DL-Phenylalanine

Base Information

• Chemical Name: DL-Phenylalanine
• CAS No.: 63-91-2
• Molecular Formula: C9H11NO2
• Molecular Weight: 165.192
• Hs Code.: 2922.49
• 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: 63-91-2.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
• Vapor Pressure: 7.09E-05mmHg at 25°C
• Melting Point: 270-275 °C (dec.)(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.: H2O: 0.1 M at 20 °C, clear, colorless
• Water Solubility.: 1-5 g/100 mL at 25 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:

99.1% ^*data from raw suppliers

L-Phenylalanine ^*data from reagent suppliers

Safty Information:

• Pictogram(s): C
• Hazard Codes: C
• Statements: 36/37/38-34
• Safety Statements: 22-24/25-37/39-45-36/37/39-27-26

MSDS Files:

SDS file from LookChem

Useful:

• Chemical Classes: Biological Agents -> Amino Acids and Derivatives
• Canonical SMILES: C1=CC=C(C=C1)CC(C(=O)O)N
• Precursor of Biochemical Pathways: Phenylalanine serves as a precursor for the phenylpropanoid pathway and is essential for the synthesis of melanin, dopamine, noradrenaline (norepinephrine), and thyroxine.
• Marker of Disease Severity in COVID-19: Serum levels of phenylalanine have been associated with increased inflammation, higher SOFA scores, ICU admission, and mortality rates among COVID-19 patients. Lower serum phenylalanine levels were observed in mild cases compared to moderate and severe cases.
• Role in Age-Related Cardiac Dysfunction: Elevated plasma levels of phenylalanine are associated with age-related cardiac dysfunction. Aging leads to increased plasma phenylalanine levels, which may promote cardiac dysfunction. Pharmacological restoration of phenylalanine catabolism has been suggested as a potential therapeutic strategy for age-associated cardiac impairment.
• Personal Health Monitoring During Exercise: Phenylalanine fluctuations induced by protein intake during exercise can be tracked, and sweat-blood phenylalanine levels can be analyzed for personal health monitoring. Sweat phenylalanine levels correlate with blood phenylalanine levels and can be used to assess various nutrition and disease statuses, such as phenylketonuria (PKU), muscle protein metabolism during exercise, liver dysfunction in obesity, and viral infection severity.
• Associated with Phenylketonuria (PKU): Phenylalanine metabolism is disrupted in individuals with phenylketonuria (PKU), leading to the accumulation of phenylalanine in the brain, which can cause profound and irreversible mental disability if left untreated.

Technology Process of DL-Phenylalanine

There total 606 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:

L-phenylalanine-p-nitroanilide (2360-97-6,14235-17-7,14235-18-8,97471-44-8) → L-phenylalanine (63-91-2,25191-15-5,658-69-5,67675-33-6) + 4-nitro-aniline (100-01-6,104810-17-5)

Guidance literature:

With phosphate buffer; chymotrypsine; at 25 ℃; Product distribution; Rate constant; hydrolysis, various substrates under different reaction conditions;

DOI:10.1007/BF00699954

Reference yield:

p-Nitrophenyl-L-phenylalaninate (17663-35-3,55895-89-1,58848-63-8) → 4-nitro-phenol (100-02-7,78813-13-5,89830-32-0) + L-phenylalanine (63-91-2,25191-15-5,658-69-5,67675-33-6)

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:

Z-DL-Phe-OH (3588-57-6) → L-phenylalanine (63-91-2,25191-15-5,658-69-5,67675-33-6) + Cbz-D-Phe (2448-45-5)

Guidance literature:

With cell extract of Sphingomonas paucimobilis SC 16113; In water; at 42 ℃; for 20h; Enzymatic reaction;

DOI:10.1002/adsc.200303038

upstream raw materials:

N-formyl-phenylalanine

(S)-2-acetylamino-3-phenylpropanoic acid

(S)-N-benzoyl-phenylalanine anilide

N-chloroacetyl-DL-phenylalanine

Downstream raw materials:

(S)-2-(1,1-dioxo-1λ⁶-thiomorpholino)-3-phenyl-propionic acid

(S)-2-(nicotinamido)-3-phenylpropanoic acid

H-Phe-OEt

N-(N-trifluoroacetyl-glycyl)-L-phenylalanine

Refernces

• 1、 Gu, Zhenghua,Guo, Zitao,Shao, Jun,Shen, Chen,Shi, Yi,Tang, Mengwei,Xin, Yu,Zhang, Liang. "Recreating the natural evolutionary trend in key microdomains provides an effective strategy for engineering of a thermomicrobial N-demethylase". . . Retrieved 2022/03/09.
• 2、 Xiao, Wenjie,Chen, Shuhuan,Liu, Xiong,Ma, Yu. "Investigation of Taniaphos as a chiral selector in chiral extraction of amino acid enantiomers". . p. 292 - 302. Retrieved 2021/03/29.