gibberellin GA₂₅ trimethyl ester | 31759-09-8

• 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: gibberellin GA₂₅ trimethyl ester
• 英文别名: gibberellin A₂₅ trimethyl ester；gibberellin GA25 trimethyl ester；Gibberellin A(25)-trimethylester；trimethyl (1R,2S,3R,4R,8R,9R,12R)-4-methyl-13-methylidenetetracyclo[10.2.1.01,9.03,8]pentadecane-2,4,8-tricarboxylate
• CAS: 31759-09-8
• 化学式: C₂₃H₃₂O₆
• 分子量: 404.503
• InChiKey: CVVOOYMCPNGYQG-BUYPHVAFSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.4
• 重原子数：
  29
• 可旋转键数：
  6
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.78
• 拓扑面积：
  78.9
• 氢给体数：
  0
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  gibberellin GA₂₅ trimethyl ester 在 吡啶 、 咪唑 、 lithium aluminium tetrahydride 、 硼氘化钠 、 草酰氯 、 二甲基亚砜 、 三乙胺 作用下， 生成 (R)-((1R,4aR,4bR,7R,9aR,10S,10aR)-1,10-bis(((tert-butyldiphenylsilyl)oxy)methyl)-1-methyl-8-methylenedodecahydro-4aH-7,9a-methanobenzo[a]azulen-4a-yl)methyl-d acetate
  参考文献：
  名称：

  Stereochemistry of the oxidation of gibberellin 20-alcohols, GA15 and GA44, to 20-aldehydes by gibberellin 20-oxidases

  摘要：

  (20R)- 和 (20S)-[20- 2 H 1 ]-赤霉素A 15 和一个 44 已用于确定立体化学 赤霉素20-氧化酶催化转化为20-醛。

  DOI：

  10.1039/a606158c
• 作为产物：
  描述：

  gibberellin GA13 7,19,20-trimethyl ester 在 三正丁基氢锡 、 potassium hydride 作用下， 生成 gibberellin GA₂₅ trimethyl ester
  参考文献：
  名称：

  Stereochemistry of the oxidation of gibberellin 20-alcohols, GA15 and GA44, to 20-aldehydes by gibberellin 20-oxidases

  摘要：

  (20R)- 和 (20S)-[20- 2 H 1 ]-赤霉素A 15 和一个 44 已用于确定立体化学 赤霉素20-氧化酶催化转化为20-醛。

  DOI：

  10.1039/a606158c

文献信息

• Fraga, Braulio M.; Gonzalez, Antonio G.; Tellado, Fernando G., Journal of the Chemical Society. Perkin transactions I, 1984, # 5, p. 1109 - 1113
  作者：Fraga, Braulio M.、Gonzalez, Antonio G.、Tellado, Fernando G.、Duri, Zvitendo J.、Hanson, James R.

  DOI：——

  日期：——
• The biotransformation of a gibberellin 20→19-lactone by Gibberella fujikuroi
  作者：Mohammad Shaiq Ali、Carole A. Davis、James R. Hanson

  DOI：10.1016/0031-9422(91)83446-r

  日期：1991.1

  Incubation of ent-7,19-dihydroxygibberell-16-en-20-oic acid 20 --> 19-lactone with Gibberella fujikuroi led to hydroxylation at the 3-alpha- and 19-positions and to oxidation of the 7-alcohol.
• Ward, Jane L.; Gaskin, Paul; Brown, Robert G. S., Journal of the Chemical Society. Perkin Transactions 1 (2001), 2002, vol. 2, # 2, p. 232 - 241
  作者：Ward, Jane L.、Gaskin, Paul、Brown, Robert G. S.、Jackson, Graham S.、Hedden, Peter、Phillips, Andy L.、Willis, Christine L.、Beale, Michael H.

  DOI：——

  日期：——
• Gibberellins in seedlings and flowering trees of Prunus avium L.
  作者：Patrick S. Blake、Gordon Browning、Lynda J. Benjamin、Lewis N. Mander

  DOI：10.1016/s0031-9422(99)00597-x

  日期：2000.2

  Extracts of acids from mature seeds, germinating seeds, first, second and third year seedlings as well as mature, flowering trees of sweet cherry (Prunus avium L. cv. Stella) were analysed by gas chromatography-mass spectrometry. The presence of the known gibberellins (GAs) GA(1) (1), GA(3) (4), GA(5) (7), GA(8) (11), GA(19) (14), GA(20) (12), GA(29) (13), GA(32) (5), GA(85) (2), GA(86) (3) and GA(87) (6) was confirmed by comparison of their mass spectra and Kovats retention indices with those of standards or literature values. In addition, 16 alpha,17-dihydrodihydroxy GA(25) (16) was identified and its stereochemistry confirmed by rational synthesis. The 12 alpha,13-dihydroxy GAs, GA(32) (5), GA(85) (2), GA(86) (3) and GA(87) (6), were detected in mature seeds, germinating seeds and young seedlings, but not in flowering plants. The 13-hydroxy GAs, GA(1) (1) and GA(3) (4), were present in germinating seeds and, in addition to these, GA(5) (7), GA(8) (11), GA(19) (14), GA(20) (12) and GA(29) (13) were detected in seedlings and mature flowering plants. In germinating seeds and seedlings (while the plants were growing actively), concentrations of the 12 alpha,13-dihydroxy GAs, measured by bioassay, declined and those of the 13-hydroxy GAs increased. The results are discussed with reference to the known and predicted effects of the GAs on the vegetative growth and flowering of P. avium plants. (C) 2000 Elsevier Science Ltd. All rights reserved.
• Stereochemistry of the oxidation of gibberellin 20-alcohols, GA15 and GA44, to 20-aldehydes by gibberellin 20-oxidases
  作者：Jane L. Ward、Graham J. Jackson、Michael H. Beale、Paul Gaskin、Peter Hedden、Lewis N. Mander、Andrew L. Phillips、Hideharu Seto、Manuel Talon、Christine L. Willis、Theresa M. Wilson、Jan A. D. Zeevaart

  DOI：10.1039/a606158c

  日期：——

  (20R)- and (20S)-[20- 2 H 1 ]-gibberellins A 15 and A 44 have been used to determine the stereochemistry of the conversion to the 20-aldehyde catalysed by gibberellin 20-oxidases.

  (20R)- 和 (20S)-[20- 2 H 1 ]-赤霉素A 15 和一个 44 已用于确定立体化学 赤霉素20-氧化酶催化转化为20-醛。