(4S)-4-羟基-3-亚甲基四氢呋喃-2-酮 | 38965-80-9

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 内酯类
• 中文名称: (4S)-4-羟基-3-亚甲基四氢呋喃-2-酮
• 英文名称: (S)-3-hydroxy-2-methylene-γ-butyrolactone
• 英文别名: (-)-6-tulipalin B；S-(-)-tulipalin B；(-)-tulipalin B；tulipalin B；tulipanin B；tulipalin A；(4S)-4-hydroxy-3-methylideneoxolan-2-one
• CAS: 38965-80-9
• 化学式: C₅H₆O₃
• 分子量: 114.101
• InChiKey: BFLSLERVRLOFCX-SCSAIBSYSA-N

物化性质

• 沸点：
  328.8±42.0 °C(Predicted)
• 密度：
  1.27±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  -0.4
• 重原子数：
  8
• 可旋转键数：
  0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.4
• 拓扑面积：
  46.5
• 氢给体数：
  1
• 氢受体数：
  3

安全信息

• 海关编码：
  2932209090

反应信息

• 作为反应物：
  描述：

  (4S)-4-羟基-3-亚甲基四氢呋喃-2-酮 在 1% Pd/C 、 氢气 作用下， 以 乙酸乙酯 为溶剂， 生成 3-hydroxy-2-methyl-γ-butyrolacton 、 (3R,4S)-4-hydroxy-3-methyldihydrofuran-2(3H)-one
  参考文献：
  名称：

  The antibacterial properties of 6-tuliposide B. Synthesis of 6-tuliposide B analogues and structure–activity relationship

  摘要：

  6-Tuliposide B is a secondary metabolite occurring specifically in tulip anthers. Recently, a potent antibacterial activity of 6-tuliposide B has been reported. However, its molecular target has not yet been established, nor its action mechanism. To shed light on such issues, 6-tuliposide B and tulipalin B analogues were synthesized and a structure-activity relationship (SAR) was examined using a broad panel of bacterial strains. As the results of SAR among a total of 25 compounds, only tulipalin B and the compounds having 3',4'-dihydroxy-2'-methylenebutanoate (DHMB) moieties showed any significant antibacterial activity. Moreover, the 3'R analogues of these compounds displayed essentially the same activities as 6-tuliposide B and the structure of the 3'R-DMBA moiety was the same as that of the proposed active moiety of cnicin. These results suggest that 6-tuliposide B has the same action mechanism as proposed for cnicin and bacteria) MurA is one of the major molecular targets of 6-tuliposide B. (C) 2009 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.phytochem.2009.10.008
• 作为产物：
  描述：

  (S)-2-(2,2-dimethyl-[1,3]dioxolan-4-yl)-propenal 在 盐酸 、 silver(l) oxide 作用下， 以 水 为溶剂， 反应 2.0h， 生成 (4S)-4-羟基-3-亚甲基四氢呋喃-2-酮
  参考文献：
  名称：

  Synthesis of (S)-(+)-methyl .BETA.,.GAMMA.-dihydroxy-.ALPHA.-methylenebutyrate and (S)-(-)-tulipalin B.

  摘要：

  已成功合成(S)-(+)-甲基β, γ-二羟基-α-亚甲基丁酸酯和(S)-(-)-郁金香醇B，这些是从Thunberg的海枣(SPIRAEA thunbergii Sieb.)中分离的抗菌物质，起始原料为异丙基羟基-D-甘油醛。

  DOI：

  10.1271/bbb1961.44.199

文献信息

• Purification and Characterization of a Tuliposide-Converting Enzyme from Bulbs of<i>Tulipa gesneriana</i>
  作者：Yasuo KATO、Kazuaki SHOJI、Makoto UBUKATA、Kengo SHIGETOMI、Yukio SATO、Noriyuki NAKAJIMA、Shinjiro OGITA

  DOI：10.1271/bbb.90226

  日期：2009.8.23

  An enzyme that catalyzes the stoichiometric conversion of 6-tuliposide into tulipalin was purified and characterized from bulbs of Tulipa gesneriana. The enzyme appeared to be a dimer, the relative molecular mass (Mr) of each subunit being 34,900; it had maximum activity and stability at neutral pH and moderate temperature. The enzyme preferentially acted on such glucose esters as 6-tuliposides, and to a lesser extent on p-nitrophenylacetate.

  一种催化6-郁金香苷转化为郁金香醇的酶从郁金香（Tulipa gesneriana）的鳞茎中被纯化和表征。该酶似乎是一个二聚体，每个亚单位的相对分子质量（Mr）为34,900；它在中性pH和适中的温度下具有最强的活性和稳定性。该酶优先作用于6-郁金香苷等葡萄糖酯，对对硝基苯乙酸酯的作用则较弱。
• The asymmetric Baylis-Hillman reaction as a template in organic synthesis
  作者：Linda Joy Brzezinski、Sara Rafel、James W. Leahy

  DOI：10.1016/s0040-4020(97)01025-9

  日期：1997.12

  The Baylis-Hillman reaction of camphor-based acrylates has been demonstrated to result in the formation of products with high optical purity. A model that explains these results and the use of these products in the formation of anti aldol adducts is discussed.

  樟脑基丙烯酸酯的Baylis-Hillman反应已被证明可导致形成具有高光学纯度的产物。讨论了一个解释这些结果的模型，以及这些产物在形成抗羟醛加合物中的用途。
• COMPOSITION CONTAINING S-(-)-TULIPALIN B OR ACETYLATED-S-(-)-TULIPALIN B
  申请人：PARK Deok Hoon

  公开号：US20080262082A1

  公开（公告）日：2008-10-23

  The present invention provides S-(−)-tulipalin B, acetylated-S-(−)-tulipalin B and an antibacterial composition comprising the same. The active compound tulipalin B and composition of the present invention exhibit superior and stable antibacterial activity over a broad range of temperature and pH, as compared to conventional natural antibacterial agents used in related industries. Therefore, the composition and active compound of the present invention can be widely used as a natural food preservative and/or an antibacterial agent in a variety of fields such as foods, pharmaceuticals, cosmetics, fibers, livingwares, and the like.

  本发明提供了S-（-）-郁金素B，乙酰化S-（-）-郁金素B以及包含它们的抗菌组合物。与相关行业中使用的传统天然抗菌剂相比，本发明的活性物质郁金素B和组合物在广泛的温度和pH范围内表现出优越和稳定的抗菌活性。因此，本发明的组合物和活性物质可以广泛用作天然食品防腐剂和/或各种领域中的抗菌剂，如食品、制药、化妆品、纤维、生活用品等。
• First total synthesis of 6-tuliposide B
  作者：Kengo Shigetomi、Takao Kishimoto、Kazuaki Shoji、Makoto Ubukata

  DOI：10.1016/j.tetasy.2008.05.019

  日期：2008.6

  Labile (+)-6-tuliposide B, an antimicrobial compound produced by tulip, was synthesized in nine steps from D-glucose via the Baylis-Hillman reaction of 2-(tert-butyldimethylsilyloxy)-acetaldehyde with 6-O-acryloyl-1-O-(2-trimethylsilylethyl)-beta-D-glucopyranoside, followed by a mild deprotection procedure using TFA in CH2Cl2. (C) 2008 Elsevier Ltd. All rights reserved.
• A facile method for the preparation of α-methylene-γ-butyrolactones from tulip tissues by enzyme-mediated conversion
  作者：Yasuo Kato、Hiroyuki Yoshida、Kazuaki Shoji、Yukio Sato、Noriyuki Nakajima、Shinjiro Ogita

  DOI：10.1016/j.tetlet.2009.06.018

  日期：2009.8

  We developed a facile method of enzyme-mediated conversion of 6-tuliposide to alpha-methylene-gamma-butyrolactone (tulipalin). We used a tuliposide-converting enzyme for the conversion of 6-tuliposides extracted from tulip tissues into the corresponding tulipalins in high yields within 2 h at pH 7.0. The resulting tulipalins were selectively extracted by using several organic solvents. (C) 2009 Elsevier Ltd. All tights reserved.