Cooling Ingredients and Their Mechanism of Action

Leffingwell, John C.

doi:10.1201/b15273-66

Cited by 11 publications

(14 citation statements)

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“…To circumvent these drawbacks, industry pursued research and development of chemicals that possess menthol-like cooling activity but with low volatility and without any minty aroma. Using structure-activity relationship approaches, WS in the 1970s generated a library of 1200 synthesised cooling agents 11 37. The agents were labelled using the moniker WS, the manufacturing company’s initials and an identifying number.…”

Section: Chemistry Pharmacology and Toxicology Of Ice-hybrid Flavors ...mentioning

confidence: 99%

“…Some of these coolants were based on the p -menthane structure, the basic monoterpene structure of menthol, with derivatives modified with polar groups directly attached to p -menthane via H-bonding (eg, WS-3, WS-5). Several acyclic compounds that possessed p -menthane-like structural elements were found to retain cooling activity (eg, WS-23) 11. Similar to menthol isomers, different synthetic cooling agent stereoisomers or racemic mixtures varied in their cooling activity, odour and taste 11 12 37…”

Section: Chemistry Pharmacology and Toxicology Of Ice-hybrid Flavors ...mentioning

confidence: 99%

“…First, non-menthol synthetic cooling agents sometimes termed ‘koolada’ (eg, Wilkinson Sword (WS) compounds WS-3, WS-5 and WS-23) have been identified in several mass manufactured e-cigarette products 8 9. In comparison to menthol, some synthetic coolants might elicit enhanced strength or duration of cooling sensations without strong minty flavours 10–12. Second, a novel category of ‘ice’ hybrid-flavoured products have recently emerged, which combine a cooling flavour with a fruit, dessert or other characterising flavour (eg, ‘mango ice’) 13.…”

Section: Introductionmentioning

confidence: 99%

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Ice flavours and non-menthol synthetic cooling agents in e-cigarette products: a review

et al. 2022

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E-cigarettes with cooling flavours have diversified in ways that complicate tobacco control with the emergence of: (1) Ice-hybrid flavours (eg, ‘Raspberry Ice’) that combine cooling and fruity/sweet properties; and (2) Products containing non-menthol synthetic cooling agents (eg, Wilkinson Sword (WS), WS-3, WS-23 (termed ‘koolada’)). This paper reviews the background, chemistry, toxicology, marketing, user perceptions, use prevalence and policy implications of e-cigarette products with ice-hybrid flavours or non-menthol coolants. Scientific literature search supplemented with industry-generated and user-generated information found: (a) The tobacco industry has developed products containing synthetic coolants since 1974, (b) WS-3 and WS-23 are detected in mass-manufactured e-cigarettes (eg, PuffBar); (c) While safe for limited oral ingestion, inhalational toxicology and health effects from daily synthetic coolant exposure are unknown and merit scientific inquiry and attention from regulatory agencies; (d) Ice-hybrid flavours are marketed with themes incorporating fruitiness and/or coolness (eg, snow-covered raspberries); (e) WS-23/WS-3 concentrates also are sold as do-it-yourself additives, (f) Pharmacology research and user-generated and industry-generated information provide a premise to hypothesise that e-cigarette products with ice flavours or non-menthol cooling agents generate pleasant cooling sensations that mask nicotine’s harshness while lacking certain aversive features of menthol-only products, (g) Adolescent and young adult use of e-cigarettes with ice-hybrid or other cooling flavours may be common and cross-sectionally associated with more frequent vaping and nicotine dependence in convenience samples. Evidence gaps in the epidemiology, toxicology, health effects and smoking cessation-promoting potential of using these products exist. E-cigarettes with ice flavours or synthetic coolants merit scientific and regulatory attention.

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Section: Chemistry Pharmacology and Toxicology Of Ice-hybrid Flavors ...mentioning

confidence: 99%

Section: Chemistry Pharmacology and Toxicology Of Ice-hybrid Flavors ...mentioning

confidence: 99%

Section: Introductionmentioning

confidence: 99%

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Ice flavours and non-menthol synthetic cooling agents in e-cigarette products: a review

et al. 2022

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“…It is widely used in many brands of toothpaste, mouthwash, shampoo and, as a food grade flavor ingredient, it can be found in the list of additives to cigarettes and even some food products. The effects of eucalyptol on transient receptor potential (TRP) and cyclic nucleotide-gated channels of olfactory and gustatory receptors provide a basis for its special taste and odor (Chen et al, 2006;Leffingwell, 2009). It has also a broad range of applications in therapeutics and especially used in the folk medicine as a remedy for respiratory problems because of its antiseptic, decongestant and expectorant properties (Juergens et al, 2003).…”

Section: Introductionmentioning

confidence: 99%

Eucalyptol induces hyperexcitability and epileptiform activity in snail neurons by inhibiting potassium channels

Zeraatpisheh

Vatanparast

2015

European Journal of Pharmacology

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“…20 These coolants are considered safe for ingestion by FEMA and are used extensively in consumer products, including breath fresheners, confectionaries and cosmetics. [21][22][23] WS-3 and WS-23 activate the TRPM8 and TRPA1 receptors, creating a cool relaxing sensation 24 while imparting little or no flavour to products that are ingested. WS-23 has been reported in JUUL pods purchased in the European Union 25 but was not found in JUUL pods purchased in the USA.…”

Section: Introductionmentioning

confidence: 99%

Flavour chemicals, synthetic coolants and pulegone in popular mint-flavoured and menthol-flavoured e-cigarettes

et al. 2021

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BackgroundThe Food and Drug Administration (FDA) has recently banned flavours from pod-style electronic cigarettes (e-cigarettes), except for menthol and tobacco. JUUL customers have quickly discovered that flavoured disposable e-cigarettes from other manufacturers, such as Puff, are readily available. Our goal was to compare flavour chemicals, synthetic coolants and pulegone in mint-flavoured/menthol-flavoured e-cigarettes from JUUL and Puff, evaluate the cytotoxicity of the coolants and perform a cancer risk assessment for pulegone, which is present in both JUUL pods and disposable Puff products.MethodsIdentification and quantification of chemicals were performed using gas chromatography/mass spectrometry. Cytotoxicity of the coolants was evaluated with BEAS-2B cells using the MTT 3-(4,5-dimethylthiazol-2-yl)−2,5-diphenyltetrazolium bromide assay. The cancer risk of pulegone was calculated using the margin of exposure (MOE).ResultsMenthol was the dominant flavour chemical (>1 mg/mL) in all products from both manufacturers. Minor flavour chemicals (<1 mg/mL) differed in the JUUL and Puff fluids and may produce flavour accents. The concentrations of WS-3 and WS-23 were higher in Puff than in JUUL. WS-23 was cytotoxic in the MTT assay at concentrations 90 times lower than concentrations in Puff fluids. The risk of cancer (MOE<10 000) was greater for mint than for menthol products and greater for Puff than for JUUL.ConclusionsSwitching from flavoured JUUL to Puff e-cigarettes may expose users to increased harm due to the higher levels of WS-23 and pulegone in Puff products. Cancer risk may be reduced in e-cigarettes by using pure menthol rather than mint oils to produce minty-flavoured e-cigarette products.

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Cooling Ingredients and Their Mechanism of Action

Cited by 11 publications

References 0 publications

Ice flavours and non-menthol synthetic cooling agents in e-cigarette products: a review

Ice flavours and non-menthol synthetic cooling agents in e-cigarette products: a review

Eucalyptol induces hyperexcitability and epileptiform activity in snail neurons by inhibiting potassium channels

Flavour chemicals, synthetic coolants and pulegone in popular mint-flavoured and menthol-flavoured e-cigarettes

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