DL-Phenylalanine

Base Information

• Chemical Name: DL-Phenylalanine
• CAS No.: 673-06-3
• Molecular Formula: C9H11NO2
• Molecular Weight: 165.192
• Hs Code.: 29224995
• European Community (EC) Number: 205-756-7
• NSC Number: 620354,79477,25005,9959
• UNII: 8P946UF12S
• DSSTox Substance ID: DTXSID9023463
• Nikkaji Number: J1.258K
• Wikidata: Q27103475
• NCI Thesaurus Code: C61713
• ChEMBL ID: CHEMBL25080
• Mol file: 673-06-3.mol

Synonyms:1,2-dilauroylphosphatidic acid;1,2-dilauroylphosphatidic acid, sodium salt;DLPA

Chemical Property of DL-Phenylalanine

Chemical Property:

• Appearance/Colour: white crystalline powder
• Melting Point: 273-276 °C(lit.)
• Refractive Index: 34 ° (C=2, H2O)
• Boiling Point: 307.5 °C at 760 mmHg
• PKA: 2.2(at 25℃)
• Flash Point: 139.8 °C
• PSA: 63.32000
• Density: 1.201 g/cm³
• LogP: 1.34130
• Storage Temp.: Store at RT.
• Solubility.: Methanol (Slightly), Water (Slightly)
• Water Solubility.: 27 g/L (20 ºC)
• XLogP3: -1.5
• Hydrogen Bond Donor Count: 2
• Hydrogen Bond Acceptor Count: 3
• Rotatable Bond Count: 3
• Exact Mass: 165.078978594
• Heavy Atom Count: 12
• Complexity: 153

Purity/Quality:

99% ^*data from raw suppliers

D-Phenylalanine ^*data from reagent suppliers

Safty Information:

• Pictogram(s): Xi
• Hazard Codes: Xi,C
• Statements: 34
• Safety Statements: 24/25-45-36/37/39-27-26

MSDS Files:

SDS file from LookChem

Total 1 MSDS from other Authors

Useful:

• Chemical Classes: Biological Agents -> Amino Acids and Derivatives
• Canonical SMILES: C1=CC=C(C=C1)CC(C(=O)O)N
• Description: D-phenylalanine is an inhibitor of enzymes that inactivate enkephalins. Enkephalins are naturally occurring morphine-like peptides that function to reduce pain. By blocking enzymes from degrading enkephalins, D-phenylalanine can reduce pain severity. Phenylalanine is the only amino acid other than methionine in which both isomers, L and D, are readily absorbed. DLPA is 50% D-phenylalanine and 50% L-phenylalanine, making it clinically useful as a neurotransmitter precursor and as a potential pain mediator.Phenylalanine is found in three different forms. The natural form, found in food, is also called L-phenylalanine. There’s also a synthetic form, D-phenylalanine, which is very similar to the natural version. Both of these forms come with their own unique benefits, but if you want to get the most out of them, you’ll want to look at the third form: DL-phenylalanine. This form combines both the “L” and “D” forms, creating a supplement with the benefits of both types. 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.
• Uses: 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.

Technology Process of DL-Phenylalanine

There total 227 articles about DL-Phenylalanine which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield:

D-phenylalanine p-nitrophenyl ester (58848-63-8) → 4-nitro-phenol (100-02-7,78813-13-5,89830-32-0) + D-(R)-phenylalanine (673-06-3,25191-15-5,658-69-5,67675-33-6)

Guidance literature:

With Enterobacter cloacae P99 β-lactamase; at 25 ℃; pH=7.5; Reagent/catalyst; Concentration; Kinetics; aq. buffer; Enzymatic reaction;

DOI:10.1021/bi101071r

Reference yield:

p-Nitrophenyl-D-phenylalaninate (17663-35-3,55895-89-1,58848-63-8) → 4-nitro-phenol (100-02-7,78813-13-5,89830-32-0) + D-β-Phenyl-α-alanine (673-06-3,25191-15-5,658-69-5,67675-33-6)

Guidance literature:

With Z-Phe-His-Leu; Tris-KCl buffer; water; cetyltrimethylammonim bromide; N,N-dimethyl-N-tetradecyltetradecan-1-aminium bromide; In acetonitrile; at 25 ℃; Rate constant; variation of ionic strength; enantioselectivity (L/D);

Reference yield:

ulleungamide A → L-threonine (72-19-5,134357-96-3,7013-32-3,82822-12-6) + (S)-2-isopropylsuccinic acid (1187-70-8) + D-(R)-phenylalanine (673-06-3,25191-15-5,658-69-5,67675-33-6) + 5-hydroxy-6-methyl-2,3-dehydropipecolic acid + N-methyl-D-phenylalanine (56564-52-4) + (2S,4R)-4-hydroxypiperidine-2-carboxylic acid (1844-40-2,175671-49-5,189385-64-6) + glycine (56-40-6,18875-39-3,25718-94-9) + pipecolinic acid (3105-95-1,83680-83-5)

Guidance literature:

With hydrogenchloride; at 100 ℃; for 1h;

DOI:10.1021/acs.orglett.5b01969

upstream raw materials:

(R)-N-acetylphenylalanin

Phenylalanine

N-Chloroacetyl-D-phenylalanine

DL-N-benzoylphenylalanine

Downstream raw materials:

N-bromoacetyl-D-phenylalanine

(R)-(-)-N,N-Dimethyl-phenylalanin-ethylester

N-decanoyl-D-phenylalanine

N-(cycloheptylcarbonyl)-D-phenylalnine