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Details

Stereochemistry ACHIRAL
Molecular Formula C7H8NO2.C7H7O3S
Molecular Weight 309.338
Optical Activity NONE
Defined Stereocenters 0 / 0
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of 3-CARBOXY-1-METHYLPYRIDIN-1-IUM 4-METHYLBENZENESULFONATE

SMILES

C[N+]1=CC(=CC=C1)C(O)=O.CC2=CC=C(C=C2)S([O-])(=O)=O

InChI

InChIKey=WHOCGBIEBJQMMS-UHFFFAOYSA-N
InChI=1S/C7H7NO2.C7H8O3S/c1-8-4-2-3-6(5-8)7(9)10;1-6-2-4-7(5-3-6)11(8,9)10/h2-5H,1H3;2-5H,1H3,(H,8,9,10)

HIDE SMILES / InChI

Molecular Formula C7H8O3S
Molecular Weight 172.202
Charge 0
Count
Stereochemistry ACHIRAL
Additional Stereochemistry No
Defined Stereocenters 0 / 0
E/Z Centers 0
Optical Activity NONE

Molecular Formula C7H7NO2
Molecular Weight 137.136
Charge 0
Count
Stereochemistry ACHIRAL
Additional Stereochemistry No
Defined Stereocenters 0 / 0
E/Z Centers 0
Optical Activity NONE

Description
Curator's Comment: The description was created based on several sources, including https://www.ncbi.nlm.nih.gov/pubmed/19324944 | https://www.ncbi.nlm.nih.gov/pubmed/28816550 | https://www.ncbi.nlm.nih.gov/pubmed/23108405

Trigonelline is a pyridine derivative known to contribute indirectly to the formation of desirable flavor products, including furans, pyrazine, alkyl-pyridines, and pyrroles, during coffee roasting. The amount of trigonelline in arabica is higher than that in robusta green coffee beans, and thus it can be used as a marker compound to distinguish the coffee bean species. During the roasting process of coffee beans, trigonelline changes into N-methylpyridinium and nicotinic acid as its major products, which makes it a useful index of the degree of roasting. The importance of trigonelline in coffee is connected to nutritional aspects. It has been revealed in recent studies that the administration of trigonelline allows diabetic rats to avoid diabetes-related organ damage and live longer, which can make it a potentially strong candidate for industrial application as a pharmacological agent for the treatment of hyperglycemia, hyperlipidemia, and liver/kidney dysfunctions. In addition, the urinary concentrations of trigonelline and its thermal product N-methylpyridinium of coffee drinkers are higher than those of noncoffee drinkers, which indicates that trigonelline and N-methylpyridinium may have potential as dietary biomarkers that could be used as analytical probes to control compliance in human intervention studies on coffee. Trigonelline has been isolated from many plants: fenugreek seeds (Trigonella foenum-graecum, hence the name), garden peas, hemp seed, oats, potatoes, Stachys species, dahlia, Strophanthus species, and Dichapetalum cymosum. In a randomized cross-over trial, the critical effect of Trigonelline on glucose tolerance has been studied during a 2-hour oral glucose tolerance test (OGTT) in 15 overweight men. Results showed that glucose and insulin concentrations significantly reduced 15minutes after Trigonelline consumption compared with placebo.

Approval Year

Targets

Targets

Primary TargetPharmacologyConditionPotency
Conditions

Conditions

ConditionModalityTargetsHighest PhaseProduct
Primary
Unknown

Approved Use

Unknown
Primary
Unknown

Approved Use

Unknown
Sourcing

Sourcing

Vendor/AggregatorIDURL
PubMed

PubMed

TitleDatePubMed
Elevated glycine betaine excretion in diabetes mellitus patients is associated with proximal tubular dysfunction and hyperglycemia.
1999 Feb
Search for natural products related to regeneration of the neuronal network.
2005
Patents

Patents

Sample Use Guides

500 mg trigonelline
Route of Administration: Oral
Panc1 and Colo357 cells were used for activity evaluation. Cells were cultured in RPMI 1640 containing 10% FCS, 1% L-glutamine and 1% sodium pyruvate (all from PAA-Laboratories). Cells were cultured at 37 C, 5% CO2 and 85% humidity. ARE-luciferase assays conducted with Panc1 and Colo357 cells subject to trig (Trigonelline) treatment at various concentrations (0.01–10 mkM) for 16 h revealed a dose-dependent inhibition of ARE-driven luciferase expression by trig.
Substance Class Chemical
Created
by admin
on Sat Dec 16 12:41:54 GMT 2023
Edited
by admin
on Sat Dec 16 12:41:54 GMT 2023
Record UNII
T63236EG5C
Record Status Validated (UNII)
Record Version
  • Download
Name Type Language
3-CARBOXY-1-METHYLPYRIDIN-1-IUM 4-METHYLBENZENESULFONATE
Systematic Name English
N-METHYL-3-CARBOXYPYRIDINIUM TOSYLATE
Common Name English
4-METHYLBENZENESULFONATE,1-METHYLPYRIDIN-1-IUM-3-CARBOXYLIC ACID
Systematic Name English
PYRIDINIUM, 3-CARBOXY-1-METHYL-, SALT WITH 4-METHYLBENZENESULFONIC ACID (1:1)
Common Name English
Code System Code Type Description
ECHA (EC/EINECS)
262-209-5
Created by admin on Sat Dec 16 12:41:54 GMT 2023 , Edited by admin on Sat Dec 16 12:41:54 GMT 2023
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EPA CompTox
DTXSID4069399
Created by admin on Sat Dec 16 12:41:54 GMT 2023 , Edited by admin on Sat Dec 16 12:41:54 GMT 2023
PRIMARY
PUBCHEM
108935
Created by admin on Sat Dec 16 12:41:54 GMT 2023 , Edited by admin on Sat Dec 16 12:41:54 GMT 2023
PRIMARY
FDA UNII
T63236EG5C
Created by admin on Sat Dec 16 12:41:54 GMT 2023 , Edited by admin on Sat Dec 16 12:41:54 GMT 2023
PRIMARY
CAS
60388-20-7
Created by admin on Sat Dec 16 12:41:54 GMT 2023 , Edited by admin on Sat Dec 16 12:41:54 GMT 2023
PRIMARY