Tryptophan

C₁₁H₁₂N₂O₂

IUPAC: (S)-2-Amino-3-(1H-indol-3-yl)propanoic acid

CAS: 73-22-3

Overview

Tryptophan is an essential amino acid that the body cannot synthesize. It is the biosynthetic precursor to serotonin (the 'happy molecule') and melatonin (the 'sleep hormone'). It is the least abundant amino acid in most proteins.

Composition

Element Symbol Atoms Atomic Mass
Hydrogen H 12 1.0080
Carbon C 11 12.0110
Nitrogen N 2 14.0070
Oxygen O 2 15.9990

Elemental Composition

H
Hydrogen ×12
5.9%
C
Carbon ×11
64.7%
N
Nitrogen ×2
13.7%
O
Oxygen ×2
15.7%

Uses

  • • Serotonin and melatonin precursor
  • • Dietary supplement (sleep aid)
  • • Animal feed additive
  • • Niacin (vitamin B3) precursor

Fun Facts

  • ✦ Turkey contains tryptophan, but the post-Thanksgiving drowsiness is more likely from overeating than tryptophan

Safety

  • ⚠ Generally safe at dietary levels
  • ⚠ High-dose supplements may interact with SSRI medications

Structure

SMILES

C1=CC=C2C(=C1)C(=CN2)CC(C(=O)O)N

Properties

Type
organic
State
solid
Molar Mass
204.23 g/mol
Density
1.3400 g/cm³
Melting Point
289.0 °C
Solubility
11.4 g/L at 25°C

Molecular Descriptors

Exact Mass
204.0899
XLogP
-1.1
TPSA
79.1 Ų
H-Bond Donors
3
H-Bond Acceptors
3
Rotatable Bonds
3
Heavy Atoms
15
Complexity
245.0

Also Known As

L-Tryptophan Trp W

Related Compounds

1,2-Dichloroethane

C₂H₄Cl₂

1,3-Butadiene

C₄H₆

1,4-Dioxane

C₄H₈O₂

1-Butanol

C₄H₁₀O

2-Propanol

C₃H₈O

Acetaldehyde

CH₃CHO

Acetamide

C₂H₅NO

Acetic Anhydride

C₄H₆O₃

Acetone

(CH₃)₂CO

Acetonitrile

C₂H₃N

Frequently Asked Questions

What is Tryptophan?
Tryptophan (C₁₁H₁₂N₂O₂) is a organic compound with the IUPAC name (S)-2-Amino-3-(1H-indol-3-yl)propanoic acid.
What is the molecular weight of Tryptophan?
Tryptophan has a molar mass of 204.229 g/mol.
What state is Tryptophan at room temperature?
Tryptophan is a solid at room temperature.
Is Tryptophan organic or inorganic?
Tryptophan is classified as an organic compound.
What elements make up Tryptophan?
Tryptophan (C₁₁H₁₂N₂O₂) is composed of Hydrogen (H), Carbon (C), Nitrogen (N), Oxygen (O).