1-(2-hydroxy-3,4,6-trimethylphenyl)-1,6-hexanediol | 58186-11-1

• 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: 1-(2-hydroxy-3,4,6-trimethylphenyl)-1,6-hexanediol
• 英文别名: 1-(2'-hydroxy-3',4',6'-trimethylphenyl)-1,6-hexanediol；1-(2-Hydroxy-3,4,6-trimethylphenyl)-1,6-hexandiol；1-(2-hydroxy-3,4,6-trimethylphenyl)hexane-1,6-diol
• CAS: 58186-11-1
• 化学式: C₁₅H₂₄O₃
• 分子量: 252.354
• InChiKey: OSVNAZHUSIZAKH-UHFFFAOYSA-N

物化性质

• 熔点：
  135-136 °C(Solv: ethyl ether (60-29-7))
• 沸点：
  394.3±21.0 °C(Predicted)
• 密度：
  1.091±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.1
• 重原子数：
  18
• 可旋转键数：
  6
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.6
• 拓扑面积：
  60.7
• 氢给体数：
  3
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  1-(2-hydroxy-3,4,6-trimethylphenyl)-1,6-hexanediol 在 吡啶 、 chromium(VI) oxide 、 potassium dihydrogenphosphate 、 potassium nitrososulfonate 、 硫酸 作用下， 生成 2,3,5-trimethyl-6-(6'-acetoxy-1'-oxohexyl)-1,4-benzoquinone
  参考文献：
  名称：

  FR2269333

  摘要：

  公开号：
• 作为产物：
  描述：

  2,3,5-三甲基苯酚 在 lithium aluminium tetrahydride 、 三氯化铝 作用下， 生成 1-(2-hydroxy-3,4,6-trimethylphenyl)-1,6-hexanediol
  参考文献：
  名称：

  FR2269333

  摘要：

  公开号：

文献信息

• Synthesis of quinones having carboxy- and hydroxy-alkyl side chains, and their effects on rat-liver lysosomal membrane.
  作者：KAYOKO OKAMOTO、MASAZUMI WATANABE、MITSURU KAWADA、GIICHI GOTO、YASUKO ASHIDA、KATSUAKI ODA、AKIKO YAJIMA、ISUKE IMADA、HIROSHI MORIMOTO

  DOI：10.1248/cpb.30.2797

  日期：——

  In order to study the structure activity relationship of metabolites of ubiquinone, α-tocopherol and phylloquinone (Ia, b, c, IIa, b, c), 3-carboxy-2-butenyl (IIIa, b, c), 6-hydroxy-3-methyl-2-hexenyl (IVa, b, c), 4-hydroxy-3-methylbutyl (Va, b), 4-hydroxy-3-methyl-2-butenyl (VIb, c), ω-carboxyalkyl (VIIa, b, c), and ω-hydroxyalkyl (VIIIa, b) side chains were introduced into the 6-position of 2, 3-dimethoxy-5-methyl-1, 4-benzoquinone and 2, 3, 5-trimethyl-1, 4-benzoquinone, as well as the 3-position of 2-methyl-1, 4-naphthoquinone. The effects of these quinones on the membrane stability of rat-liver lysosomes and on the activity of bovine heart phosphodiesterase were investigated. A good correlation was observed between these activities of the benzoquinone derivatives (VIIa, b).

  为了研究辅酶Q、α-生育酚和叶绿醌（Ia, b, c, IIa, b, c）的代谢产物结构活性关系，将3-羧基-2-丁烯基（IIIa, b, c）、6-羟基-3-甲基-2-己烯基（IVa, b, c）、4-羟基-3-甲基丁基（Va, b）、4-羟基-3-甲基-2-丁烯基（VIb, c）、ω-羧基烷基（VIIa, b, c）和ω-羟基烷基（VIIIa, b）侧链引入到2, 3-二甲氧基-5-甲基-1, 4-苯醌和2, 3, 5-三甲基-1, 4-苯醌的6-位以及2-甲基-1, 4-萘醌的3-位。研究了这些醌类化合物对大鼠肝脏溶酶体膜稳定性和牛心磷酸二酯酶活性的影响。苯醌衍生物（VIIa, b）的这些活性之间观察到了良好的相关性。
• Aralkyl carboxylic acid compounds
  申请人：Takeda Chemical Industries, Ltd.

  公开号：US04139545A1

  公开（公告）日：1979-02-13

  Novel compounds of the formulae ##STR1## wherein R represents lower alkyl or lower alkoxy, A represents --CH.sub.2 --, --CO-- or ##STR2## n represents an integer of 1 to 8, X represents hydrogen or hydroxyl which may be protected and Y represents hydroxyl which may be protected, and their esters show an excellent action on the lysosomal membranes of cells, and exhibit excellent pharmacological activities such as physiologic host defense control activity, especially immuno-potentiating activity.

  该公式的新化合物为 ##STR1## 其中 R 代表低碳烷基或低碳氧基，A 代表 --CH.sub.2 --，--CO-- 或 ##STR2## n 代表1到8的整数，X 代表氢或羟基，可以被保护，Y 代表羟基，可以被保护，它们的酯对细胞溶酶体膜具有优异作用，并表现出优异的药理活性，如生理宿主防御控制活性，特别是免疫增强活性。
• Aralkyl carboxylic acid compounds in compositions for potentiating
  申请人：Takeda Chemical Industries, Ltd.

  公开号：US04525361A1

  公开（公告）日：1985-06-25

  Novel compounds of the formulae ##STR1## wherein R represents lower alkyl or lower alkoxy, A represents --CH.sub.2 --, --CO-- or ##STR2## n represents an integer of 1 to 8, X represents hydrogen or hydroxyl which may be protected and Y represents hydroxyl which may be protected, and their esters show an excellent action on the lysosomal membranes of cells, and exhibit excellent pharmacological activities such as physiologic host defense control activity, especially immuno-potentiating activity.

  该式的新化合物为 ##STR1## 其中R代表低碳基或低碳氧基，A代表--CH.sub.2 --，--CO--或##STR2## n代表1到8的整数，X代表氢或羟基，可以被保护，Y代表羟基，也可以被保护。它们的酯类对细胞的溶酶体膜具有出色的作用，并表现出出色的药理活性，如生理宿主防御控制活性，特别是免疫增强活性。
• 6-Hydroxy-1,4-benzoquinone compounds
  申请人：Takeda Chemical Industries, Ltd.

  公开号：US04271083A1

  公开（公告）日：1981-06-02

  Novel compounds of the formula ##STR1## wherein R represents lower alkyl or lower alkoxy, A represents --CH.sub.2 --, --CO-- or ##STR2## n represents an integer of 1 to 8, X represents hydrogen or hydroxyl which may be protected and Y represents hydroxyl which may be protected, and their esters show an excellent action on the lysosomal membranes of cells, and exhibit excellent pharmacological activities such as physiologic host defense control activity, especially immuno-potentiating activity.

  本发明涉及一种新的化合物，其化学式为##STR1##其中，R代表较低的烷基或较低的烷氧基，A代表--CH.sub.2 --，--CO--或##STR2## n表示1到8的整数，X代表氢或可被保护的羟基，Y代表可被保护的羟基。这些化合物的酯对细胞的溶酶体膜具有出色的作用，并表现出出色的药理活性，如生理宿主防御控制活性，特别是免疫增强活性。
• 2,3-Dialkoxy-1,4-quinone derivatives; method of producing 1,4-quinone derivatives
  申请人：Takeda Chemical Industries, Ltd.

  公开号：EP0021841A2

  公开（公告）日：1981-01-07

  A compound of the general formula: wherein m is an integer of 10 to 21; R1 is lower alkyl having 1 to 4 carbon atoms; B is a -CH2- or-CO- group, when B is-CH2-, R2 is hydrogen, lower alkyl having 1 to 4 carbon atoms or lower acyl having 1 to 8 carbon atoms, and when B is -CO-, R2 is hydrogen or lower alkyl having 1 to 4 carbon atoms, has pharmaceutical activities such as hypotensive, tissue metabolism stimulating, immunoregulatory, lysosomal membrane stablizing and SRS-A production inhibitory activities and is useful as a heart failure remedy, cerebral circulation disturbance remedy, immunoregulatorand antiallergic drug. A compound of the general formula: [wherein each R3 is lower alkyl having 1 to 4 carbon atoms or lower alkoxy having 1 to 4 carbon atoms, or two R3's taken together represent -CH =CH-CH =CH-; n is O or an integer of 1 to 20 and when n is 1 to 20, A is -CH2-, or -CO- and Z is CH2OH, acyloxymethyl having 2 to 11 carbon atoms, esterified or unesterified carboxyl having 1 to 5 carbon atoms, lower alkoxymethyl having 2 to 5 carbon atoms, silyloxymethyl having 4 to 7 carbon atoms or acetalmethyl having 3 to 8 carbon atoms; when n is O, -A(CH2)n-Z is (wherein - is 0 or an integer of 1 to 12) and Z is H] can be produced with advantage for commercial-scale production by oxidising a compound of the general formula: [wherein X1 or X2 is hydroxyl or amino, with the other being H or an esterified hydroxyl group having 1 to 8 carbon atoms or etherified hydroxyl group having 2 to to 8 carbon atoms; the other symbols are as defined above] with oxygen or air in the presence of a transition metal complex compound.

  通式如下的化合物 其中 m 是 10 至 21 的整数；R1 是具有 1 至 4 个碳原子的低级烷基；当 B 为-CH2-时，R2 为氢、具有 1 至 4 个碳原子的低级烷基或具有 1 至 8 个碳原子的低级酰基；当 B 为-CO-时，R2 为氢或具有 1 至 4 个碳原子的低级烷基、具有降血压、促进组织代谢、免疫调节、稳定溶酶体膜和抑制 SRS-A 生成等药物活性，可用作治疗心力衰竭、脑循环障碍、免疫调节和抗过敏药物。通式如下的化合物 [其中每个 R3 是具有 1 至 4 个碳原子的低级烷基或具有 1 至 4 个碳原子的低级烷氧基，或两个 R3 共同代表-CH =CH-CH =CH-；n 是 O 或 1 至 20 的整数，当 n 为 1 至 20 时，A 是-CH2-、 或-CO-，Z 是 CH2OH、具有 2 至 11 个碳原子的酰氧基甲基、具有 1 至 5 个碳原子的酯化或未酯化羧基、具有 2 至 5 个碳原子的低级烷氧基甲基、具有 4 至 7 个碳原子的硅氧基甲基或具有 3 至 8 个碳原子的乙缩醛甲基；当 n 是 O 时，-A(CH2)n-Z 是 (其中 - 为 0 或 1 至 12 的整数），Z 为 H]，可通过氧化通式如下的化合物生产，具有商业规模生产的优势： [其中 X1 或 X2 为羟基或氨基，另一个为 H 或具有 1 至 8 个碳原子的酯化羟基或具有 2 至 8 个碳原子的醚化羟基；其他符号如上定义]，在过渡金属复合物存在下，与氧气或空气氧化。