Basic information
- 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
Show more names
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
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
- 342.72 °C · 342.72°C (rough estimate)
- Density
- 1.1754 · 1.1754 (rough estimate)
- refractive index
- 31 ° · 31 ° (C=1, H2O)
- storage temp.
- Keep in dark place,Inert atmosphere,Room temperature
- solubility
- Aqueous Base (Slightly), DMSO (Slightly, Heated, Sonicated), Methanol (Slightly)
- pka
- 2.3 · 2.30±0.10(Predicted)
- form
- Powder
- color
- White to slightly yellow
- biological source
- synthetic (organic)
- optical activity
- Consistent with structure
- Water Solubility
- 11 g/L · 11 g/L (20 ºC)
- BRN
- 86198 · 86198
- Stability
- Stable. Incompatible with oxidizing agents.
- 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-/m1/s1
- InChIKey
- QIVBCDIJIAJPQS-SECBINFHSA-N
- SMILES
- N[C@H](Cc1c[nH]c2ccccc12)C(O)=O
- LogP
- 0.704 · 0.704 (est)
- CAS DataBase Reference
- 153 · 153-94-6(CAS DataBase Reference)
- FDA UNII
- 7 NS97N9H1G · 7NS97N9H1G
- EPA Substance Registry System
- D-Tryptophan (153-94-6)
- UNSPSC Code
- 12352103 · 12352103
- NACRES
- 32 · NA.32
- Symbol(GHS)
- 7 · GHS07
- Signal word
- Warning
- Hazard statements
- 315 · H315-H319-H335
- Precautionary statements
- 302 · P302+P352-P305+P351+P338-P362+P364
- PPE
- 95 · Eyeshields, Gloves, type N95 (US)
- Hazard Codes
- Xi
- Risk Statements
- 36 · 36/37/38-41-37/38-22
- Safety Statements
- 24 · 24/25-36/37/39-36-26
- WGK Germany
- 3 · 3
- RTECS
- 6129000 · YN6129000
- F
- 8 · 8
- TSCA
- TSCA listed
- HazardClass
- IRRITANT
- HS Code
- 29339990 · 29339990
- Storage Class
- 11 · 11 - Combustible Solids
Safety & regulation
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
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.
Safety & protection
First Aid
EYES: First check the victim for contact lenses and remove if present. Flush victim's eyes with water or normal saline solution for 20 to 30 minutes while simultaneously calling a hospital or poison control center. Do not put any ointments, oils, or medication in the victim's eyes without specific instructions from a physician. IMMEDIATELY transport the victim after flushing eyes to a hospital even if no symptoms (such as redness or irritation) develop.
Nonfire Spill Response
SMALL SPILLS AND LEAKAGE: Should a spill occur while you are handling this chemical, you should dampen the solid spill material with alcohol, then transfer the dampened material to a suitable container. Use absorbent paper dampened with alcohol to pick up any remaining material. Seal the absorbent paper, and any of your clothes, which may be contaminated, in a vapor-tight plastic bag for eventual disposal. Solvent wash all contaminated surfaces with alcohol followed by washing with a strong soap and water solution. Do not reenter the contaminate area until the Safety Officer (or other responsible person) has verified that the area has been properly cleaned.
Personal Protective Equipment (PPE)
RECOMMENDED RESPIRATOR: Where the neat test chemical is weighed and diluted, wear a NIOSH-approved half face respirator equipped with an organic vapor/acid gas cartridge (specific for organic vapors, HCl, acid gas and SO2) with a dust/mist filter. (NTP, 1992)
Safety data
- F
- 8
- PPE
- Eyeshields, Gloves, type N95 (US)
- wgk
- 3
- tsca
- TSCA listed
- rtecs
- YN6129000
- hs_code
- 29339990
- risk_code
- 36/37/38-41-37/38-22
- Signal word
- Warning
- Symbol(GHS)
- GHS07
- hazard_code
- Xi
- safety_code
- 24/25-36/37/39-36-26
- hazard_class
- IRRITANT
- Storage Class
- 11 - Combustible Solids
- Hazard statements
- H315-H319-H335
- Precautionary statements
- P302+P352-P305+P351+P338-P362+P364
Chemistry & industry
Uses & manufacturing
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.
General DescriptionWhite solid.
Upstream & downstream products
Upstream raw materials
Downstream products
Suppliers50 total
Additional notes
DefinitionChEBI: The D-enantiomer of tryptophan.
Related reactions
Linked notes
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