astaxanthin dipalmitate | 112421-21-3

• 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
• 英文名称: astaxanthin dipalmitate
• 英文别名: astaxanthin hexadecanoic acid diester；di-O-palmitoyl-all-trans-astaxanthin；astaxanthin palmitin acid diester；[4-[(1E,3E,5E,7E,9E,11E,13E,15E,17E)-18-(4-hexadecanoyloxy-2,6,6-trimethyl-3-oxocyclohexen-1-yl)-3,7,12,16-tetramethyloctadeca-1,3,5,7,9,11,13,15,17-nonaenyl]-3,5,5-trimethyl-2-oxocyclohex-3-en-1-yl] hexadecanoate
• CAS: 112421-21-3
• 化学式: C₇₂H₁₁₂O₆
• 分子量: 1073.68
• InChiKey: OVCSBYMDXUESFD-CHSCTOIBSA-N

物化性质

• 沸点：
  998.4±65.0 °C(Predicted)
• 密度：
  0.99±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  26.1
• 重原子数：
  78
• 可旋转键数：
  42
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.64
• 拓扑面积：
  86.7
• 氢给体数：
  0
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  astaxanthin dipalmitate 在 rainbow trout intestine lipolytic enzymes 、 水 作用下， 反应 48.0h， 生成 3,3'-dihydroxy-β,β-carotene-4,4'-dione 、 astaxanthin palmitate
  参考文献：
  名称：

  鲑鱼鱼肠中微生物脂肪酶和脂解酶对虾青素二酯的脂肪酸选择性

  摘要：

  AbstractThe objective of the work described in this paper was to study a possible FA selectivity of digestive lipolytic enzymes isolated from salmon and trout intestines toward astaxanthin diesters of various FA composition and compare it with the FA selectivity of microbial lipase. Astaxanthin diesters of varying FA composition were prepared in excellent yields (>90%) by chemical esterification using a carbodiimide coupling aget. The astaxanthin diesters were screened in a hydrolysis reaction by various commercially available lipases. The highest conversion rates were observed with the Candida rugosa lipase, which discriminated against n−3 PUFA. The rate of hydrolysis was determined by HPLC. Digestive lipolytic enzymes isolated from salmon and rainbow trout intestines displayed reversed FA selectivity. Thus, astaxanthin diesters highly enriched with n−3 PUFA including EPA and DHA were observed to be hydrolyzed at a considerably higher rate than the more saturated esters. Similar trends in FA selectivity were observed in the hydrolysis of fish oil TAG by the digestive lipolytic enzyme mixtures.

  DOI：

  10.1007/s11746-004-0905-8
• 作为产物：
  描述：

  3,3'-dihydroxy-β,β-carotene-4,4'-dione 、 棕榈酸 在 4-二甲氨基吡啶 、 盐酸-N-乙基-Nˊ-(3-二甲氨基丙基)碳二亚胺 作用下， 以 二氯甲烷 为溶剂， 反应 24.0h， 以92%的产率得到astaxanthin dipalmitate
  参考文献：
  名称：

  鲑鱼鱼肠中微生物脂肪酶和脂解酶对虾青素二酯的脂肪酸选择性

  摘要：

  AbstractThe objective of the work described in this paper was to study a possible FA selectivity of digestive lipolytic enzymes isolated from salmon and trout intestines toward astaxanthin diesters of various FA composition and compare it with the FA selectivity of microbial lipase. Astaxanthin diesters of varying FA composition were prepared in excellent yields (>90%) by chemical esterification using a carbodiimide coupling aget. The astaxanthin diesters were screened in a hydrolysis reaction by various commercially available lipases. The highest conversion rates were observed with the Candida rugosa lipase, which discriminated against n−3 PUFA. The rate of hydrolysis was determined by HPLC. Digestive lipolytic enzymes isolated from salmon and rainbow trout intestines displayed reversed FA selectivity. Thus, astaxanthin diesters highly enriched with n−3 PUFA including EPA and DHA were observed to be hydrolyzed at a considerably higher rate than the more saturated esters. Similar trends in FA selectivity were observed in the hydrolysis of fish oil TAG by the digestive lipolytic enzyme mixtures.

  DOI：

  10.1007/s11746-004-0905-8

文献信息

• Identification and Quantification of Astaxanthin Esters in Shrimp (<i>Pandalus borealis</i>) and in a Microalga (<i>Haematococcus pluvialis</i>) by Liquid Chromatography−Mass Spectrometry Using Negative Ion Atmospheric Pressure Chemical Ionization
  作者：Dietmar E. Breithaupt

  DOI：10.1021/jf049780b

  日期：2004.6.1

  method allows for the first time the characterization of native astaxanthin esters in P. borealis and H. pluvialis without using time-consuming isolation steps with subsequent gas chromatographic analyses of fatty acid methyl esters. The results suggest that the pattern of astaxanthin-bound polyunsaturated fatty acids of P. borealis does not reflect the respective fatty acid pattern found in triacylglycerides

  负离子液相色谱-常压化学电离质谱法[负离子LC-（APCI）MS]用于鉴定商品虾（Pandalus borealis）和干燥微藻（Haematococcus pluvialis）样品中的虾青素酯。在分析之前，应用了使用正相固相萃取（SPE）柱的清洁步骤。以虾青素油酸酯作为模型化合物的回收率实验证明了该步骤的适用性（98.5 +/- 7.6％； n = 4）。虾青素酯在负离子LC-（APCI）MS中的分配基于分子离子（M *-）的检测和特征性碎片离子的形成，这是由一种或两种脂肪酸的损失导致的。使用虾青素校准曲线对单个虾青素酯进行定量，发现在要求的范围内（1-51微摩尔/升； r2 = 0.9996）是线性的。基于M *-的强度，信噪比为3：1和进样量为20 microL的检测限估计为0.05 microg / mL（游离虾青素），0.28 microg / mL（虾青素-C16：0）和0.78
• METHOD FOR PRODUCING ASTAXANTHIN ESTERS
  申请人：BASF SE

  公开号：US20170305849A1

  公开（公告）日：2017-10-26

  The invention describes an environmentally friendly, sustainable and cost-effective method for preparing astaxanthin diesters of the formula 1, in which astaxanthin of the formula 2 is doubly esterified with fatty acid chlorides of the general formula 3. For this purpose, compound 2 and 3 are reacted in an organic solvent in the presence of a nitrogen-containing base of the general formula 4. The invention further relates to the non-therapeutic use of the diester 1, in which R is a residue selected from the group consisting of C13-C19-alkyl, C13-C19-alkenyl, C13-C19-alkdienyl and C13-C19-alktrienyl, in human or animal nutrition and also the therapeutic use of the diester 1 prepared according to the method as a medicament and also as an ingredient in a medicinal preparation.

  该发明描述了一种环保、可持续且具有成本效益的制备式1的虾青素二酯的方法，其中式2的虾青素通过一般式3的脂肪酸氯化物双酯化。为此，化合物2和3在一种有机溶剂中在一般式4的含氮碱存在下反应。该发明还涉及虾青素二酯1的非治疗用途，其中R是从C13-C19-烷基、C13-C19-烯基、C13-C19-烷二烯基和C13-C19-烷三烯基组成的残基中选择，在人类或动物营养中的使用以及按照所述方法制备的虾青素二酯1作为药物的治疗用途以及作为药物制剂中的成分。
• Kuhn; Soerensen, Chemische Berichte, 1938, vol. 71, p. 1879
  作者：Kuhn、Soerensen

  DOI：——

  日期：——