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  1. #1

    Default Can someone with advanced chemistry knowledge help me answer a question?

    I was looking at the fragrance compound keto-isophorone (4-oxoisophorone) and wondering why it is not more reactive.

    I know that quinone readily reacts with amines via addition (responsible for the color change in black hair dyes), but of course that is understandable since that quinone wants to get reduced to a hydroquinone and have aromaticity in the ring.

    But then there's methyl vinyl ketone. That's pretty reactive (and in fact dangerously toxic). That will add to amines and all sorts of things via addition reaction.

    So my question is why doesn't keto-isophorone behave the same?

    I'm assuming it's not very reactive (and certainly not toxic), otherwise it wouldn't be used as a common fragrance compound.

  2. #2

    Default Re: Can someone with advanced chemistry knowledge help me answer a question?

    Or what about cyclohexenone? Is there something about being in the shape of a ring that makes it less reactive?
    We're not even talking about aromaticity here, so what causes that?

    And what about Cinnamaldehyde (in cinnamon EO) ? Why isn't that as reactive or toxic as Acrolein?
    (Something to do with that aromatic ring being electron-donating through the conjugated bond to the oxygen atom? I think that is the case, I just looked it up, explains the inherent yellow coloration of the substance. That still doesn't help answer my first question though.)

  3. #3

    Default Re: Can someone with advanced chemistry knowledge help me answer a question?

    Okay, looking here, the reaction between an enone, at least a cyclic one, and an amine appears to be reversible.

    Doesn't directly answer the question but that's the best I've been able to find so far.

    Also, citation for methyl vinyl ketone automatically reacting with amines, just in case anyone was going to demand it:!divAbstract
    This type doesn't seem to be reversible.

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