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4350-09-8

Basic Information
CAS No.: 4350-09-8
Name: L-5-Hydroxytryptophan
Article Data: 16
Cas Database
Molecular Structure:
Molecular Structure of 4350-09-8 (L-5-Hydroxytryptophan)
Formula: C11H12N2O3
Molecular Weight: 220.228
Synonyms: Tryptophan,5-hydroxy-, L- (8CI);(S)-5-Hydroxytryptophan;5-Hydroxy-L-tryptophan;5-Hydroxyl-L-tryptophan;Cincofarm;L-5-HTP;Levothym;Levotinine;Oxitriptan;Oxyfan;Pretonine;Quietim;Serotonyl;Telesol;Tript-Oh;
EINECS: 224-411-1
Density: 1.484 g/cm3
Melting Point: 270 °C (dec.)(lit.)
Boiling Point: 520.6 °C at 760 mmHg
Flash Point: 268.7 °C
Solubility: slightly soluble in water
Appearance: white to pale grey powder
Hazard Symbols: HarmfulXn, IrritantXi
Risk Codes: 22-36/37/38-65-20/21/22-20/21
Safety: 36-26
Transport Information: UN 2811 6.1/PG 3
PSA: 99.34000
LogP: 1.52820
Synthetic route
1953-54-4

indol-5-ol

56-45-1

L-serin

4350-09-8

L-5-HTP

Conditions
ConditionsYield
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;
90830-06-1

DL-5-hydroxytryptophane amide

4350-09-8

L-5-HTP

Conditions
ConditionsYield
43%
43%
73-22-3

L-Tryptophan

A

25198-02-1

7-Hydroxy-L-tryptophan

B

25242-90-4

4-Hydroxy-L-tryptophan

C

13567-14-1

(S)-6-hydroxytryptophan

D

4350-09-8

L-5-HTP

Conditions
ConditionsYield
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%
3520-59-0

L-N-benzyloxycarbonyl-5-benzyloxytryptophan

4350-09-8

L-5-HTP

Conditions
ConditionsYield
With ethanol; palladium Hydrogenation;
3017-27-4

5-benzyloxy-Nα-benzyloxycarbonyl-DL-tryptophan

4350-09-8

L-5-HTP

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1: quinine
2: palladium; ethanol / Hydrogenation
View Scheme
73-22-3

L-Tryptophan

A

61-54-1

tryptamine

B

2922-83-0

L-kynurenine

C

hydroxyhexahydropyrrolo[2,3-b]indole-2-carboxylic acid

D

(S )-2-Amino-4-(2-formamidophenyl)-4-oxobutanoic acid

E

hydroxyoxoindolylalanine

F

236094-74-9

2-amino-3-(2-oxoindolin-3-yl)propanoic acid

G

4350-09-8

L-5-HTP

Conditions
ConditionsYield
With dihydrogen peroxide at 37℃; for 6h; pH=4.6; Darkness; aq. borate buffer;
73-22-3

L-Tryptophan

4350-09-8

L-5-HTP

Conditions
ConditionsYield
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;
67-56-1

methanol

4350-09-8

L-5-HTP

5-hydroxy-DL-tryptophan methyl ester hydrochloride

Conditions
ConditionsYield
With thionyl chloride at -5 - 20℃; for 16h;98%
With thionyl chloride at 0 - 20℃; Inert atmosphere;74%
4350-09-8

L-5-HTP

50-67-9

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

Conditions
ConditionsYield
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℃;
38050-71-4

9-methoxy-9-BBN

4350-09-8

L-5-HTP

C19H25BN2O3

Conditions
ConditionsYield
With pyridine97%
Downstream Products
119768-45-5
50-67-9
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    Synonyms: 5-hydroxy-l-tryptopha;pretonine;C5-HYDROXY-L-TRYPTOPHAN;H-5-HYDROXY-TRP-OH;H-TRP(5-OH)-OH;L-2-AMINO-3-(5-HYDROXYINDOLYL)PROPIONIC ACID;L-5-HYDROXYTRYPTOPHAN HYDRATE;L-5-HYDROXYTRYPTOPHAN CAS: 4350-09-8 MF: C11H12N2O3 MW: 220.22 EINECS

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Chemistry

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

Uses


 L-5-Hydroxytryptophan (CAS NO.4350-09-8) is used as an antidepressant, appetite suppressant, and sleep aid.

Toxicity Data With Reference

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 Profile

Safety Information of L-5-Hydroxytryptophan (CAS NO.4350-09-8):
Hazard Codes: XnIrritantXiIrritant
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

Specification

 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.