Pine cone extraction PT2 and update

Before I was deleted I did some posts on trying to extract the pigments from green pine cones. I tried steam distillation and Solvent (IPA) via Soxhlet and by soaking for days.
The results from Solvent were ok but had a few draw backs. I want these pigments to colour soap with natural plant pigments instead of mica etc.
Once I had recovered most of the solvent from the cone solution it became unstable, both exposure to light and Sodium hydroxide altered the colour. In the case of sodium hydroxide it bleached the colour out completely. If I left some of the IPA in the solution then it did hold the colour better, however that then gave me the problem of having an unacceptable amount of solvent in what was meant to be a mild soap.
I cant find the pics now that were deleted but things have moved on.

Some back storey

I had collected some other smaller cones and this time they were male, they behave the same way as the female cones but gave a lighter pigment.
I wanted to practice some lab techniques and decided I would try my hand at recrystallizing, again I posted it all on here so many my remember them. I decided to use salt as it was dead cheap, very safe and easy to work with.
I ended up over boiling it and the crystals fell out all most at once and were way too small, I was advised to try and evaporate it slowly in order to get larger crystals.
I put this super saturated solution in a large (ish) square glass pyrex dish and left it under the window on the floor out the way, this was meant to be temporary while it cooled off a bit.
A couple of days passed and not much had happened! considering the surface area I was surprised no other crystals had appeared, anyway I had already decided to start it all again but do some different concentrations and temperatures etc.
At this time I was also having problems with sodium hydroxide prills turning to liquid!! I got that sorted but had a beaker with around 50-60ml of the sodium hydroxide crystals all melted.
Final decision was made to just pour it into the salt solution and see salting in action! I was curious as to how big the crystals if any would be.
Well disappointing to say the least! All tiny crystals and all appeared almost at once.
Job done time to dispose of the liquid and move on, however.............. I had lunch and when I went back I knocked a pine cone off the window shelf and into the dish!
It started to turn black!!!! not much, but a little at first.
So I decided to leave it, 4 days later I get this...........





The picture really dosnt do the colour justice at all! And best of all I have tested with very strong Hydroxide solution and the colour dosnt budge! In fact its really hard to dilute the colour!
At the moment I dont want to go into details until I have sorted it out properly, but I have found a way to change the colour and fix it, this means I can get from the very very dark claret red all the way to this





I have tried it in a little soap and so far the colour dosnt budge . I know it dosnt sound like a big deal but for soap making its a real bonus, plus its nice and easy .
I will give more details later when I have it sorted out properly

I'm all for experiments and nice pictures. A little suggestion because I know you're kinda new to the boards. It would help us readers a bit if you mentioned what you think or know the crystals are(chemical composition).

Also a little tip I was told years back from a home chemist for evaporating solutions in wide dishes outside, was to cover them with a thin piece of cotton. Like a clean old white cotton t-shirt or similar. It does lengthen evaporation time, but no visible dust/bugs/cat hair etc enters the solution/crystals.

I do have to admit the color is pretty nice and I had no idea green pine cones would yield that. It just makes me wonder what chemical(s) are at play.

Quote: Originally posted by smaerd

I'm all for experiments and nice pictures. A little suggestion because I know you're kinda new to the boards. It would help us readers a bit if you mentioned what you think or know the crystals are(chemical composition). Also a little tip I was told years back from a home chemist for evaporating solutions in wide dishes outside, was to cover them with a thin piece of cotton. Like a clean old white cotton t-shirt or similar. It does lengthen evaporation time, but no visible dust/bugs/cat hair etc enters the solution/crystals. I do have to admit the color is pretty nice and I had no idea green pine cones would yield that. It just makes me wonder what chemical(s) are at play.

Hi
Sorry about the crystal thing, in case you dont know my other account was accidentally deleted and all the posts and thread I had done were also deleted.
So this time instead of redoing all the previous thread I did on recrystallization I just shortened it. However I did say in the above post what they were!

from above

"I wanted to practice some lab techniques and decided I would try my hand at recrystallizing, again I posted it all on here so many my remember them. I decided to use salt as it was dead cheap, very safe and easy to work with.
I ended up over boiling it and the crystals fell out all most at once and were way too small, I was advised to try and evaporate it slowly in order to get larger crystals."

The reason I didnt cover the dish was because as the original post explained I got crystals forming in the flak neck. I didnt want to go into much detail about something that was originally a long thread.
The point is it was a dish with super saturated salt solution. Thats the bit that matters. If you try and extract the colour from this species of male cone with just hydroxide it dosnt give you the pigment.
It dosnt give you the pigment with Salt alone. I dont know what chemicals it contains yet, my first priority is looking for pigments I can control in the soap making process. Once I find some (like this one) I extract and will then investigate dome more.
Under the micro scope there are 6 micro bands of colour, the female cone from this species has 4. I will run a TLC plate once I get some more solvents.
The reason it wasnt covered was simply because in the original thread about it, it was clear I had messed things up, I had already decided to redo all the salt experiments at that point.

I did find a couple of the pics from the original thread, the following pics are the IPA solution from the female cone, as it was a long thread before I wont rehash all the details here again