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D-Tryptophan

CAS No.
153-94-6
Chemical Name:
D-Tryptophan
Synonyms
D-TRYPTOPHAN;D-TRP;H-D-TRP-OH;LTR;D-Trp-OH;WV;D-Triptophan;D(+)-TRYPTOPHAN;D-2-AMINO-3-(3-INDOLYL)PROPIONIC ACID;TRP-01
CBNumber:
CB2280905
Molecular Formula:
C11H12N2O2
Molecular Weight:
204.23
MDL Number:
MFCD00005647
MOL File:
153-94-6.mol
MSDS File:
SDS
TDS File:
TDS
Last updated:2026-07-01 11:16:45

D-Tryptophan Properties

Melting point 282-285 °C (dec.)(lit.)
alpha 31.5 º (c=1, H2O 24 ºC)
Boiling point 342.72°C (rough estimate)
Density 1.1754 (rough estimate)
refractive index 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 2.30±0.10(Predicted)
form Powder
color White to slightly yellow
biological source synthetic (organic)
optical activity Consistent with structure
Water Solubility 11 g/L (20 ºC)
BRN 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 (est)
CAS DataBase Reference 153-94-6(CAS DataBase Reference)
FDA UNII 7NS97N9H1G
EPA Substance Registry System D-Tryptophan (153-94-6)
UNSPSC Code 12352103
NACRES NA.32

SAFETY

Risk and Safety Statements

Symbol(GHS)  Exclamation Mark (GHS07)
GHS07
Signal word  Warning
Hazard statements  H315-H319-H335
Precautionary statements  P302+P352-P305+P351+P338-P362+P364
PPE Eyeshields, Gloves, type N95 (US)
Hazard Codes  Xi
Risk Statements  36/37/38-41-37/38-22
Safety Statements  24/25-36/37/39-36-26
WGK Germany  3
RTECS  YN6129000
8
TSCA  TSCA listed
HazardClass  IRRITANT
HS Code  29339990
Storage Class 11 - Combustible Solids
NFPA 704
1
1 0

D-Tryptophan price More Price(109)

Manufacturer Product number Product description CAS number Packaging Price Updated Buy
Sigma-Aldrich T9753 D-Tryptophan ≥98.0% (HPLC) 153-94-6 1g $25.7 2026-04-30 Buy
Sigma-Aldrich T9753 D-Tryptophan ≥98.0% (HPLC) 153-94-6 5g $65.4 2026-04-30 Buy
TCI Chemical T0539 D-Tryptophan >98.0%(HPLC)(T) 153-94-6 5g $25 2026-04-30 Buy
TCI Chemical T0539 D-Tryptophan >98.0%(HPLC)(T) 153-94-6 25g $95 2026-04-30 Buy
Usbiological 289796 D-Tryptophan Asreported 153-94-6 50g $389 2026-06-03 Buy
Product number Packaging Price Buy
T9753 1g $25.7 Buy
T9753 5g $65.4 Buy
T0539 5g $25 Buy
T0539 25g $95 Buy
289796 50g $389 Buy

D-Tryptophan Chemical Properties,Uses,Production

Description

D(+)-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.

Description

D-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.

Characteristics and Functions

D-tryptophan amino acid, as a non-reactive protein, has special physiological properties. It can be used as a non-nutritive sweeteners, feed additive, plant growth agents in food feed industry and agriculture. In the pharmaceutical industry, it mainly used for the synthesis of various polypeptides, instead of L-tryptophan peptide drug for half-life extending and reduce the side effects, but it will not resistant to the front body, and it will become important enzyme inhibitor. It can also improve the body's immunity, delayed allergic reactions. Most peptide antibiotic can resistant gram-positive bacteria, Gram-negative bacteria and some, such as Pseudomonas aeruginosa, mycobacteria, fungi, bacteria, pathogens and tumor cells, which have better inhibit and kill ability.
D-tryptophan can be used for the synthetic of semi-synthetic antibiotics, for which pharmacological plays an important role for the side chain. The peptide bond is difficult to be β-lactam enzyme action, thus high stability, and has broad antibacterial spectrum, toxicity, hypoallergenic, rapid absorption, high blood concentrations of the drug long duration.

Project Standards

Appearance  white or slightly yellow crystalline powder
Content 99.0%~101.0%
Specific rotation [α] D20 + 30.5 °~+ 32.5 °
Transmittance ≥95.0%
Acidity PH 5.5~6.4
Loss on drying ≤0.2%
Residue on ignition ≤0.1%
Chloride [Cl-] ≤0.02%
Sulphate [SO42-] ≤0.02%
Ammonium [NH4 +] ≤0.02%
Heavy metals [Pb] ≤10ppm
Ferric [Fe] ≤10ppm
Arsenic salt [As2O3] ≤1ppm
Other amino acids compliance

Application

An important nutrient, niacin is used as the control agent Medicine
Production method: D-tryptophan as raw material, chloroacetic anhydride was added under cooling state after polishing sulfuric acid in ice water, filtered and recrystallized from water, and finally treatment with carboxypeptidase trypsin to remove L-type, acidified with acetic acid, ethanol recrystallization refining.

References

https://pubchem.ncbi.nlm.nih.gov/compound/D-Tryptophan#section=Top

References

Fujita, Yukihiro, et al. "Incretin release from gut is acutely enhanced by sugar but not by sweeteners in vivo." American Journal of Physiology Endocrinology & Metabolism 296.3(2009):E473.
Bacchus, W, W. Weber, and M. Fussenegger. "Increasing the dynamic control space of mammalian transcription devices by combinatorial assembly of homologous regulatory elements from different bacterial species." Metabolic Engineering 15.1(2013):144.

Chemical Properties

white powder

Uses

An essential amino acid found in naturally produced pedtides. Unlike its stereoisomer, L-tryptophan, it is not used in structural or enzyme proteins.

Uses

D-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.

Definition

ChEBI: The D-enantiomer of tryptophan.

Antimicrobial activity

Research showed that when D-tryptophan was used with other stresses such as using different salt concentrations, refrigeration, or high temperatures, it showed significant antimicrobial effects on Gram-positive and Gram-negative food-borne pathogens, and antibiofilm impacts were also observed with D-tryptophan[2].

General Description

White solid.

Air & Water Reactions

Slightly soluble in water.

Reactivity Profile

Amines are chemical bases. They neutralize acids to form salts plus water. These acid-base reactions are exothermic. The amount of heat that is evolved per mole of amine in a neutralization is largely independent of the strength of the amine as a base. Amines may be incompatible with isocyanates, halogenated organics, peroxides, phenols (acidic), epoxides, anhydrides, and acid halides. Flammable gaseous hydrogen is generated by amines in combination with strong reducing agents, such as hydrides.

Fire Hazard

Flash point data are not available for D(+)-Tryptophan, but D(+)-Tryptophan is probably combustible.

Pharmaceutical Applications

Preclinical and emerging clinical findings suggest that D-tryptophan may influence neural plasticity and cognitive processes through modulation of NMDA receptor activity, glutamatergic neurotransmission, and neurotrophic factor release. Beyond cognitive domains, potential benefits may extend to behavioral and mood regulation, highlighting their multifaceted role in Central Nervous System (CNS) health[1].

Biochem/physiol Actions

Low level of D-tryptophan is capable of preventing the growth of anL-tryptophan-requiring mutant of theE. coli.

References

[1] Dhurandhar, Y., Tomar, S., Das, A., Bodakhe, S. H., & Namdeo, K. P. (2026). Modulating the Brain with D-Amino Acids: Exploring D-Tryptophan and D-Phenylalanine in CNS Disorders. Current Nutraceuticals, 07. https://doi.org/10.2174/0126659786446199260108060446
[2] Moghimani, M., Noori, S. M. A., Afshari, A., & Hashemi, M. (2024). D-tryptophan, an eco-friendly natural, safe, and healthy compound with antimicrobial activity against food-borne pathogens: A systematic review. Food Science & Nutrition, 12 5, 3068–3079. https://doi.org/10.1002/fsn3.3987

73-22-3
153-94-6
Synthesis of D-Tryptophan from L-Tryptophan
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View Lastest Price from D-Tryptophan manufacturers

Image Update time Product Price Min. Order Purity Supply Ability Manufacturer
D-Tryptophan pictures 2026-09-13 D-Tryptophan
153-94-6
$10.00 1kg ≥ 98.5% 20 tons Nantong Provichem Biotech Co., Ltd.
D(+)-Tryptophan pictures 2026-09-11 D(+)-Tryptophan
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$75.00-100.00 1kg 99% 5000Ton HEBEI SHENGSUAN CHEMICAL INDUSTRY CO.,LTD
D(+)-Tryptophan pictures 2026-09-11 D(+)-Tryptophan
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1kg 98%min 500kgs WUHAN FORTUNA CHEMICAL CO., LTD
  • D-Tryptophan pictures
  • D-Tryptophan
    153-94-6
  • $10.00
  • ≥ 98.5%
  • Nantong Provichem Biotech Co., Ltd.
  • D(+)-Tryptophan pictures
  • D(+)-Tryptophan
    153-94-6
  • $75.00-100.00
  • 99%
  • HEBEI SHENGSUAN CHEMICAL INDUSTRY CO.,LTD
D-TRYPTOPHAN D-TRYPTOPHANE D-2-AMINO-3-(3-INDOLYL)PROPIONIC ACID D-2-AMINO-3-INDOLEPROPIONIC ACID D-2-AMINO-3-INDOLYLPROPANOIC ACID D-ALPHA-AMINO-3-INDOLEPROPIONIC ACID D-A-AMINO-3-INDOLEPROPIONIC ACID D-TRYPTOPHAN, 99+% (99% EE/GLC) D-TRYPTOPHAN, H-D-TRP-OH D-TRYTOPHAN D(+)-Tryptophan, 99+% H-D-TRP-OH USP24 (IN BULK QUANTITY) TRYPTOPHAN, D-(RG) (R)-a-Amino-3-indolepropionic acid (R)-a-Aminoindole-3-propanoic acid D-Tryptophan (9CI) NSC 97942 Tryptophan, D- (8CI) D-TRYPTOPHAN, =98.0% (HPLC) D-Tryptophan≥ 99% (Assay) FREE SAMPLE NCV D-TRYPTOPHAN H-D-Trp-OH (R)-2-Amino-3-(3-indolyl)propionic acid D-α-Amino-3-indolepropionic acid 3,3'-Indolyl-2-alanine D-Tryptophan,99%e.e. (R)-2-Amino-3-(3-indolyl)propionic acid~H-D-Trp-OH D-Tryptophane, (R)-2-Amino-3-(3-indolyl)propionic acid, D-a-Amino-3-indolepropionic acid (2R)-2-amino-3-(1H-indol-3-yl)propanoic acid (αR)-α-Amino-1H-indole-3-propanoic acid (R)-2-Amino-3-(1H-indol-3-yl)-propanoic acid D-tyrptophan (R)-2-Amino-3-(3-indolyl)propionic acid, D-α-Amino-3-indolepropionic acid D-Tryptophan,(R)-2-Amino-3-(3-indolyl)propionic acid, D-α-Amino-3-indolepropionic acid D-B-3-INDOLYLALANINE H-D-TYP-OH 3,3'-indolyl-2-alanine (R)-(+)-2-AMINO-3-(3-INDOLYL)PROPIONIC ACID (R)-2-AMINO-3-(3-INDOLYL)PROPIONIC ACID (r)-alpha-amino-3-indolepropionicacid (r)-alpha-aminoindole-3-propanoicacid (r)-tryptophan D-α-Amino-3-indolepropionic acid D-β-3-Indolyl alanine (S)-alph (S)-alpha-Amino-beta-indolepropionic acid (S)-Tryptophan 1H-Indole-3-alanine, (S)- d-tryptopha TRYPTOPHAN, D- D-Tryptophan-d5 D(+)-Tryptophan, 99+% 25GR D(+)-Tryptophan, 99+% 5GR (R)-α-AMino-3-indolepropionic Acid (R)-α-AMinoindole-3-propanoic Acid (2S)-2-amino-3-(1H-indol-3-yl)propionic acid Indoe-3-propionic acid, alpha-amino- L-Tryptophan (JP15) TRP-01 3,3'-Indolyl-2-alanin D(+)-Tryptophan (R)-2-Amino-3-(3-indolyl)propionic acid D-Tryptophan >