4-羟基肉桂酸甲酯 | 3943-97-3

• 物质功能分类: 香精与香料 - 合成香料 - 芳香肉桂酸、酯及衍生物
• 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: 4-羟基肉桂酸甲酯
• 中文别名: 对羟基(苯基)丙烯酸甲酯；对羟基肉桂酸甲酯
• 英文名称: methyl p-hydroxycinnamate
• 英文别名: methyl 4-hydroxycinnamate；methyl p-coumarate；3-(4-hydroxyphenyl)-2-propenoic acid methyl ester；p-coumaric acid methyl ester；2-Propenoic acid, 3-(4-hydroxyphenyl)-, methyl ester；methyl 3-(4-hydroxyphenyl)prop-2-enoate
• CAS: 3943-97-3
• 化学式: C₁₀H₁₀O₃
• mdl: MFCD00157167
• 分子量: 178.188
• InChiKey: NITWSHWHQAQBAW-UHFFFAOYSA-N

物化性质

• 熔点：
  144-145°
• 沸点：
  306.6±17.0 °C(Predicted)
• 密度：
  1?+-.0.06 g/cm3(Predicted)
• LogP：
  1.88 at 25℃

计算性质

• 辛醇/水分配系数(LogP)：
  2.3
• 重原子数：
  13
• 可旋转键数：
  3
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.1
• 拓扑面积：
  46.5
• 氢给体数：
  1
• 氢受体数：
  3

安全信息

• 危险等级：
  IRRITANT
• 海关编码：
  2918290000
• 危险性防范说明：
  P261,P280,P305+P351+P338
• 危险性描述：
  H302,H315,H319,H332,H335
• 储存条件：
  室温

SDS

Material Safety Data Sheet

---

Section 1. Identification of the substance
Product Name: Methyl 4-hydroxycinnamate
Synonyms:

---

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

---

Section 3. Composition/information on ingredients.
Ingredient name: Methyl 4-hydroxycinnamate
CAS number: 3943-97-3

---

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.

---

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.

---

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.

---

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:

---

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.

---

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: C10H10O3
Molecular weight: 178.2

---

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

---

Section 11. Toxicological information
No data.

---

Section 12. Ecological information
No data.

---

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.

---

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

---

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.

---

SECTION 16 - ADDITIONAL INFORMATION
N/A

制备方法与用途

生物活性

Methyl p-coumarate（甲基对香豆酸，Methyl 4-hydroxycinnamate），是从 Trixis michuacana var. longifolia 的花朵中分离出的一种对香豆酸 (pCA) 的酯化衍生物。这种化合物能够抑制 B16 小鼠黑素瘤细胞中黑色素的形成，并且在体外表现出强大的抑菌作用，尤其对抗链格孢菌和其他病原体具有显著效果。

反应信息

• 作为反应物：
  描述：

  4-羟基肉桂酸甲酯 在 silver(l) oxide 作用下， 以 丙酮 、 苯 为溶剂， 反应 20.0h， 以34%的产率得到(±)-trans-dehydrodicoumaric acid dimethyl ester
  参考文献：
  名称：

  二氢苯并呋喃新木脂素的杀血吸虫活性

  摘要：

  我们已经评估了合成的二氢苯并呋喃新木脂素 (DBN) 的抗血吸虫活性，这些物质来自 (±)-反式-脱氢二香豆酸二甲酯 (1) 和 (±)-反式-脱氢二阿魏酸二甲酯 (2)，体外对成年曼氏血吸虫蠕虫的抗血吸虫活性。化合物4（(±)-trans-4-O-乙酰脱氢二阿魏酸二甲酯）表现出最有希望的活性；在 200 μm，它在 24 小时后杀死 100 ± 0% 的蠕虫，这类似于使用吡喹酮（阳性对照）在 1.56 μm 处获得的结果。C7'和C8'之间双键的氢化、C3'处额外甲基的引入以及C7和C8之间的双键降低了DBNs的杀血吸虫活性。另一方面，C4 处乙酰氧基的存在在该活动中起到了有趣的作用。

  DOI：

  10.1002/cbdv.201800134
• 作为产物：
  描述：

  4-香豆酸 在 氯化亚砜 作用下， 生成 4-羟基肉桂酸甲酯
  参考文献：
  名称：

  Meyer,H., Monatshefte fur Chemie, 1901, vol. 22, p. 433

  摘要：

  DOI：

文献信息

• METHOD FOR PRODUCING A CROSS-COUPLING PRODUCT OF A BENZENOID DIAZONIUM SALT
  申请人：Boege Nicolas

  公开号：US20130053598A1

  公开（公告）日：2013-02-28

  The invention relates to a method for producing a cross-coupling product of a benzenoid dizonium salt according to the general formula (I), wherein the groups R 1 , R 2 , R 3 , R 4 , and R 5 represent hydrogen, halogen, an alkyl, alkenyl, aryl, alkoxy, aryloxy, nitro, cyano, hydroxy, acetyl, and/or diazo groups independently of each, and X represents BF 4 , Cl, F, SO 3 CH 3 , CO 2 CH 3 , PF 6 , ClO 2 CH 3 , or CIO 4 , comprising the following steps: (a) providing a benzenoid amide, which with the exception of the diazo function has the same substituents R 1 , R 2 , R 3 , R 4 , and R 5 as the benzenoid diazonium salt of the general formula (I), and hydrolytically cleaving the amide to form an amine or providing a corresponding amine, (b) diazotizing the amine thus obtained or provided with a nitrite, and (c) subsequently reacting the benzenoid diazonium salt with a coupling partner in the presence of a catalyst to form a cross-coupling product, wherein the coupling parter is represented by the general formula (II), R 6 , R 7 , and R 8 are the same or different and represent hydrogen, carboxyalkyl groups, carboxyaryl groups, alkyl groups, aryl groups, alkoxy groups, aryloxy groups, wherein the groups can each contain Si, N, S, O, and or halogen atoms, or R 6 and R 7 with the double bound form an aromatic ring, which can be provided with R 8 and one to four further substituents, independently of each other, selected from the group comprising a straight-chain or branched (C 1 -C 6 ) alkyl group, a (C 3 -C 7 ) cycloalkyl group, a straight-chain or branched (C 1 -C 6 ) alkenyl group, a straight-chain or branched (C 1 -C 6 ) alkyoxy group, halogen, the hydroxy group, an amino, di(C 1 -C 6 ) alkylamino, nitro, acetyl, cyan, benzyl, 4-methoxybenzyl, 4-nitrobenzyl, phenyl, and 4-methoxyphenyl group and represents Y=H, —B(OR) 2 , —SnR 3 , —ZnR, —SiR 3 , or Mg (halogen), and wherein at least the steps (b) and (c) are performed without intermediate isolation of an intermediate product. According to said method, cross-couplings can be performed more simply and with improved yield without the hydroxyl group in aromatic reactants containing hydroxyl groups having to be provided with a protective group.

  该发明涉及一种根据通式(I)制备苯并重氮盐的交叉偶联产物的方法，其中基团R1、R2、R3、R4和R5代表氢、卤素、烷基、烯基、芳基、烷氧基、芳氧基、硝基、氰基、羟基、乙酰基和/或重氮基，X代表BF4、Cl、F、SO3CH3、CO2CH3、PF6、ClO2CH3或CIO4，包括以下步骤：(a)提供苯并酰胺，除了重氮功能外，具有通式(I)中苯并重氮盐相同的取代基R1、R2、R3、R4和R5，并水解裂解酰胺形成胺或提供相应的胺，(b)用亚硝酸盐重氮得到或提供的胺，(c)随后在催化剂存在下将苯并重氮盐与偶联配体反应形成交叉偶联产物，其中偶联配体由通式(II)表示，R6、R7和R8相同或不同，代表氢、羧基烷基、羧基芳基、烷基、芳基、烷氧基、芳氧基，其中基团可以包含Si、N、S、O和/或卤素原子，或R6和R7与双键形成芳香环，可提供R8和一个到四个进一步取代基，独立于彼此，选自包括直链或支链(C1-C6)烷基、(C3-C7)环烷基、直链或支链(C1-C6)烯基、直链或支链(C1-C6)烷氧基、卤素、羟基、氨基、二(C1-C6)烷基氨基、硝基、乙酰基、氰基、苄基、4-甲氧基苄基、4-硝基苄基、苯基和4-甲氧基苯基，表示Y=H、—B(OR)2、—SnR3、—ZnR、—SiR3或Mg(卤素)，至少步骤(b)和(c)在不中间分离中间产物的情况下执行。根据该方法，可以更简单地进行交叉偶联，并且在含有羟基的芳香反应物中无需提供保护基即可获得改进的产率。
• [EN] BIVALENT LECA INHIBITORS TARGETING BIOFILM FORMATION OF PSEUDOMONAS AERUGINOSA<br/>[FR] INHIBITEURS BIVALENTS DE LECA CIBLANT LA FORMATION DE BIOFILM DE PSEUDOMONAS AERUGINOSA
  申请人：HELMHOLTZ ZENTRUM INFEKTIONSFORSCHUNG GMBH

  公开号：WO2021089729A1

  公开（公告）日：2021-05-14

  The present invention relates to divalent compounds binding to LecA. The compounds are useful to block biofilm formation of Pseudomonas aeruginosa. The invention further relates to pharmaceutical compositions comprising these compounds and to therapeutic methods and uses of these compounds, in particular to therapeutic methods and uses for the treatment of Pseudomonas aeruginosa infections in a subject. The invention also relates to imaging of infections, such as biofilms produced by Pseudomonas aeruginosa, by using these divalent compounds.

  本发明涉及与LecA结合的二价化合物。这些化合物可用于阻断铜绿假单胞菌的生物膜形成。该发明还涉及包含这些化合物的药物组合物，以及这些化合物的治疗方法和用途，特别是用于治疗受铜绿假单胞菌感染的受试者的治疗方法和用途。该发明还涉及使用这些二价化合物来成像感染，例如通过使用这些二价化合物来成像铜绿假单胞菌产生的生物膜。
• 一种镍催化的烯烃不对称氢炔基化方法及在制备AMG837中的应用
  申请人：南京大学

  公开号：CN112679290B

  公开（公告）日：2022-03-15

  本发明公开了一种镍催化的烯烃不对称氢炔基化的方法及在制备AMG837中的应用，属于有机化学和药物化学领域。本发明在金属镍盐、手性配体、碱、氢源、添加剂等作用下，使烯烃与炔基溴化合物在有机溶剂中进行反应，以优秀的区域选择性和对映选择性得到苄位炔基取代的化合物。本发明方法使用廉价的过渡金属镍作为催化剂，使用商业可得的烯烃和炔基溴化物为原料，条件温和，官能团兼容性好，操作简便。
• Organic amine mediated cleavage of C_aromatic–C_α bonds in lignin and its platform molecules
  作者：Yu Xin、Xiaojun Shen、Minghua Dong、Xiaomeng Cheng、Shulin Liu、Junjuan Yang、Zhenpeng Wang、Huizhen Liu、Buxing Han

  DOI：10.1039/d1sc05231d

  日期：——

  activation and cleavage of C–C bonds remains a critical scientific issue in many organic reactions and is an unmet challenge due to their intrinsic inertness and ubiquity. Meanwhile, it is crucial for the valorization of lignin into high-value chemicals. Here, we proposed a novel strategy to enhance the Caromatic–Cα bond cleavage by pre-functionalization with amine sources, in which an active amine intermediate

  C-C 键的活化和裂解仍然是许多有机反应中的一个关键科学问题，并且由于其固有的惰性和普遍存在性，是一个尚未解决的挑战。同时，这对于将木质素转化为高价值化学品至关重要。在这里，我们提出了一种通过胺源预官能化来增强 C芳香族-C α键裂解的新策略，其中首先通过马尔可夫尼科夫氢胺化形成活性胺中间体，以降低 C芳香族-C α键的解离能然后裂解形成目标化学物质。更重要的是，该策略提供了一种实现木质素或其平台分子中芳核和侧链最大利用的方法。在工业二甲胺（DMA）存在下，以草本木质素或对香豆酸单体为原料，以高产率生产酚类和N , N-二甲基乙胺化合物。
• Redox-neutral photochemical Heck-type arylation of vinylphenols activated by visible light
  作者：Kangjiang Liang、Tao Li、Na Li、Yang Zhang、Lei Shen、Zhixian Ma、Chengfeng Xia

  DOI：10.1039/c9sc06184c

  日期：——

  Disclosed herein is a photochemical Heck-type arylation of vinylphenols with non-activated aryl and heteroaryl halides under visible light irradiation. Preliminary mechanistic studies suggested that the colored vinylphenolate anions acted as a strong reducing photoactivator to directly activate (hetero)aryl halides without the need for any sacrificial reductants. The photochemically generated aryl radicals

  本文公开了在可见光照射下乙烯基酚与未活化的芳基和杂芳基卤化物的光化学Heck型芳基化。初步的机理研究表明，有色乙烯基酚酸根阴离子可作为强还原性光活化剂，直接活化（杂）芳基卤化物，而无需任何牺牲性还原剂。光化学产生的芳基与另一个乙烯基苯酚分子偶联，以区域特异性和立体选择性的方式提供Heck型芳基化产物。发达的光化学芳基化方案显示出优异的官能团耐受性，并且无需任何保护-脱保护程序即可成功应用于具有挑战性的天然产物后期修饰。