Conditions | Yield |
---|---|
Stage #1: indol-5-ol; L-serin With pyridoxal 5'-phosphate; thermotoga maritima with tryptophan synthase β-subunit from pyrococcus furiosus M145T N167D mutant In aq. phosphate buffer; water; dimethyl sulfoxide at 75℃; for 2h; pH=8; Sealed tube; Enzymatic reaction; Stage #2: With hydrogenchloride In water | 93% |
With transformed Escherichia coli cells at 37℃; for 24h; | 70 % Chromat. |
With tryptophan synthase; pyridoxal 5'-phosphate at 37℃; for 24h; pH=7.8; Enzymatic reaction; |
DL-5-hydroxytryptophane amide
L-5-HTP
Conditions | Yield |
---|---|
43% | |
43% |
L-Tryptophan
A
7-Hydroxy-L-tryptophan
B
4-Hydroxy-L-tryptophan
C
(S)-6-hydroxytryptophan
D
L-5-HTP
Conditions | Yield |
---|---|
With dihydrogen peroxide; edetate disodium; iron(II) sulfate; ascorbic acid In water at 22℃; for 0.0416667h; | A n/a B 10% C n/a D 12% |
Conditions | Yield |
---|---|
With ethanol; palladium Hydrogenation; |
Conditions | Yield |
---|---|
Multi-step reaction with 2 steps 1: quinine 2: palladium; ethanol / Hydrogenation View Scheme |
L-Tryptophan
A
tryptamine
B
L-kynurenine
F
2-amino-3-(2-oxoindolin-3-yl)propanoic acid
G
L-5-HTP
Conditions | Yield |
---|---|
With dihydrogen peroxide at 37℃; for 6h; pH=4.6; Darkness; aq. borate buffer; |
Conditions | Yield |
---|---|
With tryptophan hydroxylase Enzymatic reaction; | |
With ferrous ammonium sulphate; 6-methyl-5,6,7,8-tetrahydrobopterin; tryptophan hydroxylase; oxygen In aq. buffer at 20℃; for 0.333333h; pH=7.7; Kinetics; Mechanism; Catalytic behavior; Reagent/catalyst; Solvent; Temperature; Enzymatic reaction; chemoselective reaction; |
Conditions | Yield |
---|---|
With thionyl chloride at -5 - 20℃; for 16h; | 98% |
With thionyl chloride at 0 - 20℃; Inert atmosphere; | 74% |
Conditions | Yield |
---|---|
With pyridoxal 5'-phosphate; aromatic L-amino acid decarboxylase In various solvent(s) at 30℃; for 48h; | 97% |
With NH4OH-NH4Cl buffer; pyridoxal 5'-phosphate at 30℃; for 0.5h; relative rate of CO2 evolution by aromatic L-amino acid decarboxylase from Micrococcus percitreus; | |
With isopropyl β-D-thiogalactoside; L-tryptophan decarboxylase in recombinant Escherichia coli at 28℃; |
Conditions | Yield |
---|---|
With pyridine | 97% |
methanol
L-5-HTP
2-amino-3-(5-hydroxy-1H-indol-3-yl)propionic acid methyl ester
Conditions | Yield |
---|---|
With thionyl chloride at 0 - 40℃; for 10h; | 95% |
With thionyl chloride at -5 - 35℃; for 5h; | 92.9% |
With hydrogenchloride at 0 - 20℃; for 18h; Fischer esterification; |
Conditions | Yield |
---|---|
In methanol for 3h; Reflux; | 89% |
Conditions | Yield |
---|---|
With pyridine; triethylamine In tetrahydrofuran for 2.5h; | 89% |
di-tert-butyl dicarbonate
L-5-HTP
(S)-2-tert-butoxycarbonylamino-3-(5-tert-butoxycarbonyloxy-1H-indol-3-yl)propionic acid
Conditions | Yield |
---|---|
With potassium hydroxide In isopropyl alcohol for 5h; pH=11.5 - 12.0; | 87% |
L-5-HTP
Conditions | Yield |
---|---|
In methanol for 3h; Reflux; | 86% |
2,6-difluorophenylisothiocyanate
L-5-HTP
Conditions | Yield |
---|---|
With pyridine; triethylamine In tetrahydrofuran for 3h; | 85% |
2,4-diflurophenylisocyanate
L-5-HTP
Conditions | Yield |
---|---|
With pyridine; triethylamine In tetrahydrofuran for 4h; | 85% |
Conditions | Yield |
---|---|
In methanol for 3h; Reflux; | 84.8% |
L-5-HTP
Conditions | Yield |
---|---|
In methanol for 3h; Reflux; | 84% |
Conditions | Yield |
---|---|
With pyridine; triethylamine In tetrahydrofuran for 4h; | 83% |
L-5-HTP
Conditions | Yield |
---|---|
In methanol for 3h; Reflux; | 82.8% |
Conditions | Yield |
---|---|
In methanol for 3h; Reflux; | 82.6% |
L-5-HTP
Conditions | Yield |
---|---|
In methanol for 3h; Reflux; | 82.6% |
L-5-HTP
Conditions | Yield |
---|---|
In methanol for 3h; Reflux; | 82.6% |
methanol
di-tert-butyl dicarbonate
L-5-HTP
(S)-methyl 2-((tert-butoxycarbonyl)amino)-3-(5-hydroxy-1H-indol-3-yl)propanoate
Conditions | Yield |
---|---|
Stage #1: methanol; L-5-HTP With thionyl chloride at 0 - 20℃; for 12h; Stage #2: di-tert-butyl dicarbonate With triethylamine In dichloromethane at 0 - 20℃; for 6h; | 82% |
Conditions | Yield |
---|---|
With pyridine; triethylamine In tetrahydrofuran for 3h; | 82% |
3-indolylglyoxal
L-5-HTP
6-hydroxy-1-(1H-indole-3-carbonyl)-2,3,4,9-tetrahydro-1H-pyrido[3,4-b]indole-3-carboxylic acid
Conditions | Yield |
---|---|
Stage #1: 3-indolylglyoxal; L-5-HTP With sulfuric acid In water at 20℃; for 10h; Pictet-Spengler cyclisation; Stage #2: With ammonia In water at 0℃; for 12h; pH=6 - 7; | 80% |
Conditions | Yield |
---|---|
With pyridine; triethylamine In tetrahydrofuran for 3h; | 80% |
Conditions | Yield |
---|---|
With pyridine; triethylamine In tetrahydrofuran | 79% |
3-chloro-4-fluorophenyl isothiocyanate
L-5-HTP
Conditions | Yield |
---|---|
With pyridine; triethylamine In tetrahydrofuran for 4h; | 79% |
Conditions | Yield |
---|---|
With pyridine; triethylamine In tetrahydrofuran for 3.5h; | 78% |
Conditions | Yield |
---|---|
In methanol for 3h; Reflux; | 77.2% |
Conditions | Yield |
---|---|
In water at 100℃; for 0.5h; | 77% |
di-tert-butyl dicarbonate
L-5-HTP
(S)-2-((tert-butoxycarbonyl)amino)-3-(5-hydroxy-1H-indol-3-yl)propanoic acid
Conditions | Yield |
---|---|
With potassium carbonate In tetrahydrofuran; water at 20℃; for 2h; | 76% |
Stage #1: di-tert-butyl dicarbonate; L-5-HTP With sodium hydrogencarbonate In water at 0 - 35℃; for 24h; Stage #2: With citric acid In water pH=6; | 58.16% |
With triethylamine In 1,4-dioxane at 20℃; |
Conditions | Yield |
---|---|
In trifluoroacetic acid ligand was added to Ru-complex in CF3COOH, stirred for 12 h at 50°C; pptd. with Et2O, dried in vac.; elem. anal.; | 75% |
Conditions | Yield |
---|---|
With pyridine; triethylamine In tetrahydrofuran for 3.5h; | 75% |
Molecular Formula: C11H12N2O3
Molecular Weight: 220.22
EINECS: 224-411-1
Flash piont: 175 °F
Refractive index: n20/D 1.4850(lit.)
Melting Point: 270 °C (dec.)(lit.)
Density: 0.902 g/mL at 25 °C(lit.)
Appearance: White to pale grey powder
Alpha: -32.5 º (c=1,H2O on dry basis)
Melting point: 270 °C (dec.)(lit.)
Storage tempreture: 2-8 °C
Water solubility: 10 mg/mL
Appearance: Colorless to pale pink crystals
Structure of L-5-Hydroxytryptophan (CAS NO.4350-09-8):
IUPAC Name: (2S)-2-Amino-3-(5-hydroxy-1H-indol-3-yl)propanoic acid
Canonical SMILES: C1=CC2=C(C=C1O)C(=CN2)CC(C(=O)O)N
Isomeric SMILES: C1=CC2=C(C=C1O)C(=CN2)C[C@@H](C(=O)O)N
InChI: InChI=1S/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)/t9-/m0/s1
InChIKey: LDCYZAJDBXYCGN-VIFPVBQESA-N
Product Category of L-5-Hydroxytryptophan (CAS NO.4350-09-8): Pharmaceutical Raw Materials;Indoles and derivatives;Tryptophan [Trp, W];Biochemistry;Biological-modified Amino Acids;Indoles;Tryptophans;Natural Plant Extract;Biochemicals Found in Plants;Nutrition Research;Tryptophan Derivatives;Unnatural Amino Acid Derivatives
L-5-Hydroxytryptophan (CAS NO.4350-09-8) is used as an antidepressant, appetite suppressant, and sleep aid.
Organism | Test Type | Route | Reported Dose (Normalized Dose) | Effect | Source |
---|---|---|---|---|---|
mouse | LD50 | intraperitoneal | 298mg/kg (298mg/kg) | SENSE ORGANS AND SPECIAL SENSES: LACRIMATION: EYE BEHAVIORAL: TREMOR BEHAVIORAL: CONVULSIONS OR EFFECT ON SEIZURE THRESHOLD | Iyakuhin Kenkyu. Study of Medical Supplies. Vol. 6, Pg. 307, 1975. |
mouse | LD50 | intravenous | 375mg/kg (375mg/kg) | BEHAVIORAL: SOMNOLENCE (GENERAL DEPRESSED ACTIVITY) BEHAVIORAL: ATAXIA BEHAVIORAL: EXCITEMENT | Nippon Yakurigaku Zasshi. Japanese Journal of Pharmacology. Vol. 69, Pg. 523, 1973. |
mouse | LD50 | oral | 1708mg/kg (1708mg/kg) | SENSE ORGANS AND SPECIAL SENSES: LACRIMATION: EYE BEHAVIORAL: TREMOR BEHAVIORAL: CONVULSIONS OR EFFECT ON SEIZURE THRESHOLD | Iyakuhin Kenkyu. Study of Medical Supplies. Vol. 6, Pg. 307, 1975. |
mouse | LD50 | subcutaneous | 418mg/kg (418mg/kg) | SENSE ORGANS AND SPECIAL SENSES: LACRIMATION: EYE BEHAVIORAL: CONVULSIONS OR EFFECT ON SEIZURE THRESHOLD BEHAVIORAL: TREMOR | Iyakuhin Kenkyu. Study of Medical Supplies. Vol. 6, Pg. 307, 1975. |
rabbit | LD50 | oral | 285mg/kg (285mg/kg) | SENSE ORGANS AND SPECIAL SENSES: LACRIMATION: EYE BEHAVIORAL: TREMOR BEHAVIORAL: CONVULSIONS OR EFFECT ON SEIZURE THRESHOLD | Iyakuhin Kenkyu. Study of Medical Supplies. Vol. 6, Pg. 307, 1975. |
rat | LD50 | intraperitoneal | 91mg/kg (91mg/kg) | BEHAVIORAL: SOMNOLENCE (GENERAL DEPRESSED ACTIVITY) BEHAVIORAL: EXCITEMENT BEHAVIORAL: ATAXIA | Nippon Yakurigaku Zasshi. Japanese Journal of Pharmacology. Vol. 69, Pg. 523, 1973. |
rat | LD50 | intravenous | 27mg/kg (27mg/kg) | SENSE ORGANS AND SPECIAL SENSES: LACRIMATION: EYE BEHAVIORAL: TREMOR BEHAVIORAL: CONVULSIONS OR EFFECT ON SEIZURE THRESHOLD | Iyakuhin Kenkyu. Study of Medical Supplies. Vol. 6, Pg. 307, 1975. |
rat | LD50 | oral | 243mg/kg (243mg/kg) | BEHAVIORAL: SOMNOLENCE (GENERAL DEPRESSED ACTIVITY) BEHAVIORAL: EXCITEMENT BEHAVIORAL: ATAXIA | Nippon Yakurigaku Zasshi. Japanese Journal of Pharmacology. Vol. 69, Pg. 523, 1973. |
rat | LD50 | subcutaneous | 149mg/kg (149mg/kg) | SENSE ORGANS AND SPECIAL SENSES: LACRIMATION: EYE BEHAVIORAL: TREMOR BEHAVIORAL: CONVULSIONS OR EFFECT ON SEIZURE THRESHOLD | Iyakuhin Kenkyu. Study of Medical Supplies. Vol. 6, Pg. 307, 1975. |
Safety Information of L-5-Hydroxytryptophan (CAS NO.4350-09-8):
Hazard Codes: XnXi
Risk Statements: 22-36/37/38-65-20/21/22-20/21
R22: Harmful if swallowed.
R36/37/38: Irritating to eyes, respiratory system and skin.
R65: Harmful: may cause lung damage if swallowed.
R20/21: Harmful by inhalation and in contact with skin.
R20/21/22: Harmful by inhalation, in contact with skin and if swallowed.
Safety Statements: 36-26
S36:Wear suitable protective clothing.
S26: In case of contact with eyes, rinse immediately with plenty of water and seek medical advice.
RIDADR: UN 2811 6.1/PG 3
WGK Germany: 3
RTECS: YN7110000
HazardClass: 6.1
PackingGroup: III
HS Code: 29339990
L-5-Hydroxytryptophan , its cas register number is 4350-09-8. It also can be called 5-Hydroxy-L-tryptophan ; Oxitriptan ; Tript-OH ; and L-Tryptophan, 5-hydroxy- . L-5-Hydroxytryptophan (CAS NO. 4350-09-8) is a naturally occurring amino acid, and is a precursor to the neurotransmitter serotonin and an intermediate in tryptophan metabolism. It is marketed in the United States and other countries as a dietary supplement for use as an antidepressant, appetite suppressant, and sleep aid. However, according to a 2001 meta-analysis, no sufficient high quality research has been done to establish its effectiveness for treatment of clinical depression or dysthymia.
About|Contact|Cas|Product Name|Molecular|Country|Encyclopedia
Message|New Cas|MSDS|Service|Advertisement|CAS DataBase|Article Data|Manufacturers | Chemical Catalog
©2008 LookChem.com,License: ICP
NO.:Zhejiang16009103
complaints:service@lookchem.com Desktop View