L-Tryptophan, methyl ester

HCID 77980CAS 4299-70-1

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Basic information

Standard SMILES: COC(=O)[C@@H](N)Cc1c[nH]c2ccccc12
InChIKey: KCUNTYMNJVXYKZ-JTQLQIEISA-N
Molecular formula: C12H14N2O2
Average molar mass: 218.25 g/mol
Monoisotopic mass: 218.10552769

Names & identifiers

Preferred name: L-Tryptophan, methyl ester
IUPAC: methyl (2S)-2-amino-3-(1H-indol-3-yl)propanoate
English name: methyl L-tryptophanate
Molecular formula: C12H14N2O2
Molecular weight: 218.25

Names & synonyms

4299-70-1L-Tryptophan methyl esterL-Tryptophan, methyl esterEINECS 224-309-7DTXSID30884057RefChem:798154DTXCID901023529Methyl L-tryptophanate(S)-methyl 2-amino-3-(1H-indol-3-yl)propanoateTryptophan methyl esterMFCD08144704L-Tryptophane methyl ester

Show more names

(S)-Tryptophan methyl estermethyl L-tryptophanate USP/EP/BPTryptophan methyl ester hydrochloride3-(1H-Indole-3-yl)-L-alanine methyl ester(αS)-α-Amino-1H-indole-3-propanoic acid methyl ester(2S)-2-Amino-3-(1H-indole-3-yl)propionic acid methyl ester(2S)-2-Amino-3-(1H-indole-3-yl)propanoic acid methyl ester

methyl (2S)-2-amino-3-(1H-indol-3-yl)propanoateTryptophan, methyl ester, L-(S)-2-Amino-3-(1H-indol-3-yl)-propionic acid methyl estertryptophan methylesterTrp-OMeTadalafil Impurity PH-L-Trp-OMeTrp-OCH3

Database identifiers

CAS: 4299-70-1
PubChem CID: 77980
DTXSID: DTXSID30884057
ChEMBL: CHEMBL55830
UNII: ZP5C4VEH76
EC Number: 224-309-7
Nikkaji: J205.692E

Properties

Computed structural properties

XLogP: 1.5
Topological polar surface area: 68.1 Å²
Hydrogen bond donors: 2
Hydrogen bond acceptors: 3
Rotatable bonds: 4
Heavy atoms: 16
Formal charge: 0
Complexity: 257

Physicochemical properties

Melting point: 91 · 91-92℃
Boiling point: 391 ℃ · 391℃
Density: 1.245 · 1.245
Flash point: 190 ℃ · 190℃
pka: 17.02 · 17.02±0.30(Predicted)
form: solid
InChI: 1S/C12H14N2O2/c1-16-12(15)10(13)6-8-7-14-11-5-3-2-4-9(8)11/h2-5,7,10,14H,6,13H2,1H3/t10-/m0/s1
InChIKey: KCUNTYMNJVXYKZ-JTQLQIEISA-N
SMILES: COC(=O)[C@@H](N)Cc1c[nH]c2ccccc12
EPA Substance Registry System: L-Tryptophan, methyl ester (4299-70-1)
UNSPSC Code: 12352106 · 12352106
WGK Germany: 3 · WGK 3
TSCA: TSCA listed
Storage Class: 11 · 11 - Combustible Solids

Safety & regulation

Safety data

wgk: WGK 3
tsca: TSCA listed
Storage Class: 11 - Combustible Solids

Chemistry & industry

Uses & manufacturing

General Manufacturing InformationL-Tryptophan, methyl ester: INACTIVE

Applications · 1 item

UsesL-Tryptophan Methyl Ester is the acidic-free form of L-Tryptophan Methyl Ester Hydrochloride (T895010), which is an amino acid derivative that may be used to prepare the corresponding amino acid amide L-Trytophanamide Hydrochloride. Also, it is an intermediate used in the synthesis of (1S,3S)-1-(1,3-Benzodioxol-5-yl)-2,3,4,9-tetrahydro-1H-pyrido[3,4-b]indole-3-carboxylic Acid Methyl Ester (B200020), which is a Tadalafil (T004500) derivative and used in the preparation of pyrazinopyridoindole derivatives for their PDE5 inhibitory activity.