Basic information Description In vitro In vivo Biological Activity Benefits Side Effects Safety Supplier Related
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D-Phenylalanine

Basic information Description In vitro In vivo Biological Activity Benefits Side Effects Safety Supplier Related

D-Phenylalanine Basic information

Product Name:
D-Phenylalanine
Synonyms:
  • D-beta-Phenyl-alpha-aminopropionic acid
  • d-alpha-aminohydrocinnamic acid
  • D-ALPHA-AMINO-BETA-PHENYL-PROPIONIC ACID
  • D-2-AMINO-3-PHENYLPROPANOIC ACID
  • D(+)-PHENYLALANINE
  • D-PHENYLALANINE
  • d-phe
  • H-D-PHE-OH
CAS:
673-06-3
MF:
C9H11NO2
MW:
165.19
EINECS:
211-603-5
Product Categories:
  • Nateglinide intermediate
  • Inhibitors
  • amino acid
  • chemicals
  • organic acids
  • pharmaceutical intermediate
  • Amino ACIDS SERIES
  • Aromatic Propionic Acids
  • Phenylalanine [Phe, F]
  • Amino Acids and Derivatives
  • alpha-Amino Acids
  • Amino Acids
  • Biochemistry
  • phenlalnine
  • Benzene derivatives
  • Amino Acids
Mol File:
673-06-3.mol
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D-Phenylalanine Chemical Properties

Melting point:
273-276 °C(lit.)
alpha 
33.5 º (c=2, H2O)
Boiling point:
293.03°C (rough estimate)
Density 
1.1603 (rough estimate)
refractive index 
34 ° (C=2, H2O)
storage temp. 
Store at RT.
pka
2.2(at 25℃)
form 
Powder
color 
White to off-white
Water Solubility 
27 g/L (20 ºC)
Merck 
14,7271
BRN 
2804068
Stability:
Stable. Incompatible with strong oxidizing agents, acids, bases.
InChIKey
COLNVLDHVKWLRT-MRVPVSSYSA-N
CAS DataBase Reference
673-06-3(CAS DataBase Reference)
EPA Substance Registry System
D-Phenylalanine (673-06-3)
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Safety Information

Hazard Codes 
Xi,C
Risk Statements 
34
Safety Statements 
24/25-45-36/37/39-27-26
WGK Germany 
3
RTECS 
AY7533000
Hazard Note 
Irritant
TSCA 
Yes
HS Code 
29224995
Toxicity
TDLo orl-hmn: 500 mg/kg/5W-I:GIT JACTDZ 1(3),124,82

MSDS

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D-Phenylalanine Usage And Synthesis

Description

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. It can also be used as pharmaceutical intermediates that are mainly used to treat, prevent osteoporosis, cardiovascular, diabetes and arterioscleros.

In vitro

The binding of D-Phenylalanine to carboxypeptidase A confers anion sensitivity upon the function of the enzyme by breaking the hydrogen bond between the active site base, Glu-270, and the zinc-bound water molecule.

In vivo

D-Phenylalanine (500 mg/kg p.o.) produces a small increase in aversive threshold which is not statistically significant and not naloxone reversible. Acetylsalicylic acid (200 mg/kg p.o.) but not zomepirac sodium (200 mg/kg p.o.) in combination with D-phenylalanine (500 mg/kg) produces a small statistically significant increase in aversive threshold.

Biological Activity

DL-Phenylalanine (DLPA) is marketed as a nutritional supplement for its purported analgesic and antidepressant activities. DL-Phenylalanine is a mixture of D-phenylalanine and L-phenylalanine. The reputed analgesic activity of DL-phenylalanine may be explained by the possible blockage by D-phenylalanine of enkephalin degradation by the enzyme carboxypeptidase A. The mechanism of DL-phenylalanine's supposed antidepressant activity may be accounted for by the precursor role of L-phenylalanine in the synthesis of the neurotransmitters norepinephrine and dopamine. Elevated brain levels of norepinephrine and dopamine are thought to have an antidepressant effect. D-Phenylalanine is absorbed from the small intestine and transported to the liver via the portal circulation. A small amount of D-phenylalanine appears to be converted to L-phenylalanine. D-Phenylalanine is distributed to the various tissues of the body via the systemic circulation. It appears to cross the blood–brain barrier less efficiently than L-phenylalanine, and so a small amount of an ingested dose of D-phenylalanine is excreted in the urine without penetrating the central nervous system.

Benefits

Phenylalanine can be used to produce the molecule dopamine. Dopamine malfunction in the brain is associated with some forms of depression.
In addition to vitiligo and depression, phenylalanine has been studied for potential effects on:
Pain: The D-form of phenylalanine may contribute to pain relief in some instances, though study results are mixed.
Alcohol withdrawal: A small amount of research indicates that this amino acid, along with other amino acids, may help alleviate symptoms of alcohol withdrawal.
Parkinson’s disease: Very limited evidence suggests that phenylalanine may be beneficial in treating Parkinson’s disease, but more studies are needed.
ADHD: Currently, research does not indicate benefits of this amino acid for the treatment of attention deficit hyperactivity disorder (ADHD).

Side Effects

Phenylalanine is found in many protein-containing foods and is “generally recognized as safe” by the Food and Drug Administration (FDA). The amount of this amino acid found in foods should not pose a risk for otherwise healthy individuals. What’s more, few or no side effects are generally observed at supplement doses of 23–45 mg per pound (50–100 mg per kg) of body weight. However, it may be best for pregnant women to avoid taking phenylalanine supplements.

Description

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. It can also be used as pharmaceutical intermediates that are mainly used to treat, prevent osteoporosis, cardiovascular, diabetes and arterioscleros.

Chemical Properties

White crystalline powder

Uses

antidepressant

Definition

ChEBI: The D-enantiomer of phenylalanine.

General Description

Needles or prisms.

Air & Water Reactions

Water soluble. Aqueous solutions are weakly acidic.

Reactivity Profile

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.

Fire Hazard

Flash point data for D-alpha-Amino-beta-phenylpropionic acid are not available, however D-alpha-Amino-beta-phenylpropionic acid is probably combustible.

Safety Profile

Mildly toxic by intraperitoneal route. Human systemic effects by ingestion: nausea, hypermotility, diarrhea. When heated to decomposition it emits toxic fumes of NOx.

References

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.

D-Phenylalanine Preparation Products And Raw materials

Raw materials

D-PhenylalanineSupplier

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