o-Phthalaldehyde CAS 643-79-8
Directory Guidance on o-Phthalaldehyde
o-Phthalaldehyde (OPA) or ortho-phthalaldehyde is a compound of formula C6H4(CHO)2. Often abbreviated as OPA, this molecule is a dialdehyde consisting of two formyl (CHO) groups attached to adjacent carbon centers on a benzene ring.
This pale yellow solid is a component in the synthesis of heterocyclic compounds and a reagent in amino acid analysis. OPA is dissolved in aqueous solution with pH < 11.5. Its solutions degrade on UV exposure and exposure to air.
O-phthalaldehyde is an important pharmaceutical and chemical intermediate. It was mainly used in amine alkaloids, fluorometer histamine determination reagents and medical inspection.
Since it was used for endoscope disinfection in 1994 and found that it has a good disinfection effect, many studies have been carried out on the disinfection of ortho-phthalaldehyde abroad, and it has been developed into a new type of high-efficiency disinfectant and passed the US FDA. Certification.
Nature and Specifications:
- Density: 1.13
- Boiling point: 83-84 °C (0.7501 mmHg)
- Melting point: 55-58 °C (ignition)
- Flash Point: >230°F
- Refractive index: 1.622
- Water solubility: easily soluble
o-Phthalaldehyde has many chemical applications in the pharmaceutical and chemical industries. It is mainly used in medicines, dyes, amino acid derivatization reagents, etc., and is an important pharmaceutical intermediate.
In the pharmaceutical industry, o-Phthalaldehyde can be used to synthesize the new anti-platelet aggregation drug indobofen, and it is also an analytical reagent in the chemical field. It is also used in the production of eye ointments, eye drops and other medicines.
used as a disinfectant
Orthophthalaldehyde is the latest high-efficiency and safe antibacterial disinfectant for external use, which is used as the disinfection and sterilization of endoscopic surgical instruments in hospitals. Compared with the disinfectant glutaraldehyde (GTA), o-phthalaldehyde has the advantages of broad-spectrum, high efficiency, and low corrosion of glutaraldehyde, as well as its own characteristics such as less irritation and low concentration.
In addition, o-phthalaldehyde also has a good killing effect on glutaraldehyde-resistant mycobacteria isolated in recent years. Therefore, o-phthalaldehyde has the potential to become a substitute for glutaraldehyde.
Used As Reagent
o-Phthalaldehyde can be used as an amino acid derivatization reagent for fluorescence detection. The reaction can be completed in one minute, but the product is unstable and needs to be detected immediately.
Analytical reagents in the chemical area: As an amine alkaloid reagent, it is used for the determination of primary amines and also peptide bond disintegration items by fluorescence method.
Fluorescent reagent for pre-column HPLC separation of amino acid derivatives and flow cytometric measurement of protein thiol groups.
Action and Reaction Mechanism
O-phthalaldehyde belongs to the dialdehyde compound. Like glutaraldehyde, it mainly reacts with the amino acid groups of amino acids, proteins and other components of microorganisms through the cross-linking reaction of aldehyde groups. Many experiments have shown that the cross-linking effect of o-phthalaldehyde is weaker than that of glutaraldehyde. This may be because phthalaldehyde can only react with the primary amino group (-NH2), so it can only react with the lysine, arginine in the peptide chain and the amino acid at the end of the peptide chain.
A hypothesis has been proposed to explain the weaker crosslinking effect of phthalaldehyde: first, the addition reaction of aromatic aldehydes (such as o-phthalaldehyde) is weaker than that of aliphatic aldehydes (such as glutaraldehyde). Second, the structure of ortho-phthalaldehyde contains a benzene ring, which makes the spatial structure of ortho-phthalaldehyde lack extensibility, so it is not easy to fully react with amino-containing substances by adjusting the spatial conformation. On the contrary, glutaraldehyde has greater extensibility and is easy to react with the amino group in the substance.
O-phthalaldehyde has good stability in the pH range of 3-9, and its solution can be used continuously for 14 days. The American iCdxe company has developed a test paper to precisely monitor the concentration. Some data show that if an automatic endoscope cleaning program is used, it can be used repeatedly 82 times before reaching the minimum effective concentration, while glutaraldehyde is only used 40 times. Phthalaldehyde is not harmful to many metals, plastics and other substances.
- “Acute Inflammation and Immune Responses of Orthophthalaldehyde in Mice” – Springer, Link | 30 January 2010.
- “Carboxylic acid-catalyzed asymmetric acetalization to prepare phthalate prodrugs” – Thieme | Excerpt: April 18, 2022.
1. Certificate Of Analysis (COA)
2. Material Safety Data Sheet (MSDS)
3. Route of synthesis (ROS)
4. Method of Aanlysis (MOA)
5. Nuclear Magnetic Resonance (NMR)
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