DL-Tryptophan supplier | CasNO.54-12-6

Name
DL-Tryptophan
EINECS 200-194-9
CAS No. 54-12-6
Article Data62
CAS DataBase
Density 1.363 g/cm³
Solubility Water: 10 g/L (20 °C)
Melting Point 289-290 °C
Formula C₁₁H₁₂N₂O₂
Boiling Point 447.908 °C at 760 mmHg
Molecular Weight 204.228
Flash Point 224.687 °C
Transport Information
Appearance Wite or off-white powder or crystal
Safety 24/25-36/37/39-36-26
Risk Codes 22-36/37/38-37/38-41
Molecular Structure
Hazard Symbols Xi
Synonyms Tryptophan, DL-(8CI);Racemic tryptophan;1H-Indole-3-alanine;DL-Tryptophane;DL-a-Amino-3-indolepropionic acid;NSC 13118;CCRIS 719;UNII-X9U7434L7A;AI3-24395;DL-alpha-Amino-3-indolepropionic acid;(+-)-Tryptophan;
PSA 79.11000
LogP 1.82260

Synthetic route

: 70380-01-7
DL-γ-glutamaldehydic acid dimethyl acetal

: 59-88-1
phenylhydrazine hydrochloride

: 54-12-6
Trp

Conditions

Conditions	Yield
With sulfuric acid In water for 1h; Heating;	85%

: 104331-05-7
rac-3-(1H-indol-3-yl)-2-(benzoylamino)propionic acid methyl ester

: 54-12-6
Trp

Conditions

Conditions	Yield
In potassium hydroxide hydrolysis;	70%

: 60438-65-5
α-(hydroxyimino)-β-(indol-3-yl)propionic acid

: 54-12-6
Trp

Conditions

Conditions	Yield
With ethanol; nickel Hydrogenation;
With ammonia; water at 60℃;

: 117490-34-3
5-(3-indolylmethylene)hydantoin

: 54-12-6
Trp

Conditions

Conditions	Yield
With diammonium sulfide at 100℃;
With diammonium sulfide at 150℃;

: 860375-04-8
formylamino-indol-3-ylmethyl-malonic acid

: 54-12-6
Trp

Conditions

Conditions	Yield
With sodium hydroxide; water

: 4354-88-5
acetylamino-indol-3-ylmethyl-malonic acid

: 54-12-6
Trp

Conditions

Conditions	Yield
With sulfuric acid; water
Multi-step reaction with 2 steps 1: H2O 2: NaOH; water View Scheme

: 64258-95-3
ethyl 2-formamido-3-(3-indolyl)-2-carbethoxypropionate

: 54-12-6
Trp

Conditions

Conditions	Yield
With sodium hydroxide; water at 120℃; anschl. mit Essigsaeure;
Multi-step reaction with 2 steps 1: aq.-ethanolic NaOH 2: H2O; NaOH View Scheme

: 854885-91-9
Nα-ethoxycarbonyl-DL-tryptophan-nitrile

: 54-12-6
Trp

Conditions

Conditions	Yield
With hydrogenchloride; water; acetic acid

: indol-3-ylmethyl-phthalimido-malonic acid diethyl ester

: 54-12-6
Trp

Conditions

Conditions	Yield
With sodium hydroxide; water

: 149828-46-6
Nα-ethoxycarbonyl-DL-tryptophan-ethyl ester

: 54-12-6
Trp

Conditions

Conditions	Yield
With sodium hydroxide; ethanol; water

: 73-22-3
L-Tryptophan

: 54-12-6
Trp

Conditions

Conditions	Yield
With barium dihydroxide at 170℃; im Autoklaven;
With hydrogenchloride; ethanethiol at 110℃; Rate constant; various times;
With 0.1-diethanolamine-HCl buffer; cross-linked formylated phenol-formaldehyde resin at 70℃; Rate constant; other reagents;
With hydrogenchloride at 110℃; Product distribution; Kinetics; racemization reaction;

: 1218-34-4, 87-32-1
N-acetyl-DL-tryptophan

: 54-12-6
Trp

Conditions

Conditions	Yield
With barium dihydroxide; water
With sodium hydroxide; water
With water; sodium hydroxide at 85℃; for 1.5h; pH=9.5; pH-value; Temperature;	23.2 g
With sodium hydroxide; water

: 42717-06-6
acetyltryptophan ethylester

: 54-12-6
Trp

Conditions

Conditions	Yield
With sodium hydroxide; water

: 2901-79-3
2-(benzoylamino)-3-(indol-3-yl)propanoic acid

: 54-12-6
Trp

Conditions

Conditions	Yield
With barium dihydroxide; water

: 120-72-9
indole

: 302-84-1
serin

: 54-12-6
Trp

Conditions

Conditions	Yield
With N+C3(R/S-DHBN)(S-Ala)2C16; N+C5(S-Ala)2C16; PL+C2N2C16; copper(II) perchlorate In water at 30℃; for 200h; Product distribution; Mechanism; var. catalyst composition;

: 120-72-9
indole

: 3981-36-0
3-chloro-DL-alanine

: 54-12-6
Trp

Conditions

Conditions	Yield
With aluminum(III) sulfate; pyridoxal; β-cyclodextrin at 100℃; for 0.5h; pH=5.2;

: 120-72-9
indole

: 127-17-3
2-oxo-propionic acid

: 54-12-6
Trp

Conditions

Conditions	Yield
With sodium hydroxide; pyridoxal 5'-phosphate; ammonium chloride; Triton X-100 In ethanol at 32℃; for 72h; Enterobacter aerogenes L-12;

: 392-12-1
Indole-3-pyruvic acid

: 54-12-6
Trp

Conditions

Conditions	Yield
With pyridoxamine; β‐cyclodextrin pH 8, other reagent;
With methylated polyethyleneimine-lauryl supported pyridoxamine at 30℃; pH=7.5; Kinetics;

: 47355-10-2, 64905-10-8
Boc-Trp(For)

A: 74257-18-4
(+/-)-Nι-Formyltryptophan

B: 54-12-6
Trp

Conditions

Conditions	Yield
With p-cresol; dimethylsulfide; hydrogen fluoride at 0℃; for 1h; Product distribution; further reagent: EtSH, HSCH2CH2SH, p-thiocresol; var. time;	A 98 % Chromat. B 2 % Chromat.

: 85313-49-1, 145089-21-0
t-Bumeoc-Trp-OH

: 54-12-6
Trp

Conditions

Conditions	Yield
With formic acid; water; acetic acid for 0.0166667h; Product distribution; Ambient temperature; other reaction time;	21 % Chromat.

: 81084-87-9
isopropyl (+/-)-tryptophanoate

A: 67-63-0
isopropyl alcohol

B: 54-12-6
Trp

Conditions

Conditions	Yield
With water; β‐cyclodextrin In acetonitrile for 30h; Rate constant; Ambient temperature; var. pH, other β-cyclodextrin derivatives;

α-benzamino-β--acrylic acid: α-benzamino-β--acrylic acid

: 54-12-6
Trp

Conditions

Conditions	Yield
With ethanol; sodium Verseifen des Reaktionsprodukts durch Verduennen mit Wasser; dl-tryptophan;

(+-)-2-acetylamino-3-<2-ethoxycarbonyl-indol-3-yl>-propionic acid: (+-)-2-acetylamino-3-<2-ethoxycarbonyl-indol-3-yl>-propionic acid

: 54-12-6
Trp

Conditions

Conditions	Yield
With sulfuric acid; water
With sulfuric acid; water

(+-)-3-indol-3-yl-2-nitro-propionic acid ethyl ester: (+-)-3-indol-3-yl-2-nitro-propionic acid ethyl ester

: 54-12-6
Trp

Conditions

Conditions	Yield
With ethanol; nickel at 100℃; Hydrogenation.unter erhoehtem Druck; anschl. mit wss. NaOH;

(+-)-3-indol-3-yl-2-nitro-propionic acid methyl ester: (+-)-3-indol-3-yl-2-nitro-propionic acid methyl ester

: 54-12-6
Trp

Conditions

Conditions	Yield
With methanol; nickel at 80 - 90℃; Hydrogenation.unter erhoehtem Druck; anschl. mit wss. NaOH;

(+-)-5-indol-3-ylmethyl-imidazolidine-2,4-dione: (+-)-5-indol-3-ylmethyl-imidazolidine-2,4-dione

: 54-12-6
Trp

Conditions

Conditions	Yield
With barium dihydroxide; water
With sodium hydroxide; water
With barium dihydroxide; water

5--hydantoin: 5--hydantoin

: 54-12-6
Trp

Conditions

Conditions	Yield
With barium dihydroxide at 108℃;

: 67-56-1
methanol

: 54-12-6
Trp

: 5619-09-0, 7524-52-9, 14907-27-8, 26988-71-6, 41222-70-2, 67557-19-1, 109492-62-8
methyl tryptophanate hydrochloride

Conditions

Conditions	Yield
With hydrogenchloride; 3 A molecular sieve for 2.5h; Heating;	100%
With thionyl chloride at 10 - 25℃; Cooling with ice;	100%
With thionyl chloride at -15 - 20℃; for 24h; Saturated gas; Inert atmosphere;	92%

: 64-17-5
ethanol

: 54-12-6
Trp

: 6519-66-0, 7479-05-2, 74126-25-3
DL-tryptophan ethyl ester

Conditions

Conditions	Yield
Stage #1: ethanol; Trp With thionyl chloride Reflux; Stage #2: With sodium hydrogencarbonate	100%
With thionyl chloride at 0 - 80℃; Reflux;	91%
With thionyl chloride for 0.5h; Reflux;	76%

: 6674-22-2
1,8-diazabicyclo[5.4.0]undec-7-ene

: 54-12-6
Trp

: 2,3,4,6,7,8,9,10-octahydropyrimido[1,2-a]azepin-1-ium (D,L)-2-amino-3-(1H-indol-3-yl)propanoate

Conditions

Conditions	Yield
In dichloromethane at 20℃; for 20h;	100%

: 54-12-6
Trp

: 80-70-6
N,N,N',N'-tetramethylguanidine

: bis(dimethylamino)methaniminium DL-2-amino-3-(1H-indol-3-yl)propanoate

Conditions

Conditions	Yield
In dichloromethane at 20℃; for 23h;	100%

: 24424-99-5
di-tert-butyl dicarbonate

: 54-12-6
Trp

: 5241-64-5, 13139-14-5, 112525-72-1
BOC-tryptophane

Conditions

Conditions	Yield
With sodium hydroxide In 1,4-dioxane; water at 20℃; for 24h;	99%
With triethylamine In water at 45℃; for 12h; Solvent; Temperature;	95.1%
With sodium carbonate In 1,4-dioxane; water at 20℃;	91%

: nickel(II) nitrate hexahydrate

: (S)-N-(2-benzoyl-4-chlorophenyl)-2-(1-(1-adamantyl)ethylamino)acetamide

: 54-12-6
Trp

: C38H39ClN4NiO3

Conditions

Conditions	Yield
With potassium carbonate In methanol for 2h; Reflux;	99%

...Expand

: 54-12-6
Trp

: 154-09-6, 526-53-4, 2899-29-8, 52485-52-6
2-amino-3-(1H-indol-3-yl)propan-1-ol

Conditions

Conditions	Yield
With lithium aluminium tetrahydride In tetrahydrofuran for 15h; Heating;	98%
With tetrahydrofuran; lithium aluminium tetrahydride
With sodium tetrahydroborate; iodine In tetrahydrofuran Heating;
In tetrahydrofuran; ethyl acetate

: 32837-87-9
3-hydroxy-3-methyl-1-cyano-1-butyne

: 54-12-6
Trp

: 1257081-06-3
2-[(5-imino-2,2-dimethyl-2,5-dihydrofuran-3-yl)amino]-3-(1H-indol-3-yl)propanoic acid

Conditions

Conditions	Yield
Stage #1: Trp With sodium hydroxide In water at 40 - 45℃; pH=10; Stage #2: 3-hydroxy-3-methyl-1-cyano-1-butyne In water for 4h; pH=10; regioselective reaction;	98%

: 1644308-41-7
((S)-N-(2-benzoyl-4-chlorophenyl)-1-(3,4-dichlorobenzyl)pyrrolidine-2-carboxamide)

: 6018-89-9
nickel(II) acetate tetrahydrate

: 54-12-6
Trp

: C36H29Cl3N4NiO3

Conditions

Conditions	Yield
With potassium carbonate In methanol at 20℃; for 72h; Temperature; diastereoselective reaction;	98%

...Expand

: 67-56-1
methanol

: 54-12-6
Trp

: methyl 2-amino-3-(1H-indol-3-yl)propanoate hydrochloride

Conditions

Conditions	Yield
With thionyl chloride for 18h; Reflux;	98%
With thionyl chloride at 0 - 60℃;
With thionyl chloride

: 3-(4,4-difluoro-2,6-dimethyl-4-bora-3a,4a-diaza-s-indacene-8-yl)propionic acid succinimidyl ester

: 54-12-6
Trp

: N-(3-(4,4-difluoro-2,6-dimethyl-4-bora-3a,4a-diaza-s-indacene-8-yl)propanoyl)-DL-tryptophan

Conditions

Conditions	Yield
In dimethyl sulfoxide at 2℃; for 12h; pH=11;	98%

: 50-00-0
formaldehyd

: 54-12-6
Trp

: 6052-68-2
1,2,3,4-tetrahydro-β-carboline-3-carboxylic acid

Conditions

Conditions	Yield
With sodium hydroxide In water for 3h; Heating;	97%
In water at 37℃; Pictet-Spengler reaction;	95%
With sodium hydroxide In water at 37℃; Formylation;	90%

: 85-44-9
phthalic anhydride

: 54-12-6
Trp

: 32675-71-1
2-(1,3-dioxo-1,3-dihydroisoindol-2-yl)-3-(1H-indol-3-yl)propionic acid

Conditions

Conditions	Yield
With triethylamine In N,N-dimethyl-formamide for 8h; Reflux; Inert atmosphere;	97%
With pyridine
With pyridine for 18h; Reflux;	26.9 g

: 14387-17-8
3,5-di-tert-butyl-4-hydroxybenzyl acetate

: 54-12-6
Trp

: 2-(3,5-di-tert-butyl-4-hydroxybenzylamino)-3-(1H-indol-3-yl)propanoic acid

Conditions

Conditions	Yield
In dimethyl sulfoxide at 70℃; for 3h;	97%

: 890095-37-1
3-nitro-2-(trifluoromethyl)-2H-chromene

: 91-56-5
indole-2,3-dione

: 54-12-6
Trp

: (1S*,3S*,3aS*,4S*,9bR*)-3-[(1H-indol-3-yl)methyl]-3a-nitro-4-(trifluoromethyl)-2,3,3a,9b-tetrahydro-4H-spiro[chromeno[3,4-c]pyrrole-1,3'-indolin]-2'-one

Conditions

Conditions	Yield
In ethanol at 70℃; for 3h; diastereoselective reaction;	96%

...Expand

: 762-42-5
dimethyl acetylenedicarboxylate

: 54-12-6
Trp

: dimethyl 4-hydroxy-5-(1H-indol-3-ylmethyl)-1H-pyrrole-2,3-dicarboxylate

Conditions

Conditions	Yield
With dicyclohexyl-carbodiimide In N,N-dimethyl-formamide at 25℃; for 24h;	95%

: 762-21-0
acetylenedicarboxylic acid diethyl ester

: 54-12-6
Trp

: 1067227-64-8
diethyl 4-hydroxy-5-(1H-indol-3-ylmethyl)-1H-pyrrole-2,3-dicarboxylate

Conditions

Conditions	Yield
With dicyclohexyl-carbodiimide In N,N-dimethyl-formamide at 25℃; for 24h;	95%

: 32837-89-1
3-(1-hydroxycyclohexyl)prop-2-ynenitrile

: 54-12-6
Trp

: 1257081-08-5
2-[(2-imino-1-oxaspiro[4.5]dec-3-en-4-yl)amino]-3-(1H-indol-3-yl)propanoic acid

Conditions

Conditions	Yield
Stage #1: Trp With sodium hydroxide In water at 40 - 45℃; pH=10; Stage #2: 3-(1-hydroxycyclohexyl)prop-2-ynenitrile In water for 48h; pH=10; regioselective reaction;	95%

: 32837-90-4
3-hydroxy-3-tetramethylene-1-propynecarbonitrile

: 54-12-6
Trp

: 2-[(2-imino-1-oxaspiro[4.4]non-3-en-4-yl)amino]-3-(1H-indol-3-yl)propanoic acid

Conditions

Conditions	Yield
Stage #1: Trp With sodium hydroxide In water at 40 - 45℃; pH=10; Stage #2: 3-hydroxy-3-tetramethylene-1-propynecarbonitrile In water for 48h; pH=10; regioselective reaction;	95%

: (S)-N-(2-benzoyl-4-chlorophenyl)-2-[3,5-dihydro-4H-dinaphth[2,1-c:1′,2′-e]azepin-4-yl]acetamide

: 6018-89-9
nickel(II) acetate tetrahydrate

: 54-12-6
Trp

: C48H35ClN4NiO3

Conditions

Conditions	Yield
With potassium carbonate In methanol at 60 - 70℃; for 24h;	95%

...Expand

: 1217-89-6
1-benzylisatin

: 5706-12-7
(E)-2-benzylidene-2,3-dihydro-1H-inden-1-one

: 54-12-6
Trp

: C41H33N3O2

Conditions

Conditions	Yield
In dimethyl sulfoxide at 28℃; for 6h; Inert atmosphere; diastereoselective reaction;	95%

...Expand

: 67-56-1
methanol

: 54-12-6
Trp

: 7303-49-3
DL-tryptophan methyl ester

Conditions

Conditions	Yield
With thionyl chloride at 20℃;	94%
With hydrogenchloride
With thionyl chloride for 2h; Heating;

: 65-22-5
pyridoxal hydrochloride

: 54-12-6
Trp

: 13311-34-7
pyridoxylidenetryptophan Schiff base

Conditions

Conditions	Yield
In ethanol at 5℃;	94%
In ethanol; water at 25℃; pH=6.7 - 7.0;	75%

: 51673-84-8
dimethoxyacetaldehyde

: 54-12-6
Trp

: 1-(dimethoxymethyl)-2,3,4,9-tetrahydro-1H-pyrido[3,4-b]indole-3-carboxylic acid

Conditions

Conditions	Yield
With trifluoroacetic acid In dichloromethane for 1h;	94%
With trifluoroacetic acid In dichloromethane at 20℃; for 1h;	94%

: 122-51-0
orthoformic acid triethyl ester

: 54-12-6
Trp

: 3-(1H-indol-3-yl)-2-(1H-tetrazol-yl)propanoic acid

Conditions

Conditions	Yield
With sodium azide In water at 40℃; for 1h; Catalytic behavior; Solvent; Temperature; Concentration;	94%

: 54-12-6
Trp

: 5619-09-0, 7524-52-9, 14907-27-8, 26988-71-6, 41222-70-2, 67557-19-1, 109492-62-8
methyl tryptophanate hydrochloride

Conditions

Conditions	Yield
With thionyl chloride In methanol at 20℃;	92.54%
With thionyl chloride In methanol

: 85-42-7
1,2-Cyclohexanedicarboxylic acid-anhydride

: 54-12-6
Trp

: 2-(1,3-dioxooctahydroisoindol-2-yl)-3-(1H-indol-3-yl)propionic acid

Conditions

Conditions	Yield
With pyridine for 12h; Heating;	92%

: 1003573-84-9
6-methoxy-3-nitro-2-trifluoromethyl-2H-chromene

: 91-56-5
indole-2,3-dione

: 54-12-6
Trp

: (1S*,3S*,3aS*,4S*,9bR*)-3-[(1H-indol-3-yl)methyl]-8-methoxy-3a-nitro-4-(trifluoromethyl)-2,3,3a,9b-tetrahydro-4H-spiro[chromeno[3,4-c]pyrrole-1,3'-indolin]-2'-one

Conditions

Conditions	Yield
In ethanol at 70℃; for 3h; diastereoselective reaction;	91%

...Expand

: 117-80-6
2,3-Dichloro-1,4-naphthoquinone

: 54-12-6
Trp

: 2-((3-chloro-1,4-dioxo-1,4-dihydronaphthalen-2-yl)amino)-3-(1H-indol-3-yl)propanoic acid

Conditions

Conditions	Yield
Stage #1: Trp With triethylamine; potassium hydroxide In 1,4-dioxane; water at 110℃; for 0.166667h; Microwave irradiation; Stage #2: 2,3-Dichloro-1,4-naphthoquinone In 1,4-dioxane; water at 110℃; Microwave irradiation;	91%

: 54-12-6
Trp

: 343-94-2
tryptamine hydochloride

Conditions

Conditions	Yield
With hydrogenchloride In various solvent(s) for 0.333333h; Heating;	90%
With hydrogenchloride In various solvent(s) for 0.333333h; Heating;	72%

DL-Tryptophan Consensus Reports

Reported in EPA TSCA Inventory. EPA Genetic Toxicology Program.

DL-Tryptophan Specification

The DL-Tryptophan with CAS registry number of 54-12-6 is also known as Tryptophan. The IUPAC name is 2-Amino-3-(1H-indol-3-yl)propanoic acid. It belongs to product categories of Amino Acids Derivatives; Tryptophan [Trp, W]; alpha-Amino Acids; Amino Acids; Biochemistry; Indoles; Tryptophans; Alphabetical Listings; Stable Isotopes. Its EINECS registry number is 200-194-9. In addition, the formula is C₁₁H₁₂N₂O₂ and the molecular weight is 204.23. This chemical is a white or off-white powder or crystal and should be stored in sealed containers away from light.

Physical properties about DL-Tryptophan are: (1)ACD/LogP: 0.70; (2)ACD/BCF (pH 5.5): 1; (3)ACD/BCF (pH 7.4): 1; (4)ACD/KOC (pH 5.5): 1; (5)ACD/KOC (pH 7.4): 1; (6)#H bond acceptors: 4; (7)#H bond donors: 4; (8)#Freely Rotating Bonds: 4; (9)Index of Refraction: 1.698; (10)Molar Refractivity: 57.769 cm³; (11)Molar Volume: 149.875 cm³; (12)Surface Tension: 71.162 dyne/cm; (13)Density: 1.363 g/cm³; (14)Flash Point: 224.687 °C; (15)Enthalpy of Vaporization: 74.437 kJ/mol; (16)Boiling Point: 447.908 °C at 760 mmHg.

Preparation of DL-Tryptophan: it is prepared by reaction of indole with α-acetyl amino acid. Firstly, the reaction occurs with media of glacial acetic acid and acetic anhydride. After the reaction, the mixture solution is adjusted to alkaline by NaOH and extracted by ether. Secondly, the reaction mixture is extracted by dilute sodium hydroxide for three times. The sodium hydroxide solution is combined and a few grains of sodium bisulfite is added to the solution. Acetyl-DL-tryptophan is generated by cooling and adding concentrated hydrochloric acid. At last, acetyl-DL-tryptophan is refluxed with 10% sodium hydroxide solution to obtain the product.

Uses of DL-Tryptophan: it is not only used for biochemical research but also used as nutritional supplement and antioxidant. it is used to produce 2-indol-3-yl-ethylamine. The reaction occurs with solvent diphenyl ether and other condition of heating for 10 hours. The yield is about 63%.

DL-Tryptophan is used to produce 2-indol-3-yl-ethylamine.

When you are using this chemical, please be cautious about it. As a chemical, it is irritating to eyes, respiratory system and skin. What's more, it is harmful if swallowed and has risk of serious damage to eyes. During using it, wear suitable protective clothing, gloves and eye/face protection. Avoid contact with skin and eyes. If contact with eyes accidently, rinse immediately with plenty of water and seek medical advice.

You can still convert the following datas into molecular structure:
1. Canonical SMILES: C1=CC=C2C(=C1)C(=CN2)CC(C(=O)O)N
2. InChI: 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)
3. InChIKey: QIVBCDIJIAJPQS-UHFFFAOYSA-N

The toxicity data is as follows:

Organism	Test Type	Route	Reported Dose (Normalized Dose)	Effect	Source
mouse	LD50	intraperitoneal	> 1gm/kg (1000mg/kg)		Biochemical Pharmacology. Vol. 15, Pg. 2134, 1966.

Product Name

DL-Tryptophan

Synthetic route

DL-Tryptophan Consensus Reports

DL-Tryptophan Specification

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