(6S)-6-palmitoyloxy-3-[(all-E)-18-[(4S)-4-hydroxy-2,6,6-trimethyl-3-oxo-1-cyclohexenyl]-3,7,12,16-tetramethyloctadeca-1,3,5,7,9,11,13,15,17-nonaenyl]-2,4,4-trimethyl-1-cyclohex-2-enone

• 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: (6S)-6-palmitoyloxy-3-[(all-E)-18-[(4S)-4-hydroxy-2,6,6-trimethyl-3-oxo-1-cyclohexenyl]-3,7,12,16-tetramethyloctadeca-1,3,5,7,9,11,13,15,17-nonaenyl]-2,4,4-trimethyl-1-cyclohex-2-enone
• 英文别名: [(1S)-4-[(1E,3E,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]-3,5,5-trimethyl-2-oxocyclohex-3-en-1-yl] hexadecanoate
• 化学式: C₅₆H₈₂O₅
• 分子量: 835.264
• InChiKey: FOWDCVVFAAOETP-GVZDHKTGSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  18.2
• 重原子数：
  61
• 可旋转键数：
  26
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.55
• 拓扑面积：
  80.7
• 氢给体数：
  1
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  (6S)-6-palmitoyloxy-3-[(all-E)-18-[(4S)-4-hydroxy-2,6,6-trimethyl-3-oxo-1-cyclohexenyl]-3,7,12,16-tetramethyloctadeca-1,3,5,7,9,11,13,15,17-nonaenyl]-2,4,4-trimethyl-1-cyclohex-2-enone 在 air 作用下， 以 甲醇 为溶剂， 反应 3.0h， 生成 apo-10'-astaxanthinal monopalmitate
  参考文献：
  名称：

  Analysis of Palmitoyl Apo-astaxanthinals, Apo-astaxanthinones, and their Epoxides by UHPLC-PDA-ESI-MS

  摘要：

  Food products enriched with fatty acid-esterified xanthophylls may result in deviating dietary apo-carotenoids. Therefore, free astaxanthin and its mono- and dipalmitate esters were subjected to two degradation processes in a methanolic model system: light-accelerated autoxidation and hypochlorous acid/hypochlorite (HOCl/OCl-) bleaching. Reversed phase ultrahigh-performance liquid chromatography photodiode array with in-line electrospray ionization mass spectrometry (RP-UHPLC-PDA-ESI-MS) was used for assessment of degradation products. Apo-astaxanthinals and -astaxanthinones containing 3 (apo-9) to 10 (apo-8') conjugated double bonds were found upon autoxidation for all three types of astaxanthin (except free apo-8?-astaxanthinal). Fragmentation of [M + H](+) and [M + Na](+) parent masses of apo-astaxanthins from dipalmitate astaxanthin indicated palmitate esterification. Astaxanthin monopalmitate degradation resulted in a mixture of free and palmitate apo-astaxanthins. HOCl/OCl rapidly converted the astaxanthins into a mixture of epoxy-apo-9- and epoxy-apo-13-astaxanthinones. The palmitate ester bond was hardly affected by autoxidation, whereas for HOCl/OCl the ester bond of the apo-astaxanthin palmitoyl esters was degraded.

  DOI：

  10.1021/jf503520q
• 作为产物：
  描述：

  虾青素 、 棕榈酸 在 N,N'-羰基二咪唑 、 溶剂黄146 作用下， 以 二氯甲烷 为溶剂， 反应 26.0h， 生成 (6S)-6-palmitoyloxy-3-[(all-E)-18-[(4S)-4-hydroxy-2,6,6-trimethyl-3-oxo-1-cyclohexenyl]-3,7,12,16-tetramethyloctadeca-1,3,5,7,9,11,13,15,17-nonaenyl]-2,4,4-trimethyl-1-cyclohex-2-enone
  参考文献：
  名称：

  METHOD FOR PRODUCING ASTAXANTHIN ESTERS

  摘要：

  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。

  公开号：

  US20170305849A1

文献信息

• [EN] PROCESS FOR PREPARING OF CAROTENOID MONO-ESTERS<br/>[FR] PROCÉDÉ DE PRÉPARATION DE MONO-ESTERS DE CAROTÉNOÏDES
  申请人：BASF SE

  公开号：WO2018050795A1

  公开（公告）日：2018-03-22

  The present invention relates to a process for preparing a carotenoid mono-ester of the formula (I), including the stereoisomers of formula (I), wherein, R1 is e.g. hydrogen, C1-C20-alkyl, C2-C20-alkenyl, C4-C20-alkdienyl, C6-C20-alktrienyl or C8-C20- alktetraenyl, R2 is e.g. hydrogen or -NRaRb, wherein Ra is e.g. hydrogen, C1-C4-alkyl, -C(O)-C1-C3-alkyl, -Boc or -Cbz, Rb is e.g. hydrogen or C1-C4-alkyl, R3 is e.g. hydrogen, and X1, X2 are independently from each other CH2 or C=O, which comprises reacting a phosphonium salt of the formula (II) or a stereoisomer thereof: formula (II) wherein X1 is as defined for formula (I), R4 is phenyl, tert-butyl or tolyl, and Y- is a suitable counteranion, with a 12'-apocarotenal ester of the formula (III) or a stereoisomer thereof: formula (III) wherein X2, R1, R2, and R3 are as defined for formula (I), in the presence of a base or a cryptobase.

  本发明涉及一种制备公式（I）的类胡萝卜素单酯的方法，包括公式（I）的立体异构体，其中，R1是氢、C1-C20烷基、C2-C20烯基、C4-C20二烯基、C6-C20三烯基或C8-C20四烯基，R2是氢或-NRaRb，其中Ra是氢、C1-C4烷基、-C（O）-C1-C3烷基、-Boc或-Cbz，Rb是氢或C1-C4烷基，R3是氢，X1、X2分别独立地为CH2或C=O，其包括在碱或隐蔽碱存在下，将公式（II）的磷酸盐或其立体异构体：公式（II），其中X1如公式（I）所定义，R4是苯、叔丁基或甲苯基，Y-是适当的对阴离子，与公式（III）的12'-脱氢类胡萝卜醛酯或其立体异构体反应：公式（III），其中X2，R1，R2和R3如公式（I）所定义。
• 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。
• Analysis of Palmitoyl Apo-astaxanthinals, Apo-astaxanthinones, and their Epoxides by UHPLC-PDA-ESI-MS
  作者：Yannick Weesepoel、Harry Gruppen、Wouter de Bruijn、Jean-Paul Vincken

  DOI：10.1021/jf503520q

  日期：2014.10.22

  Food products enriched with fatty acid-esterified xanthophylls may result in deviating dietary apo-carotenoids. Therefore, free astaxanthin and its mono- and dipalmitate esters were subjected to two degradation processes in a methanolic model system: light-accelerated autoxidation and hypochlorous acid/hypochlorite (HOCl/OCl-) bleaching. Reversed phase ultrahigh-performance liquid chromatography photodiode array with in-line electrospray ionization mass spectrometry (RP-UHPLC-PDA-ESI-MS) was used for assessment of degradation products. Apo-astaxanthinals and -astaxanthinones containing 3 (apo-9) to 10 (apo-8') conjugated double bonds were found upon autoxidation for all three types of astaxanthin (except free apo-8?-astaxanthinal). Fragmentation of [M + H](+) and [M + Na](+) parent masses of apo-astaxanthins from dipalmitate astaxanthin indicated palmitate esterification. Astaxanthin monopalmitate degradation resulted in a mixture of free and palmitate apo-astaxanthins. HOCl/OCl rapidly converted the astaxanthins into a mixture of epoxy-apo-9- and epoxy-apo-13-astaxanthinones. The palmitate ester bond was hardly affected by autoxidation, whereas for HOCl/OCl the ester bond of the apo-astaxanthin palmitoyl esters was degraded.