2,3,4,9-TETRAHYDRO-1H-BETA-CARBOLINE-3-CARBOXYLIC ACID Chemical Properties

Melting point:

289 °C (dec.)(lit.)

Boiling point:

485.0±45.0 °C(Predicted)

Density 

1.377±0.06 g/cm3(Predicted)

storage temp. 

under inert gas (nitrogen or Argon) at 2–8 °C

pka

2.28±0.20(Predicted)

Appearance

Light brown to brown Solid

InChI

InChI=1S/C12H12N2O2/c15-12(16)10-5-8-7-3-1-2-4-9(7)14-11(8)6-13-10/h1-4,10,13-14H,5-6H2,(H,15,16)

InChIKey

FSNCEEGOMTYXKY-UHFFFAOYSA-N

SMILES

N1C2=C(C=CC=C2)C2CC(C(O)=O)NCC1=2

Safety Information

Hazard Codes 

Xi

Risk Statements 

36/37/38

Safety Statements 

26-36

WGK Germany 

3

2,3,4,9-TETRAHYDRO-1H-BETA-CARBOLINE-3-CARBOXYLIC ACID Usage And Synthesis

Definition

ChEBI: A member of the class of beta-carbolines that is 1,2,3,4-tetrahydro-beta-carboline substituted at position 3 by a carboxy group.

Synthesis

The general procedure for the synthesis of 2,3,4,9-tetrahydro-1H-pyrido[3,4-b]indole-3-carboxylic acid from formaldehyde and L-tryptophan was as follows: first, 1-propanesulfonic acid (817 mg, 4 mmol) was mixed with 2.5 M NaOH solution (1.6 mL), and the mixture was stirred at room temperature until it became clear. Subsequently, 37% formalin (4.87 mL) was added to the mixture. The reaction mixture was stirred at room temperature for 2 hours and then refluxed for 3 hours. Upon completion of the reaction, it was neutralized with 2 M HCl solution to pH 5. The precipitate precipitated was filtered, washed sequentially with water and methanol and finally dried under vacuum to afford the target product 2,3,4,9-tetrahydro-1H-pyrido[3,4-b]indole-3-carboxylic acid. The yield of this step was 99% and the product was a colorless solid with a melting point of 302.2-304.6 °C. Mass spectrometry (FAB) analysis showed m/z 217 (M+1, 100%).

References

[1] European Journal of Medicinal Chemistry, 2011, vol. 46, # 2, p. 636 - 646
[2] Acta chemica Scandinavica (Copenhagen, Denmark : 1989), 1994, vol. 48, # 5, p. 434 - 438
[3] Patent: CN106432235, 2017, A. Location in patent: Paragraph 0217; 0218
[4] Patent: US2013/178629, 2013, A1. Location in patent: Paragraph 0109
[5] Molecules, 2010, vol. 15, # 11, p. 7775 - 7791

2,3,4,9-TETRAHYDRO-1H-BETA-CARBOLINE-3-CARBOXYLIC ACID(6052-68-2)Related Product Information

• 2-(3-INDOLYLMETHYL)-L-TRYPTOPHAN
• 2-Hydroxy-DL-tryptophan
• Tryptophan EP Impurity L
• Tryptophan EP Impurity F
• PEAK E
• Tryptophan EP Impurity D
• L-KYNURENINE
• Tryptophan EP Impurity J
• N'-formyl-L-Kynurenine
• Dioxindolyl-L-alanine
• 1-METHYL-2,3,4,9-TETRAHYDRO-1H-BETA-CARBOLINE-3-CARBOXYLIC ACID
• 2,3,4,9-TETRAHYDRO-1H-BETA-CARBOLINE-3-CARBOXYLIC ACID
• L-1,2,3,4-TETRAHYDRONORHARMAN-3-CARBOXYLIC ACID
• 1-PYRIDIN-3-YL-2,3,4,9-TETRAHYDRO-1H-BETA-CARBOLINE-3-CARBOXYLIC ACID
• 1-PROPYL-2,3,4,9-TETRAHYDRO-1H-BETA-CARBOLINE-3-CARBOXYLIC ACID
• 1,1-DIMETHYL-2,3,4,9-TETRAHYDRO-1H-BETA-CARBOLINE-3-CARBOXYLIC ACID
• (1S,3S)-1-ETHYL-2,3,4,9-TETRAHYDRO-1H-PYRIDO[3,4-B]INDOLE-3-CARBOXYLIC ACID
• 1-ISOBUTYL-2,3,4,9-TETRAHYDRO-1H-BETA-CARBOLINE-3-CARBOXYLIC ACID