desacetyluvaricin | 98767-45-4

• 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: desacetyluvaricin
• 英文别名: (2S)-4-[(13R)-13-hydroxy-13-[(2R,5R)-5-[(2R,5R)-5-[(1S)-1-hydroxyundecyl]oxolan-2-yl]oxolan-2-yl]tridecyl]-2-methyl-2H-furan-5-one
• CAS: 98767-45-4
• 化学式: C₃₇H₆₆O₆
• 分子量: 606.927
• InChiKey: URLVCROWVOSNPT-HJPPHTJLSA-N

物化性质

• 熔点：
  67.5-69 °C(Solv: methanol (67-56-1); water (7732-18-5))
• 沸点：
  719.1±35.0 °C(Predicted)
• 密度：
  1.023±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  11.2
• 重原子数：
  43
• 可旋转键数：
  25
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.92
• 拓扑面积：
  85.2
• 氢给体数：
  2
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  甲氧基-三氟甲基苯 、 desacetyluvaricin 在 吡啶 作用下， 反应 1.0h， 生成 (R)-3,3,3-Trifluoro-2-methoxy-2-phenyl-propionic acid (R)-13-((S)-5-methyl-2-oxo-2,5-dihydro-furan-3-yl)-1-{(2R,5R,2'R,5'R)-5'-[(S)-1-((R)-3,3,3-trifluoro-2-methoxy-2-phenyl-propionyloxy)-undecyl]-octahydro-[2,2']bifuranyl-5-yl}-tridecyl ester
  参考文献：
  名称：

  Annonaceous Acetogenins from the Seeds of Annona squamosa. Adjacent Bis-tetrahydrofuranic Acetogenins.

  摘要：

  除了squamocin (1)和squamostatin-A之外，Annona squamosa L.种子的石油醚提取物还产生了13种相邻和4种非相邻的双四氢呋喃乙酰基肽。这13种乙酰基肽的结构（命名为squamocins-B (2)、-C (3)、-D (4)、-E (5)、-F (6)、-G (7)、-H (8)、-I (9)、-J (10)、-K (11)、-L(12)、-M (13)和-N (14)）是根据光谱证据确定的。Squamocins-B、-D、-E、-F、-I、-K和-N是新的乙酰基肽。这些乙酰基肽的结构在碳数（C37或C35）、羟基的数量和位置（在C-4、C-12、C-28或C-29处被取代）以及双四氢呋喃部分的立体化学方面有所不同。Squamocin-N (14)的双四氢呋喃部分具有前所未有的threo-cis-threo-cis-threo立体化学。值得注意的是，9和10在非对映异构体对中同时出现

  DOI：

  10.1248/cpb.42.1163

文献信息

• New method for the determination of the absolute stereochemistry in antitumoral annonaceous acetogenins
  作者：M. Carmen González、Catherine Lavaud、Teresa Gallardo、M. Carmen Zafra-Polo、Diego Cortes

  DOI：10.1016/s0040-4020(98)00301-9

  日期：1998.5

  several acetogenins were determined through p-bromophenylurethane derivatives and subsequent Mosher ester methodology. This method has been applied on α,α′-dihydroxylated adjacent bis-THF acetogenins with a threo/cis/threo/cis/erythro relative configuration membrarollin (1), a new acetogenin isolated from Rollinia membranacea seeds, rollimembrin (2), membranacin (3) and rolliniastatin-1 (4), and a th

  通过对-溴苯基氨基甲酸酯衍生物和随后的Mosher酯方法确定了几种产黄素中甲醇中心的绝对构型。该方法已应用于具有苏式/顺式/苏式/顺式/顺式/赤型相对构型的membrarollin（1）的α，α'-二羟基化的相邻双THF乙酸原素，一种从Rollinia membranacea种子，rollimembrin（2），membranacin分离出的新的乙酸原素。（3）和rolliniastatin-1（4）以及苏氨酸/反式/苏氨酸/反式甲状腺相对构型胃泌素（5），鳞霉素（6）和脱乙酰葡萄球蛋白（7）。发现1是哺乳动物线粒体复合体I的最有效抑制剂。
• EXTRACTS, FRACTIONS AND COMPOSITIONS COMPRISING ACETOGENINS AND THEIR APPLICATIONS
  申请人：Laila Nutraceuticals

  公开号：EP2490543B1

  公开（公告）日：2015-07-22
• COMPOSITIONS COMPRISING EXTRACTS OR FRACTIONS DERIVED FROM ANNONA SQUAMOSA FOR THE PREVENTION, TREATMENT OR CONTROL OF INFLAMMATORY AND METABOLIC DISORDERS
  申请人：LAILA NUTRACEUTICALS

  公开号：US20140056987A1

  公开（公告）日：2014-02-27

  The invention discloses synergistic composition comprising at least one Annona squamosa derived component standardized to acetogenin compound(s) having α,β-unsaturated-γ-methyl-γ-lactone moiety in combination with at least one biologically active ingredient derived from plants, animals or microorganisms such as vitamins, amino acids, minerals, fibers, various plant and herbal extracts for the prevention, treatment, inhibition or controlling inflammation and/or metabolic disorders and other associated or related diseases. The invention further discloses the method of treating inflammation and/or metabolic disorders and other associated or related diseases.
• US9427425B2
  申请人：——

  公开号：US9427425B2

  公开（公告）日：2016-08-30
• Annonaceous Acetogenins from the Seeds of Annona squamosa. Adjacent Bis-tetrahydrofuranic Acetogenins.
  作者：Mahendra SAHAI、Sanjewon SINGH、Manorama SINGH、Yogesh Kumar GUPTA、Satoko AKASHI、Reiko YUJI、Kazuo HIRAYAMA、Hitomi ASAKI、Hitoshi ARAYA、Noriyuki HARA、Tadashi EGUCHI、Katsumi KAKINUMA、Yoshinori FUJIMOTO

  DOI：10.1248/cpb.42.1163

  日期：——

  The petroleum ether extract of the seeds of Annona squamosa L. yielded thirteen adjacent and four non-adjacent bis-tetrahydrofuranic acetogenins, in addition to squamocin (1) and squamostatin-A. The structures of the thirteen acetogenins, named as squamocins-B (2), -C (3), -D (4), -E (5), -F (6), -G (7), -H (8), -I (9), -J (10), -K (11), -L(12), -M (13) and -N (14), have been established on the basis of spectral evidence. Squamocins-B, -D, -E, -F, -I, -K and -N are new acetogenins. The structures of these acetogenins vary in hte carbon number (C37 or C35), the number and position of hydroxyl groups (substituted at C-4, C-12, C-28 or C-29) and the stereochemistry at the bis-tetrahydrofuran moiety. Squamocin-N (14) has an unprecedented threo-cis-threo-cis-threo stereochemistry in its bis-tetrahydrofuran portion. Co-occurrence on a diastereoisomeric pair, 9 and 10, is noteworthy.

  除了squamocin (1)和squamostatin-A之外，Annona squamosa L.种子的石油醚提取物还产生了13种相邻和4种非相邻的双四氢呋喃乙酰基肽。这13种乙酰基肽的结构（命名为squamocins-B (2)、-C (3)、-D (4)、-E (5)、-F (6)、-G (7)、-H (8)、-I (9)、-J (10)、-K (11)、-L(12)、-M (13)和-N (14)）是根据光谱证据确定的。Squamocins-B、-D、-E、-F、-I、-K和-N是新的乙酰基肽。这些乙酰基肽的结构在碳数（C37或C35）、羟基的数量和位置（在C-4、C-12、C-28或C-29处被取代）以及双四氢呋喃部分的立体化学方面有所不同。Squamocin-N (14)的双四氢呋喃部分具有前所未有的threo-cis-threo-cis-threo立体化学。值得注意的是，9和10在非对映异构体对中同时出现