1,3-dimethoxyphenol-5-nonadecylbenzene | 96215-83-7

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: 1,3-dimethoxyphenol-5-nonadecylbenzene
• 英文别名: 1,3-dimethoxy-5-nonadecylbenzene；5-Nonadecyl-resorcin-dimethylether；1,3-Dimethoxy-5-nonadecyl-benzol
• CAS: 96215-83-7
• 化学式: C₂₇H₄₈O₂
• 分子量: 404.677
• InChiKey: KAZMFRNXHYCSAT-UHFFFAOYSA-N

物化性质

• 沸点：
  498.2±25.0 °C(Predicted)
• 密度：
  0.897±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  11.9
• 重原子数：
  29
• 可旋转键数：
  20
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.78
• 拓扑面积：
  18.5
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  1,3-dimethoxyphenol-5-nonadecylbenzene 在 三溴化硼 作用下， 以 二氯甲烷 为溶剂， 以44%的产率得到5-十九烷基间苯二酚
  参考文献：
  名称：

  A cytotoxic constituent of Lysimachia japonica Thunb. (Primulaceae) and the structure-activity relationships of related compounds.

  摘要：

  从 Lysimachia japonica THUNB.（报春花科）中分离出一种具有细胞毒性的烷基间苯二酚，并确定其为 grevillol (2)。(体外测试了它对 KB、B-16、PC-13、L-5178Y、P-388 和 HEp-2 细胞的细胞毒性。还测试了合成的相关化合物对 KB 细胞系的细胞毒性，并讨论了其结构-活性关系。

  DOI：

  10.1248/cpb.37.2431
• 作为产物：
  描述：

  3,5-二甲氧基苯甲醛 在 palladium on activated charcoal 氢气 作用下， 以 水 为溶剂， 生成 1,3-dimethoxyphenol-5-nonadecylbenzene
  参考文献：
  名称：

  Cereal grain resorcinolic lipids: mono and dienoic homologues are present in rye grains

  摘要：

  Analyses (UV, IR, H-1-NMR, MS) of the main phenolic fractions isolated by sequential separation on normal-phase and by argentation chromatography on silica gel confirmed the presence of monoenoic and dienoic homologues of 1,3-dihydroxy-5-n-alkylbenzene in acetone extracts from rye grains. Conversion of mono and dienoic homologue dimethyl ethers to the cis-diols with osmium tetroxide, transformation of the diol to the acetonide with acetone and subsequent MS analysis of resulting derivatives showed that the breakdown pattern for the monoenoic homologues was consistent with a double bond in all the homologous chain length at the 8-position. For dienes, the results were not so conclusive, although the 8- and 11-positions appear to be the favoured ones. It has been also shown that rye 5-n-ketoalkylresorcinols contain a previously unobserved C17 homologue. All identifications were confirmed by comparison with synthetically obtained C19:0 and C21:0 5-n-alkylresorcinols and a 5-n-(2-keto-heptadecyl)resorcinol. Other minor phenolic components present in the acetone extract were identified as homologous 5-n-(2-hydroxyalkyl)resorcinols.

  DOI：

  10.1016/0009-3084(95)02480-7

文献信息

• A cytotoxic constituent of Lysimachia japonica Thunb. (Primulaceae) and the structure-activity relationships of related compounds.
  作者：Munehisa ARISAWA、Kazunob OHMURA、Akio KOBAYASHI、Naokata MORITA

  DOI：10.1248/cpb.37.2431

  日期：——

  A cytotoxic alkylresorcinol was isolated from Lysimachia japonica THUNB. (Primulaceae) and identified as grevillol (2). t was tested for cytotoxicity against KB, B-16, PC-13, L-5178Y, P-388, and HEp-2 cells in vitro. Synthetic related compounds were also tested for cytotoxicity against the KB cell line, and the structure-activity relationships are discussed.

  从 Lysimachia japonica THUNB.（报春花科）中分离出一种具有细胞毒性的烷基间苯二酚，并确定其为 grevillol (2)。(体外测试了它对 KB、B-16、PC-13、L-5178Y、P-388 和 HEp-2 细胞的细胞毒性。还测试了合成的相关化合物对 KB 细胞系的细胞毒性，并讨论了其结构-活性关系。
• Very long chain alkylresorcinols accumulate in the intracuticular wax of rye (Secale cereale L.) leaves near the tissue surface
  作者：Xiufeng Ji、Reinhard Jetter

  DOI：10.1016/j.phytochem.2007.12.008

  日期：2008.3

  members of the Poaceae, likely at or near the surface of various organs. Here, we investigated AR localization within the cuticular wax layers of rye (Secale cereale) leaves. The total wax mixture from both sides of the leaves was found to contain primary alcohols (71%), alkyl esters (11%), aldehydes (5%), and small amounts (<3%) of alkanes, steroids, secondary alcohols, fatty acids and unknowns. A homologous

  烷基间苯二酚 (AR) 是一种生物活性化合物，存在于禾本科的许多成员中，可能位于或靠近各种器官的表面。在这里，我们研究了黑麦 (Secale creame) 叶子的角质层蜡层内的 AR 定位。发现叶子两侧的总蜡混合物含有伯醇 (71%)、烷基酯 (11%)、醛 (5%) 和少量 (<3%) 烷烃、类固醇、仲醇、脂肪酸和未知物。通过 GC-MS 并与十九烷基间苯二酚的合成标准品进行比较，确定了一系列同源的 AR（3%）。蜡 AR 的烷基侧链含有奇数个碳，范围从 C19 到 C27，普遍存在 C21、C23 和 C25。叶子两侧的蜡，在第二个实验中分别分析，包含具有相似相对量和相似同源模式的相同化合物类别。最后，从叶的背面分别对表皮和表皮内蜡层取样。虽然 AR 占角质层内蜡的 2%，但在角质层外蜡中检测不到它们。皮内蜡也略微富含类固醇，而表皮层含有更多的伯醇。所有其他蜡成分均匀分布在两个蜡层之
• Wheat Bran Phenols¹
  作者：Ernest Wenkert、Eva-Marie Loeser、Shiba N. Mahapatra、Fausto Schenker、Edward M. Wilson

  DOI：10.1021/jo01025a046

  日期：1964.2
• Properties of mixed monolayers and bilayers of long-chain 5-n-alkylresorcinols and dipalmitoylphosphatidylcholine
  作者：Sabine Gerdon、Stefan Hoffmann、Alfred Blume

  DOI：10.1016/0009-3084(94)90074-4

  日期：1994.5

  5-n-Alkylresorcinols with different chain length are known to occur in different plants and procaryonts, for example in the cysts of the Azotobacter genus. To study the monolayer and bilayer behaviour of these amphiphilic compounds, we synthesized three analogues with different chain length, namely 5-n-octadecylresorcinol (18AR), 5-n-nonadecylresorcinol(19AR) and 5-n-heneicosylresorcinol (21AR). The pure alkylresorcinols form stable monolayers, 18AR and 19AR, show a phase transition from a liquid-condensed to a liquid-expanded state at temperatures between 20 and 40 degrees C and at lateral pressures below 15 dyn/cm. In mixtures with dipalmitoylphosphatidylcholine (DPPC), monolayer isobars at higher lateral pressures (20-30 dyn/cm) show an increase in the transition temperature to values greater than 50 degrees C for the liquid-condensed to liquid-expanded state of DPPC when the alkylresorcinol content is increased. Particularly in the liquid-expanded state, alkylresorcinols show a strong condensing effect on DPPC monolayers. 18AR/DPPC monolayers at a pressure of 5 dyn/cm show indications of an azeotropic behaviour. A similar increase in transition temperature is observed by differential scanning calorimetry (DSC) and differential scanning densitometry (DSD) in DPPC/alkylresorcinol bilayers. The transition enthalpy decreases with increasing alkylresorcinol content. All alkylresorcinols seem to be completely miscible with DPPC up to at least 50 mol%. The DSD data indicate a slight condensing effect of the alkylresorcinols on the liquid-crystalline phase of DPPC.
• Hiramoto, Yakugaku Zasshi/Journal of the Pharmaceutical Society of Japan, 1942, vol. 62, p. 464
  作者：Hiramoto

  DOI：——

  日期：——