Oxaceprol Chemical Properties

Melting point:

132-133 °C (dec.)(lit.)

alpha 

-119 º (c=4 in H2O)

Boiling point:

303.8°C (rough estimate)

Density 

1.3346 (rough estimate)

vapor pressure 

0Pa at 20℃

refractive index 

1.4490 (estimate)

storage temp. 

Sealed in dry,2-8°C

solubility 

DMSO : ≥ 32 mg/mL (184.79 mM)

form 

Crystalline Powder

pka

3.48±0.40(Predicted)

color 

White

optical activity

[α]20/D 119°, c = 4 in H2O

Merck 

14,6903

BRN 

84043

InChIKey

BAPRUDZDYCKSOQ-RITPCOANSA-N

LogP

-1.51 at 20℃

CAS DataBase Reference

33996-33-7(CAS DataBase Reference)

EPA Substance Registry System

L-Proline, 1-acetyl-4-hydroxy-, (4R)- (33996-33-7)

Safety Information

Hazard Codes 

Xi

Risk Statements 

41

Safety Statements 

26-36

WGK Germany 

3

F 

10

TSCA 

Yes

HS Code 

29339900

MSDS

• Language:English Provider:Oxaceprol
• Language:English Provider:SigmaAldrich
• Language:English Provider:ALFA

Oxaceprol Usage And Synthesis

Chemical Properties

White powder

Originator

Jonctum,Merrell,France,1970

Uses

trans-1-Acetyl-4-hydroxy-L-proline can be used:

• In the stereospecific synthesis of 4-fluoroglutamic acid.
• To synthesize molecular targets for von Hippel-Lindau (VHL) E3 ubiquitin ligase.
• As a precursor to synthesize pseudopoly(amino acids) such as poly(trans-4-hydroxy-4-acyl-L-proline ester) and a biodegradable polymer, poly(lactic acid-glycolic acid-4-hydroxyproline).

Manufacturing Process

16.7 g (0.127 mol) of L-hydroxyproline are dissolved in 400 ml of pure boiling acetic acid. With vigorous boiling and agitation, a mixture of 13.7 ml (0.154 mol) of rectified acetic anhydride and 250 ml of pure acetic acid is added during 25 minutes. Without discontinuing the stirring, contents of the flask are cooled by simply causing fresh air to circulate externally round the flask until the temperature of the mixture is reduced to about 35°C. The acetic acid is removed by using a rotary evaporator without exceeding 35°C under a vacuum of about 15 mm Hg. After one hour, 20 ml of anhydrous toluene are added, then 10 ml of anhydrous acetone; the mixture is homogenized and concentrated again as above during 30 minutes. Then 25 ml of acetone are added again, and subsequently 20 ml of toluene, the product being concentrated again; gradually the solution is converted into an amber-colored crystallized paste. Finally, 30 ml of acetone are added to the residue, and stirring is carried out until the oily fraction surrounding the crystals is dissolved. The product is then cooled in an ice chamber, centrifuged, washed with anhydrous acetone and eventually dried, After recrystallization from acetone, crystals are obtained, melting point 132°C.

Therapeutic Function

Antirheumatic

Flammability and Explosibility

Not classified

Oxaceprol(33996-33-7)Related Product Information

• Oxaceprol
• TRANS-1-BENZOYL-4-HYDROXY-L-PROLINE METHYL ESTER
• N-Tetradecanoyl-4-hydroxy-L-proline
• TRANS-1-BENZOYL-4-HYDROXY-L-PROLINE
• Dipalmitoyl hydroxyproline
• N-Acetyl-L-Hydroxyproline
• L-Hydroxyproline
• L-Proline
• 1-(4-FLUOROBENZOYL)-4-HYDROXY-2-PYRROLIDINECARBOXYLIC ACID
• H-GLY-ALA-HYP-OH
• H-GLY-PRO-HYP-OH
• H-PRO-HYP-OH
• H-GLY-HYP-OH
• GLY-PRO-HYDROXY-PRO ACETATE SALT
• 1-(2-FURYLCARBONYL)-4-HYDROXY-2-PYRROLIDINECARBOXYLIC ACID
• METHYL 1-(4-FLUOROBENZOYL)-4-HYDROXY-2-PYRROLIDINECARBOXYLATE
• Z-PRO-HYP-OH
• O-acetyl-L-hydroxyproline homopolymer,POLY-O-ACETYL-L-HYDROXYPROLINE)