CN110229167B - 一种利用五倍子制备鞣花酸的方法、制得的鞣花酸及其应用 - Google Patents
一种利用五倍子制备鞣花酸的方法、制得的鞣花酸及其应用 Download PDFInfo
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- ATJXMQHAMYVHRX-CPCISQLKSA-N Ellagic acid Natural products OC1=C(O)[C@H]2OC(=O)c3cc(O)c(O)c4OC(=O)C(=C1)[C@H]2c34 ATJXMQHAMYVHRX-CPCISQLKSA-N 0.000 title claims abstract description 59
- 229920002079 Ellagic acid Polymers 0.000 title claims abstract description 59
- 235000004132 ellagic acid Nutrition 0.000 title claims abstract description 59
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- FAARLWTXUUQFSN-UHFFFAOYSA-N methylellagic acid Natural products O1C(=O)C2=CC(O)=C(O)C3=C2C2=C1C(OC)=C(O)C=C2C(=O)O3 FAARLWTXUUQFSN-UHFFFAOYSA-N 0.000 title claims abstract description 59
- 238000000034 method Methods 0.000 title claims abstract description 29
- UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 claims abstract description 22
- LCPVQAHEFVXVKT-UHFFFAOYSA-N 2-(2,4-difluorophenoxy)pyridin-3-amine Chemical compound NC1=CC=CN=C1OC1=CC=C(F)C=C1F LCPVQAHEFVXVKT-UHFFFAOYSA-N 0.000 claims abstract description 20
- CHQMHPLRPQMAMX-UHFFFAOYSA-L sodium persulfate Substances [Na+].[Na+].[O-]S(=O)(=O)OOS([O-])(=O)=O CHQMHPLRPQMAMX-UHFFFAOYSA-L 0.000 claims abstract description 20
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- UIIMBOGNXHQVGW-DEQYMQKBSA-M Sodium bicarbonate-14C Chemical compound [Na+].O[14C]([O-])=O UIIMBOGNXHQVGW-DEQYMQKBSA-M 0.000 claims abstract description 5
- 150000007522 mineralic acids Chemical class 0.000 claims abstract description 5
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Abstract
本发明公开了一种利用五倍子制备鞣花酸的方法、制得的鞣花酸及其应用,包括以下步骤:S1、室温下将五倍子粉与去离子水混合后,搅拌1~3h后,过滤取上清液;S2、取上述操作制得的上清液,依次添加过硫酸钠和碳酸氢钠,调pH至8~9,室温下静置10~20h后用无机酸调节pH到3~6,固液分离后收集固体物即为制得的鞣花酸;其中,所述过硫酸钠的添加量为所述五倍子粉质量的(5~10)%,添加的过硫酸钠与碳酸氢钠的质量比为3:2。本发明方案先将水与五倍子混合浸取单宁酸,再经氧化、碱化、酸化处理得到鞣花酸,所有操作在常温常压下即可进行,反应条件温和,操作简便,制得的产品纯度高且收率好,具有良好的应用前景。
Description
技术领域
本发明涉及有机合成技术领域,具体涉及一种利用五倍子制备鞣花酸的方法、制得的鞣花酸及其应用。
背景技术
五倍子学名(Rhus chinensis Mill.),又名百虫仓、百药煎、棓子,为同翅目蚜虫科的角倍蚜或倍蛋蚜雌虫寄生于漆树科植物“盐肤木”及其同属其他植物的嫩叶或叶柄,刺伤而生成一种囊状聚生物虫瘿,经烘焙干燥后所得。此外,五倍子还是一种药材,可以治疗多种疾病。我国五倍子的主要产地集中分布于秦岭、大巴山、武当山、巫山、武陵、峨眉山、大娄山、大凉山等山区和丘陵地带。垂直分布为海拔250-1600米,以500-600米较为集中。五倍子中含有鞣酸,鞣酸具有沉淀蛋白质的作用,皮肤溃疡面、黏膜与其接触后,组织蛋白质即被凝固,形成一层保护膜,起收敛作用,同时小血管也被压迫收缩,血液凝结而呈止血作用。五倍子中所含鞣酸对正常小肠运动几乎影响,但由于其收敛作用而减轻肠道炎症,故可制止腹泻。体外试验表明:五倍子煎剂对金黄色葡萄球菌、乙型溶血性链球菌、肺炎球菌、绿脓杆菌、痢疾杆菌、炭疽杆菌、白喉杆菌、大肠杆菌、伤寒和副伤寒杆菌等均有明显的抑菌和杀菌作用。经用乙醚提出其鞣酸后的五倍子液仍有抑菌作用,但五倍子心部的煎剂无抗菌作用。
鞣花酸是一种多酚二内酯,是没食子酸的二聚衍生物。CAS号476-66-4,折射率1.5800,熔点≥360℃,分子式C14H6O8,沸点≥420℃,分子量302.19g/mol鞣花酸广泛存在于各种软果、坚果等植物组织中的一种天然多酚组分,鞣花酸与三氯化铁的显色反应呈蓝色,遇硫酸呈黄色。研究表明鞣花酸有很强的清除自由基和抗氧化能力。鞣花酸对氧自由基和羟自由基都有清除作用,其清除自由基的能力大小比芝麻酚、橄榄叶萃取物和叶黄素、元青花素等抗氧化物都高。鞣花酸表现出对化学物质诱导癌变及其他多种癌变有明显的抑制作用,尤其是对结肠癌、食管癌、肝癌、肺癌、舌及皮肤肿瘤等有很好的抑制作用。作为一种天然多酚,鞣花酸不溶于醚,在水、醇中的溶解度很低,溶于碱、吡啶、二甲基亚酚。鞣花酸在水中的溶解度随pH升高而升高,因此可用通过调节酸碱度纯化。
现有技术中,对鞣花酸检测方法包括:(1)紫光分光光度法,375nm为鞣花酸紫外特征吸收峰。该操作简便,误差小,需要的溶剂较少,经济成本,适用于工业产品中的鞣花酸含量分析。(2)高效液相色谱法(High Performance Liquid Chromatography,HPLC)(尤其是反相高效液相色谱法(Reverse Phase-High Performance Liquid Chromatography,RP-HPLC))是当下测定鞣花酸含量最普遍的方法,该方法操作简单,所需样品量少,测量时间短,实验结果准确,重现性好,但所需仪器较为昂贵。因此,目前主要应用实验研究。
然而不论紫光吸光光度法还是HPLC技术检测到的现有技术中提取得到的天然鞣花酸的纯度均较低,通常在20~30%左右。基于此,开发一种产率高且纯度好的鞣花酸具有重要意义。以五倍子作为制备原料,有望实现这一目的。然而现有技术中利用五倍子制备鞣花酸的工艺操作较为复杂,使得其工业生产成本较高,有必要进行进一步改进。
发明内容
本发明所要解决的第一个技术问题是:提供一种操作简便、产率高且纯度好的利用五倍子制备鞣花酸的方法。
本发明所要解决的第二个技术问题是:提供一种通过上述方法制得的鞣花酸。
本发明所要解决的第三个技术问题是:提供一种上述鞣花酸在抗氧化剂、抗癌剂或抑菌剂制备中的应用。
为了解决上述第一个技术问题,本发明采用的技术方案为:一种利用五倍子制备鞣花酸的方法,包括以下步骤:
S1、室温下将五倍子粉与去离子水混合后,搅拌1~3h后,过滤取上清液;
S2、取上述操作制得的上清液,依次添加过硫酸钠和碳酸氢钠,调pH至8~9,室温下静置10~20h后用无机酸调节pH到3~6,固液分离后收集固体物即为制得的鞣花酸;
其中,所述过硫酸钠的添加量为所述五倍子粉质量的(5~10)%,添加的过硫酸钠与碳酸氢钠的质量比为3:2。
进一步地,所述五倍子粉与去离子水按质量比为(5~15):100混合。
优选地,所述五倍子粉与去离子水按质量比为1:10混合。
进一步地,所述室温为20-25℃。
进一步地,所述步骤S2中,用30%NaOH调节pH值8~9。
进一步地,所述无机酸为盐酸;优选为浓盐酸。
进一步地,所述步骤S2中的静置时间为16h。
进一步地,所述步骤S2中,通过离心操作进行固液分离。
本发明的有益效果在于:鞣花酸在各领域有着广泛的应用,但鉴于其提取产率通常较差,使得其应用效果和范围仍受到一定限制;本发明方案先将水与五倍子混合浸取单宁酸,再经氧化、碱化、酸化处理得到鞣花酸,所有操作在常温常压下即可进行,反应条件温和,操作简便,制得的产品纯度高且收率好,具有良好的应用前景;本发明方案中通过预先添加过硫酸钠后,再调节溶液的pH值至碱性,保护含酚羟基成分不被氧化;先加入碳酸氢钠使溶液偏碱性,再添加氢氧化钠将溶液稳定为碱性条件,避免一开始加入强碱性的氢氧化钠使得溶液的pH变化过大,难以调控。
为了解决上述第二个技术问题,本发明采用的技术方案为:一种通过上述方法制得的鞣花酸。
为了解决上述第三个技术问题,本发明采用的技术方案为:一种上述鞣花酸在抗氧化剂、保湿剂、抗癌剂或抑菌剂的制备中的应用。
本发明的有益效果在于:本发明方案制得的鞣花酸固体纯度高且制备过程中使用的溶剂仅有水,未使用任何有机溶剂,制备过程环保且制得的鞣花酸安全无毒可以作为抗氧化剂、保湿剂、抗癌剂或祛痘杀菌剂添加于保健食品或化妆品中。
具体实施方式
为详细说明本发明的技术内容、所实现目的及效果,以下结合实施方式予以说明。
本发明实施例一为:一种利用五倍子制备鞣花酸的方法,包括以下步骤:
(1)取20g市售五倍子粉与200mL去离子水混合后倒入烧杯中,室温搅拌2h。
(2)用真空泵抽滤,弃去残渣。
(3)取步骤(2)中得到的提取液倒入锥形瓶,加1.5g过硫酸钠、1g碳酸氢钠,用30%氢氧化钠调pH到8.5,反应16h。
(4)用浓盐酸调pH到4左右,水洗,10000rpm离心5min,取沉淀。
(5)烘干后得到鞣花酸固体。
(6)重复以上实验操作3次,分别计算产率。
本发明对比例一为:一种利用五倍子制备鞣花酸的方法,包括以下步骤:
(1)取与实施例一同一来源市售五倍子粉的20g与200ml去离子水混合后倒入烧杯中,室温搅拌2h。
(2)用真空泵抽滤,弃去残渣。
(3)取步骤(2)中的提取液倒入锥形瓶,加1.5g过硫酸钠、1.0g碳酸氢钠,用30%氢氧化钠调pH到8.5,反应16h。
(4)用浓盐酸调pH到4左右,抽滤,将沉淀从滤膜刮下,烘干。
(5)称量,计算产率。
实施例1与对照例1的原料、产物重量信息如下表1所示:
表1
从上表1可以看出,本发明实施例方案巧妙地将其酸沉过程后传统固液分离的过滤方式用离心代替,避免了过滤取沉淀时产物粘在滤膜上难以去除,通过离心处理,可使得产率提升10%以上。
本发明实施例二为:一种利用五倍子制备鞣花酸的方法,其与实施例1的区别仅在于:过硫酸钠的添加量为1g,碳酸氢钠的质量为0.67g。
经称量计算得产率为44.3%。
本发明实施例三为:一种利用五倍子制备鞣花酸的方法,其与实施例1的区别仅在于:过硫酸钠的添加量为2g,碳酸氢钠的质量为1.34g。
经称量计算得产率为45.8%。
本发明对照例二为:一种利用五倍子制备鞣花酸的方法,其与实施例1的区别仅在于:利用等摩尔量的过氧化钠代替过硫酸钠。
经称量计算得产率为31.5%。
本发明对照例三为:一种利用五倍子制备鞣花酸的方法,其与实施例1的区别仅在于:过硫酸钠的添加量为2.5g,碳酸氢钠的质量为1.67g。
经称量计算得产率为38.2%。
本发明对照例四为:一种利用五倍子制备鞣花酸的方法,其与实施例1的区别仅在于:过硫酸钠的添加量为0.5g,碳酸氢钠的质量为0.33g。
经称量计算得产率为35.9%。
本发明对照例五为:一种利用五倍子制备鞣花酸的方法,其与实施例1的区别仅在于:过硫酸钠的添加量为1.5g,碳酸氢钠的质量为0g。
经称量计算得产率为25.4%。
本发明对照例六为:一种利用五倍子制备鞣花酸的方法,其与实施例1的区别仅在于:先添加碳酸氢钠,再添加过硫酸钠。
经称量计算得产率为32.7%。
取实施例1~3及对照例1~6制得的产物,通过紫外吸光光度法测定其中的鞣花酸含量,计算产物中鞣花酸纯度数据如下表2所示:
表2
从上表2中可以看出,碳酸氢钠的添加顺序、添加比例、过硫酸钠的添加量等均对制得的鞣花酸的产量及纯度具有重要影响。
以上所述仅为本发明的实施例,并非因此限制本发明的专利范围,凡是利用本发明说明书内容所作的等同变换,或直接或间接运用在相关的技术领域,均同理包括在本发明的专利保护范围内。
Claims (5)
1.一种利用五倍子制备鞣花酸的方法,其特征在于:包括以下步骤:
S1、室温下将五倍子粉与去离子水混合后,搅拌1~3h后,过滤取上清液;
S2、取上述操作制得的上清液,依次添加过硫酸钠和碳酸氢钠,调pH至8~9,室温下静置10~20h后用无机酸调节pH到3~6,固液分离后收集固体物即为制得的鞣花酸;
其中,所述过硫酸钠的添加量为所述五倍子粉质量的(5~10)%,添加的过硫酸钠与碳酸氢钠的质量比为3:2;
所述室温为20-25℃;
所述五倍子粉与去离子水按质量比为1:10混合。
2.根据权利要求1所述的利用五倍子制备鞣花酸的方法,其特征在于:所述步骤S2中,用30%NaOH调节pH值8~9。
3.根据权利要求1所述的利用五倍子制备鞣花酸的方法,其特征在于:所述无机酸为盐酸。
4.根据权利要求1所述的利用五倍子制备鞣花酸的方法,其特征在于:所述步骤S2中的静置时间为16h。
5.根据权利要求1所述的利用五倍子制备鞣花酸的方法,其特征在于:所述步骤S2中,通过离心操作进行固液分离。
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Effective date of registration: 20210730 Address after: 9 / F, building 5, Longyuan wisdom Park, No.2, hagongda Road, high tech Zone, Zhuhai City, Guangdong Province, 519000 Patentee after: Zhongke Xuanjia Medical Care (Zhuhai) Health Technology Co.,Ltd. Address before: 519000 room 110-320, building 18, creative Valley, No. 1889, Huandao East Road, Hengqin new area, Zhuhai, Guangdong (centralized office area) Patentee before: Zhuhai Xuan Jiajunhang Health Industry Development Co.,Ltd. |
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