(4R)-p-menth-1-ene-7,8-diol | 83921-02-2

• 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: (4R)-p-menth-1-ene-7,8-diol
• 英文别名: P2VC2C4Tlu；2-[(1R)-4-(hydroxymethyl)cyclohex-3-en-1-yl]propan-2-ol
• CAS: 83921-02-2
• 化学式: C₁₀H₁₈O₂
• 分子量: 170.252
• InChiKey: XYKGEKWHBMLSGS-VIFPVBQESA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.6
• 重原子数：
  12
• 可旋转键数：
  2
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.8
• 拓扑面积：
  40.5
• 氢给体数：
  2
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  (4R)-p-menth-1-ene-7,8-diol 在 盐酸 作用下， 以 氯仿 为溶剂， 以95%的产率得到紫苏子醇
  参考文献：
  名称：

  Bluthe, Norbert; Ecoto, Jules; Fetizon, Marcel, Journal of the Chemical Society. Perkin transactions I, 1980, p. 1747 - 1751

  摘要：

  DOI：
• 作为产物：
  描述：

  (+)-α-松油醇 在 strain of Alternaria alternata 作用下， 以 甲醇 为溶剂， 反应 120.0h， 生成 (4R)-p-menth-1-ene-7,8-diol
  参考文献：
  名称：

  链格孢菌生物转化α-萜品醇

  摘要：

  α-松油醇( 1 )是一些中药中的主要挥发性成分，据报道，地老虎幼虫将α-松油醇(1)代谢为4R-油橄榄酸。本研究证实α-萜品醇可以通过链格孢发酵转化为4R-橄榄酸( 2 )和( 1S , 2R , 4R )-p-薄荷烷-1,2,8-三醇( 3 ) 。通过缩短发酵时间，7-羟基-α-萜品醇（ 2a ）被鉴定为氧化中间体，这与之前研究提出的假设一致。细胞色素 P450 酶也被证实可以催化这种生物转化。这是首次通过微生物发酵生物转化α-萜品醇的研究。

  DOI：

  10.1039/c9ra08042b

文献信息

• THE ENANTIOSELECTIVE BIOTRANSFORMATION OF α-TERPINEOL AND ITS ACETATE WITH THE CULTURED CELLS OF<i>NICOTIANA TABACUM</i>
  作者：Takayuki Suga、Toshifumi Hirata、Ym Sook Lee

  DOI：10.1246/cl.1982.1595

  日期：1982.10.5

  In the biotransformation of the enantiomers of p-menth-1-en-8-ol (α-terpineol) and 8-acetoxy-p-menth-1-ene (α-terpinyl acetate) with the cultured suspension cells of Nicotiana tabacum, it was clarified that the cultured cells effected the hydroxylation at the 6-position of (4R)-(+)-enantiomer in preference to the (4S)-(−)-enantiomer, whereas the cells did the hydrolysis of the acetoxyl group and the

  p-menth-1-en-8-ol (α-terpineol) 和 8-acetoxy-p-menth-1-ene (α-terpinyl acetate) 的对映异构体与烟草悬浮细胞的生物转化，澄清的是，培养的细胞在 (4R)-(+)-对映体的 6-位进行羟基化优先于 (4S)-(-)-对映体，而细胞进行乙酰氧基的水解和(4S)-(-)-α-松油醇乙酸酯的烯键羟基化优先于(4R)-(+)-对映异构体。
• New monoterpene glycosides and phenolic compounds from Distylium racemosum and their inhibitory activity against ribonuclease H
  作者：Jeong Ah Kim、Seo Young Yang、Anthony Wamiru、James B. McMahon、Stuart F.J. Le Grice、John A. Beutler、Young Ho Kim

  DOI：10.1016/j.bmcl.2011.03.091

  日期：2011.5

  Two new monoterpene glycosides, distyloside A-B (1-2), and a new megastigmane glucoside, iso-dihydrodendranthemoside A (3) were isolated from twigs and leaves of Distylium racemosum, along with five known phenolic compounds (4-8). The structures were established via spectroscopic techniques and chemical transformations, and the absolute stereochemistry of 3 was determined by Mosher's esterification. A homogeneous fluorescence resonance energy transfer (FRET) quenching assay was used to determine the inhibitory activity of isolates (1-8) on the ribonuclease H enzymes from HIV-1, 2, human, and Escherichia coli. Among them, 6 ''-O-galloylsalidroside (6) showed potent inhibitory effects with an IC(50) value of 3.5 mu M on HIV-2, and 1.7 mu M on human RNase H, respectively. (C) 2011 Elsevier Ltd. All rights reserved.
• Bluthe, Norbert; Ecoto, Jules; Fetizon, Marcel, Journal of the Chemical Society. Perkin transactions I, 1980, p. 1747 - 1751
  作者：Bluthe, Norbert、Ecoto, Jules、Fetizon, Marcel、Lazare, Sylvain

  DOI：——

  日期：——
• Biotransformation of α-terpineol by <i>Alternaria alternata</i>
  作者：Rui-Feng Mei、Ya-Xian Shi、Wei-He Duan、Hao Ding、Xiao-Ran Zhang、Le Cai、Zhong-Tao Ding

  DOI：10.1039/c9ra08042b

  日期：——

  α-Terpineol (1), the main volatile constituent in some traditional Chinese medicines, has been reported to be metabolized to 4R-oleuropeic acid by the larvae of common cutworms. The present study verified that α-terpineol could be converted to 4R-oleuropeic acid (2) and (1S,2R,4R)-p-menthane-1,2,8-triol (3) by Alternaria alternata fermentation. Using shortened fermentation times, 7-hydroxy-α-terpineol

  α-松油醇( 1 )是一些中药中的主要挥发性成分，据报道，地老虎幼虫将α-松油醇(1)代谢为4R-油橄榄酸。本研究证实α-萜品醇可以通过链格孢发酵转化为4R-橄榄酸( 2 )和( 1S , 2R , 4R )-p-薄荷烷-1,2,8-三醇( 3 ) 。通过缩短发酵时间，7-羟基-α-萜品醇（ 2a ）被鉴定为氧化中间体，这与之前研究提出的假设一致。细胞色素 P450 酶也被证实可以催化这种生物转化。这是首次通过微生物发酵生物转化α-萜品醇的研究。