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

• ChemBase ID: 35858
• Molecular Formular: C11H12N2O2
• Molecular Mass: 204.22518
• Monoisotopic Mass: 204.08987763
• SMILES: c1(c[nH]c2c1cccc2)CC(C(=O)O)N
• Canonical SMILES: OC(=O)C(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)
• InChIKey: QIVBCDIJIAJPQS-UHFFFAOYSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: 2-amino-3-(1H-indol-3-yl)propanoic acid
• IUPAC Traditional name: tryptophan(.)
• Synonyms: DL-2-Amino-3-indolepropionic acid; DL-3β-Indolylalanine; DL-TRYPTOPHAN; (+/-)-2-Amino-3-(3-indolyl)propionic acid; H-DL-Trp-OH; (+/-)-Tryptophan; 1H-Indole-3-alanine; DL-α-Amino-3-indolepropionic Acid; NSC 13118; D,L-Tryptophan; (±)-α-Amino-3-indolepropionic acid; (±)-2-Amino-3-(3-indolyl)propionic acid; DL-3β-Indolylalanine; DL-Tryptophan; Tryptophan; (±)-2-氨基-3-(3-吲哚基)丙酸; DL-β-(3-吲哚基)-α-氨基丙酸; DL-氨基吲哚丙酸; DL-色氨酸

Database IDs

• CAS Number: 54-12-6; 153-94-6
• EC Number: 200-194-9
• MDL Number: MFCD00064339
• Beilstein Number: 86196; 86199
• PubChem SID: 24850000; 160999165; 24900128
• PubChem CID: 1148

CALCULATED PROPERTIES

• 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

PROPERTIES

Physical Property

• Solubility: DMSO; Methanol
• Apperance: Off-White Solid
• Melting Point: ~295 °C (dec.); 263-265°C (dec.)C; 289-290 °C (dec.)(lit.); 289-290°C; ca 280°C dec.

Safety Information

• Storage Condition: Refrigerator; Room Temperature (15-30°C)
• Storage Warning: IRRITANT
• RTECS: YN6129200
• German water hazard class: 1
• TSCA Listed: false; 是
• Personal Protective Equipment: Eyeshields, Gloves, type N95 (US), type P1 (EN143) respirator filter

Product Information

• Purity: ≥99%; ≥99% (TLC); ≥99.0% (NT); 98%; 99%
• Grade: puriss.
• Suitability: suitable for cell culture
• Empirical Formula (Hill Notation): C11H12N2O2

DETAILS

MP Biomedicals - 02103147

Purity: 99%
Crystalline

MP Biomedicals - 02194757

Cell Culture Reagent
Purity: 99%
Crystalline

Sigma Aldrich - T7425

Application
For use in insect and mammalian cell culture applications where the pure L-form is not required.
Preparation Note
Prepared from L-tryptophan produced by fermentation.

Sigma Aldrich - T3300

Other Notes
Amino acid precursor of serotonin and melatonin
Preparation Note
Prepared from L-tryptophan produced by fermentation

Sigma Aldrich - 162698

Packaging
1.5 g in glass bottle
50 g in poly bottle

Toronto Research Chemicals - T947200

Essential amino acid.

REFERENCES

• Liu, F., et al.: Bioorg. Med. Chem., 18, 4167 (2010)
• Kumar, R., et al.: Eur. J. Med. Chem., 45, 2265 (2010)
• Cai, W., et al.: Bioorg. Med. Chem., 18, 1899 (2010)