榄香素 | 487-11-6

• 物质功能分类: 生物化工 - 提取物
• 分子结构分类: 有机化合物 - 苯类化合物 - 苯酚醚
• 中文名称: 榄香素
• 中文别名: 欖[香]素；5-烯丙基-1,2,3-三甲氧基苯
• 英文名称: elemicin
• 英文别名: 1,2,3-trimethoxy-5-(2-propenyl)benzene；elemicine；3-(3,4,5-trimethoxyphenyl)-1-propene；5-allyl-1,2,3-trimethoxybenzene；3,4,5-trimethoxyallylbenzene；1,2,3-trimethoxy-5-prop-2-enylbenzene；4-allyl-1,2,6-trimethoxy benzene
• CAS: 487-11-6
• 化学式: C₁₂H₁₆O₃
• mdl: MFCD01656688
• 分子量: 208.257
• InChiKey: BPLQKQKXWHCZSS-UHFFFAOYSA-N

物化性质

• 沸点：
  152-156 °C
• 密度：
  1.0630 g/cm3
• 溶解度：
  氯仿（微溶）、乙酸乙酯（微溶）
• LogP：
  2.298 (est)
• 物理描述：
  Colourless to pale straw coloured viscous liquid; Spice with floral notes
• 折光率：
  1.529-1.534
• 保留指数：
  1531;1518;1527;1518;1512;1521;1521;1522;1524;1531;1516;1553;1548;1556;1521;1525;1512;1520;1512;1531;1515;1516;1516;1517;1529;1518;1526;1517;1525;1512;1525;1525;1515;1519;1530;1530;1531;1524.2

计算性质

• 辛醇/水分配系数(LogP)：
  2.5
• 重原子数：
  15
• 可旋转键数：
  5
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.333
• 拓扑面积：
  27.7
• 氢给体数：
  0
• 氢受体数：
  3

安全信息

• 储存条件：
  存储条件：2-8°C，干燥，密封。

SDS

Material Safety Data Sheet

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Section 1. Identification of the substance
Product Name: Elemicin
Synonyms:

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Section 2. Hazards identification
Harmful by inhalation, in contact with skin, and if swallowed.

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Section 3. Composition/information on ingredients.
Ingredient name: Elemicin
CAS number: 487-11-6

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Section 4. First aid measures
Skin contact: Immediately wash skin with copious amounts of water for at least 15 minutes while removing
contaminated clothing and shoes. If irritation persists, seek medical attention.
Eye contact: Immediately wash skin with copious amounts of water for at least 15 minutes. Assure adequate
flushing of the eyes by separating the eyelids with fingers. If irritation persists, seek medical
attention.
Inhalation: Remove to fresh air. In severe cases or if symptoms persist, seek medical attention.
Ingestion: Wash out mouth with copious amounts of water for at least 15 minutes. Seek medical attention.

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Section 5. Fire fighting measures
In the event of a fire involving this material, alone or in combination with other materials, use dry
powder or carbon dioxide extinguishers. Protective clothing and self-contained breathing apparatus
should be worn.

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Section 6. Accidental release measures
Personal precautions: Wear suitable personal protective equipment which performs satisfactorily and meets local/state/national
standards.
Respiratory precaution: Wear approved mask/respirator
Hand precaution: Wear suitable gloves/gauntlets
Skin protection: Wear suitable protective clothing
Eye protection: Wear suitable eye protection
Methods for cleaning up: Mix with sand or similar inert absorbent material, sweep up and keep in a tightly closed container
for disposal. See section 12.
Environmental precautions: Do not allow material to enter drains or water courses.

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Section 7. Handling and storage
Handling: This product should be handled only by, or under the close supervision of, those properly qualified
in the handling and use of potentially hazardous chemicals, who should take into account the fire,
health and chemical hazard data given on this sheet.
Store in closed vessels, refrigerated.
Storage:

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Section 8. Exposure Controls / Personal protection
Engineering Controls: Use only in a chemical fume hood.
Personal protective equipment: Wear laboratory clothing, chemical-resistant gloves and safety goggles.
General hydiene measures: Wash thoroughly after handling. Wash contaminated clothing before reuse.

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Section 9. Physical and chemical properties
Appearance: Not specified
Boiling point: No data
No data
Melting point:
Flash point: No data
Density: No data
Molecular formula: C12H16O3
Molecular weight: 208.3

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Section 10. Stability and reactivity
Conditions to avoid: Heat, flames and sparks.
Materials to avoid: Oxidizing agents.
Possible hazardous combustion products: Carbon monoxide.

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Section 11. Toxicological information
No data.

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Section 12. Ecological information
No data.

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Section 13. Disposal consideration
Arrange disposal as special waste, by licensed disposal company, in consultation with local waste
disposal authority, in accordance with national and regional regulations.

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Section 14. Transportation information
Non-harzardous for air and ground transportation.

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Section 15. Regulatory information
No chemicals in this material are subject to the reporting requirements of SARA Title III, Section
302, or have known CAS numbers that exceed the threshold reporting levels established by SARA
Title III, Section 313.

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SECTION 16 - ADDITIONAL INFORMATION
N/A

制备方法与用途

产品描述

榄香素是一种无色油状液体，沸点为146～147°C/10mmHg。目前，榄香素主要用于医药麻醉。尽管许多植物中含有该成分，但由于含量较低且难以提取，并且杂质较多而被放弃。因此，科研人员尝试采用化学合成的方法来制备榄香素，但这种方法也存在含苯类其他杂质的风险，对人体可能造成较大危害。因此，寻求新的解决方案迫在眉睫。

产品用途

榄香素是一种无色油状液体，沸点为146～147°C/10mmHg，目前主要用于医药麻醉。此外，榄香素也可用于制备含有肟菌酯和榄香素的高效杀菌组合物。

生物活性

Elemicin 是一种烯基苯类化合物，在许多草药和香料中广泛分布。它通过代谢激活抑制硬脂酰辅酶 A 去饱和酶 1 (SCD1) 的活性。Elemicin 在芳香族食品中的含量较高，具有抗微生物、抗氧化剂和抗病毒的生物活性，并且还具有遗传毒性和致癌性。

靶点

• SCD1

反应信息

• 作为反应物：
  描述：

  榄香素 在 氢氧化钾 作用下， 以 乙醇 为溶剂， 生成 1,2,3-三甲氧基-5-((E)-丙-1-烯基)苯
  参考文献：
  名称：

  SYNTHESIS OF THE TRIMETHOXYPHENYLPROPENES

  摘要：

  不可用。

  DOI：

  10.1139/v65-478
• 作为产物：
  描述：

  2,6-二甲氧基苯酚 在 potassium carbonate 作用下， 以 丙酮 为溶剂， 反应 50.0h， 生成 榄香素
  参考文献：
  名称：

  新木脂素 Rhaphidecursinol A 和 Virolongin B 的首次对映选择性合成

  摘要：

  首次报道了新木脂素 Rhaphidecursinol A 和 Virolongin B 的对映选择性合成。合成中的关键反应是Sharpless不对称二羟基化和Mitsunobu反应。Rhaphidecursinol A 的绝对构型得到确认。

  DOI：

  10.1002/jccs.200400144

文献信息

• NiH‐Catalyzed Migratory Defluorinative Olefin Cross‐Coupling: Trifluoromethyl‐Substituted Alkenes as Acceptor Olefins to Form <i>gem</i> ‐Difluoroalkenes
  作者：Fenglin Chen、Xianfeng Xu、Yuli He、Genping Huang、Shaolin Zhu

  DOI：10.1002/anie.201915840

  日期：2020.3.23

  a NiH-catalyzed migratory defluorinative coupling between two electronically differentiated olefins. A broad range of unactivated donor olefins can be joined directly to acceptor olefins containing an electron-deficient trifluoromethyl substituent in both intra- and intermolecular fashion to form gem-difluoroalkenes. This migratory coupling shows both site- and chemoselectivity under mild conditions

  我们报告了两个电子分化的烯烃之间的镍氢催化迁移脱氟偶联。多种未活化的供体烯烃可以以分子内和分子间方式直接与含有缺电子的三氟甲基取代基的受体烯烃键合，形成宝石-二氟烯烃。这种迁移偶联在温和条件下显示出位选择性和化学选择性，并形成了叔碳或季碳中心。
• A Facile, Convenient, and Green Route to (E)-Propenylbenzene Flavors and Fragrances by Alkene Isomerization
  作者：Douglas Grotjahn、Casey Larsen、Erik Paulson、Gulin Erdogan

  DOI：10.1055/s-0035-1560205

  日期：——

  (E)-Propenylbenzene flavors and fragrances can be made andisolated in high yield and selectivity by using bifunctional catalyst 1, andthe heterogenized analogues. Multigram-scale reactions can be performed neat and the products isolated either by distillation, using homogeneous catalyst 1 (0.1-0.5 mol%, r.t., 10-45 min), or by decantation from heterogeneous catalysts PS-1 or PSL-1 (0.5 mol%, 70 degrees C, 24 h; catalyst separation and re-use shown for 3-4 cycles; 10 cycles using distilled eugenol feedstock). Both purified starting materials and essential oil feedstocks could be used. Z Isomers were present at very low levels (from 0.4% to less than 0.1%) in the products.

  (E)-丙烯基苯菲 synthetic 和分离可以高效、高选择性地通过双功能催化剂1以及异构物进行。多igram级反应可以在天然下进行，并且产物可以通过蒸馏（使用均匀催化剂1，0.1-0.5 mol%，室温，10-45分钟）或通过不均匀催化剂PS-1或PSL-1（0.5 mol%，70摄氏度，24小时；催化物分离和重新使用在3-4个循环中，10个循环使用蒸馏后的乙基琼脂醇环境）从不均匀催化剂中分离。这两种纯化后的基础材料和精油原料都可以使用。产物中Z异构体含量极低，从0.4%到低于0.1%。
• Palladium-Catalyzed Allylic C–H Oxidative Annulation for Assembly of Functionalized 2-Substituted Quinoline Derivatives
  作者：Chunsheng Li、Jianxiao Li、Yanni An、Jianwen Peng、Wanqing Wu、Huanfeng Jiang

  DOI：10.1021/acs.joc.6b01909

  日期：2016.12.16

  An efficient and practical palladium-catalyzed aerobic oxidative approach to afford functionalized 2-substituted quinolines in moderate to good yields from readily available allylbenzenes with aniline is developed. The present annulation process has high functional-group tolerance and high atom economy, making it a valuable and practical method in synthetic and medicinal chemistry. Moreover, this transformation

  开发了一种有效且实用的钯催化有氧氧化方法，可从容易获得的烯丙基苯与苯胺以中等至良好的产率提供官能化的2-取代的喹啉。目前的环形工艺具有较高的官能团耐受性和较高的原子经济性，使其成为合成和药物化学中有价值和实用的方法。此外，这种转变被认为是通过氧化烯丙基的C–H功能化而进行的，从而在一锅中形成C–C和C–N键。
• Comparing the Stereoselective Biooxidation of Cyclobutanones by Recombinant Strains Expressing Bacterial Baeyer–Villiger Monooxygenases
  作者：Florian Rudroff、Joanna Rydz、Freek H. Ogink、Michael Fink、Marko D. Mihovilovic

  DOI：10.1002/adsc.200700072

  日期：2007.6.4

  cyclobutanone structural motif was investigated using a collection of eight monooxygenases of different bacterial origin. This platform of enzymes is able to perform stereoselective biotransformations on an array of structurally diverse substrates. With several ketone precursors, biooxidations yielded enantiocomplementary butyrolactones as key intermediates for the synthesis of natural products and bioactive compounds

  使用八种不同细菌来源的单加氧酶，研究了具有环丁酮结构图案的代表性手性酮的微生物拜耶-维利格氧化。这种酶平台能够在一系列结构多样的底物上进行立体选择性生物转化。与几种酮前体一起，生物氧化产生对映体互补的丁内酯，作为合成天然产物和生物活性化合物的关键中间体。从头产生手性后，微生物的Baeyer-Villiger氧化作用可在脱对称反应中轻松快速地进入几种化合物类别。
• Cobalt-Catalyzed Trifluoromethylation–Peroxidation of Unactivated Alkenes with Sodium Trifluoromethanesulfinate and Hydroperoxide
  作者：Hong-Yu Zhang、Chao Ge、Jiquan Zhao、Yuecheng Zhang

  DOI：10.1021/acs.orglett.7b02353

  日期：2017.10.6

  herein is an unprecedented cobalt-catalyzed trifluoromethylation–peroxidation of unactivated alkenes. In this process the hydroperoxide acts as a radical initiator as well as a coupling partner. The cheap and readily available sodium trifluoromethanesulfinate serves as the CF3 source in the reaction. Various alkenes are transformed into vicinal trifluoromethyl-peroxide compounds in moderate to good yields

  本文公开了前所未有的钴催化的未活化烯烃的三氟甲基化-过氧化反应。在该过程中，氢过氧化物充当自由基引发剂以及偶联伴侣。廉价且容易获得的三氟甲烷亚磺酸钠在反应中用作CF 3来源。各种烯烃以中等至良好的产率转化为邻位的三氟甲基过氧化物化合物。

表征谱图