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| Other Sizes |
| Targets |
The primary targets of DL-Tryptophan include serotonin transporters and serotonin synthesis pathways. As an essential amino acid precursor, it is converted to serotonin, melatonin, and vitamin B3. DL-Tryptophan containing dipeptides selectively inhibit the C-domain of angiotensin-converting enzyme (ACE), providing a natural prevention for hypertension. The compound's aromatic indole ring structure influences protein synthesis and enzyme-substrate interactions.
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| ln Vitro |
In vitro, DL-Tryptophan is studied for its role as an essential amino acid precursor in serotonin, melatonin, and vitamin B3 synthesis. It is used in cell culture media for protein synthesis studies. DL-Tryptophan containing dipeptides demonstrate selective inhibition of the C-domain, which is relevant for hypertension research. The compound's dual stereochemistry provides versatility in synthetic and structural biochemistry. These in vitro activities support its use in neuroscience, nutrition, and drug development.
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| ln Vivo |
In vivo, DL-Tryptophan is an essential amino acid required for serotonin production, which is crucial for brain functioning. It is a precursor for melatonin and vitamin B3. DL-Tryptophan containing dipeptides serve as functional food ingredients for natural prevention of hypertension. The compound is used in nutritional studies and as a dietary supplement. Its role in serotonin synthesis makes it relevant for research on mood, sleep, and neurological disorders.
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| Enzyme Assay |
In vitro enzyme assays for DL-Tryptophan include studies on tryptophan hydroxylase and serotonin synthesis pathways. The compound is incubated with enzyme preparations at concentrations ranging from 0.1-1000 μM, and serotonin production is measured by HPLC or ELISA. ACE inhibition assays using DL-Tryptophan containing dipeptides are conducted with ACE enzyme and chromogenic substrates. Binding to serotonin transporters can be assessed using radioligand binding assays. All assays include appropriate controls and reference compounds.
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| Cell Assay |
In vitro cell-based assays for DL-Tryptophan are conducted using neuronal cell lines or serotonin-producing cells. Cells are treated with compound concentrations ranging from 0.1-1000 μM for 24-72 hours. Serotonin and melatonin levels are measured by ELISA or HPLC. Cell viability is assessed using MTT assays. For hypertension research, vascular smooth muscle cells may be used to assess ACE inhibition effects. Experiments include vehicle controls and positive controls (e.g., known serotonin precursors).
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| Animal Protocol |
In vivo animal studies with DL-Tryptophan are conducted in rodent models for nutrition, neuroscience, and hypertension research. The compound is administered via dietary supplementation or oral gavage at doses ranging from 10-200 mg/kg. Serotonin and melatonin levels are measured in brain tissue. Blood pressure is monitored for hypertension studies. Behavioral tests (e.g., forced swim test, elevated plus maze) assess mood and anxiety-related effects. Each group consists of 6-10 animals with appropriate controls.
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| ADME/Pharmacokinetics |
Pharmacokinetic properties of DL-Tryptophan include its absorption from the gastrointestinal tract following dietary intake. As an amino acid (MW 204.23), it is transported across the blood-brain barrier via the large neutral amino acid transporter. The compound is metabolized through the kynurenine pathway and serotonin synthesis pathway. Elimination occurs via metabolism and renal excretion. Its pharmacokinetics are influenced by dietary intake, metabolic rate, and transporter activity.
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| Additional Infomation |
Tryptophan is an α-amino acid, a derivative of alanine with an indole-3-yl substituent at the 3-position. It is a metabolite of the large flea (Daphnia magna). It is an α-amino acid, an aminoalkylindole, a polar amino acid, and an aromatic amino acid. It contains a 1H-indole-3-ylmethyl group. It is the conjugate base of tryptophan ononium. It is the conjugate acid of tryptophan acid. It is the zwitterion tautomer of tryptophan. DL-tryptophan has been reported in Smallanthus sonchifolius, Drosophila melanogaster, and other organisms with relevant data. See also: Tryptophan (note moved to).
DL-Tryptophan is an essential amino acid and precursor for serotonin, melatonin, and vitamin B3. It is crucial for brain functioning due to its role in serotonin production. DL-Tryptophan containing dipeptides show potential as functional foods for hypertension prevention through selective C-domain inhibition. The compound is used in research on neuroscience, nutrition, and cardiovascular health. Available as a dietary supplement and research chemical. |
| Molecular Formula |
C₁₁H₁₂N₂O₂
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|---|---|
| Molecular Weight |
204.23
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| Exact Mass |
204.089
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| CAS # |
54-12-6
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| Related CAS # |
DL-Tryptophan-d3;340257-61-6;DL-Tryptophan-d8;1233395-85-1
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| PubChem CID |
1148
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| Appearance |
White to light yellow solid powder
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| Density |
1.4±0.1 g/cm3
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| Boiling Point |
447.9±35.0 °C at 760 mmHg
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| Melting Point |
554 to 558 °F (Decomposes) (NTP, 1992)
; 282 °C (decomposes)
; 230 °C
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| Flash Point |
224.7±25.9 °C
|
| Vapour Pressure |
0.0±1.1 mmHg at 25°C
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| Index of Refraction |
1.698
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| LogP |
1.04
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| Hydrogen Bond Donor Count |
3
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| Hydrogen Bond Acceptor Count |
3
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| Rotatable Bond Count |
3
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| Heavy Atom Count |
15
|
| Complexity |
245
|
| Defined Atom Stereocenter Count |
0
|
| SMILES |
C1=CC=C2C(=C1)C(=CN2)C[C@@H](C(=O)O)N
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| InChi Key |
QIVBCDIJIAJPQS-UHFFFAOYSA-N
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| InChi Code |
InChI=1S/C11H12N2O2/c12-9(11(14)15)5-7-6-13-10-4-2-1-3-8(7)10/h1-4,6,9,13H,5,12H2,(H,14,15)
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| Chemical Name |
2-amino-3-(1H-indol-3-yl)propanoic acid
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| Synonyms |
DLTryptophan; DL Tryptophan
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| HS Tariff Code |
2934.99.9001
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| Storage |
Powder -20°C 3 years 4°C 2 years In solvent -80°C 6 months -20°C 1 month |
| Shipping Condition |
Room temperature (This product is stable at ambient temperature for a few days during ordinary shipping and time spent in Customs)
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| Solubility (In Vitro) |
DMSO : ~3.85 mg/mL (~18.85 mM)
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|---|---|
| Solubility (In Vivo) |
Note: Listed below are some common formulations that may be used to formulate products with low water solubility (e.g. < 1 mg/mL), you may test these formulations using a minute amount of products to avoid loss of samples.
Injection Formulations
Injection Formulation 1: DMSO : Tween 80： Saline = 10 : 5 : 85 (i.e. 100 μL DMSO stock solution → 50 μL Tween 80 → 850 μL Saline)(e.g. IP/IV/IM/SC) *Preparation of saline: Dissolve 0.9 g of sodium chloride in 100 mL ddH ₂ O to obtain a clear solution. Injection Formulation 2: DMSO : PEG300 ：Tween 80 : Saline = 10 : 40 : 5 : 45 (i.e. 100 μL DMSO → 400 μLPEG300 → 50 μL Tween 80 → 450 μL Saline) Injection Formulation 3: DMSO : Corn oil = 10 : 90 (i.e. 100 μL DMSO → 900 μL Corn oil) Example: Take the Injection Formulation 3 (DMSO : Corn oil = 10 : 90) as an example, if 1 mL of 2.5 mg/mL working solution is to be prepared, you can take 100 μL 25 mg/mL DMSO stock solution and add to 900 μL corn oil, mix well to obtain a clear or suspension solution (2.5 mg/mL, ready for use in animals). View More
Injection Formulation 4: DMSO : 20% SBE-β-CD in saline = 10 : 90 [i.e. 100 μL DMSO → 900 μL (20% SBE-β-CD in saline)] Oral Formulations
Oral Formulation 1: Suspend in 0.5% CMC Na (carboxymethylcellulose sodium) Oral Formulation 2: Suspend in 0.5% Carboxymethyl cellulose Example: Take the Oral Formulation 1 (Suspend in 0.5% CMC Na) as an example, if 100 mL of 2.5 mg/mL working solution is to be prepared, you can first prepare 0.5% CMC Na solution by measuring 0.5 g CMC Na and dissolve it in 100 mL ddH2O to obtain a clear solution; then add 250 mg of the product to 100 mL 0.5% CMC Na solution, to make the suspension solution (2.5 mg/mL, ready for use in animals). View More
Oral Formulation 3: Dissolved in PEG400 (Please use freshly prepared in vivo formulations for optimal results.) |
| Preparing Stock Solutions | 1 mg | 5 mg | 10 mg | |
| 1 mM | 4.8964 mL | 24.4822 mL | 48.9644 mL | |
| 5 mM | 0.9793 mL | 4.8964 mL | 9.7929 mL | |
| 10 mM | 0.4896 mL | 2.4482 mL | 4.8964 mL |
*Note: Please select an appropriate solvent for the preparation of stock solution based on your experiment needs. For most products, DMSO can be used for preparing stock solutions (e.g. 5 mM, 10 mM, or 20 mM concentration); some products with high aqueous solubility may be dissolved in water directly. Solubility information is available at the above Solubility Data section. Once the stock solution is prepared, aliquot it to routine usage volumes and store at -20°C or -80°C. Avoid repeated freeze and thaw cycles.
Calculation results
Working concentration： mg/mL；
Method for preparing DMSO stock solution： mg drug pre-dissolved in μL DMSO (stock solution concentration mg/mL). Please contact us first if the concentration exceeds the DMSO solubility of the batch of drug.
Method for preparing in vivo formulation:：Take μL DMSO stock solution, next add μL PEG300, mix and clarify, next addμL Tween 80, mix and clarify, next add μL ddH2O，mix and clarify.
(1) Please be sure that the solution is clear before the addition of next solvent. Dissolution methods like vortex, ultrasound or warming and heat may be used to aid dissolving.
(2) Be sure to add the solvent(s) in order.
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