Dl-Phenylalanine
3-AMINO-3-PHENYLPROPANOIC ACID · DL-3-PHENYLALANINE · H-DL-PHE-OH · DL-PHENYALANINE · 3 AMINO-PHENYLPROPIONIC ACID · D,L-PHE · DLPA 375 · NSC 9959
Identifiers & Physical Properties
| CAS No. | 150-30-1 |
|---|---|
| Molecular formula | C9H11NO2 |
| Average molar mass | 165.19 g/mol |
| Monoisotopic mass | 165.07897859 g/mol |
| SMILES | NC(Cc1ccccc1)C(=O)O |
| InChIKey | COLNVLDHVKWLRT-UHFFFAOYSA-N |
| PubChem CID | 994 |
| ChEMBL | CHEMBL25080 |
| ChEBI | CHEBI:28044 |
| EC No. | 205-756-7 |
| DTXSID | DTXSID9023463 |
Chemical & Physical Properties
| XLogP | -1.5 |
|---|---|
| Topological polar surface area | 63.3 |
| Hydrogen bond donors | 2 |
| Hydrogen bond acceptors | 3 |
| Rotatable bonds | 3 |
| Heavy atoms | 12 |
| Formal charge | 0 |
| Complexity | 153 |
| Chemical classes | Biological Agents -> Amino Acids and Derivatives |
| Drugs | Pharmaceuticals |
| Food additives | FLAVOR ENHANCER, FLAVORING AGENT OR ADJUVANT -> FDA Substance added to food |
| Flavoring agents | EU Flavoring substances |
| Solubility | Soluble in water and dilute mineral acid and alkali hydroxide solutionsSlightly soluble (in ethanol)Water (Sparingly, Sonicated)14.11 g/L (25 ºC) |
| Vapor pressure | 0.00000005 [mmHg] |
| Physical Description | Solid[Merck Index] White powder[Sigma-Aldrich MSDS]White crystalline plateletsodourless |
| Melting point | 266-267 °C (dec.) (lit.) |
| Boiling point | 293.03°C (rough estimate) |
| Density | 1.1603 (rough estimate) |
| Refractive index | 1.5200 (estimate) |
| FEMA | 3726 | D,L-PHENYLALANINE |
| FLAVIS Number | 17.017 | D,L-Phenylalanine |
| Storage conditions | Store at RT. |
| Physical state | Powder |
| pKa (acidity coefficient) | pK1 2.58pK2 9.24(at 25℃) |
| Color | White |
| Odor | odorless |
| Odor type | odorless |
| Biological source | synthetic |
| Merck | 14,7271 |
| JECFA Number | 1432 |
| BRN | 1910407 |
| Stability | Stable. Incompatible with strong oxidizing agents. |
| Major applications | peptide synthesis |
| Cosmetics Ingredients Functions | FRAGRANCESKIN CONDITIONINGHAIR CONDITIONING |
| InChI | 1S/C9H11NO2/c10-8(9(11)12)6-7-4-2-1-3-5-7/h1-5,8H,6,10H2,(H,11,12) |
| InChIKey | COLNVLDHVKWLRT-UHFFFAOYSA-N |
| SMILES | NC(Cc1ccccc1)C(O)=O |
| LogP (partition coefficient) | 0.24 |
| CAS DataBase Reference | 150-30-1(CAS DataBase Reference) |
| Substances Added to Food (formerly EAFUS) | DL-PHENYLALANINE |
| FDA UNII | 8P946UF12S |
| NIST Chemistry Reference | L-Phenylalanine(150-30-1) |
| EPA Substance Registry System | Phenylalanine (150-30-1) |
| UNSPSC Code | 12352209 |
| NACRES | NA.22 |
| GHS pictogram | GHS07 |
| Signal word | Warning |
| GHS hazard statements | H315-H319 |
| GHS precautionary statements | P264-P280-P302+P352-P337+P313-P305+P351+P338-P362+P364-P332+P313 |
| Personal protective equipment (PPE) | Eyeshields, Gloves, type N95 (US) |
| Hazard symbols | Xi,C |
| Risk statements (R) | 36/37/38-34 |
| Safety statements (S) | 37/39-24/25-45-36/37/39-27-26 |
| Water hazard class (WGK) | 3 |
| Hazard Note | Irritant |
| TSCA inventory status | TSCA listed |
| Customs code | 29224995 |
| Storage class | 11 - Combustible Solids |
Safety & Regulations
| GHS classification | This chemical does not meet GHS hazard criteria for 99.1% (112 of 113) of all reports.Not ClassifiedAggregated GHS information provided per 113 reports by companies from 2 notifications to the ECHA C&L Inventory. |
|---|---|
| Regulatory information | Chemical: DL-PhenylalanineCommission Regulation (EC) No 1565/2000 (Repealed by Com. Implementing Reg. (EU) No 872/2012)Phenylalanine: Does not have an individual approval but may be used under an appropriate group standard |
| Other safety information | IMAP assessments - DL-Phenylalanine: Human health tier I assessment |
| Hazards summary | Safe when used as a flavoring agent in food[EFSA] Not considered hazardous by GHS classification[Sigma-Aldrich MSDS] See Phenylalanine. |
| Hazard Classes and Categories | Not Classified |
| Personal protective equipment (PPE) | Eyeshields, Gloves, type N95 (US) |
| Water hazard class (WGK) | 3 |
| TSCA inventory status | TSCA listed |
| Customs code | 29224995 |
| Risk statements (R) | 36/37/38-34 |
| Signal word | Warning |
| GHS pictogram | GHS07 |
| Hazard symbols | Xi,C |
| hazard_note | Irritant |
| Safety statements (S) | 37/39-24/25-45-36/37/39-27-26 |
| Storage class | 11 - Combustible Solids |
| GHS hazard statements | H315-H319 |
| GHS precautionary statements | P264-P280-P302+P352-P337+P313-P305+P351+P338-P362+P364-P332+P313 |
Applications & Uses
Description
As an essential amino acid, phenylalanine is necessary for the production of tyrosine in human body, which cannot be synthesized from more basic substances in humans and other animals, meaning that it is obtained only by ingestion of phenylalanine or phenylalanine- containing proteins, which is particularly rich in eggs, chicken, liver, beef, breast milk of mammals, and soybeans, etc. There are three forms of phenylalanine: L-phenylalanine, the natural form found in protein-rich foods, D-phenylalanine, the synthetic mirror image and DL-Phenylalanine (DLPA), the mixture of both forms made in the laboratory that can maximize benefits. DLPA is manufactured for medical, feed, and nutritional applications, which can be used to produce food and drink products. It is marketed as a nutritional supplement due to its reputed analgesic and antidepressant effects. Besides, it can be applied for depression, attention deficit-hyperactivity disorder (ADHD), Parkinson's disease, chronic pain, osteoarthritis, rheumatoid arthritis, alcohol withdrawal symptoms, and a skin disease called vitiligo.
Occurrence
Phenylalanine is the most commonly found aromatic amino acid in proteins and enzymes with a molar ratio of 3.5% compared to the other amino acids, about double the amount of any other aromatic amino acid. Reported found in white bread, macaroni, egg noodles, corn flakes, corn grits, oatmeal, wheat bran, wheat flakes, shredded wheat, barley, brown rice, rye flour, whole grain wheat flour, buttermilk, blue cheese, cheddar cheese, cottage cheese, cream cheese, parmesan cheese, bacon, cured ham, frankfurters, pork sausage, canned red kidney beans, canned sweet corn, canned peas, canned lima beans, canned potatoes, canned asparagus, canned snap beans, canned beets, beef, lamb, fresh ham, veal round, beef liver, chicken, chicken liver, turkey and other natural sources.
Uses
DL-Phenylalanine may be used in the synthesis of ternary piroxicam (Pir; 4-hydroxy-2-methyl-N-(2-pyridyl)-2H-1,2-benzothiazine-3-carboxamide 1,1-dioxide) complexes of Fe(II), Fe(III), Co(II), Ni(II), Cu(II) and Zn(II).
Uses
Component of the artificial sweetner aspartame, q.v.; nutrient.
Uses
DL-Phenylalanine is used torelieve cases of minor depressionand other mood issues as well as and physical discomforts and pain. It is also used in acupunctureanesthesia, alcohol withdrawal.
General Description
Phenylalanine is an amino acid. It participates in the preparation of ternary piroxicam complexes of Fe(II), Fe(III), Co(II), Ni(II), Cu(II) and Zn(II). Characterization of these complexes by elemental analyses, molar conductance, IR, UV-Vis, magnetic moment, diffuse reflectance and X-ray powder diffraction methods has been conducted. Crystalline DL-phenylalanine was prepared by its reduction in silica gel by solubility method.
Preparation & Synthesis
Preparation
By microbial bioengineered process.