MiMeDB: Showing metabocard for Menthol (MMDBc0033676)

Record Information

Version

1.0

Status

Detected and Quantified

Creation Date

2021-11-19 04:58:31 UTC

Update Date

2024-10-07 00:39:08 UTC

Metabolite ID

MMDBc0033676

Metabolite Identification

Common Name

Menthol

Description

Menthol is an alcohol produced from mint oils or prepared synthetically. Menthol is a covalent organic compound made synthetically or obtained from peppermint or other mint oils. It is a waxy, crystalline substance, clear or white in color, which is solid at room temperature and melts slightly above. The main form of menthol occurring in nature is (-)-menthol, which is assigned the (1R,2S,5R) configuration. Menthol has local anesthetic and counterirritant qualities, and it is widely used to relieve minor throat irritation.

Structure

MOL SDF PDB SMILES InChI

Synonyms

Not Available

Molecular Formula

C₁₀H₂₀O

Average Mass

156.2652

Monoisotopic Mass

156.151415262

IUPAC Name

Not Available

Traditional Name

Not Available

CAS Registry Number

2216-51-5

SMILES

Not Available

InChI Identifier

InChI=1S/C10H20O/c1-7(2)9-5-4-8(3)6-10(9)11/h7-11H,4-6H2,1-3H3

InChI Key

NOOLISFMXDJSKH-UHFFFAOYSA-N

Chemical Taxonomy

Functional Ontology

Not Available

Physical Properties

State

Solid

Predicted Properties

Not Available

Spectra

Not Available

Biological Properties

Cellular Locations

Extracellular
Membrane

Biospecimen Locations

Bladder
Blood
Epidermis
Feces
Neuron
Saliva
Skeletal Muscle
Urine

Tissue Locations

Not Available

Associated OMIM IDs

114500 (Colorectal cancer)
610247 (Eosinophilic esophagitis)

Human Proteins and Enzymes

Protein ID	Protein Name	Protein Type	Uniprot ID	Species

Human Pathways

Pathways

Name	SMPDB/PathBank

Metabolic Reactions

Reactions

Reaction ID	Precursor	Product	Enzyme	Reaction Type	Data Source	Reference

Health Effects and Bioactivity

Health Outcome/Bioactivity	Metabolite Response/Effect	Evidence Type	Host and Biospecimen	Data Source	Reference

Microbial Sources

Superkingdom/Kingdom	Phylum	Total species	Hosts and Body Sites	Microbial Links
Eukaryota/Fungi	Ascomycota	1	Human feces; Human saliva	Unknown

Exposure Sources

Other Exposures

Source Type	Activity	Data Source	Reference
Drugs	Not Available	U.S. Environmental Protection Agency	CompTox
Cosmetics	Not Available	U.S. Environmental Protection Agency	CompTox
Domestics	Not Available	U.S. Environmental Protection Agency	CompTox
Domestics	Not Available	U.S. Environmental Protection Agency	CompTox
Cosmetics	Not Available	U.S. Environmental Protection Agency	CompTox
Water	Not Available	U.S. Environmental Protection Agency	CompTox
Food Additive	Not Available	U.S. Food and Drug Administration	FDA

Host Biospecimen and Location

Host and Biospecimen	Status	Mean	Min	Max	Units	Age	Sex	Health Condition	Data Source	Reference
Human Blood	Detected and Quantified	0.064	0.033	0.159	uM	Adult (>18 years old)	Both	Normal	HMDB	15342616
Human Bladder	Detected but not Quantified					Not Specified	Not Specified	Normal	HMDB	34986597
Human Epidermis	Detected but not Quantified					Not Specified	Not Specified	Normal	HMDB	34986597
Human Neuron	Detected but not Quantified					Not Specified	Not Specified	Normal	HMDB	34986597
Human Skeletal muscle	Detected but not Quantified					Not Specified	Not Specified	Normal	HMDB	34986597
Human Urine	Detected but not Quantified					Adult (>18 years old)	Both	Normal	HMDB	22284503
Human Urine	Detected but not Quantified					Adult (>18 years old)	Both	Normal	HMDB	24023812
Human Saliva	Detected but not Quantified					Adult (>18 years old)	Not Specified	Normal	HMDB	24421258
Human Saliva	Detected but not Quantified					Children (1-13 years old)	Both	Normal	HMDB	24657864
Human Feces	Detected but not Quantified					Adult (>18 years old)	Both	Normal	HMDB	17314143
Human Feces	Detected but not Quantified					Adult (>18 years old)	Both	Normal	HMDB	19167006
Human Feces	Detected but not Quantified					Adult (>18 years old)	Both	Normal	HMDB	23454028
Human Feces	Detected but not Quantified					Adult (>18 years old)	Female	Normal	HMDB	23454028
Human Feces	Detected but not Quantified					Children (1-13 years old)	Both	Normal	HMDB	24130822
Human Feces	Detected but not Quantified					Adult (>18 years old)	Both	Normal	HMDB	24922509
Human Feces	Detected but not Quantified					Adult (>18 years old)	Both	Normal	HMDB	26806034

External Links

HMDB ID

Not Available

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FooDB ID

Not Available

KNApSAcK ID

Not Available

Chemspider ID

Not Available

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

Not Available

PDB ID

Not Available

ChEBI ID

25187

Food Biomarker Ontology

Not Available

References

Synthesis Reference

Not Available

General References

Stich HF, Stich W: Chromosome-damaging activity of saliva of betel nut and tobacco chewers. Cancer Lett. 1982 Mar-Apr;15(3):193-202. doi: 10.1016/0304-3835(82)90118-5. [PubMed:7116324 ]
Eccles R: Menthol and related cooling compounds. J Pharm Pharmacol. 1994 Aug;46(8):618-30. doi: 10.1111/j.2042-7158.1994.tb03871.x. [PubMed:7529306 ]
Prescott J: The generalizability of capsaicin sensitization and desensitization. Physiol Behav. 1999 Jul;66(5):741-9. doi: 10.1016/s0031-9384(99)00012-8. [PubMed:10405101 ]
Valdez JS, Martin DK, Mayersohn M: Sensitive and selective gas chromatographic methods for the quantitation of camphor, menthol and methyl salicylate from human plasma. J Chromatogr B Biomed Sci Appl. 1999 Jun 11;729(1-2):163-71. doi: 10.1016/s0378-4347(99)00161-9. [PubMed:10410939 ]
Gelal A, Jacob P 3rd, Yu L, Benowitz NL: Disposition kinetics and effects of menthol. Clin Pharmacol Ther. 1999 Aug;66(2):128-35. doi: 10.1053/cp.1999.v66.100455001. [PubMed:10460066 ]
Haeseler G, Maue D, Grosskreutz J, Bufler J, Nentwig B, Piepenbrock S, Dengler R, Leuwer M: Voltage-dependent block of neuronal and skeletal muscle sodium channels by thymol and menthol. Eur J Anaesthesiol. 2002 Aug;19(8):571-9. doi: 10.1017/s0265021502000923. [PubMed:12200946 ]
Story GM, Peier AM, Reeve AJ, Eid SR, Mosbacher J, Hricik TR, Earley TJ, Hergarden AC, Andersson DA, Hwang SW, McIntyre P, Jegla T, Bevan S, Patapoutian A: ANKTM1, a TRP-like channel expressed in nociceptive neurons, is activated by cold temperatures. Cell. 2003 Mar 21;112(6):819-29. doi: 10.1016/s0092-8674(03)00158-2. [PubMed:12654248 ]
Haahr AM, Bardow A, Thomsen CE, Jensen SB, Nauntofte B, Bakke M, Adler-Nissen J, Bredie WL: Release of peppermint flavour compounds from chewing gum: effect of oral functions. Physiol Behav. 2004 Sep 15;82(2-3):531-40. doi: 10.1016/j.physbeh.2004.04.061. [PubMed:15276819 ]
Stein RJ, Santos S, Nagatomi J, Hayashi Y, Minnery BS, Xavier M, Patel AS, Nelson JB, Futrell WJ, Yoshimura N, Chancellor MB, De Miguel F: Cool (TRPM8) and hot (TRPV1) receptors in the bladder and male genital tract. J Urol. 2004 Sep;172(3):1175-8. doi: 10.1097/01.ju.0000134880.55119.cf. [PubMed:15311065 ]
Narishetty ST, Panchagnula R: Effect of L-menthol and 1,8-cineole on phase behavior and molecular organization of SC lipids and skin permeation of zidovudine. J Control Release. 2005 Jan 20;102(1):59-70. doi: 10.1016/j.jconrel.2004.09.016. [PubMed:15653134 ]
Rohacs T, Lopes CM, Michailidis I, Logothetis DE: PI(4,5)P2 regulates the activation and desensitization of TRPM8 channels through the TRP domain. Nat Neurosci. 2005 May;8(5):626-34. doi: 10.1038/nn1451. Epub 2005 Apr 24. [PubMed:15852009 ]
Grigoleit HG, Grigoleit P: Pharmacology and preclinical pharmacokinetics of peppermint oil. Phytomedicine. 2005 Aug;12(8):612-6. doi: 10.1016/j.phymed.2004.10.007. [PubMed:16121523 ]
Xu H, Blair NT, Clapham DE: Camphor activates and strongly desensitizes the transient receptor potential vanilloid subtype 1 channel in a vanilloid-independent mechanism. J Neurosci. 2005 Sep 28;25(39):8924-37. doi: 10.1523/JNEUROSCI.2574-05.2005. [PubMed:16192383 ]
Liu Y, Ye X, Feng X, Zhou G, Rong Z, Fang C, Chen H: Menthol facilitates the skin analgesic effect of tetracaine gel. Int J Pharm. 2005 Nov 23;305(1-2):31-6. doi: 10.1016/j.ijpharm.2005.08.005. Epub 2005 Oct 10. [PubMed:16219435 ]
Mukerji G, Yiangou Y, Corcoran SL, Selmer IS, Smith GD, Benham CD, Bountra C, Agarwal SK, Anand P: Cool and menthol receptor TRPM8 in human urinary bladder disorders and clinical correlations. BMC Urol. 2006 Mar 6;6:6. doi: 10.1186/1471-2490-6-6. [PubMed:16519806 ]

Showing metabocard for Menthol (MMDBc0033676)

MOL for #<Metabolite:0x00007fca3000fbc0>

3D MOL for #<Metabolite:0x00007fca3000fbc0>

3D SDF for #<Metabolite:0x00007fca3000fbc0>

3D-SDF for #<Metabolite:0x00007fca3000fbc0>

PDB for #<Metabolite:0x00007fca3000fbc0>

3D PDB for #<Metabolite:0x00007fca3000fbc0>

SMILES for #<Metabolite:0x00007fca3000fbc0>

INCHI for #<Metabolite:0x00007fca3000fbc0>

Structure for #<Metabolite:0x00007fca3000fbc0>

3D Structure for #<Metabolite:0x00007fca3000fbc0>