(S)-(+)-linalyl acetate | 51685-40-6

• 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: (S)-(+)-linalyl acetate
• 英文别名: (S)-linalyl acetate；linalyl acetate；(S)-linalyl acetate；(S)-Linalylacetat；(+)-Linalyl acetate；[(3S)-3,7-dimethylocta-1,6-dien-3-yl] acetate
• CAS: 51685-40-6
• 化学式: C₁₂H₂₀O₂
• 分子量: 196.29
• InChiKey: UWKAYLJWKGQEPM-GFCCVEGCSA-N

物化性质

• 沸点：
  220.0±0.0 °C(Predicted)
• 密度：
  0.897±0.06 g/cm3(Predicted)
• LogP：
  3.834 (est)

计算性质

• 辛醇/水分配系数(LogP)：
  3.3
• 重原子数：
  14
• 可旋转键数：
  6
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.58
• 拓扑面积：
  26.3
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  (S)-(+)-linalyl acetate 在 叔丁基过氧化氢 、 selenium(IV) oxide 作用下， 以 二氯甲烷 为溶剂， 反应 2.0h， 以51%的产率得到[(3S,6E)-8-hydroxy-3,7-dimethylocta-1,6-dien-3-yl] acetate
  参考文献：
  名称：

  （3 S，6 S）-（+）-3,7-二甲基-6-羟基-3-乙酰氧基辛基-1,7-二烯和（3 S，6 S）-（–）-3的部分合成香叶醇的7-二甲基辛基-1,7-二烯-3,6-二醇

  摘要：

  （3 S，6 S）-（+）-3,7-二甲基-6-羟基-3-乙酰氧基辛基-1,7-二烯和（3 S，6 S）-（–）-3,7的合成描述了通过手性2,3-环氧醇与Ph 3 P，吡啶，I 2和H 2 O的体系的重排生成的-二甲基辛基-1,7-二烯-3,6-二醇。

  DOI：

  10.1039/a809950b
• 作为产物：
  描述：

  (2S,3S)-2,3-环氧香叶醇 在 吡啶 、 4-二甲氨基吡啶 、 水 、 碘 、 三乙胺 、 三苯基膦 作用下， 以 乙醚 、 乙腈 为溶剂， 反应 22.0h， 生成 (S)-(+)-linalyl acetate
  参考文献：
  名称：

  （3 S，6 S）-（+）-3,7-二甲基-6-羟基-3-乙酰氧基辛基-1,7-二烯和（3 S，6 S）-（–）-3的部分合成香叶醇的7-二甲基辛基-1,7-二烯-3,6-二醇

  摘要：

  （3 S，6 S）-（+）-3,7-二甲基-6-羟基-3-乙酰氧基辛基-1,7-二烯和（3 S，6 S）-（–）-3,7的合成描述了通过手性2,3-环氧醇与Ph 3 P，吡啶，I 2和H 2 O的体系的重排生成的-二甲基辛基-1,7-二烯-3,6-二醇。

  DOI：

  10.1039/a809950b

文献信息

• Characterization of a novel esterase isolated from intertidal flat metagenome and its tertiary alcohols synthesis
  作者：Ki-Hoon Oh、Giang-Son Nguyen、Eun-Young Kim、Robert Kourist、Uwe Bornscheuer、Tae-Kwang Oh、Jung-Hoon Yoon

  DOI：10.1016/j.molcatb.2012.04.015

  日期：2012.8

  A gene coding for an esterase (EstEH112) was isolated from metagenome originated from Korean intertidal flat sediment. The putative esterase gene encoded a 340 amino acids protein with characteristic residues of lipolytic enzymes such as a conserved pentapeptide (GXSXG), the typical catalytic S-D-H triad, and a GGG(A)X-motif in the oxyanion hole near the active site similar to the hormone sensitive lipase (HSL) family. p-Nitrophenyl butyrate was the best substrate for the enzyme among the other p-nitrophenyl esters investigated. The apparent optimal temperature and pH for EstEH112 was 35 C and at pH 8.0, respectively. EstEH112 efficiently catalyzed the hydrolysis of various large tertiary alcohol esters. These characteristics of EstEH112 make it a potential candidate for application in biocatalysis. (C) 2012 Elsevier B.V. All rights reserved.
• Enantioselective monoterpene alcohol acetylation in Origanum, Mentha and Salvia species
  作者：Olga Larkov、Alon Zaks、Einat Bar、Efraim Lewinsohn、Nativ Dudai、Alfred M. Mayer、Uzi Ravid

  DOI：10.1016/j.phytochem.2008.07.018

  日期：2008.10

  Selected plants within the Origanum, Mentha and Salvia genera, that contain significant amounts of chiral volatile alcohols and their related acetates, exhibit remarkable enantioselectivity of alcohol acetyl transferase (AAT) activity and particularly can discriminate between linalool enantiomers. Origanum dayi AAT produced almost enantiomerically pure (R)-linalyl acetate by enzymatic acetylation of racemic linalool, whereas the closely related O. majorana AAT produced a mixture of (R)- and (S)-linalyl acetate with a ratio of 6:4. V-max of O. dayi acetylation activity was 30-fold higher for (R)-linalool, whereas in O. majorana no such differences were found. (C) 2008 Elsevier Ltd. All rights reserved.
• Enantioselective synthesis of each stereoisomer of the pyranoid linalool oxides: the linalool route
  作者：Giovanni Vidari、Anna Di Rosa、Giuseppe Zanoni、Carlo Bicchi

  DOI：10.1016/s0957-4166(99)00359-6

  日期：1999.9

  Each of the four enantiomerically pure tetrahydropyran linalool oxides was prepared by separate enantioselective Sharpless dihydroxylation of (R)- or (S)-linalyl acetate with AD-mix-alpha or AD-mix-beta, followed by a completely stereoselective N-phenylselenophthalimide cyclization of an intermediate allylic alcohol. (C) 1999 Elsevier Science Ltd. All rights reserved.
• PERFUME COMPOSITION
  申请人：Symrise AG

  公开号：US20140147404A1

  公开（公告）日：2014-05-29

  Suggested is a perfume composition, comprising (a) Petit grain oil and (b) Hydroxy carboxylic acid esters, which is particular useful for fighting various malodours.
• US9550959B2
  申请人：——

  公开号：US9550959B2

  公开（公告）日：2017-01-24