ROSOLIC ACID Chemical Properties

Melting point:

309°C (decompose)

Boiling point:

372.4°C (rough estimate)

Density 

1.2497 (rough estimate)

refractive index 

1.4200 (estimate)

storage temp. 

Store at room temperature.

solubility 

Practically insoluble in water, benzene; freely soluble in ethanol

form 

Crystalline Powder

Colour Index 

43800

pka

6.98(at 25℃)

color 

Red-brown to brownish-red

PH Range

6.8(YELLOW)--8.2(RED)

Water Solubility 

Soluble in alcohol, sodium hydroxide, potassium hydroxide and strong acids. Insoluble in water.

λmax

534.6nm, 479.5nm, 482nm

Merck 

14,881

BRN 

2055205

Stability:

Stable. Incompatible with strong oxidizing agents.

Major Application

electrorheological materials, films patterning, antireflective coatings, thermochromic materials, photoresists, film patterning, recording materials, lithium battery, semiconductors, printing materials, inks, corrosion inhibitors, adhesives, drugs, detecting viable cells, treatment of Alzheimer’s disease

CAS DataBase Reference

603-45-2

EPA Substance Registry System

2,5-Cyclohexadien-1-one, 4-[bis(4-hydroxyphenyl)methylene]- (603-45-2)

Safety Information

Hazard Codes 

Xi

Risk Statements 

36/37/38-36/38

Safety Statements 

26-36-37/39

WGK Germany 

3

TSCA 

Yes

HS Code 

29145090

MSDS

• Language:English Provider:SigmaAldrich
• Language:English Provider:ACROS
• Language:English Provider:ALFA

ROSOLIC ACID Usage And Synthesis

Chemical Properties

red crystals or powder

Uses

activates heme oxygenase, anti-oxidative stress, inhibits DNA fragmentation

Uses

A red coloring medium made from phenol or carbolic acid. It is soluble in alcohol and ether but insoluble in water. When fabrics were steeped in this solution, the color was nonactinic and therefore safe for darkrooms, windows, and doorways. Aurin was also mixed with water-soluble gums and brushed on the backs of collodion and silver bromide gelatin plates as an antihalation layer.

Uses

Rosolic acid is used as a pH indicator in the range from 5.0 to 6.8. It acts as an intermediate in the manufacturing dyes. It is involved in the activation of heme oxygenase and in the inhibition of DNA fragmentation. It finds application in the selective isolation of coliform bacteria.

Definition

ChEBI: Aurin is a diarylmethane.

Purification Methods

It forms green crystals with a metallic luster, but the colour depends on the solvent used. When recrystallised from brine (saturated aqueous NaCl) acidified with HCl, it forms red needles, but when recrystallised from EtO/AcOH, the crystals have a beetle iridescent green colour. It has been recrystallised from Me2CO (although it dissolves slowly), methyl ethyl ketone, 80-95% AcOH and from AcOH/*C6H6. An aqueous KOH solution is golden yellow, and a 70% H2SO4 solution is deep red in colour. An alternative purification is to dissolve this triphenylmethane dye in 1.5% of aqueous NH3, filter, and heat to 70-80o, then acidify with dilute AcOH by adding it slowly with vigorous stirring, whereby the aurin separates as a brick-red powder or as purplish crystals depending on the temperature and period of heating. Filter off the solid, wash it with H2O and a little dilute AcOH, then H2O again. Stir this solid with Et2O to remove any ketones and allow it to stand overnight in the Et2O, then filter and dry it in air then in a vacuum. [Gomberg & Snow J Am Chem Soc 47 202 1925, Baines & Driver J Chem Soc 123 1216 1923, UV: Burawoy Chem Ber 64 462 1941, Beilstein 8 IV 2646.]

ROSOLIC ACID(603-45-2)Related Product Information

• Aluminon
• Ammonium metavanadate
• Ferrous chloride
• Sodium thiocyanate
• Trimellitic Anhydride
• Phenolphthalein
• Potassium dichromate
• RHODIZONIC ACID DIHYDRATE
• ROSOLIC ACID
• AURINTRICARBOXYLIC ACID
• TIMTEC-BB SBB006515
• P-ROSOLIC ACID SODIUM SALT
• AURINTRICARBOXYLIC ACID TRISODIUM SALT
• 4-[(4-hydroxy-3-methylphenyl)(4-hydroxyphenyl)methylene]cyclohexa-2,5-dien-1-one
• SALOR-INT L162582-1EA