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3-Hydroxy-4-methoxycinnamic acid

$78

  • Brand : BIOFRON

  • Catalogue Number : BF-H2004

  • Specification : 98%

  • CAS number : 537-73-5

  • Formula : C10H10O4

  • Molecular Weight : 194.18

  • PUBCHEM ID : 736186

  • Volume : 20mg

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Catalogue Number

BF-H2004

Analysis Method

HPLC,NMR,MS

Specification

98%

Storage

2-8°C

Molecular Weight

194.18

Appearance

Colorless crystal

Botanical Source

Cimicifuga foetida

Structure Type

Phenylpropanoids

Category

Standards;Natural Pytochemical;API

SMILES

COC1=C(C=C(C=C1)C=CC(=O)O)O

Synonyms

3'-hydroxy-4'-methoxy cinnamic acid/Hesperitinic acid/trans-Isoferulic acid/2-Propenoic acid, 3-(3-hydroxy-4-methoxyphenyl)-, (2E)-/RARECHEM BK HW 0093/trans-3-hydroxy-4-methoxycinnamic acid/3-Hydroxy-4-MethoxycinnaMic Acid/3-(3-Hydroxy-4-methoxyphenyl)acrylic acid/3-Hydroxy-4-methoxycinnamic/Isoferulic acid/HESPERETINIC ACID/Isoferulate/Isoferulic/Caffeic acid 4-methyl ether/(2E)-3-(3-Hydroxy-4-methoxyphenyl)acrylic acid/3-(3-Hydroxy-4-methoxyphenyl)-2-propenoic acid/Hesperetic acid/(2E)-3-(3-hydroxy-4-methoxyphenyl)prop-2-enoic acid/3-hydroxy-4-methoxy-Cinnamic acid

IUPAC Name

(E)-3-(3-hydroxy-4-methoxyphenyl)prop-2-enoic acid

Density

1.3±0.1 g/cm3

Solubility

Methanol; Ethanol; DMF

Flash Point

167.6±19.4 °C

Boiling Point

410.2±35.0 °C at 760 mmHg

Melting Point

230 °C (dec.)(lit.)

InChl

InChl Key

WGK Germany

RID/ADR

HS Code Reference

2918990000

Personal Projective Equipment

Correct Usage

For Reference Standard and R&D, Not for Human Use Directly.

Meta Tag

provides coniferyl ferulate(CAS#:537-73-5) MSDS, density, melting point, boiling point, structure, formula, molecular weight etc. Articles of coniferyl ferulate are included as well.>> amp version: coniferyl ferulate

PMID

29969636

Abstract

Non-enzymatic glycation and Oxidation of some essential biological macromolecules are paramount in the pathogenesis of various diseases including diabetes and atherosclerosis. Hyperglycemia plays a key role in the pathological process of diabetic complications by progressive accumulation of advanced glycation end products (AGEs) in body tissues. Formation of AGEs as a result of protein glycation is followed by an increased free radical activity that additionally contributes towards the bio-macromolecular damage. The present study aimed to evaluate the free radical scavenging and antiglycation capacity of isoferulic acid (IFA). The free radical scavenging activity of IFA was measured using DPPH, FRAP, and metal chelating assays. IFA showed effective reducing power, free radical scavenging activity and metal chelation activity in concentration dependent manner. The antiglycation activity of IFA was studied using various spectroscopic techniques. The obtained results were validated with free amino, sulfhydryl group, carbonyl content and AGEs formation. Secondary structural alterations were monitored using circular dichroism, morphology of aggregates was analyzed using transmission electron microscopy. Molecular docking reveals the possible binding location of IFA with in the sub-domain IIA of human serum albumin (HSA).

Copyright © 2018 Elsevier B.V. All rights reserved.

Title

Inhibition of advanced glycation end products by isoferulic acid and its free radical scavenging capacity: An in vitro and molecular docking study.

Author

Arfin S1, Siddiqui GA2, Naeem A3, Moin S4

Publish date

2018 Oct 15

PMID

29525672

Abstract

Methylglyoxal (MG) is a reactive precursor to advanced glycation end-products (AGEs), which exert deleterious effects on cells and tissues. MG also causes pancreatic β-cell dysfunction and apoptosis. Isoferulic acid (IFA), a naturally occurring cinnamic acid derivative, is considered to be an antiglycating agent. However, the effect of IFA on MG-induced pancreatic β-cell dysfunction remains unknown. The objective of this study was to determine the protective effect of IFA against MG-induced mitochrondrial dysfunction and apoptosis in INS-1 pancreatic β-cells. The results showed that pretreatment of INS-1 cells with 100 μM IFA for 48 h prevented MG-induced decrease in cell viability and impairment of glucose-stimulated insulin secretion (GSIS). In addition, 100 μM IFA pretreatment also decreased MG-induced generation of reactive oxygen species (ROS) and upregulation of mitochondrial uncoupling protein 2 (Ucp2) mRNA expression. Furthermore, IFA pretreatment reduced MG-induced increase in caspase-3 activity, suggesting a reduction of apoptotic cell death. IFA (50-100 μM) itself markedly increased the activity of glyoxalase 1 (GLO1), a major enzyme for the detoxification of MG. The results showed that 100 μM IFA protected MG-induced loss of GLO1 activity in INS-1 cells. These findings suggest that IFA pretreatment attentuates MG-induced dysfunction and apoptosis in INS-1 pancreatic β-cells through mitochondrial survival pathway and increasing GLO1 activity.

Copyright © 2018 Elsevier Masson SAS. All rights reserved.

KEYWORDS

Glyoxalase-1; Isoferulic acid; Methylglyoxal; Mitochondrial uncoupling protein 2; Pancreatic β-cells

Title

Isoferulic acid attenuates methylglyoxal-induced apoptosis in INS-1 rat pancreatic β-cell through mitochondrial survival pathways and increasing glyoxalase-1 activity.

Author

Meeprom A1, Chan CB2, Sompong W3, Adisakwattana S4.

Publish date

2018 May;

PMID

29451355

Abstract

SCOPE:
Bioavailability strongly determines polyphenol bioactivity, and is strongly influenced by food matrix, enzymatic and microbial degradation, and gastrointestinal absorption. To avoid human trials for pre-screening of polyphenol bioavailability, studies have focused on in vitro model development. Nevertheless, their predictive value for bioavailability can be questioned.

METHOD AND RESULTS:
We used the orange flavonoid hesperidin 2S to validate a model combining digestion in the simulator of the human intestinal microbial ecosystem (SHIME) and Caco-2 cell transport, with a human intervention study. In vitro, hesperidin was resistant to degradation in the stomach and small intestine, but was rapidly deconjugated on reaching the proximal colon. Extensive and colon-region-specific degradation to smaller phenolics was observed. Hydrocaffeic and dihydroisoferulic acid accumulated in proximal, and hydroferulic acid in distal colon. Caco-2 transport was the highest for dihydroisoferulic acid. In humans, plasma and urine hesperetin-glucuronide levels increased significantly, whereas the impact on small phenolics was limited.

CONCLUSIONS:
In the combined in vitro model, smaller phenolics strongly accumulated, whereas in humans, hesperetin conjugates were the main bioavailable compounds. Future in vitro model development should focus on simulating faster polyphenol absorption and elimination of smaller phenolics to improve their predictive value of in vivo polyphenol bioavailability.

© 2018 WILEY-VCH Verlag GmbH & Co. KGaA, Weinheim.

KEYWORDS

Caco-2; SHIME; bioavailability; human; microbiota

Title

A Critical Evaluation of In Vitro Hesperidin 2S Bioavailability in a Model Combining Luminal (Microbial) Digestion and Caco-2 Cell Absorption in Comparison to a Randomized Controlled Human Trial.

Author

Van Rymenant E1, Salden B2, Voorspoels S3, Jacobs G3, Noten B3, Pitart J4, Possemiers S2,4, Smagghe G5, Grootaert C1, Van Camp J1.

Publish date

2018 Apr


Description :

3-Hydroxy-4-methoxycinnamic acid (Isoferulic acid) is a cinnamic acid derivative that has antidiabetic activity. 3-Hydroxy-4-methoxycinnamic acid binds to and activates α1-adrenergic receptors (IC50=1.4 µM) to enhance secretion of β-endorphin (EC50=52.2 nM) and increase glucose use.