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L-Tryptophan

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Identification
Molecular formula
C11H12N2O2
CAS number
73-22-3
IUPAC name
(2S)-2-amino-3-(1H-indol-3-yl)propanoic acid
State
State
L-Tryptophan is a solid under standard conditions (25°C, 1 atm).
Melting point (Celsius)
289.00
Melting point (Kelvin)
562.00
Boiling point (Celsius)
282.00
Boiling point (Kelvin)
555.00
General information
Molecular weight
204.23g/mol
Molar mass
204.2290g/mol
Density
1.3400g/cm3
Appearence

L-Tryptophan is a white crystalline powder. It is known for its distinct appearance, typical of many amino acids.

Comment on solubility

Solubility of (2S)-2-amino-3-(1H-indol-3-yl)propanoic acid

The solubility of (2S)-2-amino-3-(1H-indol-3-yl)propanoic acid, or C11H12N2O2, can be influenced by several factors that are intrinsic to its chemical structure:

  • Polarity: The presence of amine and carboxylic acid functional groups enhances polar interactions, making the compound moderately soluble in water.
  • Hydrogen Bonding: The ability to form hydrogen bonds with water molecules significantly aids in dissolving this compound.
  • pH Sensitivity: The solubility can vary with pH levels since the ionization state of the carboxylic acid can change, affecting solubility.
  • Temperature: Higher temperatures generally increase solubility for many compounds, and (2S)-2-amino-3-(1H-indol-3-yl)propanoic acid is likely no exception.

In summary, the solubility of (2S)-2-amino-3-(1H-indol-3-yl)propanoic acid is affected by its polar nature and functional groups, which facilitate interactions with solvents, particularly in aqueous solutions. Understanding these properties is crucial, especially in applications such as pharmaceuticals where the solubility profile can influence drug formulation and bioavailability.

Interesting facts

Interesting Facts About (2S)-2-amino-3-(1H-indol-3-yl)propanoic acid

(2S)-2-amino-3-(1H-indol-3-yl)propanoic acid, commonly known as tryptophan, is a fascinating amino acid that plays a pivotal role in human biology. As an essential amino acid, it cannot be synthesized by the human body and must be obtained through diet. Here are some intriguing aspects of this compound:

  • Building Block of Proteins: Tryptophan is vital for protein synthesis, serving as a building block for numerous proteins in the body.
  • Precursor to Serotonin: This amino acid is a precursor to serotonin, a neurotransmitter known to regulate mood, sleep, and appetite. Low levels of serotonin are often linked to depression.
  • Influence on Melatonin Production: Tryptophan is also a precursor for melatonin, the hormone responsible for regulating sleep cycles. Higher tryptophan levels can lead to improved sleep quality.
  • Rich Food Sources: Foods high in tryptophan include turkey, chicken, fish, nuts, and dairy products. This is often why turkey is associated with post-Thanksgiving drowsiness!
  • Role in Immune Function: Tryptophan has been found to play a role in immune response, influencing the production of various immune cells.

Furthermore, tryptophan can contribute to a feeling of well-being and relaxation, which makes it a popular supplement for those looking to improve mood or reduce anxiety. Scientists continue to explore its potential therapeutic effects, demonstrating the compound's importance beyond just its role as a basic building block for proteins.

In summary, (2S)-2-amino-3-(1H-indol-3-yl)propanoic acid is not only an essential amino acid but also a crucial player in numerous biochemical pathways, highlighting the interconnectedness of nutrition, mental health, and physiological well-being.

Synonyms
L-tryptophan
tryptophan
73-22-3
h-Trp-oh
L-Tryptophane
Tryptophane
(S)-Tryptophan
trofan
tryptacin
Ardeytropin
Optimax
(2S)-2-amino-3-(1H-indol-3-yl)propanoic acid
Pacitron
Indole-3-alanine
Kalma
L-beta-3-Indolylalanine
L-Tryptofan
L-Trp
L-(-)-Tryptophan
triptofano
3-Indol-3-ylalanine
(-)-Tryptophan
Tryptophan (H-3)
1-beta-3-Indolylalanine
Tryptophanum
Tryptan
Lyphan
1beta-3-Indolylalanine
Tryptophan (VAN)
Triptofano [Spanish]
Tryptophanum [Latin]
1H-Indole-3-alanine
Tryptophan, L-
2-Amino-3-indolylpropanoic acid
L(-)-Tryptophan
(L)-TRYPTOPHAN
(S)-alpha-Amino-1H-indole-3-propanoic acid
Tryptophane [French]
alpha'-Amino-3-indolepropionic acid
Tryptophan [USAN:INN]
L-alpha-amino-3-indolepropionic acid
EH 121
L-alpha-Aminoindole-3-propionic acid
trp
Sedanoct
(S)-alpha-Aminoindole-3-propionic acid
Trytophan-
CCRIS 617
1H-Indole-3-alanine (VAN)
HSDB 4142
Alanine, 3-indol-3-yl-
NCI-C01729
(S)-2-Amino-3-(3-indolyl)propionic acid
AI3-18478
L-Alanine, 3-(1H-indol-3-yl)-
1H-Indole-3-alanine, (S)-
alpha-Amino-3-indolepropionic acid, L-
CHEBI:16828
(S)-alpha-amino-beta-(3-indolyl)-propionic acid
UNII-8DUH1N11BX
EINECS 200-795-6
8DUH1N11BX
MFCD00064340
NSC 13119
Indole-3-propionic acid, alpha-amino-
1H-Indole-3-propanoic acid, alpha-amino-, (S)-
Propionic acid, 2-amino-3-indol-3-yl-
DTXSID5021419
Lopac-T-0254
NSC-13119
Tryptophan ((-),l,s)
(S)-alpha-Amino-beta-indolepropionic acid
CHEMBL54976
DTXCID801419
EC 200-795-6
(S)-2-Amino-3-(1H-indol-3-yl)propanoic acid
Tryptophanum (Latin)
TRYPTOPHAN (II)
TRYPTOPHAN [II]
TRYPTOPHAN (MART.)
TRYPTOPHAN [MART.]
Htrp
l-b-3-Indolylalanine
TRYPTOPHAN (EP MONOGRAPH)
TRYPTOPHAN [EP MONOGRAPH]
Levotryptophan
TRYPTOPHAN (USP MONOGRAPH)
TRYPTOPHAN [USP MONOGRAPH]
beta-3-indolylalanine
CAS-73-22-3
Propionic acid, 2-amino-3-indol-3-yl
L-Tryptophan (9CI)
Tryptophan (USP/INN)
(S)-a-Amino-b-indolepropionic acid
N-ACETYLTRYPTOPHAN IMPURITY A (EP IMPURITY)
N-ACETYLTRYPTOPHAN IMPURITY A [EP IMPURITY]
(S)-a-Aminoindole-3-propionic acid
Alanine, 3-indol-3-yl
L-Tryptophan-13C11,15N2
(2S)-2-amino-3-(1H-indol-3-yl)propanoate
trytophan
(S)-a-Amino-1H-indole-3-propanoic acid
TRP-01
L-Trytophan
1qaw
80206-30-0
L-Tryptophan,(S)
L-Trp-OH
Tryptophan [WHO-DD]
2a4m
TRYPTOPHAN [MI]
L-Tryptophan (JP18)
L-Tryptophan (standard)
TRYPTOPHAN [INN]
S(-)-1-alpha-Aminoindole-3-propionic acid
TRYPTOPHAN [HSDB]
TRYPTOPHAN [USAN]
Tryptophan (L-Tryptophan)
TRYPTOPHAN [VANDF]
Tryptophan, L- (8CI)
bmse000050
bmse000868
bmse001017
Epitope ID:136043
T 0254
L-TRYPTOPHAN [FCC]
L-TRYPTOPHAN [JAN]
SCHEMBL7328
2-Amino-3-indolylpropanoate
(S)-(-)-2-Amino-3-(3-indolyl)propionic Acid
(S)-1H-Indole-3-alanine
Lopac0_001183
GTPL717
L-TRYPTOPHAN [VANDF]
MLS001056750
DivK1c_000457
L-TRYPTOPHAN [USP-RS]
(s)-a-amino-b-indolepropionate
151A3008-4CFE-40C9-AC0B-467EF0CB50EA
(S)-a-Aminoindole-3-propionate
BDBM21974
HMS501G19
HY-N0623R
KBio1_000457
MSK1418
N06AX02
3-(1H-indol-3-yl)-L-Alanine
L-a-Amino-3-indolepropionic acid
NINDS_000457
alpha-Aminoindole-3-propionic acid
HMS3263N07
Pharmakon1600-01500600
202406-50-6
HY-N0623
STR02722
(S)-alpha-Aminoindole-3-propionate
Tox21_201246
Tox21_300359
Tox21_501183
NSC757373
s3987
(s)-alpha-amino-beta-indolepropionate
L-Tryptophan, Vetec(TM), 98.5%
(S)-a-Amino-1H-indole-3-propanoate
AKOS015854052
Indoe-3-propionic acid, alpha-amino-
CCG-205257
CS-W020011
DB00150
ET06029
LP01183
NSC-757373
SDCCGSBI-0051150.P002
IDI1_000457
NCGC00015994-01
NCGC00094437-01
NCGC00094437-02
NCGC00094437-03
NCGC00094437-04
NCGC00094437-08
NCGC00254424-01
NCGC00258798-01
NCGC00261868-01
(S)-alpha-Amino-1H-indole-3-propanoate
AC-17050
BP-13286
IS_TRYPTOPHAN-2,4,5,6,7-D5
SMR000326686
TS-04426
propanoic acid, 2-amino-3-(3-indolyl)-
DB-029986
L-Tryptophan, BioUltra, >=99.5% (NT)
EU-0101183
NS00003513
T0541
(S)-Tryptophan 1H-Indole-3-alanine, (S)-
EN300-52634
C00078
D00020
L-.ALPHA.-AMINO-3-INDOLEPROPIONIC ACID
L-Tryptophan, reagent grade, >=98% (HPLC)
M02943
P16427
AB00373874_05
L-Tryptophan, Vetec(TM) reagent grade, >=98%
(S)-2-amino-3-(1H-Indol-3-yl)-propionic acid
L-Tryptophan, Cell Culture Reagent (H-L-Trp-OH)
Q181003
SR-01000075590
SR-01000075590-1
BRD-K83776863-001-05-5
BRD-K83776863-001-08-9
F0001-2364
Z756440056
1H-INDOLE-3-PROPANOIC ACID, .ALPHA.-AMINO-, (S)-
L-Tryptophan, certified reference material, TraceCERT(R)
Tryptophan, European Pharmacopoeia (EP) Reference Standard
L-Tryptophan, United States Pharmacopeia (USP) Reference Standard
200-795-6
L-Tryptophan, from non-animal source, meets EP, JP, USP testing specifications, suitable for cell culture, 99.0-101.0%