5-Hydroxytryptophan supplier

Name
5-Hydroxytryptophan
EINECS 200-284-8
CAS No. 56-69-9
Article Data19
CAS DataBase
Density 1.484 g/cm³
Solubility Soluble in water (4 mg/ml at 25°C), methanol.
Melting Point 298-300 °C
Formula C₁₁H₁₂N₂O₃
Boiling Point 520.6 °C at 760 mmHg
Molecular Weight 220.228
Flash Point 268.7 °C
Transport Information UN 2811
Appearance White powder
Safety 24/25-22
Risk Codes
Molecular Structure
Hazard Symbols
Synonyms DL-5-HTP;DL-5-Hydroxytryptophan;DL-Hydroxytryptophan;NSC 92523;
PSA 99.34000
LogP 1.52820

Synthetic route

: DL-tryptophan

: 56-69-9
5-hydroxytryptophan

Conditions

Conditions	Yield
With mannitol; succinic acid; Claviceps sp. PRL 1980 In water at 25℃; for 360h;

: 100-22-1
N,N,N',N'-tetramethyl-para-phenylenediamine

: 126216-42-0
5-Hydroxytryptophan radical

A: 100-22-1
N,N,N',N'-Tetramethyl-benzene-1,4-diamine

B: 56-69-9
5-hydroxytryptophan

Conditions

Conditions	Yield
With potassium hydroxide In water Rate constant; Equilibrium constant; Irradiation;

...Expand

: 619-60-3
4-(N,N-dimethylamino)phenol

: 126216-42-0
5-Hydroxytryptophan radical

A: 54737-34-7
4-(N,N-dimethylamino)phenoxyl radical

B: 56-69-9
5-hydroxytryptophan

Conditions

Conditions	Yield
With potassium hydroxide In water Rate constant; Equilibrium constant; Irradiation;

...Expand

: 126216-42-0
5-Hydroxytryptophan radical

: 150-76-5
4-methoxy-phenol

A: 6119-32-0
4-methoxyphenoxyl

B: 56-69-9
5-hydroxytryptophan

Conditions

Conditions	Yield
With potassium hydroxide In water Equilibrium constant; Irradiation;

...Expand

: 126216-42-0
5-Hydroxytryptophan radical

: 108-46-3
recorcinol

A: 24856-47-1
3-hydroxy-phenyloxyl

B: 56-69-9
5-hydroxytryptophan

Conditions

Conditions	Yield
With potassium hydroxide In water Equilibrium constant; Irradiation;

...Expand

5-benzyloxy-DL-tryptophan: 5-benzyloxy-DL-tryptophan

: 56-69-9
5-hydroxytryptophan

Conditions

Conditions	Yield
With ethanol; palladium Hydrogenation;
With sodium hydroxide; palladium Hydrogenation;

: 67-56-1
methanol

: 56-69-9
5-hydroxytryptophan

: 163108-63-2
5-hydroxytryptophan methyl ester hydrochloride

Conditions

Conditions	Yield
With thionyl chloride at 0 - 20℃; for 17h; Under N2;	100%
With thionyl chloride at 50℃; for 7.16h; Inert atmosphere; Cooling with ice;	99.2%

: 85-44-9
phthalic anhydride

: 56-69-9
5-hydroxytryptophan

: 2-(1,3-dioxoisoindolin-2-yl)-3-(5-hydroxy-1H-indol-3-yl)-propanoic acid

Conditions

Conditions	Yield
With triethylamine In N,N-dimethyl-formamide at 140℃; for 4h;	96%

: 67-56-1
methanol

: 56-69-9
5-hydroxytryptophan

: 5-hydroxytryptophan methyl ester hydrochloride

Conditions

Conditions	Yield
With hydrogenchloride In dimethyl sulfoxide at 0 - 20℃; for 3.75h; Reflux;	96%

: 58632-95-4
2-(tert-Butoxycarbonyloxyimino)-2-phenylacetonitrile

: 56-69-9
5-hydroxytryptophan

: 2-((tert-butoxycarbonyl)amino)-3-(5-hydroxy-1H-indol-3-yl)propanoic acid

Conditions

Conditions	Yield
With triethylamine In 1,4-dioxane; water at 20℃; Inert atmosphere;	94%

: 108-30-5
succinic acid anhydride

: 56-69-9
5-hydroxytryptophan

: N-[1-carboxy-2-(5-hydroxy-1H-indol-3-yl)-ethyl] succinamic acid

Conditions

Conditions	Yield
With acetic acid at 60℃; for 15h;	93.12%

: 67-56-1
methanol

: 56-69-9
5-hydroxytryptophan

: 5-hydroxytryptophan methyl ester

Conditions

Conditions	Yield
With thionyl chloride at -5 - 25℃;	92.9%

: 50-00-0
formaldehyd

: 56-69-9
5-hydroxytryptophan

: 82637-88-5
(-)-(3S)-6-hydroxy-1,2,3,4-tetrahydro-β-carboline-3-carboxylic acid

Conditions

Conditions	Yield
With sulfuric acid In ethanol; water for 18h; Ambient temperature;	91%
With acetic acid In methanol; water	70%

: 80149-80-0
2-(Trimethylsilyl)ethyl 4-nitrophenyl carbonate

: 56-69-9
5-hydroxytryptophan

: 3-(5-Hydroxy-1H-indol-3-yl)-2-(2-trimethylsilanyl-ethylamino)-propionic acid

Conditions

Conditions	Yield
With TEA In methanol Ambient temperature;	91%

: 123-51-3
i-Amyl alcohol

: 56-69-9
5-hydroxytryptophan

: 1226517-32-3
5-hydroxytryptophan isoamyl ester

Conditions

Conditions	Yield
Stage #1: i-Amyl alcohol; 5-hydroxytryptophan With hydrogenchloride In diethyl ether for 22h; Fischer-Speier esterification method; Reflux; Stage #2: With ammonium hydroxide In dichloromethane; water	91%

: 1711-07-5
3-fluorobenzoyl chloride

: 56-69-9
5-hydroxytryptophan

: 2-(3-fluorobenzoylamino)-3-(5-hydroxy-1H-indol-3-yl)propionic acid

Conditions

Conditions	Yield
With sodium hydroxide In water at 0℃; for 1h; pH=9 - 10;	82.1%

: 106-31-0
butanoic acid anhydride

: 56-69-9
5-hydroxytryptophan

: 2-butyrylamino-3-(5-hydroxy-1H-indol-3-yl)propionic acid

Conditions

Conditions	Yield
With sodium hydroxide In water at 0 - 20℃; for 1h; pH=9 - 10;	82.1%

: 108-24-7
acetic anhydride

: 56-69-9
5-hydroxytryptophan

: 92580-87-5
(RS)-5-acetoxy-N-acetyltryptophan

Conditions

Conditions	Yield
With sodium hydroxide at 0℃; for 2.5h;	75%

: 115-18-4
2-methyl-3-buten-2-ol

: 56-69-9
5-hydroxytryptophan

: 1312777-96-0
dl-5-hydroxy-N-(3-methyl-2-buten-1-yl)tryptophan

Conditions

Conditions	Yield
With sodium acetate; palladium diacetate; sodium 3-(diphenylphosphanyl)benzenesulfonate In water at 120℃; for 38h; Sealed tube;	57%

: 81329-81-9
EDTA monoanhydride

: 56-69-9
5-hydroxytryptophan

: 2-(2-{[2-(bis-carboxymethyl-amino)-ethyl]-carboxymethyl-amino}-acetylamino)-3-(5-hydroxy-1H-indol-3-yl)-propionic acid

Conditions

Conditions	Yield
In N,N-dimethyl-formamide for 3h;	52%

: 2835-06-5
phenylglycin

: 56-69-9
5-hydroxytryptophan

: 1-phenyl-9H-pyrido[3,4-b]indol-6-ol

Conditions

Conditions	Yield
With iodine; trifluoroacetic acid In dimethyl sulfoxide at 120℃; for 24h; Green chemistry;	46%

: 108-24-7
acetic anhydride

: 56-69-9
5-hydroxytryptophan

: 19367-81-8
N-acetyl-5-hydroxy-tryptophan

Conditions

Conditions	Yield
With N-ethyl-N,N-diisopropylamine In acetonitrile at 20℃; for 16h;	32%
In methanol at 40℃; for 16h;	26%

: 64-17-5
ethanol

: 56-69-9
5-hydroxytryptophan

: 43157-32-0
5-hydroxytryptophan esthyl ester

Conditions

Conditions	Yield
Stage #1: ethanol; 5-hydroxytryptophan With hydrogenchloride In diethyl ether at 88℃; for 24h; Fischer-Speier esterification method; Stage #2: With ammonium hydroxide In dichloromethane; water	29%

: 56-69-9
5-hydroxytryptophan

: 43157-32-0
5-hydroxytryptophan esthyl ester

Conditions

Conditions	Yield
With hydrogenchloride

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

: 101-83-7
N-cyclohexyl-cyclohexanamine

: 56-69-9
5-hydroxytryptophan

: 82774-76-3
N,O-di-Boc-DL-5-hydroxytryptophan dicyclohexylammonium salt

Conditions

Conditions	Yield
With potassium hydroxide 1.) aq. isopropanol, 3 - 4 h, 2.) ether, hexane; Yield given. Multistep reaction;

...Expand

: 123-38-6
propionaldehyde

: 56-69-9
5-hydroxytryptophan

: (1S,3S)-1-Ethyl-6-hydroxy-2,3,4,9-tetrahydro-1H-β-carboline-3-carboxylic acid

Conditions

Conditions	Yield
With sulfuric acid at 25℃;

: 67-56-1
methanol

: 79-22-1
methyl chloroformate

: 56-69-9
5-hydroxytryptophan

: 72458-76-5, 93713-61-2
(2R,3aS,8aS)-8-Acetyl-5-hydroxy-3,3a,8,8a-tetrahydro-2H-pyrrolo[2,3-b]indole-1,2-dicarboxylic acid dimethyl ester

Conditions

Conditions	Yield
With hydrogenchloride Multistep reaction;

...Expand

: 56-69-9
5-hydroxytryptophan

: 50-67-9
3-(2-aminoethyl)-1H-indol-5-ol

Conditions

Conditions	Yield
With pyridoxal 5'-phosphate mammalian aromatic L-amino acid decarboxylase;
With Papaver somniferum tyrosine decarboxylase S372G mutant In aq. phosphate buffer at 25℃; pH=7.5; Kinetics; Reagent/catalyst; Enzymatic reaction;

: 56-69-9
5-hydroxytryptophan

A: tryptophan-4,5-dione

B: 4-<4-(6-hydroxyquinolyl)>-5-hydroxytryptophan

C: 4,4'-bis(5-hydroxytryptophan)

Conditions

Conditions	Yield
With hydrogenchloride at 25℃; Product distribution; Mechanism; electrochemical oxidation;

...Expand

: 6119-32-0
4-methoxyphenoxyl

: 56-69-9
5-hydroxytryptophan

A: 126216-42-0
5-Hydroxytryptophan radical

B: 150-76-5
4-methoxy-phenol

Conditions

Conditions	Yield
With potassium hydroxide In water Rate constant; Equilibrium constant; Irradiation;

...Expand

: 54737-34-7
4-(N,N-dimethylamino)phenoxyl radical

: 56-69-9
5-hydroxytryptophan

A: 619-60-3
4-(N,N-dimethylamino)phenol

B: 126216-42-0
5-Hydroxytryptophan radical

Conditions

Conditions	Yield
With potassium hydroxide In water Equilibrium constant; Irradiation;

...Expand

: 24856-47-1
3-hydroxy-phenyloxyl

: 56-69-9
5-hydroxytryptophan

A: 126216-42-0
5-Hydroxytryptophan radical

B: 108-46-3
recorcinol

Conditions

Conditions	Yield
With potassium hydroxide In water Rate constant; Equilibrium constant; Irradiation;

...Expand

5-Hydroxytryptophan Consensus Reports

Reported in EPA TSCA Inventory.

5-Hydroxytryptophan Specification

The 5-HTP is an organic compound with the formula C₁₁H₁₂N₂O₃. The IUPAC name of this chemical is 2-amino-3-(5-hydroxy-1H-indol-3-yl)propanoic acid. With the CAS registry number 56-69-9 and EINECS 200-284-8, it is also named as 5-Hydroxytryptophan. The product's category is Standard Extract. In addition, when using it, people should not breathe dust and avoid contact with skin and eyes. When heated to decomposition it emits toxic fumes of NO_x.

The other characteristics of this product can be summarized as: (1)ACD/LogP: -0.14; (2)# of Rule of 5 Violations: 1; (3)ACD/LogD (pH 5.5): -2.63; (4)ACD/LogD (pH 7.4): -2.64; (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: 5; (10)#H bond donors: 5; (11)#Freely Rotating Bonds: 5; (12)Polar Surface Area: 43.7 Å²; (13)Index of Refraction: 1.737; (14)Molar Refractivity: 59.65 cm³; (15)Molar Volume: 148.3 cm³; (16)Surface Tension: 85 dyne/cm; (17)Enthalpy of Vaporization: 83.55 kJ/mol; (18)Vapour Pressure: 1.15E-11 mmHg at 25°C; (19)Rotatable Bond Count: 3; (20)Tautomer Count: 9; (21)Exact Mass: 220.084792; (22)MonoIsotopic Mass: 220.084792; (23)Topological Polar Surface Area: 99.3; (24)Heavy Atom Count: 16; (25)Complexity: 272.

Uses of 5-HTP: It is used as an antidepressant, appetite suppressant, and sleep aid. The psychoactive action of 5-HTP is derived from its effect on the production of serotonin in central nervous system tissue. More specifically, 5-HTP increases the production of serotonin.

People can use the following data to convert to the molecule structure.
1. SMILES:O=C(O)C(N)Cc2c1cc(O)ccc1nc2
2. InChI:InChI=1/C11H12N2O3/c12-9(11(15)16)3-6-5-13-10-2-1-7(14)4-8(6)10/h1-2,4-5,9,13-14H,3,12H2,(H,15,16)
3. InChIKey:LDCYZAJDBXYCGN-UHFFFAOYAF

The following are the toxicity data which has been tested.

Organism	Test Type	Route	Reported Dose (Normalized Dose)	Effect	Source
mouse	LD50	intraperitoneal	200mg/kg (200mg/kg)		National Technical Information Service. Vol. AD277-689,

Product Name

5-Hydroxytryptophan

Synthetic route

5-Hydroxytryptophan Consensus Reports

5-Hydroxytryptophan Specification

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