(2E,4E)-6-hydroxy-5-methylhexa-2,4-dienal | 238759-90-5

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 脂肪酰基
• 英文名称: (2E,4E)-6-hydroxy-5-methylhexa-2,4-dienal
• 英文别名: (2E,4E)-6-hydroxy-5-methyl-2,4-hexadienal
• CAS: 238759-90-5
• 化学式: C₇H₁₀O₂
• 分子量: 126.155
• InChiKey: XDOQWPZVKOEVJN-AOGGBPEJSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.6
• 重原子数：
  9
• 可旋转键数：
  3
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.29
• 拓扑面积：
  37.3
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  (2E,4E)-6-hydroxy-5-methylhexa-2,4-dienal 在 N-溴代丁二酰亚胺(NBS) 、 二甲基硫 作用下， 以 二氯甲烷 、 乙酸乙酯 为溶剂， 反应 43.0h， 生成 [(2E,4E)-2-methyl-6-oxohexa-2,4-dienyl]triphenylphosphonium bromide
  参考文献：
  名称：

  Synthesis of Bixin and Three Minor Carotenoids from Annatto (Bixa orellana)

  摘要：

  The three apocarotenoids methyl (9Z)-8'-oxo-6,8'-diapocaroten-6-oate (2), methyl (9Z)-10'-oxo-6,10'diapocaroten-6-oate (4). and methyl (9Z)-14'-oxo-6,14'-diapocaroten-6-oate (5), recently isolated from annatto, were synthesized. The key step of all three syntheses was the Wittig reaction of the (Z)-terminus 6 with the phosphonium salts 15, 18, and 24, carrying the polyene chain. Bixin (1) was synthesized from 2 in a Horner-Emmons reaction.

  DOI：

  10.1002/(sici)1522-2675(19990505)82:5<696::aid-hlca696>3.0.co;2-x
• 作为产物：
  描述：

  2-methyl-4-oxobut-2-enoic acid ethyl ester 在 sodium hydride 、 二异丁基氢化铝 作用下， 以 四氢呋喃 、 正己烷 为溶剂， 反应 1.0h， 生成 (2E,4E)-6-hydroxy-5-methylhexa-2,4-dienal
  参考文献：
  名称：

  Synthesis of Bixin and Three Minor Carotenoids from Annatto (Bixa orellana)

  摘要：

  The three apocarotenoids methyl (9Z)-8'-oxo-6,8'-diapocaroten-6-oate (2), methyl (9Z)-10'-oxo-6,10'diapocaroten-6-oate (4). and methyl (9Z)-14'-oxo-6,14'-diapocaroten-6-oate (5), recently isolated from annatto, were synthesized. The key step of all three syntheses was the Wittig reaction of the (Z)-terminus 6 with the phosphonium salts 15, 18, and 24, carrying the polyene chain. Bixin (1) was synthesized from 2 in a Horner-Emmons reaction.

  DOI：

  10.1002/(sici)1522-2675(19990505)82:5<696::aid-hlca696>3.0.co;2-x

文献信息

• New apocarotenoids and β-carotene cleavage in Blakeslea trispora
  作者：Alejandro F. Barrero、M. Mar Herrador、Pilar Arteaga、Jesús Gil、Jose-Antonio González、Eugenio Alcalde、Enrique Cerdá-Olmedo

  DOI：10.1039/c1ob05712j

  日期：——

  Mixed cultures of strains of opposite sex (“mated” cultures) of Blakeslea trispora contain trisporic acids and other apocarotenoids, some of which mediate the sexual responses of this fungus and other Mucorales. In mated cultures of the wild-type strains F986 and F921 we identified eleven apocarotenoids: two C18 trisporoids, three C15 compounds with a monocyclofarnesane skeleton, a C13 compound, and five C7 compounds with a 2-methylhexane skeleton. Six of them are new natural products and two others are new for Blakeslea. Their structures were established by NMR and mass spectra and those of the C7 and C13 compounds were confirmed by chemical synthesis. The finding of these compounds and the presence of approximately equimolecular amounts of the C18, C15, and C7 families led to the conclusion that β-carotene is initially split in three fragments by cleavage of its 13,14 and 11′,12′ double bonds.

  Blakeslea trispora的异性菌株混合培养物（"交配培养物"）中含有三孢子酸和其他类胡萝卜素，其中一些类胡萝卜素介导了这种真菌和其他真菌的性反应。在野生型菌株 F986 和 F921 的交配培养物中，我们发现了 11 种类胡萝卜素：2 种 C18 三孢子酸、3 种以单环法呢烷为骨架的 C15 化合物、1 种 C13 化合物和 5 种以 2-甲基己烷为骨架的 C7 化合物。其中 6 个是新的天然产物，另外 2 个是新的 Blakeslea 天然产物。通过核磁共振和质谱确定了它们的结构，并通过化学合成确认了 C7 和 C13 化合物的结构。这些化合物的发现以及 C18、C15 和 C7 家族近似等分子量的存在，使我们得出结论：δ-胡萝卜素最初是通过裂解其 13、14 和 11â²,12â² 双键而分裂成三个片段的。
• Synthesis of Bixin and Three Minor Carotenoids from Annatto (Bixa orellana)
  作者：Adrian Häberli、Hanspeter Pfander

  DOI：10.1002/(sici)1522-2675(19990505)82:5<696::aid-hlca696>3.0.co;2-x

  日期：1999.5.5

  The three apocarotenoids methyl (9Z)-8'-oxo-6,8'-diapocaroten-6-oate (2), methyl (9Z)-10'-oxo-6,10'diapocaroten-6-oate (4). and methyl (9Z)-14'-oxo-6,14'-diapocaroten-6-oate (5), recently isolated from annatto, were synthesized. The key step of all three syntheses was the Wittig reaction of the (Z)-terminus 6 with the phosphonium salts 15, 18, and 24, carrying the polyene chain. Bixin (1) was synthesized from 2 in a Horner-Emmons reaction.