CA1221105A - Acides gras halogenes en position omega - Google Patents
Acides gras halogenes en position omegaInfo
- Publication number
- CA1221105A CA1221105A CA000436822A CA436822A CA1221105A CA 1221105 A CA1221105 A CA 1221105A CA 000436822 A CA000436822 A CA 000436822A CA 436822 A CA436822 A CA 436822A CA 1221105 A CA1221105 A CA 1221105A
- Authority
- CA
- Canada
- Prior art keywords
- methyl
- enolide
- group
- oxo
- cis
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Expired
Links
- 239000000194 fatty acid Substances 0.000 title claims abstract description 86
- 235000014113 dietary fatty acids Nutrition 0.000 title claims abstract description 84
- 229930195729 fatty acid Natural products 0.000 title claims abstract description 84
- 150000004665 fatty acids Chemical class 0.000 title claims abstract description 55
- -1 hydroxy fatty acid Chemical class 0.000 claims abstract description 155
- 238000000034 method Methods 0.000 claims abstract description 66
- 230000002285 radioactive effect Effects 0.000 claims abstract description 43
- 150000002596 lactones Chemical class 0.000 claims abstract description 37
- 241000402754 Erythranthe moschata Species 0.000 claims abstract description 31
- 238000003384 imaging method Methods 0.000 claims abstract description 10
- 238000006467 substitution reaction Methods 0.000 claims abstract description 6
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 37
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 claims description 35
- 125000001570 methylene group Chemical group [H]C([H])([*:1])[*:2] 0.000 claims description 35
- LOKPJYNMYCVCRM-UHFFFAOYSA-N 16-Hexadecanolide Chemical compound O=C1CCCCCCCCCCCCCCCO1 LOKPJYNMYCVCRM-UHFFFAOYSA-N 0.000 claims description 25
- FKUPPRZPSYCDRS-UHFFFAOYSA-N Cyclopentadecanolide Chemical compound O=C1CCCCCCCCCCCCCCO1 FKUPPRZPSYCDRS-UHFFFAOYSA-N 0.000 claims description 25
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims description 24
- 229910052760 oxygen Inorganic materials 0.000 claims description 24
- 239000001301 oxygen Substances 0.000 claims description 24
- 229910052739 hydrogen Inorganic materials 0.000 claims description 23
- 239000001257 hydrogen Substances 0.000 claims description 23
- LVECZGHBXXYWBO-UHFFFAOYSA-N pentadecanolide Natural products CC1CCCCCCCCCCCCC(=O)O1 LVECZGHBXXYWBO-UHFFFAOYSA-N 0.000 claims description 19
- GILZFLFJYUGJLX-UHFFFAOYSA-N 15-Hexadecanolide Chemical compound CC1CCCCCCCCCCCCCC(=O)O1 GILZFLFJYUGJLX-UHFFFAOYSA-N 0.000 claims description 15
- 229910052740 iodine Inorganic materials 0.000 claims description 15
- NVIPUOMWGQAOIT-UHFFFAOYSA-N 1-oxacycloheptadec-8-en-2-one Chemical compound O=C1CCCCCC=CCCCCCCCCO1 NVIPUOMWGQAOIT-UHFFFAOYSA-N 0.000 claims description 12
- 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 claims description 12
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 12
- ZCYVEMRRCGMTRW-AHCXROLUSA-N Iodine-123 Chemical compound [123I] ZCYVEMRRCGMTRW-AHCXROLUSA-N 0.000 claims description 11
- 229910052794 bromium Inorganic materials 0.000 claims description 11
- 150000002431 hydrogen Chemical class 0.000 claims description 11
- PNDPGZBMCMUPRI-HVTJNCQCSA-N 10043-66-0 Chemical compound [131I][131I] PNDPGZBMCMUPRI-HVTJNCQCSA-N 0.000 claims description 10
- QFRZEGADDLNLLM-UHFFFAOYSA-N oxacyclohexadecane-2,13-dione Chemical compound O=C1CCCCCCCCCCC(=O)OCCC1 QFRZEGADDLNLLM-UHFFFAOYSA-N 0.000 claims description 10
- MRMOPGVGWFNHIN-UHFFFAOYSA-N 1,6-dioxacycloheptadecan-7-one Chemical compound O=C1CCCCCCCCCCOCCCCO1 MRMOPGVGWFNHIN-UHFFFAOYSA-N 0.000 claims description 9
- UGAGPNKCDRTDHP-UHFFFAOYSA-N 16-hydroxyhexadecanoic acid Chemical compound OCCCCCCCCCCCCCCCC(O)=O UGAGPNKCDRTDHP-UHFFFAOYSA-N 0.000 claims description 8
- BZUNJUAMQZRJIP-UHFFFAOYSA-N 15-hydroxypentadecanoic acid Chemical compound OCCCCCCCCCCCCCCC(O)=O BZUNJUAMQZRJIP-UHFFFAOYSA-N 0.000 claims description 6
- UJCAIOVANRWRFI-GQCTYLIASA-N (12E)-1-oxacyclooctadec-12-en-2-one Chemical compound O=C1CCCCCCCCC\C=C\CCCCCO1 UJCAIOVANRWRFI-GQCTYLIASA-N 0.000 claims description 5
- CPEZOJDEAFZIOV-CSKARUKUSA-N (12E)-15-methyl-1-oxacyclohexadec-12-en-2-one Chemical compound CC1COC(=O)CCCCCCCCC\C=C\C1 CPEZOJDEAFZIOV-CSKARUKUSA-N 0.000 claims description 5
- BVOJLLPACRYBJY-SOFGYWHQSA-N (12E)-17-methyl-1-oxacyclooctadec-12-en-2-one Chemical compound CC1CCC\C=C\CCCCCCCCCC(=O)OC1 BVOJLLPACRYBJY-SOFGYWHQSA-N 0.000 claims description 5
- BIVPZAQPTPSLGK-FNORWQNLSA-N (12E)-18-methyl-1-oxacyclooctadec-12-en-2-one Chemical compound CC1CCCC\C=C\CCCCCCCCCC(=O)O1 BIVPZAQPTPSLGK-FNORWQNLSA-N 0.000 claims description 5
- ZYXGECMFJMLZNA-SOFGYWHQSA-N (12e)-1-oxacyclohexadec-12-en-2-one Chemical compound O=C1CCCCCCCCC\C=C\CCCO1 ZYXGECMFJMLZNA-SOFGYWHQSA-N 0.000 claims description 5
- DZWGBXMOQSWEOF-VQHVLOKHSA-N (13E)-18-methyl-1-oxacyclooctadec-13-en-2-one Chemical compound CC1CCC\C=C\CCCCCCCCCCC(=O)O1 DZWGBXMOQSWEOF-VQHVLOKHSA-N 0.000 claims description 5
- AGZBJJSLDGWKSU-CSKARUKUSA-N (13e)-1-oxacyclohexadec-13-en-2-one Chemical compound O=C1CCCCCCCCCC\C=C\CCO1 AGZBJJSLDGWKSU-CSKARUKUSA-N 0.000 claims description 5
- ZQNAETILAJTQCW-PKNBQFBNSA-N (13e)-16-methyl-1-oxacyclohexadec-13-en-2-one Chemical compound CC1C\C=C\CCCCCCCCCCC(=O)O1 ZQNAETILAJTQCW-PKNBQFBNSA-N 0.000 claims description 5
- HKILVMFAECPLNT-UHFFFAOYSA-N 1,4,7-trioxacycloheptadecan-8-one Chemical compound O=C1CCCCCCCCCOCCOCCO1 HKILVMFAECPLNT-UHFFFAOYSA-N 0.000 claims description 5
- YEBHGHOBBXQRCX-UHFFFAOYSA-N 1,4-dioxacyclopentadecan-5-one Chemical compound O=C1CCCCCCCCCCOCCO1 YEBHGHOBBXQRCX-UHFFFAOYSA-N 0.000 claims description 5
- UALVTPDMFRBKDK-UHFFFAOYSA-N 1,5-dioxacyclohexadecan-6-one Chemical compound O=C1CCCCCCCCCCOCCCO1 UALVTPDMFRBKDK-UHFFFAOYSA-N 0.000 claims description 5
- GPWHJXUZCKGHOV-UHFFFAOYSA-N 14-methyl-oxacyclopentadecane-2,12-dione Chemical compound CC1COC(=O)CCCCCCCCCC(=O)C1 GPWHJXUZCKGHOV-UHFFFAOYSA-N 0.000 claims description 5
- PWOWBHUWHIXCKV-UHFFFAOYSA-N 15-ethyl-oxacyclohexadecane-2,13-dione Chemical compound CCC1COC(=O)CCCCCCCCCCC(=O)C1 PWOWBHUWHIXCKV-UHFFFAOYSA-N 0.000 claims description 5
- FDUMHFPPCZNHET-UHFFFAOYSA-N 15-methyl-oxacycloheptadecane-2,13-dione Chemical compound CC1CCOC(=O)CCCCCCCCCCC(=O)C1 FDUMHFPPCZNHET-UHFFFAOYSA-N 0.000 claims description 5
- OMEHFLCQTFHGJQ-UHFFFAOYSA-N 15-methyl-oxacyclohexadecane-2,13-dione Chemical compound CC1COC(=O)CCCCCCCCCCC(=O)C1 OMEHFLCQTFHGJQ-UHFFFAOYSA-N 0.000 claims description 5
- RIFYFRLMMYUQNP-UHFFFAOYSA-N 15-methyl-oxacyclopentadecane-2,13-dione Chemical compound CC1CC(=O)CCCCCCCCCCC(=O)O1 RIFYFRLMMYUQNP-UHFFFAOYSA-N 0.000 claims description 5
- BXUAFPXADZNGNU-UHFFFAOYSA-N 15-methyloxacyclohexadecan-2-one Chemical compound CC1CCCCCCCCCCCCC(=O)OC1 BXUAFPXADZNGNU-UHFFFAOYSA-N 0.000 claims description 5
- RBVISHJQKSLULJ-UHFFFAOYSA-N 16-ethyl-oxacyclohexadecane-2,13-dione Chemical compound CCC1CCC(=O)CCCCCCCCCCC(=O)O1 RBVISHJQKSLULJ-UHFFFAOYSA-N 0.000 claims description 5
- VWHITFXVCLITMY-UHFFFAOYSA-N 16-methyl-oxacycloheptadecan-2-one Chemical compound CC1CCCCCCCCCCCCCC(=O)OC1 VWHITFXVCLITMY-UHFFFAOYSA-N 0.000 claims description 5
- PNXDPYXFAFMSNJ-UHFFFAOYSA-N 17-methyl-oxacycloheptadecan-2-one Chemical compound CC1CCCCCCCCCCCCCCC(=O)O1 PNXDPYXFAFMSNJ-UHFFFAOYSA-N 0.000 claims description 5
- STNSTYGHEKTMLV-UHFFFAOYSA-N 17-methyl-oxacycloheptadecane-2,14-dione Chemical compound CC1CCC(=O)CCCCCCCCCCCC(=O)O1 STNSTYGHEKTMLV-UHFFFAOYSA-N 0.000 claims description 5
- RADMMPRHRKIAEW-UHFFFAOYSA-N 17-methyl-oxacyclooctadecan-2-one Chemical compound CC1CCCCCCCCCCCCCCC(=O)OC1 RADMMPRHRKIAEW-UHFFFAOYSA-N 0.000 claims description 5
- DILFSXXFMBRWQM-UHFFFAOYSA-N 18-methyl-oxacyclooctadecan-2-one Chemical compound CC1CCCCCCCCCCCCCCCC(=O)O1 DILFSXXFMBRWQM-UHFFFAOYSA-N 0.000 claims description 5
- BFRVMARKLHXDFW-UHFFFAOYSA-N oxacycloheptadecane-2,13-dione Chemical compound O=C1CCCCCCCCCCC(=O)OCCCC1 BFRVMARKLHXDFW-UHFFFAOYSA-N 0.000 claims description 5
- CCPUCBDXXGAGDT-UHFFFAOYSA-N oxacycloheptadecane-2,14-dione Chemical compound O=C1CCCCCCCCCCCC(=O)OCCC1 CCPUCBDXXGAGDT-UHFFFAOYSA-N 0.000 claims description 5
- WJNGCQHLZNBMMQ-UHFFFAOYSA-N oxacycloheptadecane-2,15-dione Chemical compound O=C1CCCCCCCCCCCCC(=O)OCC1 WJNGCQHLZNBMMQ-UHFFFAOYSA-N 0.000 claims description 5
- FXQOOHFUXNQCKQ-UHFFFAOYSA-N oxacyclooctadecan-2-one Chemical compound O=C1CCCCCCCCCCCCCCCCO1 FXQOOHFUXNQCKQ-UHFFFAOYSA-N 0.000 claims description 5
- ROCJJPDKVXHJLK-UHFFFAOYSA-N oxacyclooctadecane-2,16-dione Chemical compound O=C1CCCCCCCCCCCCCC(=O)OCC1 ROCJJPDKVXHJLK-UHFFFAOYSA-N 0.000 claims description 5
- QLSYXWGLWSUYIQ-UHFFFAOYSA-N oxacyclopentadecane-2,13-dione Chemical compound O=C1CCCCCCCCCCC(=O)OCC1 QLSYXWGLWSUYIQ-UHFFFAOYSA-N 0.000 claims description 5
- XWCWYOGCIDZQFF-VQHVLOKHSA-N (13e)-1-oxacycloheptadec-13-en-2-one Chemical compound O=C1CCCCCCCCCC\C=C\CCCO1 XWCWYOGCIDZQFF-VQHVLOKHSA-N 0.000 claims description 4
- MKIFOPBVDBXRTO-DUXPYHPUSA-N (e)-16-hydroxyhexadec-7-enoic acid Chemical compound OCCCCCCCC\C=C\CCCCCC(O)=O MKIFOPBVDBXRTO-DUXPYHPUSA-N 0.000 claims description 4
- MKIFOPBVDBXRTO-UHFFFAOYSA-N 16-Hydroxy-7-hexadecenoic acid Natural products OCCCCCCCCC=CCCCCCC(O)=O MKIFOPBVDBXRTO-UHFFFAOYSA-N 0.000 claims description 4
- ILYKAONTGVXXQO-UHFFFAOYSA-N 16-methyl-oxacycloheptadecane-2,14-dione Chemical compound CC1COC(=O)CCCCCCCCCCCC(=O)C1 ILYKAONTGVXXQO-UHFFFAOYSA-N 0.000 claims description 4
- 229910052736 halogen Inorganic materials 0.000 claims description 4
- 150000002367 halogens Chemical class 0.000 claims description 4
- 229920006395 saturated elastomer Polymers 0.000 claims description 4
- KAIQFVRSSKPNJF-UHFFFAOYSA-N 11-(4-hydroxybutoxy)undecanoic acid Chemical compound OCCCCOCCCCCCCCCCC(O)=O KAIQFVRSSKPNJF-UHFFFAOYSA-N 0.000 claims description 3
- SHXXBFGBKFKECN-UHFFFAOYSA-N 15-hydroxy-12-oxopentadecanoic acid Chemical compound OCCCC(=O)CCCCCCCCCCC(O)=O SHXXBFGBKFKECN-UHFFFAOYSA-N 0.000 claims description 3
- WKBOTKDWSSQWDR-OIOBTWANSA-N Bromine-77 Chemical compound [77Br] WKBOTKDWSSQWDR-OIOBTWANSA-N 0.000 claims description 3
- CPELXLSAUQHCOX-FTXFMUIASA-N bromine-75 Chemical compound [75BrH] CPELXLSAUQHCOX-FTXFMUIASA-N 0.000 claims description 3
- XMBWDFGMSWQBCA-FTXFMUIASA-N iodane Chemical group [122IH] XMBWDFGMSWQBCA-FTXFMUIASA-N 0.000 claims description 3
- 238000004519 manufacturing process Methods 0.000 claims description 3
- 210000000056 organ Anatomy 0.000 claims description 3
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 2
- 239000003795 chemical substances by application Substances 0.000 claims description 2
- JOXIMZWYDAKGHI-UHFFFAOYSA-N toluene-4-sulfonic acid Chemical compound CC1=CC=C(S(O)(=O)=O)C=C1 JOXIMZWYDAKGHI-UHFFFAOYSA-N 0.000 claims description 2
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims 10
- 125000005490 tosylate group Chemical group 0.000 claims 10
- MYVRNQKGUGPNBC-VQHVLOKHSA-N (12E)-16-methyl-1-oxacyclohexadec-12-en-2-one Chemical compound CC1CC\C=C\CCCCCCCCCC(=O)O1 MYVRNQKGUGPNBC-VQHVLOKHSA-N 0.000 claims 4
- RPUFPHXXZYMEMX-SOFGYWHQSA-N (13E)-1-oxacyclooctadec-13-en-2-one Chemical compound O=C1CCCCCCCCCC\C=C\CCCCO1 RPUFPHXXZYMEMX-SOFGYWHQSA-N 0.000 claims 4
- PUCJVOSCFSBWRK-ZRDIBKRKSA-N (13E)-15-methyl-1-oxacyclohexadec-13-en-2-one Chemical compound CC/1COC(=O)CCCCCCCCCC\C=C\1 PUCJVOSCFSBWRK-ZRDIBKRKSA-N 0.000 claims 4
- CBJPDJUFZNFDHR-UHFFFAOYSA-N 14-methyl-oxacyclotetradecane-2,12-dione Chemical compound CC1CC(=O)CCCCCCCCCC(=O)O1 CBJPDJUFZNFDHR-UHFFFAOYSA-N 0.000 claims 4
- VYHPYLJWAYVWNU-UHFFFAOYSA-N 15-methyl-oxacyclopentadecane-2,12-dione Chemical compound CC1CCC(=O)CCCCCCCCCC(=O)O1 VYHPYLJWAYVWNU-UHFFFAOYSA-N 0.000 claims 4
- LTLJFUQAACYNAP-UHFFFAOYSA-N 16-methyl-oxacyclohexadecane-2,13-dione Chemical compound CC1CCC(=O)CCCCCCCCCCC(=O)O1 LTLJFUQAACYNAP-UHFFFAOYSA-N 0.000 claims 4
- AXXOBVHFRKPGJC-UHFFFAOYSA-N oxacyclohexadecane-2,12-dione Chemical compound O=C1CCCCCCCCCC(=O)OCCCC1 AXXOBVHFRKPGJC-UHFFFAOYSA-N 0.000 claims 4
- DZJOCNIKAFKCNT-UHFFFAOYSA-N oxacyclononadecane-2,16-dione Chemical compound O=C1CCCCCCCCCCCCCC(=O)OCCC1 DZJOCNIKAFKCNT-UHFFFAOYSA-N 0.000 claims 4
- OTQIFJSOBYHXDG-UHFFFAOYSA-N oxacyclopentadecane-2,12-dione Chemical compound O=C1CCCCCCCCCC(=O)OCCC1 OTQIFJSOBYHXDG-UHFFFAOYSA-N 0.000 claims 4
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- NGSKFPWYHQABEX-CSKARUKUSA-N (13E)-17-methyl-1-oxacyclooctadec-13-en-2-one Chemical compound CC1CC\C=C\CCCCCCCCCCC(=O)OC1 NGSKFPWYHQABEX-CSKARUKUSA-N 0.000 claims 3
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- AFVFQIVMOAPDHO-UHFFFAOYSA-N Methanesulfonic acid Chemical compound CS(O)(=O)=O AFVFQIVMOAPDHO-UHFFFAOYSA-N 0.000 claims 2
- 239000012216 imaging agent Substances 0.000 claims 2
- ITMCEJHCFYSIIV-UHFFFAOYSA-M triflate Chemical compound [O-]S(=O)(=O)C(F)(F)F ITMCEJHCFYSIIV-UHFFFAOYSA-M 0.000 claims 2
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims 1
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- 230000036765 blood level Effects 0.000 description 1
- 239000005388 borosilicate glass Substances 0.000 description 1
- OSGAYBCDTDRGGQ-UHFFFAOYSA-L calcium sulfate Chemical compound [Ca+2].[O-]S([O-])(=O)=O OSGAYBCDTDRGGQ-UHFFFAOYSA-L 0.000 description 1
- 125000004432 carbon atom Chemical group C* 0.000 description 1
- 210000004027 cell Anatomy 0.000 description 1
- 210000000170 cell membrane Anatomy 0.000 description 1
- 239000001913 cellulose Substances 0.000 description 1
- 229920002678 cellulose Polymers 0.000 description 1
- 238000006243 chemical reaction Methods 0.000 description 1
- 239000007795 chemical reaction product Substances 0.000 description 1
- 125000001309 chloro group Chemical group Cl* 0.000 description 1
- SECPZKHBENQXJG-UHFFFAOYSA-N cis-palmitoleic acid Natural products CCCCCCC=CCCCCCCCC(O)=O SECPZKHBENQXJG-UHFFFAOYSA-N 0.000 description 1
- 239000013078 crystal Substances 0.000 description 1
- ZKVZSBSZTMPBQR-UHFFFAOYSA-N cycloheptadec-9-en-1-one Chemical compound O=C1CCCCCCCC=CCCCCCCC1 ZKVZSBSZTMPBQR-UHFFFAOYSA-N 0.000 description 1
- 238000011161 development Methods 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 229920001971 elastomer Polymers 0.000 description 1
- 238000005516 engineering process Methods 0.000 description 1
- 238000011156 evaluation Methods 0.000 description 1
- 230000002349 favourable effect Effects 0.000 description 1
- 230000005251 gamma ray Effects 0.000 description 1
- 125000005843 halogen group Chemical group 0.000 description 1
- XMBWDFGMSWQBCA-UHFFFAOYSA-N hydrogen iodide Chemical compound I XMBWDFGMSWQBCA-UHFFFAOYSA-N 0.000 description 1
- 230000028993 immune response Effects 0.000 description 1
- 238000010348 incorporation Methods 0.000 description 1
- 238000002347 injection Methods 0.000 description 1
- 239000007924 injection Substances 0.000 description 1
- 150000002496 iodine Chemical class 0.000 description 1
- 230000000302 ischemic effect Effects 0.000 description 1
- 210000000265 leukocyte Anatomy 0.000 description 1
- 150000002632 lipids Chemical class 0.000 description 1
- 150000002678 macrocyclic compounds Chemical class 0.000 description 1
- 239000003120 macrolide antibiotic agent Substances 0.000 description 1
- 230000002503 metabolic effect Effects 0.000 description 1
- MYWUZJCMWCOHBA-VIFPVBQESA-N methamphetamine Chemical group CN[C@@H](C)CC1=CC=CC=C1 MYWUZJCMWCOHBA-VIFPVBQESA-N 0.000 description 1
- 238000002156 mixing Methods 0.000 description 1
- 238000012986 modification Methods 0.000 description 1
- 230000004048 modification Effects 0.000 description 1
- CMWTZPSULFXXJA-VIFPVBQESA-N naproxen Chemical group C1=C([C@H](C)C(O)=O)C=CC2=CC(OC)=CC=C21 CMWTZPSULFXXJA-VIFPVBQESA-N 0.000 description 1
- 229910052757 nitrogen Inorganic materials 0.000 description 1
- 238000013421 nuclear magnetic resonance imaging Methods 0.000 description 1
- PGRBVLPTXLOMNB-UHFFFAOYSA-N octadecanolide Natural products O=C1CCCCCCCCCCCCCCCCCO1 PGRBVLPTXLOMNB-UHFFFAOYSA-N 0.000 description 1
- 238000003825 pressing Methods 0.000 description 1
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 1
- 239000011541 reaction mixture Substances 0.000 description 1
- 238000011160 research Methods 0.000 description 1
- NNNVXFKZMRGJPM-KHPPLWFESA-N sapienic acid Chemical compound CCCCCCCCC\C=C/CCCCC(O)=O NNNVXFKZMRGJPM-KHPPLWFESA-N 0.000 description 1
- 239000000243 solution Substances 0.000 description 1
- 239000002904 solvent Substances 0.000 description 1
- 210000000952 spleen Anatomy 0.000 description 1
- 125000001424 substituent group Chemical group 0.000 description 1
- 230000009897 systematic effect Effects 0.000 description 1
- LFSYLMRHJKGLDV-UHFFFAOYSA-N tetradecanolide Natural products O=C1CCCCCCCCCCCCCO1 LFSYLMRHJKGLDV-UHFFFAOYSA-N 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C59/00—Compounds having carboxyl groups bound to acyclic carbon atoms and containing any of the groups OH, O—metal, —CHO, keto, ether, groups, groups, or groups
- C07C59/40—Unsaturated compounds
- C07C59/42—Unsaturated compounds containing hydroxy or O-metal groups
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K51/00—Preparations containing radioactive substances for use in therapy or testing in vivo
- A61K51/02—Preparations containing radioactive substances for use in therapy or testing in vivo characterised by the carrier, i.e. characterised by the agent or material covalently linked or complexing the radioactive nucleus
- A61K51/04—Organic compounds
- A61K51/0402—Organic compounds carboxylic acid carriers, fatty acids
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C53/00—Saturated compounds having only one carboxyl group bound to an acyclic carbon atom or hydrogen
- C07C53/15—Saturated compounds having only one carboxyl group bound to an acyclic carbon atom or hydrogen containing halogen
- C07C53/19—Acids containing three or more carbon atoms
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C57/00—Unsaturated compounds having carboxyl groups bound to acyclic carbon atoms
- C07C57/52—Unsaturated compounds having carboxyl groups bound to acyclic carbon atoms containing halogen
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C59/00—Compounds having carboxyl groups bound to acyclic carbon atoms and containing any of the groups OH, O—metal, —CHO, keto, ether, groups, groups, or groups
- C07C59/185—Saturated compounds having only one carboxyl group and containing keto groups
- C07C59/21—Saturated compounds having only one carboxyl group and containing keto groups containing halogen
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C59/00—Compounds having carboxyl groups bound to acyclic carbon atoms and containing any of the groups OH, O—metal, —CHO, keto, ether, groups, groups, or groups
- C07C59/235—Saturated compounds containing more than one carboxyl group
- C07C59/305—Saturated compounds containing more than one carboxyl group containing ether groups, groups, groups, or groups
- C07C59/315—Saturated compounds containing more than one carboxyl group containing ether groups, groups, groups, or groups containing halogen
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K2123/00—Preparations for testing in vivo
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- Medicinal Chemistry (AREA)
- Physics & Mathematics (AREA)
- Proteomics, Peptides & Aminoacids (AREA)
- Optics & Photonics (AREA)
- Pharmacology & Pharmacy (AREA)
- Epidemiology (AREA)
- Animal Behavior & Ethology (AREA)
- General Health & Medical Sciences (AREA)
- Public Health (AREA)
- Veterinary Medicine (AREA)
- Pyrane Compounds (AREA)
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CA000436822A CA1221105A (fr) | 1983-09-16 | 1983-09-16 | Acides gras halogenes en position omega |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CA000436822A CA1221105A (fr) | 1983-09-16 | 1983-09-16 | Acides gras halogenes en position omega |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CA1221105A true CA1221105A (fr) | 1987-04-28 |
Family
ID=4126083
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CA000436822A Expired CA1221105A (fr) | 1983-09-16 | 1983-09-16 | Acides gras halogenes en position omega |
Country Status (1)
| Country | Link |
|---|---|
| CA (1) | CA1221105A (fr) |
Cited By (9)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| FR2726765A1 (fr) * | 1994-11-14 | 1996-05-15 | Cis Bio Int | Compositions radiopharmaceutiques comprenant un complexe d'inclusion d'une cyclodextrine et d'un acide gras radiohalogene |
| US5726328A (en) * | 1996-07-09 | 1998-03-10 | V. Mane Fils S.A. | Preparation of cis-isoambrettolides and their use as a fragrance |
| US5831101A (en) * | 1996-11-08 | 1998-11-03 | Quest International B.V. | 14-methyl-hexadecenolide and 14-methyl-hexadecanolide |
| AU748249B2 (en) * | 1997-10-09 | 2002-05-30 | Givaudan-Roure (International) Sa | Macrocycles |
| US7569535B2 (en) | 2004-04-30 | 2009-08-04 | Soda Aromatic Co., Ltd. | 11-methyl-13-tridecanolide, 12-methyl-14-tetradecanolide and 13-methyl-15-pentadecanolide, perfume compositions containing the same, and process for production of compounds including the same |
| JP2016175898A (ja) * | 2015-03-20 | 2016-10-06 | 三洋化成工業株式会社 | 環状ポリエーテルエステル、それを含む潤滑油組成物及び環状ポリエーテルエステルの製造方法 |
| CN110819451A (zh) * | 2012-09-14 | 2020-02-21 | 西姆莱斯股份公司 | 作为添味剂的不饱和内酯 |
| CN114573541A (zh) * | 2020-11-30 | 2022-06-03 | 中国科学院上海有机化学研究所 | 内酯类化合物及铈催化的内酯类化合物的合成方法 |
| US11549131B2 (en) | 2018-07-17 | 2023-01-10 | Conagen Inc. | Biosynthetic production of gamma-lactones |
-
1983
- 1983-09-16 CA CA000436822A patent/CA1221105A/fr not_active Expired
Cited By (15)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| FR2726765A1 (fr) * | 1994-11-14 | 1996-05-15 | Cis Bio Int | Compositions radiopharmaceutiques comprenant un complexe d'inclusion d'une cyclodextrine et d'un acide gras radiohalogene |
| WO1996014881A1 (fr) * | 1994-11-14 | 1996-05-23 | Cis Bio International | Complexe d'inclusion d'un acide gras radiohalogene dans une cyclodextrine |
| US5726328A (en) * | 1996-07-09 | 1998-03-10 | V. Mane Fils S.A. | Preparation of cis-isoambrettolides and their use as a fragrance |
| EP0818452A3 (fr) * | 1996-07-09 | 1998-03-11 | V. Mane Fils S.A. | Préparation de cis-isoambrettolides et leur usage comme parfum |
| US5786321A (en) * | 1996-07-09 | 1998-07-28 | V. Mane Fils S.A. | Preparation of cis-isoambrettolidies and their use as a fragrance |
| US5831101A (en) * | 1996-11-08 | 1998-11-03 | Quest International B.V. | 14-methyl-hexadecenolide and 14-methyl-hexadecanolide |
| AU748249B2 (en) * | 1997-10-09 | 2002-05-30 | Givaudan-Roure (International) Sa | Macrocycles |
| EP0908455B1 (fr) * | 1997-10-09 | 2002-07-10 | Givaudan SA | Macrocycles |
| US7569535B2 (en) | 2004-04-30 | 2009-08-04 | Soda Aromatic Co., Ltd. | 11-methyl-13-tridecanolide, 12-methyl-14-tetradecanolide and 13-methyl-15-pentadecanolide, perfume compositions containing the same, and process for production of compounds including the same |
| CN110819451A (zh) * | 2012-09-14 | 2020-02-21 | 西姆莱斯股份公司 | 作为添味剂的不饱和内酯 |
| JP2016175898A (ja) * | 2015-03-20 | 2016-10-06 | 三洋化成工業株式会社 | 環状ポリエーテルエステル、それを含む潤滑油組成物及び環状ポリエーテルエステルの製造方法 |
| US11549131B2 (en) | 2018-07-17 | 2023-01-10 | Conagen Inc. | Biosynthetic production of gamma-lactones |
| US12480147B2 (en) | 2018-07-17 | 2025-11-25 | Conagen Inc. | Biosynthetic production of gamma-lactones |
| CN114573541A (zh) * | 2020-11-30 | 2022-06-03 | 中国科学院上海有机化学研究所 | 内酯类化合物及铈催化的内酯类化合物的合成方法 |
| CN114573541B (zh) * | 2020-11-30 | 2026-03-06 | 中国科学院上海有机化学研究所 | 内酯类化合物及铈催化的内酯类化合物的合成方法 |
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| Date | Code | Title | Description |
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| MKEX | Expiry |