Wintergreen (methyl salicylate) and decomposition

[O.G.]

So I made an account to ask a relatively scientific question regarding wintergreen flavor. I can't find anything related to this topic (including scholarly articles) and was hoping for some feedback from someone knowledgeable in chemistry.


Methyl Salicylate is a METHYL ESTER. This means that it can (under the right conditions) decompose into methanol and salicylic acid through hydrolysis. Typically, it is used in very low concentrations as a flavoring due to its relatively high inherent toxicity (LD50=0.5g/kg), and is typically not subject to heating when consumed, or added in the presence of an acid/base catalyst.


My question is; wouldn't methyl salicylate (aka wintergreen) be susceptible to hydrolysis under the elevated temperature, not to mention weakly basic conditions found in an e-cigarette, and therefore be TOXIC due to the methanol it would produce. Even if the quantity produced is very small, this would still have toxic effects as methanol is EXTREMELY poisonous.


This process does require water to be present you may argue! but I remind you there is water in the air flowing through your atty, not to mention the water added to liquid by some venders…AND the fact that nicotine is a weak base and may assist in catalyzing this reaction!


Let me know what you think! For now, I’m not touching those wintergreen flavours.


O.G.

 

[IDJoel]

Welcome to the ECF community O.G.!
I tagging @Kurt , who is a chemistry professor for a Pennsylvania university, and active (and well respected) in the vaping community. Hopefully he will have a few minutes to offer his thoughts. As a wintergreen fan I would be interested in hearing all thoughts on this too.

 

[zoiDman]

Welcome to the ECF O.G.

Your question is a little Over my knowledge of Chemistry.

You might want to Copy n' Paste it into this Thread...

Ask The Chemist

 

[Sugar_and_Spice]

So I made an account to ask a relatively scientific question regarding wintergreen flavor. I can't find anything related to this topic (including scholarly articles) and was hoping for some feedback from someone knowledgeable in chemistry.


Methyl Salicylate is a METHYL ESTER. This means that it can (under the right conditions) decompose into methanol and salicylic acid through hydrolysis. Typically, it is used in very low concentrations as a flavoring due to its relatively high inherent toxicity (LD50=0.5g/kg), and is typically not subject to heating when consumed, or added in the presence of an acid/base catalyst.


My question is; wouldn't methyl salicylate (aka wintergreen) be susceptible to hydrolysis under the elevated temperature, not to mention weakly basic conditions found in an e-cigarette, and therefore be TOXIC due to the methanol it would produce. Even if the quantity produced is very small, this would still have toxic effects as methanol is EXTREMELY poisonous.


This process does require water to be present you may argue! but I remind you there is water in the air flowing through your atty, not to mention the water added to liquid by some venders…AND the fact that nicotine is a weak base and may assist in catalyzing this reaction!


Let me know what you think! For now, I’m not touching those wintergreen flavours.


O.G.

Welcome to ecf.
Most of the DIY members know not to use 'oils' in their vaping mixes, so I don't think it is actually used here. Now, if it is synthetically produced I would think that they would produce something without all the 'bad' stuff in it. You don't typically see this type of flavor being used. I personally have not seen a use for the flavor in any of the recipes I've seen. And don't recall anyone ever really mentioning using it.

 

[O.G.]

Hey Sugar and Spice and thank for the welcome!

I just wanted to clarify that natural and synthetic wintergreen both attain their flavor from methyl salicylate. Natural wintergreen oil is primarily methyl salicylate (98%) and contains small quantities of other components that are more hydrophobic (oils such as : a-pinene, myrcene, delta-3-carene, limonene, 3,7-guaiadiene, and delta-cadinene *from wiki*) and would make the natural extract insoluble in PG or VG due to their presence. You are right that the oil would be useless for mixing, but only because of the extra components that come off through distillation when it's made. Methyl salicylate is the molecule that makes flavors have "wintergreen" taste.