N-Acetyltryptophan (HCID 2002)

Names & identifiers

Preferred name: N-Acetyltryptophan
IUPAC: 2-acetamido-3-(1H-indol-3-yl)propanoic acid
English name: N-Acetyl-DL-tryptophan
Molecular formula: C13H14N2O3
Molecular weight: 246.26

Names & synonyms

N-Acetyl-DL-tryptophan87-32-1N-Acetyltryptophanacetyltryptophan2-acetamido-3-(1H-indol-3-yl)propanoic acidDL-AcetyltryptophanDL-N-AcetyltryptophanTryptophan, N-acetyl-N-Acetyl-DL-tryptophaneNSC49124n-acetyltryptophaneNSC 49124

Show more names

AC-DL-TRP-OHAC-DL-TrpAURORA 2470N-Ac-DL-Trp-OHN-ACETYL-DL-TRPAKOS BBS-00007672N-Ac-DL-Tryptophan

4460NBV53FAC-TryEINECS 201-739-3NSC-49124ACETYLTRYPTOPHAN, DL-Acetyl tryptophand,l-alpha-Acetylamino-3-indolepropionic acidCHEBI:70976

Database identifiers

CAS: 1218-34-4、87-32-1
PubChem CID: 2002
DTXSID: DTXSID40861672
ChEMBL: CHEMBL1905494、CHEMBL54170
ChEBI: CHEBI:70976
UNII: 4460NBV53F
EC Number: 201-739-3

Properties

Computed structural properties

XLogP: 1.1
Topological polar surface area: 82.2 Å²
Hydrogen bond donors: 3
Hydrogen bond acceptors: 3
Rotatable bonds: 4
Heavy atoms: 18
Formal charge: 0
Complexity: 332

Experimental & physicochemical properties

Physical DescriptionBeige powder; [Sigma-Aldrich MSDS]

Collision Cross Section · 3 items

157.36 Å² [M+K]+ [CCS Type: TW; Method: calibrated with polyalanine and drug standards]；151.44 Å² [M+H]+ [CCS Type: TW; Method: calibrated with polyalanine and drug standards]；155.4 Å² [M+Na]+ [CCS Type: TW; Method: calibrated with polyalanine and drug standards]；146.86 Å² [M+H-H2O]+ [CCS Type: TW; Method: calibrated with polyalanine and drug standards]

153.8 Å² [M+H]+ [CCS Type: DT; Method: single field calibrated with ESI Low Concentration Tuning Mix (Agilent)]；158.3 Å² [M-H]- [CCS Type: DT; Method: single field calibrated with ESI Low Concentration Tuning Mix (Agilent)]；158.5 Å² [M+Na]+ [CCS Type: DT; Method: single field calibrated with ESI Low Concentration Tuning Mix (Agilent)]

153.4 Å² [M+H]+；158.6 Å² [M-H]-；158.1 Å² [M+Na]+

Physicochemical properties

Melting point: 204 · 204-206 °C (dec.) (lit.)
Boiling point: 389.26 °C · 389.26°C (rough estimate)
alpha: -0.5 · -0.5~+0.5°(20℃/D)(c=2,C2H5OH)
Density: 1.1855 · 1.1855 (rough estimate)
vapor pressure: 0.00005 mPa · <0.00005 mPa ( 20 °C)
refractive index: 1.645 · 1.6450 (estimate)
storage temp.: 2 · 2-8°C
solubility: Slightly soluble in water, very soluble in ethanol (96 per cent). It dissolves in dilute solutions of alkali hydroxides.
pka: 3.65 · 3.65±0.10(Predicted)
form: Powder
color: White to light yellow
PH: 3.25 · 3.25 (20°C, 0.5g/L in H2O)
biological source: synthetic
Water Solubility: INSOLUBLE IN COLD WATER
BRN: 89478 · 89478
Stability: Stable. Incompatible with strong oxidizing agents.
Major Application: liquid formulationparenteralspharma/biopharma processes
InChI: 1S/C13H14N2O3/c1-8(16)15-12(13(17)18)6-9-7-14-11-5-3-2-4-10(9)11/h2-5,7,12,14H,6H2,1H3,(H,15,16)(H,17,18)
InChIKey: DZTHIGRZJZPRDV-UHFFFAOYSA-N
SMILES: CC(=O)NC(Cc1c[nH]c2ccccc12)C(O)=O
LogP: -0.408 · -0.408 (est)
CAS DataBase Reference: 87 · 87-32-1(CAS DataBase Reference)
FDA UNII: 4460 NBV53F · 4460NBV53F
NIST Chemistry Reference: Acetyl-dl-tryptophan(87-32-1)
EPA Substance Registry System: Tryptophan, N-acetyl- (87-32-1)
UNSPSC Code: 12352209 · 12352209
NACRES: 26 · NA.26
Symbol(GHS): 7 · GHS07
Signal word: Warning
Hazard statements: 302 · H302-H315-H319-H335
Precautionary statements: 261 · P261-P301+P312-P302+P352-P304+P340-P305+P351+P338
Safety Statements: 24 · 24/25
WGK Germany: 3 · 3
Hazard Note: Keep Cold
TSCA: TSCA listed
HS Code: 29339990 · 29339990
Storage Class: 11 · 11 - Combustible Solids
REACH Registrations: Active

Safety & regulation

GHS classification

GHS Classification · 3 items

This chemical does not meet GHS hazard criteria for 97.6% (41 of 42) of all reports.

Not Classified；Reported as not meeting GHS hazard criteria by 41 of 42 companies (only 2.4% companies provided GHS information). For more detailed information, please visit ECHA C&L website.

Aggregated GHS information provided per 42 reports by companies from 3 notifications to the ECHA C&L Inventory.；Reported as not meeting GHS hazard criteria per 41 of 42 reports by companies.；There is 1 notification provided by 1 of 42 reports by companies with hazard statement code(s).；Information may vary between notifications depending on impurities, additives, and other factors. The percentage value in parenthesis indicates the notified classification ratio from companies that provide hazard codes. Only hazard codes with percentage values above 10% are shown. For more detailed information, please visit ECHA C&L website.

Hazard information

Regulatory Information · 2 items

Status: Active Update: 19-05-2018 https://echa.europa.eu/registration-dossier/-/registered-dossier/24518

Tryptophan, N-acetyl-: Does not have an individual approval but may be used under an appropriate group standard

Hazards SummaryMay cause irritation; [Sigma-Aldrich MSDS] See Tryptophan.

Hazard Classes and CategoriesNot Classified

Regulatory information

Regulatory Information · 2 items

Status: Active Update: 19-05-2018 https://echa.europa.eu/registration-dossier/-/registered-dossier/24518

Tryptophan, N-acetyl-: Does not have an individual approval but may be used under an appropriate group standard

Safety data

wgk: 3
tsca: TSCA listed
hs_code: 29339990
Signal word: Warning
Symbol(GHS): GHS07
hazard_note: Keep Cold
safety_code: 24/25
Storage Class: 11 - Combustible Solids
Hazard statements: H302-H315-H319-H335
REACH Registrations: Active
Precautionary statements: P261-P301+P312-P302+P352-P304+P340-P305+P351+P338

Chemistry & industry

Pharmacology

MeSH Pharmacological ClassificationCompounds which inhibit or antagonize biosynthesis or actions of proteases (ENDOPEPTIDASES).

Uses & manufacturing

General Manufacturing InformationTryptophan, N-acetyl-: ACTIVE

Applications

UsesN-Acetyl-DL-tryptophan is produced via chemical synthesis using the standard amino acid, tryptophan. It can be used in downstream applications of biopharmaceutical production as a transfer agent or stabilizer.