BZ-TYR-4-ABZ-OH Property

Melting point:

240-242°

alpha 

D25 +72.3° (c = 1 in DMF) (US 3801562); D25 +87° (c = 1 in DMF) (De Benneville)

Boiling point:

526.04°C (rough estimate)

Density 

1.3093 (rough estimate)

refractive index 

1.6300 (estimate)

storage temp. 

Store at RT.

solubility 

DMSO:250.0(Max Conc. mg/mL);618.17(Max Conc. mM)

form 

Solid

pka

4.27±0.10(Predicted)

color 

White to off-white

Hazard and Precautionary Statements (GHS)

BZ-TYR-4-ABZ-OH Chemical Properties,Usage,Production

Originator

PFD Oral Sol,Eisai,Japan,1980

Uses

Diagnostic aid (pancreas function determination).

Definition

ChEBI: The dipeptide obtained by condensation of N-benzoyl-L-tyrosine with 4-aminobenzoic acid. Used as a noninvasive screening test for exocrine pancreatic insufficiency and to monitor the adequacy of supplemental pancreatic t erapy, it is given by mouth: the amount of 4-aminobenzoic acid and its metabolites excreted in the urine is taken as a measure of the chymotrypsin-secreting activity of the pancreas.

Manufacturing Process

A mixture was made of L-tyrosine (18.1 g, 0.1 mol) benzoyl chloride (7.0 g, 0.05 mol) and 200 ml anhydrous THF. After stirring at reflux for 2 hours, the mixture was cooled to room temperature, and the precipitate of tyrosine hydrochloride filtered off (11 g, 46 meq. Cl-). The THF was evaporated and the residue extracted with CCl4 (3 X 100 ml at reflux, discarded) and then dissolved in ethyl acetate (200 ml) filtering off insolubles. The ethyl acetate solution was evaporated to yield 132 g solid product, MP 159°-162°C (93%). The tyrosine was recovered (8 g) by neutralization with aqueous alkali, from the hydrochloride.
A solution was made of N-benzyl-L-tyrosine (5.7 g, 20 mmols) and Nmethylmorpholine (2.04 g, 20 mmols) in 60 ml of THF, at -15°C, and to it was added ethyl chloroformate (2.08 g, 20 mmols). After 12 minutes, paminobenzoic acid (2.74 g, 20 mmols) dissolved in 25 ml of THF and 0.38 g of p-toluenesulfonic acid (2 mmols) were added, and the temperature allowed to rise to 5°C. After 2 hours and forty minutes, the mixture was poured into l liter of 0.1 N cold HCl, stirred one-half hour, filtered and dried, to give 8,7 g, MP 192°-223°C. The product was recrystallized from 90 ml methanol and 40 ml water, to give 6 g (74%) of product, N-benzoyl-L-tyrosyl-p-aminobenzoic acid, MP 240°-242°C.

brand name

Chymex (Savage).

Therapeutic Function

Diagnostic aid (pancreatic function)