I go through these spells where I am absolutely obsesses with understanding the chemistry of henna. I have a bunch of questions!

1. Why do water mixes turn brown, but acid mixes don't? I think this is an effect of reduction from lawsone (HNQ) to its hydroquinone counterpart 1,2,4-trihydroxynaphthalene (THN). If your familiar with the diagram of a lawsone molecule, THN looks just like it except the Os sticking of the top and bottom of the second carbon ring each have an H stuck to them. Could it be that HNQ is orange (ok, we know that's true) and that THN is colorless? Acid reduces HNQ temporarily to THN? IF so does it serve any useful function.

2. Where does lawsone connect with keratin. I have a lot of sources that lead me to believe that this happens at the thiol of a cysteine. Cysteine is an amino acid. A thiol is a part of the molecule that has a sulfur and a hydrogen atom, or SH group. I've been told that these groups are non reactive in an acidic environment. Hmmm. It actually appears that rather than non-reactive, they're just slow to react. (Besides, I've got all kinds of papers in front of me talking about michael addition reactions with thiols. Michael addition prefers an acid environment.) It does appear, however that the Ss like to bind to each other. These are S-S (or disulphide) bridges. The trick may be to break these bonds to get more SH groups available to bond to the lawsone. I tried something today. I pre teated a patch of skin with alcohol (my control) another with ammonia, and a 3rd with lemon juice. Then I put henna on over all three patches. We'll see what happens.

3. What's the brown slime on top of your paste when it's released? I think it is strands of HNQ all linked together. They're just too big to penetrate skin, or anything else so they don't dye anything. I wonder if we can do anything to test this? What would break the links? If we knew we could mix some of that stuff with something that would break the links and see if it becomes more useful.

I've got more good ones, but I'm afraid I'm going off the deep end...

IF YOU KNOW A NICE CHEMIST PLEASE HAVE HIM/HER GET IN TOUCH WITH ME. I'M GOING MAD....