6-[(E)-2-(2,6,6-三甲基-1-环己烯-1-基)乙烯基]-2-萘甲酸 | 86471-13-8

• 分子结构分类: 有机化合物 - 苯类化合物 - 萘
• 中文名称: 6-[(E)-2-(2,6,6-三甲基-1-环己烯-1-基)乙烯基]-2-萘甲酸
• 英文名称: (E)-6-[2-(2,6,6-trimethyl-1-cyclohexen-1-yl)ethenyl]-2-naphthalenecarboxylic acid
• 英文别名: 6-<(E)-2-(2,6,6-trimethyl-1-cyclohexen-1-yl)ethen-1-yl>-2-naphthalenecarboxylic acid；(E)-6-[2-(2,6,6-trimethyl-1-cyclohexen-1-yl)ethen-1-yl]-2-naphthalene carboxylic acid；SRI 5898-21；6-[2-(2,6,6-trimethyl-1-cyclohexen-1-yl)ethenyl]-2-naphthoic acid；(E)-6-[2-(2,6,6-trimethyl-1-cyclohexen-1-yl)-ethenyl]-2-naphthalene carboxylic acid；6-(2-(2,6,6-Trimethyl-1-cyclohexen-1-yl)ethen-1-yl)-2-naphthalenecarboxylic acid；6-[(E)-2-(2,6,6-trimethylcyclohexen-1-yl)ethenyl]naphthalene-2-carboxylic acid
• CAS: 86471-13-8
• 化学式: C₂₂H₂₄O₂
• 分子量: 320.431
• InChiKey: RCHMLZNVEBARAC-YRNVUSSQSA-N

物化性质

• 熔点：
  173-174 °C(Solv: ethyl acetate (141-78-6); hexane (110-54-3))
• 沸点：
  488.1±14.0 °C(Predicted)
• 密度：
  1.148±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  5.8
• 重原子数：
  24
• 可旋转键数：
  3
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.32
• 拓扑面积：
  37.3
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为产物：
  描述：

  methyl 6-<(E)-2-(2,6,6-trimethyl-1-cyclohexen-1-yl)ethen-1-yl>-2-naphthalenecarboxylate 在 氢氧化钾 作用下， 以 甲醇 、 水 为溶剂， 以75%的产率得到6-[(E)-2-(2,6,6-三甲基-1-环己烯-1-基)乙烯基]-2-萘甲酸
  参考文献：
  名称：

  Naphthenic and heterocyclic retinoic acid analogues

  摘要：

  环烷和杂环维甲酸类似物，如(E)-6-[2-(2,6,6-三甲基-1-环己烯-1-基)乙烯基]-2-萘醛，甲基6-[2-(2,6,6-三甲基-1-环己烯-1-基)乙烯基]-2-萘酸甲酯，6-[2-(2,6,6-三甲基-1-环己烯-1-基)乙烯基]-2-萘甲酸，(E)-1-(5-羧乙氧基-2-呋喃基)-2-甲基-4-(2,6,6-三甲基-1-环己烯-1-基)-1,3-丁二烯，(E)-1-(5-羧基-2-呋喃基)-2-甲基-4-(2,6,6-三甲基-1-环己烯-1-基)-1,3-丁二烯，(E)-1-(5-羧乙氧基噻吩-2-基)-2-甲基-4-(2,6,6-三甲基-1-环己烯-1-基)-1,3-丁二烯，以及(E)-1-(5-羧基噻吩-2-基)-2-甲基-4-(2,6,6-三甲基-1-环己烯-1-基)-1,3-丁二烯。这些视黄醇类化合物可用作抑制上皮细胞中的肿瘤促进剂和治疗非恶性皮肤疾病的化学预防剂。

  公开号：

  US04456618A1

文献信息

• Methods for treatment of sundamaged human skin with retinoids
  申请人：Kligman, Albert M.

  公开号：EP0253393A2

  公开（公告）日：1988-01-20

  Various effects of photoaging or sundamage of skin including impairment of differentiation of epidermal epithelial cells and loss of collagen fibers, abnormal changes in elastic fibers and deterioration of small blood vessels in the dermis of the skin are retarded by applying topically to the epidermis in a maintenance therapy program effective amounts of retinoids including retinoid derivatives and stereoisomers thereof such that epithelial growths are substantially reduced and prevented and the skin substantially regains and maintains its firmness, turgor and elasticity. Moreover, with persistent treatment dermal blood cells and vessels increase and the epidermis and dermis thicken, resulting in improved ability of the skin to sense, resist and recover from irritation or injury. Further, hyperpigmentation, lines and wrinkles due to aging are reduced and prevented. The treatment is particularly useful for human facial skin and preferably applied in amounts insufficient to cause excessive irritation.

  通过在维持治疗方案中向表皮局部施用有效量的维甲酸（包括维甲酸衍生物及其立体异构体），可延缓皮肤光老化或日晒损伤的各种影响，包括表皮上皮细胞分化障碍和胶原纤维的丧失、弹性纤维的异常变化以及皮肤真皮层小血管的退化，从而大大减少和防止上皮增生，并使皮肤大大恢复和保持其紧致度、韧性和弹性。此外，在坚持治疗的情况下，真皮血细胞和血管会增加，表皮和真皮会变厚，从而提高皮肤对刺激或损伤的感知、抵抗和恢复能力。此外，还能减少和预防色素沉着、细纹和因衰老产生的皱纹。这种疗法尤其适用于人的面部皮肤，其用量最好不足以造成过度刺激。
• Prevention of glucocorticoid-induced skin atrophy
  申请人：ORTHO PHARMACEUTICAL CORPORATION

  公开号：EP0266992A2

  公开（公告）日：1988-05-11

  The present invention is directed to the topical administra­tion of a retinoid-containing pharmaceutical composition for the prevention of glucocorticoid-induced skin atrophy.

  本发明涉及一种含维甲酸的药物组合物的局部用药，用于预防糖皮质激素引起的皮肤萎缩。
• Method for the treatment or prevention of intrinsically aged skin with retinoids
  申请人：ORTHO PHARMACEUTICAL CORPORATION

  公开号：EP0379367A2

  公开（公告）日：1990-07-25

  A method for the treatment or prevention of intrinsically aged skin by the topical administration of retinoids is described.

  本文介绍了一种通过局部使用维甲酸来治疗或预防内在老化皮肤的方法。
• Use of retinoids for preventing and reducing the size of striae distensae lesions
  申请人：Kligman, Albert M.

  公开号：EP0415458A2

  公开（公告）日：1991-03-06

  Striae distensae lesions may be prevented and/or reduced in size by topically applying to the skin affected with the lesions an effective amount of a retinoid, preferably retinoic acid, preferably by daily application in a dermatologically acceptable vehicle, such as a cream base, at a concentration of about 0.025 to 0.1 weight percent retinoic acid. When applied during the striae rubrae stage, the retinoid may be effective to prevent the formation of striae albae lesions, and when applied in either stage, the retinoid may be effective to reduce the width and depth of the lesions, with improved texture and softness.

  可通过在受皮损影响的皮肤上局部施用有效量的维甲酸（最好是维甲酸）来防止和/或缩小红斑皮损，维甲酸的浓度最好为 0.025 至 0.1 重量百分比。在红斑期施用时，维甲酸可有效防止白斑的形成；在任何一个阶段施用时，维甲酸可有效减少皮损的宽度和深度，并改善质地和柔软度。
• Use of retinoids for reversing glucocorticoid-induced skin atrophy
  申请人：ORTHO PHARMACEUTICAL CORPORATION

  公开号：EP0415766A2

  公开（公告）日：1991-03-06

  The present invention is directed to the topical administration of a retinoid-containing pharmaceutical composition for reversing the effects of glucocorticoid-induced skin atrophy.

  本发明涉及一种含维甲酸的药物组合物的局部用药，用于逆转糖皮质激素诱导的皮肤萎缩的影响。