α-Tetradecyl-β-hydroxy-stearinsaeure | 70774-95-7

• 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: α-Tetradecyl-β-hydroxy-stearinsaeure
• 英文别名: corynomycolic acid；3-hydroxy-2-n-tetradecyl-octadecanoic acid；3-hydroxy-2-tetradecyloctadecanoic acid；3-Hydroxy-2-tetradecyloctadecansaeure
• CAS: 70774-95-7
• 化学式: C₃₂H₆₄O₃
• 分子量: 496.858
• InChiKey: CUEQHYJSSUSIFI-UHFFFAOYSA-N

物化性质

• 沸点：
  596.7±33.0 °C(Predicted)
• 密度：
  0.903±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  14.3
• 重原子数：
  35
• 可旋转键数：
  29
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.97
• 拓扑面积：
  57.5
• 氢给体数：
  2
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  α-Tetradecyl-β-hydroxy-stearinsaeure 生成 N-(3-hydroxy-2-tetradecyloctadecanoyloxy)succinimide
  参考文献：
  名称：

  Lethal and adjuvant activities of cord factor (trehalose-6,6'-dimycolate) and synthetic analogs in mice.

  摘要：

  分枝杆菌糖脂，曲哈洛糖-6，6'-二甲氧基酸酯（TDM）及其类似物，6，6'-二-O-三碳酰基-α，α-曲哈洛糖[TD (L30)]，6，6'-双-O-(2-十四烷基十六烷酰基)-α、6，6'-双-O-(3-羟基-2-十四烷基十八烷酰基)-α，α-三卤糖[TD-(B30)]，6，6'-双-O-(2-二十二烷基-3-羟基二十六烷酰基)-α、6，6'-双-O-(2-二十二烷基-3-羟基二十六烷酰)-α，α-三卤糖[TD (BH48)]，6，6'-双-O-(3-十四烷酰氧基-十四烷酰)-α，α-三卤糖[TD (D28)]，6，6'-双脱氧-6，6'-双(霉菌酰氨基)-α，α-三卤糖[TDNM]和 6、合成了 6, 6'-dideoxy-6, 6'-bis (3-hydroxy-2-tetradecyloctadecanoylamino)-α, α-trehalose[TDN（BH32）]，并检测了它们的致死活性和佐剂活性。当小鼠静脉注射剂量为 150 μg 的 9% 水包油型乳剂时，TDM 和 TDNM 具有致死性，但在相同剂量下，其他类似物对小鼠无致死毒性。腹腔注射 TDM 及其合成类似物可增强小鼠腹腔巨噬细胞对肿瘤细胞的细胞溶解活性。TDM 和 TD (BH32) 还能激发 BALB/c 小鼠对仙台病毒感染的非特异性宿主抵抗力。

  DOI：

  10.1248/cpb.33.4544
• 作为产物：
  描述：

  α-Tetradecyl-β-keto-stearinsaeureethylester 在 氢氧化钾 、 sodium tetrahydroborate 作用下， 以 乙醇 、 水 为溶剂， 反应 2.0h， 生成 α-Tetradecyl-β-hydroxy-stearinsaeure
  参考文献：
  名称：

  Dobner, Bodo; Nuhn, Peter; Buege, Axel, Zeitschrift für Chemie, 1988, vol. 28, # 8, p. 299 - 300

  摘要：

  DOI：

文献信息

• Trehalose derivatives
  申请人：Sawai Pharmaceutical Co., Ltd.

  公开号：US05049664A1

  公开（公告）日：1991-09-17

  A trehalose derivative of the formula: ##STR1## wherein one, two, three or four of R.sup.1, R.sup.2, R.sup.3, R.sup.4, R.sup.5, R.sup.6, R.sup.7 and R.sup.8 are independently selected from the group consisting of C.sub.1-40 aliphatic acyl groups and all the rest of them are hydrogen atoms, with the proviso that: a) when one of them is C.sub.1-40 aliphatic acyl group, then it is not 2-palmitoyl or 6-aliphatic acyl, b) when two of them are C.sub.1-40 aliphatic acyl groups, then they are not located at corresponding positions with each other, c) when three of them are C.sub.1-40 aliphatic acyl groups, then they are not 2,3,2'-tripalmitoyl, and d) when four of them are C.sub.1-40 aliphatic acyl groups, then they are not located at corresponding positions with each other or at 2,3,4,2'- or 2,3,6,2'-positions. The compounds of the above formula have anti-tumor activity.

  一种海藻糖衍生物，其化学式为：##STR1##其中R.sup.1、R.sup.2、R.sup.3、R.sup.4、R.sup.5、R.sup.6、R.sup.7和R.sup.8中的一个、两个、三个或四个独立地选择自C.sub.1-40脂肪族酰基组成的群体，其余的为氢原子，但须满足以下条件：a)当其中一个为C.sub.1-40脂肪族酰基时，它不是2-棕榈酰基或6-脂肪族酰基；b)当其中两个为C.sub.1-40脂肪族酰基时，它们不位于相应的位置上；c)当其中三个为C.sub.1-40脂肪族酰基时，它们不是2,3,2'-三棕榈酰基；d)当其中四个为C.sub.1-40脂肪族酰基时，它们不位于相应的位置上或位于2,3,4,2'-或2,3,6,2'-位置上。上述化合物具有抗肿瘤活性。
• Formulation of immunopotentiators
  申请人：Singh Manmohan

  公开号：US20120177681A1

  公开（公告）日：2012-07-12

  Immunopotentiators can be adsorbed to insoluble metal salts, such as aluminium salts, to modify their pharmacokinetics, pharmacodynamics, intramuscular retention time, and/or immunostimulatory effect. Immunopotentiators are modified to introduce a moiety, such as a phosphonate group, which can mediate adsorption. These modified compounds can retain or improve their in vivo immunological activity even when delivered in an adsorbed form.

  免疫增强剂可以被吸附到不溶性金属盐中，例如铝盐，以修改它们的药代动力学、药效学、肌肉内滞留时间和/或免疫刺激作用。免疫增强剂被改性以引入一个基团，例如膦酸盐基团，可以介导吸附。即使以吸附形式传递，这些改性化合物也可以保留或改善它们在体内的免疫活性。
• ADSORPTION OF IMMUNOPOTENTIATORS TO INSOLUBLE METAL SALTS
  申请人：Singh Manmohan

  公开号：US20130274465A1

  公开（公告）日：2013-10-17

  Immunopotentiators can be adsorbed to insoluble metal salts, such as aluminium salts, to modify their pharmacokinetics, pharmacodynamics, intramuscular retention time, and/or immunostimulatory effect. Immunopotentiators are modified to introduce a moiety, such as a phosphonate group, which can mediate adsorption. These modified compounds can retain or improve their in vivo immunological activity even when delivered in an adsorbed form.

  免疫增强剂可以吸附到不溶性金属盐上，例如铝盐，以改变它们的药代动力学、药效学、肌肉内滞留时间和/或免疫刺激作用。免疫增强剂被修改以引入一个基团，例如磷酸酯基团，可以介导吸附。即使以吸附形式输送，这些修改的化合物仍然可以保持或改善它们的体内免疫活性。
• New compounds associating peptidyl or aminoacyl residues to lipophilic groups and pharmaceutical compositions containing said new compounds
  申请人：ANVAR Agence Nationale de Valorisation de la Recherche

  公开号：EP0013856A1

  公开（公告）日：1980-08-06

  Compounds of formula in which - (NH-CHR-CO) and (NH-CHR'-CO) independently from each other are residues of aminoacids of the group containing glycine, alanine, β-alanine, arginine, asparagine, cysteine, glutamine, histidine, hydroxyproline, isoleucine, leucine, methionine, phenylalanine, proline, serine, threonine, tryptophane and valine; - m is zero or 1, - n is 1 or 2, - p is 0.1.2 or 3 - Y is either H or an acyl group with up to 4 carbon atoms - R1 and R2 are the same or different, at least one of them being a lipophilic group comprising a hydrocarbon chain containing at least 10 carbon atoms; or a salt of said compound A preferred compound is '-O(L-alanyl-D-isoglutaminyl- These compounds are useful as anti-infectious agents.

  式中的化合物 其中 - (NH-CHR-CO)和(NH-CHR'-CO)彼此独立地为包含甘氨酸、丙氨酸、β-丙氨酸、精氨酸、天冬酰胺、半胱氨酸、谷氨酰胺、组氨酸、羟脯氨酸、异亮氨酸、亮氨酸、蛋氨酸、苯丙氨酸、脯氨酸、丝氨酸、苏氨酸、色氨酸和缬氨酸的组中氨基酸的残基； - m 为 0 或 1 - n 为 1 或 2 - p 是 0.1.2 或 3 - Y 是 H 或最多 4 个碳原子的酰基 - R1 和 R2 相同或不同，其中至少一个是亲脂基团，包含至少 10 个碳原子的烃链；或所述化合物的盐 一种优选的化合物是'-O(L-丙氨酰-D-异谷氨酰胺酰-L-丙氨酰-D-异谷氨酰胺酰'。 这些化合物可用作抗感染剂。
• Adsorption of immunopotentiators to insoluble metal salts
  申请人：Novartis AG

  公开号：EP2719395A1

  公开（公告）日：2014-04-16

  Immunopotentiators can be adsorbed to insoluble metal salts, such as aluminium salts, to modify their pharmacokinetics, pharmacodynamics, intramuscular retention time, and/or immunostimulatory effect. Immunopotentiators are modified to introduce a moiety, such as a phosphonate group, which can mediate adsorption. These modified compounds can retain or improve their in vivo immunological activity even when delivered in an adsorbed form.

  免疫促效剂可吸附在铝盐等不溶性金属盐上，以改变其药代动力学、药效学、肌内滞留时间和/或免疫刺激效果。对免疫增强剂进行改性，引入一个可介导吸附的分子（如膦酸基）。这些经过修饰的化合物即使以吸附形式给药，也能保持或提高其体内免疫活性。