Hexadecyl tetradec-9-enoate

• 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: Hexadecyl tetradec-9-enoate
• 化学式: C₃₀H₅₈O₂
• 分子量: 450.8
• InChiKey: DYIOQMKBBPSAFY-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  13.2
• 重原子数：
  32
• 可旋转键数：
  27
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.9
• 拓扑面积：
  26.3
• 氢给体数：
  0
• 氢受体数：
  2

文献信息

• Process for Preparation of Hexadecyl Cis-9-Tetradecenoate and Hexadecyl Cis-10-Tetradecenoate
  申请人：Bethala Lakshmi Anu Prabhavathi Devi

  公开号：US20110269987A1

  公开（公告）日：2011-11-03

  Hexadecyl cis-9-tetradecenoate commonly known as Cetyl myristoleate (CMO) is being used for the treatment of osteoarthritis and other joint inflammatory diseases, cis-9-Tetradecenoic acid (cis-9-myristoleic acid) is the main precursor for the preparation of CMO. As there are limited natural plant sources for cis-9-tetradecenoic acid, the present invention aimed at the synthesis of cis-9-tetradecenoic acid methyl ester from oleic acid methyl ester. As oleic acid is not available in pure form, this has to be isolated from oleic acid-rich oils like olive oil. cis-10-Tetradecenoic acid methyl ester, an isomer of cis-9-tetradecenoic acid was also prepared from undecenoic acid methyl ester, a derivative of castor oil. Undecenoic acid is easily available commercially in pure form. Hexadecyl cis-9-tetradecenoate and hexadecyl c/s-10-tetradecenoate were prepared by enzymatic transesterification of cis-9-tetradecenoic acid methyl ester and cis-10-tetradecenoic acid methyl ester with 1-hexadecanol (cetyl alcohol) respectively. Both the isomers of cetyl myristoleate were evaluated for anti arthritis, blocking inflammation and reduction of adjuvant-induced arthritis in rats.

  十六烷基顺-9-十四碳烯酸盐通常被称为鲸蜡醇豆蔻酸酯（CMO），目前正被用于治疗骨关节炎和其他关节炎症疾病，顺-9-十四碳烯酸（顺-9-豆蔻酸）是制备CMO的主要前体。由于顺-9-十四碳烯酸的自然植物来源有限，本发明旨在从油酸甲酯合成顺-9-十四碳烯酸甲酯。由于油酸无法以纯净形式获得，因此需要从富含油酸的油类如橄榄油中提取。还从十一烯酸甲酯，即蓖麻油的衍生物，制备了顺-10-十四碳烯酸甲酯，这是顺-9-十四碳烯酸的异构体。十一烯酸在市场上容易以纯净形式获得。通过酶促转酯反应，分别用顺-9-十四碳烯酸甲酯和顺-10-十四碳烯酸甲酯与1-十六醇（鲸蜡醇）反应，制备了十六烷基顺-9-十四碳烯酸盐和十六烷基顺-10-十四碳烯酸盐。这两种鲸蜡醇豆蔻酸酯的异构体都进行了抗关节炎、阻断炎症和在大鼠中减少佐剂诱导关节炎的评价。
• Pharmaceutical Compositions Comprising Capsaicin Esters for Treating Pain and Cold Sores
  申请人：Singh Chandra U.

  公开号：US20140134261A1

  公开（公告）日：2014-05-15

  The present invention relates to pharmaceutical compositions comprising ester(s) of capsaicin and at least one other agent selected from salicylates, menthol, boswellic acids, DMSO, methyl sulfonylmethane, NSAIDs, corticosteroids, emu oil, opioid agonists and antagonists, NMDA antagonists, tramadol, hyaluronic acid, α2δ ligands, santalol, santalyl acetate, amyris alcohol, amyris acetate, aloe vera gel and aloe vera juice, for improved therapeutic properties. Further, the present invention relates to pharmaceutical compositions comprising high concentrations of ester(s) of capsaicin. Further, the present invention relates to a method of relieving pain due to various diseases in subjects by administering the pharmaceutical compositions of the invention. Further, the present invention relates to methods of relieving fever blisters due to cold sores in subjects by administering the pharmaceutical compositions comprising an ester of capsaicin and one other agent selected from santalol, santalyl acetate, amyris alcohol and amyris acetate.

  本发明涉及含有辣椒素酯及至少一种来自水杨酸酯、薄荷脑、乳香酸、二甲基亚砜、甲基亚砜、非甾体抗炎药、皮质类固醇、鸸鹋油、阿片受体激动剂和拮抗剂、NMDA受体拮抗剂、曲马多、透明质酸、α2δ受体配体、檀香醇、檀香醋酸酯、白檀醇、白檀醋酸酯、芦荟凝胶和芦荟汁的药物组合物，用于改善治疗特性。此外，本发明涉及含有高浓度辣椒素酯的药物组合物。此外，本发明涉及通过给予本发明的药物组合物来减轻受试者因各种疾病而导致的疼痛的方法。此外，本发明涉及通过给予含有辣椒素酯及来自檀香醇、檀香醋酸酯、白檀醇和白檀醋酸酯中的一种的药物组合物来减轻受试者因感冒引起的发热疱疹的方法。
• Esters of capsaicin for treating pain
  申请人：Singh Chandra Ulagaraj

  公开号：US20080020996A1

  公开（公告）日：2008-01-24

  The present invention relates to the formulations of ester derivatives of capsaicin and ester derivatives of myristoleic acid. These derivatives are capable of reverting to the active parent compound following enzymatic or chemical hydrolysis. These derivatives have a higher lipophilicity, lipid solubility and less irritation to the skin than the parent compound, and hence are better able to be incorporated into certain pharmaceutical formulations, including cream and ointment pharmaceutical formulations. The pharmaceutical compositions of the present invention contain a compound of following formula (Ia): R—CO-CAP   (Ia) wherein CAP refers to collectively the capsaicins represented in FIG. 1 and a compound of formula (Ib): MCO-O—R   (Ib) wherein MCO refers to myristoleic acid. In formulae Ia and Ib, R is selected from alkyl groups of up to about 18 carbon atoms and aryl groups of up to about 18 carbon atoms and alkylene group of up to about 18 carbon atoms and an arylene group of up to about 18 carbon atoms. The alkyl, aryl and alkylene groups may be substituted or un-substituted, branched or straight chains. In addition, R may contain heteroatoms and may be straight chained or branched. The pharmaceutical compositions containing compounds of formulae Ia and Ib are useful for pain management in mammals in vivo and have been contemplated to be used in the treatment of various pains in humans.

  本发明涉及辣椒素酯衍生物和肉豆蔻油酸酯衍生物的配方。这些衍生物能够在酶解或化学水解后恢复为活性母化合物。这些衍生物具有更高的亲脂性、脂溶性，对皮肤的刺激性较小，因此更容易被纳入某些药物配方中，包括膏剂和药膏配方。本发明的药物组合物含有下式（Ia）的化合物：R—CO-CAP（Ia），其中CAP指的是在图1中表示的辣椒素，和下式（Ib）的化合物：MCO-O—R（Ib），其中MCO指的是肉豆蔻油酸。在式Ia和Ib中，R选自碳原子数最多约为18的烷基基团和碳原子数最多约为18的芳基基团以及碳原子数最多约为18的烷基基团和碳原子数最多约为18的芳基基团。烷基、芳基和烷基基团可以是取代或未取代的，支链或直链。此外，R可能含有杂原子，可能是直链或支链的。含有式Ia和Ib的药物组合物对于体内哺乳动物的疼痛管理是有用的，并已考虑用于治疗人类的各种疼痛。
• Treating irrtable bowel syndrome or disease
  申请人：——

  公开号：US20030171432A1

  公开（公告）日：2003-09-11

  The treatment of humans or other mammals for irritable bowel syndrome (IBS) or irritable bowel disease (IBD) using dosage forms or compositions that include cetyl myristate alone or (in admixture or serially) both cetyl myristate and cetyl palmitate.

  使用含有十六烷酸肉豆蔻酸或（混合或依次）包括十六烷酸肉豆蔻酸和十六烷酸棕榈酸的剂型或组合物治疗人类或其他哺乳动物的肠易激综合征（IBS）或肠易激疾病（IBD）。
• Local regional chemotherapy and radiotherapy using in situ hydrogel
  申请人：Yang J. David

  公开号：US20050208138A1

  公开（公告）日：2005-09-22

  Methods regarding local regional treatment in situ for an individual, such as of a tumor, are provided herein. A hydrogel composition is generated in situ in the tumor by administering a polymer, such as a polysaccharide or a polyamino acid, with a therapeutic agent, such as a radionuclide or a drug, and administering a cross-linking agent. The hydrogel/therapeutic agent composition is retained in the tumor for safe and efficient tumor therapy. Alternatively, a hydrogel composition is generated in situ in an artery which nourishes a tumor to occlude the artery.

  本文提供了有关个体局部区域治疗方法的信息，例如针对肿瘤的治疗方法。通过给予聚合物，例如多糖或聚氨基酸，和治疗剂，例如放射性核素或药物，以及给予交联剂，在肿瘤内部原位生成一种水凝胶组合物。水凝胶/治疗剂组合物在肿瘤内部保留，以实现安全和有效的肿瘤治疗。或者，可以在为肿瘤提供营养的动脉内原位生成一种水凝胶组合物，以阻塞该动脉。