D-Phenylalanin

Bezeichnung:D-Phenylalanin

CAS-Nr673-06-3

Englisch Name:D-Phenylalanine

CBNumberCB9773699

SummenformelC9H11NO2

Molgewicht165.19

MOL-Datei673-06-3.mol

Synonyma

D-Phenylalanin

D-Phenylalanin physikalisch-chemischer Eigenschaften

Schmelzpunkt	273-276 °C(lit.)
Siedepunkt	293.03°C (rough estimate)
alpha	33.5 º (c=2, H2O)
Dichte	1.1603 (rough estimate)
Brechungsindex	34 ° (C=2, H2O)
storage temp.	Store at RT.
Löslichkeit	Methanol (Slightly), Water (Slightly)
Aggregatzustand	Powder
pka	2.2(at 25℃)
Farbe	White to off-white
Wasserlöslichkeit	27 g/L (20 ºC)
Merck	14,7271
BRN	2804068
Stabilität	Stable. Incompatible with strong oxidizing agents, acids, bases.
InChIKey	COLNVLDHVKWLRT-MRVPVSSYSA-N
LogP	0.235 (est)
CAS Datenbank	673-06-3(CAS DataBase Reference)
EPA chemische Informationen	D-Phenylalanine (673-06-3)

Sicherheit

Kennzeichnung gefährlicher	Xi,C
R-Sätze:	34
S-Sätze:	24/25-45-36/37/39-27-26
WGK Germany	3
RTECS-Nr.	AY7533000
Hazard Note	Irritant
TSCA	Yes
HS Code	29224995
Toxizität	TDLo orl-hmn: 500 mg/kg/5W-I:GIT JACTDZ 1(3),124,82

Gefahreninformationscode (GHS)

D-Phenylalanine Chemische Eigenschaften,Einsatz,Produktion Methoden

R-Sätze Betriebsanweisung:
R34:Verursacht Verätzungen.
S-Sätze Betriebsanweisung:
S24/25:Berührung mit den Augen und der Haut vermeiden.
S45:Bei Unfall oder Unwohlsein sofort Arzt zuziehen (wenn möglich, dieses Etikett vorzeigen).
S36/37/39:Bei der Arbeit geeignete Schutzkleidung,Schutzhandschuhe und Schutzbrille/Gesichtsschutz tragen.
S27:Beschmutzte, getränkte Kleidung sofort ausziehen.
S26:Bei Berührung mit den Augen sofort gründlich mit Wasser abspülen und Arzt konsultieren.
Beschreibung
D-Phenylalanine, also known as D-alpha-Amino-beta-phenylpropionic acid, is a kind of non-proteinogenic amino acid. The biological function of D-phenylalanine remains unclear. However, it has certain anti-depressant, analgesic activities and pharmacological activity at niacin receptor II. The mechanism action of its analgesic activity seems to originate from its inhibition of enkephalin degradation by the carboxypeptidase A. Enkephalins are part of your body’s natural pain relief system. When they are broken down by enkephalinase, this contributes to the sensation of pain. D-Phenylalanine is specifically thought to be beneficial for reducing feelings of chronic pain. D-phenylalanine has been used with mixed results to treat chronic pain, including pain caused by rheumatoid arthritis. The primary use of D-phenylalanine as a health supplement is the relief of discomfort.
Chemische Eigenschaften
White crystalline powder
Verwenden
D-Phenylalanine, the stereoisomer of L-Phenylalanine (P319415) has been used in the synthesis of Schaeffer’s acid analogues as important structures in tuberculostatic design. They exhibit the ability to inhibit Mycobacterium tuberculosis type II dehydroquinase.
Definition
ChEBI: D-phenylalanine is the D-enantiomer of phenylalanine. It is a phenylalanine and a D-alpha-amino acid. It is a conjugate base of a D-phenylalaninium. It is a conjugate acid of a D-phenylalaninate. It is an enantiomer of a L-phenylalanine. It is a tautomer of a D-phenylalanine zwitterion.
Allgemeine Beschreibung
D-phenylalanine appears as needles or prisms.
Air & Water Reaktionen
Water soluble. Aqueous solutions are weakly acidic.
Reaktivität anzeigen
D-alpha-Amino-beta-phenylpropionic acid may be light sensitive. D-alpha-Amino-beta-phenylpropionic acid reacts with strong oxidizing agents, acids and bases. . Act as weak acids in solution.
Brandgefahr
Flash point data for D-alpha-Amino-beta-phenylpropionic acid are not available, however D-alpha-Amino-beta-phenylpropionic acid is probably combustible.
Pharmakokinetik
D-Phenylalanine is the synthetic dextro isomer of phenylalanine, an essential amino acid with anti-depressant and analgesic activities. D-Phenylalanine is converted into tyrosine and tyrosine in turn is converted into L-dopa, norepinephrine, and epinephrine, three key neurotransmitters. As a result this agent is associated with elevated levels of the neurotransmitters dopamine and norepinephrine in the brain, which may alleviate symptoms of depression. In addition, as an inhibitor of enkephalinase, which metabolizes endorphins, D-phenylalanine may be used to treat chronic pain through blocking the break down of endorphins (natural pain killers).
Sicherheitsprofil
Mildly toxic by intraperitoneal route. Human systemic effects by ingestion: nausea, hypermotility, diarrhea. When heated to decomposition it emits toxic fumes of NOx.
Einzelnachweise
https://www.alfa.com/en/catalog/A10572/
https://en.wikipedia.org/wiki/Phenylalanine
Christianson, D. W., et al. "Binding of D-phenylalanine and D-tyrosine to carboxypeptidase A. " Journal of Biological Chemistry264.22(1989):12849-53.

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