10-deoxygeniposide tetraacetate | 20586-16-7

• 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: 10-deoxygeniposide tetraacetate
• 英文别名: deoxygeniposide tetraacetate；methyl (1S,4aS,7aS)-7-methyl-1-[(2S,3R,4S,5R,6R)-3,4,5-triacetyloxy-6-(acetyloxymethyl)oxan-2-yl]oxy-1,4a,5,7a-tetrahydrocyclopenta[c]pyran-4-carboxylate
• CAS: 20586-16-7
• 化学式: C₂₅H₃₂O₁₃
• 分子量: 540.521
• InChiKey: MNFADCCGRFHLCI-IFULQXDOSA-N

物化性质

• 沸点：
  592.9±50.0 °C(Predicted)
• 密度：
  1.33±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  0.7
• 重原子数：
  38
• 可旋转键数：
  13
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.64
• 拓扑面积：
  159
• 氢给体数：
  0
• 氢受体数：
  13

反应信息

• 作为反应物：
  描述：

  10-deoxygeniposide tetraacetate 在 dimethyl sulfide borane 、 sodium methylate 作用下， 以 四氢呋喃 、 甲醇 、 氯仿 为溶剂， 反应 3.0h， 生成 8-epiloganin
  参考文献：
  名称：

  10.1002/(sici)1099-0690(200004)2000:8<1623::aid-ejoc1623<3.0.co;2-y

  摘要：

  DOI：

  10.1002/(sici)1099-0690(200004)2000:8<1623::aid-ejoc1623<3.0.co;2-y
• 作为产物：
  描述：

  车叶草苷 在 吡啶 、 10 wt% Pd(OH)2 on carbon 作用下， 以 乙醇 、 环己烯 为溶剂， 反应 3.0h， 生成 10-deoxygeniposide tetraacetate
  参考文献：
  名称：

  Synthesis of deuterium-labelled substrates for the study of oleuropein biosynthesis inOlea europaeacallus cultures

  摘要：

  We propose the cell culture approach to investigate oleuropein (1) biogenesis in Olea europaea L. We suggest employing olive callus cultures to identify the iridoidic precursor of oleuropein. In fact, we confirmed that callus cells from olive shoot explants are able to produce key secoiridoid as 1. To enable this approach, we synthesised and characterised deuterium-labelled iridoidic precursors belonging both to the loganin and the 8-epiloganin series. These iridoids are [7,8-H-2(2)]-7-deoxy-8-epi-loganin (2(D)), [8,10-H-2(2)]-8-epi-loganin (4(D)) and [7,8-H-2(2)]-7-deoxy-loganin (3(D)).

  DOI：

  10.1080/14786419.2015.1079525

文献信息

• Studies on monoterpene glucosides and related natural products. XLVII. Synthesis of 3H- and 2H-labeled iridodial derivatives for studies on the biosynthesis of iridoid glucosides.
  作者：SHINICHI UESATO、KOJI KOBAYASHI、HIROYUKI INOUYE

  DOI：10.1248/cpb.30.3942

  日期：——

  For studies on the biosynthesis of iridoid glucosides, four labeled compounds, i.e., [10-3H]-iridotrial (4), [10-3H]-7, 8-dehydroiridodial (6), [10-3H]-7, 8-dehydroiridotrial (7) and [10-2H3]-iridodial (3), along with the known [10-3H]-iridodial glucoside (10) and [10-3H]-iridodial (3) were prepared from geniposide (11). Furthermore, [11-2H3]-7, 8-dehydroiridodial (6) was derived from mussaenoside (14).

  为了研究环烯醚萜苷的生物合成，四种标记化合物，即[10-3H]-环烯醚萜醛(4)、[10-3H]-7、8-脱氢环烯醚酮二醛(6)、[10-3H]-7、8 -脱氢鸢尾醛 (7) 和 [10-2H3]-鸢尾醛 (3)，以及已知的 [10-3H]-鸢尾醛葡萄糖苷 (10) 和 [10-3H]-鸢尾醛 (3) 由京尼平苷 (11) 制备。此外，[11-2H3]-7, 8-脱氢环烯二醛(6)衍生自mussaenoside (14)。
• Intermediacy of 6-hydroxyloganin in the ring cleavage course of loganin to secologanin
  作者：Kenichiro Inoue、Takao Tanahashi、Hiroyuki Inouye、Hiroshi Kuwajima、Kiyokazu Takaishi

  DOI：10.1016/0031-9422(89)80263-8

  日期：1989.1

  Abstract A possible biosynthetic pathway from loganin to secologanin through ring cleavage of 6-hydroxyloganin was ruled out in feeding experiments in which Eustoma russellianum , Swertia japonica , Lonicera morrowii and Adina pilulifera were each presented with three C-6 and C-7 stereoisomers of 6-hydroxy [7- 2 H] loganin as well as [6,6,7,8- 2 H 4 ] - and [6,6,7,8 carbomethoxy- 2 H 7 ]-loganin. In

  摘要 在饲喂实验中排除了从马钱素通过 6-羟基马钱素的环裂解到赛洛加宁的可能生物合成途径，其中罗素、獐牙、忍冬和阿迪娜分别具有 6 种 C-6 和 C-7 立体异构体。 -羟基[7- 2 H]马钱素以及[6,6,7,8- 2 H 4 ] - 和[6,6,7,8 甲氧基-2 H 7 ]-马钱素。在相关实验中，导致 seroside 的 secologanin 醛基的还原被证明是通过来自 si 面的氢化物离子攻击进行的。
• Ladroside (= 6?-Caffeoyl-mussaenoside), a New Iridoid Glucoside fromVeronica officinalis L. (Scrophulariaceae) and the elucidation of the absolute configuration at C(8) of mussaenoside
  作者：Fatma�u Afifi-Yazar、Otto Sticher、Shinichi Uesato、Kimiko Nagajima、Hiroyuki Inouye

  DOI：10.1002/hlca.19810640104

  日期：1981.2.4

  A new iridoid glucoside, named ladroside, together with mussaenoside (1) [2], has been isolated from Veronica officinalisL. The structure of ladroside (4) and the identity of mussaenoside have been established by spectral analysis. Additionally, the absolute configuration at C(8) carrying the tertiary hydroxyl group has been established by chemical evidence.

  从Veronica officinalis L中分离出了一种新的鸢尾糖苷，名为ladroside，与mussaenoside （1） [2]分离。通过光谱分析已确定了ladroside （4）的结构和mussaenoside的身份。此外，通过化学证据已经确定了在C（8）上带有叔羟基的绝对构型。
• Biosynthesis of secoiridoid glucosides in oleaceae
  作者：Søren Damtoft、Henrik Franzyk、Søren Rosendal Jensen

  DOI：10.1016/0031-9422(91)80018-v

  日期：1993.11

  and its 7-epimer were obtained, strongly implying that 7-ketologanic acid is an intermediate in the biosynthesis of oleosides. The incorporations were measured by 2 H NMR in several isolated secoiridoids all belonging to the oleosides. In addition, the content of acidic iridoids (both carbocyclic and seco-type) in two additional species of Oleaceae, namely Ligustrum ovalifolium and Phillyrea latifolia

  摘要 油苷类糖苷（油苷）的生物合成已在木犀科的两种植物中进行了研究，即精益白蜡和丁香。制备了脱氧木酸、8-表-脱氧木酸、7-表-脱氧木酸和木糖酸的氘代类似物。在施用上述化合物时，获得了高掺入的脱氧原酸以及原木酸及其 7-差向异构体，这强烈暗示 7-酮基酸是油苷生物合成中的中间体。 . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . 通过 2 H NMR 测量了几种分离的类环烯醚萜烯中的掺入量，这些类环烯脂酸酯均属于油苷。此外，还检测了另外两种木犀科植物 Ligustrum Ollifolium 和 Phillyrea
• Biosynthesis of iridoids in Syringa and Fraxinus: Secoiridoid precursors
  作者：Søren Damtoft、Henrik Franzyk、Søren Rosendal Jensen

  DOI：10.1016/0031-9422(95)00211-o

  日期：1995.10

  Several deuterium-labelled secoiridoids have been prepared and tested as possible precursors for the iridoids in Fraxinus excelsior, Syringa josikaea and S. vulgaris. Oleoside Ii-methyl ester was an efficient precursor for the oleosides, whereas secologanin-type iridoids gave only significant incorporation in 5. josikaea. In this plant low incorporations into the oleosides were also seen for kingiside and 8-epi-kingiside. The major pathway to the oleosides therefore seems to proceed via a direct ring fission of ketologanin to oleoside 11-methyl ester. A Baeyer-Villiger-like mechanism which explains the different compounds found in the plants is proposed, and the taxonomy of the Oleaceae is discussed. Due to the unique presence of the usual pathway leading to secologanin and its congeners in Fontanesia, the Oleaceae is considered to be a member of the Gentiananae rather than Scrophulariales/Lamianae.