反-4-癸烯醛 | 65405-70-1

• 物质功能分类: 化学试剂 - 有机试剂 - 脂肪醛（含缩醛，半缩醛）
• 分子结构分类: 有机化合物 - 有机氧化合物
• 中文名称: 反-4-癸烯醛
• 中文别名: 反-4-癸醛
• 英文名称: trans-4-decenal
• 英文别名: (E)-4-Decenal；(E)-dec-4-enal；(4E)-decenal；4-trans-decenal；trans-dec-4-enal；trans-4-Decen-1-al
• CAS: 65405-70-1
• 化学式: C₁₀H₁₈O
• 分子量: 154.252
• InChiKey: CWRKZMLUDFBPAO-VOTSOKGWSA-N

物化性质

• 沸点：
  90-100 °C (15 mmHg)
• 密度：
  0.842
• 闪点：
  78 °C
• LogP：
  3.5 at 35℃ and pH7
• 表面张力：
  55.1mN/m at 69mg/L and 20℃
• 物理描述：
  colourless to slightly yellow liquid with an orange-like, fatty odour
• 溶解度：
  soluble in alcohol and most fixed oils; insoluble in water
• 折光率：
  1.442-1.447
• 保留指数：
  1171;1172
• 稳定性/保质期：
  远离氧化物。

计算性质

• 辛醇/水分配系数(LogP)：
  3.1
• 重原子数：
  11
• 可旋转键数：
  7
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.7
• 拓扑面积：
  17.1
• 氢给体数：
  0
• 氢受体数：
  1

安全信息

• TSCA：
  Yes
• 危险品标志：
  Xi
• 安全说明：
  S24/25,S26,S37/39
• 危险类别码：
  R36/37/38
• 储存条件：
  存放在密封容器内并冷藏。储存时请远离氧化剂。

SDS

Name:	trans-4-Decenal Material Safety Data Sheet
Synonym:	None Known
CAS:	65405-70-1

Section 1 - Chemical Product MSDS Name:trans-4-Decenal Material Safety Data Sheet
Synonym:None Known

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Section 2 - COMPOSITION, INFORMATION ON INGREDIENTS

CAS#	Chemical Name	content	EINECS#
65405-70-1	trans-4-Decenal	ca. 100	265-741-6

Hazard Symbols: XI
Risk Phrases: 36/37/38

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Section 3 - HAZARDS IDENTIFICATION
EMERGENCY OVERVIEW
Irritating to eyes, respiratory system and skin.
Potential Health Effects
Eye:
Causes eye irritation. May cause chemical conjunctivitis.
Skin:
Causes skin irritation. May be harmful if absorbed through the skin.
Ingestion:
May cause gastrointestinal irritation with nausea, vomiting and diarrhea. May be harmful if swallowed.
Inhalation:
Causes respiratory tract irritation. May be harmful if inhaled. Can produce delayed pulmonary edema.
Chronic:
No information found.

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Section 4 - FIRST AID MEASURES
Eyes: Immediately flush eyes with plenty of water for at least 15 minutes, occasionally lifting the upper and lower eyelids. Get medical aid.
Skin:
Get medical aid. Flush skin with plenty of water for at least 15 minutes while removing contaminated clothing and shoes. Wash clothing before reuse.
Ingestion:
Never give anything by mouth to an unconscious person. Get medical aid. Do NOT induce vomiting. If conscious and alert, rinse mouth and drink 2-4 cupfuls of milk or water.
Inhalation:
Remove from exposure and move to fresh air immediately. If not breathing, give artificial respiration. If breathing is difficult, give oxygen. Get medical aid. Do NOT use mouth-to-mouth resuscitation.
Notes to Physician:
Treat symptomatically and supportively.

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Section 5 - FIRE FIGHTING MEASURES
General Information:
As in any fire, wear a self-contained breathing apparatus in pressure-demand, MSHA/NIOSH (approved or equivalent), and full protective gear. During a fire, irritating and highly toxic gases may be generated by thermal decomposition or combustion. Will burn if involved in a fire. Vapors may be heavier than air. They can spread along the ground and collect in low or confined areas. Runoff from fire control or dilution water may cause pollution. Combustible liquid and vapor.
Extinguishing Media:
Use water spray to cool fire-exposed containers. Use water spray, dry chemical, carbon dioxide, or appropriate foam.

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Section 6 - ACCIDENTAL RELEASE MEASURES
General Information: Use proper personal protective equipment as indicated in Section 8.
Spills/Leaks:
Absorb spill with inert material (e.g. vermiculite, sand or earth), then place in suitable container. Avoid runoff into storm sewers and ditches which lead to waterways. Clean up spills immediately, observing precautions in the Protective Equipment section. Remove all sources of ignition. Use a spark-proof tool. Provide ventilation.

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Section 7 - HANDLING and STORAGE
Handling:
Wash thoroughly after handling. Avoid contact with eyes, skin, and clothing. Empty containers retain product residue, (liquid and/or vapor), and can be dangerous. Keep container tightly closed. Avoid ingestion and inhalation. Use with adequate ventilation. Wash clothing before reuse. Do not pressurize, cut, weld, braze, solder, drill, grind, or expose empty containers to heat, sparks or open flames. Keep away from heat and flame.
Storage:
Keep away from sources of ignition. Store in a tightly closed container. Store in a cool, dry, well-ventilated area away from incompatible substances.

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Section 8 - EXPOSURE CONTROLS, PERSONAL PROTECTION
Engineering Controls:
Facilities storing or utilizing this material should be equipped with an eyewash facility and a safety shower. Use adequate ventilation to keep airborne concentrations low.
Exposure Limits CAS# 65405-70-1: Personal Protective Equipment Eyes: Wear appropriate protective eyeglasses or chemical safety goggles as described by OSHA's eye and face protection regulations in 29 CFR 1910.133 or European Standard EN166.
Skin:
Wear appropriate protective gloves to prevent skin exposure.
Clothing:
Wear appropriate protective clothing to prevent skin exposure.
Respirators:
Follow the OSHA respirator regulations found in 29 CFR 1910.134 or European Standard EN 149. Use a NIOSH/MSHA or European Standard EN 149 approved respirator if exposure limits are exceeded or if irritation or other symptoms are experienced.

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Section 9 - PHYSICAL AND CHEMICAL PROPERTIES

Physical State: Liquid
Color: colorless
Odor: Not available.
pH: Not available.
Vapor Pressure: Not available.
Viscosity: Not available.
Boiling Point: 90-100 deg C @ 15mmHg
Freezing/Melting Point: Not available.
Autoignition Temperature: Not available.
Flash Point: 78 deg C ( 172.40 deg F)
Explosion Limits, lower: Not available.
Explosion Limits, upper: Not available.
Decomposition Temperature:
Solubility in water:
Specific Gravity/Density: 0.842
Molecular Formula: C10H18O
Molecular Weight: 154.25

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Section 10 - STABILITY AND REACTIVITY
Chemical Stability:
Stable at room temperature in closed containers under normal storage and handling conditions.
Conditions to Avoid:
Ignition sources, excess heat.
Incompatibilities with Other Materials:
Strong oxidizing agents, strong bases.
Hazardous Decomposition Products:
Carbon monoxide, carbon dioxide.
Hazardous Polymerization: Has not been reported

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Section 11 - TOXICOLOGICAL INFORMATION
RTECS#:
CAS# 65405-70-1 unlisted.
LD50/LC50:
Not available.
Carcinogenicity:
trans-4-Decenal - Not listed by ACGIH, IARC, or NTP.

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Section 12 - ECOLOGICAL INFORMATION

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Section 13 - DISPOSAL CONSIDERATIONS
Dispose of in a manner consistent with federal, state, and local regulations.

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Section 14 - TRANSPORT INFORMATION

IATA
Not regulated as a hazardous material.
IMO
Not regulated as a hazardous material.
RID/ADR
Not regulated as a hazardous material.

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Section 15 - REGULATORY INFORMATION

European/International Regulations
European Labeling in Accordance with EC Directives
Hazard Symbols: XI
Risk Phrases:
R 36/37/38 Irritating to eyes, respiratory system
and skin.
Safety Phrases:
WGK (Water Danger/Protection)
CAS# 65405-70-1: No information available.
Canada
CAS# 65405-70-1 is listed on Canada's DSL List.
CAS# 65405-70-1 is not listed on Canada's Ingredient Disclosure List.
US FEDERAL
TSCA
CAS# 65405-70-1 is listed on the TSCA inventory.

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SECTION 16 - ADDITIONAL INFORMATION
N/A

制备方法与用途

食品添加剂最大允许使用量与最大允许残留量标准 添加剂信息表

• 添加剂中文名称: 4-癸烯醛
• 允许使用该种添加剂的食品中文名称: 食品
• 添加剂功能: 食品用香料
• 最大允许使用量（g/kg）: 用于配制香精的各香料成分不得超过在GB 2760中的最大允许使用量和最大允许残留量

以上信息仅供参考，具体标准请以官方文件为准。

反应信息

• 作为反应物：
  描述：

  反-4-癸烯醛 在 盐酸 、 sodium chlorite 、 sodium dihydrogenphosphate 、 AD-mix-α 、 2-甲基-2-丁烯 、 甲基磺酰胺 作用下， 以 二氯甲烷 、 水 、 叔丁醇 为溶剂， 反应 18.0h， 生成 (4S,5S)-4,5-dihydroxydecanoic acid γ-lactone
  参考文献：
  名称：

  酿酒酵母中氘代同构6,7-二羟基十二酸的代谢-5-羟基癸烷-4-内酯（= 4,5-二氢-5-（1-羟基己基）呋喃-2（3 H）的非对映和对映选择性形成及表征）-一）异构体

  摘要：

  研究了氘化的6,7-二羟基十二烷酸甲酯1的化学合成以及随后在啤酒酵母液体培养物中酯1和相应酸1a的代谢。孵育实验用（6 - [R，7 - [R ）-或（6小号，7小号）-6,7-二羟基（6,7- 2 ħ 2）十二烷酸甲基酯（（6 - [R，7 - [R ）-或（6 S，7 S）-（6,7- 2 H 2）-1（分别）和（±）-苏式-或（±）-赤型-6,7-二羟基（6,7- 2 H 2）十二酸（（±）-苏--或（±）-赤型-（6,7- 2 H 2）-1a，分别阐明了它们在酵母中的代谢途径（表1-3）。主要产品是异构体2 H标记的5-羟基癸基-4-内酯2。四个异构体的内酯的绝对构型2是由化学合成分配经由夏普勒斯不对称二羟基化和手性气相色谱法（Lipodex  ® ë）。苏式对映体- 2而不会对衍生分离Lipodex  ® È ; 与此相反，对映体赤- 2只能变换之后被分离到其5- ø - （三氟乙酰基）衍生物。甲酯的生物转化（6

  DOI：

  10.1002/hlca.200390189
• 作为产物：
  描述：

  (2E,4E)-2,4-癸二烯醇 在 H₂ activated rhodium-phosphinine complex 作用下， 以 1,4-二氧六环 为溶剂， 反应 12.0h， 生成 反-4-癸烯醛
  参考文献：
  名称：

  铑-膦配合物催化烯丙醇转位为羰基化合物

  摘要：

  通过包含铑和三取代膦（磷苯衍生物）的新催化剂体系，各种烯丙醇的异构化以及相应的饱和羰基化合物的形成很容易实现，尤其是当Rh配合物在转座反应之前被氢气活化时。

  DOI：

  10.1055/s-2006-948180

文献信息

• Catalytic Hydroetherification of Unactivated Alkenes Enabled by Proton‐Coupled Electron Transfer
  作者：Elaine Tsui、Anthony J. Metrano、Yuto Tsuchiya、Robert R. Knowles

  DOI：10.1002/anie.202003959

  日期：2020.7.13

  We report a catalytic, light‐driven method for the intramolecular hydroetherification of unactivated alkenols to furnish cyclic ether products. These reactions occur under visible‐light irradiation in the presence of an IrIII‐based photoredox catalyst, a Brønsted base catalyst, and a hydrogen‐atom transfer (HAT) co‐catalyst. Reactive alkoxy radicals are proposed as key intermediates, generated by direct

  我们报告了一种催化光驱动方法，用于未活化烯醇的分子内加氢醚化以提供环醚产品。这些反应在 Ir III基光氧化还原催化剂、布朗斯台德碱催化剂和氢原子转移 (HAT) 助催化剂存在下在可见光照射下发生。反应性烷氧基被认为是关键中间体，是通过质子耦合电子转移机制直接均裂激活醇 O−H 键而产生的。该方法表现出广泛的底物范围和高官能团耐受性，并且适应多种烯烃取代模式。还提出了证明该催化系统扩展到碳醚化反应的结果。
• Magnesium Nitride as a Convenient Source of Ammonia: Preparation of Dihydropyridines
  作者：Katy L. Bridgwood、Gemma E. Veitch、Steven V. Ley

  DOI：10.1021/ol801399w

  日期：2008.8.21

  Magnesium nitride (Mg 3N 2) has been investigated for the preparation of dihydropyridines. This is a commercially available, bench-stable solid that generates ammonia upon treatment with protic solvents. The main features of the process are the facile reaction setup and good yields obtained in the majority of cases.

  已经研究了氮化镁（Mg 3N 2）用于制备二氢吡啶。这是一种可从市场上买到的，板凳稳定的固体，在用质子溶剂处理后会生成氨。该方法的主要特点是反应设置简便，在大多数情况下均能获得良好的收率。
• 一种反-4-癸烯醛的合成方法
  申请人：云南博淇科技有限公司

  公开号：CN107011136B

  公开（公告）日：2023-03-03

  本发明公开了一种高端香料反‑4‑癸烯醛的化学合成方法。以5溴‑反4‑戊烯醛为起始原料，保护醛基后与正戊基溴化镁发生交叉偶联反应得到反‑4‑癸烯醛二甲醇缩醛，解保护后得到反‑4‑癸烯醛。本发明的优点是原料廉价易得，合成路线简单，反应条件温和，操作便利安全，产率高，成本低，易于工业化生产。
• Mechanistic Dichotomy in CpRu(CH₃CN)₃PF₆ Catalyzed Enyne Cycloisomerizations
  作者：Barry M. Trost、F. Dean Toste

  DOI：10.1021/ja012450c

  日期：2002.5.1

  Enynes are easily accessible building blocks as a result of the rich chemistry of alkynes and thus represent attractive substrates for ring formation. A ruthenium catalyst for cycloisomerization effects such reaction of 1,6- and 1,7-enynes typically at room temperature in acetone or DMF under neutral conditions. The reaction is effective for forming five- and six-membered rings of widely divergent

  由于炔烃的丰富化学性质，炔烃很容易获得结构单元，因此是形成环的有吸引力的底物。用于环异构化的钌催化剂通常在室温下在丙酮或 DMF 中在中性条件下实现 1,6- 和 1,7- 烯炔的此类反应。该反应可有效形成具有广泛发散结构的五元和六元环。炔烃可以带有供选和退选取代基。烯烃可以是二或三取代的。然而，在炔酸的炔丙基位置引入四元中心完全改变了反应的性质。在 1,6-烯酸酯的情况下，在同样温和的条件下以优异的产率形成七元环。提供的证据表明机制发生了完全变化。在前一种情况下，反应涉及钌环戊烯的中间体。在后一种情况下，提出了一个 CH 插入以形成 π-烯丙基钌中间体，并且...
• Isolable and Readily Handled Halophosphonium Pre-reagents for Hydro- and Deuteriohalogenation
  作者：Florian T. Schevenels、Minxing Shen、Scott A. Snyder

  DOI：10.1021/jacs.6b12653

  日期：2017.5.10

  and acid-sensitive moieties, particularly polyenes prone to cyclization. The process is also challenging when conducted on a small scale, and moreover, methods for the addition of their deuterated counterparts typically require special techniques, especially when control of stoichiometry is required. Herein is described a readily synthesized and handled reagent class which can accomplish the controlled

  尽管对跨烯烃添加酰卤进行了充分研究，但许多具有离去基团、多不饱和度和酸敏感部分的底物类别仍然存在局限性，特别是易于环化的多烯。该过程在小规模进行时也具有挑战性，此外，添加氘代对应物的方法通常需要特殊技术，尤其是在需要控制化学计量时。本文描述了一种易于合成和处理的试剂类，它可以在耐受不同功能的温和反应条件下，完成 HCl 和 HBr 跨几个烯烃类的受控和选择性马尔可夫尼科夫加成。该过程在实验室规模上特别有价值，并提供了与其他方法的直接比较。

表征谱图