L-Tryptophan

Bezeichnung:L-Tryptophan

CAS-Nr73-22-3

Englisch Name:L-Tryptophan

CBNumberCB3750054

SummenformelC11H12N2O2

Molgewicht204.23

MOL-Datei73-22-3.mol

Synonyma

L-Tryptophan

L-Tryptophan physikalisch-chemischer Eigenschaften

Schmelzpunkt	289-290 °C (dec.)(lit.)
alpha	-31.1 º (c=1, H20)
Siedepunkt	342.72°C (rough estimate)
Dichte	1.34
Brechungsindex	-32 ° (C=1, H2O)
storage temp.	2-8°C
Löslichkeit	20% NH₃: 0.1 g/mL at 20 °C, clear, colorless
Aggregatzustand	powder
pka	2.46(at 25℃)
Farbe	White to yellow-white
PH	5.5-7.0 (10g/l, H2O, 20℃)
Geruch (Odor)	wh. cryst. or cryst. odorless powd., sl. bitter taste
Optische Aktivität	[α]20/D 31.5±1°, c = 1% in H2O
Wasserlöslichkeit	11.4 g/L (25 ºC)
Merck	14,9797
BRN	86197
Stabilität	Stable. Incompatible with strong acids, strong oxidizing agents.
InChIKey	QIVBCDIJIAJPQS-VIFPVBQESA-N
LogP	0.704 (est)
CAS Datenbank	73-22-3(CAS DataBase Reference)
NIST chemische Informationen	L-Tryptophan(73-22-3)
EPA chemische Informationen	L-Tryptophan (73-22-3)

Sicherheit

Kennzeichnung gefährlicher	Xi
R-Sätze:	33-40-62-41-37/38-36/37/38-22
S-Sätze:	24/25-36/37/39-36-26
WGK Germany	2
RTECS-Nr.	YN6130000
F	8
TSCA	Yes
HS Code	29339990
Giftige Stoffe Daten	73-22-3(Hazardous Substances Data)
Toxizität	LD508mmol / kg (rat, intraperitoneal injection). It is safe when used in food (FDA, §172.320, 2000).

Gefahreninformationscode (GHS)

Bildanzeige (GHS)
Alarmwort

Achtung
Gefahrenhinweise

H225：Flüssigkeit und Dampf leicht entzündbar.

H290：Kann gegenüber Metallen korrosiv sein.

H314：Verursacht schwere Verätzungen der Haut und schwere Augenschäden.
Sicherheit

P210：Von Hitze, heißen Oberflächen, Funken, offenen Flammen und anderen Zündquellenarten fernhalten. Nicht rauchen.

P233：Behälter dicht verschlossen halten.

P234：Nur im Originalbehälter aufbewahren.

P240：Behälter und zu befüllende Anlage erden.

P241：Explosionsgeschützte [elektrische/Lüftungs-/ Beleuchtungs-/...] Geräte verwenden.

P242：Nur funkenfreies Werkzeug verwenden.

P243：Maßnahmen gegen elektrostatische Entladungen treffen.

P264：Nach Gebrauch gründlich waschen.

P264：Nach Gebrauch gründlich waschen.

P280：Schutzhandschuhe/Schutzkleidung/Augenschutz tragen.

P301+P330+P331：BEI VERSCHLUCKEN: Mund ausspülen. KEIN Erbrechen herbeiführen.

P303+P361+P353：BEI BERÜHRUNG MIT DER HAUT (oder dem Haar): Alle kontaminierten Kleidungsstücke sofort ausziehen. Haut mit Wasser abwaschen oder duschen.

P363：Kontaminierte Kleidung vor erneutem Tragen waschen.

P370+P378：Bei Brand: zum Löschen verwenden.

P390：Verschüttete Mengen aufnehmen, um Materialschäden zu vermeiden.

P403+P235：An einem gut belüfteten Ort aufbewahren. Kühl halten.

P405：Unter Verschluss aufbewahren.

P406：In korrosionsbeständigem/… Behälter mit korrosionsbeständiger Auskleidung aufbewahren.

P501：Inhalt/Behälter ... (Entsorgungsvorschriften vom Hersteller anzugeben) zuführen.

L-Tryptophan Chemische Eigenschaften,Einsatz,Produktion Methoden

R-Sätze Betriebsanweisung:
R33:Gefahr kumulativer Wirkungen.
R40:Verdacht auf krebserzeugende Wirkung.
R62:Kann möglicherweise die Fortpflanzungsfähigkeit beeinträchtigen.
R41:Gefahr ernster Augenschäden.
R37/38:Reizt die Atmungsorgane und die Haut.
R36/37/38:Reizt die Augen, die Atmungsorgane und die Haut.
R22:Gesundheitsschädlich beim Verschlucken.
S-Sätze Betriebsanweisung:
S24/25:Berührung mit den Augen und der Haut vermeiden.
S36/37/39:Bei der Arbeit geeignete Schutzkleidung,Schutzhandschuhe und Schutzbrille/Gesichtsschutz tragen.
S36:DE: Bei der Arbeit geeignete Schutzkleidung tragen.
S26:Bei Berührung mit den Augen sofort gründlich mit Wasser abspülen und Arzt konsultieren.
Chemische Eigenschaften
White to off-white crystalline powder
Chemische Eigenschaften
Appearance: white crystalline powder. Odorless, slightly bitter taste;
Solubility: slightly soluble in water (1.14%, 25 ℃), insoluble in ethanol; soluble in dilute acid or dilute alkali. mp 289 ° C (decomposition).
Isoelectric point: 5.89. [α] D + 2.8 (5 mol / L HCl), [α] D + 6.2 (0.5 mol / L NaOH).
It can be colored upon long-term exposure to light. Its co-heating reaction with water will generate a small amount of indole while heating in the presence of sodium hydroxide and copper sulfate will produce a large amount of indole. It is stable upon heating together with acid in the dark, but is easily to be decomposed when heated together with other amino acids, carbohydrates and aldehydes. L-tryptophan will be completely decomposed when applying acid to break down the protein.
Verwenden
adrenergic agonist
Verwenden
L-tryptophan is an essential amino acid which is necessary for normal growth in infants and for nitrogen balance in adults. It acts as a natural dietary supplement and used as an antidepressant, anxiolytic and sleep aid. It is used as a precursor to niacin, indole alkaloids and serotonin. It acts as an important intrinsic fluorescent probe, which finds to estimate the nature of microenvironment of the tryptophan.
Verwenden
tryptophan is one of the 21 amino acids comprising a protein. Tryptophan is a component of the skin’s natural moisturizing factors.
Vorbereitung Methode
The most attractive production processes for tryptophan are based on microorganisms used as enzyme sources or as overproducers: Enzymatic production from various precursors; Fermentative production from precursors; Direct fermentative production from carbohydrates by auxotrophic and analogue resistant regulatory mutants. L-tryptophan is synthesized from indole, pyruvate, and ammonia by the enzyme tryptophanase or from indole and L-serine/D,L-serine by tryptophan synthase these process variants were not economic due to the high costs of the starting materials. The microbial conversion of biosynthetic intermediates such as indole or anthranilic acid to L-tryptophan has also been considered as alternative for production.
However, the manufacturer using genetically modified strains derived fromBacillus amyloliquefaciens IAM 1521 was forced to stop Ltryptophan production. L-Tryptophan produced by this process was stigmatized because of side products found in the product causing a new severe disease termed eosinophilia-myalgia syndrome (EMS). One of the problematic impurities, "Peak E", was identified as 1,10-ethylidene- bis-(L-tryptophan), a product formed by condensation of one molecule acetaldehyde with two molecules of tryptophan.
Definition
ChEBI: L-tryptophan is the L-enantiomer of tryptophan. It has a role as an antidepressant, a nutraceutical, a micronutrient, a plant metabolite, a human metabolite, a Saccharomyces cerevisiae metabolite, an Escherichia coli metabolite and a mouse metabolite. It is an erythrose 4-phosphate/phosphoenolpyruvate family amino acid, a proteinogenic amino acid, a tryptophan and a L-alpha-amino acid. It is a conjugate base of a L-tryptophanium. It is a conjugate acid of a L-tryptophanate. It is an enantiomer of a D-tryptophan. It is a tautomer of a L-tryptophan zwitterion.
Trademarks
Ardeytropin;Kalma;Optimax;Sedanoct.
Weltgesundheitsorganisation (WHO)
L-tryptophan, an essential aminoacid and precursor of serotonin, was introduced into medicine in 1963 for the treatment of depression and sleep disorders. Its effectiveness in these conditions has, however, never been convincingly demonstrated. It is also widely used in dietary supplements, parenteral nutrition preparations and dietary products for children with phenylketonuria. In 1989, reports from the USA showed an association between the consumption of L-tryptophan containing preparations and the development of eosiniphilia-myalgia syndrome (EMS), a condition characterized by intense eosinophilia, severe muscle and joint pain, swelling of the arms and legs, skin rashes and possible fever. Some of the reported cases have been fatal. Since it is not yet clear whether L-tryptophan itself or an unidentified contaminant is the cause of the EMS, many drug regulatory authorities have suspended the marketing authorization of products containing tryptophan pending further investigation, whereas others have withdrawn these products or restricted their use.
Synthesis Reference(s)
The Journal of Organic Chemistry, 49, p. 3711, 1984 DOI: 10.1021/jo00194a008
Allgemeine Beschreibung
White powder with a flat taste. An essential amino acid; occurs in isomeric forms.
Air & Water Reaktionen
Slightly soluble in water.
Reaktivität anzeigen
Amines are chemical bases. They neutralize acids to form salts plus water. These acid-base reactions are exothermic. The amount of heat that is evolved per mole of amine in a neutralization is largely independent of the strength of the amine as a base. Amines may be incompatible with isocyanates, halogenated organics, peroxides, phenols (acidic), epoxides, anhydrides, and acid halides. Flammable gaseous hydrogen is generated by amines in combination with strong reducing agents, such as hydrides.
Health Hazard
ACUTE/CHRONIC HAZARDS: When heated to decomposition L-Tryptophan emits toxic fumes.
Brandgefahr
Flash point data for L-Tryptophan are not available. L-Tryptophan is probably combustible.
Biochem/physiol Actions
Tryptophan (Trp) is one of the functional amino acids that are associated with growth, reproduction, maintenance and immunity. Increased Trp availability is necessary for the regulation of mood, cognition and behaviour. It is hypothesised that L-Trp might be useful in inducing sleep in healthy adults against the normal circadian rhythm. Trp uptake by the brain depends on the plasma ratio of Trp to all of the other LNAAs (large neutral amino acids). Higher the Trp:LNAAs ratio, greater is the Trp uptake.
Sicherheitsprofil
Moderately toxic by intraperitoneal route. Experimental teratogenic and reproductive effects. Human mutation data reported. Questionable carcinogen with experimental tumorigenic data. When heated to decomposition it emits toxic fumes of NOx.
läuterung methode
Crystallise L-tryptophan from H2O/EtOH, wash it with anhydrous diethyl ether and dry it at room temperature in a vacuum over P2O5. It sublimes at 220-230o/0.03mm with 99% recovery and unracemised [Gross & Gradsky J Am Chem Soc 77 1678 1955]. [Cox & King Org Synth Coll Vol II 612 1943, Greenstein & Winitz The Chemistry of the Amino Acids J. Wiley, Vol 3 pp 2316-2345 1961, Beilstein 22 IV 6765.]

L-Tryptophan Upstream-Materialien And Downstream Produkte

L-Tryptophan Anbieter Lieferant Produzent Hersteller Vertrieb Händler.

73-22-3, L-Tryptophan Verwandte Suche:

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