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153-94-6

Basic Information
CAS No.: 153-94-6
Name: D(+)-Tryptophan
Article Data: 79
Cas Database
Molecular Structure:
Molecular Structure of 153-94-6 (D(+)-Tryptophan)
Formula: C11H12N2O2
Molecular Weight: 204.228
Synonyms: (R)-tryptophan;(+)-Tryptophan;(2R)-2-azaniumyl-3-(1H-indol-3-yl)propanoate;Tryptophan, D-;(2R)-2-amino-3-(1H-indol-3-yl)propanoic acid;H-D-Trp-OH;
EINECS: 205-819-9
Density: 1.362 g/cm3
Melting Point: 282-285 °C
Boiling Point: 447.9 °C at 760 mmHg
Flash Point: 224.7 °C
Solubility: 11 g/L (20 °C) in water
Appearance: White or yellow crystalline powder
Hazard Symbols: IrritantXi
Risk Codes: 36/37/38-41-37/38-22
Safety: 24/25-36/37/39-36-26
Transport Information: N/A
PSA: 79.11000
LogP: 1.82260
Synthetic route

C15H15N3*C18H14Cl2N2O3

153-94-6

D-tryptophan

Conditions
ConditionsYield
With benzylamine hydrochloride In water; isopropyl alcohol at 20℃; for 1h;95%
392-12-1

Indole-3-pyruvic acid

A

73-22-3

L-Tryptophan

B

153-94-6

D-tryptophan

Conditions
ConditionsYield
With CC10H14NOSCH2CH2CH3N(CH3)2 (5); zinc diacetate In methanol at 30℃; Product distribution; pH 4.00;A 6%
B 94%
With 5-((3-(dimethylamino)propyl)thio)-4-(aminomethyl)-3-hydroxyl-5,6,7,8-tetraquinoline In methanol at 30℃; Product distribution; stereoselective transaminations at pH=4.00, various reagents;A 6 % Chromat.
B 94 % Chromat.
With phosphate buffer; 6A-monoimidazolyl-6B-(5'-thiopyridoxaminyl)-β-D-cyclodextrin In water at 25℃; Product distribution; other reragents, various pH;
120-72-9

indole

56-45-1

L-serin

153-94-6

D-tryptophan

Conditions
ConditionsYield
Stage #1: indole; L-serin With Salmonella enterica tryptophan synthase In methanol; aq. phosphate buffer at 37℃; pH=8.0; Enzymatic reaction;
Stage #2: With (2R)-aspartic acid In methanol; aq. phosphate buffer pH=8.0;
Stage #3: In aq. phosphate buffer; deuteromethanol at 37℃; pH=8.0; Enzymatic reaction; stereoselective reaction;
69%
66872-76-2

β-(3-indolyl)-α-ketopropanoic acid sodium salt

153-94-6

D-tryptophan

Conditions
ConditionsYield
With zinc(II) perchlorate; (S)-15-amino-methyl-14-hydroxy-5,5-dimethyl-2,8-dithia<9>(2,5)pyridinophane In methanol for 24h; Ambient temperature;62%
153-94-6

D-tryptophan

Conditions
ConditionsYield
With sodium hydroxide; oxygen; 2-amino-2-hydroxymethyl-1,3-propanediol In water at 30℃; for 8h; pH=7.3; Resolution of racemate; Enzymatic reaction; enantioselective reaction;48%

A

73-22-3

L-Tryptophan

B

153-94-6

D-tryptophan

Conditions
ConditionsYield
With Bis(2-ethylhexyl)phosphoric acid; sodium dodecyl-sulfate; O,O'-dibenzoyl-L-tartaric acid In octanol; water at 20℃; for 4h; Reflux; Resolution of racemate; optical yield given as %ee; enantioselective reaction;A n/a
B 18.59%
With (2R,3R,11R,12R)-(+)-18-crown-6-2,3,11,12-tetracarbonic acid In acetonitrile at 25℃; pH=3; Electrochemical reaction;
With teicoplanin In methanol; water Product distribution; Further Variations:; Reagents; pH-values; Solvents;
4299-70-1, 7303-49-3, 22032-65-1

D-Tryptophan methyl ester

153-94-6

D-tryptophan

Conditions
ConditionsYield
With barium dihydroxide; water
With methanol; barium dihydroxide
With Streptomyces spp. 82F2 D-aminopeptidase In dimethyl sulfoxide at 20℃; for 0.0833333h; pH=6.5; aq. buffer; Enzymatic reaction;
2280-01-5

N-acetyl-D-tryptophan

153-94-6

D-tryptophan

Conditions
ConditionsYield
With hydrogenchloride; water
With sulfuric acid; water
With barium dihydroxide; water
With D-aminoacylase; cobalt(II) chloride hexahydrate at 36 - 37℃; pH=7.4; aq. phosphate buffer; Enzymatic reaction;
742100-62-5

Nα-chloroacetyl-D-tryptophan

153-94-6

D-tryptophan

Conditions
ConditionsYield
With sulfuric acid; water
2279-15-4

N-(benzyloxycarbonyl)-D-tryptophan

153-94-6

D-tryptophan

Conditions
ConditionsYield
With methanol; palladium; acetic acid Hydrogenation;
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Reported in EPA TSCA Inventory.

Specification

The IUPAC name of D-Tryptophan is 2-amino-3-(1H-indol-3-yl)propanoic acid. With the CAS registry number 153-94-6, it is also named as (R)-a-Amino-3-indolepropionic Acid. The product's categories are Amino Acids Derivatives; Tryptophan [Trp, W]; Amino Acids and Derivatives; alpha-Amino Acids; Amino Acids; Biochemistry; Indoles; Tryptophans; Chiral Compound; Amino Acids. It is white or yellow crystalline powder which is soluble in hot ethanol, alkali solution and water, insoluble in chloroform. In addition, this chemical is combustible, stable and incompatible with oxidizing agents. Besides, it should be sealed in the container and stored in the cool and dry place.

The other characteristics of this product can be summarized as: (1)ACD/LogP: 1.04; (2)# of Rule of 5 Violations: 0; (3)ACD/LogD (pH 5.5): -1.46; (4)ACD/LogD (pH 7.4): -1.46; (5)ACD/BCF (pH 5.5): 1; (6)ACD/BCF (pH 7.4): 1; (7)ACD/KOC (pH 5.5): 1; (8)ACD/KOC (pH 7.4): 1; (9)#H bond acceptors: 4; (10)#H bond donors: 4; (11)#Freely Rotating Bonds: 4; (12)Index of Refraction: 1.697; (13)Molar Refractivity: 57.76 cm3; (14)Molar Volume: 149.8 cm3; (15)Polarizability: 22.9×10-24 cm3; (16)Surface Tension: 71.1 dyne/cm; (17)Enthalpy of Vaporization: 74.44 kJ/mol; (18)Vapour Pressure: 8.3E-09 mmHg at 25°C; (19)Rotatable Bond Count: 3; (20)Exact Mass: 204.089878; (21)MonoIsotopic Mass: 204.089878; (22)Topological Polar Surface Area: 79.1; (23)Heavy Atom Count: 15; (24)Complexity: 245.

Preparation of D-Tryptophan: Using DL-tryptophan as raw materials, and adding chloroacetic anhydride to react in cooling condition. Grinding in ice water after sulfuric acid acidizing. Then filtering and recrystallizing in water. Finally, treating with pancreatic carboxypeptidase to remove the L-type. Then we can get the product by acetic acid acidification and ethanol recrystallization.

Uses of of D-Tryptophan: It can used in biochemistry research. And it is an important nutrient which is used as controlling agent of bark favus in medication.

When you are using this chemical, please be cautious about it as the following:
It is not only harmful if swallowed, but also irritating to eyes, respiratory system and skin. So people should avoid contact with skin and eyes. In case of contact with eyes, rinse immediately with plenty of water and seek medical advice. If you want to contact this product, you must wear suitable protective clothing, gloves and eye/face protection.

People can use the following data to convert to the molecule structure.
1. SMILES:O=C(O)[C@H](N)Cc2c1ccccc1nc2
2. InChI:InChI=1/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

The following are the toxicity data which has been tested.

Organism Test Type Route Reported Dose (Normalized Dose) Effect Source
rat LD50 intraperitoneal 4289mg/kg (4289mg/kg) BEHAVIORAL: ALTERED SLEEP TIME (INCLUDING CHANGE IN RIGHTING REFLEX)

LUNGS, THORAX, OR RESPIRATION: DYSPNEA
Archives of Biochemistry and Biophysics. Vol. 64, Pg. 319, 1956.