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堆心菊素 | 547-17-1

中文名称
堆心菊素
中文别名
胡萝卜甾醇;土木香素;叶黄素棕榈酸酯;叶黄素二棕榈酸酯
英文名称
dipalmitoyl-lutein
英文别名
lutein bispalmitate;all-trans-lutein dipalmitate;(3R,3'R,6'R)-lutein dipalmitate;lutein dipalmitate;(3R,3'R,6'R)-3,3'-bis-palmitoyloxy-β,ε-carotene;all-trans-dipalmitoyllutein;lutein-C16:0,C16:0;all-trans-DPL;helenien;(3R,3'R,6'R)-3,3'-Bis-palmitoyloxy-β,ε-carotin;(3R,3'R,6'R)-β,ε-carotene-3,3'-diol, dihexadecanoate;(6'R)-β,ε-carotene-3(R),3'(R)-diol dipalmitate;(3R,3'R,6'R)-lutein bispalmitate;[(1R)-4-[(1E,3E,5E,7E,9E,11E,13E,15E,17E)-18-[(1R,4R)-4-hexadecanoyloxy-2,6,6-trimethylcyclohex-2-en-1-yl]-3,7,12,16-tetramethyloctadeca-1,3,5,7,9,11,13,15,17-nonaenyl]-3,5,5-trimethylcyclohex-3-en-1-yl] hexadecanoate
堆心菊素化学式
CAS
547-17-1
化学式
C72H116O4
mdl
——
分子量
1045.71
InChiKey
YHGJHDJZIOYZIR-URPSFYETSA-N
BEILSTEIN
——
EINECS
——
  • 物化性质
  • 计算性质
  • ADMET
  • 安全信息
  • SDS
  • 制备方法与用途
  • 上下游信息
  • 反应信息
  • 文献信息
  • 表征谱图
  • 同类化合物
  • 相关功能分类
  • 相关结构分类

物化性质

  • 熔点:
    82 °C
  • 沸点:
    949.7±65.0 °C(Predicted)
  • 密度:
    0.96±0.1 g/cm3(Predicted)
  • LogP:
    28.331 (est)

计算性质

  • 辛醇/水分配系数(LogP):
    26.8
  • 重原子数:
    76
  • 可旋转键数:
    42
  • 环数:
    2.0
  • sp3杂化的碳原子比例:
    0.67
  • 拓扑面积:
    52.6
  • 氢给体数:
    0
  • 氢受体数:
    4

安全信息

  • 储存条件:
    储存条件:2-8°C,避光保存,确保干燥并密封。

SDS

SDS:28aeee0101d0bfc0b9e11fc57b5bf2a6
查看

制备方法与用途

堆心菊概述

堆心菊属于菊科堆心菊属植物,不仅可供观赏,还具有药用价值。在中医中,通常使用带花全草的堆心菊入药,用于治疗肝肾阴虚、头昏目眩、腰膝酸软、须发早白及风湿性关节炎等症状。

功效作用

堆心菊以其带花全草入药,在中医中有多种应用。研究表明,堆心菊素是一种萜类化合物,具有显著的抗肿瘤效果,对Hela、WI-38、H.Ep-2和W-18Va-2细胞均表现出抑制作用。此外,它还具备一定的抗炎抗菌功效。

提取方法

一种从堆心菊叶中制备堆心菊素的方法如下:首先将堆心菊原料粉碎成20-80目,然后投入超临界萃取釜中,使用超临界二氧化碳流体进行萃取。随后,通过高速逆流色谱法分离萃取物,并利用紫外检测器在线监测目标成分的收集过程。最后,经过浓缩和结晶处理后即可获得堆心菊素。

上下游信息

  • 上游原料
    中文名称 英文名称 CAS号 化学式 分子量
    叶黄素 lutein 127-40-2 C40H56O2 568.883
  • 下游产品
    中文名称 英文名称 CAS号 化学式 分子量
    玉米黄质 zeaxanthin 144-68-3 C40H56O2 568.883

反应信息

  • 作为反应物:
    描述:
    堆心菊素三氯氧磷 作用下, 以 正己烷 为溶剂, 反应 24.0h, 生成 2',3'-anhydrolutein palmitate 、 3,4-anhydrolutein palmitate
    参考文献:
    名称:
    人血浆提取物中类胡萝卜素及其氧化产物的分离与鉴定。
    摘要:
    在反相和基于Sillca的腈键色谱柱上,通过高效液相色谱(HPLC)从人血浆提取物中分离出了十八种类胡萝卜素以及维生素A和两种形式的维生素E(γ-和α-生育酚) 。按照在C18反相色谱柱上的色谱洗脱顺序,类胡萝卜素被鉴定为(3R,3'R,6'R)-β,ε-胡萝卜素-3,3'-二醇[(3R,3'R ,6'R)-叶黄素],(3R,3'R)-β,β-胡萝卜素-3,3'-二醇[(3R,3'R)-玉米黄质],5,6-二羟基-5,6 -dihydro-psi,psi-胡萝卜素,3-羟基-2',3'-二氢-β,ε-胡萝卜素-3-醇,3-羟基-β-胡萝卜素,psi,psi-胡萝卜素,7,8-二氢-psi,psi-胡萝卜素,beta,psi-胡萝卜素,7,8,7',8'-四氢psi,psi-胡萝卜素,beta,ε-胡萝卜素,beta,beta-胡萝卜素,7,8,11,12 ,7',8'-hexahydro-psi,psi-胡萝卜素和7
    DOI:
    10.1021/ac00042a016
  • 作为产物:
    参考文献:
    名称:
    Identification of Synthetic Regioisomeric Lutein Esters and Their Quantification in a Commercial Lutein Supplement
    摘要:
    Synthetic mixtures of 24 mono- and diesters of the asymmetric hydroxylated carotenoid lutein with lauric, myristic, palmitic, and stearic acids were analyzed by liquid chromatography-ultraviolet/visible spectroscopy (LC-UV-vis) and characterized by LC-mass spectrometry (MS) and nuclear magnetic resonance spectroscopy (NMR). These compounds were then used for identifying the composition of a commercial lutein supplement. This is the first report of chromatographic separation of mixed fatty acid lutein diesters. Preferential MS loss of fatty acids or water occurred initially at the 3'-hydroxy position in the epsilon-ionone ring and subsequently at the 3-hydroxy position in the beta-ionone ring. This selective fragmentation leads to facile assignment of the specific fatty acids to the appropriate regioisomeric ionone ring. A commercial lutein supplement contained low levels of two pairs of regioisomeric monoesters and nearly equal levels of three homogeneous diesters and five pairs of mixed diesters. Palmitic acid was the predominant fatty acid, with lower amounts of myristic, stearic, and lauric acids.
    DOI:
    10.1021/jf070357n
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文献信息

  • [EN] PROCESS FOR THE PREPARATION OF ALPHA- AND BETA-CRYPTOXANTHIN<br/>[FR] PROCESSUS DE PREPARATION D'ALPHA ET DE BETA-CRYPTOXANTHINE
    申请人:UNIV MARYLAND
    公开号:WO2005044769A1
    公开(公告)日:2005-05-19
    The present invention relates to a process for converting lutein and/or lutein esters to β-cryptoxanthin and α-cryptoxanthin, suitable for human consumption as dietary supplements, by employing safe and environmentally friendly reagents. In the first synthetic step, commercially available lutein and/or lutein esters are transformed into a mixture of dehydration products of lutein (anhydroluteins) in the presence of a catalytic amount of an acid. The resulting anhydroluteins are then converted to β-cryptoxanthin (major product) and α-cryptoxanthin (minor product) by heterogeneous catalytic hydrogenation employing transition elements of group VIII in a variety of organic solvents under atmospheric pressure of hydrogen. A novel feature of this invention is the regioselective hydrogenation of anhydroluteins while the highly conjugated polyene chain of these carotenoids remains intact.
    本发明涉及一种将叶黄素和/或叶黄素酯转化为β-隐子黄质和α-隐子黄质的过程,适合作为膳食补充剂供人类消费,采用安全和环保的试剂。在第一合成步骤中,利用商业上可获得的叶黄素和/或叶黄素酯在少量酸的存在下转化为叶黄素的脱水产物混合物(脱水叶黄素)。然后,利用过渡元素群VIII在各种有机溶剂中,在氢气大气压下进行异质催化加氢,将所得的脱水叶黄素转化为β-隐子黄质(主要产物)和α-隐子黄质(次要产物)。本发明的一个新特点是在保持这些类胡萝卜素高度共轭多烯链完整的情况下,对脱水叶黄素进行区域选择性加氢。
  • Separation and identification of carotenoids and their oxidation products in the extracts of human plasma
    作者:Frederick Khachik、Gary R. Beecher、Mudlagiri B. Goli、William R. Lusby、James C. Smith
    DOI:10.1021/ac00042a016
    日期:1992.9.15
    Eighteen carotenoids as well as vitamin A and two forms of vitamin E (gamma- and alpha-tocopherol) have been separated from extracts of human plasma by high-performance liquid chromatography (HPLC) on reversed-phase and sillca-based nitrile-bonded columns. In the order of chromatographic elution on a C18 reversed-phase column, the carotenoids were identified as (3R,3'R,6'R)-beta, epsilon-carotene-3
    在反相和基于Sillca的腈键色谱柱上,通过高效液相色谱(HPLC)从人血浆提取物中分离出了十八种类胡萝卜素以及维生素A和两种形式的维生素E(γ-和α-生育酚) 。按照在C18反相色谱柱上的色谱洗脱顺序,类胡萝卜素被鉴定为(3R,3'R,6'R)-β,ε-胡萝卜素-3,3'-二醇[(3R,3'R ,6'R)-叶黄素],(3R,3'R)-β,β-胡萝卜素-3,3'-二醇[(3R,3'R)-玉米黄质],5,6-二羟基-5,6 -dihydro-psi,psi-胡萝卜素,3-羟基-2',3'-二氢-β,ε-胡萝卜素-3-醇,3-羟基-β-胡萝卜素,psi,psi-胡萝卜素,7,8-二氢-psi,psi-胡萝卜素,beta,psi-胡萝卜素,7,8,7',8'-四氢psi,psi-胡萝卜素,beta,ε-胡萝卜素,beta,beta-胡萝卜素,7,8,11,12 ,7',8'-hexahydro-psi,psi-胡萝卜素和7
  • Identification of Synthetic Regioisomeric Lutein Esters and Their Quantification in a Commercial Lutein Supplement
    作者:J. Christopher Young、El-Sayed M. Abdel-Aal、Iwona Rabalski、Barbara A. Blackwell
    DOI:10.1021/jf070357n
    日期:2007.6.1
    Synthetic mixtures of 24 mono- and diesters of the asymmetric hydroxylated carotenoid lutein with lauric, myristic, palmitic, and stearic acids were analyzed by liquid chromatography-ultraviolet/visible spectroscopy (LC-UV-vis) and characterized by LC-mass spectrometry (MS) and nuclear magnetic resonance spectroscopy (NMR). These compounds were then used for identifying the composition of a commercial lutein supplement. This is the first report of chromatographic separation of mixed fatty acid lutein diesters. Preferential MS loss of fatty acids or water occurred initially at the 3'-hydroxy position in the epsilon-ionone ring and subsequently at the 3-hydroxy position in the beta-ionone ring. This selective fragmentation leads to facile assignment of the specific fatty acids to the appropriate regioisomeric ionone ring. A commercial lutein supplement contained low levels of two pairs of regioisomeric monoesters and nearly equal levels of three homogeneous diesters and five pairs of mixed diesters. Palmitic acid was the predominant fatty acid, with lower amounts of myristic, stearic, and lauric acids.
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