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

• ChemBase ID: 36
• Molecular Formular: C11H12N2O2
• Molecular Mass: 204.22518
• Monoisotopic Mass: 204.08987763
• SMILES: OC(=O)[C@@H](N)Cc1c2c([nH]c1)cccc2
• Canonical SMILES: OC(=O)[C@H](Cc1c[nH]c2c1cccc2)N
• InChI: 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)/t9-/m0/s1
• InChIKey: QIVBCDIJIAJPQS-VIFPVBQESA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (2S)-2-amino-3-(1H-indol-3-yl)propanoic acid
• IUPAC Traditional name: L-tryptophan; L-tryptophan(.)
• Brand Name: Alti-Tryptophan; Lyphan
• Synonyms: D-2-Amino-3-indolepropionic acid; D-TRYPTOPHAN; L-2-Amino-3-indolepropionic acid; (S)-2-amino-3-(1H-indol-3-yl)propanoic acid; H-Trp-OH; (+/-)-Tryptophan; (-)-1H-Indole-3-alanine; NSC 13119; l-α-Aminoindole-3-propionic Acid; (-)-Tryptophan; L-(-)-Tryptophan; L-Tryptophane; Tryptophan; Tryptophane; alpha-Amino-beta-(3-indolyl)-propionic acid; l-a-Aminoindole-3-propionic acid; l-b-3-Indolylalanine; (S)-a-Amino-1H-indole-3-propanoic acid; (S)-a-Amino-b-indolepropionic acid; (S)-a-Aminoindole-3-propionic acid; (S)-Tryptophan; 2-Amino-3-indolylpropanoic acid; 3-Indol-3-ylalanine; L-Tryptophan; 2-Amino-3-(1H-indol-3-yl)propanoic acid; L-Tryptophan; 2-Amino-3-(1H-indol-3-yl)propanoic acid; Tryptophan; L-Trytophane; Indole-3-Alanine; alpha-Amino-3-Indoleproprionic Acid; L-TRYPTOPHAN, U.S.P.; (S)-2-Amino-3-(3-indolyl)propionic acid; L-α-Amino-3-indolepropionic acid; L-色胺酸; (S)-2-氨基-3-(3-吲哚基)丙酸; L-α-氨基-3-吲哚丙酸; L-色氨酸

Database IDs

• CAS Number: 153-94-6; 73-22-3
• EC Number: 205-819-9; 200-795-6
• MDL Number: MFCD00064340
• Beilstein Number: 86197
• Merck Index: 149797
• PubChem SID: 160963499; 24900200; 24889916; 24900575; 24278135; 46508329
• PubChem CID: 6305
• CHEBI ID: 27897
• ATC CODE: N06AX02
• CHEMBL: 54976
• Chemspider ID: 6066
• DrugBank ID: DB00150
• IUPHAR ligand ID: 717
• KEGG ID: D00020
• Unique Ingredient Identifier: 8DUH1N11BX
• Wikipedia Title: Tryptophan

CALCULATED PROPERTIES

JChem

• Acid pKa: 2.5439286
• H Acceptors: 3
• H Donor: 3
• LogD (pH = 5.5): -1.0856168
• LogD (pH = 7.4): -1.0892947
• Log P: -1.085457
• Molar Refractivity: 56.2028 cm^3
• Polarizability: 23.092001 Å^3
• Polar Surface Area: 79.11 Å^2
• Rotatable Bonds: 3
• Lipinski's Rule of Five: true

ALOGPS 2.1

• Log P: -1.1
• LOG S: -2.18
• Solubility (Water): 1.36e+00 g/l

PROPERTIES

Physical Property

• Solubility: 0.5 M HCl: soluble0.1 g/mL at 20 °C, clear, colorless to faintly yellow; 1 M HCl: soluble10 mg/mL; Soluble; Soluble in hot alcohol, alkali hydroxides; insoluble in chloroform.; Soluble: 0.23 g/L at 0 °C,; 11.4 g/L at 25 °C,; 17.1 g/L at 50 °C,; 27.95 g/L at 75 °C in water; Water
• Apperance: powder; White Solid
• Melting Point: >246°C (dec.); 280°C 285°C; 280-285 °C (dec.)(lit.); 289°C
• Optical Rotation: [α]20/D -31.5±1°, c = 1% in H2O; [α]20/D -31.5°, c = 1 in H2O; -31 (c=1 in water)
• Hydrophobicity(logP): -1.3
• pKa: 2.38 (carboxyl), 9.39 (amino)

Safety Information

• Storage Condition: Refrigerator; Room Temperature (15-30°C); Room Temperature (15-30°C), Protect from light
• RTECS: YN6129000; YN6130000
• German water hazard class: 1
• TSCA Listed: 是
• Personal Protective Equipment: Eyeshields, Gloves, type N95 (US), type P1 (EN143) respirator filter

Pharmacology Properties

• Gene Information: human ... TDO2(6999), TPH1(7166), TPH2(121278)

Product Information

• Purity: ≥99%; ≥98% (TLC); ≥98.5%; ≥99.5% (NT); 97%; 98%; 99%; 99.0-101.0%
• Grade: certified reference material; EP; JP; reagent grade; TraceCERT®; USP
• Optical Purity: ee: 99% (GLC)
• Suitability: meets EP, JP, USP testing specifications; suitable for cell culture; suitable for manufacturing use
• Ignition Residue: ≤0.1%
• Impurities: endotoxin, tested; insoluble matter, passes filter test
• Cation Traces: Al: ≤5 mg/kg; As: ≤0.1 mg/kg; Ba: ≤5 mg/kg; Bi: ≤5 mg/kg; Ca: ≤10 mg/kg; Cd: ≤5 mg/kg; Co: ≤5 mg/kg; Cr: ≤5 mg/kg; Cu: ≤5 mg/kg; Fe: ≤5 mg/kg; K: ≤50 mg/kg; Li: ≤5 mg/kg; Mg: ≤5 mg/kg; Mn: ≤5 mg/kg; Mo: ≤5 mg/kg; Na: ≤50 mg/kg; Ni: ≤5 mg/kg; Pb: ≤5 mg/kg; Sr: ≤5 mg/kg; Zn: ≤5 mg/kg
• Antion Traces: chloride (Cl-): ≤50 mg/kg; sulfate (SO42-): ≤50 mg/kg
• Biological Source: from non-animal source
• Loss on Drying: ≤0.1% loss on drying, 20 °C (HV)
• Quality Level: GMP-COMPENDIA
• Product Line: BioUltra
• abs.: absorption0.5M/326 nm, 0.5 M HCl cut-off
• Empirical Formula (Hill Notation): C11H12N2O2
• Classification: Genuine Natural Compounds

DETAILS

MP Biomedicals - 02103151

Purity: 99+%
Crystalline

MP Biomedicals - 02103144

Crystalline
Purity: 99%

MP Biomedicals - 02199561

White powder

MP Biomedicals - 02194758

Cell Culture Reagent
Purity: 99+%
Crystalline

DrugBank - DB00150

• Drug Groups: approved; nutraceutical
• Description: An essential amino acid that is necessary for normal growth in infants and for nitrogen balance in adults. It is a precursor of indole alkaloids in plants. It is a precursor of serotonin (hence its use as an antidepressant and sleep aid). It can be a precursor to niacin, albeit inefficiently, in mammals. [PubChem]
• Indication: Tryptophan may be useful in increasing serotonin production, promoting healthy sleep, managing depression by enhancing mental and emotional well-being, managing pain tolerance, and managing weight.
• Pharmacology: Tryptophan is critical for the production of the body's proteins, enzymes and muscle tissue. It is also essential for the production of niacin, the synthesis of the neurotransmitter serotonin and melatonin. Tryptophan supplements can be used as natural relaxants to help relieve insomnia. Tryptophan can also reduce anxiety and depression and has been shown to reduce the intensity of migraine headaches. Other promising indications include the relief of chronic pain, reduction of impulsivity or mania and the treatment of obsessive or compulsive disorders. Tryptophan also appears to help the immune system and can reduce the risk of cardiac spasms. Tryptophan deficiencies may lead to coronary artery spasms. Tryptophan is used as an essential nutrient in infant formulas and intravenous feeding. Tryptophan is marketed as a prescription drug (Tryptan) for those who do not seem to respond well to conventional antidepressants. It may also be used to treat those afflicted with seasonal affective disorder (a winter-onset depression). Tryptopan serves as the precursor for the synthesis of serotonin (5-hydroxytryptamine, 5-HT) and melatonin (N-acetyl-5-methoxytryptamine).
• Toxicity: Oral rat LD₅₀: > 16 gm/kg. Investigated as a tumorigen, mutagen, reproductive effector. Symptoms of overdose include agitation, confusion, diarrhea, fever, overactive reflexes, poor coordination, restlessness, shivering, sweating, talking or acting with excitement you cannot control, trembling or shaking, twitching, and vomiting.
• Affected Organisms: Humans and other mammals
• Biotransformation: Hepatic.

Sigma Aldrich - T4196

Other Notes
Amino acid precursor of serotonin and melatonin
Packaging
Manufactured and packaged under cGMP

Sigma Aldrich - T8941

Other Notes
血清素和褪黑激素的氨基酸前体
包装
10 mg in autosmp vl

Sigma Aldrich - 93659

Other Notes
Amino acid precursor of serotonin and melatonin
In tryptophan-substituted Sephadex® and Sepharose® for the improved chromatographic separation of cellulases1; As spacer in isotachophoresis of serum proteins2; Growth requirement of various microorganisms3.
Tandem Mass Spectrometry data independently generated by Scripps Center for Metabolomics is available to view or download in PDF. 93659.pdf Tested metabolites are featured on Scripps Center for Metabolomics METLIN Metabolite Database. To learn more, visit sigma.com/metlin.
Legal Information
Sephadex is a registered trademark of GE Healthcare
Sepharose is a registered trademark of GE Healthcare

Sigma Aldrich - T90204

Other Notes
Amino acid precursor of serotonin and melatonin
Application
Employed in the synthesis of bridged indole alkaloids.1

Sigma Aldrich - 51145

Analysis Note
This certified reference material (CRM) is produced and certified in accordance with ISO/IEC 17025 and ISO Guide 34. This CRM is traceable to NIST SRM.
General description
Certified content by quantitative NMR incl. uncertainty and expiry are given in the certificate.Download your certificate at: http://www.sigma-aldrich.com.
Other Notes
Amino acid precursor of serotonin and melatonin
Legal Information
TraceCERT is a registered trademark of Sigma-Aldrich Co. LLC

Sigma Aldrich - T0254

Other Notes
血清素和褪黑激素的氨基酸前体
包装
1 kg in poly bottle
1, 5, 25, 100, 500 g in poly bottle

Toronto Research Chemicals - T947210

Essential amino acid.

REFERENCES

• Goze, C., et al.: Eur. J. Pharmacol., 643, 153 (2010)
• Bhandare, P., et al.: J. Chem. Pharm. Res., 2, 372 (2010)