(-)-Menthol

(-)-menthol is a lipid of Prenol Lipids (PR) class. (-)-menthol is associated with abnormalities such as Wiskott-Aldrich Syndrome. The involved functions are known as Agent, Anabolism, Signal Transduction, Binding (Molecular Function) and Signal Transduction Pathways. (-)-menthol often locates in Membrane, Tissue fiber and Dominant hand. The associated genes with (-)-Menthol are REG1A gene, UGT2B7 gene, HM13 gene and SCN10A gene. The related lipids are Steroids and androsterone glucuronide.

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Introduction

To understand associated biological information of (-)-Menthol, we collected biological information of abnormalities, associated pathways, cellular/molecular locations, biological functions, related genes/proteins, lipids and common seen animal/experimental models with organized paragraphs from literatures.

What diseases are associated with (-)-Menthol?

(-)-Menthol is suspected in and other diseases in descending order of the highest number of associated sentences.

Related references are mostly published in these journals:

Disease Cross reference Weighted score Related literature
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Possible diseases from mapped MeSH terms on references

We collected disease MeSH terms mapped to the references associated with (-)-Menthol

MeSH term MeSH ID Detail
Pain D010146 64 associated lipids
Endophthalmitis D009877 12 associated lipids
Uveitis, Posterior D015866 5 associated lipids
Total 3

PubChem Associated disorders and diseases

What pathways are associated with (-)-Menthol

There are no associated biomedical information in the current reference collection.

PubChem Biomolecular Interactions and Pathways

Link to PubChem Biomolecular Interactions and Pathways

What cellular locations are associated with (-)-Menthol?

Related references are published most in these journals:

Location Cross reference Weighted score Related literatures
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What functions are associated with (-)-Menthol?


Related references are published most in these journals:

Function Cross reference Weighted score Related literatures

What lipids are associated with (-)-Menthol?

Related references are published most in these journals:

Lipid concept Cross reference Weighted score Related literatures
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What genes are associated with (-)-Menthol?

Related references are published most in these journals:


Gene Cross reference Weighted score Related literatures

What common seen animal models are associated with (-)-Menthol?

There are no associated biomedical information in the current reference collection.

NCBI Entrez Crosslinks

All references with (-)-Menthol

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Authors Title Published Journal PubMed Link
Wackowski OA et al. Risk perceptions of menthol cigarettes compared with nonmenthol cigarettes among New Jersey adults. 2010 Nicotine Tob. Res. pmid:20522521
Squier CA et al. Effect of menthol on the penetration of tobacco carcinogens and nicotine across porcine oral mucosa ex vivo. 2010 Nicotine Tob. Res. pmid:20511349
Rose JE and Behm FM Extinguishing the rewarding value of smoke cues: pharmacological and behavioral treatments. 2004 Nicotine Tob. Res. pmid:15203786
Allen B and Unger JB Sociocultural correlates of menthol cigarette smoking among adult African Americans in Los Angeles. 2007 Nicotine Tob. Res. pmid:17454699
Gardiner P and Clark PI Menthol cigarettes: moving toward a broader definition of harm. 2010 Nicotine Tob. Res. pmid:21177372
Healton CG et al. Why we should make menthol cigarettes history. 2010 Nicotine Tob. Res. pmid:21177373
Kreslake JM and Yerger VB Tobacco industry knowledge of the role of menthol in chemosensory perception of tobacco smoke. 2010 Nicotine Tob. Res. pmid:21177374
Castro FG Physiological, psychological, social, and cultural influences on the use of menthol cigarettes among Blacks and Hispanics. 2004 Nicotine Tob. Res. pmid:14982707
Ferris Wayne G and Connolly GN Application, function, and effects of menthol in cigarettes: a survey of tobacco industry documents. 2004 Nicotine Tob. Res. pmid:14982708
Gardiner PS The African Americanization of menthol cigarette use in the United States. 2004 Nicotine Tob. Res. pmid:14982709
Giovino GA et al. Epidemiology of menthol cigarette use. 2004 Nicotine Tob. Res. pmid:14982710
Sutton CD and Robinson RG The marketing of menthol cigarettes in the United States: populations, messages, and channels. 2004 Nicotine Tob. Res. pmid:14982711
Moolchan ET Adolescent menthol smokers: will they be a harder target for cessation? 2004 Nicotine Tob. Res. pmid:14982712
Rostron B Methodology, menthol, and mortality. 2013 Nicotine Tob. Res. pmid:23291639
Jiang CH et al. Gating of the micturition reflex by tonic activation of bladder cold receptors in the cat. 2009 Neurourol. Urodyn. pmid:19260088
Chen Z et al. Stimulation of skin menthol receptors stimulates detrusor activity in conscious rats. 2010 Neurourol. Urodyn. pmid:19618444
Klein AH et al. Eugenol and carvacrol excite first- and second-order trigeminal neurons and enhance their heat-evoked responses. 2014 Neuroscience pmid:24759772
Takashima Y et al. The development of peripheral cold neural circuits based on TRPM8 expression. 2010 Neuroscience pmid:20580783
Dunham JP et al. Transient receptor potential channel A1 and noxious cold responses in rat cutaneous nociceptors. 2010 Neuroscience pmid:19961905
Klein AH et al. Topical hindpaw application of L-menthol decreases responsiveness to heat with biphasic effects on cold sensitivity of rat lumbar dorsal horn neurons. 2012 Neuroscience pmid:22687951
Buonviso N and Chaput M Olfactory experience decreases responsiveness of the olfactory bulb in the adult rat. 2000 Neuroscience pmid:10658611
Frasnelli J et al. Perception of specific trigeminal chemosensory agonists. 2011 Neuroscience pmid:21575683
Mandadi S et al. Locomotor networks are targets of modulation by sensory transient receptor potential vanilloid 1 and transient receptor potential melastatin 8 channels. 2009 Neuroscience pmid:19482068
Galeotti N et al. Menthol: a natural analgesic compound. 2002 Neurosci. Lett. pmid:11897159
Joshi H et al. Spectrophotometric determination of cation concentrations in olfactory mucus. 1987 Neurosci. Lett. pmid:3501083
Zanotto KL et al. Cross-desensitization of responses of rat trigeminal subnucleus caudalis neurons to cinnamaldehyde and menthol. 2008 Neurosci. Lett. pmid:18060696
Reid G and Flonta ML Ion channels activated by cold and menthol in cultured rat dorsal root ganglion neurones. 2002 Neurosci. Lett. pmid:11988352
Wakai J et al. Expression of Fos protein in brainstem after application of l-menthol to the rat nasal mucosa. 2008 Neurosci. Lett. pmid:18343574
Swandulla D et al. Calcium channel current inactivation is selectively modulated by menthol. 1986 Neurosci. Lett. pmid:2425308
Vase L et al. The effects of menthol on cold allodynia and wind-up-like pain in upper limb amputees with different levels of phantom limb pain. 2013 Neurosci. Lett. pmid:23266475
Abe J et al. Ca2+-dependent PKC activation mediates menthol-induced desensitization of transient receptor potential M8. 2006 Apr 10-17 Neurosci. Lett. pmid:16380208
Ott D et al. Prostaglandin D2 modulates calcium signals induced by prostaglandin E2 in neurons of rat dorsal root ganglia. 2015 Neurosci. Lett. pmid:25912777
Bromm B et al. Effects of menthol and cold on histamine-induced itch and skin reactions in man. 1995 Neurosci. Lett. pmid:7624016
Córdova MM et al. Further antinociceptive effects of myricitrin in chemical models of overt nociception in mice. 2011 Neurosci. Lett. pmid:21315136
Smith MP et al. Cold-sensitive, menthol-insensitive neurons in the murine sympathetic nervous system. 2004 Neuroreport pmid:15194861
Jiang CH and Hermanson O Cooling of the urinary bladder activates neurons in the dorsal horn of the spinal cord. 2004 Neuroreport pmid:15076767
Tani M et al. Menthol inhibits the respiratory rhythm in brainstem preparations of the newborn rats. 2010 Neuroreport pmid:20890230
Namer B et al. TRPA1 and TRPM8 activation in humans: effects of cinnamaldehyde and menthol. 2005 Neuroreport pmid:15931068
Okazawa M et al. l-Menthol-induced [Ca2+]i increase and impulses in cultured sensory neurons. 2000 Neuroreport pmid:10923661
Brunzell DH and McIntosh JM Alpha7 nicotinic acetylcholine receptors modulate motivation to self-administer nicotine: implications for smoking and schizophrenia. 2012 Neuropsychopharmacology pmid:22169946
Zuo Y et al. Sex-specific effects of cigarette mentholation on brain nicotine accumulation and smoking behavior. 2015 Neuropsychopharmacology pmid:25267342
García DA et al. Allosteric positive interaction of thymol with the GABAA receptor in primary cultures of mouse cortical neurons. 2006 Neuropharmacology pmid:16185724
Naono-Nakayama R et al. Differential effects of substance P or hemokinin-1 on transient receptor potential channels, TRPV1, TRPA1 and TRPM8, in the rat. 2010 Neuropeptides pmid:19926130
Chuang HH et al. The super-cooling agent icilin reveals a mechanism of coincidence detection by a temperature-sensitive TRP channel. 2004 Neuron pmid:15363396
Colburn RW et al. Attenuated cold sensitivity in TRPM8 null mice. 2007 Neuron pmid:17481392
Bandell M et al. Noxious cold ion channel TRPA1 is activated by pungent compounds and bradykinin. 2004 Neuron pmid:15046718
Mergler S et al. Transient receptor potential channel TRPM8 agonists stimulate calcium influx and neurotensin secretion in neuroendocrine tumor cells. 2007 Neuroendocrinology pmid:17426390
Naziroğlu M and Ozgül C Effects of antagonists and heat on TRPM8 channel currents in dorsal root ganglion neuron activated by nociceptive cold stress and menthol. 2012 Neurochem. Res. pmid:21964764
Petersen M et al. Modulation of calcium-currents by capsaicin in a subpopulation of sensory neurones of guinea pig. 1989 Jan-Feb Naunyn Schmiedebergs Arch. Pharmacol. pmid:2542804
Lehto SG et al. AMG2850, a potent and selective TRPM8 antagonist, is not effective in rat models of inflammatory mechanical hypersensitivity and neuropathic tactile allodynia. 2015 Naunyn Schmiedebergs Arch. Pharmacol. pmid:25662185
Croteau RB et al. (-)-Menthol biosynthesis and molecular genetics. 2005 Naturwissenschaften pmid:16292524
Menini A et al. Quantal-like current fluctuations induced by odorants in olfactory receptor cells. 1995 Nature pmid:7830795
Schmeltz I and Schlotzhauer WS Benzo(a)pyrene, phenols and other products from pyrolysis of the cigarette additive, (d,1)-menthol. 1968 Nature pmid:5662150
Voets T et al. The principle of temperature-dependent gating in cold- and heat-sensitive TRP channels. 2004 Nature pmid:15306801
Reid G and Flonta ML Physiology. Cold current in thermoreceptive neurons. 2001 Nature pmid:11586349
Zuker CS Neurobiology: a cool ion channel. 2002 Nature pmid:11882874
McKemy DD et al. Identification of a cold receptor reveals a general role for TRP channels in thermosensation. 2002 Nature pmid:11882888
Bautista DM et al. The menthol receptor TRPM8 is the principal detector of environmental cold. 2007 Nature pmid:17538622
Chen K and Baran PS Total synthesis of eudesmane terpenes by site-selective C-H oxidations. 2009 Nature pmid:19440196
Gold GH and Lowe G Single odorant molecules? 1995 Nature pmid:7646719
Chessa M et al. Chemical composition and antibacterial activity of the essential oil from Mentha requienii Bentham. 2013 Nat. Prod. Res. pmid:22385272
Kasrati A et al. Essential oil composition and antimicrobial activity of wild and cultivated mint timija (Mentha suaveolens subsp. timija (Briq.) Harley), an endemic and threatened medicinal species in Morocco. 2013 Nat. Prod. Res. pmid:22838406
Miyazawa M et al. Biopreparation of (-)-(1S,3R,4S,6S)-6-hydroxymenthol and (-)-(1S,3R,4S)-1-hydroxymenthol from 1-menthol by Rhizoctonia solani AG-1-IA and IB. 2003 Nat. Prod. Res. pmid:14526907
Esmaeili A et al. Biotransformation of one monoterpene by sporulated surface cultures of Aspergillus niger and Penicillium sp. 2009 Nat. Prod. Res. pmid:19521921
Viana F et al. Specificity of cold thermotransduction is determined by differential ionic channel expression. 2002 Nat. Neurosci. pmid:11836533
Shigetomi E et al. TRPA1 channels regulate astrocyte resting calcium and inhibitory synapse efficacy through GAT-3. 2011 Nat. Neurosci. pmid:22158513
Talavera K et al. Nicotine activates the chemosensory cation channel TRPA1. 2009 Nat. Neurosci. pmid:19749751
Rohács T et al. PI(4,5)P2 regulates the activation and desensitization of TRPM8 channels through the TRP domain. 2005 Nat. Neurosci. pmid:15852009
Montell C A mint of mutations in TRPM8 leads to cool results. 2006 Nat. Neurosci. pmid:16568102
Bandell M et al. High-throughput random mutagenesis screen reveals TRPM8 residues specifically required for activation by menthol. 2006 Nat. Neurosci. pmid:16520735
Parra A et al. Ocular surface wetness is regulated by TRPM8-dependent cold thermoreceptors of the cornea. 2010 Nat. Med. pmid:21076394
Voets T et al. TRPM8 voltage sensor mutants reveal a mechanism for integrating thermal and chemical stimuli. 2007 Nat. Chem. Biol. pmid:17293875
Baranska M and Chruszcz-Lipska K Raman optical activity: a powerful technique to investigate essential oil components. 2010 Nat Prod Commun pmid:20923000
Sharopov FS and Setzer WN Chemical diversity of Ziziphora clinopodioides: composition of the essential oil of Z. clinopodioides from Tajikistan. 2011 Nat Prod Commun pmid:21615034
Chen J et al. Species differences and molecular determinant of TRPA1 cold sensitivity. 2013 Nat Commun pmid:24071625
Tang Z et al. Pirt functions as an endogenous regulator of TRPM8. 2013 Nat Commun pmid:23863968
Narayan AR et al. Enzymatic hydroxylation of an unactivated methylene C-H bond guided by molecular dynamics simulations. 2015 Nat Chem pmid:26201742
Uyar T et al. Electrospinning of functional poly(methyl methacrylate) nanofibers containing cyclodextrin-menthol inclusion complexes. 2009 Nanotechnology pmid:19420480
Kawasaki H et al. [Congenital non-hemolytic and non-conjugating-type hyperbilirubinemia]. 1971 Naika pmid:5572497
Koizumi T and Kamata T [Alternate hyperbilirubinemia]. 1971 Naika pmid:5572498
Siegel M A lost opportunity for public health--the FDA advisory committee report on menthol. 2011 N. Engl. J. Med. pmid:21542736
Benowitz NL and Samet JM The threat of menthol cigarettes to U.S. public health. 2011 N. Engl. J. Med. pmid:21542737
Bell JW Kri i Paste. 1969 N Z Dent J pmid:5254341
Steinmetz MD et al. Transmission and scanning electronmicroscopy study of the action of sage and rosemary essential oils and eucalyptol on Candida albicans. 1988 Mycoses pmid:3287155
Albino AP et al. gammaH2AX: A potential DNA damage response biomarker for assessing toxicological risk of tobacco products. 2009 Mutat. Res. pmid:19591958
Storer RD et al. Revalidation of the in vitro alkaline elution/rat hepatocyte assay for DNA damage: improved criteria for assessment of cytotoxicity and genotoxicity and results for 81 compounds. 1996 Mutat. Res. pmid:8684406
Andersen PH and Jensen NJ Mutagenic investigation of peppermint oil in the Salmonella/mammalian-microsome test. 1984 Mutat. Res. pmid:6387476
Gomes-Carneiro MR et al. Mutagenicity testing (+/-)-camphor, 1,8-cineole, citral, citronellal, (-)-menthol and terpineol with the Salmonella/microsome assay. 1998 Mutat. Res. pmid:9725999
MATZKE H [Interval treatment of angina pectoris with Nitrodurat]. 1962 Munch Med Wochenschr pmid:13933949
BETTECKEN F [NIL NOCERE'. TOXIC SYMPTOMS IN INFANTS AFTER USE OF METHOL-CONTAINING OINTMENTS]. 1964 Munch Med Wochenschr pmid:14255788
Brünger H [Local therapy of contusions using an analgetic and antiexsudative gel]. 1973 Munch Med Wochenschr pmid:4740457
MESSEK H [The effect of different vasoconstrictors on various qualities of the nasal mucosa]. 1962 Monatsschr Ohrenheilkd Laryngorhinol pmid:13935128
Jerković I et al. Volatile organic compounds from Centaurium erythraea Rafn (Croatia) and the antimicrobial potential of its essential oil. 2012 Molecules pmid:22349896
Bassolé IH et al. Composition and antimicrobial activities of Lippia multiflora Moldenke, Mentha x piperita L. and Ocimum basilicum L. essential oils and their major monoterpene alcohols alone and in combination. 2010 Molecules pmid:21060291
Li J et al. Determination of the volatile composition in essential oil of Descurainia sophia (L.) Webb ex Prantl (Flixweed) by gas chromatography/mass spectrometry (GC/MS). 2010 Molecules pmid:20110886
Soković MD et al. Chemical composition of essential oils of Thymus and Mentha species and their antifungal activities. 2009 Molecules pmid:19136911
Soković M et al. Antibacterial effects of the essential oils of commonly consumed medicinal herbs using an in vitro model. 2010 Molecules pmid:21030907
Carballeira JD et al. High throughput screening and QSAR-3D/CoMFA: useful tools to design predictive models of substrate specificity for biocatalysts. 2004 Molecules pmid:18007469
Aulenta F et al. Fragrance release from the surface of branched poly (amide)s. 2005 Molecules pmid:18007278
Cirlini M et al. Phenolic and Volatile Composition of a Dry Spearmint (Mentha spicata L.) Extract. 2016 Molecules pmid:27527127