cis-p-Coumaric acid

Base Information

• Chemical Name: cis-p-Coumaric acid
• CAS No.: 4501-31-9
• Molecular Formula: C₉H₈O₃
• Molecular Weight: 164.161
• European Community (EC) Number: 224-813-7
• NSC Number: 90284
• DSSTox Substance ID: DTXSID901315564
• Nikkaji Number: J205.880D
• Wikidata: Q27102404
• Metabolomics Workbench ID: 44504
• ChEMBL ID: CHEMBL2336752
• Mol file: 4501-31-9.mol

Synonyms:cis-p-Coumaric acid;cis-4-Hydroxycinnamic acid;4501-31-9;(Z)-p-Coumaric acid;cis-p-Cumaric acid;cis-p-Hydroxycinnamic acid;cis-4-coumaric acid;cis-p-Coumarinic acid;(Z)-3-(4-Hydroxyphenyl)-2-propenoic acid;cis-p-Coumarate;(Z)-3-(4-hydroxyphenyl)prop-2-enoic acid;(2Z)-3-(4-hydroxyphenyl)prop-2-enoic acid;EINECS 224-813-7;CINNAMIC ACID, p-HYDROXY-, (Z)-;CHEBI:17450;2-Propenoic acid, 3-(4-hydroxyphenyl)-, (Z)-;(2Z)-3-(4-hydroxyphenyl)acrylic acid;(Z)-p-hydroxycinnamic acid;SCHEMBL434720;4-coumaric acid, (Z)-isomer;CHEMBL2336752;Cinnamic acid, 4-hydroxy-, cis-;DTXSID901315564;NSC90284;NSC 90284;NSC-90284;(Z)-3-(4-hydroxyphenyl)acrylic acid;AKOS040763716;LS-54113;C06738;J-502594;Q27102404;15F90638-DCF1-4922-AFB2-BAF5EA308C8C

Chemical Property of cis-p-Coumaric acid

Chemical Property:

• Vapor Pressure: 2.24E-05mmHg at 25°C
• Melting Point: 130-131 °C
• Refractive Index: 1.66
• Boiling Point: 346.052 °C at 760 mmHg
• PKA: 4.59±0.10(Predicted)
• Flash Point: 177.284 °C
• PSA: 57.53000
• Density: 1.33 g/cm³
• LogP: 1.49000
• Storage Temp.: Amber Vial, -20°C Freezer
• Solubility.: Acetone (Slightly), Methanol (Slightly)
• XLogP3: 1.5
• Hydrogen Bond Donor Count: 2
• Hydrogen Bond Acceptor Count: 3
• Rotatable Bond Count: 2
• Exact Mass: 164.047344113
• Heavy Atom Count: 12
• Complexity: 178

Purity/Quality:

99%, ^*data from raw suppliers

cis-4-HydroxycinnamicAcid ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: C1=CC(=CC=C1C=CC(=O)O)O
• Isomeric SMILES: C1=CC(=CC=C1/C=C\C(=O)O)O
• Uses: An antioxidative active compound isolated from the EtOAc layer of MeOH extracts of kochujang, Korean fermented red pepper paste. Photoisomerization of ionic liquid ammonium cinnamates. Cinnamic acids upon irradiation in solution undergo geometric isomerization while dimerizing to different dimers in the crystalline state. An antioxidative active compound isolated from the EtOAc layer of MeOH extracts of kochujang, Korean fermented red pepper paste. Photoisomerization of ionic liquid ammonium cinnamates. Cinnamic acids upon irradiation in solution undergo geometric isomerization while dimerizing to different dimers in the crystalline state.

Technology Process of cis-p-Coumaric acid

There total 34 articles about cis-p-Coumaric acid which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield: 32.0%

p-Coumaric Acid (7400-08-0,50940-26-6) → (Z)-p-coumaric acid (501-98-4,4501-31-9,7400-08-0,50940-26-6)

Guidance literature:

In methanol; at 4 ℃; for 5h; Irradiation;

DOI:10.1271/bbb.62.2133

Reference yield: 17.0%

(Z)-3-[4-(tert-Butyl-dimethyl-silanyloxy)-phenyl]-acrylic acid methyl ester → (Z)-p-coumaric acid (501-98-4,4501-31-9,7400-08-0,50940-26-6)

Guidance literature:

With lithium hydroxide; In methanol; for 3h; Heating;

DOI:10.1021/ja00069a006

Reference yield:

peonidin 3-O-[2-O-(2-O-(trans-feruloyl)-glucosyl)-6-O-(cis-p-coumaroyl)-glucoside]-5-O-[6-O-(malonyl)-glucoside] → D-Glucose (2280-44-6) + (E)-3-(4-hydroxy-3-methoxyphenyl)acrylic acid (1135-24-6,537-98-4) + malonic acid (141-82-2) + (Z)-p-coumaric acid (501-98-4,4501-31-9,7400-08-0,50940-26-6) + peonidin chloride (134-01-0)

Guidance literature:

With hydrogenchloride; water; at 100 ℃; for 1h;

DOI:10.1016/j.phytochem.2011.12.019

upstream raw materials:

p-Coumaric Acid

N-phthaloyl-L-tyrosine

methyl p-hydroxycinnamate

kankanoside H₂

Downstream raw materials:

4-Ethylphenol

p-Coumaric Acid

4-propoxy-cis-cinnamic acid

(Z)-3-(4-methoxyphenyl)acrylic acid

Refernces

• 1、 Garcia Cortez,Young,Marston,Wolfender,Hostettmann. "Xanthones, triterpenes and a biphenyl from Kielmeyera coriacea". . p. 1367 - 1374. Retrieved 1998.
• 2、 Brasseur, Thierry,Angenot, Luc. "FOUR ACYLATED FLAVONOL GLYCOSIDES FROM LEAVES OF STRYCHNOS VARIABILIS". . p. 3331 - 3334. Retrieved 1987.
• 3、 Kumar, Rakesh,Ketner, Aimee M.,Raghavan, Srinivasa R.. "Nonaqueous photorheological fluids based on light-responsive reverse wormlike micelles". . p. 5405 - 5411. Retrieved 2010.
• 4、 Al-Hamoud, Gadah Abdulaziz,Orfali, Raha Saud,Sugimoto, Sachiko,Yamano, Yoshi,Alothyqi, Nafee,Alzahrani, Ali Mohammed,Matsunami, Katsuyoshi. "Four New Flavonoids Isolated from the Aerial Parts of Cadaba rotundifolia Forssk. (Qadab)". . . Retrieved 2019/06/21.
• 5、 M?kil?, Leenamaija,Laaksonen, Oskar,Alanne, Aino-Liisa,Kortesniemi, Maaria,Kallio, Heikki,Yang, Baoru. "Stability of Hydroxycinnamic Acid Derivatives, Flavonol Glycosides, and Anthocyanins in Black Currant Juice". . p. 4584 - 4598. Retrieved 2016/07/06.