943-89-5 Usage
Description
4-Methoxycinnamic acid, also known as p-methoxycinnamate, is an organic compound that belongs to the class of cinnamic acid derivatives. It possesses a methoxy group attached to the 4-position of the cinnamic acid backbone, which gives it unique chemical and physical properties. 4-Methoxycinnamic acid is known for its ability to absorb ultraviolet (UV) radiation, making it a valuable ingredient in various applications.
Uses
Used in Cosmetics Industry:
4-Methoxycinnamic acid is used as a UV absorber for its ability to protect the skin from harmful UV radiation. It is commonly incorporated into sunscreens and other skincare products to provide broad-spectrum protection against both UVA and UVB rays, reducing the risk of skin damage, premature aging, and skin cancer.
Used in Pharmaceutical Industry:
4-Methoxycinnamic acid is used as a pharmaceutical intermediate in the synthesis of various drugs, particularly anti-adrenergic agents such as esmolol. This application takes advantage of its chemical properties to create compounds that can help regulate heart rate and blood pressure, providing therapeutic benefits for patients with cardiovascular conditions.
Used in Organic Synthesis:
4-Methoxycinnamic acid serves as a starting material in the organic synthesis of various compounds, including esters that are effective absorbers of UV radiation. This makes it a valuable component in the development of new products and materials with enhanced UV protection capabilities.
Used in Avenanthramide Alkaloid Synthesis:
In the synthesis of isolated avenanthramide alkaloids, 4-methoxycinnamic acid serves as a starting material. It can be converted into its acid chloride with thionyl chloride, yielding a 98% conversion rate. This conversion is crucial for the production of avenanthramides, which are bioactive compounds with potential health benefits.
Preparation
4-methoxycinnamic acid synthesis : In a 25-mL, roundbottomed flask, 4-methoxybenzaldehyde (0.804 mL, 6.61 mmol) (3), malonic acid (1.75 g, 16.8 mmol), and β-alanine (0.10 g, 1.12 mmol) were dissolved in pyridine (3.0 mL, 37.1 mmol) and heated under reflux for 90 minutes. After cooling to room temperature, the reaction mixture was placed in an ice bath and 8.0 mL of concentrated HCl was slowly added. The resulting white precipitate was collected by vacuum filtration, washed with cold water (2 x 10mL) and dried thoroughly. The product was recrystallized from absolute ethanol (~20 mL).Synthesis of 4-methoxycinnamic acid
Check Digit Verification of cas no
The CAS Registry Mumber 943-89-5 includes 6 digits separated into 3 groups by hyphens. The first part of the number,starting from the left, has 3 digits, 9,4 and 3 respectively; the second part has 2 digits, 8 and 9 respectively.
Calculate Digit Verification of CAS Registry Number 943-89:
(5*9)+(4*4)+(3*3)+(2*8)+(1*9)=95
95 % 10 = 5
So 943-89-5 is a valid CAS Registry Number.
InChI:InChI=1/C10H10O3/c1-13-9-5-2-8(3-6-9)4-7-10(11)12/h2-7H,1H3,(H,11,12)/b7-4+
943-89-5Relevant articles and documents
Highly regio- and stereoselective asymmetric bromoazidation of chiral α,β-unsaturated carboxylic acid derivatives: Scope and limitations
Hajra, Saumen,Bhowmick, Manishabrata,Sinha, Debarshi
, p. 9237 - 9240 (2006)
(Chemical Equation Presented) Lewis acid catalyzed asymmetric bromoazidation of chiral α,β-unsaturated carboxylic acid derivatives was performed using N-bromosuccinimide (NBS) and trimethylsilyl azide (TMSN 3) as the bromine and azide sources. Among the Lewis acids, Yb(OTf)3 was found to be the best catalyst. Regio- and anti-selectivity of 100% and moderate to good diastereoselectivity (up to 89:11) with good yields were obtained when Oppolzer's bornane sultam chiral auxilairy was used. Diastereoselectivity of > 95:05 was observed when (2S,5S)-2,5-diphenylpyrrolidine was used as the chiral auxiliary.
Reusable, magnetic Raney nickel based palladium catalysts for the Heck coupling in aqueous media
Bumagin, N. A.
, p. 2034 - 2040 (2021/11/05)
Hybrid materials based on Pd- and Cu-doped Raney nickel appeared to be highly efficient catalysts for the Heck reaction in aqueous media in the absence of organic cosolvents. The catalysts can be easily removed by an external magnet and reused without losing catalytic activity.
Synthesis and biological evaluation of 1,2,3-triazole hybrids of 4-methoxy ethyl cinnamate isolated from Hedychium spicatum (Sm) rhizomes: identification of antiproliferative lead actives against prostate cancer
Babu, K. Suresh,Kumari, G. Swarna,Nayak, V. Lakshma,Rao, Bhattu Ganga,Reddy, S. Divya,Siva, Bandi,Tiwari, Ashok K.
supporting information, (2021/10/01)
A series of 1, 2, 3- triazole hybrids (9a-9n) were synthesised from major phenolic constituent, 4-methoxy ethyl cinnamate (5) isolated from rhizomes of Hedychium spicatum (Sm), a traditional medicinal plant used in variety of disease conditions. All the synthesised analogues were tested for their in vitro antiproliferative potential against HCT 116 (colon cancer), A549 (lung cancer), DU-145 (prostate cancer), Hep G2 (hepatoma) and HEK-293 (normal) cell lines. Among the compounds tested, compounds 9i and 9k potently arrested proliferation of DU-145 (prostate cancer) cell line. Compound 9i displayed 20 times better antiproliferative potential than parent compound and almost identical inhibitory activity to that of the standard drug, doxorubicin. The flow cytometric analysis revealed that 9i arrested cells in G2/M phase of cell cycle and induced apoptosis. Overall, the hybrid derivative 9i was found to be a potential antiproliferative lead against prostate cancer.