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56-69-9

Basic Information
CAS No.: 56-69-9
Name: Tryptophan, 5-hydroxy-
Molecular Structure:
Molecular Structure of 56-69-9 (Tryptophan, 5-hydroxy-)
Formula: C11H12N2O3
Molecular Weight: 220.25
Synonyms: DL-5-HTP;DL-5-Hydroxytryptophan;DL-Hydroxytryptophan;NSC 92523;
EINECS: 200-284-8
Density: 1.484 g/cm3
Melting Point: 298-300 °C
Boiling Point: 520.6 °C at 760 mmHg
Flash Point: 268.7 °C
Solubility: Soluble in water (4 mg/ml at 25°C), methanol.
Appearance: White powder
Hazard Symbols:
Risk Codes:
Safety: 24/25-22
Transport Information: UN 2811
PSA: 99.34000
LogP: 1.52820
Synthetic route

DL-tryptophan

56-69-9

5-hydroxytryptophan

Conditions
ConditionsYield
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
ConditionsYield
With potassium hydroxide In water Rate constant; Equilibrium constant; Irradiation;
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
ConditionsYield
With potassium hydroxide In water Rate constant; Equilibrium constant; Irradiation;
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
ConditionsYield
With potassium hydroxide In water Equilibrium constant; Irradiation;
126216-42-0

5-Hydroxytryptophan radical

108-46-3

recorcinol

A

24856-47-1

3-hydroxy-phenyloxyl

B

56-69-9

5-hydroxytryptophan

Conditions
ConditionsYield
With potassium hydroxide In water Equilibrium constant; Irradiation;
5-benzyloxy-DL-tryptophan

5-benzyloxy-DL-tryptophan

56-69-9

5-hydroxytryptophan

Conditions
ConditionsYield
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
ConditionsYield
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
ConditionsYield
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
ConditionsYield
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
ConditionsYield
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
ConditionsYield
With acetic acid at 60℃; for 15h;93.12%
67-56-1

methanol

56-69-9

5-hydroxytryptophan

5-hydroxytryptophan methyl ester

Conditions
ConditionsYield
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
ConditionsYield
With sulfuric acid In ethanol; water for 18h; Ambient temperature;91%
With acetic acid In methanol; water70%
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
ConditionsYield
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
ConditionsYield
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
ConditionsYield
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
ConditionsYield
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
ConditionsYield
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
ConditionsYield
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
ConditionsYield
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
ConditionsYield
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
ConditionsYield
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
ConditionsYield
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
ConditionsYield
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
ConditionsYield
With potassium hydroxide 1.) aq. isopropanol, 3 - 4 h, 2.) ether, hexane; Yield given. Multistep reaction;
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
ConditionsYield
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
ConditionsYield
With hydrogenchloride Multistep reaction;
56-69-9

5-hydroxytryptophan

50-67-9

3-(2-aminoethyl)-1H-indol-5-ol

Conditions
ConditionsYield
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
ConditionsYield
With hydrogenchloride at 25℃; Product distribution; Mechanism; electrochemical oxidation;
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
ConditionsYield
With potassium hydroxide In water Rate constant; Equilibrium constant; Irradiation;
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
ConditionsYield
With potassium hydroxide In water Equilibrium constant; Irradiation;
24856-47-1

3-hydroxy-phenyloxyl

56-69-9

5-hydroxytryptophan

A

126216-42-0

5-Hydroxytryptophan radical

B

108-46-3

recorcinol

Conditions
ConditionsYield
With potassium hydroxide In water Rate constant; Equilibrium constant; Irradiation;
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    5-HTP Quick details Chemical Name: 5-HTP CAS No.:56-69-9 Molecular Formula:C11H12N2O3 Molecular weight: 220.22 Appearance: white powder 5-HTP Specifications ANALYSI

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Consensus Reports

Reported in EPA TSCA Inventory.

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 NOx.

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,