(WO2019185910) NOVEL USE OF SUBSTITUTED 2H-CHROMENS AND THEIR DERIVATIVES 机翻标题: 暂无翻译,请尝试点击翻译按钮。

源语言标题
(WO2019185910) NOVEL USE OF SUBSTITUTED 2H-CHROMENS AND THEIR DERIVATIVES
公开号/公开日
WO2019/185910 WO2019/185910 / 2020-01-30 2019-10-03
申请号/申请日
WOEP2019/058081 / 2019-03-29
发明人
CLASADONTE LAUREDUESTERLOH ANDRÉINDRASENA WEERASINGHENETSCHER THOMASSTEMMLER RENÉWERHLI CHISTOF;
申请人
DSM;
主分类号
IPC分类号
C11B-005/00
摘要
(WO2019/185910) The present invention is directed towards the use of 2H-chromens and their derivatives of formula (I) and/or of formula (II) wherein R1 and R2 are independently from each other H or CM1-11 -alkyl or (CH2)n— OH with n being an integer from 1 to 6 or R1 and R2 together represent a keto group, and wherein R3, R4, R5, and R6 are independently from each other H or C1-6-alkyl or C1-6-alkoxy, and R7 is H or C1-6-alkyl, as antioxidants in PUFA-containing edible oils such as marine oil, microbial oil, fungal oil, algal oil and PUFA-containing plant oil for human consumption. The present invention is further directed towards these PUFA- containing edible oils comprising at least one compound of formula (I) and/or at least one compound of formula (II). The present invention is further directed to a method of preserving the shelf life of PUFAs and/or their esters in an edible oil comprising the step of adding at least one compound of formula (I) and/or at least one compound of formula (II) to said edible oil, as well as to a method of limiting the amount of oxidation of PUFAs and/or their esters in an edible oil which is exposed to air, comprising adding at least one compound of formula (I) and/or at least one compound of formula (II) to said edible oil, preferably in an amount of said compound of formula (I) and/or said compound of formula (II) ranging from 10 to 500 ppm, preferably ranging from 30 to 300 ppm, more preferably ranging from 100 to 250 ppm, based on the total amount of said edible oil.
机翻摘要
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地址
代理人
(WO2019185910) STECK, Melanie ([CH])
代理机构
;
优先权号
2018EP-0165030
主权利要求
(WO2019/185910) 1. Claims 1 . Use of a compound of formula (I) and/or a compound of formula (II) as antioxidant in oil,   wherein the oil contains polyunsaturated fatty acids and/or their esters, and wherein the oil is for human consumption, and   wherein R1and R2are independently from each other H or CM1 -alkyl or (CH2)n— OH with n being an integer from 1 to 6 or R1and R2together represent a keto group, and wherein   R3, R4, R5, and R6are independently from each other H or Ci-6-alkyl or Ci-6-alkoxy, and   R7is H or Ci-6-alkyl. 2. The use according to claim 1 , whereby in compound of formula (I) and/or in compound of formula (II) R1and R2are independently from each other H or Ci-4-alkyl or (CH2)n— OH with n being an integer from 1 to 4, R3, R4, R6and R7are independently from each other H or Ci-4- alkyl, and R5is H or Ci-4-alkyl or Ci-4-alkoxy. 3. The use according to claim 1 or 2, whereby in compound of formula (I) and/or in compound of formula (II) R1and R2are independently from each other H or Ci-2-alkyl or (CH2)n— OH with n being 1 or 2, R3, R4, R6and R7are independently from each other H or Ci-2-alkyl, and R5is H or Ci-2-alkyl or Ci-2-alkoxy. 4. The use according to one or more of the preceding claims, whereby in compound of formula (I) and/or in compound of formula (II) R1and R2are independently from each other H or methyl or (CH2)— OH, R3, R4, R6and R7are independently from each other H or methyl or ethyl, and R5is H or methyl or methoxy. 5. The use according to one or more of the preceding claims, whereby the compound of formulae (I) or (II) is one of the following compounds of formulae (1 ) to (7):   6. Oil containing polyunsaturated fatty acids (PUFAs) and/or their esters for human consumption comprising a compound of formula (I) and/or a compound of formula (II),   wherein R1and R2are independently from each other H or CM1 -alkyl or (CH2)n— OH with n being an integer from 1 to 6 or R1and R2together represent a keto group, and   wherein R3, R4, R5, and R6are independently from each other H or Ci-6-alkyl or Ci-6-alkoxy, and   R7is H or Ci-6-alkyl. 7. The oil containing polyunsaturated fatty acids (PUFAs) and/or their esters for human consumption according to claim 6, whereby the PUFA- containing oil is marine oil or microbial oil or fungal oil or algal oil or PUFA-containing plant oil, preferably whereby the PUFA-containing oil is marine oil or algal oil, more preferably whereby the PUFA-containing oil is algal oil. 8. The oil containing polyunsaturated fatty acids (PUFAs) and/or their esters for human consumption according to claim 6 and/or claim 7 additionally comprising esters of ascorbic acid with linear C12-20 alkanols, preferably esters of ascorbic acid with linear C14-18 alkanols, more preferably ascorbyl palmitate. 9. The oil containing polyunsaturated fatty acids (PUFAs) and/or their esters for human consumption according to any one or more of claims 6 to 8 additionally comprising alpha-tocopherol and/or gamma- tocopherol. 10. Marine oil for human consumption comprising at least one compound of formula (I) and/or at least one compound of formula (II),   wherein R1and R2are independently from each other H or CM1 -alkyl or (CH2)n— OH with n being an integer from 1 to 6 or R1and R2together represent a keto group, and   wherein R3, R4, R5, and R6are independently from each other H or Ci-6-alkyl or Ci-6-alkoxy, and   R7is H or Ci-6-alkyl.   11 . The marine oil according to claim 10 additionally comprising esters of ascorbic acid with linear C12-20 alkanols, preferably esters of ascorbic acid with linear C14-18 alkanols, more preferably ascorbyl palmitate. 12. The marine oil according to claim 10 and/or claim 1 1 additionally   comprising alpha-tocopherol and/or gamma-tocopherol. 13. Microbial oil for human consumption comprising a compound of formula  (I) and/or a compound of formula (II),   wherein R1and R2are independently from each other H or CM1 -alkyl or (CH2)n— OH with n being an integer from 1 to 6 or R1and R2together represent a keto group, and   wherein R3, R4, R5, and R6are independently from each other H or Ci- 6-alkyl or Ci-6-alkoxy, and   R7is H or Ci-6-alkyl. 14. The microbial oil according to claim 13 additionally comprising esters of ascorbic acid with linear C12-20 alkanols, preferably esters of ascorbic acid with linear C14-18 alkanols, more preferably ascorbyl palmitate. 15. The microbial oil according to claim 13 and/or claim 14 additionally comprising alpha-tocopherol and/or gamma-tocopherol. 16. Algal oil for human consumption comprising at least one compound of formula (I) and/or at least one compound of formula (II),   wherein R1and R2are independently from each other H or Ci-n-alkyl or (CH2)n— OH with n being an integer from 1 to 6 or R1and R2together represent a keto group, and   wherein R3, R4, R5, and R6are independently from each other H or Ci-6- alkyl or Ci-6-alkoxy, and   R7is H or Ci-6-alkyl. 17. The algal oil according to claim 16 additionally comprising esters of ascorbic acid with linear C12-20 alkanols, preferably esters of ascorbic acid with linear C14-18alkanols, more preferably ascorbyl palmitate. 18. The algal oil according to claim 16 and/or claim 17 additionally   comprising alpha-tocopherol and/or gamma-tocopherol. 19. 2,2,4,5,7,8-hexamethyl-2H-chromen-6-ol of formula (3).   20. A process for the manufacture of a mixture of compounds of formulae (3a) and (3b) comprising the following steps:   a) optional protection of the hydroxy group of compound of formula (I) to obtain the compound of formula (II), b) methyl-Grignard addition to the compound of formula (II) and water elimination to obtain a mixture of compounds of formulae (Ilia) and (I Mb); or methyl-Grignard addition to the compound of formula (I) and water elimination to obtain a mixture of compounds of formulae (3a) and (3b), respectively;   and   c) optional deprotection of the ether compounds of formulae (Ilia) and (lllb) to a mixture of compounds of formulae (3a) and (3b)   21 . 6-ethoxy-2,2,4-trimethyl-2H-chromene of formula (5) with Et being ethyl.   22. A process for the manufacture of compound of formula (5) with Et being ethyl comprising the following steps:   i) methyl-Grignard addition to compound of formula (IV) and water elimination to obtain the compound of formula (1 ),   ii) etherification of compound of formula (1 ) to obtain the compound of formula (5)   23. An edible oil comprising at least one compound of formula (I) and/or at least one compound of formula (II),   and PUFAs and/or their esters,   wherein R1and R2are independently from each other H or Ci-n-alkyl or (CH2)n— OH with n being an integer from 1 to 6 or R1and R2together represent a keto group, and   wherein R3, R4, R5, and R6are independently from each other H or Ci-6- alkyl or Ci-6-alkoxy, and   R7is H or Ci-6-alkyl. 24. The edible oil according to claim 23, whereby the edible oil is marine oil or microbial oil or fungal oil or algal oil or PUFA-containing plant oil, preferably whereby the edible oil is marine oil or algal oil, more preferably whereby the edible oil is algal oil. 25. A method of preserving the shelf life of PUFAs and/or their esters in an edible oil comprising the step of adding at least one compound of formula (I) and/or at least one compound of formula (II) to said edible oil,   wherein R1and R2are independently from each other H or Ci-n-alkyl or (CH2)n— OH with n being an integer from 1 to 6 or R1and R2together represent a keto group, and   wherein R3, R4, R5, and R6are independently from each other H or Ci-6- alkyl or Ci-6-alkoxy, and   R7is H or Ci-6-alkyl. 26. The method according to claim 25, wherein the compound of formula  (I) and/or the compound of formula (II) is/are added to said edible oil in an amount ranging from 10 to 500 ppm, preferably ranging from 30 to 300 ppm, more preferably ranging from 100 to 250 ppm, based on the total amount of said edible oil. 27. A method of limiting the amount of oxidation of PUFAs and/or their esters in an edible oil which is exposed to air, comprising adding at least one compound of formula (I) and/or at least one compound of formula (II) to said edible oil,   wherein R1and R2are independently from each other H or Ci-n-alkyl or (CH2)n— OH with n being an integer from 1 to 6 or R1and R2together represent a keto group, and   wherein R3, R4, R5, and R6are independently from each other H or Ci-6- alkyl or Ci-6-alkoxy, and   R7is H or Ci-6-alkyl. 28. The method according to claim 27, wherein the compound of formula (I) and/or the compound of formula (II) is/are added to said edible oil in an amount ranging from 10 to 500 ppm, preferably ranging from 30 to 300 ppm, more preferably ranging from 100 to 250 ppm, based on the total amount of said edible oil.
法律状态
PENDING
专利类型码
A3 A2
国别省市代码
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