γ-Butrolactone, also known under the IUPAC name Dihyrdofuran-2(3H)-one, is used as a stain remover, superglue remover, and paint stripper. It is also used in the human body because GBL is a prodrug of GHB. GBL is consumed by a human and then transfered into GHB by lactonase enzymes in the blood. GHB stands for γ-Hydroxybutyric acid. At one time, GBL was sold under the names Revivarant or Renewtrient as a human growth hormone. In high doses, it acts as a sedative and can make a human unconscious. With low doses, it has a euphoric effect. GBL is commonly called “liquid ecstasy”. If excessive doses are taken irrational behavior, severe sickness, coma, or death can occur. GBL is addicting and withdrawals can lead to delirium tremens, seizures, and can cause death in many circumstances. In layman terms, do NOT consume GBL.
γ-Butrolactone has a melting point of -43.53° C and a boiling point of 204° C. The pH of this compound is 4.5, making it acidic. It is soluble in water, as well as CCl4, acetone, bezene, methanol, and ethyl ether. GBL can be synthesized from gamma-hydroxybutyric acid (GHB) by removal of water or by distillation from such a mixture. It may also be obtained via oxidation of tetrahydrofuran (THF).1 One such process, which affords GBL in yields of up to 80%, utilizes bromine generated in situ from an aqueous solution of sodium bromate and potassium hydrogen sulfate.1 Another process can proceed by using commercially-available calcium hypochlorite in the presence of activating acetic acid and an appropriate solvent such as acetonitrile.1
Example Synthesis:
Example Synthesis:
Example Reaction Where γ-Butrolactone is Converted to Another Caboxylic Acid:
Sources: 1. http://en.wikipedia.org/wiki/Gamma-Butyrolactone
I would say "short and sweet" but that would definitely be a lie (inside joke giggle giggle). This blog is "pretty darn good" if I had to put it into words. You have all of the essential information plus a lot of extra stuff. I was not able to find any reactions where my compound was converted to a different amino acid but you seem to have gone above and beyond with that part of the assignment by showing the picture where it was converted to other carboxylic acids. I like how you told about the many ways GBL is used in real life situations as well as in the human body. The only problem I had with your paper was that at the beginning it took me a little while to figure out whether GHB or GBL was the compound you were writing about in your blog. However after a little deliberation I was able to infer as to which one you were discussing.
ReplyDelete