4-Hydroxycinnamic acid

Base Information

• Chemical Name: 4-Hydroxycinnamic acid
• CAS No.: 501-98-4
• Molecular Formula: C₉H₈O₃
• Molecular Weight: 164.161
• Hs Code.: 29163990
• European Community (EC) Number: 231-000-0
• NSC Number: 674321,59260
• UNII: IBS9D1EU3J
• DSSTox Substance ID: DTXSID30901076
• Nikkaji Number: J6.196D,J8.929J
• Wikipedia: P-Coumaric_acid
• Wikidata: Q99374
• Pharos Ligand ID: ALB466C93KG5
• Metabolomics Workbench ID: 37986
• ChEMBL ID: CHEMBL66879
• Mol file: 501-98-4.mol

Synonyms:4-coumaric acid;4-coumaric acid, (E)-isomer;4-coumaric acid, (Z)-isomer;4-coumaric acid, disodium salt;4-hydroxycinnamic 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

Chemical Property of 4-Hydroxycinnamic acid

Chemical Property:

• Appearance/Colour: Off-white to beige or greenish powder
• Vapor Pressure: 7.19E-05mmHg at 25°C
• Melting Point: 214 °C (dec.)(lit.)
• Refractive Index: 1.6
• Boiling Point: 346.052 °C at 760 mmHg
• PKA: 4.65±0.10(Predicted)
• Flash Point: 177.284 °C
• PSA: 57.53000
• Density: 1.33 g/cm³
• LogP: 1.49000
• Storage Temp.: Keep in dark place,Sealed in dry,Room Temperature
• Solubility.: ethanol: soluble50mg/mL
• Water Solubility.: soluble
• 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

p-Coumaric acid ^*data from reagent suppliers

Safty Information:

• Pictogram(s): Xi
• Hazard Codes: Xi
• Statements: 36/37/38
• Safety Statements: 26-36-37/39

MSDS Files:

SDS file from LookChem

Total 1 MSDS from other Authors

Useful:

• Canonical SMILES: C1=CC(=CC=C1C=CC(=O)O)O
• Isomeric SMILES: C1=CC(=CC=C1/C=C/C(=O)O)O
• Uses: trans-p-Coumaric Acid is the E-isomer of p-Coumaric Acid (C755365), a hydroxy derivative of Cinnamic Acid with antioxidant properties. p-Coumaric acid is a is a major component of lignocellulose. Stud ies suggest that p-Coumaric Acid may reduce the risk of cancer by reducing the formation of carcinogenic nitrosamines.

Technology Process of 4-Hydroxycinnamic acid

There total 34 articles about 4-Hydroxycinnamic 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:

cis-p-coumaroylsuccinimide

4-propoxy-cis-cinnamic acid

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

Refernces

• 1、 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.
• 2、 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.