Common NameN-methylnicotinate
DescriptionTrigonelline, also known as caffearin or gynesine, belongs to the class of organic compounds known as alkaloids and derivatives. These are naturally occurring chemical compounds that contain mostly basic nitrogen atoms. This group also includes some related compounds with neutral and even weakly acidic properties. Also some synthetic compounds of similar structure are attributed to alkaloids. In addition to carbon, hydrogen and nitrogen, alkaloids may also contain oxygen, sulfur and more rarely other elements such as chlorine, bromine, and phosphorus. It is also found in coffee, where it may help to prevent dental caries by preventing the bacteria Streptococcus mutans from adhering to teeth. Trigonelline is an alkaloid with chemical formula C7H7NO2 and CAS number 535-83-1. Trigonelline is a product of the metabolism of niacin (vitamin B3) which is excreted in the urine. High amounts of trigonelline have been found in arabica coffee, fenugreeks, and common peas. Another foods such as yellow bell peppers, orange bellpeppers and muskmelons also contain trigonelline but in lower concentrations. Trigonelline has also been detected but not quantified in several different foods, such as rices, triticales, alfalfa, cereals and cereal products, and ryes. Trigonelline in the urine is a biomarker for the consumption of coffee, legumes and soy products.
Structure
Molecular FormulaC7H7NO2
Average Mass137.13600
Monoisotopic Mass137.04768
IUPAC Name1-methylpyridin-1-ium-3-carboxylate
Traditional NameTrigonelline
CAS Registry Number535-83-1
SMILESC[n+]1cccc(C(=O)[O-])c1
InChI IdentifierInChI=1S/C7H7NO2/c1-8-4-2-3-6(5-8)7(9)10/h2-5H,1H3
InChI KeyWWNNZCOKKKDOPX-UHFFFAOYSA-N
CHEBI IDCHEBI:18123
HMDB IDHMDB0000875
StateNot Available
Water Solubility3.23e-01 g/l
logP-3.30
logS-2.77
pKa (Strongest Acidic)2.78
pKa (Strongest Basic)Not Available
Hydrogen Acceptor Count2
Hydrogen Donor Count0
Polar Surface Area44.01 Ų
Rotatable Bond Count1
Physiological Charge0
Formal Charge0
Refractivity48.15 m³·mol⁻¹
Polarizability13.40

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