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Author: Subject: Vanillin...
Nick F
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[*] posted on 15-7-2004 at 14:19
Vanillin...


I guess this goes in bioactive...

Does anyone know the % of vanillin in a typical vanilla pod? I've read that with good vanilla it can crystalise on the surface, although I'm a bit sceptical of this... I can't believe it's pure vanillin. Prove me wrong..?
I thought a fun project this summer would be to try to make some 3,4(,5)-trisubstituted-beta-nitrostyrenes and/or similarly substituted phenylnitroethanes, from OTC stuff. I also want to get tryptophan from albumin, but I know all about that already.

Of course I would not reduce them any further ;).

OK, so you all know what I'm doing, and I know drug preparation isn't discussed here, but a) I'm only asking for a percentage and b) I'm not making drugs, I'm making nitrostyrenes (:D), so I hope this topic will be allowed... And anyway, if I do get round to trying it, it will involve some quite nice practical chemistry.

Thanks for any help!

[Edited on 15-7-2004 by Nick F]

[Edited on 15-7-2004 by Nick F]




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JohnWW
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[*] posted on 9-8-2004 at 13:38


I read somewhere that vanillin, which is the sole constituent of artificial vanilla essence, is not the only active constituent of natural vanilla, although it is the major constituent. Natural vanilla contains other compounds related to or derived from vanillin; and has a slightly different bouquet and taste as the result.

Vanillin is a substituted phenol and benzaldehyde, being 3-methoy-4-hydroxy-benzaldehyde, or 2-methoxy-4-aldehyde-phenol. The other consituents of natural vanilla are probably isomers of this with different placements of the three functional groups on the benzene ring, and possibly an extra methoxy group, or ethoxy in place of methoxy.

John W.
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S.C. Wack
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[*] posted on 9-8-2004 at 13:59
vanillin content


2%.
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thefips
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[*] posted on 25-8-2004 at 03:36


Why donĀ“t you buy vanillin?I have bought 200g to ...well... make some reactions.It is very pure and no problem to get here in Germany.
But it is a difficult way to nitrostyrenes,if you even do not have the possibility to get the starting material in pure form...
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chemoleo
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[*] posted on 26-8-2004 at 18:34


Nick F - you mentioned having details about the isolation of tryptophan from albumin (the protein)
Would you care sharing this with us ? I had a look around, but couldnt find much on it :(
Damn, even espacenet doesnt have decent patents.
If you post this, please create a sep. thread as this is somewhat unrelated to vanillin.




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Nick F
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[*] posted on 27-8-2004 at 04:00


Actually, the procedure I was thinking of used casein, I got mixed up :). And now that I look at it in greater detail, I think I don't want tryptophan that much! But I'll post it anyway....
Although, now that I think about it, I'm pretty sure HalfaPint from the Hive (god rest his soul :() gave details of a method for producing indole from albumin, in which you basically heated the protein to decomposition while distilling off products, and you checked for indole using UV flourescence....




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jarynth
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[*] posted on 17-10-2008 at 23:52
Vanillin from wood


I've been looking into the synthesis of vanillin from lignin. This is how synthetic vanillin was made until the process was deemed polluting.

Lignosulfonates are produced by a chemical wood pulping process: wood chips are digested for one day in sulfurous acid. Does anyone know the necessary concentration of the acid? A winemaking supply store here sells it about 5%. The sulfite process requires a pH between 1.5 and 5.

Calcium lignosulfonates are precipitated with Ca(OH)2 by the Howard process (US1981176). Vanillin is formed by oxidation of the lignoslfonates, and it can be separated from them according to US4277626. I couldn't find quantitative details about the oxidation step either.

This slide reports the higher ratio of polymethoxy substituted rings in lignin from deciduous timber. Would this then by the same procedure give a possible route to (e.g.) methoxyvanillin?
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[*] posted on 18-10-2008 at 01:05


Vanillin is almost always synthetic or semisynthetic these days. Semisynthetic product is produced from other essential oil components (like isoeugenol).

The forum library has the two part THE CHEMISTRY OF ESSENTIAL OILS for free download. Better to make use of it than to start new threads without having done any research on your own first.




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jarynth
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[*] posted on 18-10-2008 at 01:16


Quote:
Originally posted by Sauron
Better to make use of it than to start new threads without having done any research on your own first.

I agree, that's why I posted in the old thread.

EDIT
This gives some insight into the sulfite pulping.

The Chem. of Ess. Oils has something about the coniferin and eugenol processes, nothing about lignin though. The eugenol route was discussed in other threads already; the educt is not particularly affordable compared to wood.

[Edited on 18-10-2008 by jarynth]
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Sauron
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[*] posted on 18-10-2008 at 01:58


True, but you are not the author of this thread, are you? My remark was directed at him.



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jarynth
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[*] posted on 18-10-2008 at 03:49


Quote:
Originally posted by Sauron
True, but you are not the author of this thread, are you? My remark was directed at him.


Isn't there a statute of expiration against flaming thread creators?
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Sauron
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[*] posted on 18-10-2008 at 03:51


Ah, the thread author has probably expired in a geriatric ward by now. Oh well, it's the principle that matters.

[Edited on 19-10-2008 by Sauron]




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[*] posted on 18-10-2008 at 15:50


Which one - the principle of 10 posts a day?

I happen to have 6 JACS articles from '36-41 on the subject of benzaldehydes from woody material. No one is going to like the methods used, but no one said it was really convenient. No doubt that industrial chemistry encyclopedias, patent databases, and the journal literature have much, much more.

Unfortunately the zip uploaded to the board returns a "seek error" on downloading. No such problem with the same zip uploaded elsewhere.

http://mihd.net/96lutjr

EDIT: response to below
Quote:
Originally posted by Sauron
Hey, S.C., best bone up on your arithmetic.


Stats: Averages:
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Member of the Day is Sauron with 11 posts


Would have been 10 (so far today) if you hadn't contributed yet another useless post to this thread.

EDIT 2, again in response to below post:

Quote:
Originally posted by Sauron
Speaking of useless posts, have you stopped beating your wife? (Y/N)


?????? Is that supposed to be an invitation for me to ask WTF so that you can make yet another worthless post?

[Edited on 18-10-2008 by S.C. Wack]
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Sauron
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[*] posted on 18-10-2008 at 16:17


Hey, S.C., best bone up on your arithmetic.

My 2nd anniversary on the forum is fast approaching (12/'06), so my overall thread count works out to more like 5 posts a day. Not 10.

Honi soi qui mal y pens, mon ami.

The thread author opened this thread to ask the essential oil yield from vanilla pods. A datum readily available from the forum library, from books that may well have been uploaded by a guy named S.C.Wack. So I would have thought that you would have approved of encouraging people to at least try to crack a book for an answer once in a while.

That I did not note the date of the thread, mostly because it is essentially invisible to me, is not material.

If you want to call that post whoring, go ahead. I don't think I am more than mildly post-promiscuous.

[Edited on 19-10-2008 by Sauron]




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Sauron
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[*] posted on 18-10-2008 at 18:10


Oh, I see. You are jealous because some silly-ass forum stats function named me Member of the Day?

Well, I was (a) blissfully unaware of the dubious honor, and (b) don't give a damn for it.

Speaking of useless posts, have you stopped beating your wife? (Y/N)

If I post more than you perhaps it is because I have more to say. In any case, I do not take instructions on when, what, or how to post from you, S.C. so kindly don't forget it.




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[*] posted on 18-10-2008 at 21:23


Jarynth, the lignin based process is a useful one if you happen to be operating a lumber mill, paper miss, sulfite type wood pulping plant, which are ebvironmentally monstrous, notorious sources of dimethylmercury etc.

On a bench scale it's a joke.

You'd be better off buying coniferol and going from there or starting from guiacol (thus skipping the hazardous methylation of catechol) to get wherever it is that you want to go.

Of course if you sre just studying vanillin/eugenol production by this process out of idle curiosity, no worries.




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[*] posted on 24-10-2008 at 19:14


Just found this interesting article about armotherapy for elderly people with obvious psychiatric problems:

http://lancashirecare.wordpress.com/2008/05/19/dementia-the-...

Supposedly vanilin can help those people to relax and escape their boring daily routines...

[Edited on by nitro-genes]
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[*] posted on 28-10-2008 at 15:39


Vanillin is commercially available; it's cheap (about 55 USD/kg), comes in high purity, and has many uses, whether it be in baking cookies or as a stain for TLC.

If anyone wants it, I have a trusted supplier for USP grade vanillin (more than adequate for TLC sulfuric stain), just ask!




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[*] posted on 26-4-2011 at 02:43


Did someone have success in creating vanillin from wood? Maybe precipitated calcium lignosulfonates could be oxidized using mild oxidizing agents which oxidize alcohols just to aldehydes and form vanillin?
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