Sinapyl Alcohol
(Synonyms: 芥子醇) 目录号 : GC49112
A monolignol with anti-inflammatory and antinociceptive activities
Cas No.:537-33-7
Sample solution is provided at 25 µL, 10mM.
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Quality Control & SDS
- View current batch:
- Purity: >98.00%
- COA (Certificate Of Analysis)
- SDS (Safety Data Sheet)
- Datasheet
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.1,2 It is a precursor in the biosynthesis of lignin.1 Sinapyl alcohol (50, 100, and 200 µM) reduces LPS-induced production of nitrite, prostaglandin E2 , and TNF-α in RAW 264.7 cells.2 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.
1.Shigeto, J., Ueda, Y., Sasaki, S., et al.Enzymatic activities for lignin monomer intermediates highlight the biosynthetic pathway of syringyl monomers in Robinia pseudoacaciaJ. Plant Res.130(1)203-210(2017) 2.Choi, J., Shin, K.-M., Park, H.-J., et al.Anti-inflammatory and antinociceptive effects of sinapyl alcohol and its glucoside syringinPlanta Med.70(11)1027-1032(2004)
| Cas No. | 537-33-7 | SDF | |
| 别名 | 芥子醇 | ||
| Canonical SMILES | OC1=C(OC)C=C(C=CCO)C=C1OC | ||
| 分子式 | C11H14O4 | 分子量 | 210.2 |
| 溶解度 | DMF: 30 mg/ml,DMSO: 30 mg/ml,Ethanol: 30 mg/ml,PBS (pH 7.2): 1 mg/ml | 储存条件 | Store at -20°C,protect from light |
| General tips | 请根据产品在不同溶剂中的溶解度选择合适的溶剂配制储备液；一旦配成溶液，请分装保存，避免反复冻融造成的产品失效。 储备液的保存方式和期限：-80°C 储存时，请在 6 个月内使用，-20°C 储存时，请在 1 个月内使用。 为了提高溶解度，请将管子加热至37℃，然后在超声波浴中震荡一段时间。 |
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| Shipping Condition | 评估样品解决方案：配备蓝冰进行发货。所有其他可用尺寸：配备RT，或根据请求配备蓝冰。 | ||
| 制备储备液 | |||
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1 mg | 5 mg | 10 mg |
| 1 mM | 4.7574 mL | 23.7869 mL | 47.5737 mL |
| 5 mM | 0.9515 mL | 4.7574 mL | 9.5147 mL |
| 10 mM | 0.4757 mL | 2.3787 mL | 4.7574 mL |
| 第一步：请输入基本实验信息（考虑到实验过程中的损耗，建议多配一只动物的药量） | ||||||||||
| 给药剂量 | mg/kg |  |
动物平均体重 | g | |
每只动物给药体积 | ul | |
动物数量 | 只 |
| 第二步：请输入动物体内配方组成（配方适用于不溶于水的药物；不同批次药物配方比例不同，请联系GLPBIO为您提供正确的澄清溶液配方） | ||||||||||
| % DMSO % % Tween 80 % saline | ||||||||||
| 计算重置 | ||||||||||
计算结果:
工作液浓度： mg/ml；
DMSO母液配制方法： mg 药物溶于 μL DMSO溶液（母液浓度 mg/mL，
体内配方配制方法：取 μL DMSO母液，加入 μL PEG300，混匀澄清后加入μL Tween 80，混匀澄清后加入 μL saline，混匀澄清。
1. 首先保证母液是澄清的；
2.
一定要按照顺序依次将溶剂加入，进行下一步操作之前必须保证上一步操作得到的是澄清的溶液，可采用涡旋、超声或水浴加热等物理方法助溶。
3. 以上所有助溶剂都可在 GlpBio 网站选购。
Lignin biosynthesis and its integration into metabolism
Curr Opin Biotechnol 2019 Apr;56:230-239.PMID:30913460DOI:10.1016/j.copbio.2019.02.018.
Lignin is a principal structural component of cell walls in higher terrestrial plants. It reinforces the cell walls, facilitates water transport, and acts as a physical barrier to pathogens. Lignin is typically described as being composed of p-hydroxyphenyl (H), guaiacyl (G), and syringyl (S) units that derive from the polymerization of the hydroxycinnamyl alcohols, p-coumaryl, coniferyl, and Sinapyl Alcohol, respectively. However, lignin also derives from various other aromatic monomers. Here, we review the biosynthetic pathway to the lignin monomers, and how flux through the pathway is regulated. Upon perturbation of the phenylpropanoid pathway, pathway intermediates may successfully incorporate into the lignin polymer, thereby affecting its physicochemical properties, or may remain soluble as such or as derivatized molecules that might interfere with physiological processes.
EPR imaging of Sinapyl Alcohol and its application to the study of plant cell wall lignification
Chem Commun (Camb) 2021 Jan 14;57(3):387-390.PMID:33326527DOI:10.1039/d0cc05218c.
In bioimaging, bioorthogonal chemistry is most often used to visualize chemical reporters by fluorescence in their native environment. Herein, we show that TEMPO-based probes can be ligated to monolignol reporters by Diels-Alder chemistry in plant cell walls, paving the way for the study of lignification by EPR spectroscopy and imaging.
Correction: EPR imaging of Sinapyl Alcohol and its application to the study of plant cell wall lignification
Chem Commun (Camb) 2021 Jan 11;57(3):404.PMID:33393953DOI:10.1039/d0cc90541k.
Correction for 'EPR imaging of Sinapyl Alcohol and its application to the study of plant cell wall lignification' by Clémence Simon et al., Chem. Commun., 2021, DOI: .
Anti-inflammatory and antinociceptive effects of Sinapyl Alcohol and its glucoside syringin
Planta Med 2004 Nov;70(11):1027-32.PMID:15549657DOI:10.1055/s-2004-832642.
In the present study, syringin, isolated by activity-guided fractionation of the ethyl acetate (EtOAc) extracts of the stem bark of Magnolia sieboldii, and Sinapyl Alcohol, the hydrolysate of syringin, were evaluated for anti-inflammatory and antinociceptive activities. Sinapyl Alcohol (20, 30 mg/kg/day, p. o.) inhibited increased vascular permeability by acetic acid in mice and reduced acute paw edema by carrageenan in rats more so than syringin. When analgesic activity was measured using the acetic acid-induced writhing test and the hot plate test, Sinapyl Alcohol was much more potent than syringin in a mouse model. In addition, Sinapyl Alcohol more potently inhibited lipopolysaccharide (LPS)-induced nitric oxide (NO), prostaglandin E2 (PGE2), and tumor necrosis factor (TNF)-alpha production by macrophages than syringin. Consistent with these observations, the expression levels of inducible NO synthase (iNOS) and cyclooxygenase (COX)-2 was reduced by Sinapyl Alcohol in a concentration-dependent manner. These results suggest that the anti-inflammatory and antinociceptive effects of syringin after oral administration may be attributed to its in vivo transformation to Sinapyl Alcohol.
BEL1-like Homeodomain Protein BLH6a Is a Negative Regulator of CAl5H2 in Sinapyl Alcohol Monolignol Biosynthesis in Poplar
Front Plant Sci 2021 Jun 25;12:695223.PMID:34249068DOI:10.3389/fpls.2021.695223.
Lignin is one of the major components of xylem cell walls in tree stems. The lignin in the wood of most flowering plants (dicotyledonous angiosperms) is typically polymerized from three monolignol precursors, coniferyl alcohol, Sinapyl Alcohol, and p-coumaroyl alcohol, resulting in guaiacyl (G), syringyl (S), and hydroxyphenyl (H) subunits, respectively. In this study, we focus on the transcriptional regulation of a coniferaldehyde 5-hydroxylase (CAld5H2) gene, which encodes a key enzyme for Sinapyl Alcohol biosynthesis. We carried out a yeast one-hybrid (Y1H) screen to identify candidate upstream transcription factors (TFs) regulating CAld5H2. We obtained 12 upstream TFs as potential regulators of CAld5H2. One of these TF genes, BLH6a, encodes a BEL1-like homeodomain (BLH) protein and negatively regulated the CAld5H2 promoter activity. The direct regulation of CAld5H2 promoter by BLH6a was supported by chromatin immunoprecipitation-quantitative polymerase chain reaction (ChIP-qPCR) and dominant repression of BLH6a in transgenic plants. Luciferase complementation imaging analyses showed extensive protein-protein interactions among these 12 TFs. We propose that BLH6a is a negative regulator of CAld5H2, which acts through combinatorial regulation of multiple TFs for Sinapyl Alcohol (S monolignol) biosynthesis in poplar.