肉桂酸 | 621-82-9

• 物质功能分类: 香精与香料 - 合成香料 - 羧酸及酯类香料
• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 肉桂酸及其衍生物
• 中文名称: 肉桂酸
• 中文别名: beta-苯基丙烯酸；3-苯基丙烯酸；桂皮酸；肉桂酸(顺式)
• 英文名称: Cinnamic acid
• 英文别名: cinammic acid；phenylacrylic acid；3-phenylacrylic acid；cinnamoyl alcohol；trans-cinnamic acid；2-Propenoic acid, 3-phenyl-；3-phenylprop-2-enoic acid
• CAS: 621-82-9
• 化学式: C₉H₈O₂
• 分子量: 148.161
• InChiKey: WBYWAXJHAXSJNI-UHFFFAOYSA-N

物化性质

• 熔点：
  133 °C(lit.)
• 沸点：
  300 °C(lit.)
• 密度：
  1.2475
• 闪点：
  >230 °F
• 溶解度：
  可溶于氯仿（少许）、甲醇（少许）
• LogP：
  2.13
• 物理描述：
  White crystalline scales, honey floral odour
• 保留指数：
  1386;1396;1395;1394;1389.1;1394
• 稳定性/保质期：
  • 远离氧化物。
  • 存在于烟气中。

计算性质

• 辛醇/水分配系数(LogP)：
  2.1
• 重原子数：
  11
• 可旋转键数：
  2
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  37.3
• 氢给体数：
  1
• 氢受体数：
  2

安全信息

• 危险品标志：
  Xi
• 安全说明：
  S26,S36
• 危险类别码：
  R36/37/38
• WGK Germany：
  1
• 海关编码：
  2916190090
• 危险品运输编号：
  20kgs
• RTECS号：
  GD7850000
• 危险性防范说明：
  P261,P305+P351+P338
• 危险性描述：
  H315,H319,H335
• 储存条件：
  存放在密封容器中，并放置在阴凉、通风且干燥的地方，避免阳光直射。储存区域需远离氧化剂。

SDS

Name:	Cinnamic Acid Material Safety Data Sheet
Synonym:	Phenylacrylic acid; 3-Phenylacrylic acid; 3-Phenyl-2-propenoic acid
CAS:	621-82-9

Section 1 - Chemical Product MSDS Name:Cinnamic Acid Material Safety Data Sheet
Synonym:Phenylacrylic acid; 3-Phenylacrylic acid; 3-Phenyl-2-propenoic acid

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Section 2 - COMPOSITION, INFORMATION ON INGREDIENTS

CAS#	Chemical Name	content	EINECS#
621-82-9	Cinnamic Acid	100 %	210-708-3

Hazard Symbols: XI
Risk Phrases: 36/38

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Section 3 - HAZARDS IDENTIFICATION
EMERGENCY OVERVIEW
Irritating to eyes and skin.
Potential Health Effects
Eye:
Causes eye irritation.
Skin:
Causes skin irritation.
Ingestion:
Causes gastrointestinal irritation with nausea, vomiting and diarrhea.
Inhalation:
Causes respiratory tract irritation.
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 immediately.
Skin:
Immediately flush skin with plenty of water for at least 15 minutes while removing contaminated clothing and shoes. Get medical aid if irritation develops or persists.
Ingestion:
If victim is conscious and alert, give 2-4 cupfuls of milk or water.
Never give anything by mouth to an unconscious person. Get medical aid.
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.
Notes to Physician:

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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.
Extinguishing Media:
Use foam, dry chemical, or carbon dioxide.

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Section 6 - ACCIDENTAL RELEASE MEASURES
General Information: Use proper personal protective equipment as indicated in Section 8.
Spills/Leaks:
Vacuum or sweep up material and place into a suitable disposal container. Reduce airborne dust and prevent scattering by moistening with water. Clean up spills immediately, observing precautions in the Protective Equipment section.

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Section 7 - HANDLING and STORAGE
Handling:
Wash thoroughly after handling. Wash hands before eating. Use with adequate ventilation. Avoid contact with skin and eyes. Avoid ingestion and inhalation.
Storage:
Store in a cool, dry place. Store in a tightly closed container.

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Section 8 - EXPOSURE CONTROLS, PERSONAL PROTECTION
Engineering Controls:
Use adequate ventilation to keep airborne concentrations low.
Exposure Limits CAS# 621-82-9: 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: Solid
Color: white
Odor: Honey floral odor.
pH: Not available.
Vapor Pressure: Not available.
Viscosity: Not available.
Boiling Point: 300 deg C
Freezing/Melting Point: 133 deg C
Autoignition Temperature: Not applicable.
Flash Point: 212 deg F ( 100.00 deg C)
Explosion Limits, lower: Not available.
Explosion Limits, upper: Not available.
Decomposition Temperature: Not available.
Solubility in water: Insoluble in water.
Specific Gravity/Density: Not available.
Molecular Formula: C9H8O2
Molecular Weight: 148.0548

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Section 10 - STABILITY AND REACTIVITY
Chemical Stability:
Stable under normal temperatures and pressures.
Conditions to Avoid:
Incompatible materials.
Incompatibilities with Other Materials:
Strong oxidants.
Hazardous Decomposition Products:
Carbon monoxide, irritating and toxic fumes and gases, carbon dioxide.
Hazardous Polymerization: Has not been reported.

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Section 11 - TOXICOLOGICAL INFORMATION
RTECS#:
CAS# 621-82-9: GD7800000 LD50/LC50:
CAS# 621-82-9: Draize test, rabbit, skin: 500 mg/24H Mild; Oral, mouse: LD50 = 5 gm/kg; Oral, rat: LD50 = 2500 mg/kg.
Carcinogenicity:
Cinnamic Acid - Not listed by ACGIH, IARC, or NTP.
Other:
See actual entry in RTECS for complete information.

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Section 12 - ECOLOGICAL INFORMATION

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Section 13 - DISPOSAL CONSIDERATIONS
Products which are considered hazardous for supply are classified as Special Waste and the disposal of such chemicals is covered by regulations which may vary according to location. Contact a specialist disposal company or the local waste regulator for advice. Empty containers must be decontaminated before returning for recycling.

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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 36/38 Irritating to eyes and skin.
Safety Phrases:
S 26 In case of contact with eyes, rinse immediately
with plenty of water and seek medical advice.
S 28 After contact with skin, wash immediately
with...
WGK (Water Danger/Protection)
CAS# 621-82-9: 1
Canada
CAS# 621-82-9 is listed on Canada's DSL List.
CAS# 621-82-9 is not listed on Canada's Ingredient Disclosure List.
US FEDERAL
TSCA
CAS# 621-82-9 is listed on the TSCA inventory.

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SECTION 16 - ADDITIONAL INFORMATION
N/A

制备方法与用途

理化性质

肉桂酸亦称桂皮酸、亚苄基乙酸或3-苯基-2-丙烯酸，是一种不饱和芳香酸。它具有微弱的桂皮香气，并以游离或酯的形式存在于凤仙花、桂皮油与古柯叶中。由于含有双键，肉桂酸有顺式和反式的两种异构体，其中顺式体存在三种同质多晶体。顺式和反式异构体在自然界均有分布，反式存在于苏合香脂、桂皮油、秘鲁香脂、罗勒油及可可叶等精油中；而顺式则主要存在于马六甲良姜油中。市售肉桂酸多为反式。

肉桂酸的相对分子质量为148.17。顺式的别肉桂酸第一种晶型在水中析出后，呈现单斜晶系，无色至白色棱柱状结晶；其相对密度为1.284（4℃），熔点为42℃，沸点分别为265℃（分解）和125℃（2.533×10^3 Pa）。顺式肉桂酸微溶于水，在25℃时溶解度为0.937 g/100 mL，易溶于乙醇、乙醚和乙酸乙酯。

顺式的第二种晶型α-异肉桂酸从石油英中析出后，同样呈现单斜晶系无色至白色棱柱状晶体；其熔点为58℃，沸点265℃。它在乙醇、乙酸、氯仿和丙酮中的溶解度良好，并且易溶于乙醚、丙酮、冰醋酸及油类。

顺式的第三种晶型β-异肉桂酸也呈现单斜晶系无色至白色棱柱状晶体；其熔点为45℃，沸点268.9℃。它在乙醇和氯仿中的溶解度较好，并易溶于乙醚、丙酮、冰醋酸及油类。

反式肉桂酸的溶解性与顺式相似，但相对密度较低（约1.30 g/cm^3），熔点约为45-62℃。它在乙醇和氯仿中的溶解度较好，并易溶于乙醚、丙酮、冰醋酸及油类。

含量分析

准确称取预先在盛有硅胶的干燥器中干燥过3小时后的试样500 mg，加入预经用0.1 mol/L氢氧化钠溶液处理的水进行滴定。通过此方法可以测定肉桂酸的含量。

毒性

GRAS（一般认为安全）（FEMA）。LD₅₀ 2500 mg/kg（大鼠，经口）

使用限量

• FEMA(mg/kg)：软饮料31；冷饮40；糖果30；焙烤食品36；胶姆糖10。
• 适度为限（FDA§172.515，2000）

化学性质

肉桂酸为白色单斜棱晶。微有桂皮香气。易溶于乙醇、甲醇、石油醚、氯仿，亦易溶于苯、乙醚、丙酮、冰醋酸及二硫化碳和油类，而不溶于水。

用途

主要用于制备酯类、香料和医药原料。

生产方法

1. 由氯化苄与醋酸钠共热而得
2. 苯甲醛与乙酸钠(或乙酸钾)在脱氢剂醋酐存在下共热而得
3. 将苯甲烯丙酮、碳酸钠和漂白粉混合，生成的桂酸钠再用硫酸处理而得

以上生产方法均适用于制备肉桂酸。

反应信息

• 作为反应物：
  描述：

  肉桂酸 在 potassium chlorate 、 乙醇 、 氯 作用下， 生成 2-chloro-3-hydroxy-3-phenyl-propionic acid
  参考文献：
  名称：

  Jackson; Pasiut, Journal of the American Chemical Society, 1927, vol. 49, p. 2078

  摘要：

  DOI：
• 作为产物：
  描述：

  肉桂醛 在 氧气 作用下， 90.0 ℃ 、500.01 kPa 条件下， 反应 5.0h， 生成 肉桂酸
  参考文献：
  名称：

  连续流中连续双催化剂床上的级联好氧选择性氧化

  摘要：

  级联反应代表了一种原子经济且节能的技术，可减少化学制造所需的操作次数。生物催化级联在自然界无处不在。然而，控制反应物，中间体和活性位点之间相互作用的顺序仍然是化学催化的挑战。在这里，我们演示了一种通过流化法使用化学催化剂实现高效级联的方法。在连续流动操作下，双床配置中的Pd / SBA-15和Pt / SBA-15非均相催化剂的紧密偶联可提供84％的高单程收率（比批处理操作提高20倍），并且对于>肉桂醇向肉桂酸的级联氧化反应中有14000的周转率，尽管两种催化剂对该反应均没有活性。Pd（第一床）和Pt（第二床）催化剂的合理排序对于促进不希望的加氢和氢解反应的级联氧化至关重要，后者优于逆流床顺序或单个混合的PdPt反应器床。每个床的固有催化性能都保留在最佳的双床配置中，从而能够定量预测其单独氧化行为已建立的反应物/中间体的最终产品收率。使用连续的反应器床进行连续处理可实现采用“简单”催化剂的

  DOI：

  10.1021/acscatal.9b00092
• 作为试剂：
  描述：

  N-甲酰吗啉 、 4-氯苯硫酚 在 copper diacetate 、 肉桂酸 、 copper(l) chloride 作用下， 反应 24.0h， 以68%的产率得到4-(4-氯苯基)磺酰吗啉
  参考文献：
  名称：

  Copper-mediated S–N formation via an oxygen-activated radical process: a new synthesis method for sulfonamides

  摘要：

  通过氧活化的自由基过程，已开发出一种铜介导的磺胺酰胺的直接合成。

  DOI：

  10.1039/c4cc01353k

文献信息

• Convenient Preparation of Primary Amides via Activation of Carboxylic Acids with Ethyl Chloroformate and Triethylamine under Mild Conditions
  作者：Takuya Noguchi、Masahiro Sekine、Yuki Yokoo、Seunghee Jung、Nobuyuki Imai

  DOI：10.1246/cl.130096

  日期：2013.6.5

  Primary amides were easily prepared in 22–99% yields from the corresponding carboxylic acids 1 or 5 with NH4Cl via activation with ClCO2Et and Et3N. The enantiomers of the corresponding primary ami...

  通过用 ClCO2Et 和 Et3N 活化，用 NH4Cl 从相应的羧酸 1 或 5 中很容易以 22-99% 的产率制备伯酰胺。相应伯胺的对映体...
• Mild reduction of carboxylic acids to alcohols using cyanuric chloride and sodium borohydride
  作者：Massimo Falorni、Andrea Porcheddu、Maurizio Taddei

  DOI：10.1016/s0040-4039(99)00734-0

  日期：1999.6

  Several carboxylic acids, including N-Boc, N-Cbz and N-Fmoc amino acids were reduced to the corresponding alcohols by activation of the carboxy function with cyanuric chloride and N-methylmorpholine followed by reduction with aqueous sodium borohydride.

  通过用氰尿酰氯和N-甲基吗啉活化羧基官能团，然后用硼氢化钠水溶液还原，将包括N -Boc，N -Cbz和N -Fmoc氨基酸在内的几种羧酸还原为相应的醇。
• 一种利用嘧啶类缩合剂点击构建酰胺键的方法及其在酰胺和多肽合成中的应用
  申请人：兰州大学

  公开号：CN112851536B

  公开（公告）日：2022-02-25

  本发明公开了一种利用嘧啶类缩合剂点击构建酰胺键的方法及其在酰胺和多肽合成中的应用。其中，酰胺键的构建方法为：在羧酸组分和胺组分中加入溶有有机碱的有机溶剂，搅拌反应后加入溶有嘧啶类缩合剂的有机溶剂，继续搅拌反应后浓缩、分离纯化，得到酰胺或多肽产物。本发明酰胺键构建方法缩合剂使用量少，且缩合剂本身安全无味易储存，具有很好的原子经济性。所述酰胺键构建反应时间仅需数秒至十分钟，极大地缩短了酰胺或多肽合成时间。另外，本发明酰胺键构建反应也可在有机相‑水相的双相体系，以及在有机相‑水相的双相体系和不添加碱的条件下也能快速发生，这为对碱敏感的生物体系中的酰胺键构建反应提供了一种温和可行的路径。
• New and simple synthesis of acid azides, ureas and carbamates from carboxylic acids: application of peptide coupling agents EDC and HBTU
  作者：Vommina V. Sureshbabu、H. S. Lalithamba、N. Narendra、H. P. Hemantha

  DOI：10.1039/b920290k

  日期：——

  Conversion of carboxylic acids into acid azides using peptide coupling agents, EDC and HBTU is described. The procedure is efficient, practical and applicable to a diverse range of carboxylic acids including N-protected amino acids. Using the same reagents, one-pot synthesis of ureas, dipeptidyl urea esters and carbamates from acids has also been achieved.

  使用肽偶联剂，EDC和 HBTU描述。该程序高效，实用并且适用于多种羧酸，包括ñ保护的氨基酸。使用相同的试剂，还可以从酸一锅合成尿素，二肽基脲酯和氨基甲酸酯。
• An efficient mechanochemical synthesis of amides and dipeptides using 2,4,6-trichloro-1,3,5-triazine and PPh₃
  作者：Chuthamat Duangkamol、Subin Jaita、Sirilak Wangngae、Wong Phakhodee、Mookda Pattarawarapan

  DOI：10.1039/c5ra10127a

  日期：——

  mechanochemical synthesis of amides from carboxylic acids has been developed through an in situ acid activation with 2,4,6-trichloro-1,3,5-triazine and a catalytic amount of PPh3. Under room temperature solvent-drop grinding of the reactants in the presence of an inorganic base, a variety of carboxylic acids including aromatic acids, aliphatic acids, and N-protected α-amino acids undergo amidation to afford

  通过用2,4,6-三氯-1,3,5-三嗪和催化量的PPh 3进行原位酸活化，已经开发了从羧酸快速，简便而有效的机械化学合成酰胺的方法。在室温下，在无机碱的存在下，对反应物进行溶剂滴磨，使包括芳族酸，脂族酸和N-保护的α-氨基酸在内的各种羧酸酰胺化，以中等至极好的收率得到酰胺。该方法还与Fmoc，Cbz和Boc保护基兼容，可产生受保护的旋光二肽而没有可检测的消旋作用。

表征谱图