537-33-7 Usage
Description
Sinapyl alcohol, a monolignol, is an organic compound and a primary lignin monomer. It is structurally related to cinnamic acid and is biosynthetized via the phenylpropanoid biochemical pathway. Sinapyl alcohol has been evaluated for its anti-inflammatory and antinociceptive activities and plays a crucial role in the initial stages of lignin biosynthesis. It is also a biosynthetic precursor to various stilbenoids and coumarins.
Uses
Used in Pharmaceutical Applications:
SINAPYL ALCOHOL is used as an active compound for its anti-inflammatory and antinociceptive properties, which have been evaluated for potential therapeutic applications.
Used in Wood Industry:
SINAPYL ALCOHOL is used as a primary lignin monomer for the production of nail polish made of wood, contributing to the development of eco-friendly and sustainable products.
Used in Chemical Industry:
SINAPYL ALCOHOL is used as a precursor in the preparation of lignin, a highly stable biopolymer with various industrial applications, including paper production and as a reinforcing agent in composite materials.
Used in Research and Development:
SINAPYL ALCOHOL is used as a subject of study for understanding its biosynthesis, coupling reactions, and preparation methods, such as selective 1,2-reduction of corresponding cinnamate esters using diisobutylaluminium hydride as a reducing agent. This research contributes to the advancement of knowledge in the field of organic chemistry and plant metabolites.
Biological Activity
Sinapyl alcohol is a monolignol and an aglycone form of syringin that has been found in Populus alba and has anti-inflammatory and antinociceptive activities. It is a precursor in the biosynthesis of lignin. Sinapyl alcohol (50, 100, and 200 μM) reduces LPS-induced production of nitrite, prostaglandin E2 (PGE2), and TNF-α in RAW 264.7 cells. Sinapyl alcohol (20 and 30 mg/kg) inhibits acetic acid-induced writhing and increases the latency to paw licking in the hot plate test in mice.
Preparation and handling
Sinapyl alcohol is supplied as a neat oil. A stock solution may be made by dissolving the sinapyl alcohol in the solvent of choice, which should be purged with an inert gas. Sinapyl alcohol is soluble in organic solvents such as ethanol, DMSO, and dimethyl formamide. The solubility of sinapyl alcohol in these solvents is approximately 30 mg/ml.Further dilutions of the stock solution into aqueous buffers or isotonic saline should be made prior to performing biological experiments. Ensure that the residual amount of organic solvent is insignificant, since organic solvents may have physiological effects at low concentrations. Organic solvent-free aqueous solutions of sinapyl alcohol can be prepared by directly dissolving the neat oil in aqueous buffers. The solubility of sinapyl alcohol in PBS (pH 7.2) is approximately 1 mg/ml. We do not recommend storing the aqueous solution for more than one day.
Check Digit Verification of cas no
The CAS Registry Mumber 537-33-7 includes 6 digits separated into 3 groups by hyphens. The first part of the number,starting from the left, has 3 digits, 5,3 and 7 respectively; the second part has 2 digits, 3 and 3 respectively.
Calculate Digit Verification of CAS Registry Number 537-33:
(5*5)+(4*3)+(3*7)+(2*3)+(1*3)=67
67 % 10 = 7
So 537-33-7 is a valid CAS Registry Number.
InChI:InChI=1/C11H14O4/c1-14-9-6-8(4-3-5-12)7-10(15-2)11(9)13/h3-4,6-7,12-13H,5H2,1-2H3/b4-3+
537-33-7Relevant articles and documents
Non-plasmonic Ni nanoparticles catalyzed visible light selective hydrogenolysis of aryl ethers in lignin under mild conditions
Baeyens, Jan,Li, Peifeng,Ouyang, Yixuan,Sarina, Sarina,Su, Haijia,Xiao, Gang,Zhao, Yilin,Zhu, Huai-Yong
supporting information, p. 7780 - 7789 (2021/10/12)
Light-driven catalysis on catalytically versatile group VIII metals, which has been widely used in thermal catalysis, holds great potential in solar-to-chemical conversion. We report a novel photocatalysis process for the selective hydrogenolysis of aryl ethers in lignin on a heterogeneous catalyst of non-precious Ni nanoparticles supported on ZrO2. Three aryl ether bonds in lignin were successfully cleaved under mild conditions with excellent conversion and good to excellent selectivity under visible light irradiation. We also used solar irradiation to demonstrate a significant reduction in the total energy consumption. The light irradiation excited interband transitions in Ni nanoparticles and the resultant energetic electrons enhanced the activity of reductive cleavage of the aryl ethers. Its application potential was illustrated by the depolymerization of dealkaline lignin to give a total monomer yield of 9.84 wt% with vanillin, guaiacol, and apocynin as the three major products.
COMPOUNDS HAVING HEPATIAL DISEASE EFFECTIVE
-
, (2021/01/29)
The invention discloses a compound with a hepatopathy curative effect, and the compound is a compound shown as a general formula (I), an optical isomer or pharmaceutically acceptable salt thereof, canbe applied to treatment or prevention of hepatopathy, particularly to drugs for treating or preventing fatty liver, liver fibrosis or liver cirrhosis, and has a good application prospect.
Microbial Production of Natural and Unnatural Monolignols with Escherichia coli
Aschenbrenner, Jennifer,Marx, Patrick,Pietruszka, J?rg,Marienhagen, Jan
, p. 949 - 954 (2019/02/26)
Phenylpropanoids and phenylpropanoid-derived plant polyphenols find numerous applications in the food and pharmaceutical industries. In recent years, several microbial platform organisms have been engineered towards producing such compounds. However, for the most part, microbial (poly)phenol production is inspired by nature, so naturally occurring compounds have predominantly been produced to date. Here we have taken advantage of the promiscuity of the enzymes involved in phenylpropanoid synthesis and exploited the versatility of an engineered Escherichia coli strain harboring a synthetic monolignol pathway to convert supplemented natural and unnatural phenylpropenoic acids into their corresponding monolignols. The performed biotransformations showed that this strain is able to catalyze the stepwise reduction of chemically interesting unnatural phenylpropenoic acids such as 3,4,5-trimethoxycinnamic acid, 5-bromoferulic acid, 2-nitroferulic acid, and a “bicyclic” p-coumaric acid derivative, in addition to six naturally occurring phenylpropenoic acids.
