5-nonylbenzene-1,3-diol | 46834-36-0

• 物质功能分类: 有机原料 - 烃类化合物及其衍生物 - 芳香烃
• 分子结构分类: 有机化合物 - 苯类化合物 - 酚类
• 英文名称: 5-nonylbenzene-1,3-diol
• 英文别名: 5-Nonylresorcinol
• CAS: 46834-36-0
• 化学式: C₁₅H₂₄O₂
• 分子量: 236.354
• InChiKey: OYXWBGYHDYVIDT-UHFFFAOYSA-N

物化性质

• 熔点：
  72 °C
• 沸点：
  371.0±12.0 °C(Predicted)
• 密度：
  1.007±0.06 g/cm3(Predicted)
• 溶解度：
  可溶于DMSO（少许）、甲醇（少许）

计算性质

• 辛醇/水分配系数(LogP)：
  5.8
• 重原子数：
  17
• 可旋转键数：
  8
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.6
• 拓扑面积：
  40.5
• 氢给体数：
  2
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  5-nonylbenzene-1,3-diol 、 长叶薄荷酮 在 三氯氧磷 、 苯 作用下， 生成 (R)-6,6,9-trimethyl-3-nonyl-7,8,9,10-tetrahydro-6H-benzo[c]chromen-1-ol
  参考文献：
  名称：

  Tetrahydrocannabinol Homologs and Analogs with Marihuana Activity. XIII¹

  摘要：

  DOI：

  10.1021/ja01255a061
• 作为产物：
  描述：

  正辛基镁溴盐 在 三乙基硅烷 、 氢氧化钾 、 三溴化硼 作用下， 以 四氢呋喃 、 二氯甲烷 、 三氟乙酸 为溶剂， 反应 26.0h， 生成 5-nonylbenzene-1,3-diol
  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

文献信息

• MODIFIER FOR AROMATIC POLYESTER AND AROMATIC POLYESTER RESIN COMPOSITION COMPRISING THE SAME
  申请人：TABATA Masayoshi

  公开号：US20110224343A1

  公开（公告）日：2011-09-15

  The present invention provides a modifier for aromatic polyesters which enhances the melt fluidity of aromatic polyesters without a significant decrease in the heat resistance of the aromatic polyesters, and an aromatic polyester resin composition including the modifier for aromatic polyesters. The present invention relates to a modifier for aromatic polyesters comprising polyhydric phenol residues and residues of aromatic polycarboxylic acid, acid halide or acid anhydride thereof, and the modifier comprises a material having a structure composed of a first residue selected from the group consisting of divalent residues represented by Formula (I): —Ar—W 1 x —Ar— and by Formula (II): —Ar—, the first residues being bonded to two identical or different second residues selected from the group consisting of monovalent residues represented by Formula (III): and monovalent residues represented by Formula (IV): —O—C(O)—R 7 —.

  本发明提供了一种用于芳香族聚酯的改性剂，可以增强芳香族聚酯的熔融流动性，而不明显降低芳香族聚酯的耐热性，以及包括该改性剂的芳香族聚酯树脂组合物。本发明涉及一种用于芳香族聚酯的改性剂，包括多羟基酚残基和芳香族多羧酸、酸卤或其酸酐残基，该改性剂包括具有以下结构的材料：第一残基，选择自由式(I)所代表的二价残基：—Ar—W1x—Ar—和自由式(II)所代表的：—Ar—，第一残基与选择自由式(III)所代表的单价残基：和自由式(IV)所代表的单价残基：—O—C(O)—R7—的两个相同或不同的第二残基结合。
• COMPOUNDS HAVING AGONISTIC EFFECT AGAINST GPR84, PREPARATION METHOD FOR COMPOUNDS AND USE OF COMPOUNDS
  申请人：SHANGHAI INSTITUTE OF MATERIA MEDICA, CHINESE ACADEMY OF SCIENCES

  公开号：US20180237399A1

  公开（公告）日：2018-08-23

  The present invention relates to a class of compounds represented by the formula I, or pharmaceutically acceptable salts thereof, methods for their preparation, and application as small molecule tools that function as GPR84 agonists, and their use in preparing a medicament for the treatment of septicemia.

  本发明涉及一类由式I表示的化合物，或其药用可接受盐，其制备方法，以及作为GPR84激动剂的小分子工具的应用，以及它们在制备治疗败血症的药物中的应用。
• Two Novel Alkylresorcinol Synthase Genes from Sorghum; Cloning, Expression, Transformation and Characterization
  申请人：Baerson Scott R.

  公开号：US20110225676A1

  公开（公告）日：2011-09-15

  Sorghum is considered to be an allelopathic crop species, producing phytotoxins such as the lipid benzoquinone sorgoleone (2-hydroxy-5-methoxy-3-[(Z,Z)-8′,11′,14′-pentadecatriene]-p-benzoquinone) which likely accounts for much of its allelopathic properties. Prior investigations into the biosynthesis of sorgoleone have suggested the participation of one or more alkylresorcinol synthases (ARS), which are type III polyketide synthases (PKS) that produce 5-alkylresorcinols using medium to long-chain fatty acyl-CoA starter units via iterative condensations with malonyl-CoA. Current evidence suggests that sorgoleone biosynthesis occurs exclusively in root hair cells, involving the synthesis of a 5-pentadecatrienyl resorcinol intermediate derived from an unusual 16:3 fatty acyl-CoA starter unit. To characterize the enzymes responsible for the biosynthesis of this alkylresorcinol intermediate, a previously-described expressed sequence tag (EST) database prepared from isolated root hairs was first mined for all PKS-like sequences. Quantitative real-time RT-PCR analyses revealed that two of these sequences were preferentially expressed in root hairs, and recombinant enzyme studies demonstrated that both sequences (designated ARS1 and ARS2) encode ARS enzymes capable of accepting a variety of fatty acyl-CoA starter units. Furthermore, RNA interference (RNAi) experiments directed against ARS1 and ARS2 resulted in the generation of multiple independent transformant events exhibiting dramatically reduced sorgoleone levels. Thus, both ARS1 and ARS2 are likely to participate in the biosynthesis of sorgoleone in planta. The sequences of ARS1 and ARS2 were also used to identify several rice genes encoding ARSs, which are likely involved in the production of defense-related alkylresorcinols.

  高粱被认为是一种化感作物，产生植物毒素，如脂肪苯醌sorgoleone（2-羟基-5-甲氧基-3-[(Z，Z)-8'，11'，14'-十五碳烯三烯基]-p-苯醌），这很可能解释了其大部分化感特性。对sorgoleone生物合成的先前研究表明，参与其中的是一种或多种烷基间苯酚合酶（ARS），它们是III型聚酮合酶（PKS），使用中到长链脂肪酰辅酶A起始单元通过与丙酰辅酶A的迭代缩合产生5-烷基间苯酚。目前的证据表明，sorgoleone生物合成仅发生在根毛细胞中，涉及从不寻常的16：3脂肪酰辅酶A起始单元衍生的5-十五碳烯三烯基间苯酚中间体的合成。为了表征负责合成这种烷基间苯酚中间体的酶，首先从分离的根毛制备的已描述表达序列标签（EST）数据库中挖掘所有类似于PKS的序列。定量实时RT-PCR分析表明，其中两个序列在根毛中优先表达，重组酶研究表明这两个序列（称为ARS1和ARS2）编码的ARS酶能够接受各种脂肪酰辅酶A起始单元。此外，针对ARS1和ARS2的RNA干扰（RNAi）实验导致产生多个独立的转化事件，其sorgoleone水平显著降低。因此，ARS1和ARS2都可能参与植物中sorgoleone的生物合成。ARS1和ARS2的序列还用于鉴定编码ARS的几个水稻基因，这些基因可能参与产生与防御相关的烷基间苯酚。
• Efficient Synthesis for Altering Side Chain Length on Cannabinoid Molecules and Their Effects in Chemotherapy and Chemotherapeutic Induced Neuropathic Pain
  作者：Wesley M. Raup-Konsavage、Diana E. Sepulveda、Daniel P. Morris、Shantu Amin、Kent E. Vrana、Nicholas M. Graziane、Dhimant Desai

  DOI：10.3390/biom12121869

  日期：——

  molecules would be based upon cannabigerol (CBG). Because CBG, and its side chain variants, are rapidly converted to other cannabinoids in the plant, there are typically only small amounts in plant extracts, thus prohibiting investigations related to CBG and CBG variant therapeutic effects. (2) Methods: To overcome this, we developed an efficient synthesis of corresponding resorcinol fragments using the

  (1) 背景：最近，在大麻中发现了一些四氢大麻酚和大麻二酚的侧链长度变体；然而，这些分子的前体将基于大麻酚 (CBG)。由于 CBG 及其侧链变体在植物中迅速转化为其他大麻素，因此植物提取物中通常只有少量大麻素，因此禁止与 CBG 和 CBG 变体治疗效果相关的研究。(2) 方法：为了克服这个问题，我们开发了一种使用 Wittig 反应有效合成相应间苯二酚片段的方法，该反应在酸催化下与香叶醇偶联，产生所需的 CBG 侧链变体。然后在化疗引起的神经性疼痛和降低结直肠癌细胞活力的动物模型中测试这些化合物。(3) 结果：我们发现所有侧链变体在剂量为 10 mg/kg 时同样能够减轻小鼠的神经性疼痛。然而，具有较短侧链的分子（即 CBGV 和 CBGB）更能降低结直肠癌细胞的活力。(4) 结论：本文开发的新合成方法将对大麻素、大麻酚、大麻素等其他小类大麻素侧链衍生物的研究具有实用价值。
• Novel insights into the antibacterial activities of cannabinoid biosynthetic intermediate, olivetolic acid, and its alkyl-chain derivatives
  作者：Yuan-E Lee、Takeshi Kodama、Hiroyuki Morita

  DOI：10.1007/s11418-022-01672-9

  日期：2023.3

  revealed that the incorporation of longer alkyl chains to the C-6 position in resorcylic acid conferred antibacterial properties against Staphylococcus aureus and Bacillus subtilis. The resultant olivetolic acid (OA) derivatives with n-undecyl and n-tridecyl side-chains, even those lacking the hydrophobic geranyl moiety from their C-3 positions, exhibited strong antibacterial activities against B. subtilis

  抗菌活性研究表明，在间苯二酚酸的 C-6 位上掺入较长的烷基链赋予了对金黄色葡萄球菌和枯草芽孢杆菌的抗菌特性。所得具有正十一烷基和正十三烷基侧链的橄榄酸 (OA) 衍生物，即使是那些在 C-3 位上缺乏疏水性香叶基部分的衍生物，也对枯草芽孢杆菌表现出很强的抗菌活性，MIC 值为 2.5 μM。此外，研究表明，大麻二酚酸（CBGA）的C-6位正庚基烷基链修饰有效增强了对枯草芽孢杆菌的活性，证明了烷基侧链在调节生物活性中的重要性。总体而言，本研究的结果为进一步评估 OA 和 CBGA 衍生物的抗菌活性以及其他各种生物活性提供了见解，特别是在核心骨架的烷基和异戊二烯基侧链位置优化了疏水性。新药物种子的发现。