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  1. #1

    Default What Have I Created?

    Several weeks ago I made a 50:50 blend of Aldehyde C-12 MNA and indole. At the time the solution was clear, and I checked it today & it is a dark purple, almost gray.

    I read the whole post on Schiff's bases & I realize with indole being a secondary amine that technically it shouldn't be able to create a Schiff base with an aldehyde, but then what type of reaction did these two materials undergo? I'm thinking that indigo may have been released from the indole, which accounts for the purple color? But what reaction could have taken place to bring about this change & is it safe to use?

    I do not notice a difference in the smell of these two materials...it just smells like C-12 MNA and indole. Any ideas? Paul?


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    Darren Alan
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  2. #2
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    Default Re: What Have I Created?

    Yes, you made a schiff base... :-)
    But its probably not complete yet.
    And yes, indole turns dark red purple like that.
    If you want to run the reaction farther, put the bottle out in the sun, and sop out the water that condenses...

  3. #3

    Default Re: What Have I Created?

    Quote Originally Posted by pkiler View Post
    Yes, you made a schiff base... :-)
    But its probably not complete yet.
    And yes, indole turns dark red purple like that.
    If you want to run the reaction farther, put the bottle out in the sun, and sop out the water that condenses...
    Awesome!!! Thanks Paul What should this smell like when it's complete?


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    Darren Alan
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  4. #4
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    Default Re: What Have I Created?

    What will it smell-like?- I have both but I’m not home
    Can I do it with any of the aldehydes?

  5. #5

    Default Re: What Have I Created?

    Quote Originally Posted by Darren Alan View Post
    I read the whole post on Schiff's bases & I realize with indole being a secondary amine that technically it shouldn't be able to create a Schiff base with an aldehyde, but then what type of reaction did these two materials undergo?
    Well, it's technically not a Schiff base, but it is something similar... sort of.

    The reaction can be somewhat more complicated.
    The aldehyde can condense with two indoles, still leaving the secondary amine group intact.

    see diagram here:
    https://www.researchgate.net/figure/...fig3_281171317
    https://www.slideserve.com/garnet/re...sterious-story
    At least in the case of pyrrole, it can form a large porphyrin like molecule, although that wouldn't be the case with indole.

    It's a similar situation for the self-condensation of furfural into a resin. The molecules get joined by a new carbon-carbon bonds.
    Or the condensation of formaldehyde with phenol in the early polymer called bakelite.

    The resulting product in this case is going to have a very high molecular weight. I doubt it would have much of a smell, but I could be totally wrong on that.

    I suspect the two indole groups joined to the aldehyde may be able to undergo further reaction with additional aldehyde. A little bit similar to a porphyrin but you would get more of a polymer beginning to form. (it may undergo tautomerisation allowing this to happen)

    It's common for these type of reaction products to take on deep colors, especially if the solution is acidic.

    There's no reason for any of you to feel overwhelmed or stupid. This type of reaction is very complicated. Not the type of thing perfumers normally have to worry about.

    Aldehydes tend to be pretty reactive, but fortunately in perfumery there are very few things aldehydes will react with (at least irreversibly) under normal conditions (i.e. if the pH is close to a neutral range). All the different types of amines are an exception.

    It does kind of make one wonder if the use of indole is even compatible in a fragrance with aldehydes, long-term. Maybe if they are both very diluted the reaction takes a very long time. I don't have the answer for that. That would take someone with more perfume experience than I, to comment on that.
    Last edited by parker25mv; 21st July 2021 at 05:46 AM.

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    Default Re: What Have I Created?

    Quote Originally Posted by Darren Alan View Post
    Awesome!!! Thanks Paul What should this smell like when it's complete?


    www.darrenalan.com
    I haven't made this before, but Indole schiff bases require 2X Indole molecular weight (mw), to 1X mw of an aldehyde.

    These bases complete their reaction, but smell strongly of Indole. If you have less indole than 2X mw vs. the aldehyde, then it will consume all the indole first, and will still smell, likely, more like the aldehyde.

  7. #7

    Default Re: What Have I Created?

    Quote Originally Posted by pkiler View Post
    I haven't made this before, but Indole schiff bases require 2X Indole molecular weight (mw), to 1X mw of an aldehyde.

    These bases complete their reaction, but smell strongly of Indole. If you have less indole than 2X mw vs. the aldehyde, then it will consume all the indole first, and will still smell, likely, more like the aldehyde.
    I suspect it may not be reacting quite like how a normal schiff base reacts.

    Yes, you are right 2 molecular weights of indole react with 1 aldehyde. But it is also more complex than that.
    I think the first two molecules may be faster to react than the additional indole molecule after that.
    And even after that, it might even be possible for more aldehyde to react, going back towards a 1 to 1 ratio, although that would probably be much slower.

    Or it could maybe be that it does react just like a schiff base, and all the stuff I've been describing might require acidic conditions.

    sorry, brain is tired now, computer is having issues, that's all for now. I'll just leave this at that.

  8. #8
    Basenotes Member WestOzDave's Avatar
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    Default Re: What Have I Created?

    Out of curiosity, what point is there to this reaction within perfumery, apart from the obviousness of not sending out a finished product that may react at a future date within somebodies purchased product? Ive read a little about Schiff's bases having possible effects at treating HIV/Cancer and anti-bacterial properties, do these create interesting aroma profiles or effects...or just give you the knowledge of what NOT to mix together?

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    Default Re: What Have I Created?

    Quote Originally Posted by parker25mv View Post
    I suspect it may not be reacting quite like how a normal schiff base reacts.

    Yes, you are right 2 molecular weights of indole react with 1 aldehyde. But it is also more complex than that.
    I think the first two molecules may be faster to react than the additional indole molecule after that.
    And even after that, it might even be possible for more aldehyde to react, going back towards a 1 to 1 ratio, although that would probably be much slower.

    Or it could maybe be that it does react just like a schiff base, and all the stuff I've been describing might require acidic conditions.

    sorry, brain is tired now, computer is having issues, that's all for now. I'll just leave this at that.
    wow, I continue to be sorry for this. It is better to be silent if you do not have proper information, and only unfounded and unknowledgeable conjecture to offer.

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    Default Re: What Have I Created?

    Quote Originally Posted by WestOzDave View Post
    Out of curiosity, what point is there to this reaction within perfumery, apart from the obviousness of not sending out a finished product that may react at a future date within somebodies purchased product? Ive read a little about Schiff's bases having possible effects at treating HIV/Cancer and anti-bacterial properties, do these create interesting aroma profiles or effects...or just give you the knowledge of what NOT to mix together?
    Schiff bases are used in many industries, including Medicine. Fragrance is mostly a bastard child of the larger class of Schiff chemical reactions.
    The reactions of Schiff bases in Perfumery are strictly about odor profile and molecular size increase, resulting in longevity increase.

    The point to this Schiff base reaction is to create a new molecule that combines attributes of the two original molecules, and is enlarged, and lasts longer.
    Yes, knowing about schiff bases also allows you to avoid reactions that might not be what you wish to occur.

    A recent grand failure to understand Schiff bases was Roja Dove's fragrance Enigma, which included Methyl Anthranilate in the Neroli base, and Vaniillin / Ethyl Vanillin in the basenotes. The Jr. Perfumer at Robertet that composed this for Dove's line was apparently not well educated in Schiff bases, or was unaware of other factors.

    The result was that the perfume was bottled, and was a nice light tan yellow color. After a year from bottling, the perfume had turned medium brown color, and had acquired a schiff base made from these two molecules mentioned, and smelled like the American soft drink Root Beer.

  11. #11

    Default What Have I Created?

    Quote Originally Posted by pkiler View Post
    A recent grand failure to understand Schiff bases was Roja Dove's fragrance Enigma, which included Methyl Anthranilate in the Neroli base, and Vaniillin / Ethyl Vanillin in the basenotes. The Jr. Perfumer at Robertet that composed this for Dove's line was apparently not well educated in Schiff bases, or was unaware of other factors.

    The result was that the perfume was bottled, and was a nice light tan yellow color. After a year from bottling, the perfume had turned medium brown color, and had acquired a schiff base made from these two molecules mentioned, and smelled like the American soft drink Root Beer.
    I never get tired of hearing this story! You would think that a master perfumer like Bob would have been aware of these reactions, but alas we wouldn't have this story...On another note, I'm becoming very intrigued by these Schiff bases, especially after reading Paul's compendium. There are others that I now want to try. Something alchemical about this process intrigues me...taking two different materials & combining them to create something altogether new. It's sort of like my weird fascination with synthesizing peptides from various amino acid chains. I know...I need to get a hobby!


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  12. #12
    Basenotes Member WestOzDave's Avatar
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    Default Re: What Have I Created?

    Quote Originally Posted by pkiler View Post
    Schiff bases are used in many industries, including Medicine. Fragrance is mostly a bastard child of the larger class of Schiff chemical reactions.
    The reactions of Schiff bases in Perfumery are strictly about odor profile and molecular size increase, resulting in longevity increase.

    The point to this Schiff base reaction is to create a new molecule that combines attributes of the two original molecules, and is enlarged, and lasts longer.
    Yes, knowing about schiff bases also allows you to avoid reactions that might not be what you wish to occur.

    A recent grand failure to understand Schiff bases was Roja Dove's fragrance Enigma, which included Methyl Anthranilate in the Neroli base, and Vaniillin / Ethyl Vanillin in the basenotes. The Jr. Perfumer at Robertet that composed this for Dove's line was apparently not well educated in Schiff bases, or was unaware of other factors.

    The result was that the perfume was bottled, and was a nice light tan yellow color. After a year from bottling, the perfume had turned medium brown color, and had acquired a schiff base made from these two molecules mentioned, and smelled like the American soft drink Root Beer.
    Thank you! That explains it simply and humorously all at the same time!

  13. #13

    Default Re: What Have I Created?

    How does one know when your Schiff reaction is complete? I've had this flask out in the sun for 4 days now...the smell has definitely changed. At first I could smell the indole & aldehyde C-12 MNA as seperate components in the blend. But now the sharpness of the aldehyde is gone...it's softened beautifully & the indole is almost imperceptible now. The mixture is taking on a musky/ambergris sort of characteristic that is really quite elegant. I've been removing the water condensation nightly. But I'm just wondering how I will know when it's done?



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    Darren Alan
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  14. #14

  15. #15

    Default Re: What Have I Created?

    At least when it comes to cooking meats, I generally go by when the smoke alarm goes off.

    I learned this technique from Chef Ramsey.

  16. #16

    Default Re: What Have I Created?

    Quote Originally Posted by Bill Roberts View Post
    At least when it comes to cooking meats, I generally go by when the smoke alarm goes off.

    I learned this technique from Chef Ramsey.
    Thanks Bill...you're a big help! Lol


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  17. #17

    Default Re: What Have I Created?


  18. #18

    Default Re: What Have I Created?

    Quote Originally Posted by Darren Alan View Post
    The mixture is taking on a musky/ambergris sort of characteristic that is really quite elegant.
    I could be wrong, but I would suspect what you're smelling is one molecule of aldehyde joined to one molecule of indole (however exactly they happen to be joined).

    That would not constitute the majority of what reaction products are in there.

    If there are two molecules of indole joined together to the aldehyde, that is going to be a very big molecule. I'm not sure it would have much of a smell. If it did it would be an extreme basenote.
    Now it is true that molecules with nitrogen and amine groups in them, like indole, tend to have much stronger smells, so this could maybe constitute an exception to very large molecules not having a smell. The size it is would kind of be right on the edge; there might be a possibility of having some smell but if it were any bigger it definitely would not.

  19. #19

    Default Re: What Have I Created?

    While I have many times seen the 2:1 rule, the mw's which TGSC gives for indole and skatole Schiff Bases correspond with 1:1, and likewise the diagrams are 1:1. FWIW.

    E.g.,

    Picture4.jpg


    Also Lluch sells the above, and the molecular formula is clearly 1:1 for their product: http://www.lluche.com/en/products/na...indole&lang=en

    With Amberlyst catalyst as well as some other protic or Lewis acid catalyzed ways you can get 2:1. It would seem there almost must be one or more ways to selectively or largely get 1:1, given the above.

    Also, if the present experiment started as equimolar indole and C12 MNA, I would think if 50%+ of the C12 MNA remained as would occur if a 2:1 reaction, Darren would need to handle it with a 10 foot pole to prevent his socks from being blown off. As that's not the case, that seems to speak against the reaction having so proceeded.
    Last edited by Bill Roberts; 23rd July 2021 at 09:15 PM.

  20. #20

    Default Re: What Have I Created?

    Apparently you have created an aminal or hemiaminal.

    "The amines used in the fragrance industry are methyl anthranilate and ethyl anthranilate, the former being used more commonly. Note that some materials are sold as Schiff bases of indole, a secondary amine, but these evidently are aminals, a different class."
    https://www.perfumerflavorist.com/fr...c/2896311.html

    https://en.wikipedia.org/wiki/Aminal
    All these moments will be lost in time, like tears in rain.

  21. #21

    Default Re: What Have I Created?

    I have no idea why that author says that.

    What aromamaterial is an aminal?

    Perhaps the "evidently" is a qualifier?

  22. #22

  23. #23

    Default Re: What Have I Created?

    Can you tell me from there or anywhere which aromamaterial that is in commercial use at all is an indole or skatole derived aminal?

    I didn't comb through your links but they did not appear to be heading in that direction, so if you have seen it, that would help.

    None of the indole or skatole "Schiff Bases" on TGSC are aminals. E.g. the indole / hydroxycitronellal is not.

    Edit: the Basenotes link does show Indolene as an aminal. I had not known that. Thank you.

    I hadn't known anyone called Indolene a Schiff's Base, nor that it was so huge a molecule.

    The indole and skatole ones people do call Schiff's Bases aren't aminals, or none that I know of is. But Indolene is. Again, thanks.

    I don't expect Darren has made an aminal, for the above reason.

  24. #24

    Default Re: What Have I Created?

    "I don't expect Darren has made an aminal, for the above reason."

    Which reason was that? Was it because you didn't bother to read the links that I sent you?

    Ah well, as my grandaddy used to say, you can lead a horse to water but you can't make him drink .
    All these moments will be lost in time, like tears in rain.

  25. #25

    Default Re: What Have I Created?

    I don't know what I made, but it smells great!


    Darren Alan Perfumes
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    Darren Alan
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  26. #26

    Default Re: What Have I Created?

    Quote Originally Posted by dcampen View Post
    "I don't expect Darren has made an aminal, for the above reason."

    Which reason was that? Was it because you didn't bother to read the links that I sent you?

    Ah well, as my grandaddy used to say, you can lead a horse to water but you can't make him drink .
    Go read the reason, right after you . yourself.

    You obviously don't know, but your links do not at all demonstrate your fallacious dea that because you read in Perfumer and Flavorist that aminals exist -- did you even know that before then, if not, how shallow your knowledge to be "commenting" as you are -- and found some links that you think all indole / aldehyde condensations are aminals and therefore you've proved Darren's must be. They demonstrate only that at least one case exists in Perfumery. (A ton exist outside perfumery.)

    Go back and read what was provided as plain text and image instead of links dump and see If you can grasp. Perhaps not but if not, that's on you not me. Plain as day complete with picture if you can't grasp numbers or chemical formula, which based on your above it seems you cannot.

    I would go back and edit out my politeness of Post #23 except it stands as testimony against you.

    You seriously failed to grasp what I presented? Well obviously. Way over your head, plainly. And you act like this.

    You seriously think your text or links prove that all or most indole/aldehyde condensation products are aminals despite being shown plainly that that's not a general truth?

    Go back, stop, think, try to comprehend. Try.

    And as for your final and utterly ironic quoted saying, welcome to Ignore, this is not your first effort meriting it either. Reciprocation would be a good thing if you do the same. I have only learned one fact from you ever, which is sure not much and hasn't been worth it, and I expect that due to your displayed traits you have learned even less from me, so there will be zero loss in either direction and only gain of avoiding what is clearly to each rather a negative. But no one can make you do it. It would have advantages for all, however.

    I"m still astonished you couldn't grasp it even complete with picture and example molecular formula that not all aldehyde reactions with indole are 2:1, and lacking that grasp you'd still post like that, but, whatever. It is consistent with your previous, though.

    Despite your [correction, Darren] no longer distinctly perceiving C12 MNA, on the basis of your failure to comprehend material plainly way over your head, you now want to not only insist it must still be 50+% MNA (a necessary consequence of your theory whether you grasp it or not) despite your nose telling you no such thing. Or maybe being so poor that you can't pick up heavy MNA? However I'll take being inadequately able to think things through over being unable to smell as the more likely, and also consistent with past posts.

    Edit: That paragraph was a late night addition and is in error. The actual problem was assuming that Darren could not smell accurately that the MNA had been vastly reduced. Reading from my phone, I misattributed that individual aspect.

    I've encountered some special characters meriting Ignore before, not a lot but some, but you truly win an award with that one and your manner of doing it.

    Utterly ironic, your quote.

    I won't be missing you.
    Last edited by Bill Roberts; 6th August 2021 at 08:20 PM.

  27. #27

    Default Re: What Have I Created?

    Guys. Guys!

    No need to behave like aminals. We're all civilised here...

  28. #28

    Default Re: What Have I Created?

    Quote Originally Posted by Quay Limey View Post
    Guys. Guys!

    No need to behave like aminals. We're all civilised here...
    Hey! As an iminal, I resent that!

  29. #29

    Default Re: What Have I Created?

    Quote Originally Posted by Bill Roberts View Post
    What's saddest of all is you are not even trusting your own nose, both in posting the question of how do you know it's completed (smell it and use it dude, the entire point is organoleptic and perfuming properties, not chemical analysis) and despite your no longer distinctly perceiving C12 MNA, on the basis of your failure to comprehend material plainly way over your head, you now want to not only insist it must still be 50+% MNA (a necessary consequence of your theory whether you grasp it or not) despite your nose telling you no such thing. Or maybe being so poor that you can't pick up heavy MNA? However I'll take being inadequately able to think things through over being unable to smell as the more likely, and also consistent with past posts.

    I've encountered some special characters meriting Ignore before, not a lot but some, but you truly win an award with that one and your manner of doing it.

    Utterly ironic, your quote.

    I won't be missing you.
    Bill,
    I'm not sure what I said to warrant your response or if you have accidentally conflated my comments with the comments of others....at no point was I challenging or questioning the validity of your knowledge on this subject. I feel that my question about how does one know when the Schiff reaction is complete is not only logical, but responsible considering that I made it very clear that this was my first time creating a Schiff base. My question had nothing to do with trusting my nose...I know EXACTLY what I am smelling (or not smelling)...what I don't know is what is going on chemically here & how does one know when this process is complete. I don't think that question was out of line, nor did it warrant such a hostile reply...


    Darren Alan Perfumes
    www.darrenalan.com
    Darren Alan
    www.darrenalan.com

  30. #30

    Default Re: What Have I Created?

    Quote Originally Posted by Quay Limey View Post
    Guys. Guys!

    No need to behave like aminals. We're all civilised here...




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