D-Tryptophan
Basic information
- CAS
153-94-6- Standard SMILES
N[C@H](Cc1c[nH]c2ccccc12)C(=O)O- InChIKey
QIVBCDIJIAJPQS-SECBINFHSA-N- Molecular formula
- C11H12N2O2
- Average molar mass
- 204.22 g/mol
- Monoisotopic mass
- 204.08987762
Overview
D(+)-tryptophan is a white solid. (NTP, 1992)
Names & identifiers
- Preferred name
- D-Tryptophan
- IUPAC
- (2R)-2-amino-3-(1H-indol-3-yl)propanoic acid
- English name
- D-Tryptophan
- Molecular formula
- C11H12N2O2
- Molecular weight
- 204.23
Names & synonyms
D-Tryptophan153-94-6D(+)-Tryptophan(2R)-2-amino-3-(1H-indol-3-yl)propanoic acid(R)-Tryptophan(+)-TryptophanD-TrytophaneTryptophan, D-D-(+)-TryptophanDTXSID00469897NS97N9H1GEINECS 205-819-9
Show more names
D-TRPH-D-TRP-OHLTRD-Trp-OHWVD-TriptophanD-2-AMINO-3-(3-INDOLYL)PROPIONIC ACIDTRP-01
NSC 97942CHEBI:16296NSC-97942DTXCID8026989DTryptophane(R)TryptophanTryptophan, DD(+)Tryptophan
Database identifiers
- CAS
153-94-6- PubChem CID
- 9060
- DTXSID
DTXSID0046989- ChEMBL
CHEMBL292303- ChEBI
CHEBI:16296- UNII
- 7NS97N9H1G
- EC Number
- 205-819-9
- Nikkaji
- J9.185E
Properties
Computed structural properties
- XLogP
- -1.1
- Topological polar surface area
- 79.1 Ų
- Hydrogen bond donors
- 3
- Hydrogen bond acceptors
- 3
- Rotatable bonds
- 3
- Heavy atoms
- 15
- Formal charge
- 0
- Complexity
- 245
Experimental & physicochemical properties
Chemical ClassesBiological Agents -> Amino Acids and Derivatives
DrugsPharmaceuticals -> Listed in ZINC15
Solubility1 to 5 mg/mL at 75 °F (NTP, 1992)
Melting Point
527 to 540 °F (NTP, 1992)
282-85 dec °C
282 - 85 °C
Physical Description
D(+)-tryptophan is a white solid. (NTP, 1992)
White solid; [CAMEO] White powder; [Alfa Aesar MSDS]
Solid
Collision Cross Section
151.5 Ų [M-H]- [CCS Type: DT; Buffer gas: N2; Ionization: ESI-; Dataset: TOXCAST; Source Identifier: DTXSID0046989]
142.6 Ų [M-H]-
Physicochemical properties
- Melting point
- 282 · 282-285 °C (dec.)(lit.)
- alpha
- 31.5 · 31.5 º (c=1, H2O 24 ºC)
- Boiling point
Safety & regulation
Safety information is for reference only and does not replace the supplier’s Safety Data Sheet (SDS), applicable regulations, or professional assessment.
GHS classification
GHS Classification
This chemical does not meet GHS hazard criteria for 87.5% (7 of 8) of all reports.
Warning
H315 (12.5%): Causes skin irritation [Warning Skin corrosion/irritation]
P261, P264, P264+P265, P271, P280, P302+P352, P304+P340, P305+P351+P338, P319, P321, P332+P317, P337+P317, P362+P364, P403+P233, P405, and P501 (click each P-code to see the statement)
Aggregated GHS information provided per 8 reports by companies from 2 notifications to the ECHA C&L Inventory. Each notification may be associated with multiple companies.
Hazard information
Regulatory InformationD-Tryptophan: Does not have an individual approval but may be used under an appropriate group standard
Fire HazardsFlash point data are not available for this chemical, but it is probably combustible. (NTP, 1992)
Hazards SummaryCauses altered sleep time (including change in righting reflex), dyspnea, and decreased body temperature in intraperitoneal lethal-dose studies of rats (LD50 = 4,289 mg/kg); [RTECS] May cause irritation; [Alfa Aesar MSDS]
Reactive GroupSalts, Acidic
Reactivity Profile
Acidic salts, such as D(+)-TRYPTOPHAN, are generally soluble in water. The resulting solutions contain moderate concentrations of hydrogen ions and have pH's of less than 7.0. They react as acids to neutralize bases. These neutralizations generate heat, but less or far less than is generated by neutralization of inorganic acids, inorganic oxoacids, and carboxylic acid. They usually do not react as either oxidizing agents or reducing agents but such behavior is not impossible. Many of these compounds catalyze organic reactions.
Chemistry & industry
Uses & manufacturing
UsesTryptophan is an essential amino acid; [Merck Index] Used as a dietary supplement and for nutrition research; [NTP]
General Manufacturing InformationD-Tryptophan: ACTIVE
Applications
DescriptionD(+)-tryptophan is the D-form (non-proteinogenic form) of the amino acid tryptophan. It can be used for Human embryonic kidney cell (HEK-293, ATCC: CRL-1573) culture. It is also a sweetener used to study the release of incretins from enteroendocrine cells triggered by sugar but not by sweeteners.
DescriptionD-tryptophan (Full name D (+)-Tryptophan) is a white to pale yellow or white crystalline powder at room temperature, odorless or slight odor, slightly sweet taste. Solubility in water is 1.14 g (25 ℃), soluble in dilute acid and alkali, stable in alkali, decomposed in strong acid, slightly soluble in ethanol, not soluble in chloroform, ethyl ether. It plays an important role for human and animal growth and development, metabolism, known as the second essential amino acids. They are almost identical with L-type and physical and chemical properties, and only the optical activity is opposite. But their distribution, function and coenzyme have diversity. Its melting point is very high, generally above 200 degrees. It can dissolve in water, and in the near UV region it has the ability to absorb light. Tryptophan is one of the 20 standard amino acids, as well as an essential amino acid in the human diet. It is encoded in the standard genetic code as the codon UGG. the D-stereoisomer is occasionally found in naturally produced peptides (for example, the marine venom peptide contryphan). The distinguishing structural characteristic of tryptophan is that it contains an indole functional group. It is an essential amino acid as defined by its growth effects on rats.
UsesAn essential amino acid found in naturally produced pedtides. Unlike its stereoisomer, L-tryptophan, it is not used in structural or enzyme proteins.
UsesD-Tryptophan is used for human embryonic kidney cell (HEK-293, ATCC: CRL-1573) culture. The product is a sweetener used to study the release of incretins from enteroendocrine cells triggered by sugar but not by sweeteners.
Related reactions
53 records
Compound notes
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