CN110940654B - 一种柠檬醛的检测方法 - Google Patents
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Abstract
本发明涉及一种柠檬醛的检测方法,用具有如式Ⅰ所示结构的化合物作为的荧光显色剂,采用荧光发射光谱法检测荧光强度。本发明的柠檬醛的检测方法方便易行,灵敏度高,抗干扰性强,检测速度快,扩充了柠檬醛含量的检测方式。
Description
技术领域
本发明涉及一种利用荧光显色检测柠檬醛的方法,属于检测技术领域。
背景技术
柠檬醛广泛地应用于食品、日用化学品等领域,例如香水、巧克力、冷饮、奶制品、烟草和糖果等。柠檬醛是一种增香剂同时具有一定抗菌性能,可应用到食品中,但需适度添加。柠檬醛作为日用化学品,易造成使用者皮肤过敏。《欧盟玩具安全新指令》(2009/48/EC)将柠檬醛列为55种禁用致敏性香味剂中的一种。在研究领域,由于柠檬醛能抑制细胞增殖增长,从而被广泛地用于医药领域,例如孙忠良等人研究的《柠檬醛对阿糖胞苷抗白血病细胞HL-60强效增敏作用》。由于柠檬醛在不同领域有不同使用要求,需要在检测技术上对柠檬醛有更精准的测定。
已有检测柠檬醛浓度的方法主要液相色谱法和气相色谱法。GB/T 24800.9-2009《化妆品中柠檬醛、肉桂醇、茴香醇、肉桂醛和香豆素的测定 气相色谱法》中对柠檬醛的检出限为3mg/kg,定量限为10mg/kg。而柠檬醛在某些食品中的限量,低于该限值,例如柠檬醛在胶姆糖中限量为1.70mg/kg、软饮料中限量为9.2mg/kg,都超出了普通气相色谱法的检测定量限。
此外柠檬醛有两种异构体,分别为香叶醛和橙花醛。因此在色谱检测中需要分别对两种标品进行分离并测定,才能得到精准结果,测试条件相对于纯物质检测较苛刻。席海为等人的《高效液相色谱法对化妆品中17种致敏原的同时测定》中对柠檬醛的检测利用一项色谱法,发现柠檬醛在普通C18柱上的出峰不明显。
发明内容
本发明要解决的技术问题是提供一种方便易行,灵敏度高,抗干扰性强,检测速度快的柠檬醛的检测方法。
本发明为解决上述技术问题提出的一种技术方案是:一种柠檬醛的检测方法,用具有如式Ⅰ所示结构的化合物作为柠檬醛的荧光显色剂,
上述柠檬醛的检测方法具体步骤是:将所述荧光显色剂制成浓度为1×10-5mol/L~1×10-3mol/L的甲醇溶液,将待测物加入荧光显色剂的甲醇溶液中,采用荧光发射光谱法检测荧光强度,荧光强度与柠檬醛含量呈正比,根据荧光强度判断待测物中的柠檬醛含量。
上述柠檬醛的检测方法先用所述荧光显色剂的甲醇溶液检测不同浓度的柠檬醛标准品,绘制标准品的含量曲线,再用荧光显色剂的甲醇溶液检测待测物,采用标准曲线法计算待测物中的柠檬醛含量。
上述荧光显色剂的甲醇溶液中荧光显色剂的浓度为1×10-5mol/L~1×10-3mol/L。
上述荧光发射光谱法检测荧光显色剂的荧光强度在327nm激发,发射峰波长为403nm。
上述荧光发射光谱法检测柠檬醛的荧光强度在378nm激发,在548nm测定。
上述荧光显色剂的制备方法是将如式Ⅱ所示结构的化合物溶解于有机溶剂中,然后加入水合联胺和催化剂,反应生成如式Ⅰ所示结构的化合物,反应式如下:
上述反应时间为30min~2h,反应温度为5℃~37℃。
上述催化剂是Pd/C,所述有机溶剂是甲醇或乙醇。
上述如式Ⅱ所示结构的化合物与水合联胺的摩尔比为1:0.1至1:3,所述催化剂与如式Ⅱ所示结构的化合物的摩尔比为1:1~1:30。
本发明具有积极的效果:
(1)本发明合成了一种新型的柠檬醛荧光显色剂,其具体原理是:化合物Ⅱ几乎无荧光特性,对化合物Ⅱ氨基化,由于氨基的给电子性,B元素吸电子性,以及结构中的共轭属性,增强了结构中的p-π共轭,从而增强荧光,使得产物I有较强荧光性。荧光显色剂可在327nm激发,发射峰在403nm。
(2)本发明的柠檬醛的检测方法采用新型的荧光显色剂,与柠檬醛相互作用时会发生荧光显色现象,具体原理是伯胺基与柠檬醛相互作用,形成叔胺,导致原共轭轨道变化,在光作用下,电子跃迁到LUMO轨道,返回HOMO轨道时产生荧光,荧光随着加入的柠檬醛量增多而呈线性变化。达到检测柠檬醛的目的。与柠檬醛形成荧光缔合物,可以采用378nm激发,其发射峰在548nm。本发明的柠檬醛的检测方法中的荧光显色剂能对柠檬醛两种异构体都发生荧光显色作用,可以用荧光发射光谱计进行柠檬醛检测,扩充了目前对柠檬醛检测的方式。
(3)本发明的柠檬醛检测方法只需要按照一定浓度将荧光剂配成甲醇溶液,浓度优选1×10-5mol/L~1×10-3mol/L,可以采用荧发射光谱法进行检测荧光强度,采用标准曲线法用标准品绘制含量,从而进行具体含量的计算。该方法方便易行,灵敏度高,抗干扰性强,可以快速检测待测物中的柠檬醛含量。
附图说明
图1为实施例1的荧光显色剂的红外光谱图;
图2为实施例1的化合物Ⅱ、荧光显色剂Ⅰ和荧光显色剂Ⅰ与柠檬醛缔合物的荧光发射光谱图;
图3为采用实施例1的荧光显色剂检测不同浓度的柠檬醛的荧光发射光谱。
具体实施方式
实施例1
本实施例的荧光显色剂的分子结构如式Ⅰ所示:
该化合物的红外光谱图如图1所示。
本实施例的荧光显色剂的制备方法是将100mg(0.22mmol)的如式Ⅱ所示结构的化合物溶解于60mL的甲醇中,通氮气10min,依次加入150mg的水合联胺,23mg的钯炭催化剂Pd/C混合物,室温搅拌50min。过滤去除Pd/C混合物。产物进行旋蒸,得到粉红色固体,反应式如下:
反应完成后,用30mL的甲醇萃取4次,将有机相真空干燥。测得产率为70%。
其中,如式Ⅱ所示结构的化合物为外购试剂,其合成路线为现有技术,如式Ⅲ所示结构的对硝基苯甲醛、如式Ⅳ所示结构的5-溴-3-甲基吡咯烷、三氟乙酸、二氯甲烷、2,3-二氯-5,6-二氰对苯醌、三乙胺、三氟化硼乙醚混合反应生成化合物Ⅱ,反应式如下:
化合物Ⅱ几乎无荧光特性。荧光显色剂Ⅰ采用荧光发射光谱法荧光强度在327nm激发,发射峰波长为403nm。荧光显色剂Ⅰ与柠檬醛缔合物采用荧光发射光谱法荧光强度在378nm激发,在548nm测定。如图2所示,图中没有显示峰的是化合物Ⅱ,峰在403nm位置的是荧光显色剂Ⅰ,峰在548nm的是荧光显色剂Ⅰ与柠檬醛缔合物。
实施例2
本实施例的荧光显色剂的制备方法是将80mg(0.22mmol)的如式Ⅱ所示结构的化合物溶解于50mL的乙醇中,通氮气10min,依次加入120mg的水合联胺,20mg的钯炭催化剂Pd/C混合物,室温搅拌50min。过滤去除Pd/C混合物。产物进行旋蒸,得到粉红色固体。反应完成后,用30mL的甲醇萃取4次,将有机相真空干燥。测得产率为65%。
实施例3
本实施例的荧光显色剂的制备方法是将120mg(0.22mmol)的如式Ⅱ所示结构的化合物溶解于50mL的乙醇中,通氮气10min,依次加入120mg的水合联胺,10mg的钯炭催化剂Pd/C混合物,室温搅拌50min。过滤去除Pd/C混合物。产物进行旋蒸,得到粉红色固体。产物进行旋蒸,得到粉红色固体。反应完成后,用30mL的甲醇萃取4次,将有机相真空干燥。测得产率为68%。
应用例
本应用例的柠檬醛的检测方法是,采用实施例1合成的荧光显色剂Ⅰ,配制成甲醇溶液,荧光显色剂的浓度为0.2×10-3mol/L。加入标准浓度柠檬醛,在548nm测定发射峰强度。
然后制作标准曲线,浓度梯度设置,见表1。得到的荧光发射光谱图,如图3所示。
表1 荧光吸收曲线标准浓度设置表
管号 | 1 | 2 | 3 | 4 | 5 | 6 |
柠檬醛含量(µg/mL) | 0.0000 | 0.090 | 0.153 | 0.337 | 0.743 | 0.930 |
吸收值 | 0.0720 | 0.4020 | 0.4500 | 0.8280 | 1.3560 | 1.9890 |
得到标准曲线为y=1.9415x+0.1146, R值为0.9913,线性关系良好。由此可知,荧光强度与柠檬醛含量成线性正比。
本发明中所用试剂如无特殊说明均为外购试剂,浓度均为化学纯。
显然,上述实施例仅仅是为清楚地说明本发明所作的举例,而并非是对本发明的实施方式的限定。对于所属领域的普通技术人员来说,在上述说明的基础上还可以做出其它不同形式的变化或变动。这里无需也无法对所有的实施方式予以穷举。而这些属于本发明的精神所引伸出的显而易见的变化或变动仍处于本发明的保护范围之中。
Claims (9)
2.根据权利要求1所述的一种柠檬醛的荧光检测方法,其特征在于,具体步骤是:将所述荧光显色剂溶解于甲醇中制成浓度为1×10-5mol/L~1×10-3mol/L的溶液,将待测物加入该溶液中,采用荧光发射光谱法检测其荧光强度,荧光强度与柠檬醛含量成正比,根据荧光强度获得待测物中的柠檬醛含量。
3.根据权利要求2所述的一种柠檬醛的荧光检测方法,其特征在于:先用所述荧光显色剂溶解于甲醇中制成的溶液检测不同浓度的柠檬醛标准品,绘制不同浓度的柠檬醛标准品的标准曲线,再用荧光显色剂溶解于甲醇中制成的溶液检测待测物,采用标准曲线法计算待测物中的柠檬醛含量。
4.根据权利要求2或3所述的一种柠檬醛的荧光检测方法,其特征在于:所述荧光发射光谱法检测荧光显色剂的激发波长为327nm,发射波长为403nm。
5.根据权利要求2或3所述的一种柠檬醛的荧光检测方法,其特征在于:所述荧光发射光谱法检测柠檬醛的激发波长为378nm,在548nm测定荧光强度。
7.根据权利要求6所述的一种柠檬醛的荧光检测方法,其特征在于:反应时间为30min~2h,反应温度为5℃~37℃。
8.根据权利要求6所述的一种柠檬醛的荧光检测方法,其特征在于:所述催化剂是Pd/C,所述有机溶剂是甲醇或乙醇。
9.根据权利要求6所述的一种柠檬醛的荧光检测方法,其特征在于:所述如式Ⅱ所示结构的化合物与水合联胺的摩尔比为1:0.1至1:3,所述催化剂与如式Ⅱ所示结构的化合物的摩尔比为1:1~1:30。
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