十六碳烯酸 | 17004-51-2

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 脂肪酰基
• 中文名称: 十六碳烯酸
• 中文别名: 2-十六碳烯酸
• 英文名称: sapienic acid
• 英文别名: (Z)-hexadec-6-enoic acid
• CAS: 17004-51-2
• 化学式: C₁₆H₃₀O₂
• 分子量: 254.413
• InChiKey: NNNVXFKZMRGJPM-KHPPLWFESA-N

物化性质

• 沸点：
  369.8±11.0 °C(Predicted)
• 密度：
  0.905±0.06 g/cm3(Predicted)
• 溶解度：
  氯仿：可溶；乙醇：可溶；乙醚：可溶；甲醇：可溶

计算性质

• 辛醇/水分配系数(LogP)：
  6.2
• 重原子数：
  18
• 可旋转键数：
  13
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.81
• 拓扑面积：
  37.3
• 氢给体数：
  1
• 氢受体数：
  2

制备方法与用途

生物活性

Sapienic酸是一种常见于皮肤和粘膜中的脂肪酸，对皮肤和口腔中发现的革兰氏阳性和革兰氏阴性细菌具有可变的抗菌活性。具体来说，它对血链球菌、微生物链球菌和核纤梭菌表现出活性，其最小杀菌浓度（MBC）分别为31.3 μg/mL、375.0 μg/mL 和93.8 μg/mL。

靶点

Sapienic酸对以下细菌具有活性：

• Streptococcus sanguinis (MBC: 31.3 μg/mL)
• Streptococcus mitis (MBC: 375.0 μg/mL)
• Fusobacterium nucleatum (MBC: 93.8 μg/mL)

体外研究

Sapienic酸（最小杀菌浓度范围为31.3至375.0 μg/mL）对血链球菌、微生物链球菌和核纤梭菌表现出活性，但不适用于大肠杆菌、金黄色葡萄球菌、阴沟肠杆菌、铜绿假单胞菌以及某些诺卡氏菌（MBC > 500 μg/mL）。动力学分析显示，Sapienic酸对血链球菌和微生物链球菌的杀菌作用是逐渐发生的，并在24小时内完成。

反应信息

• 作为反应物：
  描述：

  十六碳烯酸 在 lithium diisopropyl amide 作用下， 以 四氢呋喃 、 乙醚 、 正庚烷 、 乙基苯 为溶剂， 反应 4.5h， 生成 1-methyl-2-[(Z)-5′-pentadecenyl]-4(1H)-quinolone
  参考文献：
  名称：

  Design, synthesis and antimycobacterial activities of 1-methyl-2-alkenyl-4(1H)-quinolones

  摘要：

  A series of 23 new 1-methyl-2-alkenyl-4(1H)quinolones have been synthesized and evaluated in vitro for their antimycobacterial activities against fast growing species of mycobacteria, such as Mycobacterium fortuitum, M. smegmatis and M. phlei. The compounds displayed good to excellent inhibition of the growth of the mycobacterial test strains with improved antimycobacterial activity compared to the hit compound, evocarpine. The most active compounds, which possessed chain length of 11-13 carbons at position-2 displayed potent inhibitory effects with an MIC value of 1.0 mg/L. In a human diploid embryonic lung cell line, MRC-5 cytotoxicity assay, the alkaloids showed weak to moderate cytotoxic activity. Biological evaluation of these evocarpine analogues on the less pathogenic fast growing strains of mycobacteria showed an interesting antimycobacterial profile and provided significant insight into the structure-activity relationships. (C) 2010 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2010.10.060
• 作为产物：
  描述：

  6-溴己酸 在 sodium hexamethyldisilazane 作用下， 以 四氢呋喃 、 甲苯 为溶剂， 反应 53.0h， 生成 十六碳烯酸
  参考文献：
  名称：

  Design, synthesis and antimycobacterial activities of 1-methyl-2-alkenyl-4(1H)-quinolones

  摘要：

  A series of 23 new 1-methyl-2-alkenyl-4(1H)quinolones have been synthesized and evaluated in vitro for their antimycobacterial activities against fast growing species of mycobacteria, such as Mycobacterium fortuitum, M. smegmatis and M. phlei. The compounds displayed good to excellent inhibition of the growth of the mycobacterial test strains with improved antimycobacterial activity compared to the hit compound, evocarpine. The most active compounds, which possessed chain length of 11-13 carbons at position-2 displayed potent inhibitory effects with an MIC value of 1.0 mg/L. In a human diploid embryonic lung cell line, MRC-5 cytotoxicity assay, the alkaloids showed weak to moderate cytotoxic activity. Biological evaluation of these evocarpine analogues on the less pathogenic fast growing strains of mycobacteria showed an interesting antimycobacterial profile and provided significant insight into the structure-activity relationships. (C) 2010 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2010.10.060

文献信息

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  DOI：10.1093/nar/gkz354

  日期：2019.7.9

  structurally diverse saturated and unsaturated fatty acid conjugated ASOs with a range of hydrophobicity. The binding affinity of ASO fatty acid conjugates to plasma proteins improved with fatty acid chain length and highest binding affinity was observed with ASO conjugates containing fatty acid chain length from 16 to 22 carbons. The degree of unsaturation or conformation of double bond appears to have

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• METHOD FOR PRODUCING CARBOXYLIC ACID
  申请人：KON Yoshihiro

  公开号：US20100210873A1

  公开（公告）日：2010-08-19

  It is an object of this invention to provide a method for efficiently synthesizing monocarboxylic acid, dicarboxylic acid, and tricarboxylic acid with the use of unsaturated triacyl glycerol as a starting material and hydrogen peroxide as an oxidant. Such method comprises allowing unsaturated triacyl glycerol to react with hydrogen peroxide in the presence of a quaternary ammonium polybasic acid hydrogen salt and at least one member selected from the group consisting of tungstic acid, heterotungstic acid, and salts thereof.

  本发明的目的是提供一种利用不饱和三酰甘油作为起始物质和过氧化氢作为氧化剂高效合成单羧酸、二羧酸和三羧酸的方法。这种方法包括在季铵多元酸氢盐和从钨酸、异钨酸和其盐组成的群体中至少选择一种成员的存在下，允许不饱和三酰甘油与过氧化氢发生反应。
• [EN] FRAGRANCE COMPOSITION<br/>[FR] COMPOSITION POUR PARFUM
  申请人：KAO CORP

  公开号：WO2010082684A1

  公开（公告）日：2010-07-22

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  提供了一种具有优异麝香气味的新型麝香香料。还提供了一种香料组合物，其包含以下式（1）所表示的大环内酯化合物作为活性成分：其中，A代表乙烯基或乙烯基；当A是乙烯基时，R代表具有3个碳原子的烷基，n为1至6的整数，而当A为乙烯基时，R代表具有1至3个碳原子的烷基，n为1至6的整数。
• Process for the preparation of cis-6-hexadecenoic acid
  申请人：——

  公开号：US20020107412A1

  公开（公告）日：2002-08-08

  The invention relates to a process for the preparation of cis-6-hexadecenoic acid of the formula I, 1 which comprises reacting a 1 ) a triphenylphosphonium salt of the formula II, R 1 OOC—(CH 2 ) 5 -P(R 2 ) 3 +X − II with decanal of the formula III H 3 C—(CH 2 ) 8 —CH═O  III or a 2 ) a triphenylphosphonium salt of the formula IV, H 3 C—(CH 2 ) 9 -P(R 2 ) 3 +X − IV with an aldehyde of the formula V, R 1 OOC—(CH 2 ) 4 —CH═O  V in a Wittig reaction, and b) saponifying the ester, formed by process step a 1 ) or a 2 ), of the formula VI, 2 where the substituents R 1 , R 2 and X − have the meanings given in the description.

  本发明涉及一种制备式I的顺式-6-十六碳烯酸的方法，其中包括反应a1）式II的三苯基膦酸盐，R1OOC—（CH2）5-P（R2）3+X−II与式III的癸醛，H3C—（CH2）8—CH═O  III或a2）式IV的三苯基膦酸盐，H3C—（CH2）9-P（R2）3+X−IV与式V的醛，R1OOC—（CH2）4—CH═O  V在维特格反应中，以及b）皂化由过程步骤a1）或a2）形成的酯的式VI，其中取代基R1，R2和X−具有所述描述中给出的含义。
• Preparation of saccharide esters
  申请人：Scherl Franz-Xaver

  公开号：US20050019296A1

  公开（公告）日：2005-01-27

  A process for the preparation of saccharide esters by reacting saccharides with activated carboxylic acids in a dipolar-aprotic solvent and in the absence of a basic amine compound is described.

  本发明涉及一种通过在双极-无极溶剂中与活性羧酸反应制备糖苷酯的方法，且在无碱性胺类化合物存在的情况下进行。