CAS 132929-88-5

trans-3′-Hydroxycotinine-O-glucuronide

Description:

Trans-3′-Hydroxycotinine-O-glucuronide is a metabolite of nicotine, specifically a glucuronide conjugate of 3′-hydroxycotinine, which is one of the primary metabolites of nicotine in the human body. This compound is characterized by its glucuronidation, a biochemical process that enhances the solubility of lipophilic substances, facilitating their excretion from the body. It typically appears as a white to off-white solid and is soluble in water due to its polar nature. The presence of the glucuronide moiety contributes to its pharmacokinetic properties, influencing its distribution, metabolism, and elimination. Trans-3′-Hydroxycotinine-O-glucuronide is often studied in the context of tobacco use and nicotine metabolism, serving as a biomarker for exposure to nicotine. Its analysis can provide insights into smoking behavior and the effectiveness of smoking cessation therapies. As a chemical entity, it is important in toxicology and pharmacology, particularly in understanding the effects of nicotine and its metabolites on human health.

Formula: C₁₆H₂₀N₂O₈

InChI: InChI=1S/C16H20N2O8/c1-18-8(7-3-2-4-17-6-7)5-9(14(18)22)25-16-12(21)10(19)11(20)13(26-16)15(23)24/h2-4,6,8-13,16,19-21H,5H2,1H3,(H,23,24)/t8-,9+,10-,11-,12+,13-,16+/m0/s1

InChI key: InChIKey=WALNNKZUGHYSCT-MGKNELHOSA-N

SMILES: CN1[C@@H](C[C@@H](O[C@@H]2O[C@H](C(O)=O)[C@@H](O)[C@H](O)[C@H]2O)C1=O)C=3C=CC=NC3

Synonyms:

• (3R,5S)-1-Methyl-2-oxo-5-(3-pyridinyl)-3-pyrrolidinyl β-<span class="text-smallcaps">D</span>-glucopyranosiduronic acid
• (3R,5S)-1-methyl-2-oxo-5-(pyridin-3-yl)pyrrolidin-3-yl beta-D-glucopyranosiduronic acid
• 1-O-(trans-3-Hydroxycotinine)-b-D-glucuronide
• trans-3'-Hydroxycotinine O--D-glucuronide
• trans-3′-Hydroxycotinine-O-glucuronide
• β-<span class="text-smallcaps">D</span>-Glucopyranosiduronic acid, (3R,5S)-1-methyl-2-oxo-5-(3-pyridinyl)-3-pyrrolidinyl
• β-<span class="text-smallcaps">D</span>-Glucopyranosiduronic acid, 1-methyl-2-oxo-5-(3-pyridinyl)-3-pyrrolidinyl, (3R-trans)-
• β-D-Glucopyranosiduronic acid, 1-methyl-2-oxo-5-(3-pyridinyl)-3-pyrrolidinyl, (3R-trans)-
• (3R,5S)-1-Methyl-2-oxo-5-(3-pyridinyl)-3-pyrrolidinyl β-D-glucopyranosiduronic acid
• β-D-Glucopyranosiduronic acid, (3R,5S)-1-methyl-2-oxo-5-(3-pyridinyl)-3-pyrrolidinyl

trans-3′-Hydroxycotinine-O-glucuronide

CAS: 132929-88-5

Formula: C₁₆H₂₀N₂O₈

Color and Shape: Solid

Molecular weight: 368.3386

Ref: IN-DA0011EL

1-O-(trans-3-Hydroxycotinine)-b-D-glucuronide

CAS: 132929-88-5

Ref: 7W-GC5222

trans-3'-Hydroxy Cotinine O-b-D-Glucuronide Sodium Salt

Controlled Product

CAS: 132929-88-5

Formula: C₁₆H₁₉N₂O₈·Na

Color and Shape: Neat

Molecular weight: 390.21

Ref: TR-H414340

trans-3'-Hydroxy Cotinine O-β-D-Glucuronide Ammonium Salt

Controlled Product

CAS: 132929-88-5

Stability Hygroscopic
Applications A Nicotine (N412420) metabolite. Carcinogen.
References Le Marchand, L., et al.: Cancer Res., 58, 4858 (1998), Minna, J., et al.: J. Clin. Invest., 111, 31 (2003), Bierut, L., et al.: Hum. Mol. Genet., 16, 24 (2007), Thorgeirsson, T., et al.: Nature, 452, 638 (2008),

Formula: C₁₆H₂₀N₂O₈·x(NH₃)

Color and Shape: White To Pale Beige Solid

Molecular weight: 368.34 + x(17.03)

Ref: TR-H924575

1-O-(trans-3-Hydroxycotinine)-b-D-glucuronide ammonium salt

CAS: 132929-88-5

The glucuronidation of 1-O-(trans-3-hydroxycotinine)-b-D-glucuronide ammonium salt is mediated by the enzyme UDP-glucuronosyltransferase. This reaction is catalyzed by the transfer of a glucuronic acid residue from UDP-glucuronic acid to a hydroxyl group on the side chain of 1-O-(trans-3-hydroxycotinine)-b-D-glucuronide ammonium salt. The kinetic analysis of human urine samples has shown that this reaction is significant. This metabolite can be detected in urine samples using next generation sequencing and its concentration can be used as an indicator for the consumption of tobacco or nicotine containing products. Epidemiological studies have shown that this metabolite has significant effects on cancer risk. Genotyping and genotype studies have shown that this metabolite is responsible for genetic polymorphisms that are associated with increased cancer risk.

Formula: C₁₆H₂₀N₂O₈•(NH₃)x

Purity: Min. 97%

Color and Shape: White Powder

Molecular weight: 368.34 g/mol

Ref: 3D-MH07437