D-Tryptophan

HCID 9060CAS 153-94-6

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

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

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 · 3 items

527 to 540 °F (NTP, 1992)

282-85 dec °C

282 - 85 °C

Physical Description · 3 items

D(+)-tryptophan is a white solid. (NTP, 1992)

White solid; [CAMEO] White powder; [Alfa Aesar MSDS]

Solid

Collision Cross Section · 2 items

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

Safety & regulation

GHS classification

GHS Classification · 5 items

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 · 1 item

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.

Air and Water ReactionsSlightly soluble in water.

Safety & protection

Fire FightingFires involving this compound should be controlled using a dry chemical, carbon dioxide or Halon extinguisher. (NTP, 1992)
First Aid · 1 item

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 · 1 item

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) · 1 item

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

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 · 5 items

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.

Suppliers50 total

北京华美互利生物化工010-56205725 · [email protected]
梯希爱(上海)化成工业发展有限公司021-67121386 · [email protected]
衢州润东化工有限公司0570-8789886 18892685668 · [email protected]
上海阿拉丁生化科技股份有限公司400-6206333 13167063860 · [email protected]
INTATRADE GmbH+49 3493/605464 · [email protected]

Additional notes

DefinitionChEBI: The D-enantiomer of tryptophan.

Related reactions

53 records

Linked notes

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