THMG309- Stinky Fruit and Thiols

During our recent Happy Hour, we had an interesting discussion on a spate of recent incidents that brought us around to talking about a skunky compound

This topic was given to us by a Specialist listener on our Monthly Happy Hour. Seems there is a stinky fruit that has been giving the local college some issues, so it gave us the opportunity to talk about the cause.

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Was talking about a few incidents he heard about where people were eating a fruit that smelled so bad that people called the FD to investigate.

The fruit is called Durian Fruit

[Show pic of Durian fruit]

The Durian Fruit is ugly. It’s like a sea urchin. Its big, thorny, and super stinky!

It depends on what side of the fence you sit, there are the people that think it smells a pleasant smell. Some say it smells like gym socks. [kind of like how europeans find our chocolate]

It has been found that the overall odor of durian pulp could be mimicked by only two compounds: fruity smelling ethyl (2S)-2-methylbutanoate and roasted onion-like smelling 1-(ethylsulfanyl)ethane-1-thiol.

Did you say Thiol?!

Why yes I did…

Then lets talk about some thiols and what they are

It’s a sulfur compound. Technically it’s an organosulfur compound. Basically is a sulfur-hydrogen group thats attached to an organic molecule OR an alkyl group.

Now this group can be called a few things, all meaning the same. You could say thiol group, sulfhydryl group or a sulfanyl group. All mean the same. All stinky.

Oddly enough thiols are an analogue of alcohols. The word thiol means a mix of the works alcohol and sulfur in Greek. 

You may be asking yourself, where would I find some of these little bombs? You can find it in Hydrogen Sulfide or mercaptans.

Now taking a look purely at the periodic table, you would find the Sulfur element immediately south of the Oxygen element. Meaning I would assume it has many of the same properties as oxygen (and I think we’re pretty comfortable with oxygen as an element)

But the SH functional group is MUCH different than an OH function. The purely SH group is what they would call a sulfhydryl group in the IUPAC naming system. 

On a side note, the word mercaptan is an ancient word. Its from the latin language. So the older ones were named by saying an alkyl group, then “mercaptan”. Old skool.

You may also find them in the brewing process as a bug in the software. When you add hops to the wort there is one specific one 

One of the unique properties of Thiols is that they don’t form hydrogen bonds, so they have a low boiling point. What does that mean to you as a responder?

[the low BP means high VP therefore its coming to find my nose]

Right, The 2-buten-1- thiol above is one of the components of skunk spray. Mercaptan (aka Methanethiol) is purposely added to bottled gas and natural gas in order to reveal leaks. 

More places are asparagus, cabbage, red grapes, apples and peaches.

Are they acidic or basic?

They tend to be more basic.

Are they flammable?

They can be. The mercaptans are, but not everyone is. 

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