6-Hydroxy-1,2,3,4-tetrahydroisoquinoline-1-carboxylic acid

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6-Hydroxy-1,2,3,4-tetrahydroisoquinoline-1-carboxylic acid Basic information
Product Name:6-Hydroxy-1,2,3,4-tetrahydroisoquinoline-1-carboxylic acid
Synonyms:6-HYDROXY-1,2,3,4-TETRAHYDRO-ISOQUINOLINE-1-CARBOXYLIC ACID;6-Hydroxy-1,2,3,4-tetrahydroisoquinoline-16-Hydroxy-1,2,3,4-tetrahydroisoquinoline-1-carboxylic acid-carboxylic acid;6-Hydroxy-1,2,3,4-tetrahydro-sioquinoline-1-carboxylicacid;6-Hydroxy-1,2,3,4-tetrahydro-isoquinoline-1-carboxcarboxylicacid;6-Hydroxy-1,2,3,4-tetrahydro-isoquinoline-1-caeboxylic acid;6-Hydroxy-1,2,3,4-tetrahydro-isoquinoline-1-carbox;1-Isoquinolinecarboxylic acid, 1,2,3,4-tetrahydro-6-hydroxy-;6-Hydroxy-1,2,3,4-tetrahydro-isoquinoline-1-carboxylic acid, CAS 91523-50-1
CAS:91523-50-1
MF:C10H11NO3
MW:193.2
EINECS:
Product Categories:
Mol File:91523-50-1.mol
6-Hydroxy-1,2,3,4-tetrahydroisoquinoline-1-carboxylic acid Structure
6-Hydroxy-1,2,3,4-tetrahydroisoquinoline-1-carboxylic acid Chemical Properties
Boiling point 458.1±45.0 °C(Predicted)
density 1.351±0.06 g/cm3(Predicted)
storage temp. under inert gas (nitrogen or Argon) at 2–8 °C
pka2.05±0.20(Predicted)
Safety Information
Hazard Codes Xn
Risk Statements 22
MSDS Information
6-Hydroxy-1,2,3,4-tetrahydroisoquinoline-1-carboxylic acid Usage And Synthesis
Uses6-Hydroxy-1,2,3,4-tetrahydro-isoquinoline-1-carboxylic Acid is useful chemical in the studying of proline containing peptides as caspase-2 inhibitors.
Synthesis Reference(s)Journal of Medicinal Chemistry, 27, p. 1321, 1984 DOI: 10.1021/jm00376a017
Synthesis
2-(3-HYDROXYPHENYL)ETHYLAMINE

588-05-6

Glyoxylic acid

298-12-4

6-Hydroxy-1,2,3,4-tetrahydroisoquinoline-1-carboxylic acid

91523-50-1

GENERAL PROCEDURE: A solution of 2-oxoacetic acid monohydrate (2.0 g, 22 mmol) in ethanol (10 mL) was added slowly and dropwise to a denatured ethanol (70 mL) solution of 3-hydroxyphenylethylamine hydrochloride (3.08 g, 22.5 mmol) at 4 °C. Immediately after the dropwise addition, a white precipitate was observed to be generated. The ice bath was removed and the reaction mixture was stirred at room temperature for 2 hours. Upon completion of the reaction, the white solid product 6-hydroxy-1,2,3,4-tetrahydroisoquinoline-1-carboxylic acid (3.1 g, 73% yield) was collected by filtration. The product was analyzed by LC/MS (electrospray, positive ion mode) and showed m/z 194 ([M+H]+).

References[1] Journal of Medicinal Chemistry, 1984, vol. 27, # 10, p. 1321 - 1325
[2] Patent: US6649606, 2003, B1. Location in patent: Page/Page column 38
[3] Bioorganic and Medicinal Chemistry Letters, 2004, vol. 14, # 1, p. 47 - 50
[4] Bioorganic and Medicinal Chemistry Letters, 2005, vol. 15, # 7, p. 1799 - 1802
6-Hydroxy-1,2,3,4-tetrahydroisoquinoline-1-carboxylic acid Preparation Products And Raw materials
Raw materials3-HYDROXYPHENETHYLAMINE HYDROCHLORIDE-->2-(3-Hydroxyphenyl)ethylamine-->Glyoxylic acid
Preparation ProductsMethyl 6-hydroxy-1,2,3,4-tetrahydroisoquinoline-1-carboxylate
Tag:6-Hydroxy-1,2,3,4-tetrahydroisoquinoline-1-carboxylic acid(91523-50-1) Related Product Information
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