3,7,11-trimethyldodec-1,4,6,10-tetraene-3-ol | 1071-89-2

• 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: 3,7,11-trimethyldodec-1,4,6,10-tetraene-3-ol
• 英文别名: 3,7,11-trimethyl-dodeca-1,4,6,10-tetraen-3-ol；(+/-)-4,5-didehydro-nerolidol；3,7,11-Trimethyldodeca-1,4,6,10-tetraen-3-ol；Vinyl-Ψ-jonol
• CAS: 1071-89-2；5208-91-3
• 化学式: C₁₅H₂₄O
• 分子量: 220.355
• InChiKey: UIMSQVVHHIUQOZ-UHFFFAOYSA-N

物化性质

• 沸点：
  88-90 °C(Press: 0.05 Torr)
• 密度：
  0.884±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  4.6
• 重原子数：
  16
• 可旋转键数：
  6
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.47
• 拓扑面积：
  20.2
• 氢给体数：
  1
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  3,7,11-trimethyldodec-1,4,6,10-tetraene-3-ol 在 1,2-环氧丁烷 作用下， 生成 (all-E)-2,7,11,15,19-pentamethyl-eicosa-2,4,6,8,10,14-hexaenal
  参考文献：
  名称：

  Bacterial Carotenoids. XLVIII. Total Syntheses of Carotenes of the 1,2-Dihydro Series.

  摘要：

  The total syntheses of 1,2,7,8,1',2',7',8'-octahydro-psi,psi-carotene (1), 1,2,7,8-tetrahydro-psi,psi-carotene (2), 1,2,1',2'-tetradehydro-psi,psi-carotene (3), 1,2-dihydro-psi,psi-carotene (4), 1,2-dihydor-3,4-didehydro-psi,psi-carotene (5), and 1,2,1',2'-tetrahydro-3,4,3',4'-tetrahydro-psi,psi-carotene (6) are described. The properties of products and intermediates, including the three new apocarotenals 1,2,7,8-tetrahydro-12'-apo-psi-caroten-12'-al (20), 1,2-dihydro-8'-apo-pse-caroten-8'-al (25), and 1,2-dihydro-3,4-didehydro-8'-apo-psi-carotene-8'-al (32), are reported. A fragment ion at M68 on electron impact appears to be characteristic for carotenoids with a 1,2,7,8-tetrahydro end-group.

  DOI：

  10.3891/acta.chem.scand.29b-1015
• 作为产物：
  描述：

  (all-E)-3,7,11-Trimethyldodeca-4,6,10-trien-1-yn-3-ol 在 Lindlar's catalyst 氢气 作用下， 以 Petroleum ether 为溶剂， 生成 3,7,11-trimethyldodec-1,4,6,10-tetraene-3-ol
  参考文献：
  名称：

  类胡萝卜素中的合成物。17.米特隆。γ-胡萝卜素sowie d，升-α-UNDβ胡萝卜素AUS脱氢-β-APO-12'-carotinal（C 25）

  摘要：

  γ-胡萝卜素（mp 153°）通过脱氢-β-apo-l2'-胡萝卜素（C 25）（V）与伪亚亚乙基乙基三苯基氯化chloride（IV）的WITTIG反应合成（C 25 + C 15＝ C 40）或β-apo-8′-胡萝卜素（C 30）（VII）与香叶基三苯基溴化phosph（VIII）（C 30 + C 10＝ C 40）。

  DOI：

  10.1002/hlca.19610440414

文献信息

• PREPARATION METHOD OF 3,7,11- TRIMETHYLDODEC -2,4,6,10-TETRAENE-1-YL-PHOSPHONIC SALT
  申请人：NANJING UNIVERSITY OF TECHNOLOGY

  公开号：US20140378709A1

  公开（公告）日：2014-12-25

  Provided in the present invention is a preparation method for a phosphonic salt, comprising the step of: reacting 3,7,11-trimethyldodec-1,4,6,10-tetraene-3-ol with triarylphosphine and an acid in an alcohol solvent at 50-100° C. to form the phosphonic salt, wherein the acid is a sulfamic acid or methanesulfonic acid, and the alcohol solvent is a straight chain monohydric alcohol containing 1-5 carbon atoms. The method is performed in nearly neutral conditions, greatly reducing the generation of impurities and greatly obtaining phosphonic salt with an increased E content. The yield of lycopene obtained by using the phosphonic salt as a raw material is high.

  本发明提供了一种磷酸盐的制备方法，包括以下步骤：在醇溶剂中，将3,7,11-三甲基十二碳-1,4,6,10-四烯-3-醇与三芳基膦和酸在50-100°C条件下反应，形成磷酸盐，其中酸为磺酰胺酸或甲磺酸，醇溶剂为含有1-5个碳原子的直链一元醇。该方法在几乎中性条件下进行，大大减少了杂质的生成，极大地获得了含量增加的磷酸盐。以该磷酸盐为原料获得的番茄红素产率高。
• Manufacture of symmetrical carotenoids
  申请人：BASF Aktiengesellschaft

  公开号：US04127455A1

  公开（公告）日：1978-11-28

  Symmetrical carotenoids are manufactured from the molecular halves thereof by a process wherein phosphonium salts of the molecular halves of these symmetrical carotenoids are oxidized electrochemically in a solvent and in the presence of a base, causing the molecular halves to dimerize, with elimination of substituted phosphine oxide.

  对称类胡萝卜素是通过一种过程从它们的分子半部分制造的，其中对称类胡萝卜素的分子半部分的磷酸铵盐在溶剂和碱的存在下被电化学氧化，导致分子半部分二聚化，消除了取代的膦氧化物。
• Bacterial Carotenoids. XLVIII. Total Syntheses of Carotenes of the 1,2-Dihydro Series.
  作者：Åse Eidem、Richard Buchecker、Helge Kjøsen、Synnøve Liaaen-Jensen

  DOI：10.3891/acta.chem.scand.29b-1015

  日期：——

  The total syntheses of 1,2,7,8,1',2',7',8'-octahydro-psi,psi-carotene (1), 1,2,7,8-tetrahydro-psi,psi-carotene (2), 1,2,1',2'-tetradehydro-psi,psi-carotene (3), 1,2-dihydro-psi,psi-carotene (4), 1,2-dihydor-3,4-didehydro-psi,psi-carotene (5), and 1,2,1',2'-tetrahydro-3,4,3',4'-tetrahydro-psi,psi-carotene (6) are described. The properties of products and intermediates, including the three new apocarotenals 1,2,7,8-tetrahydro-12'-apo-psi-caroten-12'-al (20), 1,2-dihydro-8'-apo-pse-caroten-8'-al (25), and 1,2-dihydro-3,4-didehydro-8'-apo-psi-carotene-8'-al (32), are reported. A fragment ion at M68 on electron impact appears to be characteristic for carotenoids with a 1,2,7,8-tetrahydro end-group.
• Synthesen in der Carotinoid-Reihe. 17. Mittelung. γ-Carotin sowie<i>d</i>,<i>l</i>-α- und β-Carotin aus Dehydro-β-apo-12′-carotinal(C₂₅)
  作者：R. Rüegg、U. Schwieter、G. Ryser、P. Schudel、O. Isler

  DOI：10.1002/hlca.19610440414

  日期：——

  γ-Carotene (m. p. 153°) has been synthesized by a WITTIG reaction of either dehydro-β-apo-l2′-carotenal(C25) (V) with pseudo-ionylideneethyl-triphenylphosphonium chloride (IV) (C25 + C15 = C40) or of β-apo-8′-carotenal(C30) (VII) with geranyltriphenylphosphonium bromide (VIII) (C30 + C10 = C40).

  γ-胡萝卜素（mp 153°）通过脱氢-β-apo-l2'-胡萝卜素（C 25）（V）与伪亚亚乙基乙基三苯基氯化chloride（IV）的WITTIG反应合成（C 25 + C 15＝ C 40）或β-apo-8′-胡萝卜素（C 30）（VII）与香叶基三苯基溴化phosph（VIII）（C 30 + C 10＝ C 40）。