p-Coumaric acid 对香豆酸

CAS 501-98-4 MFCD00004399

化学结构图

501-98-4
SMILES: O=C(O)/C=C/c1ccc(O)cc1

化学属性

Mol. FormulaC9H8O3
Mol. Weight164.16
Melting Point214 °C
TSCANo
Density1.329
Solubility可溶
Stability对湿度敏感
Appearance 本品为微黄色粉状结晶，m.p.216℃，易溶于醇、醚及热水。
Flash Point167.2°C
Boiling Point231.61 °C at 760 mmHg

别名和识别编码

Chemical Name4-Hydroxycinnamic acid
CAS Number501-98-4
Alfabeta NameHYDROXYPHENYLACRYLICACID 34()--
MDL NumberMFCD00004399
Synonym p-Coumaric acid {LY} p-Coumaric acid p-coumaric acid p-coumaryl alcohol p-hydroxycinnamic acid para-coumaric acid phenol, 4-(3-hydroxy-1-propenyl)- trans-3-(4'-hydroxyphenyl)-2-propenoic acid trans-HPPA {} {LY} p-Coumaric acid {} {} {LY} p-Coumaric acid {} {} {} {LY} p-Coumaric acid {} {} {} {} {LY} p-Coumaric acid {} {} {} {} {} {LY} p-Coumaric acid {} {} {} {} {} {} {LY} p-Coumaric acid {} {} {} {} {} {} {} {LY} p-Coumaric acid {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {LY} p-Coumaric acid {} {} {} {} {} {} {} {} {} {LY} p-Coumaric acid {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {LY} p-Coumaric acid {} {} {} {} {} {} {} {} {} {} {} { {} {} {} {} {} {} {} {} {} {} {} {LY} p-Coumaric acid {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {LY} p-Coumaric acid {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {LY}
Beilstein Registry Number2207383
Reaxys-RN2207383
PubChem Substance ID637542
Merck Number2560
EC Number231-000-0
Chemical Name Translation对香豆酸
LabNetwork Molecule IDLN00173841
InChIInChI=1S/C9H8O3/c10-8-4-1-7(2-5-8)3-6-9(11)12/h1-6,10H,(H,11,12)/b6-3+
Canonical SMILESO=C(O)/C=C/C1=CC=C(O)C=C1
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分类

  • {SNA} A - D, Additional Standards, Aesculus, Alphabetical Index of Phytochemical Standards, Analytical Standards, Calendula, Camellia, Chromatography, Cichorium, Cinnamomum, Citrus, Curcuma, Curcuma longa (Turmeric),

产品应用

  • 香料合成。祛痰药杜鹃素的中间体。

相关文献及参考

  • Beilstein:10,297
  • Short: EINECS
  • Short: III/5a
  • Short: LC
  • Short: VIII/5A
  • [1]. Jaganathan SK, et al. Events associated with apoptotic effect of p-Coumaric acid in HCT-15 colon cancer cells. World J Gastroenterol. 2013 Nov 21;19(43):7726-34.

安全信息

Warnings IRRITANT
Precautionary statements
  • P260 Do not breathe dust/fume/gas/mist/vapours/spray. 不要吸入粉尘/烟/气体/烟雾/蒸汽/喷雾。
  • P261 Avoid breathing dust/fume/gas/mist/vapours/spray. 避免吸入粉尘/烟/气体/烟雾/蒸汽/喷雾。
  • P262 Do not get in eyes, on skin, or on clothing. 不要接触眼睛，皮肤或衣服。
  • P264 Wash hands thoroughly after handling. 处理后要彻底洗净双手。
  • P264+P265
  • P270 Do not eat, drink or smoke when using this product. 使用本产品时不要吃东西，喝水或吸烟。
  • P271 Use only outdoors or in a well-ventilated area.? 只能在室外或通风良好的地方使用。
  • P272 Contaminated work clothing should not be allowed out of the workplace. 污染的工作服不得带出工作场所。
  • P280 Wear protective gloves/protective clothing/eye protection/face protection. 戴防护手套/防护服/眼睛的保护物/面部保护物。
  • P301+P316
  • P301+P317
  • P301+P330+P331
  • P302+P352
  • P302+P361+P354
  • P304+P340
  • P305+P351+P338
  • P305+P351+P338+P337+P313
  • P305+P354+P338
  • P312 Call a POISON CENTER or doctor/physician if you feel unwell. 如果你感觉不适，呼叫解毒中心或医生/医师。
  • P316
  • P317
  • P319
  • P321 Specific treatment (see … on this label). 具体治疗（见本标签上的）。
  • P330 Rinse mouth. 漱口
  • P332+P313
  • P332+P317
  • P333+P313
  • P333+P317
  • P337+P317
  • P361+P364
  • P362 Take off contaminated clothing and wash before reuse. 脱掉污染的衣服，清洗后方可重新使用
  • P362+P364
  • P363 Wash contaminated clothing before reuse. 被污染的衣服洗净后方可重新使用。
  • P403+P233
  • P405 Store locked up. 上锁保管。
  • P501 Dispose of contents/container to..… 处理内容物/容器.....
GHS Symbol
RTECSGD9095000
Signal word Warning
Hazard statements
  • H301 Toxic if swallowed 吞食有毒
  • H302 Harmful if swallowed 吞食有害
  • H303 May be harmfully swallowed 吞食可能有害
  • H311 Toxic in contact with skin 皮肤接触中毒
  • H314 Causes severe skin burns and eye damage 导致严重的皮肤灼伤和眼睛损伤
  • H315 Causes skin irritation 会刺激皮肤
  • H317 May cause an allergic skin reaction 可能导致皮肤过敏
  • H318 Causes serious eye damage 严重伤害眼睛
  • H319 Causes serious eye irritation 严重刺激眼睛
  • H335 May cause respiratory irritation 可能导致呼吸道刺激
WGK Germany2
Safety Statements
  • S26 In case of contact with eyes, rinse immediately with plenty of water and seek medical advice 眼睛接触后，立即用大量水冲洗并征求医生意见；
  • S36 Wear suitable protective clothing 穿戴适当的防护服；
  • S36/37/39 Wear suitable protective clothing, gloves and eye/face protection 穿戴适当的防护服、手套和眼睛/面保护；
Risk Statements
  • R36/37/38 Irritating to eyes, respiratory system and skin 对眼睛、呼吸系统和皮肤有刺激性
  • R62 Possible risk of impaired fertility 有削弱生殖能力的危险
Personal Protective Equipment dust mask type N95 (US), Eyeshields, Gloves
Hazard Codes Xi
Storage condition RT, stored under nitrogen {LY} RT, stored under nitrogen {} {LY} RT, stored under nitrogen {} {} {LY} RT, stored under nitrogen {} {} {} {LY} RT, stored under nitrogen {} {} {} {} {LY} RT, stored under nitrogen {} {} {} {} {} {LY} RT, stored under nitrogen {} {} {} {} {} {} {LY} RT, stored under nitrogen {} {} {} {} {} {} {} {LY} RT, stored under nitrogen {} {} {} {} {} {} {} {} {LY} RT, stored under nitrogen {} {} {} {} {} {} {} {} {} {LY} RT, stored under nitrogen {} {} {} {} {} {} {} {} {} {} {LY} RT, stored under nitrogen {} {} {} {} {} {} {} {} {} {} {} {LY} RT, stored under nitrogen {} {} {} {} {} {} {} {} {} {} {} {} {LY} RT, stored under nitrogen {} {} {} {} {} {} {} {} {} {} {} {} {} {LY} RT, stored under nitrogen {} {} {} {} {} {} {} {} {} {} {} {} {} {} {LY} RT, stored under nitrogen {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {LY} RT, stored under nitrogen {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} 
TYPE OF TEST            : LD50 - Lethal dose, 50 percent kill
ROUTE OF EXPOSURE       : Oral
SPECIES OBSERVED        : Rodent - mouse
DOSE/DURATION           : 2850 mg/kg
TOXIC EFFECTS :
   Behavioral - somnolence (general depressed activity)
   Lungs, Thorax, or Respiration - respiratory depression
REFERENCE :
   GNRIDX Gendai no Rinsho.  (Tokyo, Japan)  V.1-10, 1967-76(?).
   Volume(issue)/page/year: 3,675,1969

TYPE OF TEST            : LD50 - Lethal dose, 50 percent kill
ROUTE OF EXPOSURE       : Intraperitoneal
SPECIES OBSERVED        : Rodent - mouse
DOSE/DURATION           : 1160 mg/kg
TOXIC EFFECTS :
   Behavioral - somnolence (general depressed activity)
   Lungs, Thorax, or Respiration - respiratory depression
REFERENCE :
   GNRIDX Gendai no Rinsho.  (Tokyo, Japan)  V.1-10, 1967-76(?).
   Volume(issue)/page/year: 3,675,1969

其他信息

  • 溶于热水、热乙醇和乙醚，微溶于冷水，几乎不溶于苯和石油醚。有刺激性。
  • MSDS 信息:4-Hydroxycinnamic acid(501-98-4).msds
  • 图谱信息:4-羟基肉桂酸(501-98-4)红外图谱(IR1) 4-羟基肉桂酸(501-98-4)红外图谱(IR2)
  • MOL 文件:501-98-4.mol
  • 4-羟基肉桂酸价格(试剂级):更新日期 产品编号 产品名称 包装 价格 2014/06/02 C0393 反-对香豆酸 trans-p-Coumaric Acid 500G 5960元 2014/06/02 C0393 反-对香豆酸 trans-p-Coumaric Acid 25G 596元 2010/06/21 121090250 4-羟基肉桂酸 p-Hydroxycinnamic acid 98%, predominantly trans 25 GR 886元
  • Alfa Aesar:反-对羟基苯基丙烯酸,98% trans-4-Hydroxycinnamic acid, 98%(501-98-4)
  • 用途三:香料合成。祛痰药杜鹃素的中间体。
  • 方法一:其制备方法是以乙酰水杨酰氯为原料，在氯化镁存在下，在乙腈溶剂中与丙二酸二乙酯反应，再加入三乙胺，在0℃反应1h，得到(2-乙酰氧基苯甲酰基)丙二酸二乙酯生成物，然后在氢氧化钾/甲醇溶液中加热至50℃，反应3h，环合而得到产品。 也可以用乙酰乙酸乙酯为原料，在氢氧化钠存在下，在异丁基甲基酮溶剂中与乙酰水杨酰氯于15～20℃反应3.5 h，得到2-(2-羟基苯甲酰基)乙酰乙酸钠盐，该反应产物与盐酸在25～30℃反应30min，得到3-乙酰基-4-羟基香豆素，再在浓硫酸下，在90～95℃加热4h而得到产品。 还可以用2-羟基苯乙酮为原料，在碳酸钾存在下，在高压釜中通入5.88MPa二氧化碳，在室温下通15h，然后在60℃保持15h，先生成2-羟基苯-3-氧丙酸，再环合成产品。
  • Sigma Aldrich:501-98-4(sigmaaldrich)
  • TCI Shanghai:(E)-3-(4-羟苯基)-2-丙烯酸 trans-p-Coumaric Acid,>;98.0%(GC)(T)(501-98-4)
  • 上游原料:乙酸乙酯 --> 氢氧化钾 --> 苯酚 --> 浓硫酸 --> 4-羟基香豆素 --> 2-己酮 --> 邻乙酰水杨酰氯
  • 用途二:4-羟基香豆素是抗凝血剂杀鼠剂杀鼠灵、杀鼠醚、溴敌隆、溴鼠灵、鼠得克、氟鼠灵、噻鼠灵、克鼠灵等的中间体，也可以在医药上制抗血凝药双香豆素乙酯、酮苄香豆素等。
  • 用途一:用作医药与香料工业中间体
  • Acros Organics:对羟基肉桂酸/对香豆酸 p-Hydroxycinnamic acid, predominantly trans, 98%(501-98-4)

系列性分类

  1. Life Science 生命科学
  2. Cancer Research
  3. Chemopreventive Agents - Cancer Research
  4. Antioxidant and Free Radical Scavengers - Chemopreventive Agents
  1. Chemical Synthesis 化学合成
  2. Synthetic Reagents 合成试剂
  3. Organic Acids - Synthetic Reagents
  1. Life Science 生命科学
  2. Nutrition Research 营养研究
  3. Phytochemicals by Plant (Food/Spice/Herb) - Nutrition Research
  4. Allium sativum (Garlic) - Phytochemicals by Plant (Food/Spice/Herb)
  1. Chemical Synthesis 化学合成
  2. Building Blocks 合成砌块
  3. Organic Building Blocks 有机砌块
  4. Carbonyl Compounds 羰基化合物
  5. Carboxylic Acids - Carbonyl Compounds
  1. Chemical Synthesis 化学合成
  2. Building Blocks 合成砌块
  3. Organic Building Blocks 有机砌块
  4. Carbonyl Compounds 羰基化合物
  5. Carboxylic Acids - Carbonyl Compounds
  6. C9 - Carboxylic Acids
  1. Analytical & Chromatography 分析化学与色谱
  2. Analytical Standards
  3. Chromatography - Analytical Standards
  4. Life Sciences Standards - Chromatography
  5. Phytopharma Standards - Life Sciences Standards
  6. Standards by Plant Genus - Phytopharma Standards
  7. Trifolium - Standards by Plant Genus
  1. Life Science 生命科学
  2. Biochemistry / Glyco-Chemistry
  3. Plant Growth Regulators
  1. Life Science 生命科学
  2. Biochemicals and Reagents
  3. Metabolomics
  4. Metabolic Pathways
  5. Metabolites and Cofactors on the Metabolic Pathways Chart
  1. Life Science 生命科学
  2. Biochemicals and Reagents
  3. Enzymes, Inhibitors, and Substrates
  4. Metabolomics
  5. Metabolic Pathways
  6. Metabolites and Cofactors on the Metabolic Pathways Chart
  1. Medical Research Areas
  2. Metabolism
  3. Endogenous Metabolite  (内源性代谢物)

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