ES2692179T3 - Compuestos capaces de liberar compuestos fragantes - Google Patents
Compuestos capaces de liberar compuestos fragantes Download PDFInfo
- Publication number
- ES2692179T3 ES2692179T3 ES11805863.5T ES11805863T ES2692179T3 ES 2692179 T3 ES2692179 T3 ES 2692179T3 ES 11805863 T ES11805863 T ES 11805863T ES 2692179 T3 ES2692179 T3 ES 2692179T3
- Authority
- ES
- Spain
- Prior art keywords
- alkyl
- enyl
- methyl
- ring
- hydrogen
- 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.)
- Active
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- 150000001875 compounds Chemical class 0.000 title claims abstract description 142
- -1 2- (2- (4-methylcyclohex-3-en-1-yl) propyl) cyclopent-1-ylidene Chemical group 0.000 claims abstract description 84
- 229910052739 hydrogen Inorganic materials 0.000 claims abstract description 59
- 239000001257 hydrogen Substances 0.000 claims abstract description 59
- 239000002243 precursor Substances 0.000 claims abstract description 44
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims abstract description 37
- 125000004178 (C1-C4) alkyl group Chemical group 0.000 claims abstract description 33
- 125000000217 alkyl group Chemical group 0.000 claims abstract description 33
- 125000003118 aryl group Chemical group 0.000 claims abstract description 26
- 125000000392 cycloalkenyl group Chemical group 0.000 claims abstract description 24
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims abstract description 23
- 150000001299 aldehydes Chemical class 0.000 claims abstract description 23
- 125000001033 ether group Chemical group 0.000 claims abstract description 23
- 125000003342 alkenyl group Chemical group 0.000 claims abstract description 22
- 150000002576 ketones Chemical class 0.000 claims abstract description 22
- 125000006527 (C1-C5) alkyl group Chemical group 0.000 claims abstract description 20
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims abstract description 20
- 125000001301 ethoxy group Chemical group [H]C([H])([H])C([H])([H])O* 0.000 claims abstract description 19
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims abstract description 19
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 claims abstract description 17
- 150000002431 hydrogen Chemical group 0.000 claims abstract description 16
- 125000000753 cycloalkyl group Chemical group 0.000 claims abstract description 14
- 125000004432 carbon atom Chemical group C* 0.000 claims abstract description 10
- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 claims abstract description 10
- 229920002554 vinyl polymer Chemical group 0.000 claims abstract description 10
- 150000001728 carbonyl compounds Chemical class 0.000 claims abstract description 9
- 125000000081 (C5-C8) cycloalkenyl group Chemical group 0.000 claims abstract description 8
- 125000005915 C6-C14 aryl group Chemical group 0.000 claims abstract description 8
- 125000006273 (C1-C3) alkyl group Chemical group 0.000 claims abstract description 7
- 125000001118 alkylidene group Chemical group 0.000 claims abstract description 7
- 230000003647 oxidation Effects 0.000 claims abstract description 7
- 238000007254 oxidation reaction Methods 0.000 claims abstract description 7
- 229910052799 carbon Inorganic materials 0.000 claims abstract description 6
- 230000002269 spontaneous effect Effects 0.000 claims abstract description 6
- 125000004430 oxygen atom Chemical group O* 0.000 claims abstract description 5
- 125000004169 (C1-C6) alkyl group Chemical group 0.000 claims abstract description 4
- 125000006729 (C2-C5) alkenyl group Chemical group 0.000 claims abstract description 4
- 125000002619 bicyclic group Chemical group 0.000 claims abstract description 4
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 claims description 72
- 239000000203 mixture Substances 0.000 claims description 41
- 238000000034 method Methods 0.000 claims description 15
- UFWIBTONFRDIAS-UHFFFAOYSA-N Naphthalene Chemical compound C1=CC=CC2=CC=CC=C21 UFWIBTONFRDIAS-UHFFFAOYSA-N 0.000 claims description 14
- CBOQJANXLMLOSS-UHFFFAOYSA-N ethyl vanillin Chemical compound CCOC1=CC(C=O)=CC=C1O CBOQJANXLMLOSS-UHFFFAOYSA-N 0.000 claims description 14
- NFAVNWJJYQAGNB-UHFFFAOYSA-N 2-methylundecanal Chemical compound CCCCCCCCCC(C)C=O NFAVNWJJYQAGNB-UHFFFAOYSA-N 0.000 claims description 12
- OHRBQTOZYGEWCJ-UHFFFAOYSA-N 3-(3-propan-2-ylphenyl)butanal Chemical compound CC(C)C1=CC=CC(C(C)CC=O)=C1 OHRBQTOZYGEWCJ-UHFFFAOYSA-N 0.000 claims description 12
- KWOLFJPFCHCOCG-UHFFFAOYSA-N Acetophenone Chemical compound CC(=O)C1=CC=CC=C1 KWOLFJPFCHCOCG-UHFFFAOYSA-N 0.000 claims description 10
- 125000005605 benzo group Chemical group 0.000 claims description 10
- 150000002430 hydrocarbons Chemical group 0.000 claims description 10
- SATCULPHIDQDRE-UHFFFAOYSA-N piperonal Chemical compound O=CC1=CC=C2OCOC2=C1 SATCULPHIDQDRE-UHFFFAOYSA-N 0.000 claims description 9
- HUMNYLRZRPPJDN-UHFFFAOYSA-N benzaldehyde Chemical compound O=CC1=CC=CC=C1 HUMNYLRZRPPJDN-UHFFFAOYSA-N 0.000 claims description 8
- 229940073505 ethyl vanillin Drugs 0.000 claims description 8
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 7
- XSAYZAUNJMRRIR-UHFFFAOYSA-N 2-acetylnaphthalene Chemical compound C1=CC=CC2=CC(C(=O)C)=CC=C21 XSAYZAUNJMRRIR-UHFFFAOYSA-N 0.000 claims description 6
- 125000004172 4-methoxyphenyl group Chemical group [H]C1=C([H])C(OC([H])([H])[H])=C([H])C([H])=C1* 0.000 claims description 6
- NBBJYMSMWIIQGU-UHFFFAOYSA-N Propionic aldehyde Chemical compound CCC=O NBBJYMSMWIIQGU-UHFFFAOYSA-N 0.000 claims description 6
- VWMVAQHMFFZQGD-UHFFFAOYSA-N p-Hydroxybenzyl acetone Natural products CC(=O)CC1=CC=C(O)C=C1 VWMVAQHMFFZQGD-UHFFFAOYSA-N 0.000 claims description 6
- NJGBTKGETPDVIK-UHFFFAOYSA-N raspberry ketone Chemical compound CC(=O)CCC1=CC=C(O)C=C1 NJGBTKGETPDVIK-UHFFFAOYSA-N 0.000 claims description 6
- UCSIFMPORANABL-UHFFFAOYSA-N 3,7-dimethyloctanal Chemical compound CC(C)CCCC(C)CC=O UCSIFMPORANABL-UHFFFAOYSA-N 0.000 claims description 5
- CIXAYNMKFFQEFU-UHFFFAOYSA-N (4-Methylphenyl)acetaldehyde Chemical compound CC1=CC=C(CC=O)C=C1 CIXAYNMKFFQEFU-UHFFFAOYSA-N 0.000 claims description 4
- FTNJQNQLEGKTGD-UHFFFAOYSA-N 1,3-benzodioxole Chemical compound C1=CC=C2OCOC2=C1 FTNJQNQLEGKTGD-UHFFFAOYSA-N 0.000 claims description 4
- 125000003903 2-propenyl group Chemical group [H]C([*])([H])C([H])=C([H])[H] 0.000 claims description 4
- WTPYRCJDOZVZON-UHFFFAOYSA-N 3,5,5-Trimethylhexanal Chemical compound O=CCC(C)CC(C)(C)C WTPYRCJDOZVZON-UHFFFAOYSA-N 0.000 claims description 4
- NTPLXRHDUXRPNE-UHFFFAOYSA-N 4-methoxyacetophenone Chemical compound COC1=CC=C(C(C)=O)C=C1 NTPLXRHDUXRPNE-UHFFFAOYSA-N 0.000 claims description 4
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims description 4
- NEHNMFOYXAPHSD-UHFFFAOYSA-N citronellal Chemical compound O=CCC(C)CCC=C(C)C NEHNMFOYXAPHSD-UHFFFAOYSA-N 0.000 claims description 4
- KSMVZQYAVGTKIV-UHFFFAOYSA-N decanal Chemical compound CCCCCCCCCC=O KSMVZQYAVGTKIV-UHFFFAOYSA-N 0.000 claims description 4
- HFJRKMMYBMWEAD-UHFFFAOYSA-N dodecanal Chemical compound CCCCCCCCCCCC=O HFJRKMMYBMWEAD-UHFFFAOYSA-N 0.000 claims description 4
- FXHGMKSSBGDXIY-UHFFFAOYSA-N heptanal Chemical compound CCCCCCC=O FXHGMKSSBGDXIY-UHFFFAOYSA-N 0.000 claims description 4
- WPFVBOQKRVRMJB-UHFFFAOYSA-N hydroxycitronellal Chemical compound O=CCC(C)CCCC(C)(C)O WPFVBOQKRVRMJB-UHFFFAOYSA-N 0.000 claims description 4
- GYHFUZHODSMOHU-UHFFFAOYSA-N nonanal Chemical compound CCCCCCCCC=O GYHFUZHODSMOHU-UHFFFAOYSA-N 0.000 claims description 4
- NUJGJRNETVAIRJ-UHFFFAOYSA-N octanal Chemical compound CCCCCCCC=O NUJGJRNETVAIRJ-UHFFFAOYSA-N 0.000 claims description 4
- QJJDNZGPQDGNDX-UHFFFAOYSA-N oxidized Latia luciferin Chemical compound CC(=O)CCC1=C(C)CCCC1(C)C QJJDNZGPQDGNDX-UHFFFAOYSA-N 0.000 claims description 4
- 229910052760 oxygen Inorganic materials 0.000 claims description 4
- 239000001301 oxygen Substances 0.000 claims description 4
- ZRSNZINYAWTAHE-UHFFFAOYSA-N p-methoxybenzaldehyde Chemical compound COC1=CC=C(C=O)C=C1 ZRSNZINYAWTAHE-UHFFFAOYSA-N 0.000 claims description 4
- QNGNSVIICDLXHT-UHFFFAOYSA-N para-ethylbenzaldehyde Natural products CCC1=CC=C(C=O)C=C1 QNGNSVIICDLXHT-UHFFFAOYSA-N 0.000 claims description 4
- 230000008569 process Effects 0.000 claims description 4
- 150000003254 radicals Chemical class 0.000 claims description 4
- BGEHHAVMRVXCGR-UHFFFAOYSA-N tridecanal Chemical compound CCCCCCCCCCCCC=O BGEHHAVMRVXCGR-UHFFFAOYSA-N 0.000 claims description 4
- KMPQYAYAQWNLME-UHFFFAOYSA-N undecanal Chemical compound CCCCCCCCCCC=O KMPQYAYAQWNLME-UHFFFAOYSA-N 0.000 claims description 4
- PSQYTAPXSHCGMF-BQYQJAHWSA-N β-ionone Chemical compound CC(=O)\C=C\C1=C(C)CCCC1(C)C PSQYTAPXSHCGMF-BQYQJAHWSA-N 0.000 claims description 4
- 239000001304 (2R)-2,6-dimethylhept-5-enal Substances 0.000 claims description 3
- YGFGZTXGYTUXBA-UHFFFAOYSA-N (±)-2,6-dimethyl-5-heptenal Chemical compound O=CC(C)CCC=C(C)C YGFGZTXGYTUXBA-UHFFFAOYSA-N 0.000 claims description 3
- QEUCRVAOUUCNJV-UHFFFAOYSA-N 1,2-dimethoxy-4-[4-(3-propan-2-ylphenyl)pent-1-enyl]benzene Chemical compound C1=C(OC)C(OC)=CC=C1C=CCC(C)C1=CC=CC(C(C)C)=C1 QEUCRVAOUUCNJV-UHFFFAOYSA-N 0.000 claims description 3
- UYIUDXMQYWPVAY-UHFFFAOYSA-N 1-(2,2-dimethyl-5-phenylpent-3-enyl)-4-ethylbenzene Chemical compound C1=CC(CC)=CC=C1CC(C)(C)C=CCC1=CC=CC=C1 UYIUDXMQYWPVAY-UHFFFAOYSA-N 0.000 claims description 3
- AOTOGNPVLZNOPY-UHFFFAOYSA-N 1-(6-phenylhex-4-en-2-yl)-3-propan-2-ylbenzene Chemical compound CC(C)C1=CC=CC(C(C)CC=CCC=2C=CC=CC=2)=C1 AOTOGNPVLZNOPY-UHFFFAOYSA-N 0.000 claims description 3
- KZXNEQMEXJAKKD-UHFFFAOYSA-N 1-methoxy-4-(3-methyldodec-1-enyl)benzene Chemical compound CCCCCCCCCC(C)C=CC1=CC=C(OC)C=C1 KZXNEQMEXJAKKD-UHFFFAOYSA-N 0.000 claims description 3
- UJWBRAKSLNDKPA-UHFFFAOYSA-N 1-methoxy-4-(4-methyltridec-2-enyl)benzene Chemical compound CCCCCCCCCC(C)C=CCC1=CC=C(OC)C=C1 UJWBRAKSLNDKPA-UHFFFAOYSA-N 0.000 claims description 3
- DWGHUWXJHKXZNA-UHFFFAOYSA-N 1-methoxy-4-[5-(3-propan-2-ylphenyl)hex-2-enyl]benzene Chemical compound C1=CC(OC)=CC=C1CC=CCC(C)C1=CC=CC(C(C)C)=C1 DWGHUWXJHKXZNA-UHFFFAOYSA-N 0.000 claims description 3
- GOCMOBASIPUBEQ-UHFFFAOYSA-N 1-methyl-4-(4-methyltridec-2-enyl)benzene Chemical compound CCCCCCCCCC(C)C=CCC1=CC=C(C)C=C1 GOCMOBASIPUBEQ-UHFFFAOYSA-N 0.000 claims description 3
- NXTMGVQDFYDTMX-UHFFFAOYSA-N 2-(4-methyltridec-2-en-2-yl)naphthalene Chemical compound C1=CC=CC2=CC(C(C)=CC(C)CCCCCCCCC)=CC=C21 NXTMGVQDFYDTMX-UHFFFAOYSA-N 0.000 claims description 3
- REJVAHLIIJLJJB-UHFFFAOYSA-N 2-(4-methyltridec-2-enyl)naphthalene Chemical compound C1=CC=CC2=CC(CC=CC(C)CCCCCCCCC)=CC=C21 REJVAHLIIJLJJB-UHFFFAOYSA-N 0.000 claims description 3
- FSKGFRBHGXIDSA-UHFFFAOYSA-N 2-(4-propan-2-ylphenyl)acetaldehyde Chemical compound CC(C)C1=CC=C(CC=O)C=C1 FSKGFRBHGXIDSA-UHFFFAOYSA-N 0.000 claims description 3
- UABARRYYLZLXFQ-UHFFFAOYSA-N 2-(5,7,7-trimethyloct-2-en-2-yl)naphthalene Chemical compound C1=CC=CC2=CC(C(C)=CCC(C)CC(C)(C)C)=CC=C21 UABARRYYLZLXFQ-UHFFFAOYSA-N 0.000 claims description 3
- DNRJTBAOUJJKDY-UHFFFAOYSA-N 2-Acetyl-3,5,5,6,8,8-hexamethyl-5,6,7,8- tetrahydronaphthalene Chemical compound CC(=O)C1=C(C)C=C2C(C)(C)C(C)CC(C)(C)C2=C1 DNRJTBAOUJJKDY-UHFFFAOYSA-N 0.000 claims description 3
- KNHGOYVXAHUDHP-UHFFFAOYSA-N 2-[2-(4-methylcyclohex-3-en-1-yl)propyl]cyclopentan-1-one Chemical compound C1CC(C)=CCC1C(C)CC1CCCC1=O KNHGOYVXAHUDHP-UHFFFAOYSA-N 0.000 claims description 3
- DKZCDROPRPTSPC-UHFFFAOYSA-N 2-[4-(4-methoxyphenyl)but-2-en-2-yl]naphthalene Chemical compound C1=CC(OC)=CC=C1CC=C(C)C1=CC=C(C=CC=C2)C2=C1 DKZCDROPRPTSPC-UHFFFAOYSA-N 0.000 claims description 3
- HWZFXDCEAQCFDY-UHFFFAOYSA-N 2-ethoxy-4-(3-methyldodec-1-enyl)phenol Chemical compound CCCCCCCCCC(C)C=CC1=CC=C(O)C(OCC)=C1 HWZFXDCEAQCFDY-UHFFFAOYSA-N 0.000 claims description 3
- NNACZGJXARUDAC-UHFFFAOYSA-N 2-ethoxy-4-[3-(4-methoxyphenyl)prop-1-enyl]phenol Chemical compound C1=C(O)C(OCC)=CC(C=CCC=2C=CC(OC)=CC=2)=C1 NNACZGJXARUDAC-UHFFFAOYSA-N 0.000 claims description 3
- PEMWPSNVRCCJEF-UHFFFAOYSA-N 2-ethoxy-4-[3-(4-methylphenyl)prop-1-enyl]phenol Chemical compound C1=C(O)C(OCC)=CC(C=CCC=2C=CC(C)=CC=2)=C1 PEMWPSNVRCCJEF-UHFFFAOYSA-N 0.000 claims description 3
- HPOLMMDGJCOVPT-UHFFFAOYSA-N 2-ethoxy-4-[4-(3-propan-2-ylphenyl)pent-1-enyl]phenol Chemical compound C1=C(O)C(OCC)=CC(C=CCC(C)C=2C=C(C=CC=2)C(C)C)=C1 HPOLMMDGJCOVPT-UHFFFAOYSA-N 0.000 claims description 3
- MKSARIDKCHNUPI-UHFFFAOYSA-N 2-ethoxy-4-[4-(4-hydroxyphenyl)-2-methylbut-1-enyl]phenol Chemical compound C1=C(O)C(OCC)=CC(C=C(C)CCC=2C=CC(O)=CC=2)=C1 MKSARIDKCHNUPI-UHFFFAOYSA-N 0.000 claims description 3
- KQPOAOFGDJVJIB-UHFFFAOYSA-N 2-ethoxy-4-[[2-[2-(4-methylcyclohex-3-en-1-yl)propyl]cyclopentylidene]methyl]phenol Chemical compound C1=C(O)C(OCC)=CC(C=C2C(CCC2)CC(C)C2CC=C(C)CC2)=C1 KQPOAOFGDJVJIB-UHFFFAOYSA-N 0.000 claims description 3
- JFTSYAALCNQOKO-UHFFFAOYSA-N 3-(4-ethylphenyl)-2,2-dimethylpropanal Chemical compound CCC1=CC=C(CC(C)(C)C=O)C=C1 JFTSYAALCNQOKO-UHFFFAOYSA-N 0.000 claims description 3
- VLFBSPUPYFTTNF-UHFFFAOYSA-N 3-(4-methoxyphenyl)-2-methylpropanal Chemical compound COC1=CC=C(CC(C)C=O)C=C1 VLFBSPUPYFTTNF-UHFFFAOYSA-N 0.000 claims description 3
- VESJWQHRSCMIBZ-UHFFFAOYSA-N 4-(3-methyl-5-phenylpent-3-enyl)phenol Chemical compound C=1C=CC=CC=1CC=C(C)CCC1=CC=C(O)C=C1 VESJWQHRSCMIBZ-UHFFFAOYSA-N 0.000 claims description 3
- XBZCSTFFBHIBLJ-UHFFFAOYSA-N 4-(6-methylheptan-2-yloxy)butanal Chemical compound CC(C)CCCC(C)OCCCC=O XBZCSTFFBHIBLJ-UHFFFAOYSA-N 0.000 claims description 3
- NICBGBURNHAUSX-UHFFFAOYSA-N 4-methyltridec-2-enylbenzene Chemical compound CCCCCCCCCC(C)C=CCC1=CC=CC=C1 NICBGBURNHAUSX-UHFFFAOYSA-N 0.000 claims description 3
- VEECHONXFDSHGR-UHFFFAOYSA-N 5,7,7-trimethyloct-2-enylbenzene Chemical compound CC(C)(C)CC(C)CC=CCC1=CC=CC=C1 VEECHONXFDSHGR-UHFFFAOYSA-N 0.000 claims description 3
- SXMVVQIOWWIFFL-UHFFFAOYSA-N 5-[4-(3-propan-2-ylphenyl)pent-1-enyl]-1,3-benzodioxole Chemical compound CC(C)C1=CC=CC(C(C)CC=CC=2C=C3OCOC3=CC=2)=C1 SXMVVQIOWWIFFL-UHFFFAOYSA-N 0.000 claims description 3
- AFGBVLFOIJOYOV-UHFFFAOYSA-N 6-(6-methylheptan-2-yloxy)hex-2-enylbenzene Chemical compound CC(C)CCCC(C)OCCCC=CCC1=CC=CC=C1 AFGBVLFOIJOYOV-UHFFFAOYSA-N 0.000 claims description 3
- ISWSIDIOOBJBQZ-UHFFFAOYSA-N Phenol Chemical compound OC1=CC=CC=C1 ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 claims description 3
- GXANMBISFKBPEX-ARJAWSKDSA-N cis-3-hexenal Chemical compound CC\C=C/CC=O GXANMBISFKBPEX-ARJAWSKDSA-N 0.000 claims description 3
- MWOOGOJBHIARFG-UHFFFAOYSA-N vanillin Chemical compound COC1=CC(C=O)=CC=C1O MWOOGOJBHIARFG-UHFFFAOYSA-N 0.000 claims description 3
- 235000012141 vanillin Nutrition 0.000 claims description 3
- FGQOOHJZONJGDT-UHFFFAOYSA-N vanillin Natural products COC1=CC(O)=CC(C=O)=C1 FGQOOHJZONJGDT-UHFFFAOYSA-N 0.000 claims description 3
- SFEOKXHPFMOVRM-UHFFFAOYSA-N (+)-(S)-gamma-ionone Natural products CC(=O)C=CC1C(=C)CCCC1(C)C SFEOKXHPFMOVRM-UHFFFAOYSA-N 0.000 claims description 2
- MBDOYVRWFFCFHM-SNAWJCMRSA-N (2E)-hexenal Chemical compound CCC\C=C\C=O MBDOYVRWFFCFHM-SNAWJCMRSA-N 0.000 claims description 2
- QAFGEOHWEQLURJ-DHZHZOJOSA-N (2e)-2,4-diethylhepta-2,6-dienal Chemical compound C=CCC(CC)\C=C(/CC)C=O QAFGEOHWEQLURJ-DHZHZOJOSA-N 0.000 claims description 2
- MIHSPYMZXYONJN-RMKNXTFCSA-N (2e)-2,4-dimethylhepta-2,6-dienal Chemical compound C=CCC(C)\C=C(/C)C=O MIHSPYMZXYONJN-RMKNXTFCSA-N 0.000 claims description 2
- 125000006592 (C2-C3) alkenyl group Chemical group 0.000 claims description 2
- KJPRLNWUNMBNBZ-QPJJXVBHSA-N (E)-cinnamaldehyde Chemical compound O=C\C=C\C1=CC=CC=C1 KJPRLNWUNMBNBZ-QPJJXVBHSA-N 0.000 claims description 2
- 239000001727 (E)-dec-2-enal Substances 0.000 claims description 2
- 239000001541 (E)-dodec-2-enal Substances 0.000 claims description 2
- SSNZFFBDIMUILS-ZHACJKMWSA-N (E)-dodec-2-enal Chemical compound CCCCCCCCC\C=C\C=O SSNZFFBDIMUILS-ZHACJKMWSA-N 0.000 claims description 2
- 239000001179 (E)-hex-2-enal Substances 0.000 claims description 2
- 239000001381 (E)-non-2-enal Substances 0.000 claims description 2
- 239000001118 (E)-tridec-2-enal Substances 0.000 claims description 2
- FXCYGAGBPZQRJE-ZHACJKMWSA-N 1-(2,6,6-Trimethyl-2-cyclohexen-1-yl)-1,6-heptadien-3-one Chemical compound CC1=CCCC(C)(C)C1\C=C\C(=O)CCC=C FXCYGAGBPZQRJE-ZHACJKMWSA-N 0.000 claims description 2
- ZXBDNMZZYXFGFN-UTOQUPLUSA-N 1-[(1z,4z)-hepta-1,4-dienyl]-4-methoxybenzene Chemical compound CC\C=C/C\C=C/C1=CC=C(OC)C=C1 ZXBDNMZZYXFGFN-UTOQUPLUSA-N 0.000 claims description 2
- QDXMENJMYZDCFA-UHFFFAOYSA-N 1-methoxy-4-[3-(4-methylphenyl)prop-1-enyl]benzene Chemical compound C1=CC(OC)=CC=C1C=CCC1=CC=C(C)C=C1 QDXMENJMYZDCFA-UHFFFAOYSA-N 0.000 claims description 2
- JAQGIJPTXZEVJS-UHFFFAOYSA-N 1-methoxy-4-[4-[4-(2-methylpropyl)phenyl]but-1-enyl]benzene Chemical compound C1=CC(OC)=CC=C1C=CCCC1=CC=C(CC(C)C)C=C1 JAQGIJPTXZEVJS-UHFFFAOYSA-N 0.000 claims description 2
- OFHHDSQXFXLTKC-UHFFFAOYSA-N 10-undecenal Chemical compound C=CCCCCCCCCC=O OFHHDSQXFXLTKC-UHFFFAOYSA-N 0.000 claims description 2
- KZSUMHASCAWKLE-UHFFFAOYSA-N 2,3,3-trimethyl-2h-inden-1-one Chemical compound C1=CC=C2C(C)(C)C(C)C(=O)C2=C1 KZSUMHASCAWKLE-UHFFFAOYSA-N 0.000 claims description 2
- UEGBWDUVDAKUGA-UHFFFAOYSA-N 2,6,10-trimethylundec-9-enal Chemical compound CC(C)=CCCC(C)CCCC(C)C=O UEGBWDUVDAKUGA-UHFFFAOYSA-N 0.000 claims description 2
- RMPKHUJAYKUKPH-UHFFFAOYSA-N 2,6-dimethyloct-5-enal Chemical compound CCC(C)=CCCC(C)C=O RMPKHUJAYKUKPH-UHFFFAOYSA-N 0.000 claims description 2
- NRIVMXXOUOBRAG-UHFFFAOYSA-N 2-(4-methoxyphenyl)acetaldehyde Chemical compound COC1=CC=C(CC=O)C=C1 NRIVMXXOUOBRAG-UHFFFAOYSA-N 0.000 claims description 2
- IZQUWQPXCQLTJY-UHFFFAOYSA-N 2-(4-propan-2-ylphenyl)propanal Chemical compound CC(C)C1=CC=C(C(C)C=O)C=C1 IZQUWQPXCQLTJY-UHFFFAOYSA-N 0.000 claims description 2
- SSNZFFBDIMUILS-UHFFFAOYSA-N 2-Dodecenal Natural products CCCCCCCCCC=CC=O SSNZFFBDIMUILS-UHFFFAOYSA-N 0.000 claims description 2
- BSAIUMLZVGUGKX-UHFFFAOYSA-N 2-Nonenal Natural products CCCCCCC=CC=O BSAIUMLZVGUGKX-UHFFFAOYSA-N 0.000 claims description 2
- FWTGHNUSSMOOHX-NZHODUKLSA-N 2-[(11e)-trideca-2,11-dien-2-yl]naphthalene Chemical compound C1=CC=CC2=CC(C(C)=CCCCCCCC/C=C/C)=CC=C21 FWTGHNUSSMOOHX-NZHODUKLSA-N 0.000 claims description 2
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- SJWNHAXIZWAFOH-UHFFFAOYSA-N 2-[5-(3-propan-2-ylphenyl)hex-2-en-2-yl]naphthalene Chemical compound CC(C)C1=CC=CC(C(C)CC=C(C)C=2C=C3C=CC=CC3=CC=2)=C1 SJWNHAXIZWAFOH-UHFFFAOYSA-N 0.000 claims description 2
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- UZFLPKAIBPNNCA-FPLPWBNLSA-N α-ionone Chemical compound CC(=O)\C=C/C1C(C)=CCCC1(C)C UZFLPKAIBPNNCA-FPLPWBNLSA-N 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C15/00—Cyclic hydrocarbons containing only six-membered aromatic rings as cyclic parts
- C07C15/40—Cyclic hydrocarbons containing only six-membered aromatic rings as cyclic parts substituted by unsaturated carbon radicals
- C07C15/42—Cyclic hydrocarbons containing only six-membered aromatic rings as cyclic parts substituted by unsaturated carbon radicals monocyclic
- C07C15/44—Cyclic hydrocarbons containing only six-membered aromatic rings as cyclic parts substituted by unsaturated carbon radicals monocyclic the hydrocarbon substituent containing a carbon-to-carbon double bond
-
- C—CHEMISTRY; METALLURGY
- C11—ANIMAL OR VEGETABLE OILS, FATS, FATTY SUBSTANCES OR WAXES; FATTY ACIDS THEREFROM; DETERGENTS; CANDLES
- C11B—PRODUCING, e.g. BY PRESSING RAW MATERIALS OR BY EXTRACTION FROM WASTE MATERIALS, REFINING OR PRESERVING FATS, FATTY SUBSTANCES, e.g. LANOLIN, FATTY OILS OR WAXES; ESSENTIAL OILS; PERFUMES
- C11B9/00—Essential oils; Perfumes
- C11B9/0007—Aliphatic compounds
- C11B9/0015—Aliphatic compounds containing oxygen as the only heteroatom
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C15/00—Cyclic hydrocarbons containing only six-membered aromatic rings as cyclic parts
- C07C15/40—Cyclic hydrocarbons containing only six-membered aromatic rings as cyclic parts substituted by unsaturated carbon radicals
- C07C15/50—Cyclic hydrocarbons containing only six-membered aromatic rings as cyclic parts substituted by unsaturated carbon radicals polycyclic non-condensed
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C15/00—Cyclic hydrocarbons containing only six-membered aromatic rings as cyclic parts
- C07C15/40—Cyclic hydrocarbons containing only six-membered aromatic rings as cyclic parts substituted by unsaturated carbon radicals
- C07C15/56—Cyclic hydrocarbons containing only six-membered aromatic rings as cyclic parts substituted by unsaturated carbon radicals polycyclic condensed
- C07C15/58—Cyclic hydrocarbons containing only six-membered aromatic rings as cyclic parts substituted by unsaturated carbon radicals polycyclic condensed containing two rings
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C43/00—Ethers; Compounds having groups, groups or groups
- C07C43/02—Ethers
- C07C43/20—Ethers having an ether-oxygen atom bound to a carbon atom of a six-membered aromatic ring
- C07C43/215—Ethers having an ether-oxygen atom bound to a carbon atom of a six-membered aromatic ring having unsaturation outside the six-membered aromatic rings
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C43/00—Ethers; Compounds having groups, groups or groups
- C07C43/02—Ethers
- C07C43/20—Ethers having an ether-oxygen atom bound to a carbon atom of a six-membered aromatic ring
- C07C43/23—Ethers having an ether-oxygen atom bound to a carbon atom of a six-membered aromatic ring containing hydroxy or O-metal 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
- C07C45/32—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by oxidation with molecular oxygen
- C07C45/33—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by oxidation with molecular oxygen of CHx-moieties
- C07C45/34—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by oxidation with molecular oxygen of CHx-moieties in unsaturated compounds
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D317/00—Heterocyclic compounds containing five-membered rings having two oxygen atoms as the only ring hetero atoms
- C07D317/08—Heterocyclic compounds containing five-membered rings having two oxygen atoms as the only ring hetero atoms having the hetero atoms in positions 1 and 3
- C07D317/44—Heterocyclic compounds containing five-membered rings having two oxygen atoms as the only ring hetero atoms having the hetero atoms in positions 1 and 3 ortho- or peri-condensed with carbocyclic rings or ring systems
- C07D317/46—Heterocyclic compounds containing five-membered rings having two oxygen atoms as the only ring hetero atoms having the hetero atoms in positions 1 and 3 ortho- or peri-condensed with carbocyclic rings or ring systems condensed with one six-membered ring
- C07D317/48—Methylenedioxybenzenes or hydrogenated methylenedioxybenzenes, unsubstituted on the hetero ring
- C07D317/50—Methylenedioxybenzenes or hydrogenated methylenedioxybenzenes, unsubstituted on the hetero ring with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached to atoms of the carbocyclic ring
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D317/00—Heterocyclic compounds containing five-membered rings having two oxygen atoms as the only ring hetero atoms
- C07D317/08—Heterocyclic compounds containing five-membered rings having two oxygen atoms as the only ring hetero atoms having the hetero atoms in positions 1 and 3
- C07D317/44—Heterocyclic compounds containing five-membered rings having two oxygen atoms as the only ring hetero atoms having the hetero atoms in positions 1 and 3 ortho- or peri-condensed with carbocyclic rings or ring systems
- C07D317/46—Heterocyclic compounds containing five-membered rings having two oxygen atoms as the only ring hetero atoms having the hetero atoms in positions 1 and 3 ortho- or peri-condensed with carbocyclic rings or ring systems condensed with one six-membered ring
- C07D317/48—Methylenedioxybenzenes or hydrogenated methylenedioxybenzenes, unsubstituted on the hetero ring
- C07D317/50—Methylenedioxybenzenes or hydrogenated methylenedioxybenzenes, unsubstituted on the hetero ring with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached to atoms of the carbocyclic ring
- C07D317/54—Radicals substituted by oxygen atoms
-
- C—CHEMISTRY; METALLURGY
- C11—ANIMAL OR VEGETABLE OILS, FATS, FATTY SUBSTANCES OR WAXES; FATTY ACIDS THEREFROM; DETERGENTS; CANDLES
- C11B—PRODUCING, e.g. BY PRESSING RAW MATERIALS OR BY EXTRACTION FROM WASTE MATERIALS, REFINING OR PRESERVING FATS, FATTY SUBSTANCES, e.g. LANOLIN, FATTY OILS OR WAXES; ESSENTIAL OILS; PERFUMES
- C11B9/00—Essential oils; Perfumes
- C11B9/0003—Compounds of unspecified constitution defined by the chemical reaction for their preparation
-
- C—CHEMISTRY; METALLURGY
- C11—ANIMAL OR VEGETABLE OILS, FATS, FATTY SUBSTANCES OR WAXES; FATTY ACIDS THEREFROM; DETERGENTS; CANDLES
- C11B—PRODUCING, e.g. BY PRESSING RAW MATERIALS OR BY EXTRACTION FROM WASTE MATERIALS, REFINING OR PRESERVING FATS, FATTY SUBSTANCES, e.g. LANOLIN, FATTY OILS OR WAXES; ESSENTIAL OILS; PERFUMES
- C11B9/00—Essential oils; Perfumes
- C11B9/0042—Essential oils; Perfumes compounds containing condensed hydrocarbon rings
- C11B9/0046—Essential oils; Perfumes compounds containing condensed hydrocarbon rings containing only two condensed rings
- C11B9/0049—Essential oils; Perfumes compounds containing condensed hydrocarbon rings containing only two condensed rings the condensed rings sharing two common C atoms
- C11B9/0053—Essential oils; Perfumes compounds containing condensed hydrocarbon rings containing only two condensed rings the condensed rings sharing two common C atoms both rings being six-membered
-
- C—CHEMISTRY; METALLURGY
- C11—ANIMAL OR VEGETABLE OILS, FATS, FATTY SUBSTANCES OR WAXES; FATTY ACIDS THEREFROM; DETERGENTS; CANDLES
- C11B—PRODUCING, e.g. BY PRESSING RAW MATERIALS OR BY EXTRACTION FROM WASTE MATERIALS, REFINING OR PRESERVING FATS, FATTY SUBSTANCES, e.g. LANOLIN, FATTY OILS OR WAXES; ESSENTIAL OILS; PERFUMES
- C11B9/00—Essential oils; Perfumes
- C11B9/0061—Essential oils; Perfumes compounds containing a six-membered aromatic ring not condensed with another ring
-
- C—CHEMISTRY; METALLURGY
- C11—ANIMAL OR VEGETABLE OILS, FATS, FATTY SUBSTANCES OR WAXES; FATTY ACIDS THEREFROM; DETERGENTS; CANDLES
- C11B—PRODUCING, e.g. BY PRESSING RAW MATERIALS OR BY EXTRACTION FROM WASTE MATERIALS, REFINING OR PRESERVING FATS, FATTY SUBSTANCES, e.g. LANOLIN, FATTY OILS OR WAXES; ESSENTIAL OILS; PERFUMES
- C11B9/00—Essential oils; Perfumes
- C11B9/0069—Heterocyclic compounds
- C11B9/0073—Heterocyclic compounds containing only O or S as heteroatoms
- C11B9/0076—Heterocyclic compounds containing only O or S as heteroatoms the hetero rings containing less than six atoms
-
- C—CHEMISTRY; METALLURGY
- C11—ANIMAL OR VEGETABLE OILS, FATS, FATTY SUBSTANCES OR WAXES; FATTY ACIDS THEREFROM; DETERGENTS; CANDLES
- C11D—DETERGENT COMPOSITIONS; USE OF SINGLE SUBSTANCES AS DETERGENTS; SOAP OR SOAP-MAKING; RESIN SOAPS; RECOVERY OF GLYCEROL
- C11D3/00—Other compounding ingredients of detergent compositions covered in group C11D1/00
- C11D3/50—Perfumes
- C11D3/502—Protected perfumes
- C11D3/507—Compounds releasing perfumes by thermal or chemical activation
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Life Sciences & Earth Sciences (AREA)
- Engineering & Computer Science (AREA)
- Oil, Petroleum & Natural Gas (AREA)
- Wood Science & Technology (AREA)
- General Chemical & Material Sciences (AREA)
- Fats And Perfumes (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Heterocyclic Compounds That Contain Two Or More Ring Oxygen Atoms (AREA)
- Cosmetics (AREA)
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| GB201021864 | 2010-12-23 | ||
| GBGB1021864.2A GB201021864D0 (en) | 2010-12-23 | 2010-12-23 | Organic compounds |
| PCT/EP2011/074003 WO2012085287A1 (en) | 2010-12-23 | 2011-12-23 | Compounds capable of releasing fragrant compounds |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| ES2692179T3 true ES2692179T3 (es) | 2018-11-30 |
Family
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Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| ES11805863.5T Active ES2692179T3 (es) | 2010-12-23 | 2011-12-23 | Compuestos capaces de liberar compuestos fragantes |
Country Status (10)
| Country | Link |
|---|---|
| US (1) | US9193935B2 (enExample) |
| EP (1) | EP2655307B1 (enExample) |
| JP (1) | JP6232289B2 (enExample) |
| CN (1) | CN103261139B (enExample) |
| BR (1) | BR112013016191B1 (enExample) |
| ES (1) | ES2692179T3 (enExample) |
| GB (1) | GB201021864D0 (enExample) |
| MX (1) | MX341306B (enExample) |
| SG (1) | SG190848A1 (enExample) |
| WO (1) | WO2012085287A1 (enExample) |
Families Citing this family (20)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO2014180782A1 (en) * | 2013-05-08 | 2014-11-13 | Firmenich Sa | Pro-fragrance compounds |
| WO2014180791A1 (en) * | 2013-05-08 | 2014-11-13 | Firmenich Sa | Pro-fragrance compounds |
| EP3218458B1 (en) * | 2014-11-10 | 2019-01-02 | Givaudan S.A. | Improvments in or relating to organic compounds |
| WO2016074698A1 (en) | 2014-11-10 | 2016-05-19 | Givaudan Sa | Improvements in or relating to organic compounds |
| KR101609323B1 (ko) | 2015-03-06 | 2016-04-05 | 충북대학교 산학협력단 | 2-메톡시-4-(3-(4-메톡시페닐)프로필-1-엔-1-일)페놀 및 이의 제조방법 |
| GB201703706D0 (en) * | 2017-03-08 | 2017-04-19 | Givaudan Sa | Improvements in or relating to organic compounds |
| EP3533786A1 (en) | 2018-03-02 | 2019-09-04 | Givaudan SA | Thioether precursors for fragrant ketones and aldehydes |
| CN111936457B (zh) | 2018-06-22 | 2025-02-25 | 弗门尼舍有限公司 | 烯醇醚香料前体 |
| GB201817785D0 (en) | 2018-10-31 | 2018-12-19 | Givaudan Sa | Organic compounds |
| CN113195697A (zh) * | 2018-12-17 | 2021-07-30 | 奇华顿股份有限公司 | 加香方法 |
| EP3898912A1 (en) | 2018-12-17 | 2021-10-27 | Givaudan SA | A method of countering malodour in a washing machine comprising the addition of a fragrance precursor |
| CN112752744B (zh) * | 2018-12-20 | 2025-02-18 | 弗门尼舍有限公司 | 烷基烯醇醚香料前体 |
| EP4007748A1 (en) | 2019-12-03 | 2022-06-08 | Firmenich SA | Enol ether properfume |
| WO2022018054A1 (en) * | 2020-07-24 | 2022-01-27 | Firmenich Sa | Process for preparing indene acryladehyde derivatives |
| WO2022261956A1 (en) | 2021-06-18 | 2022-12-22 | Givaudan Sa | Fragrance compounds |
| WO2023065200A1 (en) | 2021-10-21 | 2023-04-27 | Givaudan Sa | Organic compounds |
| WO2023065203A1 (en) | 2021-10-21 | 2023-04-27 | Givaudan Sa | Organic compounds |
| WO2024200404A1 (en) | 2023-03-30 | 2024-10-03 | Givaudan Sa | Unsaturated ether fragrance precursors |
| WO2025003204A1 (en) | 2023-06-27 | 2025-01-02 | Givaudan Sa | Organic compounds and their use for generating a fragrant alcohol |
| GB202405427D0 (en) | 2024-04-18 | 2024-06-05 | Givaudan Sa | Process |
Family Cites Families (12)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3115530A (en) | 1960-05-13 | 1963-12-24 | Exxon Research Engineering Co | Preferred alkyl aryl sulfonate detergents |
| CH411836A (de) | 1961-09-07 | 1966-04-30 | Basf Ag | Verfahren zur Herstellung von Mischoligomeren aus 1,3-Dienen und Verbindungen mit aktivierter olefinischer Doppelbindung |
| US3196174A (en) | 1962-03-01 | 1965-07-20 | Exxon Research Engineering Co | Perhydro bis-(isoprenyl) alkyl aryl sulfonates |
| DE2301438A1 (de) | 1973-01-12 | 1974-07-25 | Hoechst Ag | Verwendung von butadienderivaten als optische aufheller fuer waschmittel |
| FR2729661B1 (fr) * | 1995-01-19 | 1997-04-04 | Mane Fils V | Procede de preparation de substances aromatiques par voie biochimique |
| JP3792450B2 (ja) | 1999-09-03 | 2006-07-05 | 花王株式会社 | 機能性物質放出体 |
| JP3840868B2 (ja) | 2000-02-22 | 2006-11-01 | 株式会社ツムラ | 新規な補骨脂の使用方法 |
| EP1262473A1 (en) * | 2001-05-30 | 2002-12-04 | Givaudan SA | Precursors for fragrant ketones and fragrant aldehydes |
| JP2008303159A (ja) * | 2007-06-06 | 2008-12-18 | Osaka Prefecture Univ | カルボニル化合物の製造方法 |
| GB0717485D0 (en) | 2007-09-08 | 2007-10-17 | Unilever Plc | Improvements relating to fabric conditioners |
| JP2012502092A (ja) * | 2008-09-12 | 2012-01-26 | フイルメニツヒ ソシエテ アノニム | 活性アルデヒドおよびケトンを放出できるジビニルエーテル誘導体および芳香表面への使用方法 |
| US8669385B2 (en) * | 2009-10-13 | 2014-03-11 | University Of Central Florida Research Foundation, Inc. | Oxidative cleavage of unsaturated carboxylic acids |
-
2010
- 2010-12-23 GB GBGB1021864.2A patent/GB201021864D0/en not_active Ceased
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2011
- 2011-12-23 BR BR112013016191-4A patent/BR112013016191B1/pt active IP Right Grant
- 2011-12-23 SG SG2013039052A patent/SG190848A1/en unknown
- 2011-12-23 US US13/996,158 patent/US9193935B2/en active Active
- 2011-12-23 MX MX2013006034A patent/MX341306B/es active IP Right Grant
- 2011-12-23 WO PCT/EP2011/074003 patent/WO2012085287A1/en not_active Ceased
- 2011-12-23 CN CN201180061738.3A patent/CN103261139B/zh active Active
- 2011-12-23 ES ES11805863.5T patent/ES2692179T3/es active Active
- 2011-12-23 EP EP11805863.5A patent/EP2655307B1/en active Active
- 2011-12-23 JP JP2013545436A patent/JP6232289B2/ja active Active
Also Published As
| Publication number | Publication date |
|---|---|
| MX341306B (es) | 2016-08-15 |
| BR112013016191B1 (pt) | 2021-02-09 |
| SG190848A1 (en) | 2013-07-31 |
| JP6232289B2 (ja) | 2017-11-15 |
| MX2013006034A (es) | 2013-07-03 |
| BR112013016191A2 (pt) | 2020-08-04 |
| US20130316938A1 (en) | 2013-11-28 |
| US9193935B2 (en) | 2015-11-24 |
| GB201021864D0 (en) | 2011-02-02 |
| CN103261139B (zh) | 2015-09-23 |
| WO2012085287A1 (en) | 2012-06-28 |
| EP2655307A1 (en) | 2013-10-30 |
| EP2655307B1 (en) | 2018-08-01 |
| CN103261139A (zh) | 2013-08-21 |
| JP2014508121A (ja) | 2014-04-03 |
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