016-01-19 | U.S. Nutraceuticals, LLC | Composition and method to alleviate joint pain using algae based oils |
US8481072B2 (en) * | 2009-07-23 | 2013-07-09 | U.S. Nutraceuticals, LLC | Composition and method to alleviate joint pain |
US9402857B2 (en) | 2009-07-23 | 2016-08-02 | U.S. Nutraceuticals, LLC | Composition and method to alleviate joint pain using low molecular weight hyaluronic acid and astaxanthin |
US9216164B2 (en) | 2009-07-23 | 2015-12-22 | U.S. Nutraceuticals, LLC | Composition and method to alleviate joint pain using a mixture of fish oil and fish oil derived, choline based, phospholipid bound fatty acid mixture including polyunsaturated EPA and DHA |
US9399047B2 (en) | 2009-07-23 | 2016-07-26 | U.S. Nutraceuticals, LLC | Composition and method to alleviate joint pain using phospholipids and roe extract |
AU2011262361A1 (en) | 2010-06-02 | 2013-01-10 | Diffusion Pharmaceuticals Llc | Oral formulations of bipolar trans carotenoids |
PE20170706A1 (es) | 2014-07-08 | 2017-05-21 | Valent Biosciences Corp | Derivados del acido abscisico sustituido en 3' |
TW201619112A (zh) * | 2014-07-17 | 2016-06-01 | 國立臺灣大學 | 4-氧代-2-環己烯酮及6-氧代-2-環己烯酮化合物之組合物及製備方法 |
WO2016023772A1 (de) | 2014-08-12 | 2016-02-18 | Basf Se | Verfahren zur herstellung zyklischer alpha-ketoalkohole aus zyklischen alpha-ketoenolen |
WO2016023732A1 (de) * | 2014-08-12 | 2016-02-18 | Basf Se | Verfahren zur herstellung von astaxanthin aus astacin |
CN105541573B (zh) * | 2016-01-19 | 2017-11-24 | 四川大学 | 一种制备2,6,11,15‑四甲基‑2,4,6,8,10,12,14‑十六碳七烯二醛的方法 |
CN115089569A (zh) | 2016-03-24 | 2022-09-23 | 扩散药品有限公司 | 双极性反式类胡萝卜素连同化疗和放射治疗在治疗癌症中的用途 |
CN106520715B (zh) * | 2016-10-17 | 2019-06-28 | 浙江大学 | 一种短链脱氢酶及其基因、重组表达载体、基因工程菌及其在虾青素手性中间体合成中的应用 |
CN110088094A (zh) * | 2016-12-19 | 2019-08-02 | 巴斯夫欧洲公司 | 制备立体异构纯c9-缩醛的方法 |
CN110121489A (zh) | 2016-12-19 | 2019-08-13 | 巴斯夫欧洲公司 | 制备(4s)-或(4r)-3,4-二羟基-2,6,6-三甲基环己-2-烯酮的方法 |
CN107445791A (zh) * | 2017-07-31 | 2017-12-08 | 肇庆巨元生化有限公司 | 一种番茄红素的制备方法 |
CN114573488A (zh) * | 2020-12-02 | 2022-06-03 | 中国科学院大连化学物理研究所 | 一种利用制备色谱对雨生红球藻来源的虾青素进行分离纯化的方法 |
CN114369048B (zh) * | 2021-12-21 | 2023-12-26 | 上虞新和成生物化工有限公司 | 一种催化合成虾青素的方法 |
Citations (57)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US3206316A (en) * | 1960-10-17 | 1965-09-14 | Hoffmann La Roche | Water dispersible carotenoid preparations and processes thereof |
US3354218A (en) * | 1963-05-10 | 1967-11-21 | Hoffmann La Roche | Process for preparing 4-(2, 6, 6-trimethyl-4-methoxy-1-cyclohexen-1-yl)-3-buten-2-one |
US3755422A (en) * | 1970-01-15 | 1973-08-28 | Rhone Poulenc Sa | Preparation of carotenoid compounds |
US3989757A (en) * | 1973-08-29 | 1976-11-02 | Hoffmann-La Roche Inc. | Isomerizing cis-carotenoids to all-trans-carotenoids |
US4245109A (en) * | 1978-06-02 | 1981-01-13 | Hoffmann-La Roche Inc. | Process for producing astaxanthin |
US4283559A (en) * | 1978-06-02 | 1981-08-11 | Hoffmann-La Roche Inc. | Process for the manufacture of cyclohexene derivatives |
US4435427A (en) * | 1980-12-19 | 1984-03-06 | Basf Aktiengesellschaft | Stable injectable β-carotene micellar solutions and their preparation |
US4585885A (en) * | 1982-08-20 | 1986-04-29 | Hoffmann-La Roche Inc. | Cyclohexenone derivatives and process for making same |
US4952716A (en) * | 1987-03-27 | 1990-08-28 | Hoffmann-La Roche Inc. | Ethynylcyclohexene compounds |
US5227507A (en) * | 1987-03-27 | 1993-07-13 | Hoffmann-La Roche Inc. | Ethynylcyclohexene compounds and processes for manufacture thereof |
US5310554A (en) * | 1992-10-27 | 1994-05-10 | Natural Carotene Corporation | High purity beta-carotene |
US5328845A (en) * | 1992-03-27 | 1994-07-12 | Universal Foods Corporation | Fungal negative microorganism capable of producing high levels of beta-carotene |
US5364563A (en) * | 1989-07-25 | 1994-11-15 | Hoffmann-La Roche Inc. | Powdered aqueous carotenoid dispersions |
US5422247A (en) * | 1992-03-27 | 1995-06-06 | Universal Foods Corporation | Blakeslea trispora mated culture capable of increased beta-carotene production |
US5455362A (en) * | 1993-07-05 | 1995-10-03 | Basf Aktiengesellschaft | Preparation of astaxanthin novel intermediates therefor and the preparation thereof |
US5492701A (en) * | 1993-07-08 | 1996-02-20 | Rhone-Poulenc Nutrition Animale | Process for the preparation of spherules |
US5536504A (en) * | 1993-11-19 | 1996-07-16 | Marigen S.A. | Ultramicroemulsions from spontaneously dispersible concentrates containing xanthophyll esters and having antitumor activity |
US5543559A (en) * | 1994-07-07 | 1996-08-06 | Hoffman-La Roche Inc. | Process for the enantioselective hydrogenation of ketosiophorone derivatives |
US5607839A (en) * | 1993-07-22 | 1997-03-04 | Nippon Oil Company, Ltd. | Bacteria belonging to new genus process for production of carotenoids using same |
US5612485A (en) * | 1992-06-04 | 1997-03-18 | Betatene Ltd Of Cheltenham | High cis beta-carotene composition |
US5654488A (en) * | 1995-03-18 | 1997-08-05 | Basf Aktiengesellschaft | Preparation of astaxanthin |
US5849345A (en) * | 1994-12-21 | 1998-12-15 | Roche Vitamins Inc. | Carotenoid ketones and esters |
US5854015A (en) * | 1995-10-31 | 1998-12-29 | Applied Food Biotechnology, Inc. | Method of making pure 3R-3'R stereoisomer of zeaxanthin for human ingestion |
US5858700A (en) * | 1997-04-03 | 1999-01-12 | Kemin Foods, Lc | Process for the isolation and purification of lycopene crystals |
US5871766A (en) * | 1990-10-01 | 1999-02-16 | Brigham And Women's Hospital | Beta-carotene vitamin E therapy for inhibition of major vascular events |
US5876782A (en) * | 1997-05-14 | 1999-03-02 | Kemin Industries, Inc. | Method for the conversion of xanthophylls in plant material |
US5959138A (en) * | 1997-11-25 | 1999-09-28 | Industrial Organica S.A. De C.V. | Short chain diesters and process for making the same |
US6020003A (en) * | 1998-02-23 | 2000-02-01 | Basf Corporation | Method of making spray-dried powders with high edible-oil loadings based on non-hydrolyzed gelatin |
US6046181A (en) * | 1995-10-17 | 2000-04-04 | Showa Denko K.K. | Highly purified tocopheryl phosphate, process for producing the same, analytical method therefor and cosmetic |
US6060511A (en) * | 1995-10-05 | 2000-05-09 | Gainer; John L. | Trans-sodium crocetinate, methods of making and methods of use thereof |
US6245818B1 (en) * | 1997-09-04 | 2001-06-12 | Astacarotene Ab | Medicament for improvement of duration of muscle function or treatment of muscle disorders or diseases |
US6335015B1 (en) * | 1997-12-16 | 2002-01-01 | Astacarotene Ab | Method of the prophylactic treatment of mastitis |
US6540654B2 (en) * | 2001-02-23 | 2003-04-01 | Luis W. Levy | Carotenoid esters |
US20030143660A1 (en) * | 2001-11-20 | 2003-07-31 | Qiong Cheng | Method for production of asymmetric carotenoids |
US6610892B2 (en) * | 2001-03-12 | 2003-08-26 | Basf Aktiengesellschaft | Process for preparing 2,7-dimethyl-2,4,6-octatrienal monoacetals |
US6673971B2 (en) * | 1999-09-30 | 2004-01-06 | Basf Aktiengesellschaft | Preparation of 1,1,4,4-tetramethoxy-2-butene |
US20040049082A1 (en) * | 2001-01-26 | 2004-03-11 | Christoph Wegner | Thermal isomerizaton of lycopene |
US6747177B2 (en) * | 2001-09-13 | 2004-06-08 | Basf Aktiengesellschaft | Process for the preparation of meso-zeaxanthin |
US20040162329A1 (en) * | 2002-07-29 | 2004-08-19 | Lockwood Samuel Fournier | Structural carotenoid analogs for the inhibition and amelioration of disease |
US6827941B1 (en) * | 1998-01-21 | 2004-12-07 | Basf Aktiengesellschaft | Use of carotenoid aggregates as colorants |
US20050004235A1 (en) * | 2002-07-29 | 2005-01-06 | Lockwood Samuel Fournier | Carotenoid analogs or derivatives for the inhibition and amelioration of liver disease |
US20050009930A1 (en) * | 2002-07-29 | 2005-01-13 | Lockwood Samuel Fournier | Carotenoid analogs or derivatives for controlling connexin 43 expression |
US20050009788A1 (en) * | 2002-07-29 | 2005-01-13 | Lockwood Samuel Fournier | Carotenoid ester analogs or derivatives for controlling connexin 43 expression |
US20050009758A1 (en) * | 2002-07-29 | 2005-01-13 | Lockwood Samuel Fournier | Carotenoid ether analogs or derivatives for the inhibition and amelioration of disease |
US20050026874A1 (en) * | 2002-07-29 | 2005-02-03 | Lockwood Samuel Fournier | Carotenoid ether analogs or derivatives for the inhibition and amelioration of liver disease |
US20050049248A1 (en) * | 2002-07-29 | 2005-03-03 | Lockwood Samuel Fournier | Carotenoid ether analogs or derivatives for controlling C-reactive protein levels |
US20050059635A1 (en) * | 2002-07-29 | 2005-03-17 | Lockwood Samuel Fournier | Carotenoid ester analogs or derivatives for controlling C-reactive protein levels |
US20050059659A1 (en) * | 2002-07-29 | 2005-03-17 | Lockwood Samuel Fournier | Carotenoid analogs or derivatives for controlling C-reactive protein levels |
US20050065096A1 (en) * | 2002-07-29 | 2005-03-24 | Lockwood Samuel Fournier | Pharmaceutical compositions including carotenoid ether analogs or derivatives for the inhibition and amelioration of disease |
US20050075316A1 (en) * | 2002-07-29 | 2005-04-07 | Lockwood Samuel Fournier | Pharmaceutical compositions including carotenoid ester analogs or derivatives for the inhibition and amelioration of disease |
US20050090469A1 (en) * | 2002-07-29 | 2005-04-28 | Lockwood Samuel F. | Carotenoid ester analogs or derivatives for the inhibition and amelioration of liver disease |
US20050113372A1 (en) * | 2002-07-29 | 2005-05-26 | Lockwood Samuel F. | Carotenoid analogs or derivatives for the inhibition and amelioration of disease |
US20050143475A1 (en) * | 2002-07-29 | 2005-06-30 | Lockwood Samuel F. | Carotenoid analogs or derivatives for the inhibition and amelioration of ischemic reperfusion injury |
US20050148517A1 (en) * | 2002-07-29 | 2005-07-07 | Lockwood Samuel F. | Carotenoid ether analogs or derivatives for controlling connexin 43 expression |
US20050261254A1 (en) * | 2004-04-14 | 2005-11-24 | Lockwood Samuel F | Carotenoid analogs or derivatives for the inhibition and amelioration of inflammation |
US20060058269A1 (en) * | 2004-04-14 | 2006-03-16 | Lockwood Samuel F | Carotenoid analogs or derivatives for the inhibition and amelioration of inflammation |
US20060088904A1 (en) * | 2004-10-01 | 2006-04-27 | Lockwood Samuel F | Methods for the synthesis of astaxanthin |
Family Cites Families (9)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
EP0085158B1 (de) | 1982-01-28 | 1985-06-19 | F. HOFFMANN-LA ROCHE & CO. Aktiengesellschaft | Verfahren zur Herstellung von Cycloalkenonderivaten |
JPH07300421A (ja) | 1994-04-28 | 1995-11-14 | Itano Reitou Kk | 抗炎症剤 |
JPH0873312A (ja) | 1994-09-02 | 1996-03-19 | Noevir Co Ltd | 皮膚外用剤 |
JPH08337592A (ja) | 1995-06-13 | 1996-12-24 | Kaiyo Bio Technol Kenkyusho:Kk | 新規カロテノイド |
JPH0984591A (ja) | 1995-09-26 | 1997-03-31 | Kaiyo Bio Technol Kenkyusho:Kk | カロテノイド硫酸エステルおよびその製造方法 |
JPH09202730A (ja) | 1996-01-24 | 1997-08-05 | Nippon Mektron Ltd | 発ガン抑制作用剤 |
JPH10327865A (ja) | 1997-05-29 | 1998-12-15 | Kirin Brewery Co Ltd | カロテノイド配糖体およびその製造法 |
US7253297B2 (en) | 2002-02-06 | 2007-08-07 | Dsm Ip Assetts B.V. | Astaxanthin esters |
DE10358003A1 (de) | 2003-12-11 | 2005-07-14 | Basf Ag | Verfahren zur Herstellung von Astaxanthin- und Canthaxanthin-Vorprodukten |
-
2005
- 2005-10-03 US US11/242,609 patent/US20060167319A1/en not_active Abandoned
- 2005-10-03 US US11/242,615 patent/US20060155150A1/en not_active Abandoned
- 2005-10-03 US US11/242,627 patent/US20060111580A1/en not_active Abandoned
- 2005-10-03 US US11/242,591 patent/US20060088904A1/en not_active Abandoned
- 2005-10-03 WO PCT/US2005/035599 patent/WO2006039685A2/en active Application Filing
- 2005-10-03 US US11/242,645 patent/US20060183185A1/en not_active Abandoned
- 2005-10-03 US US11/242,641 patent/US20060178538A1/en not_active Abandoned
- 2005-10-03 US US11/242,639 patent/US20060088905A1/en not_active Abandoned
- 2005-10-03 US US11/242,643 patent/US7247752B2/en active Active
Patent Citations (67)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US3206316A (en) * | 1960-10-17 | 1965-09-14 | Hoffmann La Roche | Water dispersible carotenoid preparations and processes thereof |
US3354218A (en) * | 1963-05-10 | 1967-11-21 | Hoffmann La Roche | Process for preparing 4-(2, 6, 6-trimethyl-4-methoxy-1-cyclohexen-1-yl)-3-buten-2-one |
US3755422A (en) * | 1970-01-15 | 1973-08-28 | Rhone Poulenc Sa | Preparation of carotenoid compounds |
US3989757A (en) * | 1973-08-29 | 1976-11-02 | Hoffmann-La Roche Inc. | Isomerizing cis-carotenoids to all-trans-carotenoids |
US4245109A (en) * | 1978-06-02 | 1981-01-13 | Hoffmann-La Roche Inc. | Process for producing astaxanthin |
US4283559A (en) * | 1978-06-02 | 1981-08-11 | Hoffmann-La Roche Inc. | Process for the manufacture of cyclohexene derivatives |
US4435427A (en) * | 1980-12-19 | 1984-03-06 | Basf Aktiengesellschaft | Stable injectable β-carotene micellar solutions and their preparation |
US4585885A (en) * | 1982-08-20 | 1986-04-29 | Hoffmann-La Roche Inc. | Cyclohexenone derivatives and process for making same |
US4952716A (en) * | 1987-03-27 | 1990-08-28 | Hoffmann-La Roche Inc. | Ethynylcyclohexene compounds |
US5227507A (en) * | 1987-03-27 | 1993-07-13 | Hoffmann-La Roche Inc. | Ethynylcyclohexene compounds and processes for manufacture thereof |
US5364563A (en) * | 1989-07-25 | 1994-11-15 | Hoffmann-La Roche Inc. | Powdered aqueous carotenoid dispersions |
US5871766A (en) * | 1990-10-01 | 1999-02-16 | Brigham And Women's Hospital | Beta-carotene vitamin E therapy for inhibition of major vascular events |
US5422247A (en) * | 1992-03-27 | 1995-06-06 | Universal Foods Corporation | Blakeslea trispora mated culture capable of increased beta-carotene production |
US5328845A (en) * | 1992-03-27 | 1994-07-12 | Universal Foods Corporation | Fungal negative microorganism capable of producing high levels of beta-carotene |
US5612485A (en) * | 1992-06-04 | 1997-03-18 | Betatene Ltd Of Cheltenham | High cis beta-carotene composition |
US5310554A (en) * | 1992-10-27 | 1994-05-10 | Natural Carotene Corporation | High purity beta-carotene |
US5455362A (en) * | 1993-07-05 | 1995-10-03 | Basf Aktiengesellschaft | Preparation of astaxanthin novel intermediates therefor and the preparation thereof |
US5492701A (en) * | 1993-07-08 | 1996-02-20 | Rhone-Poulenc Nutrition Animale | Process for the preparation of spherules |
US5607839A (en) * | 1993-07-22 | 1997-03-04 | Nippon Oil Company, Ltd. | Bacteria belonging to new genus process for production of carotenoids using same |
US5536504A (en) * | 1993-11-19 | 1996-07-16 | Marigen S.A. | Ultramicroemulsions from spontaneously dispersible concentrates containing xanthophyll esters and having antitumor activity |
US5543559A (en) * | 1994-07-07 | 1996-08-06 | Hoffman-La Roche Inc. | Process for the enantioselective hydrogenation of ketosiophorone derivatives |
US5849345A (en) * | 1994-12-21 | 1998-12-15 | Roche Vitamins Inc. | Carotenoid ketones and esters |
US5654488A (en) * | 1995-03-18 | 1997-08-05 | Basf Aktiengesellschaft | Preparation of astaxanthin |
US6060511A (en) * | 1995-10-05 | 2000-05-09 | Gainer; John L. | Trans-sodium crocetinate, methods of making and methods of use thereof |
US6046181A (en) * | 1995-10-17 | 2000-04-04 | Showa Denko K.K. | Highly purified tocopheryl phosphate, process for producing the same, analytical method therefor and cosmetic |
US5854015A (en) * | 1995-10-31 | 1998-12-29 | Applied Food Biotechnology, Inc. | Method of making pure 3R-3'R stereoisomer of zeaxanthin for human ingestion |
US5858700A (en) * | 1997-04-03 | 1999-01-12 | Kemin Foods, Lc | Process for the isolation and purification of lycopene crystals |
US5876782A (en) * | 1997-05-14 | 1999-03-02 | Kemin Industries, Inc. | Method for the conversion of xanthophylls in plant material |
US6245818B1 (en) * | 1997-09-04 | 2001-06-12 | Astacarotene Ab | Medicament for improvement of duration of muscle function or treatment of muscle disorders or diseases |
US5959138A (en) * | 1997-11-25 | 1999-09-28 | Industrial Organica S.A. De C.V. | Short chain diesters and process for making the same |
US6335015B1 (en) * | 1997-12-16 | 2002-01-01 | Astacarotene Ab | Method of the prophylactic treatment of mastitis |
US6827941B1 (en) * | 1998-01-21 | 2004-12-07 | Basf Aktiengesellschaft | Use of carotenoid aggregates as colorants |
US6020003A (en) * | 1998-02-23 | 2000-02-01 | Basf Corporation | Method of making spray-dried powders with high edible-oil loadings based on non-hydrolyzed gelatin |
US6673971B2 (en) * | 1999-09-30 | 2004-01-06 | Basf Aktiengesellschaft | Preparation of 1,1,4,4-tetramethoxy-2-butene |
US20040049082A1 (en) * | 2001-01-26 | 2004-03-11 | Christoph Wegner | Thermal isomerizaton of lycopene |
US6540654B2 (en) * | 2001-02-23 | 2003-04-01 | Luis W. Levy | Carotenoid esters |
US6610892B2 (en) * | 2001-03-12 | 2003-08-26 | Basf Aktiengesellschaft | Process for preparing 2,7-dimethyl-2,4,6-octatrienal monoacetals |
US6747177B2 (en) * | 2001-09-13 | 2004-06-08 | Basf Aktiengesellschaft | Process for the preparation of meso-zeaxanthin |
US20030143660A1 (en) * | 2001-11-20 | 2003-07-31 | Qiong Cheng | Method for production of asymmetric carotenoids |
US20050065097A1 (en) * | 2002-07-29 | 2005-03-24 | Lockwood Samuel Fournier | Carotenoid ether analogs or derivatives for the inhibition and amelioration of ischemic reperfusion injury |
US20050075337A1 (en) * | 2002-07-29 | 2005-04-07 | Lockwood Samuel Fournier | Pharmaceutical compositions including carotenoid analogs or derivatives for the inhabition and amelioration of disease |
US20050009930A1 (en) * | 2002-07-29 | 2005-01-13 | Lockwood Samuel Fournier | Carotenoid analogs or derivatives for controlling connexin 43 expression |
US20050009788A1 (en) * | 2002-07-29 | 2005-01-13 | Lockwood Samuel Fournier | Carotenoid ester analogs or derivatives for controlling connexin 43 expression |
US20050009758A1 (en) * | 2002-07-29 | 2005-01-13 | Lockwood Samuel Fournier | Carotenoid ether analogs or derivatives for the inhibition and amelioration of disease |
US20050026874A1 (en) * | 2002-07-29 | 2005-02-03 | Lockwood Samuel Fournier | Carotenoid ether analogs or derivatives for the inhibition and amelioration of liver disease |
US20050037995A1 (en) * | 2002-07-29 | 2005-02-17 | Lockwood Samuel Fournier | Carotenoid ester analogs or derivatives for the inhibition and amelioration of ischemic reperfusion injury |
US20050049248A1 (en) * | 2002-07-29 | 2005-03-03 | Lockwood Samuel Fournier | Carotenoid ether analogs or derivatives for controlling C-reactive protein levels |
US20050059635A1 (en) * | 2002-07-29 | 2005-03-17 | Lockwood Samuel Fournier | Carotenoid ester analogs or derivatives for controlling C-reactive protein levels |
US20050059659A1 (en) * | 2002-07-29 | 2005-03-17 | Lockwood Samuel Fournier | Carotenoid analogs or derivatives for controlling C-reactive protein levels |
US20050065096A1 (en) * | 2002-07-29 | 2005-03-24 | Lockwood Samuel Fournier | Pharmaceutical compositions including carotenoid ether analogs or derivatives for the inhibition and amelioration of disease |
US20040162329A1 (en) * | 2002-07-29 | 2004-08-19 | Lockwood Samuel Fournier | Structural carotenoid analogs for the inhibition and amelioration of disease |
US20050075316A1 (en) * | 2002-07-29 | 2005-04-07 | Lockwood Samuel Fournier | Pharmaceutical compositions including carotenoid ester analogs or derivatives for the inhibition and amelioration of disease |
US20050004235A1 (en) * | 2002-07-29 | 2005-01-06 | Lockwood Samuel Fournier | Carotenoid analogs or derivatives for the inhibition and amelioration of liver disease |
US20050090469A1 (en) * | 2002-07-29 | 2005-04-28 | Lockwood Samuel F. | Carotenoid ester analogs or derivatives for the inhibition and amelioration of liver disease |
US20050113372A1 (en) * | 2002-07-29 | 2005-05-26 | Lockwood Samuel F. | Carotenoid analogs or derivatives for the inhibition and amelioration of disease |
US20050143475A1 (en) * | 2002-07-29 | 2005-06-30 | Lockwood Samuel F. | Carotenoid analogs or derivatives for the inhibition and amelioration of ischemic reperfusion injury |
US20050148517A1 (en) * | 2002-07-29 | 2005-07-07 | Lockwood Samuel F. | Carotenoid ether analogs or derivatives for controlling connexin 43 expression |
US20060229446A1 (en) * | 2002-07-29 | 2006-10-12 | Hawaii Biotech, Inc. | Structural carotenoid analogs for the inhibition and amelioration of disease |
US20060058269A1 (en) * | 2004-04-14 | 2006-03-16 | Lockwood Samuel F | Carotenoid analogs or derivatives for the inhibition and amelioration of inflammation |
US20050261254A1 (en) * | 2004-04-14 | 2005-11-24 | Lockwood Samuel F | Carotenoid analogs or derivatives for the inhibition and amelioration of inflammation |
US20060088904A1 (en) * | 2004-10-01 | 2006-04-27 | Lockwood Samuel F | Methods for the synthesis of astaxanthin |
US20060088905A1 (en) * | 2004-10-01 | 2006-04-27 | Lockwood Samuel F | Methods for the synthesis of zeazanthin |
US20060111580A1 (en) * | 2004-10-01 | 2006-05-25 | Lockwood Samuel F | Methods for the synthesis of chiral dihydroxy ketone intermediates useful for the chiral synthesis of carotenoids |
US20060155150A1 (en) * | 2004-10-01 | 2006-07-13 | Lockwood Samuel F | Methods for the synthesis of lutein |
US20060178538A1 (en) * | 2004-10-01 | 2006-08-10 | Lockwood Samuel F | Methods for the synthesis of chiral dihydroxy intermediates useful for the chiral synthesis of carotenoids |
US20060183947A1 (en) * | 2004-10-01 | 2006-08-17 | Lockwood Samuel F | Methods for the synthesis of astaxanthin |
US20060183185A1 (en) * | 2004-10-01 | 2006-08-17 | Lockwood Samuel F | Method for the synthesis of astaxanthin |
Cited By (19)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US20050009930A1 (en) * | 2002-07-29 | 2005-01-13 | Lockwood Samuel Fournier | Carotenoid analogs or derivatives for controlling connexin 43 expression |
US20050037995A1 (en) * | 2002-07-29 | 2005-02-17 | Lockwood Samuel Fournier | Carotenoid ester analogs or derivatives for the inhibition and amelioration of ischemic reperfusion injury |
US20050065096A1 (en) * | 2002-07-29 | 2005-03-24 | Lockwood Samuel Fournier | Pharmaceutical compositions including carotenoid ether analogs or derivatives for the inhibition and amelioration of disease |
US20050090469A1 (en) * | 2002-07-29 | 2005-04-28 | Lockwood Samuel F. | Carotenoid ester analogs or derivatives for the inhibition and amelioration of liver disease |
US20050113372A1 (en) * | 2002-07-29 | 2005-05-26 | Lockwood Samuel F. | Carotenoid analogs or derivatives for the inhibition and amelioration of disease |
US7763649B2 (en) | 2002-07-29 | 2010-07-27 | Cardax Pharmaceuticals, Inc. | Carotenoid analogs or derivatives for controlling connexin 43 expression |
US7723327B2 (en) | 2002-07-29 | 2010-05-25 | Cardax Pharmaceuticals, Inc. | Carotenoid ester analogs or derivatives for the inhibition and amelioration of liver disease |
US20060155150A1 (en) * | 2004-10-01 | 2006-07-13 | Lockwood Samuel F | Methods for the synthesis of lutein |
US20060111580A1 (en) * | 2004-10-01 | 2006-05-25 | Lockwood Samuel F | Methods for the synthesis of chiral dihydroxy ketone intermediates useful for the chiral synthesis of carotenoids |
US20060178538A1 (en) * | 2004-10-01 | 2006-08-10 | Lockwood Samuel F | Methods for the synthesis of chiral dihydroxy intermediates useful for the chiral synthesis of carotenoids |
US20060183185A1 (en) * | 2004-10-01 | 2006-08-17 | Lockwood Samuel F | Method for the synthesis of astaxanthin |
US20060183947A1 (en) * | 2004-10-01 | 2006-08-17 | Lockwood Samuel F | Methods for the synthesis of astaxanthin |
US7247752B2 (en) | 2004-10-01 | 2007-07-24 | Cardax Pharmaceuticals, Inc. | Methods for the synthesis of astaxanthin |
US20060088904A1 (en) * | 2004-10-01 | 2006-04-27 | Lockwood Samuel F | Methods for the synthesis of astaxanthin |
US20060088905A1 (en) * | 2004-10-01 | 2006-04-27 | Lockwood Samuel F | Methods for the synthesis of zeazanthin |
US20090099061A1 (en) * | 2006-01-27 | 2009-04-16 | Foss Bente J | Synthesis of carotenoid analogs or derivatives with improved antioxidant characteristics |
US20090124574A1 (en) * | 2007-03-23 | 2009-05-14 | Lockwood Samuel F | Carotenoid analogs and derivatives for the prevention of platelet aggregation |
US8063101B2 (en) | 2007-03-23 | 2011-11-22 | Cardax Pharmaceuticals, Inc. | Carotenoid analogs and derivatives for the prevention of platelet aggregation |
CN101906445A (zh) * | 2010-06-18 | 2010-12-08 | 西南大学 | 2h-1-苯并吡喃-2-酮衍生物的合成方法 |
Also Published As
Publication number | Publication date |
---|---|
US20060111580A1 (en) | 2006-05-25 |
US20060183185A1 (en) | 2006-08-17 |
US20060088905A1 (en) | 2006-04-27 |
US20060178538A1 (en) | 2006-08-10 |
US20060088904A1 (en) | 2006-04-27 |
US20060155150A1 (en) | 2006-07-13 |
WO2006039685A2 (en) | 2006-04-13 |
US7247752B2 (en) | 2007-07-24 |
US20060183947A1 (en) | 2006-08-17 |
WO2006039685A3 (en) | 2007-01-04 |
Similar Documents
Publication | Publication Date | Title |
---|---|---|
US7247752B2 (en) | Methods for the synthesis of astaxanthin | |
Shen et al. | A novel and practical synthetic route for the total synthesis of lycopene | |
US20080221377A1 (en) | Methods for synthesis of carotenoids, including analogs, derivatives, and synthetic and biological intermediates | |
US6201155B1 (en) | Process for making 4,4′-diketo-carotenoids | |
US7435861B2 (en) | Methods for synthesis of carotenoids, including analogs, derivatives, and synthetic and biological intermediates | |
US3558712A (en) | Method for the synthesis of zeaxanthins,xanthophylis,and 3-oxo-beta carotene | |
EP0461653B1 (en) | Process for producing beta-carotene, and intermediate compounds useful for the process | |
US11897842B2 (en) | Method for producing 7-methyl-3-methylene-7-octenal acetal compound | |
JPH1059894A (ja) | ポリエンエステル及びポリエン酸の製造方法 | |
US3125571A (en) | Hjc chs | |
JP3961136B2 (ja) | ポリエンアルデヒドの製造 | |
WO2008092655A1 (en) | Process for preparing dienones | |
US5237102A (en) | Sulfone aldehydes useful for producing β-carotene | |
US5952519A (en) | C-15 phosphonate reagent compositions for the manufacture of compounds such as canthaxanthin and methods of synthesizing the same | |
JP3961073B2 (ja) | ポリエン(ジ)アルデヒドの製造方法 | |
Oritani et al. | Syntheses of pentadienoic acids structurally related to abscisic acid | |
Rivas et al. | Stereoselective Synthesis of Bisfuranoxide (Aurochrome, Auroxanthin) and Monofuranoxide (Equinenone 5′, 8′-Epoxide) Carotenoids by Double Horner–Wadsworth–Emmons Reaction | |
Shikichi et al. | Synthesis of All the Stereoisomers of 6-Methyl-2-octadecanone, 14-Methyl-2-octadecanone, and 6, 14-Dimethyl-2-octadecanone, Sex Pheromone Components of the Lyclene dharma dharma Moth, from the Enantiomers of Citronellal | |
US20240116843A1 (en) | Process for the preparation of vitamin k2 and novel intermediates | |
Matsui et al. | The synthesis of methyl vitamin A | |
Pfander et al. | Acyclic Carotenoids | |
Kulkarni et al. | A SHORT SYNTHESIS OF (11Z, 15Z)-EICOSADIENOIC ACID, A COMPOUND OF MARINE SPONGE ORIGIN | |
Zhu | Application of a novel carbonyl ene reaction: Total syntheses of phyllanthocin and chlorovulone II | |
JPS5829769B2 (ja) | デカプレノ−ルノゴウセイホウ | |
FR2567511A1 (fr) | Procede de preparation de composes halogenes en a d'un groupement electroattracteur |
Legal Events
Date | Code | Title | Description |
---|---|---|---|
AS | Assignment |
Owner name: HAWAII BIOTECH, INC., HAWAII Free format text: ASSIGNMENT OF ASSIGNORS INTEREST;ASSIGNORS:LOCKWOOD, SAMUEL F.;TANG, PENG CHO;NADOLSKI, GEOFF T.;AND OTHERS;REEL/FRAME:017674/0749;SIGNING DATES FROM 20060124 TO 20060309 |
|
AS | Assignment |
Owner name: CARDAX PHARMACEUTICALS, INC., HAWAII Free format text: ASSIGNMENT OF ASSIGNORS INTEREST;ASSIGNOR:HAWAII BIOTECH, INC.;REEL/FRAME:018298/0462 Effective date: 20060808 |
|
STCB | Information on status: application discontinuation |
Free format text: ABANDONED -- FAILURE TO PAY ISSUE FEE |