5[8′(Z),11′(Z)-pentadecadienyl]resorcinol | 79473-25-9

• 分子结构分类: 有机化合物 - 苯类化合物 - 酚类
• 英文名称: 5[8′(Z),11′(Z)-pentadecadienyl]resorcinol
• 英文别名: [5-(8Z,11Z)-8,11-pentadecadien-1-yl-1,benzenediol]；5-[(8Z,11Z)-pentadeca-8,11-dien-1-yl]resorcinol；cardol (C15:2)；cardol diene；cardol；5-[(8Z,11Z)-pentadeca-8,11-dien-1-yl]benzene-1,3-diol；5-[(8Z,11Z)-pentadeca-8,11-dienyl]benzene-1,3-diol
• CAS: 79473-25-9
• 化学式: C₂₁H₃₂O₂
• 分子量: 316.484
• InChiKey: UFMJCOLGRWKUKO-UTOQUPLUSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  7.4
• 重原子数：
  23
• 可旋转键数：
  12
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.52
• 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：

  乙酸酐 、 5[8′(Z),11′(Z)-pentadecadienyl]resorcinol 在 吡啶 作用下， 反应 24.0h， 生成 Acetic acid 3-acetoxy-5-((8Z,11Z)-pentadeca-8,11-dienyl)-phenyl ester
  参考文献：
  名称：

  Dioxygenation of Long-Chain Alkadien(trien)ylphenols by Soybean Lipoxygenase

  摘要：

  Long-chain alkadien(trien)ylphenols, i.e., cardanols, cardols, and anacardic acids, as well as their acetylated and methylated derivatives were used in enzymatic dioxygenation catalyzed by soybean lipoxygenase-1 (LOX-1). Kinetic studies revealed the influence of functional groups, chain length, number of double bonds, and the distance of the double bonds from the terminal end. Free functional groups were found to be a structural prerequisite for high affinity and turnover number; exceptional kinetic parameters were obtained for omega-6 compounds possessing the same chain length as linoleic acid. The regioselectivity and enantioselectivity of LOX-1 catalysis were investigated with 3-[(Z,Z)-8',11'-pentadecadienyl]phenol as the representative substrate, yielding 3-[12'-(S)-hydroperoxy-(Z,E)-8',10'-pentadecadienyl]phenol as the main product, Our extensive chromatographic and spectroscopic studies comprised HPLC-MS/MS for differentiation of the regioisomers, H-1 NMR spectroscopy for determination of the double-bond configuration, GC-MS to evaluate the enantiomeric excess, and exciton-coupled circular dichroism for determination of the absolute configuration.

  DOI：

  10.1021/jf980196a

文献信息

• Long chain phenols. Part 17. The synthesis of 5-[(Z)-pentadec-8-enyl]resorcinol, ‘cardol monoene,’ and of 5-[(ZZ)-pentadec-8,11-dienyl]-resorcinol dimethyl ether, ‘cardol diene’ dimethyl ether
  作者：Christopher J. Baylis、Stanley W. D. Odle、John H. P. Tyman

  DOI：10.1039/p19810000132

  日期：——

  the bromide and alkylation of lithio-oct-1-yne gave 5-(pentadec-8-ynyl)resorcinol dimethyl ether which was selectively converted into the 8-(Z)-alkene. Demethylation with lithium iodide gave 5-[(Z)-pentadec-8-enyl]resorcinol which was identical to ‘cardol monoene’. Reaction of 7-(3,5-dimethoxyphenyl)heptyl bromide with the lithium derivative of OH-protected propargyl alcohol, gave after acidic treatment

  合成了两种“ cardol”系列中的不饱和化合物，这是一种来自西洋参（Anacardium occidentale）的重要成分酚。3,5-二甲氧基苯甲醛在锂的存在下与OH保护的6-氯己-1-醇相互作用，经过酸处理后生成1-（3,5-二甲氧基苯基）庚烷-1,7-二醇，将其选择性地氢解为7-（3,5-二甲氧基苯基）庚-1-醇。转化为溴化物并进行硫代辛基-1-炔的烷基化，得到5-（十五烷基-8-炔基）间苯二酚二甲醚，其被选择性地转化为8-（Z）-烯烃。用碘化锂脱甲基得到5-[（Z）-十五烷-8-烯基间苯二酚，与“心单烯”相同。7-（3,5-二甲氧基苯基）庚基溴化物与OH保护的炔丙醇的锂衍生物反应，经酸处理后得到10-（3,5-二甲氧基苯基）dec-2-yn-1-ol。用戊-1-炔基溴化镁制得5-戊基-8，11-二炔基间苯二酚二甲醚。选择性氢化得到5-[（ZZ）-pentadeca-8,11-二烯基]间苯二酚二甲醚，与“
• NOVEL NUTRACEUTICAL AND PHARMACEUTICAL COMPOSITIONS AND USE THEREOF FOR THE TREATMENT, CO-TREATMENT OR PREVENTION OF INFLAMMATORY DISORDERS
  申请人：Raederstorff Daniel

  公开号：US20090186942A1

  公开（公告）日：2009-07-23

  The invention relates to novel compositions comprising a phenolic compound as well as to the use of these compositions as a medicament, in particular for the manufacture of a nutraceutical or pharmaceutical composition for the treatment, co-treatment or prevention of inflammatory disorders, such as arthritis, asthma, inflammatory bowel diseases, inflammatory diseases of the skin (e.g., psoriasis, eczema, atopic dermatitis, sunburn) and chronic inflammatory disorders, such as atherosclerosis, heart diseases, metabolic syndrome X, cancer, Alzheimer's disease and pre-stages thereof such as mild cognitive impairment. Also, the invention relates to the use of a cosmetic composition comprising a phenolic compound for the cosmetic treatment, co-treatment or prevention of inflammation of the skin, in particular for the cosmetic treatment, co-treatment or prevention of sunburn or of impure skin.
• NOVEL COMPOSITIONS
  申请人：Raederstorff Daniel

  公开号：US20100055218A1

  公开（公告）日：2010-03-04

  The present invention relates to novel compositions comprising rosehip and at least one additional component e.g. selected from ligustilide, oleuropein (I), oleuropein aglycone (II), hydroxytyrosol, genistein, magnolol, honokiol, magnolia bark extract, cashew fruit extract and Glycyrrhiza foetida as well as to the use of these compositions as a medicament, in particular as a medicament for the treatment, co-treatment or prevention of inflammatory disorders.
• US5202355A
  申请人：——

  公开号：US5202355A

  公开（公告）日：1993-04-13
• [EN] PESTICIDE COMPOSITIONS OF PHENOL AND RESORCINOL DIENES AND TRIENES<br/>[FR] COMPOSITIONS PESTICIDES DE DIÈNES ET DE TRIÈNES DE PHÉNOL ET DE RÉSORCINOL
  申请人：[en]METABOLIC INSIGHTS LTD.

  公开号：WO2022130367A1

  公开（公告）日：2022-06-23

  A composition comprising at least one compound of Formula (I), or an agriculturally acceptable salt thereof as an active pesticidal ingredient is provided. Non-limiting examples of the compounds are Cardol triene, Cardanol triene and Cardol diene. A method for controlling, preventing, reducing or eradicating the instances of plant-pathogen infestation on a plant, plant organ, plant part, or plant propagation material is further provided, the method comprising: applying to a plant, plant part, plant organ or plant propagation material, or to soil surrounding said plant, a pesticidal effective amount of an active agent comprising at least one compound of Formula (I), such as Cardol triene, Cardanol triene and Cardol diene, or a pesticide composition comprising at least one of them, wherein said plant-pathogen is a member selected from: a member of the family Pythiaceae, a member of the class Agaricomycetes, and a member of the order Pseudomonadales. where (II) is a single or double bond, and R1and R2are independently selected from hydrogen and hydroxy group.