shikimic acid | 191795-38-7

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: shikimic acid
• 英文别名: L-shikimic acid；(3S,4R,5R)-3,4,5-trihydroxycyclohex-1-enecarboxylic acid；(+)-5-epi-shikimic acid；(3S,4R,5R)-3,4,5-trihydroxycyclohexene-1-carboxylic acid
• CAS: 191795-38-7
• 化学式: C₇H₁₀O₅
• 分子量: 174.153
• InChiKey: JXOHGGNKMLTUBP-JKUQZMGJSA-N

物化性质

• 沸点：
  400.5±45.0 °C(Predicted)
• 密度：
  1.725±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  -1.7
• 重原子数：
  12
• 可旋转键数：
  1
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.57
• 拓扑面积：
  98
• 氢给体数：
  4
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  2-氯-4,4,5,5-四甲基-1,3,2-二氧磷杂环戊烷 、 shikimic acid 在 chromium(III) acetylacetonate 作用下， 以 氘代吡啶 、 氘代氯仿 、 环己醇 为溶剂， 反应 0.5h， 生成 (3S,4R,5R)-3,4,5-Tris-(4,4,5,5-tetramethyl-[1,3,2]dioxaphospholan-2-yloxy)-cyclohex-1-enecarboxylic acid 4,4,5,5-tetramethyl-[1,3,2]dioxaphospholan-2-yl ester
  参考文献：
  名称：

  ³¹P NUCLEAR MAGNETIC RESONANCE SPECTROSCOPY OF POLYPHENOL-CONTAINING OLIVE OIL MODEL COMPOUNDS

  摘要：

  Phosphitylation of the free hydroxyl and carboxyl groups of a series of polyphenol-containing olive oil model compounds with 2-chloro-4,4,5,5-tetramethyl-dioxaphospholane allows their classification on the basis of P-31 NMR chemical shifts. Unambiguous assignment of the P-31 NMR chemical shifts of the dihydroxy- and polyhydroxy-phenols has been achieved by employing one and two-dimensional NMR techniques. Furthermore, integration of the appropriate signals of the hydroxyl derivatives in the corresponding P-31 NMR spectra allows the quantification of these compounds. This study forms the basis for the development of a novel and sensitive method that can be used to obtain valuable information about polyphenols that are present in olive oils.

  DOI：

  10.1080/10426500108040591
• 作为产物：
  描述：

  ethyl (3S,4S,5R)-3-acetoxy-5-benzoyloxy-4-(methylsulfonyloxy)cyclohex-1-enecarboxylate 在 4-二甲氨基吡啶 、 氢溴酸 、 potassium acetate 、 sodium hydride 、 对甲苯磺酸 、 溶剂黄146 、 三乙胺 、 sodium hydroxide 作用下， 以 甲醇 、 乙醇 、 二氯甲烷 、 乙酸乙酯 、 异丙醇 为溶剂， 反应 63.17h， 生成 shikimic acid
  参考文献：
  名称：

  (-)-莽草酸的所有立体异构体的立体发散合成：开发各种多羟基-环己烯（或-环己烯）生物活性分子的手性池

  摘要：

  (-)-莽草酸[(-)-SA 1 ]是来自中国八角的天然丰富产物。所有七种立体异构体 [i. e. (+) -ent -SA ent - 1 , (-)-3- epi -SA 2 , (+)-3- epi - ent -SA ent - 2 , (-)-4- epi -SA 3 , (+ )-4- epi - ent -SA ent - 3 , (−)-5- epi -SA 4和 (+)-5- epi - ent -SA ent - 4] 已从 (-)-SA 1系统合成。

  DOI：

  10.1002/ejoc.202100653

文献信息

• Enantioselective synthesis of (+)-shikimic acid and (+)-5-epi-shikimic acid by asymmetric Diels-Alder reaction of (S)-α-sulfinylacrylates
  作者：Javier Adrio、Juan C. Carretero、Jose L. García Ruano、Luisa M. Martín Cabrejas

  DOI：10.1016/s0957-4166(97)00151-1

  日期：1997.5

  Enantiopure (S) benzyl and t-butyl 2-p-tolylsulfinylpropenoates (1 and 2) were readily prepared by Mannich condensation of (R) p-tolylsulfinylacetates (CH2O+Me2NH), followed by in situ nitrogen quaternization. These new chiral dienophiles reacted with furan at high pressures (4-13 Kbar) at rt to afford mainly a 2:1 mixture of both endo adducts (endo-B+endo-A). Enantiopure endo-4B and endo-4A were stereoselectively transformed into (+)-shikimic acid and (+)-5-epi-shikimic acid respectively, by dihydroxylation of the double bond, removal of the sulfinyl group, basic opening of the oxabicyclic skeleton and hydrolysis of the ester moiety. (C) 1997 Elsevier Science Ltd.
• A concise route to (−)-shikimic acid and (−)-5-epi-shikimic acid, and their enantiomers via Barbier reaction and ring-closing metathesis
  作者：Pavan K. Kancharla、Venkata Ramana Doddi、Hariprasad Kokatla、Yashwant D. Vankar

  DOI：10.1016/j.tetlet.2009.09.111

  日期：2009.12

  A simple route for the synthesis of naturally occurring (-)-shikimic acid, (-)-5-epi-shikimic acid, and their enantiomers from D-ribose-derived enantiomeric aldehydes 8a and 8b by employing Barbier reaction and ring-closing metathesis as key steps has been developed. (C) 2009 Elsevier Ltd. All rights reserved.
• ³¹P NUCLEAR MAGNETIC RESONANCE SPECTROSCOPY OF POLYPHENOL-CONTAINING OLIVE OIL MODEL COMPOUNDS
  作者：Stella Christophoridou、Apostolos Spyros、Photis Dais

  DOI：10.1080/10426500108040591

  日期：2001.3.1

  Phosphitylation of the free hydroxyl and carboxyl groups of a series of polyphenol-containing olive oil model compounds with 2-chloro-4,4,5,5-tetramethyl-dioxaphospholane allows their classification on the basis of P-31 NMR chemical shifts. Unambiguous assignment of the P-31 NMR chemical shifts of the dihydroxy- and polyhydroxy-phenols has been achieved by employing one and two-dimensional NMR techniques. Furthermore, integration of the appropriate signals of the hydroxyl derivatives in the corresponding P-31 NMR spectra allows the quantification of these compounds. This study forms the basis for the development of a novel and sensitive method that can be used to obtain valuable information about polyphenols that are present in olive oils.
• Stereodivergent Syntheses of All Stereoisomers of (−)‐Shikimic Acid: Development of a Chiral Pool for the Diverse Polyhydroxy‐cyclohexenoid (or ‐cyclohexanoid) Bioactive Molecules
  作者：Yun‐Gang He、Yong‐Kang Huang、Zhang‐Li Xu、Wen‐Jing Xie、Yong‐Qiang Luo、Feng‐Lei Li、Xing‐Liang Zhu、Xiao‐Xin Shi

  DOI：10.1002/ejoc.202100653

  日期：2021.8.13

  (−)-Shikimic acid [(−)-SA 1] is a naturally-abundant product from Chinese star anise. All of the seven stereoisomers [i. e. (+)-ent-SA ent-1, (−)-3-epi-SA 2, (+)-3-epi-ent-SA ent-2, (−)-4-epi-SA 3, (+)-4-epi-ent-SA ent-3, (−)-5-epi-SA 4 and (+)-5-epi-ent-SA ent-4] have been systematically synthesized from (−)-SA 1.

  (-)-莽草酸[(-)-SA 1 ]是来自中国八角的天然丰富产物。所有七种立体异构体 [i. e. (+) -ent -SA ent - 1 , (-)-3- epi -SA 2 , (+)-3- epi - ent -SA ent - 2 , (-)-4- epi -SA 3 , (+ )-4- epi - ent -SA ent - 3 , (−)-5- epi -SA 4和 (+)-5- epi - ent -SA ent - 4] 已从 (-)-SA 1系统合成。