反式-2,4-二氯苯乙烯酸 | 1201-99-6

• 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: 反式-2,4-二氯苯乙烯酸
• 中文别名: 2,4-二氯肉桂酸
• 英文名称: 2,4-dichlorocinnamic acid
• 英文别名: 2,4-Dichlorzimtsaeure；3-(2,4-dichlorophenyl)acrylic acid；3-(2,4-dichlorophenyl)prop-2-enoic acid
• CAS: 1201-99-6
• 化学式: C₉H₆Cl₂O₂
• mdl: MFCD00004373
• 分子量: 217.051
• InChiKey: MEBWABJHRAYGFW-UHFFFAOYSA-N

物化性质

• 熔点：
  233-235 °C(lit.)
• 沸点：
  359.4±27.0 °C(Predicted)
• 密度：
  1.3944 (estimate)
• 稳定性/保质期：

  避免与不相容材料接触，与强氧化剂反应。

计算性质

• 辛醇/水分配系数(LogP)：
  3
• 重原子数：
  13
• 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,S28,S37/39
• 危险类别码：
  R37/38
• WGK Germany：
  3
• 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：
  密封存储，应存放在阴凉干燥的仓库中。

SDS

Name:	Trans-2 4-Dichlorocinnamic Acid 98% Material Safety Data Sheet
Synonym:	3-(2,4-Dichlorophenyl)-2-Propenoic Acid
CAS:	1201-99-6

Section 1 - Chemical Product MSDS Name:Trans-2 4-Dichlorocinnamic Acid 98% Material Safety Data Sheet
Synonym:3-(2,4-Dichlorophenyl)-2-Propenoic Acid

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Section 2 - COMPOSITION, INFORMATION ON INGREDIENTS

CAS#	Chemical Name	content	EINECS#
1201-99-6	Trans-2,4-Dichlorocinnamic Acid	98	214-860-1

Hazard Symbols: XI
Risk Phrases: 37/38

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Section 3 - HAZARDS IDENTIFICATION
EMERGENCY OVERVIEW
Irritating to respiratory system and skin.The toxicological properties of this material have not been fully investigated.
Potential Health Effects
Eye:
Causes eye irritation. May cause chemical conjunctivitis.
Skin:
Causes skin irritation.
Ingestion:
May cause gastrointestinal irritation with nausea, vomiting and diarrhea. The toxicological properties of this substance have not been fully investigated.
Inhalation:
Causes respiratory tract irritation. The toxicological properties of this substance have not been fully investigated. Can produce delayed pulmonary edema.
Chronic:
Effects may be delayed.

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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.
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.
Extinguishing Media:
Use agent most appropriate to extinguish fire. 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:
Vacuum or sweep up material and place into a suitable disposal container. Clean up spills immediately, observing precautions in the Protective Equipment section. Avoid generating dusty conditions.
Provide ventilation.

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Section 7 - HANDLING and STORAGE
Handling:
Wash thoroughly after handling. Remove contaminated clothing and wash before reuse. Use with adequate ventilation. Minimize dust generation and accumulation. Avoid contact with eyes, skin, and clothing. Keep container tightly closed. Avoid ingestion and inhalation.
Storage:
Store in a cool, dry place. 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# 1201-99-6: 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:
A respiratory protection program that meets OSHA's 29 CFR 1910.134 and ANSI Z88.2 requirements or European Standard EN 149 must be followed whenever workplace conditions warrant respirator use.

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Section 9 - PHYSICAL AND CHEMICAL PROPERTIES

Physical State: Powder
Color: white
Odor: none reported
pH: Not available.
Vapor Pressure: Not available.
Viscosity: Not available.
Boiling Point: Not available.
Freezing/Melting Point: 233.00 - 235.00 deg C
Autoignition Temperature: Not applicable.
Flash Point: Not applicable.
Explosion Limits, lower: Not available.
Explosion Limits, upper: Not available.
Decomposition Temperature:
Solubility in water:
Specific Gravity/Density:
Molecular Formula: C9H6Cl2O2
Molecular Weight: 217.05

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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:
Incompatible materials, dust generation, excess heat, strong oxidants.
Incompatibilities with Other Materials:
Oxidizing agents.
Hazardous Decomposition Products:
Hydrogen chloride, 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# 1201-99-6: GD8575000 LD50/LC50:
Not available.
Carcinogenicity:
Trans-2,4-Dichlorocinnamic 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
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 37/38 Irritating to respiratory system and skin.
Safety Phrases:
S 28 After contact with skin, wash immediately
with...
S 28A After contact with skin, wash immediately with
plenty of water.
S 37 Wear suitable gloves.
S 45 In case of accident or if you feel unwell, seek
medical advice immediately (show the label where
possible).
WGK (Water Danger/Protection)
CAS# 1201-99-6: No information available.
Canada
None of the chemicals in this product are listed on the DSL/NDSL list.
CAS# 1201-99-6 is not listed on Canada's Ingredient Disclosure List.
US FEDERAL
TSCA
CAS# 1201-99-6 is not listed on the TSCA inventory.
It is for research and development use only.

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SECTION 16 - ADDITIONAL INFORMATION
N/A

制备方法与用途

制备方法

肉桂酸是一种有机合成中间体，我国GB-2760-96将其列为允许使用的食用香料。它主要用于配制香辛料、樱桃、杏、蜜蜂等类型的香料，也可用于新鲜水果和蔬菜的防腐。

作为有机合成的重要原料，肉桂酸广泛应用于医药行业，是生产阿斯巴甜的主要原料L-苯丙氨酸的关键成分之一，还用于制备治疗膀胱过度兴奋引起的尿频症状的药物——毒蕈碱受体拮抗剂托特罗定。此外，它在抗肿瘤药多西他赛（多紫杉醇）的制备过程中也有应用。

肉桂酸还可用于制造局部麻醉剂、杀菌剂和止血药等产品。在农药领域，它可以作为生长促进剂和长效杀菌剂应用于果品和蔬菜的防腐处理。

反应信息

• 作为反应物：
  描述：

  反式-2,4-二氯苯乙烯酸 在 platinum(IV) oxide N-溴代丁二酰亚胺(NBS) 、 氢气 、 sodium methylate 、 二异丁基氢化铝 、 三苯基膦 作用下， 以 甲醇 、 乙醚 、 二氯甲烷 、 N,N-二甲基甲酰胺 为溶剂， 25.0 ℃ 、344.73 kPa 条件下， 反应 21.09h， 生成 Methyl 4-[3-(2,4-dichlorophenyl)propylsulfanyl]-3-oxobutanoate
  参考文献：
  名称：

  ATP-Citrate Lyase as a Target for Hypolipidemic Intervention. Design and Synthesis of 2-Substituted Butanedioic Acids as Novel, Potent Inhibitors of the Enzyme

  摘要：

  ATP-citrate lyase is the primary enzyme responsible for the synthesis of cytosolic acetyl-CoA in many tissues. Inhibitors of the enzyme represent a potentially novel class of hypolipidemic agent, which are anticipated to have combined hypocholesterolemic and hypotriglyceridemic properties. A series of a-substituted butanedioic acids have been designed and synthesized as inhibitors of the enzyme, The best compounds, 58, 68, 71, 74 have reversible K-i's in the 1-3 mu M range against the isolated rat enzyme, As representative of this compound class, 58, has been shown to exert its inhibitory action through a mainly competitive mechanism with respect to citrate and a noncompetitive one with respect to CoA. None of the inhibitors were able to inhibit cholesterol and/or fatty acid synthesis in HepG2 cells. This has been attributed to the adverse physicochemical properties of the molecules leading to a lack of cell penetration. Despite this, a lead structural class of compound has been identified with the potential for modification into potent, cell-penetrant, and efficacious inhibitors of ATP-citrate lyase.

  DOI：

  10.1021/jm960167w
• 作为产物：
  描述：

  丙二酸 、 2,4-二氯苯甲醛 在 吡啶 作用下， 生成 反式-2,4-二氯苯乙烯酸
  参考文献：
  名称：

  新型1-乙基-6-氟-1,4-二氢-4-氧代-7（1-哌嗪基）喹啉-3-羧酸衍生物的设计，合成及体外抗菌/抗真菌评价

  摘要：

  根据结合生物活性亚结构的原理，制备了一系列的1-乙基-6-氟-1,4-二氢-4-氧代-7（1-哌嗪基）喹啉-3-羧酸（诺氟沙星）衍生物，并对其进行了测试。它们在体外对5种植物病原菌和3种真菌的活性。初步的生物测定表明，几乎所有合成的目标化合物都保留了诺氟沙星的抗菌活性，并具有一些作为羧酸酰胺化合物的抗真菌活性。化合物的活性1和22对黄单胞菌比诺氟沙星更好，相比于农用链霉素硫酸盐（商业杀菌剂）对所有测试的化合物具有较好的抗菌活性稻X.，Xanthomonas axonopodis和Erwinia aroideae。此外，化合物2和20对200毫克/升的浓度对茄红枯萎病菌表现出良好的抗真菌活性，并且它们对生长的抑制分别达到83％和94％。

  DOI：

  10.1016/j.ejmech.2009.05.028

文献信息

• Synthesis and Anti-influenza Activities of Novel Baicalein Analogs
  作者：Shu-Ting Chung、Pei-Yu Chien、Wen-Hsin Huang、Chen-Wen Yao、An-Rong Lee

  DOI：10.1248/cpb.c13-00897

  日期：——

  A series of novel flavones derivatives were synthesized based on modification of the active ingredients of a traditional Chinese medicine Scutellaria baicalensis GEORGI and screened for anti-influenza activity. The synthetic baicalein (flavone) analogs, especially with the B-rings substituted with bromine atoms, were much more potent than oseltamivir or ribavirin against H1N1 Tamiflu-resistant (H1N1 TR) virus and usually with more favorable selectivity. The most promising were 5b, 5c, 6b and 6c, all displaying an 50% effective concentration (EC50) at around 4.0–4.5 µM, and a selective index (SI=50% cytotoxic concentration (CC50)/EC50)>70. For seasonal H3N2-infected influenza virus, both 5a and 5b with SI >17.3 indicated superior to ribavirin. The flavonoids having both not-naturally-occurring bromo-substituted B-rings and appropriate hydroxyls positioning on the A-rings might be critical in determining the activity and selectivity against H1N1-Tamiflu-resistant infected influenza viruses.

  一系列新型黄酮衍生物是基于对传统中药黄芩（Scutellaria baicalensis GEORGI）活性成分的修饰合成的，并进行了抗流感活性筛选。合成的大黄素（黄酮）类似物，特别是B环上带有溴原子取代的类似物，对H1N1达菲耐药（H1N1 TR）病毒的活性远超奥司他韦或利巴韦林，并且通常具有更优越的选择性。最有希望的化合物是5b、5c、6b和6c，它们的50%有效浓度（EC50）都在4.0–4.5 µM左右，选择指数（SI=50%细胞毒性浓度（CC50）/EC50）>70。对于季节性H3N2流感病毒感染，5a和5b的SI均大于17.3，优于利巴韦林。这些具有非天然溴取代B环和A环上适当羟基位置的黄酮类化合物可能在决定抗H1N1达菲耐药流感病毒的活性和选择性方面起关键作用。
• Synthesis and characterization of two novel biological-based nano organo solid acids with urea moiety and their catalytic applications in the synthesis of 4,4′-(arylmethylene)bis(1H-pyrazol-5-ol), coumarin-3-carboxylic acid and cinnamic acid derivatives under mild and green conditions
  作者：Mohammad Ali Zolfigol、Roya Ayazi-Nasrabadi、Saeed Baghery

  DOI：10.1039/c5ra14001c

  日期：——

  Green and straight-forward syntheses of 4,4′-(arylmethylene)bis(1H-pyrazol-5-ol) derivatives using nano structure organocatalysts, namely 2-carbamoylhydrazine-1-sulfonic acid and carbamoylsulfamic acid, have been developed.

  利用纳米结构有机催化剂，即2-氨基甲酰肼-1-磺酸和氨基甲酰磺酸，直接绿色合成4,4′-(芳基亚甲基)双(1H-吡唑-5-醇)衍生物的方法已经被开发出来。

• Environmentally benign and energy efficient methodology for condensation: an interesting facet to the classical Perkin reaction
  作者：Poonam Mahadev Pawar、Krishna Jagannath Jarag、Ganapati Subray Shankarling

  DOI：10.1039/c0gc00712a

  日期：——

  We have reported use of biodegradable deep eutectic solvent (DES) based on choline chloride and urea, for the synthesis of cinnamic acid and its derivatives viaPerkin reaction. The reaction proceeds efficiently under mild condition without use of additional catalyst with better yields. Ease of recovery and reusability of solvent with consistent activity makes this method efficient and environmentally benign. This method is also energy efficient and easy to handle.

  我们报道了使用基于氯化胆碱和尿素的可生物降解深共晶溶剂（DES），通过Perkin反应合成肉桂酸及其衍生物的方法。该反应在温和条件下高效进行，无需额外催化剂，产率更佳。溶剂的易于回收和可重复使用，且活性一致，使得这种方法高效且环境友好。此方法还具有能效高、操作简便的优点。
• [DE] 3-(4-PIPERIDIN-1YLMETHYL-PHENYL) -PROPIONSÄURE-PHRNYLAMID-DERIVATE UND VERWANDTE VERBINDUNGEN ALS MCH (MELANINE CONCENTRATING HORMONE) ANTAGONISTEN ZUR BEHANDLUNG VON ESSSTÖRUNGEN<br/>[EN] 3-(4-PIPERIDINE-1YLMETHYL-PHENYL)-PROPION ACID-PHENYLAMIDE-DERIVATIVES AND RELATED COMPOUNDS USED IN THE FORM OF MCH ANTAGONISTS (MELANINE CONCENTRATING HORMONE) FOR TREATING EATING DISORDERS<br/>[FR] DERIVES D'ACIDE 3-(4-PIPERIDINE-1YLMETHYL-PHENYL) PROPIONIQUE-PHENYLAMIDE ET COMPOSES APPARENTES, UTILISES COMME ANTAGONISTES MCH (HORMONE DE CONCENTRATION EN MELANINE) POUR LE TRAITEMENT DE TROUBLES DUS A L'ALIMENTATION
  申请人：BOEHRINGER INGELHEIM INT

  公开号：WO2005063239A1

  公开（公告）日：2005-07-14

  Die vorliegende Erfindung betrifft Amid-Verbindungen der allgemeinen Formel (I), in der die Gruppen und Reste A, B, b, W, X, Y, Z, R1, R2 und R3 die in Anspruch 1 angegebenen Bedeutungen aufweisen. Ferner betrifft die Erfindung Arzneimittel enthaltend mindestens ein erfindungsgemäßes Amid. Auf Grund der MCH-Rezeptor antagonistischen Aktivität eignen sich die erfindungsgemäßen Arzneimittel zur Behandlung von metabolischen Störungen und/oder Essstörungen, insbesondere von Adipositas, Bulimie, Anorexie, Hyperphagia und Diabetes.

  该发明涉及通式（I）的酰胺化合物，其中基团和残基A、B、b、W、X、Y、Z、R1、R2和R3具有权利要求1中所述的含义。此外，该发明涉及含有至少一种根据本发明的酰胺的药物。由于MCH受体拮抗活性，根据本发明的药物适用于治疗代谢紊乱和/或进食障碍，特别是肥胖症、暴食症、厌食症、过度进食和糖尿病。
• Controlling Plasma Stability of Hydroxamic Acids: A MedChem Toolbox
  作者：Paul Hermant、Damien Bosc、Catherine Piveteau、Ronan Gealageas、BaoVy Lam、Cyril Ronco、Matthieu Roignant、Hasina Tolojanahary、Ludovic Jean、Pierre-Yves Renard、Mohamed Lemdani、Marilyne Bourotte、Adrien Herledan、Corentin Bedart、Alexandre Biela、Florence Leroux、Benoit Deprez、Rebecca Deprez-Poulain

  DOI：10.1021/acs.jmedchem.7b01444

  日期：2017.11.9

  Hydroxamic acids are outstanding zinc chelating groups that can be used to design potent and selective metalloenzyme inhibitors in various therapeutic areas. Some hydroxamic acids display a high plasma clearance resulting in poor in vivo activity, though they may be very potent compounds in vitro. We designed a 57-member library of hydroxamic acids to explore the structure–plasma stability relationships

  异羟肟酸是杰出的锌螯合基团，可用于设计各种治疗领域中的有效和选择性金属酶抑制剂。一些异羟肟酸显示出较高的血浆清除率，导致体内活性差，尽管它们在体外可能是非常有效的化合物。我们设计了一个由57名成员组成的异羟肟酸文库，以探索这些系列中结构与血浆的稳定性关系，并确定哪些酶和哪些药效团对血浆稳定性至关重要。芳基酯酶和羧酸酯酶被确定为异羟肟酸的主要代谢酶。最后，我们建议引入或删除结构特征以提高稳定性。因此，这项工作提供了第一个药物化学工具箱（实验程序和结构指导），用于评估和控制异羟肟酸的血浆稳定性，并充分发挥其作为体内药理探针和治疗剂的潜力。这项研究与临床前开发特别相关，因为它允许获得在人和啮齿动物模型中同样稳定的化合物。