两种果糖衍生物的合成、卷烟保润性能及毒理学试验
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- 英文论文题名：Synthesis of Two New Fructose Derivatives and its Application in Cigarette
- 论文作者：陈芝飞 ; 孙志涛 ; 芦昶彤 ; 马宇平 ; 屈展 ; 马骥 ; 毛健
- 英文论文作者：CHEN Zhifei ; SUN Zhitao ; LU Changtong ; MA Yuping ; QU Zhan ; MA Ji ; MAO Jian ; Technology Center ; China Tobacco Henan Industrial Co. ; Ltd. ; Zhengzhou Tobacco Research Institute of CNTC
- 年：2016
- 作者机构：河南中烟工业有限责任公司技术中心;中国烟草总公司郑州烟草研究院;
- 论文关键词：1-O-羧甲基-D-果糖 ; 1-O-羟乙基-D-果糖 ; 卷烟 ; 保润剂 ; 保润性能 ; 毒理学试验
- 英文论文关键词：1-O-Carboxymethyl-D-Fructose ; 1-O-Hydroxyethyl-D-Fructose ; Cigarette ; Humectant ; Moisture retentivity ; Toxicology tests
- 会议召开时间：2016-12-01
- 会议录名称：中国烟草学会2016年度优秀论文汇编——烟草工业主题
- 语种：中文
- 分类号：TS452
- 学会代码：ZGYG
- 学会名称：中国烟草学会
- 页数：14
- 文件大小：1166k
- 原文格式：D
摘要
以D-果糖(Ⅰ)为起始原料,经羟基保护、亲核取代、皂化或还原反应、脱保护反应分别得到化合物Ⅴ和Ⅶ,用IR、~1H NMR和~(13)C NMR谱表征了合成产物的结构,以HR-MS对Ⅴ和Ⅶ作进一步结构表征。以D-果糖、丙二醇和甘油为对照,以烟丝含水率为指标对Ⅴ和Ⅶ的物理保润性能进行评价;对Ⅴ和Ⅶ进行了卷烟烟气危害性指数评价和毒理学测试分析。结果表明:①化合物Ⅴ和Ⅶ为目标产物1-O-羧甲基-D-果糖和1-O-羟乙基-D-果糖,其反应总收率分别为55.0%和47.1%;②Ⅴ和Ⅶ的保湿性能均优于D-果糖、丙二醇和甘油,其中Ⅴ优势明显;③添加Ⅴ和Ⅶ对卷烟烟气危害性指数无负面影响;与空白卷烟相比,添加Ⅴ和Ⅶ的卷烟均未引起MTT细胞毒性试验、体外微核试验和细菌回复突变试验的测试结果有显著性增加。
1-O-Carboxymethyl-D-Fructose(Ⅴ) and 1-O-Hydroxyethyl-D- Fructose(Ⅶ) were synthesized from D-fructose( Ⅰ) with hydroxyl protection, nucleophilic substitution, saponification or reduction and deprotection reactions. The structures of the products in each synthesized step were characterized via IR, 1H NMR and 13 C NMR. Both of Ⅴ and Ⅶ are further characterized by HR-MS. Their moisture retentivity was tested by tobacco and compared with that of D-fructose, propylene glycol and glycerin. To evaluate cigarette smoke hazard of Ⅴ and Ⅶ, the toxicology test was carried out. After the data were analysed, the result showed that: 1) The synthesized compounds Ⅴ and Ⅶ were the target products, and the final total yields were 55.0% and 47.1% respectively; 2) They were better than D-fructose, propylene glycol and glycerin in the moisture retentivity, and the former had more obvious advantage. 3) It had no negative effect on the risk of cigarette mainstream smoke hazard index with adding Ⅴ and Ⅶ into cigarettes; compared with the blank cigarette, add Ⅴ and Ⅶ cigarette could not induce MTT cell toxicity test, micronucleus test and bacterial reverse mutation test results have significant increase.
1-O-Carboxymethyl-D-Fructose(Ⅴ) and 1-O-Hydroxyethyl-D- Fructose(Ⅶ) were synthesized from D-fructose( Ⅰ) with hydroxyl protection, nucleophilic substitution, saponification or reduction and deprotection reactions. The structures of the products in each synthesized step were characterized via IR, 1H NMR and 13 C NMR. Both of Ⅴ and Ⅶ are further characterized by HR-MS. Their moisture retentivity was tested by tobacco and compared with that of D-fructose, propylene glycol and glycerin. To evaluate cigarette smoke hazard of Ⅴ and Ⅶ, the toxicology test was carried out. After the data were analysed, the result showed that: 1) The synthesized compounds Ⅴ and Ⅶ were the target products, and the final total yields were 55.0% and 47.1% respectively; 2) They were better than D-fructose, propylene glycol and glycerin in the moisture retentivity, and the former had more obvious advantage. 3) It had no negative effect on the risk of cigarette mainstream smoke hazard index with adding Ⅴ and Ⅶ into cigarettes; compared with the blank cigarette, add Ⅴ and Ⅶ cigarette could not induce MTT cell toxicity test, micronucleus test and bacterial reverse mutation test results have significant increase.
引文
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[2]张效康.保润剂保润性能及过程的试验[J].烟草科技,1994(4):11-12.
[3]康跃进,张爱忠,许淑红.丙二醇在卷烟加料中的应用[J].烟草科技,1996(4):29.
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[7]王明峰,朱保昆,者为,等.多糖类新型保润剂BR-22的开发及应用研究[J].食品工业,2010(5):49-51.
[8]易锦满,文俊,杨庆.几种保润剂性能比较[J].烟草科技,2006(4):9-12.
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[10]张利梅,张卫红,冯亚青,等.α-D-呋喃阿洛糖衍生物的合成[J].化学工业与工程,2004(6):414-417.
[11]徐仲杰,卢伟京,卢浩.13C6-1,2?5,6-O-双异丙叉-α-D-呋喃葡萄糖的合成[J].同位素,2011,24(4):229-233.
[12]Beksan E,Schieberie P,Robert F,et al.Synthesis and sensory characterization of novel umami-tasting glutamate glycoconjugates[J].J Agric Food Chem,2003,51(18):5428-5436.
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[16]于世钧,郭宏.Li Al H4和Na BH4的还原反应[J].辽宁师范大学学报,2003,26(1):56-58.
[17]何保江,刘强,赵明月,等.烟草保润性能测试方法[J].烟草科技,2009(2):25-28.
[18]Luh T Y.Chelation assistance in the activation of CS and CO bonds[J].Synlett,1996(3):201-208.
[19]刘立全,周雅宁,龚安达.烟草工业减害研究进展[J].烟草科技,2011(2):25-34.
[20]谢剑平,刘惠民,朱茂祥,等.卷烟烟气危害性指数研究[J].烟草科技,2009(2):5-15.
[21]YQ 2—2011,烟草及烟草制品烟气安全性生物学评价第1部分:中性红细胞毒性法
[22]YQ/T 42—2013烟草及烟草制品烟气安全性生物学评价MTT细胞毒性法
[23]YQ/T 43—2013烟草及烟草制品烟气安全性生物学评价BEAS-2B细胞体外微核试验
[24]YQ3-2011烟草及烟草制品烟气安全性生物学评价第2部分:细菌回复突变试验(Ames试验)
[25]侯成敏,陈文宁,陈玉放,等.糖类结构的光谱分析的特点[J].天然产物研究与开发,2012,24:556-561.
[2]张效康.保润剂保润性能及过程的试验[J].烟草科技,1994(4):11-12.
[3]康跃进,张爱忠,许淑红.丙二醇在卷烟加料中的应用[J].烟草科技,1996(4):29.
[4]戴建国.新型保润剂NCS在卷烟加料中的应用[J].烟草科技,1996(4):28-29.
[5]黄强,李楠,蒋元力.固定化酶反应器制备新型烟草保润剂的研究[J].郑州工业大学学报,1999,20(4):50-52.
[6]阮晓明,王青海,徐海涛,等.新型天然保润剂PDS在卷烟中的应用[J].烟草科技,2006(9):23-25.
[7]王明峰,朱保昆,者为,等.多糖类新型保润剂BR-22的开发及应用研究[J].食品工业,2010(5):49-51.
[8]易锦满,文俊,杨庆.几种保润剂性能比较[J].烟草科技,2006(4):9-12.
[9]陈芝飞,孙志涛,芦昶彤,等.6-O-羧甲基-D-吡喃半乳糖的合成及应用[J].烟草科技,2012(12):52-55.
[10]张利梅,张卫红,冯亚青,等.α-D-呋喃阿洛糖衍生物的合成[J].化学工业与工程,2004(6):414-417.
[11]徐仲杰,卢伟京,卢浩.13C6-1,2?5,6-O-双异丙叉-α-D-呋喃葡萄糖的合成[J].同位素,2011,24(4):229-233.
[12]Beksan E,Schieberie P,Robert F,et al.Synthesis and sensory characterization of novel umami-tasting glutamate glycoconjugates[J].J Agric Food Chem,2003,51(18):5428-5436.
[13]Shyluk W P,Timell T E.Synthesis of four carboxymethyl ethers of glucose[J].Canadian Journal of Chemistry,1955,34(5):575-582.
[14]Shyluk W P,Timell T E.A new method for preparing hydroxyethyl ethers of glucose[J].Canadian Journal of Chemistry,1956,34(3):571-574.
[15]Fernandez J M G,Mellet C O,Marin A M,et al.A mild and efficient procedure to remove acetal and dithioacetal protecting groups in carbohydrate derivatives using2,3-dichloro-5,6-dicyano-1,4-benzoquinone[J].Carbohydrate Research,1995,27(2):263-268.
[16]于世钧,郭宏.Li Al H4和Na BH4的还原反应[J].辽宁师范大学学报,2003,26(1):56-58.
[17]何保江,刘强,赵明月,等.烟草保润性能测试方法[J].烟草科技,2009(2):25-28.
[18]Luh T Y.Chelation assistance in the activation of CS and CO bonds[J].Synlett,1996(3):201-208.
[19]刘立全,周雅宁,龚安达.烟草工业减害研究进展[J].烟草科技,2011(2):25-34.
[20]谢剑平,刘惠民,朱茂祥,等.卷烟烟气危害性指数研究[J].烟草科技,2009(2):5-15.
[21]YQ 2—2011,烟草及烟草制品烟气安全性生物学评价第1部分:中性红细胞毒性法
[22]YQ/T 42—2013烟草及烟草制品烟气安全性生物学评价MTT细胞毒性法
[23]YQ/T 43—2013烟草及烟草制品烟气安全性生物学评价BEAS-2B细胞体外微核试验
[24]YQ3-2011烟草及烟草制品烟气安全性生物学评价第2部分:细菌回复突变试验(Ames试验)
[25]侯成敏,陈文宁,陈玉放,等.糖类结构的光谱分析的特点[J].天然产物研究与开发,2012,24:556-561.