雌甾-1,3,5(10)-三烯-3,17beta-二醇 17-棕榈酸酯 | 5776-45-4

• 物质功能分类: 天然产物 - 甾体化合物
• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 类固醇和类固醇衍生物
• 中文名称: 雌甾-1,3,5(10)-三烯-3,17beta-二醇 17-棕榈酸酯
• 中文别名: 雌甾-1,3,5(10)-三烯-3,17beta-二醇17-棕榈酸酯；N-(9,10-二氢-9,10-二羰基-1-蒽基)[1,1'-联苯基]-4-甲酰胺
• 英文名称: estradiol 17β-monopalmitate
• 英文别名: 17β-estradiol-17-palmitate；estradiol-17β palmitate；Estradiol monopalmitate；[(8R,9S,13S,14S,17S)-3-hydroxy-13-methyl-6,7,8,9,11,12,14,15,16,17-decahydrocyclopenta[a]phenanthren-17-yl] hexadecanoate
• CAS: 5776-45-4
• 化学式: C₃₄H₅₄O₃
• 分子量: 510.801
• InChiKey: XQKLZLWOOGGXMV-KWXXMMNJSA-N

物化性质

• 熔点：
  81-85 °C
• 沸点：
  608.9±55.0 °C(Predicted)
• 密度：
  1.03±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  11.9
• 重原子数：
  37
• 可旋转键数：
  16
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.79
• 拓扑面积：
  46.5
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为产物：
  描述：

  3.17β-dipalmitoyloxy-estratriene-(1.3.5(10)) 在 氯化(1-丁基-3-甲基咪唑) 、 potassium hydroxide 作用下， 以 吡啶 、 甲苯 为溶剂， 反应 0.02h， 生成 雌甾-1,3,5(10)-三烯-3,17beta-二醇 17-棕榈酸酯
  参考文献：
  名称：

  使用微波辐射在离子液体中快速合成类固醇的长链脂肪酸酯：雌二醇单酯的便利一锅法

  摘要：

  我们报告了在离子液体 (IL) 中微波照射下几种类固醇的脂肪酸酯 (FAE) 衍生物的高产率快速合成 (1 分钟)。还报道了在雌二醇二酯的 C-3 处进行权宜的区域选择性水解。

  DOI：

  10.1016/j.steroids.2010.03.005

文献信息

• Mass spectrometric studies on 17β-estradiol-17-fatty acid esters: Evidence for the formation of anion-dipole intermediates
  作者：Laurent Debrauwer、Alain Paris、Dinesh Rao、Françoise Fournier、Jean-Claude Tabet

  DOI：10.1002/oms.1210270612

  日期：1992.6

  AbstractThe behaviour towards low collision energy processes (eV range) of [M  H]− prepared under negative ion chemical ionization (NICI) ammonia conditions from 17β‐estradiol‐17‐fatty acid esters has been investigated. From such bifunctional compounds containing two acidic sites (i.e. phenol and ester groups), two isomeric forms (i.e. phenoxide and enolate forms) characterize the [M  H]− ion structures, whose distribution depends on the ion preparation mode. Here NICI (ammonia) provides both phenoxide and enolate forms as the [M  H]− species. This behaviour contrasts with the regioselectivity observed for proton abstraction from phenol under NICI (N2O) and fast atom bombardment conditions. Production of both phenoxide and enolate forms in NICI (ammonia) is demonstrated under NICI (ND3) conditions in which DO‐labelled [Md  H]− enolate ions are produced in a similar yield to unlabelled [Md  D]− phenoxide ions. Collisionally activated dissociation (CAD) spectra of both isomeric deprotonated molecules differ strongly by the presence of two different pairs of complementary daughter ions, suggesting that these ionic species are unconvertible. This is due to a steric hindrance effect on the long‐distance proton transfer. A mechanistic investigation on the formation of fragment ion pairs produced under CAD was performed with various deuterium‐labelled molecules. From these experiments, evidence is provided for molecular isomerizations into ion‐dipole complexes (prior to dissociation) which are structurally dependent on the initial charge location. Direct dissociation of these intermediates competes with the occurrence of exothermic proton transfer(s) yielding the formation of other isomeric intermediate forms. The orientation of these proton transfers is dictated by the relative acidities of both moieties of the complex.
• Compositions, Methods and Uses for Treating Gender-Biased Immune Disorders
  申请人：Biocopea Limited

  公开号：US20160008376A1

  公开（公告）日：2016-01-14

  The present specification discloses compositions comprising at least one therapeutic compound capable of modulating a level and/or activity of a hormone and methods and uses for treating a gender-biased immune disorder using such compositions.
• [EN] COMPOSITIONS, METHODS AND USES FOR TREATING GENDER-BIASED IMMUNE DISORDERS<br/>[FR] COMPOSITIONS, PROCÉDÉS ET UTILISATIONS POUR LE TRAITEMENT DE TROUBLES IMMUNITAIRES DÉPENDANT DU SEXE
  申请人：BIOCOPEA LTD

  公开号：WO2016005599A1

  公开（公告）日：2016-01-14

  The present specification discloses compositions comprising at least one therapeutic compound capable of modulating a level and/or activity of a hormone and methods and uses for treating a gender-biased immune disorder using such compositions.
• Rapid synthesis of long chain fatty acid esters of steroids in ionic liquids with microwave irradiation: Expedient one-pot procedure for estradiol monoesters
  作者：Somdatta Deb、Kristiina Wähälä

  DOI：10.1016/j.steroids.2010.03.005

  日期：2010.10

  We report the rapid synthesis (1min) in high yield of fatty acid ester (FAE) derivatives of several steroids under microwave irradiation in an ionic liquid (IL). An expedient regioselective hydrolysis at C-3 of estradiol diesters is also reported.

  我们报告了在离子液体 (IL) 中微波照射下几种类固醇的脂肪酸酯 (FAE) 衍生物的高产率快速合成 (1 分钟)。还报道了在雌二醇二酯的 C-3 处进行权宜的区域选择性水解。