[Molecules662]

Hello, I am a food science student and have found two compounds of particular interest in a food matrix. They increase and decrease with approximately the same fold change over time and I am trying to determine a possible reaction mechanism to convert (E,E)-2,4-heptadienal to (E,E)-3,5-heptadien-2-one.

I have tried it and ended up with (E,E)-2,4-heptadien-2-one, but that does not seem like a stable compound and I am not sure I can just move the double bonds to the 3,5 position. How I ended up with 2,4-heptadein-2-one was by a reducing agent converting the aldehyde to a primary aclohol, which was further reduced resulting in the formation of water and a positive charge on the carbon. The hydrogen on the carbon to the left of the positively charged carbon was attacked by the water molecule forming a double bond (Removing the positive charge) and a hydronium ion. The conjugated double bonds were then attacked by the hydronium ion to form a secondary alcohol that could be further oxidized to a ketone. This is probably not sound chemistry, but I was doing my best to explain a possible mechanism. Any help is greatly appreciated!

[magician4]

(E,E)-2,4-heptadien-2-one

I wouldn't even know how to construct it on paper, let alone make it

this definitively is a non-existant substance , with 5 bonds on the 2-C


regards

Ingo

[spirochete]

Hello, I am a food science student and have found two compounds of particular interest in a food matrix. They increase and decrease with approximately the same fold change over time and I am trying to determine a possible reaction mechanism to convert (E,E)-2,4-heptadienal to (E,E)-3,5-heptadien-2-one.

I have tried it and ended up with (E,E)-2,4-heptadien-2-one, but that does not seem like a stable compound and I am not sure I can just move the double bonds to the 3,5 position. How I ended up with 2,4-heptadein-2-one was by a reducing agent converting the aldehyde to a primary aclohol, which was further reduced resulting in the formation of water and a positive charge on the carbon. The hydrogen on the carbon to the left of the positively charged carbon was attacked by the water molecule forming a double bond (Removing the positive charge) and a hydronium ion. The conjugated double bonds were then attacked by the hydronium ion to form a secondary alcohol that could be further oxidized to a ketone. This is probably not sound chemistry, but I was doing my best to explain a possible mechanism. Any help is greatly appreciated!

People are more likely to help you if you give us some pictures and put a little more effort into presenting your question. And also if you don't use non-sensical nomenclature...

[Molecules662]

Hello, I am a food science student and have found two compounds of particular interest in a food matrix. They increase and decrease with approximately the same fold change over time and I am trying to determine a possible reaction mechanism to convert (E,E)-2,4-heptadienal to (E,E)-3,5-heptadien-2-one.

I apologize - I am new here and am not sure how to upload an image. When I click the insert image button, it simply inserts an html code with [img] in it, but I am not sure how to use it. Alternatively, here are links to the compounds I found on the internet:


(E,E)-2,4-heptadienal: http://www.guidechem.com/cas-431/4313-03-5.html
(E,E)-3,5-heptadien-2-one (without the methyl group that appears on this figure!): http://webbook.nist.gov/cgi/cbook.cgi?ID=C16647044&Mask=200

I am simply wondering if it would be possible in something like a food matrix for the (E,E)-2,4-heptadienal to be converted over time to the (E,E)-3,5-heptadien-2-one. Therefore, no laboratory reagents can be added or any non-food grade chemicals. I am wondering if this reaction could potentially chemically happen naturally over time? Possibly through a combination of oxidation and reduction reactions. If this is simply not possible or there is not enough information here, I apologize and please just disregard the question. I figured it was worth a shot to see if anyone might have a plausible hypothesis for how these two compounds could be converted chemically.

I knew the nonsensical nomenclature in the original post was just that. However, I was just trying to explain that I have attempted to work out some theoretical chemistry between these two compounds, but was clearly not having any luck.

Anyways, sorry for confusion or the appearance of slacking in my post content.

[Dan]

I apologize - I am new here and am not sure how to upload an image.

This is covered in the Forum Rules -  see the posting etiquette (3.6 and 3.8).