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Sinapine

CAT: 0804-HY-N5077-04Size: 10 mgDry Ice: NoHazardous: No
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CAT#:0804-HY-N5077-04Size:10 mg
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Description
Sinapine is an alkaloid isolated from seeds of the cruciferous species. Sinapine exhibits anti-inflammatory, anti-oxidant, anti-tumor, anti-angiogenic and radio-protective effects. Sinapine is also an acetylcholinesterase (AChE) inhibitor and can be used for the research of Alzheimer’s disease, ataxia, myasthenia gravis, and Parkinson’s disease[1][2][3][4].
CAS Number
18696-26-9
UNSPSC
12352005
Hazard Statement
H301, H311, H331
Target
Cholinesterase (ChE) ; P-glycoprotein
Type
Natural Products
Related Pathways
Membrane Transporter/Ion Channel; Neuronal Signaling
Applications
Cancer-programmed cell death
Field of Research
Cancer; Inflammation/Immunology; Neurological Disease
Assay Protocol
https://www.medchemexpress.com/Sinapine.html
Purity
99.96
Solubility
DMSO : 100 mg/mL (ultrasonic)
Smiles
O=C(OCC[N+](C)(C)C)/C=C/C1=CC(OC)=C(O)C(OC)=C1
Molecular Formula
C16H24NO5+
Molecular Weight
310.36
Precautions
H301, H311, H331
References & Citations
[1]Guo Y, et al. Sinapine as an active compound for inhibiting the proliferation of Caco-2 cells via downregulation of P-glycoprotein. Food Chem Toxicol. 2014 May;67:187-92.|[2]Boulghobra D, et, al. Sinapine, but not sinapic acid, counteracts mitochondrial oxidative stress in cardiomyocytes. Redox Biol. 2020 Jul;34:101554.|[3]Li Y, et, al. Sinapine reduces non-alcoholic fatty liver disease in mice by modulating the composition of the gut microbiota. Food Funct. 2019 Jun 19;10 (6) :3637-3649.|[4]Yates K, et, al. Determination of sinapine in rapeseed pomace extract: Its antioxidant and acetylcholinesterase inhibition properties. Food Chem. 2019 Mar 15;276:768-775.
Shipping Conditions
Room Temperature
Storage Conditions
4°C (Powder, sealed storage, away from moisture and light)
Scientific Category
Natural Products
Clinical Information
No Development Reported
Isoform
AChE

Chemical Information

Sinapine

Sinapine is an acylcholine in which the acyl group specified is sinapoyl. It has a role as an antioxidant, a photosynthetic electron-transport chain inhibitor and a plant metabolite. It is functionally related to a trans-sinapic acid.

CAS Number18696-26-9
PubChem CID5280385
IUPAC Name2-[(E)-3-(4-hydroxy-3,5-dimethoxyphenyl)prop-2-enoyl]oxyethyl-trimethylazanium
Molecular FormulaC16H24NO5+
Molecular Weight310.36
XLogP1.8
Topological Polar Surface Area65
Hydrogen Bond Donor Count1
Hydrogen Bond Acceptor Count5
Rotatable Bond Count8
Heavy Atom Count22
Formal Charge1
Complexity363
SMILES
C[N+](C)(C)CCOC(=O)/C=C/C1=CC(=C(C(=C1)OC)O)OC
InChI
InChI=1S/C16H23NO5/c1-17(2,3)8-9-22-15(18)7-6-12-10-13(20-4)16(19)14(11-12)21-5/h6-7,10-11H,8-9H2,1-5H3/p+1
InChIKey
HUJXHFRXWWGYQH-UHFFFAOYSA-O
Chemical Structure
2D Structure
2D structure of Sinapine
CAS: 18696-26-9
CID: 5280385
Formula: C16H24NO5+
MW: 310.36
Interactive 3D Structure
Loading 3D structure...
View on PubChemRaw 3D data
Computed Properties
PropertyValue
Molecular Weight310.36
XLogP31.8
Hydrogen Bond Donor Count1
Hydrogen Bond Acceptor Count5
Rotatable Bond Count8
Exact Mass310.16544787
Monoisotopic Mass310.16544787
Topological Polar Surface Area65 Ų
Heavy Atom Count22
Formal Charge1
Complexity363
Isotope Atom Count0
Defined Atom Stereocenter Count0
Undefined Atom Stereocenter Count0
Defined Bond Stereocenter Count1
Undefined Bond Stereocenter Count0
Covalently-Bonded Unit Count1
Compound Is CanonicalizedYes

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