1014-83-1

Basic information

• Product Name: CIS-FERULICACID
• Synonyms: CIS-FERULICACID;(Z)-3-(3-Methoxy-4-hydroxyphenyl)propenoic acid;(Z)-3-(4-Hydroxy-3-methoxyphenyl)acrylic acid;(Z)-3-(4-Hydroxy-3-methoxyphenyl)propenoic acid;3-Methoxy-4-hydroxy-cis-cinnamic acid
• CAS NO: 1014-83-1
• Molecular Formula: C₁₀H₁₀O₄
• Molecular Weight: 194.18
• EINECS: 214-490-0
• Mol File: 1014-83-1.mol

Chemical Properties

• Boiling Point: 372.3°Cat760mmHg
• Flash Point: 150.5°C
• Appearance: /
• Density: 1.316g/cm³
• Vapor Pressure: 3.34E-06mmHg at 25°C
• Refractive Index: 1.626
• CAS DataBase Reference: CIS-FERULICACID(CAS DataBase Reference)
• NIST Chemistry Reference: CIS-FERULICACID(1014-83-1)
• EPA Substance Registry System: CIS-FERULICACID(1014-83-1)

Safety Data

• Hazardous Substances Data: 1014-83-1(Hazardous Substances Data)

Usage

Uses

Used in Pharmaceutical Industry:
CIS-FERULICACID is used as a therapeutic agent for its antioxidant, anti-inflammatory, and neuroprotective properties. It has been shown to exhibit potential benefits in the treatment of various diseases, including neurodegenerative disorders, cardiovascular diseases, and cancer. The antioxidant properties of CIS-FERULICACID help neutralize free radicals, reducing oxidative stress and inflammation in the body.
Used in Food Industry:
CIS-FERULICACID is used as a natural preservative and flavor enhancer in the food industry. Its antioxidant properties help extend the shelf life of perishable products by preventing oxidation and spoilage. Additionally, it contributes to the unique taste and aroma of certain food products, such as bread, cereals, and beverages.
Used in Cosmetic Industry:
CIS-FERULICACID is used as an active ingredient in cosmetic products due to its antioxidant, anti-inflammatory, and skin-protective properties. It is commonly found in skincare products, such as creams, lotions, and serums, to help reduce the signs of aging, improve skin elasticity, and protect the skin from environmental stressors.
Used in Agriculture:
CIS-FERULICACID is used in the agricultural industry as a natural pesticide and growth promoter. Its antioxidant and anti-inflammatory properties help protect plants from various diseases and pests, promoting healthy growth and increased crop yields.
Used in Nanotechnology:
CIS-FERULICACID has potential applications in the field of nanotechnology, particularly in the development of novel drug delivery systems. Its antioxidant and anti-inflammatory properties make it a promising candidate for the targeted delivery of therapeutic agents, enhancing their bioavailability and therapeutic outcomes.

InChI:InChI=1/C10H10O4/c1-14-9-6-7(2-4-8(9)11)3-5-10(12)13/h2-6,11H,1H3,(H,12,13)/b5-3-

Upstream product

• 1062606-31-8 (8R,7'S,8'R)-5'-methoxylariciresinol 9'-O-β-D-(6-O-Z-4-hydroxy-3-methoxycinnamoyl)glucopyranoside 
• 1062606-14-7 (8R,7'S,8'R)-5,5'-dimethoxylariciresinol 9'-O-β-D-(6-O-Z-4-hydroxy-3-methoxycinnamoyl)glucopyranoside 
• 1135-24-6 (E)-3-(4-hydroxy-3-methoxyphenyl)acrylic acid 

Downstream Products

• 123-08-0 4-hydroxy-benzaldehyde 
• 121-33-5 vanillin 
• 66648-43-9 (E)-N-feruloyltyramine 
• 1135-24-6 (E)-3-(4-hydroxy-3-methoxyphenyl)acrylic acid 

Relevant articles and documents

Three secoiridoid glucosides from Jasminum lanceolarium

Three new secoiridoid glycosides, jaslanceosides C E, in addition to jaslanceosides A and B. 10-hydroxyoleoside dimethyl ester and jasminoside were isolated from the leaves and stems of Jasminum lanceolarium. The structures of these compounds were elucidated on the basis of spectral analysis and chemical correlation with known compounds.

New cardenolide and acylated lignan glycosides from the aerial parts of Asclepias curassavica

Three new cardenolide glycosides and six new acylated lignan glycosides were obtained along with nineteen known compounds from the aerial parts of Asclepias curassavica L. (Asclepiadaceae). The structure of each compound was determined based on interpreta

Visible-light-induced oxidation of trans-ferulic acid by TiO2 photocatalysis

The oxidation of trans-ferulic acid (C10H10O 4) in aqueous TiO2 dispersion occurs via the formation of a charge-transfer complex on the TiO2 surface that is able to absorb visible light (λ ≥ 400 nm). The main product is CO2, whereas secondary oxidation products are organic species such as vanillin, caffeic acid, homovanillic acid, and vanillylmandelic acid. Oxidation through the formation of a charge-transfer complex occurs only in the presence of specific TiO2 samples. Experiments in the absence of oxygen, in the presence of bromate ions and by using a phosphate-modified TiO2, have been carried out for investigating the reaction mechanism. In order to study the interaction between trans-ferulic acid and TiO2 surface and to characterize the charge-transfer complex, UV-Vis diffuse reflectance and FT-IR spectroscopies have been used. FT-IR characterization of TiO2 samples in contact with the aqueous trans-ferulic acid solution indicates that the charge-transfer complex formation occurs via adsorption of bidentate ferulate species.

Antioxidative properties of phenolic antioxidants isolated from corn steep liquor

With the immersion of corn into dilute sulfur oxide during starch-manufacturing processes, corn steep liquor (CSL) remains as leftover material. CSL is often used for fermentation, but its components are not fully understood. To determine the properties of CSL, 12 p-coumaric acid-related compounds were isolated from an ethyl acetate extract of CSL with the guidance of antioxidative activity on the rabbit erythrocyte membrane ghost system. The activity of these compounds was compared against oxidative damages, and it was elucidated that the activity of p-coumaric acid derivatives was mainly affected by their functional groups at the 3-position and less, by the conjugated side chain. Moreover, p-coumaric acid derivatives exhibited inhibitory activity stronger than that of tocopherols and ascorbic acid on peroxynitrite-mediated lipoprotein nitration. These findings that p-coumaric acid derivatives, which might play a beneficial role against oxidative damage, exist in CSL suggest this byproduct might be a useful resource of phenolic antioxidants.

Stability of Hydroxycinnamic Acid Derivatives, Flavonol Glycosides, and Anthocyanins in Black Currant Juice

The stability of phenolic compounds was followed in black currant juice at ambient temperatures (in light and in dark conditions) and at +4 °C for a year. Analyses were based on high-performance liquid chromatography-diode-array detection-electrospray ionization-mass spectrometry (or tandem mass spectrometry) and high-performance liquid chromatography-diode-array detection-electrospray ionization-quadrupole time-of-flight mass spectrometry methods supported by nuclear magnetic resonance after selective high-performance liquid chromatography isolation. Altogether, 43 metabolites were identified, of which 2-(Z)-p-coumaroyloxymethylene-4-β-d-glucopyranosyloxy-2-(Z)-butenenitrile, 2-(E)-caffeoyloxymethylene-4-β-d-glucopyranosyloxy-2-(Z)-butenenitrile, 1-O-(Z)-p-coumaroyl-β-d-glucopyranose, (Z)-p-coumaric acid 4-O-β-d-glucopyranoside, and (Z)-p-coumaric acid were novel findings in black currant juice. Hydroxycinnamic acid derivatives degraded 20-40% at room temperature during one year of storage, releasing free hydroxycinnamic acids. O-Glucosides of hydroxycinnamic acid compounds were the most stable, followed by O-acylquinic acids, acyloxymethyleneglucosyloxybutenenitriles, and O-acylglucoses. Light induced the isomerization of (E)-coumaric acid compounds into corresponding Z-isomers. Flavonol glycosides stayed fairly stable. Flavonol aglycones were derived mainly from malonylglucosides. Over 90% of anthocyanins were lost at room temperature in a year, practically independent of light. Storage at low temperatures, preferably excluding light, is necessary to retain the original composition of phenolic compounds.

A Thorough Study on the Photoisomerization of Ferulic Acid Derivatives

A thorough study on the (E) to (Z) photoisomerization of ferulic acid derivatives (esters, amides of all types, and ketones) was carried out. At the photostationary state, only aliphatic or benzylic tertiary amides reach a nearly complete conversion of (E) isomers into the (Z) ones, whereas for esters, primary and secondary amides or aromatic tertiary amides mixtures of (Z)/(E) ranging from 7 : 93 to 72 : 28 are observed. Ketones show rather limited photoisomerization. However, (Z) ketones may be obtained by the reaction of organometal compounds with an isomerized (Z) Weinreb amide.

Understanding the role played by protic ionic liquids (PILs) and the substituent effect for enhancing the generation of: Z-cinnamic acid derivatives

Photoisomerization of a series of substituted E-cinnamic acids in MeCN in their acid forms and as their corresponding protic ionic liquids (PILs) with light of 300 nm is studied. The nature, strength, number, and position effects of substituents on the photochemical behavior of E-cinnamic derivatives are investigated. The photosensitization of the reaction in the presence of Michler's ketone is also studied at 366 nm and it demonstrates that the triplet-excited state is involved in the reaction. As the presence of n-butylamine needed to form the PILs significantly increases the photoproduct yields in all cases, the role of the PILs is also discussed. Thus, understanding of these fundamental aspects has allowed us to establish an excellent and practical synthetic protocol for successfully synthesizing Z-cinnamic acids. This journal is

Photoisomerization of ionic liquid ammonium cinnamates: One-pot synthesis-isolation of Z-cinnamic acids

Photoisomerization presents the only direct method for contra-thermodynamic E-Z isomerization of olefins. Synthetic applications of this method have been limited by its reversible nature, which leads to a photostationary-state mixture of both isomers. For the first time, a highly efficient one-pot preparation-isolation of solid ionic liquid Z-cinnamic acids by photoisomerization in acetonitrile solution of ionic liquid E-cinnamic acids is described.

Factors affecting toxicity of ferulate towards the cyanobacterium Oscillatoria cf chalybea

The objectives of this study were to determine the effect of ferulate and its analogs, and factors which may affect the toxicity of ferulate to Oscillatoria cf chalybea, the cyanobacterium presumed to cause musty flavor in farm-raised catfish. Rapid bioassays utilizing 96-well and six-well cell culture plates were used to monitor the toxicity of ferulate analogs and potential ferulate stability factors toward O cf chalybea. The additions of low concentrations of the oxidizing compound sodium carbonate peroxyhydrate with ferulate did not help control O cf. chalybea. Of three forms of ferulate tested, trans-ferulate was most toxic towards O cf chalybea. Light enhanced the toxicity of ferulate, indicating that weather conditions and the time of day could influence the success of ferulate applications to fish ponds to control O cf chalybea. Ferulate was less toxic to O cf chalybea in six-well culture plates than in 96-well plates, indicating that higher concentrations of ferulate should be used in field trials, due to possible reduction of ferulate toxicity towards O cf chalybea in large, aquatic environments (ie fish ponds). These studies provided fundamental information on potential ferulate toxicity towards O cf chalybea to be considered before conducting field trials (ferulate applications to fish ponds).

Triterpenes from Prunus africana bark

A chloroformic extract of barks of Prunus africana was found to contain triterpenic acids including derivatives of ursolic and oleanolic acids. Among them 24-O-trans-ferulyl-2α,3α-dihydroxy-urs-12-en-28-oic acid, an original compound, was isolated. Their structure was established by chemical and spectral analysis.