9--虾青素 | 113085-04-4

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 异戊烯醇脂质
• 中文名称: 9--虾青素
• 英文名称: 9-cis-astaxanthin
• 英文别名: (9Z)-astaxanthin；Astaxanthin, (9Z)-；(6S)-6-hydroxy-3-[(1E,3Z,5E,7E,9E,11E,13E,15E,17E)-18-[(4S)-4-hydroxy-2,6,6-trimethyl-3-oxocyclohexen-1-yl]-3,7,12,16-tetramethyloctadeca-1,3,5,7,9,11,13,15,17-nonaenyl]-2,4,4-trimethylcyclohex-2-en-1-one
• CAS: 113085-04-4
• 化学式: C₄₀H₅₂O₄
• 分子量: 596.85
• InChiKey: MQZIGYBFDRPAKN-QHKQXWLXSA-N

物化性质

• 沸点：
  774.0±60.0 °C(Predicted)
• 密度：
  1.071±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  10.3
• 重原子数：
  44
• 可旋转键数：
  10
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.4
• 拓扑面积：
  74.6
• 氢给体数：
  2
• 氢受体数：
  4

安全信息

• WGK Germany：
  3

反应信息

• 作为产物：
  描述：

  虾青素 以 丙酮 、 Petroleum ether 为溶剂， 反应 12.0h， 生成 9--虾青素 、 13--虾青素
  参考文献：
  名称：

  Isomer Separation of trans-Astaxanthin, 9-cis-Astaxanthin and 13-cis-Astaxanthin by Ligand Exchange Chromatography

  摘要：

  虾青素分子有两种几何异构体，即顺式或反式，这是因为多烯链上有双键。使用普通技术很难分离这些异构体。我们使用虾青素立体异构体研究了配体交换色谱法分离立体异构体的条件。采用 C18 色谱柱，流动相为乙腈-氯仿-甲醇手性流动相添加剂溶液（含有不同浓度的 L-丝氨酸和硫酸铜），流速为 0.5 mL/min。评估了不同种类和浓度的配体、二价配体离子和有机改性剂的影响。通过热处理虾青素标准品可以得到虾青素异构体，并通过紫外可见光谱和核磁共振光谱进行了确认。

  DOI：

  10.14233/ajchem.2016.19547

文献信息

• Bioaccessibility, Cellular Uptake, and Transport of Astaxanthin Isomers and their Antioxidative Effects in Human Intestinal Epithelial Caco-2 Cells
  作者：Cheng Yang、Hua Zhang、Ronghua Liu、Honghui Zhu、Lianfu Zhang、Rong Tsao

  DOI：10.1021/acs.jafc.7b04254

  日期：2017.11.29

  concentrations in human plasma than all-E-astaxanthin in reported studies. All three astaxanthin isomers were effective in maintaining cellular redox homeostasis as seen in the antioxidant enzyme (CAT, SOD) activities ; 9Z- and 13Z- astaxanthins exhibited a higher protective effect than all-E-astaxanthin against oxidative stress as demonstrated by the lower cellular uptake of Z-astaxanthins and lower secretion

  使用体外消化模型和人肠道Caco-2细胞研究了三种虾青素几何异构体的生物可及性，生物利用度和抗氧化活性。这项研究表明，在体外胃肠消化和细胞摄取过程中，全E-虾黄素的反式-顺式异构化和Z-虾青素的顺式-反异构化都可能发生。在体外消化过程中，13 Z-虾青素显示出比9 Z-和所有E-虾青素更高的生物可及性，9 Z-虾青素显示出比all- E-和13 Z更高的转运效率。-黄质黄素。这些可能解释了为什么在已报道的研究中在人血浆中发现的13 Z-和9 Z-虾青素的浓度高于全E-虾青素。从抗氧化酶（CAT，SOD）的活性来看，所有三种虾青素异构体均能有效维持细胞氧化还原稳态。9 ž -和13种ž -虾青素类表现出比清一色更高的保护作用ë -虾青素对氧化应激通过的下细胞摄取所证明Ž -astaxanthins和下部的分泌和基因表达中的Caco的促炎症细胞因子IL-8的-2细胞用H 2 O 2处理。我们首
• Oral Supplementation with Z-Isomer-Rich Astaxanthin Inhibits Ultraviolet Light-Induced Skin Damage in Guinea Pigs
  作者：Masaki Honda、Hakuto Kageyama、Yelin Zhang、Takashi Hibino、Motonobu Goto

  DOI：10.3390/md20070414

  日期：——

  The effect of oral supplementation with astaxanthin of different Z-isomer ratios on ultraviolet (UV) light-induced skin damage in guinea pigs was investigated. Astaxanthin with a high Z-isomer content was prepared from the all-E-isomer via thermal isomerization. Intact (all-E)-astaxanthin and the prepared Z-isomer-rich astaxanthin were suspended in soybean oil and fed to guinea pigs for three weeks

  研究了口服补充不同Z异构体比例的虾青素对豚鼠紫外线 (UV) 光诱导的皮肤损伤的影响。具有高Z异构体含量的虾青素由全E异构体通过热异构化制备。完整（全E）-虾青素和制备的Z富含-异构体的虾青素悬浮在大豆油中，喂给豚鼠三周。在测试饮食补充开始后的第 7 天，对背部皮肤进行紫外线照射，并评估皮肤参数，如弹性、经表皮失水 (TEWL) 和色素沉着 (黑色素和红斑值) . 食用富含全E异构体的虾青素饮食（E-AST-D；总Z异构体比率 = 3.2%）和富含Z异构体的虾青素饮食后，背部皮肤中的虾青素积累几乎相同(Z-AST-D；总Z-异构体比率 = 84.4%)；然而，总Z在补充 Z-AST-D 的情况下，皮肤中虾青素的异构体比例更高。两种饮食都抑制了紫外线引起的皮肤损伤作用，例如弹性降低和 TEWL 水平增加。在 E-AST-D 和 Z-AST-D 之间，Z-AST-D 表现出比 E-AST-D
• Rapid and Efficient Conversion of All-<i>E</i>-astaxanthin to 9<i>Z</i>- and 13<i>Z</i>-Isomers and Assessment of Their Stability and Antioxidant Activities
  作者：Cheng Yang、Lianfu Zhang、Hua Zhang、Qingrui Sun、Ronghua Liu、Jing Li、Leiyan Wu、Rong Tsao

  DOI：10.1021/acs.jafc.6b04962

  日期：2017.2.1

  An optimized isomerization method was developed by heating all-E-astaxanthin in ethyl acetate (70 degrees C) with I-TiO2 catalyst, yielding 22.7% and 16.9% of 9Z- and 13Z-astaxanthin, respectively, in 2 h, with 92-95% purity after semipreparative HPLC purification. 13Z-Astaxanthin had higher antioxidant activity than all-E- and 9Z-astaxanthins in oxygen radical absorbing capacity assay for lipophilic compounds, photochemiluminescence, and cellular antioxidant activity (CAA) assays, and 9Z-astaxanthin was higher in DPPH radical-scavenging activity assay and lower in CAA assay. All isomers were relatively stable between pH 2.0 and 11.6, except 13Z- and 9Z-astaxanthins at pH 2.0, suggesting they may be converted after passing the gastric phase in vivo. Metal ions did not significantly (p < 0.05) affect the stability. Results of the current study provides a means for further study into the mechanisms related to in vivo transformation and bioavailability of Z-astaxanthins, and their application in the development of functional foods and nutraceutical products.
• Isomer Separation of trans-Astaxanthin, 9-cis-Astaxanthin and 13-cis-Astaxanthin by Ligand Exchange Chromatography
  作者：Yu Ri Lee、Xiaoxia Li、Kyung Ho Row

  DOI：10.14233/ajchem.2016.19547

  日期：——

  The astaxanthin molecule has two geometric isomers, cis or trans on account of the double bond from the polyene chain. The separation of these isomers is quite difficult using ordinary techniques. The conditions of ligand exchange chromatography for stereoisomer separation were examined using an astaxanthin stereoisomer. A C18 column was used with a mobile phase consisting of an acetonitrile-chloroform-methanol chiral mobile phase additive solution (containing different concentrations of L-serine and copper sulfate) at flow rate of 0.5 mL/min. The effects of different kinds and concentrations of ligands, bivalent ligand ions and organic modifier were evaluated. The astaxanthin isomers could be obtained from heat-treating the astaxanthin standard, which were confirmed by the ultraviolet-visible and nuclear magnetic resonance spectroscopy.

  虾青素分子有两种几何异构体，即顺式或反式，这是因为多烯链上有双键。使用普通技术很难分离这些异构体。我们使用虾青素立体异构体研究了配体交换色谱法分离立体异构体的条件。采用 C18 色谱柱，流动相为乙腈-氯仿-甲醇手性流动相添加剂溶液（含有不同浓度的 L-丝氨酸和硫酸铜），流速为 0.5 mL/min。评估了不同种类和浓度的配体、二价配体离子和有机改性剂的影响。通过热处理虾青素标准品可以得到虾青素异构体，并通过紫外可见光谱和核磁共振光谱进行了确认。