hexyl-2,4-dihydroxy-6-methyl benzoate | 31581-31-4

• 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: hexyl-2,4-dihydroxy-6-methyl benzoate
• 英文别名: n-hexyl orsellinate；2,4-dihydroxy-6-methyl-benzoic acid hexyl ester；2,4-Dihydroxy-6-methyl-benzoesaeure-hexylester；Hexyl 2,4-dihydroxy-6-methylbenzoate
• CAS: 31581-31-4
• 化学式: C₁₄H₂₀O₄
• 分子量: 252.31
• InChiKey: LKBGRTDVYIFFSP-UHFFFAOYSA-N

物化性质

• 沸点：
  397.6±22.0 °C(Predicted)
• 密度：
  1.131±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  4.3
• 重原子数：
  18
• 可旋转键数：
  7
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  66.8
• 氢给体数：
  2
• 氢受体数：
  4

反应信息

• 作为产物：
  描述：

  红粉苔酸 、 正己醇 生成 hexyl-2,4-dihydroxy-6-methyl benzoate
  参考文献：
  名称：

  高粱酸酯对蘑菇酪氨酸酶活性的抑制作用。

  摘要：

  已经提出了酪氨酸酶抑制剂在制药，食品生物加工和环境工业中的几种应用。但是，已知只有少数化合物可作为有效的酪氨酸酶抑制剂。这项研究评估了间苯二酚（1），蓖麻酚（2）柠檬酸（3）和该酸的衍生物（4-15）的酪氨酸酶相关活性。从酒精中分离出来的lecanoric acid（3）是从地衣Parmotrema tinctorum中分离得到的一种生成物，生成奥来酸（2,4-dihydroxy-6-methylbenzoic acid）（4）和奥山酸酯（2,4-dihydroxy-6-methyl benzoates） ）（5-15）。在0.50 mM时，甲基（5），乙基（6），正丙基（7），叔丁基（11）和正十六烷基山梨酸酯（15）充当酪氨酸酶激活剂，而正丁基（8）则是酪氨酸酶激活剂。丙基（9），仲丁基（10），正戊基（12），正己基（13）和山梨酸正辛酯（14）充当抑制剂。

  DOI：

  10.1248/cpb.c17-00502

文献信息

• Antimycobacterial activity of lichen substances
  作者：N.K. Honda、F.R. Pavan、R.G. Coelho、S.R. de Andrade Leite、A.C. Micheletti、T.I.B. Lopes、M.Y. Misutsu、A. Beatriz、R.L. Brum、C.Q.F. Leite

  DOI：10.1016/j.phymed.2009.07.018

  日期：2010.4

  We describe here the extraction and identification of several classes of phenolic compounds from the lichens Parmotrema dilatatum (Vain.) Hale, Parmotrema tinctorum (Nyl.) Hale, Pseudoparmelia sphaerospora (Nyl.) Hale and Usnea subcavata (Motyka) and determined their anti-tubercular activity. The depsides (atranorin, diffractaic and lecanoric acids), depsidones (protocetraric, salazinic, hypostictic and norstictic acids), xanthones (lichexanthone and secalonic acid), and usnic acid, as well seven orsellinic acid esters, five salazinic acid 8',9'-O-alkyl derivatives and four lichexanthone derivatives, were evaluated for their activity against Mycobacterium tuberculosis. Diffractaic acid was the most active compound (MIC value 15.6 mu g/ml, 41.6 mu M), followed by norstictic acid (MIC value 62.5 mu g/ml, 168 mu M) and usnic acid (MIC value 62.5 mu g/ml, 182 mu M). Hypostictic acid (MIC value 94.0 mu g/ml, 251 mu M) and protocetraric acid (MIC value 125 mu g/ml, 334 mu M) showed moderate inhibitory activity. The other compounds showed lower inhibitory activity on the growth of M. tuberculosis, varying from MIC values of 250 to 1370 mu M. (C) 2009 Elsevier GmbH. All rights reserved.
• Assembly of Melleolide Antibiotics Involves a Polyketide Synthase with Cross-Coupling Activity
  作者：Gerald Lackner、Markus Bohnert、Jonas Wick、Dirk Hoffmeister

  DOI：10.1016/j.chembiol.2013.07.009

  日期：2013.9

  Little is known about polyketide biosynthesis in mushrooms (basidiomycota). In this study, we investigated the iterative type I polyketide synthase (PKS) ArmB of the tree pathogen Armillaria mellea, a producer of cytotoxic melleolides (i.e., polyketides esterified with various sesquiterpene alcohols). Heterologously produced ArmB showed orsellinic acid (OA) synthase activity in vitro. Further, we demonstrate cross-coupling activity of Arm B, which forms OA esters with various alcohols. Using a tricyclic Armillaria sesquiterpene alcohol, we reconstituted the biosynthesis of melledonol. Intermolecular transesterification reactions may represent a general mechanism of fungal PKSs to create structural diversity of small molecules. Phylogenetic network construction of thioesterase domains of both basidiomycetes and ascomycetes suggests that the fungal nonreducing PKS family has likely evolved from an ancient OA synthase and has gained versatility by adopting Claisen-like cyclase or transferase activity.
• The relationship between respiration and chip color during long-term storage of potato tubers
  作者：L. J. Copp、R. W. Blenkinsop、R. Y. Yada、A. G. Marangoni

  DOI：10.1007/bf02853948

  日期：2000.9

  Processing potatoes, both sprout inhibited and untreated, were evaluated for respiration rate and chip color during storage under commercial conditions (12 C, approximately 95% relative humidity, in darkness) following three growing seasons, While absolute respiration rates varied depending upon growing season and treatment, all cultivars and treatments studied during the 1995, 1996, and 1997 storage seasons showed similar respiration profiles. The initial stage following curing and sprout inhibition treatment (if applied) showed essentially constant respiration rates for a period of time varying from two to 15 weeks, depending upon growing season, treatment and cultivar. This was followed by a stage that showed a linear increase in respiration rates. In some cases the respiration rates eventually stabilized, or decreased. There was an apparent correlation between respiration trends and chip color changes in most cases, though the statistical significance varied between cultivars and seasons, Qualitative analysis of the data showed, that the point at which respiration rates began to increase coincided with the onset of the decline in chip color quality. These trends suggest that measurement of tuber respiration may provide a non-destructive and in situ method to predict changes in processing quality of stored potato tubers.