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| | BZ-TYR-4-ABZ-OH Basic information |
| Product Name: | BZ-TYR-4-ABZ-OH | | Synonyms: | 4-[[(S)-2-(Benzoylamino)-3-(4-hydroxyphenyl)-1-oxopropyl]amino]benzoic acid;BTPABA,PFT;(s)-4-((2-(benzoylamino)-3-(4-hydroxyphenyl)-1-oxopropyl)amino)benzoicacid;(s)-p-(alpha-benzamido-p-hydroxyhydrocinnamamido)benzoicacid;4-((2-(benzoylamino)-3-(4-hydroxyphenyl)-1-oxopropyl)amino)-benzoicaci(s);4-((2-(benzoylamino)-3-(4-hydroxyphenyl)-1-oxopropyl)amino)benzoicacid;benzoyltyrosyl-p-aminobenzoicacid;BentiroMide, BTPABA | | CAS: | 37106-97-1 | | MF: | C23H20N2O5 | | MW: | 404.42 | | EINECS: | 253-349-8 | | Product Categories: | | | Mol File: | 37106-97-1.mol |  |
| | BZ-TYR-4-ABZ-OH Chemical Properties |
| 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) | | pka | 4.27±0.10(Predicted) |
| | BZ-TYR-4-ABZ-OH Usage And Synthesis |
| 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) |
| | BZ-TYR-4-ABZ-OH Preparation Products And Raw materials |
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