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56-69-9

Basic Information
CAS No.: 56-69-9
Name: Tryptophan, 5-hydroxy-
Article Data: 19
Cas Database
Molecular Structure:
Molecular Structure of 56-69-9 (Tryptophan, 5-hydroxy-)
Formula: C11H12N2O3
Molecular Weight: 220.228
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: N/A
Risk Codes: N/A
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%
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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,