2-Propenoic acid, 3-(4-hydroxyphenyl)-, (2Z)-

Base Information

• Chemical Name: 2-Propenoic acid, 3-(4-hydroxyphenyl)-, (2Z)-
• CAS No.: 7400-08-0
• Molecular Formula: C9H8O3
• Molecular Weight: 164.161
• Hs Code.: DERIVATION
• DSSTox Substance ID: DTXSID6064660
• Wikidata: Q27104329
• Mol file: 7400-08-0.mol

Synonyms:2-Propenoic acid, 3-(4-hydroxyphenyl)-, (2Z)-;(E)-P-Coumaricacid;4-hydroxy cinnamic acid;CHEBI:36090;4hydroxycinnamic acid;p-hydroxy cinnamic acid;4- hydroxycinnamic acid;4-hy droxycinnamic acid;4-hydroxy-cinnamic acid;Enamine_005378;Epitope ID:116879;DTXSID6064660;3-(4-hydroxy-phenyl)-acrylic acid;AKOS017269003;SY015618;SY020906;FT-0618278;FT-0623944;FT-0649249;FT-0650655;Q27104329

Chemical Property of 2-Propenoic acid, 3-(4-hydroxyphenyl)-, (2Z)-

Chemical Property:

• Appearance/Colour: Light yellow to beige crystalline powder
• Vapor Pressure: 7.19E-05mmHg at 25°C
• Melting Point: 212-214 °C
• 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.: -20°C
• Solubility.: Acetone (Slightly), Chloroform (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:

98% ^*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: 26-36-36/37/39-22

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: C1=CC(=CC=C1C=CC(=O)O)O
• Uses: 4-Hydroxycinnamic acid is the hydroxy derivative of Cinnamic Acid with antioxidant properties. It is a is a major component of lignocellulose. Studies suggest that 4-Hydroxycinnamic acid may reduce the risk of cancer by reducing the formation of carcinogenic nitrosamines. A recent study reports that 4-Hydroxycinnamic acid may act as a chemical castrator in bees by altering the epression of genes required for ovary development. This compound is common in pollen a major constituent of the worker bee diet, but it is not found in queen bees'royal jelly.

Technology Process of 2-Propenoic acid, 3-(4-hydroxyphenyl)-, (2Z)-

There total 288 articles about 2-Propenoic acid, 3-(4-hydroxyphenyl)-, (2Z)- 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: 75.0%

N,N-dimethyl-L-tyrosine N-oxide (19704-86-0) → N,N-dimethylhydroxylamine (5725-96-2) + p-Coumaric Acid (7400-08-0,50940-26-6) + 4-Vinylphenol (2628-17-3,24979-70-2)

Guidance literature:

In N,N-dimethyl acetamide; at 130 ℃; Product distribution / selectivity;

Reference yield:

cyanidin 3-O-[2-O-(β-xylopyranosyl)-6-O-(4-O-(6-O-(trans-feruloyl)-β-glucopyranosyl)-trans-p-coumaroyl)-β-glucopyranoside]-5-O-[6-O-(malonyl)-β-glucopyranoside] → 3-(4-hydroxy-3-methoxyphenyl)acrylic acid (1135-24-6,537-98-4) + D-xylose (58-86-6) + cyanidin (13306-05-3) + D-glucose (50-99-7) + malonic acid (141-82-2) + para-coumaric acid (7400-08-0,50940-26-6)

Guidance literature:

With hydrogenchloride; water; at 100 ℃; for 2h;

DOI:10.1016/j.phytol.2013.10.004

Reference yield:

cyanidin 3-O-[2-O-(2-O-(trans-feruloyl)-β-xylopyranosyl)-6-O-(4-O-(β-glucopyranosyl)-trans-pcoumaroyl)-β-glucopyranoside]-5-O-[6-O-(malonyl)-β-glucopyranoside] → 3-(4-hydroxy-3-methoxyphenyl)acrylic acid (1135-24-6,537-98-4) + D-xylose (58-86-6) + cyanidin (13306-05-3) + D-glucose (50-99-7) + malonic acid (141-82-2) + para-coumaric acid (7400-08-0,50940-26-6)

Guidance literature:

With hydrogenchloride; water; at 100 ℃; for 2h;

DOI:10.1016/j.phytol.2013.10.004

upstream raw materials:

acetic anhydride

4-hydroxy-benzaldehyde

malonic acid

p-Iodophenol

Downstream raw materials:

4-pentyloxy-trans-cinnamic acid

4-(3-oxy-[1,2,3]oxadiazol-5-yl)-phenol

hydroxy-(4-hydroxy-phenyl)-acetaldehyde

3-amino-3-(4-hydroxyphenyl)propionic acid

Refernces

• 1、 Ganji, Lata R.,Gandhi, Lekha,Musturi, Venkataramana,Kanyalkar, Meena A.. "Design, synthesis, and evaluation of different scaffold derivatives against NS2B-NS3 protease of dengue virus". . p. 285 - 301. Retrieved 2020/11/19.
• 2、 Gong, Pei-Xue,Xu, Fangning,Cheng, Lu,Gong, Xu,Zhang, Jie,Gu, Wei-Jin,Han, Wei. "Iron-catalyzed domino decarboxylation-oxidation of α,β-unsaturated carboxylic acids enabled aldehyde C-H methylation". supporting information. p. 5905 - 5908. Retrieved 2021/06/18.