Sciencemadness Discussion Board
Not logged in [Login - Register]
Go To Bottom

Printable Version  
Author: Subject: Phenylacetylcarbinol. - how's it made?
Yttrium2
Flammable Solid
****




Posts: 449
Registered: 7-2-2015
Member Is Offline

Mood: Generally snarky?

[*] posted on 24-2-2019 at 03:35
Phenylacetylcarbinol. - how's it made?


So I go to Wikipedia to see how pseudoephedrine is made, it says it's made by l pac. But how is l pac made?

I read yeast ferments dextrose in presence of pyruvate decarboxylase enzyme and then benzaldehyde is added.


Why do I feel like something is left out?


I don't understand the chemistry behind this.


It doesn't seem as clear cut as other chemical reactions, from what I understand, and I know little about chemistry but I can generally follow the pathways off by anecdote and come to some sort of conclusion about whether or not the schema will work.

Can someone go into a bit of detail about what is pyruvate decarboxylase, dextrose, benzaldehyde, how long have these chemicals been in use, and how long has this fermentation technology has been around? I.e. how'd they figure it out?

A bit of a general debriefing would be nice. -- with the neat area 51 esque pictures of the early yeast reactors ECT...



Also, if anything else, can someone explain this
It says it's produced in countries "
where economic and industrial conditions favor its mass production for export.[8]"




[Edited on 2/24/2019 by Yttrium2]
View user's profile View All Posts By User
j_sum1
Administrator
********




Posts: 4678
Registered: 4-10-2014
Location: Oz
Member Is Offline

Mood: Metastable, and that's good enough.

[*] posted on 24-2-2019 at 03:41


How is this not a spoonfeeding request for ephedrine precursors?

This better be good or I am sending it to Detritus.
View user's profile View All Posts By User
Metacelsus
International Hazard
*****




Posts: 2268
Registered: 26-12-2012
Location: Cambridge, UK
Member Is Offline

Mood: Double, double, toil and trouble

[*] posted on 24-2-2019 at 05:04


I don't think this is necessarily spoonfeeding; Yttrium2 is just asking a biochemistry question.

Basically, pyruvate decarboxylase normally converts pyruvate into acetaldehyde + CO2 using a thiamine cofactor. However, in the presence of benzaldehyde, the thiamine-bound intermediate can react with benzaldehyde to form L-PAC instead of releasing acetaldehyde.

edit: see this paper for more details

[Edited on 2019-2-24 by Metacelsus]

Attachment: 1-s2.0-S0922338X97819009-main.pdf (750kB)
This file has been downloaded 79 times





As below, so above.
View user's profile View All Posts By User
Tsjerk
International Hazard
*****




Posts: 1612
Registered: 20-4-2005
Location: Netherlands
Member Is Offline

Mood: Mood

[*] posted on 24-2-2019 at 07:49


Quote: Originally posted by Metacelsus  

Basically, pyruvate decarboxylase normally converts pyruvate into acetaldehyde + CO2 using a thiamine cofactor. However, in the presence of benzaldehyde, the thiamine-bound intermediate can react with benzaldehyde to form L-PAC instead of releasing acetaldehyde.


As chemical synthesis of this two stereo-isomer center containing molecule probably is not economic.

[Edited on 24-2-2019 by Tsjerk]
View user's profile View All Posts By User
Waffles SS
Fighter
*****




Posts: 917
Registered: 7-12-2009
Member Is Offline


[*] posted on 24-2-2019 at 08:18


All possible way for synthesis (RS)Phenylacetylcarbinol

Attachment: PAC.pdf (364kB)
This file has been downloaded 92 times





Chemistry = Chem + is + Try
View user's profile View All Posts By User
Corrosive Joeseph
International Hazard
*****




Posts: 622
Registered: 17-5-2015
Location: The References Forum
Member Is Offline

Mood: Cyclic

[*] posted on 24-2-2019 at 09:16


Quote: Originally posted by Waffles SS  
All possible way for synthesis (RS)Phenylacetylcarbinol


Thank you for that........... But the racemate is not a desirable end product, because it kinda defeats the whole idea of this route.


/CJ




MSDS Addict and OTC Slut
View user's profile View All Posts By User
Waffles SS
Fighter
*****




Posts: 917
Registered: 7-12-2009
Member Is Offline


[*] posted on 24-2-2019 at 09:24


Quote: Originally posted by Corrosive Joeseph  
Quote: Originally posted by Waffles SS  
All possible way for synthesis (RS)Phenylacetylcarbinol


Thank you for that........... But the racemate is not a desirable end product, because it kinda defeats the whole idea of this route.


/CJ



Attachment: L-PAC.pdf (404kB)
This file has been downloaded 83 times

[Edited on 24-2-2019 by Waffles SS]




Chemistry = Chem + is + Try
View user's profile View All Posts By User

  Go To Top