4657-33-4

Basic information

• Product Name: butyl 4'-hydroxy-3'-methoxycinnamate
• Synonyms: butyl 4'-hydroxy-3'-methoxycinnamate;3-(3-Methoxy-4-hydroxyphenyl)propenoic acid butyl ester;3-(4-Hydroxy-3-methoxyphenyl)acrylic acid butyl ester;3-Methoxy-4-hydroxybenzeneacrylic acid butyl ester;Butyl Ferulate;Einecs 225-100-3
• CAS NO: 4657-33-4
• Molecular Formula: C₁₄H₁₈O₄
• Molecular Weight: 250.29032
• EINECS: 225-100-3
• Mol File: 4657-33-4.mol
• Article Data: 21

Chemical Properties

• Boiling Point: 377.9°Cat760mmHg
• Flash Point: 137.2°C
• Appearance: /
• Density: 1.125g/cm³
• CAS DataBase Reference: butyl 4'-hydroxy-3'-methoxycinnamate(CAS DataBase Reference)
• NIST Chemistry Reference: butyl 4'-hydroxy-3'-methoxycinnamate(4657-33-4)
• EPA Substance Registry System: butyl 4'-hydroxy-3'-methoxycinnamate(4657-33-4)

Safety Data

• Hazardous Substances Data: 4657-33-4(Hazardous Substances Data)

Upstream product

• 1135-24-6 3-(4-hydroxy-3-methoxyphenyl)acrylic acid 
• 71-36-3 butan-1-ol 
• 56640-69-8 buten-1-ol 
• 1135-24-6 (E)-3-(4-hydroxy-3-methoxyphenyl)acrylic acid 
• 121-33-5 vanillin 
• 77795-22-3 4-benzyloxy-3-methoxycinnamic acid 
• 22329-76-6 methyl ferulate 
• 28028-62-8 ethyl ferulate 
• 4046-02-0 ethyl 4-hydroxy-3-methoxycinnamate 
• 2426-87-1 3-methoxy-4-(phenylmethoxy)benzaldehyde 
• 948827-71-2 (E)-3-(4-Benzyloxy-3-methoxy-phenyl)-acrylic acid butyl ester 

Downstream Products

• 515835-75-3 butyl 3-[4-(3,4,5-triacetyloxybenzoyloxy)-3-methoxyphenyl]-2-propenoate 
• 1135-24-6 (E)-3-(4-hydroxy-3-methoxyphenyl)acrylic acid 

Relevant articles and documents

Studies on temperature dependent kinetics of Aspergillus awamori feruloyl esterase in water solutions

The initial reaction rate (V 0) for the esterification reaction of feruloyl esterase (FAE-II) at different temperatures (288, 298, 308, 318, 328, 338, 348, and 358 K) and various ethyl ferulate concentrations [(2, 4, 6, 8, 10, 12, 14, and 16) ×

Structure?Activity Relationships of Cinnamate Ester Analogues as Potent Antiprotozoal Agents

Protozoal infections are still a global health problem, threatening the lives of millions of people around the world, mainly in impoverished tropical and sub-tropical regions. Thus, in view of the lack of efficient therapies and increasing resistances against existing drugs, this study describes the antiprotozoal potential of synthetic cinnamate ester analogues and their structure-activity relationships. In general, Leishmania donovani and Trypanosoma brucei were quite susceptible to the compounds in a structure-dependent manner. Detailed analysis revealed a key role of the substitution pattern on the aromatic ring and a marked effect of the side chain on the activity against these two parasites. The high antileishmanial potency and remarkable selectivity of the nitro-aromatic derivatives suggested them as promising candidates for further studies. On the other hand, the high in vitro potency of catechol-type compounds against T. brucei could not be extrapolated to an in vivo mouse model.

Long Chain Alkyl Esters of Hydroxycinnamic Acids as Promising Anticancer Agents: Selective Induction of Apoptosis in Cancer Cells

Cancer is the major cause of morbidity and mortality worldwide. Hydroxycinnamic acids (HCAs) are naturally occurring compounds and their alkyl esters may possess enhanced biological activities. We evaluated C4, C14, C16, and C18 alkyl esters of p-coumaric, ferulic, sinapic, and caffeic acids (19 compounds) for their cytotoxic activity against four human cancer cells and also examined their effect on cell cycle alteration and apoptosis induction. The tetradecyl (1c) and hexadecyl (1d) esters of p-coumaric acid and tetradecyl ester of caffeic acid (4c), but not the parental HCAs, were selectively effective against MOLT-4 (human lymphoblastic leukemia) cells with IC50 values of 0.123 ± 0.012, 0.301 ± 0.069 and 1.0 ± 0.1 μM, respectively. Compounds 1c, 1d, and 4c significantly increased apoptotic cells in sub-G1 phase and activated the caspase-3 enzyme in MOLT-4 cells. Compound 1c was 15.4 and 23.6 times more potent than doxorubicin and cisplatin, respectively, against the drug resistant MES-SA-DX5 uterine sarcoma cells. These p-coumarate esters were several times less effective against NIH/3T3 fibroblast cells. Docking studies showed that 1c may cause cytotoxicity by interaction with carbonic anhydrase IX. In conclusion, long chain alkyl esters of p-coumaric acid are promising scaffolds for selective apoptosis induction in cancer cells.

Study of the Effect of Lateral Substitution on Mesogenic Behavior with Reference to -CH=CH- Unit

A novel cinnamate ester homologous series has been synthesized and studied with a view to understanding and establishing the effects of molecular structure on liquid crystal (LC) properties with a focus on the highly polar methoxy group as a lateral substituent. The series consists of twelve homologs; of which C1-C5 are nonmesogenic, and the rest of the homologs are enantiotropically smectogenic or and nematogenic. The texture of nematic phases is threaded or Schlieren and that of the smectic is either smectic A or C, as recognized and determined through an optical polarizing microscope equipped with a heating stage. The Sm-N I and N-I transition curves exhibit odd-even effects and behave in normalmanner. The Cr-IMbehaves in normalmanner. Analytical and spectral data confirm the molecular structures of homologs. The average thermal stabilities for smectic and nematic are 125.3 C and 129.8 C, respectively, whose total mesophase length varies from 13 C to 51 C. Some LC properties of present series are compared with the structurally similar known series.