Trigonelline (Standard)

CAT: 0804-HY-N0414R-01Size: 5 mgDry Ice: NoHazardous: No

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CAT#:0804-HY-N0414R-01Size:5 mg

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Description

Trigonelline (Standard) is the analytical standard of Trigonelline. This product is intended for research and analytical applications. Trigonelline is an alkaloid with potential antidiabetic activity that can be isolated from Trigonella foenum-graecum L or Leonurus artemisia. Trigonelline is a potent Nrf2 inhibitor that blocks Nrf2-dependent proteasome activity, thereby enhancing apoptosis in pancreatic cancer cells. Trigonelline also has anti-HSV-1, antibacterial, and antifungal activity and induces ferroptosis.

CAS Number

535-83-1

Product Name Alternative

Trigenolline (Standard)

UNSPSC

12352005

Hazard Statement

H302, H315, H319, H335

Target

Apoptosis; Bacterial; Endogenous Metabolite; Ferroptosis; Fungal; HIV; Reference Standards

Type

Reference Standards

Related Pathways

Anti-infection; Apoptosis; Metabolic Enzyme/Protease; Others

Applications

Metabolism-protein/nucleotide metabolism

Field of Research

Cancer; Metabolic Disease

Assay Protocol

https://www.medchemexpress.com/trigonelline-standard.html

Purity

99.96

Smiles

C[N+]1=CC(C([O-])=O)=CC=C1

Molecular Formula

C7H7NO2

Molecular Weight

137.14

Precautions

H302, H315, H319, H335

References & Citations

[1]Ilavenil S, et al. Trigonelline protects the cardiocyte from hydrogen peroxide induced apoptosis in H9c2 cells. Asian Pac J Trop Med. 2015 Apr;8 (4) :263-8.|[2]Joanna Folwarczna, et al. Effects of Trigonelline, an Alkaloid Present in Coffee, on Diabetes-Induced Disorders in the Rat Skeletal System. Nutrients. 2016 Mar; 8 (3) : 133.|[3]A Arlt, et al. Inhibition of the Nrf2 transcription factor by the alkaloid trigonelline renders pancreatic cancer cells more susceptible to apoptosis through decreased proteasomal gene expression and proteasome activity. Oncogene. 2013 Oct;32 (40) :4825-35.|[4]Ozçelik B, et al. Cytotoxicity, antiviral and antimicrobial activities of alkaloids, flavonoids, and phenolic acids. Pharm Biol. 2011 Apr;49 (4) :396-402.|[5]Su Y, et al. Ferroptosis, a novel pharmacological mechanism of anti-cancer drugs. Cancer Lett. 2020 Jul 28;483:127-136.

Shipping Conditions

Room Temperature

Storage Conditions

4°C, sealed storage, away from light and moisture

Scientific Category

Reference Standards

Chemical Information

Trigonelline

N-methylnicotinate is an iminium betaine that is the conjugate base of N-methylnicotinic acid, arising from deprotonation of the carboxy group. It has a role as a plant metabolite, a food component and a human urinary metabolite. It is an alkaloid and an iminium betaine. It is functionally related to a nicotinate. It is a conjugate base of a N-methylnicotinic acid.

CAS Number	535-83-1
PubChem CID	5570
IUPAC Name	1-methylpyridin-1-ium-3-carboxylate
Molecular Formula	C7H7NO2
Molecular Weight	137.14
XLogP	1.2
Topological Polar Surface Area	44
Hydrogen Bond Donor Count	0
Hydrogen Bond Acceptor Count	2
Rotatable Bond Count	0
Heavy Atom Count	10
Formal Charge	0
Complexity	130

SMILES

C[N+]1=CC=CC(=C1)C(=O)[O-]

InChI

InChI=1S/C7H7NO2/c1-8-4-2-3-6(5-8)7(9)10/h2-5H,1H3

InChIKey

WWNNZCOKKKDOPX-UHFFFAOYSA-N

Chemical Structure

2D Structure

CAS: 535-83-1

CID: 5570

Formula: C7H7NO2

MW: 137.14

Interactive 3D Structure

Loading 3D structure...

View on PubChem Raw 3D data

Computed Properties

Property	Value
Molecular Weight	137.14
XLogP3	1.2
Hydrogen Bond Donor Count	0
Hydrogen Bond Acceptor Count	2
Rotatable Bond Count	0
Exact Mass	137.047678466
Monoisotopic Mass	137.047678466
Topological Polar Surface Area	44 Å²
Heavy Atom Count	10
Formal Charge	0
Complexity	130
Isotope Atom Count	0
Defined Atom Stereocenter Count	0
Undefined Atom Stereocenter Count	0
Defined Bond Stereocenter Count	0
Undefined Bond Stereocenter Count	0
Covalently-Bonded Unit Count	1
Compound Is Canonicalized	Yes

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Trigonelline (Standard)

Chemical Information

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