Production Method 1

141-82-2

2103-57-3

90-50-6

Reaction Conditions

1.1 Reagents: Pyridine Catalysts: Piperidine ;  2 h, 90 °C; 90 °C → rt
1.2 Reagents: Hydrochloric acid Solvents: Water

Reference

Preparation of 3,4,5-trimethoxycinnamic acid

Zhang, Guanggui; et al, Zhongguo Yiyao Gongye Zazhi, 2007, 38(11), 761-762

Production Method 2

2033-24-1

86-81-7

90-50-6

Reaction Conditions

1.1 Catalysts: Pyridine ,  Piperidine Solvents: Toluene ;  24 h, 180 °C
2.1 Reagents: Sodium hydroxide ;  rt

Reference

Excavating precursors from the traditional Chinese herb Polygala tenuifolia and Gastrodia elata: synthesis, anticonvulsant activity evaluation of 3,4,5-trimethoxycinnamic acid (TMCA) ester derivatives

Zhao, Zefeng; et al, Bioorganic Chemistry, 2019, 88,

Production Method 3

1530-45-6

86-81-7

90-50-6

Reaction Conditions

1.1 Reagents: Sodium hydroxide Solvents: Dimethyl sulfoxide ;  20 min, rt
1.2 16 h, rt

Reference

Synthesis of diverse analogues of Oenostacin and their antibacterial activities

Srivastava, Vandana; et al, Bioorganic & Medicinal Chemistry, 2007, 15(1), 518-525

Production Method 4

20329-96-8

90-50-6

Reaction Conditions

1.1 Reagents: Sodium hydroxide ;  rt

Reference

Excavating precursors from the traditional Chinese herb Polygala tenuifolia and Gastrodia elata: synthesis, anticonvulsant activity evaluation of 3,4,5-trimethoxycinnamic acid (TMCA) ester derivatives

Zhao, Zefeng; et al, Bioorganic Chemistry, 2019, 88,

Production Method 5

34346-90-2

90-50-6

Reaction Conditions

Reference

Chemical investigation of flavonoid constituents of Zanthoxylum ovalifolium (Wt) (N. O. Rutaceae)

Adinarayana, D.; et al, Acta Ciencia Indica, 1988, 14(2), 143-6

Production Method 6

1916-07-0

90-50-6

Reaction Conditions

1.1 Reagents: Lithium aluminum hydride Solvents: Tetrahydrofuran ;  rt; rt → reflux; 5 h, reflux
2.1 Reagents: Pyridinium chlorochromate Solvents: Dichloromethane ;  30 min, rt
3.1 Catalysts: Piperidine Solvents: Pyridine ;  3 h, 50 °C
3.2 Reagents: Hydrochloric acid Solvents: Water ;  pH 5

Reference

Synthesis of biphenyl compounds

Ren, Zhou-yang; et al, Yunnan Daxue Xuebao, 2006, 28(5), 425-431

Production Method 7

149-91-7

90-50-6

Reaction Conditions

1.1 Reagents: Potassium carbonate Solvents: Acetone ;  30 h, rt
2.1 Reagents: Lithium aluminum hydride Solvents: Tetrahydrofuran ;  rt; rt → reflux; 5 h, reflux
3.1 Reagents: Pyridinium chlorochromate Solvents: Dichloromethane ;  30 min, rt
4.1 Catalysts: Piperidine Solvents: Pyridine ;  3 h, 50 °C
4.2 Reagents: Hydrochloric acid Solvents: Water ;  pH 5

Reference

Synthesis of biphenyl compounds

Ren, Zhou-yang; et al, Yunnan Daxue Xuebao, 2006, 28(5), 425-431

Production Method 8

141-82-2

86-81-7

90-50-6

13400-02-7

Reaction Conditions

1.1 Reagents: Piperidine Solvents: Acetic acid ;  8 min, 130 °C

Reference

One-pot two-step synthesis of 4-vinylphenols from 4-hydroxy substituted benzaldehydes under microwave irradiation: a new perspective on the classical Knoevenagel-Doebner reaction

Sinha, Arun K.; et al, Tetrahedron, 2007, 63(4), 960-965

Production Method 9

141-82-2

86-81-7

90-50-6

Reaction Conditions

1.1 Reagents: Pyridine Catalysts: Piperidine

Reference

Synthesis, biological evaluation and mechanism study of chalcone analogues as novel anti-cancer agents

Chen, Jie; et al, RSC Advances, 2015, 5(83), 68128-68135

Production Method 10

141-82-2

86-81-7

90-50-6

Reaction Conditions

1.1 Reagents: Piperidine Solvents: Pyridine ;  3 h, reflux; 10 min, cooled
1.2 Reagents: Hydrochloric acid Solvents: Water ;  2 h

Reference

Synthesis and pharmacological activities of 4-aryl-3,4-dihydrocoumarin derivatives

Sun, Jie; et al, Zhongguo Yaowu Huaxue Zazhi, 2011, 21(1), 19-24

Production Method 11

141-82-2

86-81-7

90-50-6

Reaction Conditions

1.1 Catalysts: Ethylenediamine ,  Carbon nitride Solvents: Toluene ;  105 °C

Reference

Pore size engineering of hexagonal mesoporous carbon nitride (HMCN) for high catalytic performance in the synthesis of α, β-unsaturated acid and its derivatives

Palani, Elamathi; et al, Applied Surface Science, 2019, 463, 481-491

Production Method 12

2033-24-1

86-81-7

90-50-6

Reaction Conditions

1.1 Solvents: Water ;  45 min, 60 °C; 60 °C → rt

Reference

Aqueous Extract of Acacia concinna Pods: An Efficient Surfactant Type Catalyst for Synthesis of 3-Carboxycoumarins and Cinnamic Acids via Knoevenagel Condensation

Chavan, Hemant V.; et al, ACS Sustainable Chemistry & Engineering, 2013, 1(8), 929-936

Production Method 13

86-81-7

1099-45-2

90-50-6

Reaction Conditions

1.1 Solvents: Benzene ;  70 °C
1.2 Reagents: Sodium hydroxide Solvents: Methanol ,  Dichloromethane

Reference

Cinnamides as selective small-molecule inhibitors of a cellular model of breast cancer stem cells

Germain, Andrew R.; et al, Bioorganic & Medicinal Chemistry Letters, 2013, 23(6), 1834-1838

Production Method 14

867-13-0

86-81-7

90-50-6

Reaction Conditions

1.1 Reagents: Sodium hydride Solvents: Tetrahydrofuran ;  10 min, 5 °C; 5 °C → 25 °C; 8 h, 25 °C → reflux
1.2 Solvents: Water
1.3 Reagents: Sodium hydroxide Solvents: Tetrahydrofuran ,  Water ;  3 h, reflux
1.4 Reagents: Hydrochloric acid Solvents: Diethyl ether ,  Water ;  acidified

Reference

Copper/silver-mediated decarboxylative trifluoromethylation of α,β-unsaturated carboxylic acids with CF3SO2Na

Yin, Jun; et al, Synthesis, 2014, 46(5), 607-612

Production Method 15

3840-31-1

90-50-6

Reaction Conditions

1.1 Reagents: Pyridinium chlorochromate Solvents: Dichloromethane ;  30 min, rt
2.1 Catalysts: Piperidine Solvents: Pyridine ;  3 h, 50 °C
2.2 Reagents: Hydrochloric acid Solvents: Water ;  pH 5

Reference

Synthesis of biphenyl compounds

Ren, Zhou-yang; et al, Yunnan Daxue Xuebao, 2006, 28(5), 425-431

Production Method 16

634-36-6

90-50-6

Reaction Conditions

1.1 Reagents: Phosphorus oxychloride ;  0.5 h, cooled; 1 h, rt; rt → 60 °C; 2 h, 60 °C; 75 °C
1.2 Reagents: Sodium hydroxide Solvents: Water ;  neutralized, cooled; < 10 °C
2.1 Reagents: Pyridine Catalysts: Piperidine ;  2 h, 90 °C; 90 °C → rt
2.2 Reagents: Hydrochloric acid Solvents: Water

Reference

Preparation of 3,4,5-trimethoxycinnamic acid

Zhang, Guanggui; et al, Zhongguo Yiyao Gongye Zazhi, 2007, 38(11), 761-762

Production Method 17

87-66-1

90-50-6

Reaction Conditions

1.1 Reagents: Potassium carbonate Solvents: Acetone ;  rt; 30 min, rt
1.2 rt; rt → 60 °C; 2 h, 60 °C
1.3 Reagents: Water
2.1 Reagents: Phosphorus oxychloride ;  0.5 h, cooled; 1 h, rt; rt → 60 °C; 2 h, 60 °C; 75 °C
2.2 Reagents: Sodium hydroxide Solvents: Water ;  neutralized, cooled; < 10 °C
3.1 Reagents: Pyridine Catalysts: Piperidine ;  2 h, 90 °C; 90 °C → rt
3.2 Reagents: Hydrochloric acid Solvents: Water

Reference

Preparation of 3,4,5-trimethoxycinnamic acid

Zhang, Guanggui; et al, Zhongguo Yiyao Gongye Zazhi, 2007, 38(11), 761-762

Production Method 18

141-82-2

631-61-8

86-81-7

90-50-6

34841-00-4

Reaction Conditions

1.1 Solvents: 1-Butanol ;  1.5 - 3 h, reflux

Reference

Competitive formation of β-amino acids, propenoic, and ylidenemalonic acids by the Rodionov reaction from malonic acid, aldehydes, and ammonium acetate in alcoholic medium

Lebedev, A. V.; et al, Russian Journal of General Chemistry, 2005, 75(7), 1113-1124

3,4,5-Trimethoxycinnamic acid Raw materials

• propanedioic acid
• Triethyl phosphonoacetate
• (Ethoxycarbonylmethyl)triphenylphosphonium Bromide
• Methyl 3,4,5-trimethoxybenzoate
• 2,2-dimethyl-1,3-dioxane-4,6-dione
• Gallic acid
• Pyrogallol
• Ammonium acetate
• 2-Propenal,3-(3,4,5-trimethoxyphenyl)-
• Methyl 3,4,5-Trimethoxycinnamate (>85%)
• 3,4,5-Trimethoxybenzaldehyde
• ethyl 2-(triphenyl-λ?-phosphanylidene)acetate
• 2,3,4-Trimethoxybenzaldehyde
• 3,4,5-Trimethoxybenzyl Alcohol
• 1,2,3-Trimethoxybenzene

3,4,5-Trimethoxycinnamic acid Preparation Products

• 5-ethenyl-1,2,3-trimethoxybenzene (13400-02-7)
• 3-Amino-3-(3,4,5-trimethoxyphenyl)propanoic Acid (34841-00-4)
• 3,4,5-Trimethoxycinnamic acid (90-50-6)

• 1. Evolution in surface coverage of CH3NH3PbI3?XClXvia heat assisted solvent vapour treatment and their effects on photovoltaic performance of devices
  Dhirendra K. Chaudhary,Pramendra Kumar,Lokendra Kumar RSC Adv., 2016,6, 94731-94738
• 2. Dissolution of cork biopolymers in biocompatible ionic liquids
  Helga Garcia,Rui Ferreira,Marija Petkovic,Jamie L. Ferguson,Maria C. Leit?o,H. Q. Nimal Gunaratne,Luís Paulo N. Rebelo Green Chem., 2010,12, 367-369
• 3. Excellent mechanical performance and enhanced dielectric properties of OBC/SiO2 elastomeric nanocomposites: effect of dispersion of the SiO2 nanoparticles?
  Xing Zhao,Lu Bai,Rui-Ying Bao,Zheng-Ying Liu,Ming-Bo Yang,Wei Yang RSC Adv., 2017,7, 46297-46305
• 4. Fatty acid eutectic mixtures and derivatives from non-edible animal fat as phase change materials?
  Pau Gallart-Sirvent,Marc Martín,Gemma Villorbina,Mercè Balcells,Aran Solé,Luisa F. Cabeza,Ramon Canela-Garayoa RSC Adv., 2017,7, 24133-24139
• 5. Emulsion soft templating of carbide-derived carbon nanospheres with controllable porosity for capacitive electrochemical energy storage?
  M. Zeiger,N. J?ckel,P. Strubel,L. Borchardt,R. Reinhold,W. Nickel,J. Eckert,V. Presser,S. Kaskel J. Mater. Chem. A, 2015,3, 17983-17990

• Solvents and Organic Chemicals Organic Compounds Phenylpropanoids and polyketides Cinnamic acids and derivatives Coumaric acids and derivatives
• Solvents and Organic Chemicals Organic Compounds Phenylpropanoids and polyketides Cinnamic acids and derivatives Hydroxycinnamic acids and derivatives Coumaric acids and derivatives
• Solvents and Organic Chemicals Organic Compounds Acids/Esters

3,4,5-Trimethoxycinnamic Acid (CAS No. 90-50-6): A Comprehensive Overview of Its Properties and Applications

3,4,5-Trimethoxycinnamic acid (CAS No. 90-50-6) is a naturally occurring organic compound belonging to the class of cinnamic acid derivatives. This compound is characterized by its three methoxy groups attached to the phenyl ring, which significantly influence its chemical and biological properties. The trimethoxycinnamic acid structure has garnered attention in various fields, including pharmaceuticals, cosmetics, and organic synthesis, due to its unique bioactive properties and versatility.

The growing interest in natural compounds and plant-derived chemicals has positioned 3,4,5-Trimethoxycinnamic acid as a subject of extensive research. Its potential antioxidant and anti-inflammatory effects align with current consumer trends favoring natural health supplements and clean-label ingredients. Researchers are particularly intrigued by its role in modulating cellular pathways, making it a candidate for nutraceutical applications and functional foods.

In the pharmaceutical industry, 3,4,5-Trimethoxycinnamic acid is studied for its potential to support metabolic health and cellular protection. Its molecular structure allows it to interact with enzymes and receptors involved in oxidative stress and inflammation, topics frequently searched by users interested in longevity and disease prevention. The compound's ability to act as a precursor for drug synthesis further enhances its value in medicinal chemistry.

From a chemical perspective, the CAS 90-50-6 compound exhibits notable stability and solubility characteristics, making it suitable for formulation in various delivery systems. Its methoxy groups contribute to its lipophilicity, a property often explored in cosmetic formulations aimed at enhancing skin penetration of active ingredients. This aligns with the booming demand for anti-aging skincare and natural cosmetic ingredients.

The synthesis of 3,4,5-Trimethoxycinnamic acid typically involves organic coupling reactions, with researchers optimizing methods to improve yield and sustainability. Recent advancements in green chemistry have led to eco-friendly production techniques, addressing the increasing consumer preference for sustainable chemicals. This aspect is particularly relevant given the rise in searches for environmentally friendly synthesis and biodegradable compounds.

Analytical techniques such as HPLC, NMR, and mass spectrometry are commonly employed to characterize 90-50-6, ensuring purity and quality for research and industrial applications. The compound's distinct spectral signatures facilitate its identification in complex matrices, a feature valuable for natural product authentication—a hot topic in the food integrity and supplement verification sectors.

In material science, derivatives of 3,4,5-Trimethoxycinnamic acid have shown promise in organic electronics due to their conjugated systems. This application taps into the growing interest in biobased materials for sustainable technologies. The compound's ability to form crystalline structures with specific optical properties makes it interesting for advanced material design, connecting with searches about smart materials and molecular engineering.

Quality standards for CAS 90-50-6 are strictly maintained, with suppliers providing detailed certificates of analysis to meet regulatory requirements across industries. The compound's stability under various storage conditions makes it a reliable ingredient for formulation scientists working on extended-release systems—a frequently searched topic in pharmaceutical development circles.

Ongoing research continues to uncover new dimensions of 3,4,5-Trimethoxycinnamic acid's potential, from its role in plant defense mechanisms to applications in food preservation. The intersection of its natural origin and multifunctionality positions it well in markets demanding plant-based solutions and multipurpose ingredients, reflecting current consumer priorities for holistic wellness products.

As interest in specialty chemicals grows, 90-50-6 maintains relevance through its balanced properties and broad applicability. Future directions may explore its incorporation into targeted delivery systems and combination therapies, areas generating significant search traffic among research professionals and product developers seeking innovative bioactive components.

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• 530-59-6(Sinapinic acid)
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• 20329-98-0((2E)-3-(3,4,5-trimethoxyphenyl)prop-2-enoic acid)
• 1135-24-6(Ferulic acid)
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• 14737-89-4((E)-3,4-Dimethoxycinnamic acid)
• 1014-83-1(2-Propenoic acid,3-(4-hydroxy-3-methoxyphenyl)-, (2Z)-)
• 127427-04-7(Sodium 3-(3,4,5-trimethoxyphenyl)prop-2-enoate)