Quercetin Chalcone develops like Pyrogallol

[Alan Johnson]

Patented in 1999, Quercetin Chalcone (QuCh) is sold in health supplement capsules.Capsules of Quercetone contain 250mg QuCh and capsules of Quercenase (which I ordered by mistake) contain 250mg QuCh and 100 mg Bromelain.I doubt the Bromelain in the capsules I used had any effect but cannot be sure,Quercetone would have been better.

1st QuCh Staining Developer:
Metol.......................0.2g
Sodium Metaborate.....5g
QuCh.......................2.5g (contents of 10 capsules)
Water to...................1L

The quercenase was hard to dissolve, I dissolved it with stirring in the Metol +Metaborate dissolved in water at 100C.(Care, unknown hazard).

HP5 exposed at EI 200 was developed 30min 20C, agitate 10s/min in 1st QuCh.
A dark brown-yellow stain was produced and there was a relief image in the emulsion.
Attachments show scans of 0.2 in square sections of HP5 developed in 1st QuCh and in Pyrocat HD, equally sharpened.
QuCh costs ~$30 for 15g, Pyrogallol costs ~$20 for 100g.
This post is a spin off from a less specialized thread on Photo.Net:
http://photo.net/black-and-white-photo-film-processing-forum/00Y1wj
Thanks for comment.

 

[Alan Johnson]

You never heard of it as a developer because I just found it.
QuCh is like Pyrogallol because Pyrocatechol forms a complex with Metaborate and will not work with it.

It took Hutchings years to optimize PMK so dont take my formula seriously, I put it up to illustrate what type of agent QuCh is.

It may be difficult to make up QuCh as a 2 part developer like PMK Pyro,with a preservative and good activity, eg it seems rather hard to dissolve.

 

[Kirk Keyes]

Interesting - it's a flavinoid with polyphenols on it, so no wonder it works as a developer.
http://en.wikipedia.org/wiki/Quercetin

I used tannic acid a few years ago and it works as a staining developer as well.
http://en.wikipedia.org/wiki/Tannic_acid

My tannic acid developer was similar to yours except I had to use about 5g tannic acid per liter to get good contrast.

Tannic acid seems to dissolve a bit better than the Quercetin, although there always seems to a bit of lint in the solution from it...

 

[MDR]

Kirk how did your Tannin developer compare to other staining developers and is it possible for you to post the formula ?

Thanks Dominik

 

[Alan Johnson]

http://albumen.conservation-us.org/library/monographs/sunbeam/toc.html
In 1864 they knew of Tannic acid, Gallic Acid and Pyrogallic acid developers (CH XIV).
But in the dry plate Collodion process Tannic acid was only used to preserve the emulsion,Pyrogallic acid was used as a developer (Ch XXXVII).
So they probabably must have thought Pyrogallic acid was a better developer than Tannic Acid.The reason for thinking this is not clear but it is not encouraging to start a new investigation of Tannic Acid.

 

[Alan Johnson]

Plant chemicals that might dissolve in alkaline solution and have not been looked at might include Resveratrol and Ellagic Acid.The molecules are smaller and since have OH groups may form staining developers.

 

[Kirk Keyes]

My interest in trying tannic acid was from its low toxicity and it's large molecular size. I wondered if it would work more on the surface of the film as I suspected it would not diffuse very quickly into the gelatin, because of the large molecular size.

I need to find the negs to confirm, but it looks similar in stain to pryocatechol.

I'm sure the reason they went with pyrogallol rather than tannic acid is the large amount of tannic acid needed in the formulation. Tannic acid is just not as vigorous as pyrogallol.

I really didn't go more than about 3 tries/reformulations. I'm certain that adjustments could be made formula wise to cut down on the amount of tannic acid needed to get good development.

 

[Athiril]

You never heard of it as a developer because I just found it.
QuCh is like Pyrogallol because Pyrocatechol forms a complex with Metaborate and will not work with it.

It took Hutchings years to optimize PMK so dont take my formula seriously, I put it up to illustrate what type of agent QuCh is.

It may be difficult to make up QuCh as a 2 part developer like PMK Pyro,with a preservative and good activity, eg it seems rather hard to dissolve.

Alan, I told you about it as a developing agent if you recall.


It isn't difficult to dissolve, you need to look at other solvents that aren't simply just water. Such as acetone, dimethyl sulphoxide, and ethyl acetate (which you should be able to easily make a mix of with ethanol, which also has some solubility, though not as high as these)

 

[nworth]

One of the alternative names for QuCh is meletin. I think I have seen that mentioned before as a weak developing agent.

 

[Alan Johnson]

Alan, I told you about it as a developing agent if you recall.


It isn't difficult to dissolve, you need to look at other solvents that aren't simply just water. Such as acetone, dimethyl sulphoxide, and ethyl acetate (which you should be able to easily make a mix of with ethanol, which also has some solubility, though not as high as these)

I only said I was the first to use the water soluble Quercetin Chalcone, it made a working developer.
AFAIK the original suggestion to use Quercetin (which put me onto the chalcone) has not yet resulted in a working developer formula.I hope it does eventually progress beyond theory.

 

[DarkroomExperimente]

very interesting

 

[Athiril]

Alan: I have not seen you say such a thing anywhere, what I have seen you say is that no one has heard of it before because you discovered/found it and am only now telling people about it.




I had already made a working developer with it months beforehand, as I said the information on the blog post I first gave out was a recount of the very first time I stumbled onto it while trying to do something else entirely, I gave the information out because I wish to see progress made quicker than what I can possibly do on my own. All this information can be found there on the thread.

I do not wish to be rude, because you have done a fair few good things, but I do feel like this needs saying.


You have since published much more and experimented with it more in this context than I or anyone else has since that thread which is good, but this is after the fact.


That aside which is not important or central to this point, what you actually said was "You never heard of it as a developer because I just found it." in response to someone saying they had never heard of this before. Adding on chalcone to the end of it doesn't suddenly make it unique or different idea. Nor were you ever looking into that independently anyway. Their response wasn't "oh well I've heard of quercetin before, but not quercetin chalcone", it was complete unfamiliarity with the entire thing.

It may sound petty and egotistical but I do I take issue with it as I really dislike this kind of thing as I feel it is a dishonest thing to say.

Because you never 'just found it', you were told about it's capability as a developing agent. The ketone form of quercetin, quercetin chalcone comes under the umbrella quercetin, as do all it's forms, as I can tell you my organic extract is likely to be a sugar form, and not straight quercetin, the idea of it as a developing agent was already disseminated in that thread, using the given knowledge of it as a developing agent and googling up solubility data and ways to solubilise the chemical does not constitute 'just finding it'.

 

[Alan Johnson]

If the link to the photo.net thread given in the first post is followed it is perfectly obvious that my use of quercetin chalcone to make a working developer derives from the results of Dan Lee with quercetin.
I would like to see some results from Mr Lee.

 

[DarkroomExperimente]

I'm interested in natural sources of developers & read that shallot onions are a good source of quercetin...does anyone know of other natural sources of quercetin?

While you guys take the more sophisticated approach, I'm going to run to the store to get a shallot and a red onion...then toss them in the blender and see what happens.

 

[Ole]

I'm interested in natural sources of developers & read that shallot onions are a good source of quercetin...does anyone know of other natural sources of quercetin? ...

The name is often a hint. I'm willing to bet that "Quercetin" refers to "Querqus", which means "Oak".

 

[DarkroomExperimente]

The name is often a hint. I'm willing to bet that "Quercetin" refers to "Querqus", which means "Oak".

thank you! from wikipedia: "Quercetin is a flavonoid widely distributed in nature. The name has been used since 1857, and is derived from quercetum (oak forest), after Quercus"


I just got some quercetin from the GNC store....label says it's quercetin dihydrate

I notice that quercetin can be found in buckwheat...and buckwheat honey is apparently high in antioxidants...I'd be interested in learning if there's any quercetin in buckwheat honey

 

[isshin]

I hate to nerco-bump but has anyone tried using this as an additive in caffinol?

 

[Alan Johnson]

Recently , hydroquinone has been shown to work with caffenol so quercetin chalcone may do likewise:
http://www.ipernity.com/blog/chrono/497137

However,IIRC the proprietary form of quercetin chalcone I used was called Quercetone.
This is now in the process of being replaced by another substance, quercetin phytosome:
http://www.thorne.com/Products/Antioxidants-Flavonoids/Flavonoids/prd~SB330.jsp

Unless you can find a future source of quercetin chalcone it might be better to do what has been suggested above and dissolve quercetin in a non-water solvent if wishing to investigate this..

 

[isshin]

Good to know, has anyone messed around with the new chem yet?

 

[Alan Johnson]

Sodium hydroxide (aka caustic soda, lye) is hazardous:
http://www.ccohs.ca/oshanswers/chemicals/chem_profiles/sodium_hydroxide.html
But it dissolves Quercetin dihydrate:
Dead Link Removed
Worth a try as a staining developer, I ordered some Quercetin capsules (you have to avoid those which are not the pure stuff).

 

[Ian Grant]

Alan, I posted a question about Quecertin on this Forum 5 years ago. I have a jar of Kodak Quecertin, packaged by Kodak Ltd (Harrow) marked as made by Eastman Kodak in the US, it also says "Not for Drug Use". It came from a metallurgy lab (Murex) in Essex that had closed in the late 1980's.

Ian

 

[Harold33]

hard to compare the two from little scans.
What's about overall contrast, compensating effect, grain, exposure latitude, speed, and so on ?

 

[Alan Johnson]

Harold,
If you refer to Quercetin Chalcone, I never checked it out as it is so expensive compared to Pyrogallol.
Quercetin may be similar, if it dissolves in sodium hydroxide, which I hope to test out of curiosity.
Kodak probably knew about similar substances, from Mees & James 3rd Ed p282:
"Often an inactive compound in highly alkaline solution may be hydrolyzed or partially oxidized and hydroxylated to form a new species fully capable of developing an emulsion"

 

[Alan Johnson]

Developer from Quercetin Capsules

I now tried to make a staining developer starting with Quercetin capsules ,not the more soluble Quercetin Chalcone capsules mentioned above.
2.5 g Quercetin poured from capsules was added to 4 g Sodium Hydroxide (Lye) in 100 ml water. This did not all dissolve immediately and was left for 7 days in a 100ml sealed glass bottle with occasional shaking.The level of suspended material in the solution gradually fell but it was not all dissolved after 7 days when the clear orange solution was filtered off through cotton wool.It was made up to 1liter and 0.2g Metol and 15 g sodium bicarbonate (Arm & Hammer baking soda) were added.The pH was 9.8 +/- 0.1.
Pics of Fomapan 400 negatives developed 30min 20C and a positive are attached.

The working solution was:
Metol.........................0.2g
Quercetin ..................2.5g
Sodium Hydroxide.......4.0g
Sodium Bicarbonate...15.0g
Water to.....................1L

Conclusion:
It is possible to make a staining developer from Quercetin capsules but at present:
(1) It is not clear if the development is due to dissolved Quercetin or Quercetin Hydrate formed by reaction with the Lye.
(2) If there is an easier way of making it up, preferably avoiding hazardous sodium hydroxide (see previous posts).

 

[Alan Johnson]

Owing to the low solubility of Quercetin compared to pyrogallol,pyrocatechin and hydroquinone (all in staining developers), it seems not possible to make a water based concentrate of it, and unlike these others, Quercetin cannot be made into a water based stock solution concentrate.I therefore tried a dilute 1-shot solution:

Metol .................................0.2g
Quercetin............................2.5g
Sodium Carbonate anh..........5.0g
Water to...............................1L

These were shaken up together in a full sealed glass bottle, after ~24 hrs most of the Quercetin appeared to have dissolved.
APX 100 was developed 30m 20C.This worked well, giving brown stained negatives.I verified these were also tanned by bleaching in !0% Potassium Ferricyanide and Bromide solution and fixing.
A relief image formed by tanning was visible.
That carbonate solution worked indicates the it is likely Quercetin and not some hydroxylated derivative that is the developing agent.

AFAIK the only commonly used 1 shot solution that is premixed just before use is Caffenol so that is next to test.