7400-08-0 Usage
Description
p-Hydroxy-cinnamic acid, also known as 4-coumaric acid, is a hydroxy derivative of cinnamic acid with antioxidant properties. It is a major component of lignocellulose and has a role as a plant metabolite. This light yellow to beige crystalline powder has an aromatic smell and is soluble in various organic solvents such as methanol, ethanol, and DMSO. It is derived from synthesis and is known for its potential health benefits, including reducing the risk of cancer by decreasing the formation of carcinogenic nitrosamines.
Uses
1. Pharmaceutical Industry:
p-Hydroxy-cinnamic acid is used as an intermediate in the pharmaceutical industry for the production of various compounds. It can react with dimethyl sulfate to produce p-anisaldehyde, which is used in the synthesis of pharmaceuticals and fragrances. Additionally, it can react with acetaldehyde to produce p-hydroxycinnamaldehyde, which can be further oxidized to produce cinnamic acid. This acid can be directly oxidized to produce 4-Hydroxybenzoic acid, a compound with potential applications in the pharmaceutical industry, or reduced to produce 4-Hydroxybenzyl alcohol, another useful intermediate.
2. Perfume Industry:
In the perfume industry, p-Hydroxy-cinnamic acid serves as an intermediate for the synthesis of various fragrance compounds. The reaction with dimethyl sulfate to produce p-anisaldehyde is particularly important, as p-anisaldehyde is a key component in the creation of many perfumes.
3. Antioxidant Applications:
Due to its antioxidant properties, p-Hydroxy-cinnamic acid may be used in the development of antioxidant products, which can help protect cells from damage caused by free radicals. This application can be relevant in various industries, including the food and beverage industry, where antioxidants are used to extend the shelf life of products and maintain their quality.
4. Agricultural Applications:
A recent study suggests that p-Hydroxy-cinnamic acid may act as a chemical castrator in bees by altering the expression of genes required for ovary development. p-Hydroxy-cinnamic acid is common in pollen, a major constituent of the worker bee diet, but it is not found in queen bees' royal jelly. This information could be useful in the agricultural industry for managing bee populations and improving crop pollination.
Hazard
Moderately toxic.
Safety Profile
Moderarely toxic by
intraperitoneal route. Experimental
reproductive effects. When heated to
decomposition it emits acrid smoke and
fumes. See also COUMARIN
Check Digit Verification of cas no
The CAS Registry Mumber 7400-08-0 includes 7 digits separated into 3 groups by hyphens. The first part of the number,starting from the left, has 4 digits, 7,4,0 and 0 respectively; the second part has 2 digits, 0 and 8 respectively.
Calculate Digit Verification of CAS Registry Number 7400-08:
(6*7)+(5*4)+(4*0)+(3*0)+(2*0)+(1*8)=70
70 % 10 = 0
So 7400-08-0 is a valid CAS Registry Number.
InChI:InChI=1/C9H8O3/c1-6(9(11)12)7-2-4-8(10)5-3-7/h2-5,10H,1H2,(H,11,12)
7400-08-0Relevant articles and documents
Photoinduced Regioselective Olefination of Arenes at Proximal and Distal Sites
Ali, Wajid,Anjana, S. S.,Bhattacharya, Trisha,Chandrashekar, Hediyala B.,Goswami, Nupur,Guin, Srimanta,Maiti, Debabrata,Panda, Sanjib,Prakash, Gaurav,Saha, Argha,Sasmal, Sheuli,Sinha, Soumya Kumar
, p. 1929 - 1940 (2022/02/01)
The Fujiwara-Moritani reaction has had a profound contribution in the emergence of contemporary C-H activation protocols. Despite the applicability of the traditional approach in different fields, the associated reactivity and regioselectivity issues had
Novel ester derivative of cinnamates with different long alkoxy chain: synthesis, mesomorphic properties, biological evaluation
Bhalodiya, Pradip C.,Patel, Hemant N.,Parmar, Tejasvi H.,Sangani, Chetan B.,Rajani, Dhanji P.
, p. 1 - 25 (2021/07/07)
A novel series of liquid crystals involving cinnamate-based mesogenic units interlinked between aromatic ester and alkyl bromide were designed and synthesized. All target molecules were confirmed by IR, 1H NMR, 13C NMR, ESI-MS, and elemental analysis. The mesomorphic behavior of novel synthesized materials (P1–P18), (V1–V18), and (M1–M18) was investigated through a polarizing optical microscope, differential scanning calorimetry, and thermogravimetric analysis (TGA) analysis. The lower carbon chain substituted member showed nematic phase while compound possess higher carbon chain exhibited only SmC phase. Thermal stability is determined by TGA analysis. All the cinnamate derivatives were screened for their anti-microbial, anti-malarial, and anti-tuberculosis potency. Among them, most of the derivatives exhibited outstanding anti-bacterial and anti-tuberculosis activity. Some derivatives also exhibited potent anti-fungal activity.
Dual Nickel/Ruthenium Strategy for Photoinduced Decarboxylative Cross-Coupling of α,β-Unsaturated Carboxylic Acids with Cycloketone Oxime Esters
Gao, Ang,Jiang, Run-Chuang,Liu, Chuang-Chuang,Liu, Qi-Le,Lu, Xiao-Yu,Xia, Ze-Jie
supporting information, p. 8829 - 8842 (2021/06/30)
Herein, a dual nickel/ruthenium strategy is developed for photoinduced decarboxylative cross-coupling between α,β-unsaturated carboxylic acids and cycloketone oxime esters. The reaction mechanism is distinct from previous photoinduced decarboxylation of α,β-unsaturated carboxylic acids. This reaction might proceed through a nickelacyclopropane intermediate. The C(sp2)-C(sp3) bond constructed by the aforementioned reaction provides an efficient approach to obtaining various cyanoalkyl alkenes, which are synthetically valuable organic skeletons in organic and medicinal chemistry, under mild reaction conditions. The protocol tolerates many critical functional groups and provides a route for the modification of complex organic molecules.