1135-24-6 Usage
Uses
Used in Food Industry:
Ferulic Acid is used as a food preservative to extend the shelf life and maintain the quality of various food products. It is also used as an intermediate in the production of cinametic acid.
Used in Organic Chemicals:
Ferulic Acid is utilized as a raw material for the synthesis of various organic chemicals.
Used in Biochemical Studies:
Ferulic Acid is applied in biochemical research for its antioxidant and anti-inflammatory properties, as well as its potential in the development of new pharmaceutical compounds.
Used in Pharmaceutical Industry:
Ferulic Acid is used as an anti-neoplastic, choleretic, and anti-oxidant agent. It has been shown to exhibit good permeation capacities through the stratum corneum, which can be attributed to its lipophilic properties.
Used in Cosmetics Industry:
Ferulic Acid is used as an anti-oxidant, anti-inflammatory, and sunscreen enhancer. When incorporated into formulas with ascorbic acid and tocopherol, it can improve their stability and double the photoprotection capacities offered by the formulation.
Physical Properties:
Ferulic Acid appears as a light yellow crystalline powder with a melting point of 170-173°C. It is slightly soluble in cold water, soluble in hot water with poor stability in aqueous solution, easily decomposed when exposed to light, soluble in ethanol and ethyl acetate, slightly soluble in ether, and insoluble in benzene and petroleum ether.
Plant sources
Ferulic acid is a kind of phenolic acid extracted from the resin of ferula asafetida. Ferula asafetida is a kind of Umbelliferae perennial herb with a strong garlic smell and living in sandy areas. It is mainly produced in Xinjiang. During the nascent stage, there are only root leaves. At 5 years, scape emerges. The scape is very strong with its height being up to two meters. At end spring and early summer (flowering stage to early fruit stage), apply slanting cut from the upper position down to the bottom separately, collect oozing milky resin, dry it. Ferula asafetida contains volatile oils, gums and resins with oil containing various kinds of organic acids such as (R)-sec-butyl-1-propenyl disulfide, 1(1-methylthio-propyl) 1-propenyl disulfide, sec-butyl 3-methylthio-allyl-disulfide. Resin containing ferulic acid and its related esters.
Figure 1 is Resina Ferulae
Physical and Chemical Properties
Ferulic acid is an aromatic acid widely being presented in plant kingdom and is the components of suberin. It amount is very small presented in plants in its free state but with its main form in forming bound state with oligosaccharides, polyamines, lipids and polysaccharides. It has many health functions, such as free radical scavenging, anti-thrombotic, anti-inflammatory, anti-tumor, prevention and treatment of hypertension, heart disease, and enhanced sperm activity and so on. Ferulic acid has a low toxicity and is easy for being metabolized by human. It can be used as a food preservative and has a wide range of applications in the field of food and medication.
The above information is edited by the lookchem of Yan Yanyong.
History
Ferulic acid is a derivative of cinnamic acid with molecular formula C10H10O4. In 1886, Hlasiwetz Barth, an Austrian, isolated 3-methoxy-4-hydroxycinnamic acid from the genus Ferula foetida for structure determination. Ferulic acid together with dihydroferulic acid, is a component of lignocelluloses, conferring cell wall rigidity by cross linking lignin and polysaccharides. It is commonly found in seeds of plant such as rice, wheat and oats. Besides, Ferulic Acid exhibited biochemical role in the inhibition of seed germination, inhibition of indole-acetic acid and enzyme, inhibition of decarboxylation activity & other protective effect on micro-organisms and pets.
The syntheis of Ferulic acid was established by Dutt in 1935 when ferulic acid was used as a precursor in the manufacturing of vanillin and malonic acid. There are vast numbers of studies documented on the bio-medical properties of ferulic acid such as antioxidant activity, UV-absorbing capacity & its effect of lignin as precursor in plants metabolic pathway. Ferulic acid, being highly abundant, is indeed difficult to synthesize, Oryza Oil & Fat Chemical has successfully developed an efficient method to extract ferulic acid from rice bran and suitable for applications in the health and beauty arena.
History
Ferulic acid was first isolated from the medicinal plants ferulic in 1866. The biologi_x005fcal activity of ferulic acid was not revealed until 1957 when the pioneering study of
Preziosi P in Italy showed for the first time the efficacy of ferulic acid in regulating
blood lipids and diuretic . In 1979, Lin Mao and others isolated ferulic acid from
the Chinese medicine angelica and reported that ferulic acid had the inhibitory
effect on platelet aggregation . Since then, more and more medicinal efficacy of
ferulic acid has gradually been recognized.
Lipid-Lowering effect
Ferulic acid can competitively inhibit the liver mevalonate-5-pyrophosphate dehydrogenase activity, inhibiting the synthesis of cholesterol in the liver, so as to achieve the purpose of lowering blood pressure.
Antimicrobial effect
Ferulic acid exhibits a broader anti-bacterial spectrum. It has been found that ferulic acid is able to inhibit pathogenic bacteria such as Shigella sonnei, Klebsiella pneumoniae, Enterobacter, Escherichia coli, Citrobacter, Pseudomonas aeruginosa and 11 kinds of microorganisms which causing food corruption.
Food Industry Applications
In addition to its wide application in medicine, ferulic acid has been approved by some countries to be as a food additive. Japan has approved it to be used in food antioxidants while the United States and some European countries have allowed for adopting some kinds of herbs, coffee, beans with relative high amount of ferulic acid for being antioxidant. Ferulic acid, in the food industry, is mainly used for the preparation of natural vanillin, antioxidants, preservatives, cross-linkers and functional promoting agent. The information is edited by Xiaonan from lookchem.
Pharmacological effects
Ferulic acid has various effects of inhibiting platelet aggregation, expectorant, and inhibition of Mycobacterium tuberculosis and so on. Clinically ferulic acid is mainly applied to the adjuvant treatment of various kinds of vascular diseases such as atherosclerosis, coronary heart disease, cerebrovascular, renal disease, pulmonary hypertension, diabetic vascular disease, and vasculitis as well as neutropenia and thrombocytopenia. It can be used for treating migraine and vascular headache. As a leukocyte-enhancement drug, this drug also has enhanced hematopoietic function. Therefore, ferulic acid may also be for the treatment of leukopenia and thrombocytopenia.
Reference: Xu Jingfeng, Yang Ming (editor) Handbook of clinical prescription drugs. Nanjing: Jiangsu Science and Technology Press .2009 on page 561.
Synthetic method
Ferulic acid can be obtained through chemical synthesis and extraction. Laboratory dissolves the vanillin, malonic acid and piperidine in pyridine for reaction of three weeks after which with hydrochloric acid precipitation, you can obtain ferulic acid.
Figure 2 laboratory synthesis roadmap of ferulic acid
Indications
This product is mainly used for the treatment of atherosclerosis, coronary heart
disease and ischemic cerebrovascular disease.
Biotechnological Production
There are three different natural sources for ferulic acid. It could be produced from
low-molecular-weight ferulic conjugates. For example, ferulic acid has been
isolated from the waste material of rice bran oil production by hydrolyzing with
sodium hydroxide or potassium hydroxide at 90–100 C. Ferulic acid with a purity
of 70–90 % was produced within 8 h under atmospheric pressure
Another possibility is a direct extraction of ferulic acid from plant cell walls by
using feruloyl esterases. Various microorganism are able to secrete feruloyl
esterases (e.g. A. niger, Bacillus species and Clostridium thermocellum). The
enzymatic hydrolysis of sugar-beet pulp has been analyzed using a mixture of
carbohydrases from Aspergillus aculeatus with a final ferulic acid concentration of
200 mg.L-1 in the hydrolyzate. Moreover, a purification method to isolate
ferulic acid from sugar-beet pulp after enzymatic hydrolysis using a fixed-bed
adsorption with activated carbon has been developed. With this process, a purity of
50 % has been achieved. Finally, ferulic acid could be produced by cell
culture fermentations. For example, free ferulic acid (up to 50 mg.L-1) and
also conjugated to anthocyanins (up to 150 mg.L-1) has been accumulated in cell
cultures of Ajuga pyramidalis.
Pharmacology
Orally administered ferulic acid completely prevents the formation of skin tumors, reverts the status of phase I and phase II detoxication agents, lipid peroxidaton byproducts and antioxidants to near-normal ranges in 7,12-DMBA-treated mice (Alias et al., 2009). The observation demonstrate that orally administered ferulic acid has potent suppressive effects on cell proliferation during DMBA-induced skin carcinogenesis.
Ferulic acid also has the capacity to prevent UV-induced damage to cells. Ferulic acid is often added as an ingredient to anti-aging supplements. When ferulic acid was incorporated into a formulation of α-tocopherol and/or ascorbic acid, the topical delivery of the vitamins was improved. There was enhanced chemical stability and the photoprotection to solar-simulated irradiation doubled (Lin et al., 2005; Cassano et al., 2009). For example, Murray et al. (2008) applied a stable topical formulation (containing 1% α-tocopherol, 15% L-ascorbic acid, and 0.5% ferulic acid) to normalappearing human skin and a pig skin model. These were then irradiated with solar-simulated UV. The results showed the complex of antioxidants provided substantial UV photoprotection against erythema, sunburnt cells, thymine dimmers, p53 as well as UV-induced cytokine formation including IL-1α, IL-6, IL-8, and IL-10, and TNF-α (Murray et al., 2008).
Clinical Use
At present, there are sodium ferulate tablets and ferulic acid injection used in clinic.
Sodium ferulate tablets are mainly used for the adjuvant therapy of atherosclerosis,
coronary heart disease, cerebrovascular disease, glomerular disease, pulmonary
hypertension, diabetic vascular disease, vasculitis and other vascular disorders.
Ferulic acid can also be used for the treatment of migraine headache and vascular
headache. Ferulic acid injection is mainly used for the treatment of ischemic cardiovascular and cerebrovascular disease. In addition, sodium ferulate combined with
atorvastatin can be used for the treatment of pulmonary hypertension, diabetic
nephropathy and chronic glomerulonephritis in clinic .
Ferulic acid is also used in combination with other drugs to treat other diseases.
Purification Methods
Crystallise ferulic acid from H2O. [Beilstein 10 H 436, 10 IV 1776.]
Check Digit Verification of cas no
The CAS Registry Mumber 1135-24-6 includes 7 digits separated into 3 groups by hyphens. The first part of the number,starting from the left, has 4 digits, 1,1,3 and 5 respectively; the second part has 2 digits, 2 and 4 respectively.
Calculate Digit Verification of CAS Registry Number 1135-24:
(6*1)+(5*1)+(4*3)+(3*5)+(2*2)+(1*4)=46
46 % 10 = 6
So 1135-24-6 is a valid CAS Registry Number.
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)/p-1/b5-3+
1135-24-6Relevant articles and documents
New C,O-Glycosylflavones from the Genus Silene
Olennikov,Kashchenko
, (2020)
Chromatographic separation of extracts from the aerial parts of three Silene species (Caryophyllaceae) isolated 26 flavonoids including the four new C,O-glycosylflavones acacetin-6-C-(2″-O-β-D-glucopyranosyl)-β-D-glucopyranoside-7-O-β-D-glucopyranoside (s
Synthesis of cinnamic acids catalyzed by expansive graphite under ultrasound
Li,Zang,Feng,Li,Li
, p. 653 - 656 (2001)
Knoevenagel condensation of malonic acid with aromatic aldehydes catalysed by expansive graphite results cinnamic acids in 65-98% yields under ultrasound irradiation.
Purification and characterization of a novel aminoacylase from Streptomyces mobaraensis
Koreishi, Mayuko,Asayama, Fumiaki,Imanaka, Hiroyuki,Imamura, Koreyoshi,Kadota, Megumi,Tsuno, Takuo,Nakanishi, Kazuhiro
, p. 1914 - 1922 (2005)
A novel aminoacylase was purified to homogeneity from culture broth of Streptomyces mobaraensis, as evidenced by SDS-polyacrylamide gel electrophoresis (PAGE). The enzyme was a monomer with an approximate molecular mass of 100 kDa. The purified enzyme was inhibited by the presence of 1,10-phenanthroline and activated by the addition of Co2+. It was stable at temperatures of up to 60°C for 1 h at pH 7.2. It showed broad substrate specificity to N-acetylated L-amino acids. It catalyzed the hydrolysis of the amide bonds of various N-acetylated L-amino acids, except for Nε-acetyl-L-lysine and N-acetyl-L-proline. Hydrolysis of N-acetyl-L-methionine and N-acetyl-L-histidine followed Michaelis-Menten kinetics with Km values of 1.3 ± 0.1 mM and 2.7 ± 0.1 mM respectively. The enzyme also catalyzed the deacetylation of 7-aminocephalosporanic acid (7-ACA) and cephalosporin C. Moreover, feruloyl-amino acids and L-lysine derivatives of ferulic acid derivatives were synthesized in an aqueous buffer using the enzyme.
New 3-O-acyl betulinic acids from Strychnos vanprukii Craib
Chien, Nguyen Quyet,Van Hung, Nguyen,Santarsiero, Bernard D.,Mesecar, Andrew D.,Cuong, Nguyen Manh,Soejarto, D. Doel,Pezzuto, John M.,Fong, Harry H. S.,Tan, Ghee T.
, p. 994 - 998 (2004)
Three new betulinic acid derivatives, 3β-O-trans-feruloylbetulinic acid (1), 3β-O-cis-feruloylbetulinic acid (2), and 3β-O-cis- coumaroylbetulinic acid (4), along with two known triterpenes, 3β-O-trans-coumaroylbetulinic acid (3) and ursolic acid (6) were isolated from the leaves and twigs of Strychnos vanprukii Craib. All isolates showed moderate anti-HIV activity with IC50 values ranging from 3 to 7 μg/mL (5 to 15 μM) in an indicator cell line for HIV infectivity. The structures of the new isolates were elucidated by spectroscopic techniques including 1D and 2D NMR spectroscopy. In addition, the structure of 1 was confirmed by X-ray crystallography.
Biotransformation of eugenol to vanillin by a novel strain Bacillus safensis SMS1003
Singh, Archana,Mukhopadhyay, Kunal,Ghosh Sachan, Shashwati
, p. 291 - 303 (2019)
Due to the extensive applications of vanillin as flavored compound and increasing consumers concern for its natural and environment friendly mode of production, present work was focused on the selection of bacterial isolate capable of producing vanillin using eugenol biotransformation. Bacterial strain SMS1003 is evidenced as the potential strain for vanillin production and identified as Bacillus safensis (GeneBank accession no. MG561863) using biochemical tests and molecular phylogenic analysis of its 16S rDNA gene sequence. Molar yield of vanillin reached up to 10.7% (0.055 g/L) at 96 h of biotransformation using growing culture of B. safensis SMS1003 in following culture conditions: eugenol concentration 500 mg/L; temperature 37 °C; initial pH 7.0; inoculum volume 4%; volume of culture media 10%; and shaking speed 180 rpm. Vanillin was detected as the single metabolite with a molar yield of 26% (0.12 g/L) at 96 h using resting cells of B. safensis SMS1003. Product confirmation was based on spectral scan using photodiode array detector, Fourier-transform infrared spectroscopy, high-performance liquid chromatography, and mass spectroscopy.
Identification and quantification of phenolic compounds from the forage legume sainfoin (Onobrychis viciifolia)
Regos, Ionela,Urbanella, Andrea,Treutter, Dieter
, p. 5843 - 5852 (2009)
Phenolic compounds of sainfoin (Onobrychis viciifolia) variety Cotswold Common are assumed to contribute to its nutritive value and bioactive properties. A purified acetone/water extract was separated by Sephadex LH-20 gel chromatography. Sixty-three phen
Novel flavonol glycosides from the aerial parts of lentil (Lens culinaris)
Zuchowski, Jerzy,Pecio, Lukasz,Stochmal, Anna
, p. 18152 - 18178 (2014)
While the phytochemical composition of lentil (Lens culinaris) seeds is well described in scientific literature, there is very little available data about secondary metabolites from lentil leaves and stems. Our research reveals that the aerial parts of lentil are a rich source of flavonoids. Six kaempferol and twelve quercetin glycosides were isolated, their structures were elucidated using NMR spectroscopy and chemical methods. This group includes 16 compounds which have not been previously described in the scientific literature: quercetin 3-O-P-D-glucopyranosyl(1→2)-β-D-galactopyranoside-7-O-β-D-glucuropyranoside (1), kaempferol 3-O-β-D-glucopyranosyl(1→2)-β-D-galactopyranoside-7-O-β-D-glucuropyranoside (3), their derivatives 4-10,12-15,17,18 acylated with caffeic, p-coumaric, ferulic, or 3,4,5-trihydroxycinnamic acid and kaempferol 3-O-{[(6-O-E - p-coumaroyl)-β-D-glucopyranosyl(1→2)]-α-L-rhamnopyranosyl(1-6)}-β-D-galactopyranoside-7-O-α-L-rhamnopyranoside (11). Their DPPH scavenging activity was also evaluated. This is probably the first detailed description of flavonoids from the aerial parts of lentil.
Chemical studies on antioxidant mechanism of curcuminoid: Analysis of radical reaction products from curcumin
Masuda, Toshiya,Hidaka, Kayo,Shinohara, Ayumi,Maekawa, Tomomi,Takeda, Yoshio,Yamaguchi, Hidemasa
, p. 71 - 77 (1999)
In the course of studies on the antioxidant mechanism of curcumin, its radical reaction was investigated. Curcumin was reacted with radical species, which were generated from the pyrolysis of 2,2'-azobis(isobutyronitrile) under an oxygen atmosphere, and the reaction products from curcumin were followed by HPLC. The reaction at 70 °C gave several products, three of which were structurally identified to be vanillin, ferulic acid, and a dimer of curcumin after their isolation. The dimer was a newly identified compound bearing a dihydrofuran moiety, and its chemical structure was elucidated using spectroscopic analyses, especially 2D NMR techniques. A mechanism for the dimer production is proposed and its relation to curcumin's antioxidant activity discussed. The time course and gel permeation chromatography studies of the reaction were also investigated, and the results indicate that the dimer is a radical-terminated product in the initial stage.
New flavonol glycosides from Cardamine komarovii
Lee, Il Kyun,Jeong, Eun-Kyung,Choi, Sang Un,Hong, Jongki,Lee, Kang Ro
, p. 2615 - 2625 (2011)
Seven new kaempferol glycosides (1-7), together with three known kaempferol glycosides (8-10), were isolated from a MeOH extract of Cardamine komarovii Nakai (Cruciferae). The chemical structures of the new compounds (1-7) were determined on the basis of their MS, 1H-NMR, 13C-NMR, COSY, HMBC, NOESY and TOCSY data, and results of hydrolysis.
Lavandoside from Lavandula spica flowers
Kurkin,Lamrini,Klochkov
, p. 169 - 170 (2008)
The new natural compound lavandoside with the structure ferulic acid 4-O-β-D-glucopyranoside was isolated by column chromatography over silica gel and polyamide from the extract of Lavandula spica flowers. The chemical structure of lavandoside was establi
