hydrocolorenone | 20482-28-4

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 异戊烯醇脂质
• 英文名称: hydrocolorenone
• 英文别名: Hydroxycolorenone；(5R,8S,8aS)-5-(2-hydroxypropan-2-yl)-3,8-dimethyl-4,5,6,7,8,8a-hexahydro-1H-azulen-2-one
• CAS: 20482-28-4
• 化学式: C₁₅H₂₄O₂
• 分子量: 236.354
• InChiKey: YXZJYDYPBCUCJX-WCQGTBRESA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.2
• 重原子数：
  17
• 可旋转键数：
  1
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.8
• 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：

  1α,7α,10αH-guaia-4,11-dien-3-one 在 mercury(II) diacetate 、 sodium hydroxide 、 sodium tetrahydroborate 、 sodium chloride 作用下， 以 四氢呋喃 、 水 、 乙醚 为溶剂， 反应 0.67h， 以91%的产率得到hydrocolorenone
  参考文献：
  名称：

  Ultrasound assisted reductive cleavage of eudesmane and guaiane γ-enonelactones. Synthesis of 1α,7α,10αH-guaian-4,11-dien-3-one and hydrocolorenone from santonin

  摘要：

  Ultrasound enhances the rate of reductive cleavage of the C-6-oxygen bond of sesquiterpene enonelactones. trans-Eudesmanolides 1c-1g, cis-eudesmanolides 2a-2c, and trans-guaianolides 4a-4d react with Zn in acetic acid-H2O under sonochemical conditions to afford the corresponding sesquiterpene. acids 3a-3g and 5a-5d, respectively in good yields. Starting from 5d two natural guaianes 1 alpha ,7 alpha ,10 alphaH-guaian-4, 11-dien-3-one (6) and hydrocolorenone (7) have been prepared in good yields through a straightforward sequence. (C) 2001 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4020(01)00986-3

文献信息

• Microbial transformation of sesquiterpenoids—I
  作者：H. Ishii、T. Tozyo、M. Nakamura、H. Minato

  DOI：10.1016/s0040-4020(01)92850-9

  日期：1970.1

  Guaioxide is a saturated sesquiterpene oxide, for which four possible structures have been suggested. Attempted microbial hydroxylation of the compound was successful, this led to a way to open its oxide linkage under mild conditions, and to a decision of the stereochemistry II for guaioxide.

  愈创木酚是饱和的倍半萜烯氧化物，已经提出了四种可能的结构。尝试了该化合物的微生物羟基化成功，这导致了在温和条件下打开其氧化物键的方法，并决定了环氧乙烷的立体化学II。
• Sesquiterpenoids from the Florets of Carthamus tinctorius (Safflower) and Their Anti-Atherosclerotic Activity
  作者：Lei Li、Juan Liu、Xinrui Li、Yuqin Guo、Yunqiu Fan、Hongzhen Shu、Guangxu Wu、Cheng Peng、Liang Xiong

  DOI：10.3390/nu14245348

  日期：——

  (1) Background: The florets of Carthamus tinctorius L. are traditionally used as a blood-activating drug and can be used for the treatment of atherosclerosis, but no compounds with anti-atherosclerotic activity have been reported. (2) Methods: This study investigated the chemical compounds from the florets of C. tinctorius. Comprehensive spectroscopic techniques revealed their structures, and ECD calculations

  (1)背景：红花传统上用作活血药物，可用于治疗动脉粥样硬化，但尚未见具有抗动脉粥样硬化活性的化合物的报道。 (2)方法：本研究调查了C.tinctorius小花的化学成分。综合光谱技术揭示了它们的结构，ECD 计算确定了它们的绝对构型。对这些化合物及其苷元进行尼罗红染色、油红 O 染色和胆固醇评估，以评估其对 RAW264.7 巨噬细胞中氧化低密度脂蛋白 (ox-LDL) 诱导的泡沫细胞形成的抑制活性。此外，通过测量 LPS 引起的 NO 产生抑制来测试 RAW264.7 巨噬细胞的抗炎活性。 (3)结果：从C.tinctorius小花中分离得到5个新的倍半萜类化合物(1-5)，经鉴定为(–)-(1R,4S,9S,11R)-caryophyll-8(13)-en-14-ol -5-一 (1), (+)-(1R,4R,9S,11R)-石竹-8(13)-en-14-ol-5-一 (2), (–)-(3Z
• Ultrasound assisted reductive cleavage of eudesmane and guaiane γ-enonelactones. Synthesis of 1α,7α,10αH-guaian-4,11-dien-3-one and hydrocolorenone from santonin
  作者：Gonzalo Blay、Victoria Bargues、Luz Cardona、Begoña Garcı́a、José R Pedro

  DOI：10.1016/s0040-4020(01)00986-3

  日期：2001.11

  Ultrasound enhances the rate of reductive cleavage of the C-6-oxygen bond of sesquiterpene enonelactones. trans-Eudesmanolides 1c-1g, cis-eudesmanolides 2a-2c, and trans-guaianolides 4a-4d react with Zn in acetic acid-H2O under sonochemical conditions to afford the corresponding sesquiterpene. acids 3a-3g and 5a-5d, respectively in good yields. Starting from 5d two natural guaianes 1 alpha ,7 alpha ,10 alphaH-guaian-4, 11-dien-3-one (6) and hydrocolorenone (7) have been prepared in good yields through a straightforward sequence. (C) 2001 Elsevier Science Ltd. All rights reserved.