What Is Phorone?
Phorone, commonly known as diisopropylidene acetone, is an organic compound with the formula C9H14O. It features two double bonds within its structure.
The compound is scientifically named 2,6-dimethyl-2,5-heptadien-4-one, and identified by the CAS number 504-20-1.
Uses of Phorone
Phorone is utilized as a powerful glutathione-depleting agent in physiological studies. It can also be derived from certain terpenoid compounds.
Glutathione, a tripeptide composed of glutamic acid, cysteine, and glycine, features a thiol group (-SH group). This group’s reducing property allows glutathione to reduce peroxides and reactive oxygen species, maintaining a reducing environment within cells. Moreover, glutathione can conjugate foreign substances, such as toxins and drugs, facilitating their expulsion from the cell.
In physiological research on animals like rats, phorone markedly reacts with glutathione’s thiol group. This reaction effectively deactivates glutathione, enabling the study of glutathione deficiency symptoms and its physiological roles and relationships to diseases.
Properties of Phorone
Phorone, with a molecular weight of 138.20, presents as aromatic yellow crystals or a dark yellow liquid at room temperature, with a melting point of 28°C and a boiling point of 198-199°C. It is a flammable substance, having a flash point of 79°C, and is stable under standard storage conditions, although it reacts vigorously with strong oxidizers. Its density is 0.885 g/mL, and it is recommended to keep it away from heat, sparks, and flames due to the risk of hazardous decomposition into carbon oxides.
Types of Phorone
Available primarily for research and development, Phorone is sold in quantities like 1g and 5g, designed for easy laboratory handling. It finds applications in biochemistry, physiology, and synthetic organic chemistry experiments.
Other Information on Phorone
1. Synthesis of Phorone
Phorone is synthesized through the self-condensation of acetone in the presence of acidic conditions, such as hydrochloric acid. Initially, two acetone molecules undergo aldol condensation and dehydration to form mesityl oxide. Subsequently, the carbonyl group of mesityl oxide enolates and nucleophilically adds to another acetone molecule, leading to a second aldol condensation and dehydration to yield Phorone. The reaction sequence includes enolization to mesityl oxide, followed by Michael addition, cyclization, and dehydration to produce isophorone.
2. Chemical Reaction of Phorone
When condensed with ammonia, phorone forms triacetoneamine, a precursor in synthesizing 2,2,6,6-tetramethylpiperidine, a sterically hindered amine.
3. Precautions for Handling Phorone
While phorone is not specifically classified under GHS or subject to regulations by safety and fire laws, safety precautions are advised. These include installing adequate local exhaust and general ventilation systems and wearing appropriate personal protective equipment like goggles and protective clothing. Immediate washing is recommended upon skin or eye contact.