Menthol glucuronide | CAS#79466-08-3 | metabolite

MedKoo Cat#: 597601 | Name: Menthol glucuronide

Description:

WARNING: This product is for research use only, not for human or veterinary use.

Menthol glucuronide is a metabolite of L-(-)-Menthol, the natural form of Methanol.

Chemical Structure

Menthol glucuronide

CAS#79466-08-3

Theoretical Analysis

MedKoo Cat#: 597601

Name: Menthol glucuronide

CAS#: 79466-08-3

Chemical Formula: C16H28O7

Exact Mass: 332.1835

Molecular Weight: 332.39

Elemental Analysis: C, 57.82; H, 8.49; O, 33.69

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Synonym

Menthol glucuronide; l-Menthol glucuronide; l-Menthyl glucuronide;

IUPAC/Chemical Name

(2R,3S,4S,5S,6S)-3,4,5-trihydroxy-6-(((1R)-2-isopropyl-5-methylcyclohexyl)oxy)tetrahydro-2H-pyran-2-carboxylic acid

InChi Key

CLJGMBYGTHRUNF-NPNHLSTRSA-N

InChi Code

InChI=1S/C16H28O7/c1-7(2)9-5-4-8(3)6-10(9)22-16-13(19)11(17)12(18)14(23-16)15(20)21/h7-14,16-19H,4-6H2,1-3H3,(H,20,21)/t8?,9?,10-,11+,12+,13+,14-,16+/m1/s1

SMILES Code

O[C@@H]([C@H]([C@@H]([C@H](C(O)=O)O1)O)O)[C@H]1O[C@H]2C(C(C)C)CCC(C)C2

Appearance

Solid powder

Purity

>98% (or refer to the Certificate of Analysis)

Shipping Condition

Shipped under ambient temperature as non-hazardous chemical. This product is stable enough for a few weeks during ordinary shipping and time spent in Customs.

Storage Condition

Dry, dark and at 0 - 4 C for short term (days to weeks) or -20 C for long term (months to years).

Solubility

Soluble in DMSO

Shelf Life

>3 years if stored properly

Drug Formulation

This drug may be formulated in DMSO

Stock Solution Storage

0 - 4 C for short term (days to weeks), or -20 C for long term (months).

HS Tariff Code

2934.99.03.00

More Info

Product Data

Product Data

Instruction

View handling instruction

Biological target:

Menthol glucuronide, a metabolite of Menthol (HY-N1369), is a plasma and urine biomarker of acute Menthol inhalation.

In vitro activity:

TBD

In vivo activity:

TBD

Preparing Stock Solutions

The following data is based on the product molecular weight 332.39 Batch specific molecular weights may vary from batch to batch due to the degree of hydration, which will affect the solvent volumes required to prepare stock solutions.

Concentration / Solvent Volume / Mass	1 mg	5 mg	10 mg
1 mM	1.15 mL	5.76 mL	11.51 mL
5 mM	0.23 mL	1.15 mL	2.3 mL
10 mM	0.12 mL	0.58 mL	1.15 mL
50 mM	0.02 mL	0.12 mL	0.23 mL

Formulation protocol:

TBD

In vitro protocol:

TBD

In vivo protocol:

TBD

1: Valente A, Carrillo AE, Tzatzarakis MN, Vakonaki E, Tsatsakis AM, Kenny GP, Koutedakis Y, Jamurtas AZ, Flouris AD. The absorption and metabolism of a single L-menthol oral versus skin administration: Effects on thermogenesis and metabolic rate. Food Chem Toxicol. 2015 Dec;86:262-73. doi: 10.1016/j.fct.2015.09.018. Epub 2015 Sep 30. PubMed PMID: 26429629. 2: Kaffenberger RM, Doyle MJ. Determination of menthol and menthol glucuronide in human urine by gas chromatography using an enzyme-sensitive internal standard and flame ionization detection. J Chromatogr. 1990 Apr 27;527(1):59-66. PubMed PMID: 2365793. 3: Peat J, Frazee C, Kearns G, Garg U. Determination of Menthol in Plasma and Urine by Gas Chromatography/Mass Spectrometry (GC/MS). Methods Mol Biol. 2016;1383:205-11. doi: 10.1007/978-1-4939-3252-8_22. PubMed PMID: 26660189. 4: Nolen HW 3rd, Friend DR. Menthol-beta-D-glucuronide: a potential prodrug for treatment of the irritable bowel syndrome. Pharm Res. 1994 Dec;11(12):1707-11. PubMed PMID: 7899232. 5: Ribeiro A, Caldeira MM, Carvalheiro M, Bastos M, Baptista C, Fagulha A, Barros L, Barosa C, Jones JG. Simple measurement of gluconeogenesis by direct 2H NMR analysis of menthol glucuronide enrichment from 2H2O. Magn Reson Med. 2005 Aug;54(2):429-34. PubMed PMID: 16032678. 6: Benowitz NL, Dains KM, Dempsey D, Havel C, Wilson M, Jacob P 3rd. Urine menthol as a biomarker of mentholated cigarette smoking. Cancer Epidemiol Biomarkers Prev. 2010 Dec;19(12):3013-9. doi: 10.1158/1055-9965.EPI-10-0706. Epub 2010 Oct 20. PubMed PMID: 20962297; PubMed Central PMCID: PMC3005539. 7: Hiki N, Kaminishi M, Hasunuma T, Nakamura M, Nomura S, Yahagi N, Tajiri H, Suzuki H. A phase I study evaluating tolerability, pharmacokinetics, and preliminary efficacy of L-menthol in upper gastrointestinal endoscopy. Clin Pharmacol Ther. 2011 Aug;90(2):221-8. doi: 10.1038/clpt.2011.110. Epub 2011 May 4. PubMed PMID: 21544078. 8: Mendes AC, Caldeira MM, Silva C, Burgess SC, Merritt ME, Gomes F, Barosa C, Delgado TC, Franco F, Monteiro P, Providencia L, Jones JG. Hepatic UDP-glucose 13C isotopomers from [U-13C]glucose: a simple analysis by 13C NMR of urinary menthol glucuronide. Magn Reson Med. 2006 Nov;56(5):1121-5. PubMed PMID: 17036288. 9: Jatlow P, Valentine G, Gueorguieva R, Nadim H, Wu R, O'Malley SS, Sofuoglu M. Plasma Menthol Glucuronide as a Biomarker of Acute Menthol Inhalation. Tob Regul Sci. 2018 Jan;4(1):586-591. doi: 10.18001/TRS.4.1.5. Epub 2018 Jan 1. PubMed PMID: 29479558; PubMed Central PMCID: PMC5822727. 10: Gelal A, Jacob P 3rd, Yu L, Benowitz NL. Disposition kinetics and effects of menthol. Clin Pharmacol Ther. 1999 Aug;66(2):128-35. PubMed PMID: 10460066. 11: Yamaguchi T, Caldwell J, Farmer PB. Metabolic fate of [3H]-l-menthol in the rat. Drug Metab Dispos. 1994 Jul-Aug;22(4):616-24. PubMed PMID: 7956738. 12: Pár A, Horváth T, Beró T, Kádas I, Pakodi F, Jávor T. Inhibition of hepatic drug metabolism by (+)-cyanidanol-3 (Catergen) in chronic alcoholic liver disease. Acta Physiol Hung. 1984;64(3-4):449-54. PubMed PMID: 6152369. 13: Spichiger M, Mühlbauer RC, Brenneisen R. Determination of menthol in plasma and urine of rats and humans by headspace solid phase microextraction and gas chromatography--mass spectrometry. J Chromatogr B Analyt Technol Biomed Life Sci. 2004 Jan 5;799(1):111-7. PubMed PMID: 14659442. 14: Krishnan-Sarin S, Green BG, Kong G, Cavallo DA, Jatlow P, Gueorguieva R, Buta E, O'Malley SS. Studying the interactive effects of menthol and nicotine among youth: An examination using e-cigarettes. Drug Alcohol Depend. 2017 Nov 1;180:193-199. doi: 10.1016/j.drugalcdep.2017.07.044. Epub 2017 Aug 31. PubMed PMID: 28915478; PubMed Central PMCID: PMC5659733. 15: Grigoleit HG, Grigoleit P. Pharmacology and preclinical pharmacokinetics of peppermint oil. Phytomedicine. 2005 Aug;12(8):612-6. Review. PubMed PMID: 16121523. 16: Barosa C, Silva C, Fagulha A, Barros L, Caldeira MM, Carvalheiro M, Jones JG. Sources of hepatic glycogen synthesis following a milk-containing breakfast meal in healthy subjects. Metabolism. 2012 Feb;61(2):250-4. doi: 10.1016/j.metabol.2011.06.022. Epub 2011 Sep 8. PubMed PMID: 21862086. 17: Hsu PC, Lan RS, Brasky TM, Marian C, Cheema AK, Ressom HW, Loffredo CA, Pickworth WB, Shields PG. Menthol Smokers: Metabolomic Profiling and Smoking Behavior. Cancer Epidemiol Biomarkers Prev. 2017 Jan;26(1):51-60. doi: 10.1158/1055-9965.EPI-16-0124. Epub 2016 Sep 14. PubMed PMID: 27628308; PubMed Central PMCID: PMC5386404. 18: Delgado TC, Silva C, Fernandes I, Caldeira M, Bastos M, Baptista C, Carvalheiro M, Geraldes CF, Jones JG. Sources of hepatic glycogen synthesis during an oral glucose tolerance test: Effect of transaldolase exchange on flux estimates. Magn Reson Med. 2009 Nov;62(5):1120-8. doi: 10.1002/mrm.22107. PubMed PMID: 19780152. 19: Cooke CJ, Nanjee MN, Dewey P, Cooper JA, Miller GJ, Miller NE. Plant monoterpenes do not raise plasma high-density-lipoprotein concentrations in humans. Am J Clin Nutr. 1998 Nov;68(5):1042-5. PubMed PMID: 9808220. 20: Horváth T, Pár A, Beró T, Kádas I, Fábián C, Jávor T. Correlation between biochemical tests, parameters of drug elimination and hepatic enzyme induction in chronic liver diseases. Acta Med Hung. 1983;40(4):203-13. PubMed PMID: 6674914.