Clear citric water pulls turn dark brew as reduced

[modern]

Any explanation on why an almost clear extract becomes dark after reducing? I think most of the sugars were pulled with PC pulls

So for my caapi yea I do 3-4 PC pulls then reduce everything to 1.5-2L. These pills tend to be a creamy brown for 1-2 and others just a red/brown liquid.
Usually just toss the caapi after this but decided to do some cold acid pulls in the spent bark since under 365nm light it is still very blue with just water soak.
24h citric acid soak leads the the first photo. I did 3 soaks and am reducing and the once clear liquid becomes a very dark color.
The last photo shows the blue of the spent caapi in water soak. Poor photo but shows what I needed

 

[modern]

First 3-4x water pulls with PC vs BLACK 2-3x cold citric water pulls

 

[modern]

it seems that low ph pulls lots of other impurities since when increasing ph to precipitate while still acidic there is a black precipitate that forms around ph 4-5? making the tea brown. The precipitate later redissolves around 6-7ph and cannot be seen again.

Better photo of the caapi vine in citric water after (normal waters pull for tea no acid added).

I'll add photos of the impurities that are pulled with more acid later

 

[modern]

The first photo is the precipitate that forms when still acidic and the second is when it starts to become a more recognizable beige or creamy brown color. Still acidic.

 

[modern]

Forgot to update but lots of harmalas are left behind from my normal tea PC pulls. From 1.5kg I pulled an additional 5-6g of harmalas using cold Citric acid soaks. Small amount overall 0.4% but enough for experiments

Going forward I’ll do separate pulls of vine after the 3-4x pulls I do for tea.

 

[modern]

So after doing citric acid precipitate which yielded red crystals from water and also ascorbic acid yielded brown powder (not impurities since already cleaned via a/b) I’d guess harmalol and Harmol due to tiny percentages of yield and descriptions in references. But Idk

I added lye to the charcoal cleaned acid water (was reddish became light orange) and started with the normal very light tan/off white precipitate. As time passes started to become yellow than orange. Now after 30 minutes or so the precipitate became red. I’ve never had this happen before.

Is it because of the vitamin c? Very unlikely it is any impurities

 

[modern]

Sodium ascorbate becomes oxidized and turns red and red brown… mine became brick red

So will skip this next time

 

[modern]

So added salt to a portion of the vitamin c solution and got the hcl precipitate. I think may be best way precipitate using this acid?

The brick red Freebase was filtered and left a get black lye solution which seems to be a very dark red. Eyeballing the precipitate seems to be correct amount.

Sodium ascorbate I feared may have precipitated but the solubility is very high 50-60g per 100ml of water so doubtful.

 

[modern]

So I added malic acid to the Freebase and it started off the normal orange red tone but later became very dark. pH is acidic maybe 4 so I don’t think the Sodium ascorbate is the issue but may be the reason.

Looking thru the solution it is a dark red tone however looking from the other side with uv from sunlight it is a very dark green tone.

No precipite formed in acidic solution and seems hcl is the main one by adding salt when acidic. Oxalic acid will be an issue since sodium oxalate will precipitate most likely.

I think I’ll make Freebase and try getting crystals from hot ethanol.