943-89-5

Basic information

• Product Name: 4-METHOXYCINNAMIC ACID
• Synonyms: 4-METHOXYCINNAMIC ACID ABOUT 98%;trans-4-Methoxycinnamic acid, 98+%;(E)-4-Methoxycinnamic acid;4-Methoxy-trans-cinnamic acid;p-Methoxy-trans-cinnamic acid;4-Methoxycinnamic acid;4-Methoxycinnamic acid >=98.0% (GC);trans-4-MethoxyClnnamic acid
• CAS NO: 943-89-5
• Molecular Formula: C₁₀H₁₀O₃
• Molecular Weight: 178.18
• EINECS: 213-405-4
• Product Categories: Benzenes
• Mol File: 943-89-5.mol
• Article Data: 214

Chemical Properties

• Melting Point: 173.5 °C(lit.)
• Boiling Point: 342.6 °C at 760 mmHg
• Flash Point: 138.5 °C
• Appearance: /
• Density: 1.195 g/cm³
• Storage Temp.: Keep in dark place,Sealed in dry,Room Temperature
• Solubility: Soluble in ethanol, ethyl acetate and other organic solvents.
• PKA: 4.60±0.10(Predicted)
• BRN: 510468
• CAS DataBase Reference: 4-METHOXYCINNAMIC ACID(CAS DataBase Reference)
• NIST Chemistry Reference: 4-METHOXYCINNAMIC ACID(943-89-5)
• EPA Substance Registry System: 4-METHOXYCINNAMIC ACID(943-89-5)

Safety Data

• Hazard Codes: Xi
• Statements: 36/37/38
• Safety Statements: 26-37/39
• WGK Germany: 3
• RTECS: UD3391300
• F: 8
• TSCA: Yes
• HazardClass: IRRITANT
• Hazardous Substances Data: 943-89-5(Hazardous Substances Data)

Usage

Uses

Esters derived from trans-4-methoxycinnamic acid are effective absorbers of UV radiation. The starting material was trans-4-methoxycinnamic acid and 3,5dimethoxybenzoic acid methyl ester in isolated avenanthramide alkaloids synthsis. trans-4-Methoxycinnamic acid was converted into its acid chloride (yield 98%) with thionyl chloride. Employed in organic synthesis of pharmaceutical intermediates, synthetic anti-adrenergic drugs esmolol, cosmetics ultraviolet absorption.

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

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+

Upstream product

• 3901-07-3 3-(4-methoxy-phenyl)acrylic acid methyl ester 
• 31448-61-0 2,3-dibromo-3-(4-methoxy-phenyl)-propionic acid 
• 79-20-9 acetic acid methyl ester 
• 123-11-5 4-methoxy-benzaldehyde 
• 141-82-2 malonic acid 
• 186581-53-3 diazomethane 
• 7400-08-0 p-Coumaric Acid 
• 24393-56-4 ethyl (E)-3-(4-methoxyphenyl)prop-2-enoate 
• 51978-98-4 5-[(E)-2-(4-methoxyphenyl)-1-ethenyl]-3-methyl-4-nitroisoxazole 
• 108-24-7 acetic anhydride 
• 132149-07-6 (E)-3-(4-Methoxy-phenyl)-acrylic acid 1-(4-methoxy-phenyl)-ethyl ester 
• 82410-33-1 onjisaponin A 
• 84062-32-8 verbascoside A 
• 104-92-7 1-bromo-4-methoxy-benzene 

Downstream Products

• 101595-22-6 3-(4-methoxy-phenyl)-3-(4-methylsulfanyl-phenyl)-propionic acid 
• 637-69-4 4-Methoxystyrene 
• 5406-18-8 3-(p-methoxyphenyl)-1-propanol 
• 24393-56-4 ethyl (E)-3-(4-methoxyphenyl)prop-2-enoate 
• 23784-83-0 (E)-N,N-diethyl-3-(4-methoxyphenyl)propenamide 
• 19950-54-0 meso-3,4-bis-(4-methoxy-phenyl)-adipic acid 
• 19950-53-9 racem.-3.4-bis-(4-methoxy-phenyl)-adipic acid 
• 59259-39-1 (+/-)-3endo-(4-methoxy-phenyl)-norborn-5-ene-2exo-carboxylic acid 
• 59259-39-1 (+/-)-3exo-(4-methoxy-phenyl)-norborn-5-ene-2endo-carboxylic acid 
• 81509-20-8 (+/-)-6endo-hydroxy-5exo-iodo-3exo-(4-methoxy-phenyl)-norbornane-2endo-carboxylic acid-lactone 
• 35582-69-5 bis-3,3-(p-methoxyphenyl)-propionic acid 
• 133793-09-6 4-methoxy-trans-cinnamic acid-(2-methoxy-phenyl ester) 
• 85676-74-0 (E)-1-chloro-2-(4-methoxystyryl)benzene 
• 109386-28-9 (±)-7-hydroxy-4-(4-methoxyphenyl)-3,4-dihydrocoumarin 

Relevant articles and documents

Highly regio- and stereoselective asymmetric bromoazidation of chiral α,β-unsaturated carboxylic acid derivatives: Scope and limitations

(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

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

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.