D-1,2,3,4-Tetrahydroisoquinoline-3-carboxylic acid Chemical Properties

Melting point:

320-323 °C (decomp)

Boiling point:

372.0±42.0 °C(Predicted)

Density 

1.225±0.06 g/cm3(Predicted)

storage temp. 

Keep in dark place,Inert atmosphere,Room temperature

solubility 

Aqueous Acid (Slightly), Aqueous Base (Sparingly, Sonicated)

form 

Crystalline Powder

pka

2.21±0.20(Predicted)

color 

White

InChI

InChI=1S/C10H11NO2/c12-10(13)9-5-7-3-1-2-4-8(7)6-11-9/h1-4,9,11H,5-6H2,(H,12,13)/t9-/m1/s1

InChIKey

BWKMGYQJPOAASG-SECBINFHSA-N

SMILES

C1C2=C(C=CC=C2)C[C@H](C(O)=O)N1

CAS DataBase Reference

103733-65-9(CAS DataBase Reference)

Safety Information

Hazard Codes 

Xi

Risk Statements 

36/37/38

Safety Statements 

26-36

WGK Germany 

3

HS Code 

29334900

MSDS

• Language:English Provider:SigmaAldrich

D-1,2,3,4-Tetrahydroisoquinoline-3-carboxylic acid Usage And Synthesis

Description

D-1,2,3,4-Tetrahydroisoquinoline-3-carboxylic acid ((3R)-1,2,3,4-Tetrahydroisoquinoline-3-carboxylic acid) is a magnetic, neutral compound. It is used as a pharmacological study to investigate the reaction mechanism and kinetics of the deuteration process. The asymmetric synthesis of D-1,2,3,4-Tetrahydroisoquinoline-3-carboxylic acid has been investigated using vinylene chloride and hydantoin as reactants. There are various parameters that affect the kinetics of this reaction such as solvent type and temperature. The nitric oxide synthase inhibitor activity of D-1,2,3,4-Tetrahydroisoquinoline-3-carboxylic acid has been studied in vitro. Results have shown that it inhibits nitric oxide synthase by binding to the heme iron of the enzyme and preventing the conversion of arginine

Chemical Properties

White solid

Uses

(R)-1,2,3,4-Tetrahydroisoquinoline-3-carboxylic Acid, is an amino acid building block used in peptide synthesis. With a growing peptide drug market the fast, reliable synthesis of peptides is of great importance.

Definition

ChEBI: D-1,2,3,4-Tetrahydroisoquinoline-3-carboxylic acid is a member of isoquinolines.

Synthesis

General procedure for the synthesis of (R)-1,2,3,4-tetrahydroisoquinoline-3-carboxylic acid from formaldehyde and D-phenylalanine: 1. Preparation of (3R)-1,2,3,4-tetrahydroisoquinoline-3-carboxylic acid: D-phenylalanine (50 g, 0.3 mol), concentrated hydrochloric acid (386 mL), and 37% wt formalin (113.7 mL) were mixed, and the reaction was carried out for 4 h at 95 °C with vigorous stirring. Upon completion of the reaction, the mixture was cooled to room temperature and stirring was continued for 2 hours. The reaction mixture was filtered and the precipitate was washed with cold water to afford (3R)-1,2,3,4-tetrahydroisoquinoline-3-carboxylic acid (25 g, 42% yield) in white solid form. 2. Esterification reaction: benzyl alcohol (64 g) and p-toluenesulfonic acid (26.9 g) were added to the above product, and the reaction was carried out under reflux in a Dean-Stark apparatus with benzene (400 mL) as solvent. After completion of the reaction, the solvent was removed in vacuum and the crude product was ground with ether to obtain a solid, which was subsequently recrystallized with water and methanol to give (R)-1,2,3,4-tetrahydroisoquinoline-3-carboxylic acid (28 g, 35% yield) in white solid form.

References

[1] MedChemComm, 2014, vol. 5, # 9, p. 1381 - 1383
[2] Journal of Medicinal Chemistry, 1988, vol. 31, # 11, p. 2092 - 2097
[3] Patent: WO2004/72086, 2004, A2. Location in patent: Page 182
[4] Journal of Medicinal Chemistry, 2010, vol. 53, # 15, p. 5727 - 5737

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