CN110078645A - 羟基酪醇己二氨基甲酸酯及其合成方法和应用 - Google Patents
羟基酪醇己二氨基甲酸酯及其合成方法和应用 Download PDFInfo
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Abstract
本发明公开了结构式(I)所示的羟基酪醇己二氨基甲酸酯及其合成方法,该化合物以羟基酪醇和1,6‑己二异氰酸酯为原料,反应过程用N2保护,在催化剂作用下于有机溶剂中反应,反应结束后减压浓缩,粗品经柱层析分离纯化即可。本发明化合物可用于对食品的储藏保质,防止食品氧化变色,防止因氧化酸败而降低食品的风味和质量,同时可添加在保健品、化妆品中加强抗氧化性能。
Description
技术领域
本发明涉及羟基酪醇己二氨基甲酸酯及其合成方法,该化合物可应用于抗氧化剂、抗菌剂和紫外线吸收添加剂领域。
背景技术
油脂是日常消费和食品加工中的重要原料,气味芬芳,滋味可口,易消化吸收,广泛用在食品加工上,改善产品性质,赋予食品良好的风味和质地,几乎所有食品都含有油脂。大多植物油富含不饱和脂肪酸,经常食用富含不饱和脂肪酸的食品,可增强人体组织对氧的吸收能力,改善血液循环,保护血管壁,调节毛细血管的渗透作用,防止血栓形成,有助于预防动脉硬化和冠心病等。但是这类含油脂食品在贮运加工中,极易因空气,光线和热的影响发生氧化,品质恶化,并产生刺激性臭味。油脂氧化不仅降低油脂及含油食品的商品和食用价值,进入人体会对机体造成伤害,诱发各种病变。随着国内外对食品质量和安全的广泛关注,如何防止食品变质,保障人体健康日显重要.
为了提高食品的抗氧化性能,除了采用低温、避光、真空等物理方法外,主要依靠在食品中加入抗氧化剂,以防止食品,特别是含油脂食品的氧化酸败。目前,关于抗氧化剂的人工合成及半合成的相关研究越来越受到人们的重视,应用广泛。
发明人利用1,6-己二异氰酸酯对羟基酪醇进行结构改造,获得了一种新型羟基酪醇己二氨基甲酸酯,并对其进行初步的抗氧化实验验证了该化合物的抗氧化活性,可应用于食品、医药、保健品领域。
发明内容
本发明的目的之一是提供一种羟基酪醇己二氨基甲酸酯及其合成方法。
本发明的另一目的是提供上述化合物作为抗氧化添加剂、抗菌剂和紫外线吸收剂的应用,可广泛应用于医药、保健品、食品、化妆品领域。
本发明实现过程如下:
结构式(I)所示的羟基酪醇己二氨基甲酸酯,
上述化合物的制备方法:
以羟基酪醇和1,6-己二异氰酸酯为原料在催化剂作用下于有机溶剂中反应,反应过程采用氮气保护,反应结束后减压浓缩,粗品经柱层析分离纯化即可得羟基酪醇己二氨基甲酸酯。
为了实现上述合成路线,本发明的合成步骤如下:
(1)将一定量羟基酪醇和适量催化剂用有机溶剂溶解,置于反应器中,通入氮气保护,加入1,6-己二异氰酸酯于反应体系中,加热至60℃~108℃,反应6~10小时;
(2)薄层色谱法跟踪反应至完全,停止加热,撤去保护装置,将反应混合体系减压浓缩后,得羟基酪醇己二氨基甲酸酯粗品;
(3)将羟基酪醇己二氨基甲酸酯粗品用甲苯溶解,用硅胶柱进行吸附分离纯化,采用石油醚/乙酸乙酯混合溶剂作为洗脱剂洗脱富集,将洗脱液减压浓缩干燥后即得羟基酪醇己二氨基甲酸酯精品。
上述步骤(1)中的有机溶剂优选甲苯、DMF或乙腈,进一步优选为甲苯。
上述步骤(1)中的羟基酪醇和1,6-己二异氰酸酯的摩尔比优选为2.5:1~3:1,进一步优选为3:1。
上述步骤(1)中的催化剂优选三乙胺或DMAP等,进一步优选为DMAP。
上述步骤(1)中的反应温度优选为108℃。
上述步骤(1)中的反应时间优选为8小时。
上述步骤(3)中的洗脱剂优选为石油醚:乙酸乙酯=1:5。
本发明制备方法简单,制备得到的羟基酪醇己二氨基甲酸酯可用于对食品的储藏保质,防止食品氧化变色,防止因氧化酸败而降低食品的风味和质量,同时还可添加在保健品、化妆品中加强抗氧化性能。本发明所述化合物还可作为抗菌剂或紫外线吸收剂应用于食品、医药、保健品领域和涂料领域。
附图说明
图1 为DPPH自由基清除实验结果。
具体实施方式
下面结合具体实施例对本发明作进一步阐述。这些实施例仅是出于解释说明的目的,而不限制本发明的范围和实质。
实施例1
将139mg (0.90mmol) 羟基酪醇与3.7mg (0.03mmol) DMAP置于100mL反应器中,加入50mL甲苯充分溶解后,通入氮气保护。将50mg (0.30mmol) 1,6-己二异氰酸酯溶解于5mL甲苯中,用分液漏斗缓慢地滴加到反应液中,滴加完毕后在108℃下回流8h。薄层色谱法跟踪反应至完全,停止加热,撤去保护装置。将反应混合体系减压浓缩后得羟基酪醇己二氨基甲酸酯粗品。利用硅胶柱层析对粗品进一步分离纯化,石油醚:乙酸乙酯=1:5作为洗脱剂,将洗脱液减压浓缩干燥即得羟基酪醇己二氨基甲酸酯粗品精品62.26mg,总收率为43.55%。
1H-NMR (400MHz, DMSO-d 6) δ (ppm): 8.43 (2H, s), 6.90 (2H, s), 6.86~6.71 (4H, m), 5.79 (4H, s), 4.72 (4H, m), 3.35 (4H, m), 2.90 (4H, m), 1.58(4H, m), 1.29 (4H, m); 13C-NMR (75MHz, DMSO-d 6) δ (ppm): 158.6, 148.9, 145.0,136.7, 122.6, 119.5, 117.3, 64.1, 45.7, 36.3, 28.8; MS (ESI) for (M+H)+:477.5。
实施例2
将139mg (0.90mmol) 羟基酪醇与42μL (0.30mmol) 三乙胺置于100mL反应器中,加入50mL甲苯充分溶解后,通入氮气保护。将50mg (0.30mmol) 1,6-己二异氰酸酯溶解于5mL甲苯中,用分液漏斗缓慢地滴加到反应液中,滴加完毕后在108℃下回流6h。薄层色谱法跟踪反应至完全,停止加热,撤去保护装置。将反应混合体系减压浓缩后得羟基酪醇己二氨基甲酸酯粗品。利用硅胶柱层析对粗品进一步分离纯化,石油醚:乙酸乙酯=1:5作为洗脱剂,将洗脱液减压浓缩干燥即得羟基酪醇己二氨基甲酸酯粗品精品53.18mg,总收率为37.20%。
实施例3
将116mg (0.75mmol) 羟基酪醇与3.7mg (0.03mmol) DMAP置于100mL反应器中,加入50mL甲苯充分溶解后,通入氮气保护。将50mg (0.30mmol) 1,6-己二异氰酸酯溶解于5mL甲苯中,用分液漏斗缓慢地滴加到反应液中,滴加完毕后在60℃下回流8h。薄层色谱法跟踪反应至完全,停止加热,撤去保护装置。将反应混合体系减压浓缩后得羟基酪醇己二氨基甲酸酯粗品。利用硅胶柱层析对粗品进一步分离纯化,石油醚:乙酸乙酯=1:5作为洗脱剂,将洗脱液减压浓缩干燥即得羟基酪醇己二氨基甲酸酯粗品精品56.47mg,总收率为39.50%。
实施例4
将116mg (0.75mmol) 羟基酪醇与3.7mg (0.03mmol) DMAP置于100mL反应器中,加入50mL甲苯充分溶解后,通入氮气保护。将50mg (0.30mmol) 1,6-己二异氰酸酯溶解于5mL甲苯中,用分液漏斗缓慢地滴加到反应液中,滴加完毕后在80℃下回流10h。薄层色谱法跟踪反应至完全,停止加热,撤去保护装置。将反应混合体系减压浓缩后得羟基酪醇己二氨基甲酸酯粗品。利用硅胶柱层析对粗品进一步分离纯化,石油醚:乙酸乙酯=1:5作为洗脱剂,将洗脱液减压浓缩干燥即得羟基酪醇己二氨基甲酸酯粗品精品44.29mg,总收率为30.98%。
实施例5
将139mg (0.90mmol) 羟基酪醇与3.7mg (0.03mmol) DMAP置于100mL反应器中,加入50mL甲苯充分溶解后,通入氮气保护。将50mg (0.30mmol) 1,6-己二异氰酸酯溶解于5mL甲苯中,用分液漏斗缓慢地滴加到反应液中,滴加完毕后在80℃下回流8h。薄层色谱法跟踪反应至完全,停止加热,撤去保护装置。将反应混合体系减压浓缩后得羟基酪醇己二氨基甲酸酯粗品。利用硅胶柱层析对粗品进一步分离纯化,石油醚:乙酸乙酯=1:5作为洗脱剂,将洗脱液减压浓缩干燥即得羟基酪醇己二氨基甲酸酯粗品精品57.41mg,总收率为40.16%。
实施例6
将139mg (0.90mmol) 羟基酪醇与42μL (0.30mmol) 三乙胺置于100mL反应器中,加入50mL甲苯充分溶解后,通入氮气保护。将50mg (0.30mmol) 1,6-己二异氰酸酯溶解于5mL甲苯中,用分液漏斗缓慢地滴加到反应液中,滴加完毕后在60℃下回流8h。薄层色谱法跟踪反应至完全,停止加热,撤去保护装置。将反应混合体系减压浓缩后得羟基酪醇己二氨基甲酸酯粗品。利用硅胶柱层析对粗品进一步分离纯化,石油醚:乙酸乙酯=1:5作为洗脱剂,将洗脱液减压浓缩干燥即得羟基酪醇己二氨基甲酸酯粗品精品50.38mg,总收率为35.24%。
实施例7
将116mg (0.75mmol) 羟基酪醇与42μL (0.30mmol) 三乙胺置于100mL反应器中,加入50mL甲苯充分溶解后,通入氮气保护。将50mg (0.30mmol) 1,6-己二异氰酸酯溶解于5mL甲苯中,用分液漏斗缓慢地滴加到反应液中,滴加完毕后在108℃下回流6h。薄层色谱法跟踪反应至完全,停止加热,撤去保护装置。将反应混合体系减压浓缩后得羟基酪醇己二氨基甲酸酯粗品。利用硅胶柱层析对粗品进一步分离纯化,石油醚:乙酸乙酯=1:5作为洗脱剂,将洗脱液减压浓缩干燥即得羟基酪醇己二氨基甲酸酯粗品精品41.55mg,总收率为29.08%。
实施例8
将139mg (0.90mmol) 羟基酪醇与3.7mg (0.03mmol) DMAP置于100mL反应器中,加入50mL甲苯充分溶解后,通入氮气保护。将50mg (0.30mmol) 1,6-己二异氰酸酯溶解于5mL甲苯中,用分液漏斗缓慢地滴加到反应液中,滴加完毕后在108℃下回流10h。薄层色谱法跟踪反应至完全,停止加热,撤去保护装置。将反应混合体系减压浓缩后得羟基酪醇己二氨基甲酸酯粗品。利用硅胶柱层析对粗品进一步分离纯化,石油醚:乙酸乙酯=1:5作为洗脱剂,将洗脱液减压浓缩干燥即得羟基酪醇己二氨基甲酸酯粗品精品52.72mg,总收率为36.88%。
实施例9 DPPH自由基清除实验
DPPH是一种比较稳定的脂性自由基,其N上有一个游离电子,其甲苯溶液呈紫色,在517nm处有最大的吸收峰。加入抗氧化剂以后,DPPH捕捉一个电子与游离电子配对,紫色褪去,变为无色物质,在517nm处的吸收消失,其褪色程度与其接受的电子数成定量关系。依此原理用分光光度计检测DPPH自由基与试样液反应后吸光值的变化,可检定试样提供氢原子、清除自由基抗氧化的能力。实验表明,该法简便易行,灵敏可靠。
实验方法:
(a)DPPH测试液的配制:精确称取一定量的1,1-二苯基-2-苦基肼自由基,用甲苯溶解为2×10-4 mol/L的DPPH溶液,避光冷藏放置。
(b)待测液的配制:Vc(阳性对照)、羟基酪醇己二氨基甲酸酯(样品)和羟基酪醇(对照品)。用甲苯将样品液进行梯度稀释,同时采用一定量的甲苯将2组对照分别溶解于试管中,制成与样品相同的浓度梯度。得到相应的2组对照溶液(梯度设置见表1)。
(c)操作方法:
样品液吸光度测定:取样品液 (表1A) 2mL,加入浓度为2×10-4 mol/L的DPPH溶液2mL,混匀后在室温下避光反应30min,以甲苯调零,在517nm处测定其吸光度Ai,同时测定2mL甲苯与2mL样品溶液混合后的吸光度Aj以及2mL DPPH溶液与2mL甲苯混合后的吸光度Ao(实验结果见表2)。
对照品吸光度测定:取(b)步骤对照品溶液(表1 Vc、B)2mL,加入浓度为2×10- 4mol/L的DPPH溶液2mL,混匀后在室温下避光反应30min,以甲苯调零,在517nm处测定其吸光度Ai,同时测定2mL甲苯与2mL对照品溶液混合后的吸光度Aj以及2mL DPPH溶液与2mL甲苯混合后的吸光度Ao(实验结果见表2)。
(d)清除率的计算:清除率(%)=[1-(Ai-Aj)/Ao]×100%
根据表1~3与图1实验结果可知,羟基酪醇己二氨基甲酸酯(A)以浓度依赖性方式表现出对DPPH明显的清除作用。其对DPPH的清除率从19.87%(1.76 ppm)到97.14%(915.20ppm),与单一的羟基酪醇(B)相比,同等浓度下羟基酪醇己二氨基甲酸酯(A)清除DPPH自由基的能力明显更好。同时,与阳性对照Vc相比,羟基酪醇己二氨基甲酸酯(A)的清除能力接近。以上实验结果证明该化合物具有优良的抗氧化活性,可以作为一种新型的抗氧化添加剂应用于食品、医药、保健品、化妆品领域。
Claims (10)
1.结构式(I)所示的羟基酪醇己二氨基甲酸酯,
。
2.权利要求1所述化合物的制备方法,其特征在于:
以羟基酪醇和1,6-己二异氰酸酯为原料在催化剂作用下于有机溶剂中反应,反应过程采用氮气保护,反应结束后减压浓缩,粗品经柱层析分离纯化即可得羟基酪醇己二氨基甲酸酯。
3.根据权利要求2所述的制备方法,其特征在于包括以下步骤:
(1)将一定量羟基酪醇和适量催化剂用有机溶剂溶解,置于反应器中,通入氮气保护,加入1,6-己二异氰酸酯于反应体系中,加热至60℃~108℃,反应6~10小时;
(2)薄层色谱法跟踪反应至完全,停止加热,撤去保护装置,将反应混合体系减压浓缩后,得羟基酪醇己二氨基甲酸酯衍生物粗品;
(3)将羟基酪醇己二氨基甲酸酯衍生物粗品用甲苯溶解,用硅胶柱进行吸附分离纯化,采用石油醚/乙酸乙酯混合溶剂作为洗脱剂洗脱富集,将洗脱液减压浓缩干燥后即得羟基酪醇己二氨基甲酸酯精品。
4.根据权利要求3所述的制备方法,其特征在于:上述步骤(1)中,有机溶剂选自甲苯、DMF或乙腈,进一步优选为甲苯。
5.根据权利要求3所述的制备方法,其特征在于:上述步骤(1)中,羟基酪醇和1,6-己二异氰酸酯的摩尔比为2.5:1~3:1,进一步优选为3:1。
6.根据权利要求3所述的制备方法,其特征在于:上述步骤(1)中,催化剂选自三乙胺或DMAP,进一步优选为DMAP。
7.根据权利要求3所述的制备方法,其特征在于:上述步骤(3)中,洗脱剂石油醚和乙酸乙酯的体积比1:5。
8.权利要求1所示化合物作为抗氧化添加剂的应用。
9.权利要求1所示化合物作为抗菌剂的应用。
10.权利要求1所示化合物作为紫外线吸收剂的应用。
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