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63-91-2 Usage

Occurrence

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

L-phenylalanine is an amino acid used as a skin-conditioning agent. It has greater use in hair care than in skin care products.

Preparation

From PTS-negative Escherichia coli bioengineered strains.

General Description

Odorless white crystalline powder. Slightly bitter taste. pH (1% aqueous solution) 5.4 to 6.

References

[1] http://www.umm.edu/health/medical/altmed/supplement/phenylalanine [2] Xueqin Song , Philip L. Lorenzi , Christopher P. Landowski , Balvinder S. Vig , John M. Hilfinger , Gordon L. Amidon (2005) Amino Acid Ester Prodrugs of the Anticancer Agent Gemcitabine:? Synthesis, Bioconversion, Metabolic Bioevasion, and hPEPT1-Mediated Transport, 2, 157-167.

Synthesis Reference(s)

Canadian Journal of Chemistry, 29, p. 427, 1951 DOI: 10.1139/v51-051The Journal of Organic Chemistry, 30, p. 3414, 1965 DOI: 10.1021/jo01021a035Tetrahedron Letters, 26, p. 2449, 1985 DOI: 10.1016/S0040-4039(00)94850-0

Safety Profile

Mildly toxic by intraperitoneal route. An experimental teratogen. Experimental reproductive effects. Human mutation data reported. When heated to decomposition it emits toxic fumes of NOx.

Description

Phenylalanie is an essential amino acid and it is the precursor of the amino acid tyrosine. The body cannot make phenylalanie but it needs phenylalanie to produce proteins. Thus, human needs to obtain phenylalanie from food. 3 forms of phenylalanie are found in the nature: D-phenylalanine, L-phenylalanine, and DL-phenylalanine. Among these three forms, L-phenylalanine is the natural form found in most foods that containing proteins, including beef, poultry, pork, fish, milk, yogurt, eggs, cheeses, soy products, and certain nuts and seeds. The form of phenylalanine determines its application. It is suggested that L-phenylalanine can strengthen the effect of UVA radiation for people with vitiligo, in which L-phenylalanine may lead to darkening or repigmentation of the white patches, particularly on the face. The neurotransmitters L-phenylalanine affects help reduce hunger, improve memory, lessen the symptoms of ADHD and Parkinson's disease, and ease chronic pain, according to the UMMC research. Thus, L-phenylalanine is used in the manufacture of food and drink products and sold as a nutritional supplement for its reputed analgesic and antidepressant effects. L-phenylalanine is also suggested as an intermediate for anti-cancer drugs. A few small studies showed promise using L-Phenylalanine to manage alcohol withdrawal and ease PMS symptoms. It is also used in artificial sweeteners such as aspartame.

Purification Methods

Likely impurities are leucine, valine, methionine and tyrosine. Crystallise L-phenylalanine from water by adding 4volumes of EtOH. Dry it in vacuo over P2O5. Also crystallise it from saturated refluxing aqueous solutions at neutral pH, or 1:1 (v/v) EtOH/water solution, or conc HCl. It sublimes at 176-184o/0.3mm with 98.7% recovery and unracemised [Gross & Gradsky J Am Chem Soc 77 1678 1955]. [Greenstein & Winitz The Chemistry of the Amino Acids J. Wiley, Vol 3 pp 2156-2175 1961, Beilstein 14 IV 1552.]

Chemical Properties

L-Phenylalanine has no odor and a slight bitter taste. It melts with decomposition at about 283°C. The pH of a 1 in 100 solution is between 5.4 and 6.0. FEMA notes this chemical is used in cocoa substitute only.

Health Hazard

ACUTE/CHRONIC HAZARDS: When heated to decomposition L-Phenylalanine emits toxic fumes of nitrogen oxides.

Uses

L-Phenylalanine is an essential amino acid. L-Phenylalanine is biologically converted into L-tyrosine, another one of the DNA-encoded amino acids, which in turn is converted to L-DOPA and further conv erted into dopamine, norepinephrine, and epinephrine. L-Phenylalanine is produced for medical, feed, and nutritional applications such as in the preparation of Aspartame.

Uses

phenylalanine is a conditioning agent with greater application in hair care than in skin care preparations. It is also used in suntan products.

Fire Hazard

Flash point data for L-Phenylalanine are not available; however, L-Phenylalanine is probably combustible.

Reactivity Profile

L-Phenylalanine may be light sensitive. Act as weak acids in solution.

Chemical Properties

White crystalline powder

Air & Water Reactions

Water soluble. Aqueous solutions are weak acids.

Definition

ChEBI: The L-enantiomer of phenylalanine.
InChI:InChI:1S/C9H11NO2/c10-8(9(11)12)6-7-4-2-1-3-5-7/h1-5,8H,6,10H2,(H,11,12)

63-91-2 Well-known Company Product Price

Brand (Code)Product description CAS number Packaging Price Detail
TCI America (P0134)  L-Phenylalanine  >98.0%(HPLC)(T) 63-91-2 25g 80.00CNY Detail
TCI America (P0134)  L-Phenylalanine  >98.0%(HPLC)(T) 63-91-2 250g 490.00CNY Detail
Alfa Aesar (A13238)  L-Phenylalanine, 99%    63-91-2 25g 189.0CNY Detail
Alfa Aesar (A13238)  L-Phenylalanine, 99%    63-91-2 50g 296.0CNY Detail
Alfa Aesar (A13238)  L-Phenylalanine, 99%    63-91-2 100g 536.0CNY Detail
Alfa Aesar (A13238)  L-Phenylalanine, 99%    63-91-2 500g 2145.0CNY Detail
Alfa Aesar (A13238)  L-Phenylalanine, 99%    63-91-2 1000g 3736.0CNY Detail
Sigma-Aldrich (40541)  L-Phenylalanine  certified reference material, TraceCERT® 63-91-2 40541-100MG 1,117.35CNY Detail
Sigma-Aldrich (PHR1100)  L-Phenylalanine  pharmaceutical secondary standard; traceable to USP and PhEur 63-91-2 PHR1100-1G 732.19CNY Detail
Sigma-Aldrich (91331)  L-Phenylalanine  analytical standard, for Nitrogen Determination According to Kjeldahl Method 63-91-2 91331-25G 644.67CNY Detail
Sigma-Aldrich (P1150000)  Phenylalanine  European Pharmacopoeia (EP) Reference Standard 63-91-2 P1150000 1,880.19CNY Detail
Sigma-Aldrich (P2126)  L-Phenylalanine  reagent grade, ≥98% 63-91-2 P2126-100G 916.11CNY Detail

63-91-2SDS

SAFETY DATA SHEETS

According to Globally Harmonized System of Classification and Labelling of Chemicals (GHS) - Sixth revised edition

Version: 1.0

Creation Date: Aug 12, 2017

Revision Date: Aug 12, 2017

1.Identification

1.1 GHS Product identifier

Product name L-phenylalanine

1.2 Other means of identification

Product number -
Other names Benzenepropanethioic acid,S-phenyl ester

1.3 Recommended use of the chemical and restrictions on use

Identified uses For industry use only. Food additives -> Flavoring Agents
Uses advised against no data available

1.4 Supplier's details

1.5 Emergency phone number

Emergency phone number -
Service hours Monday to Friday, 9am-5pm (Standard time zone: UTC/GMT +8 hours).

More Details:63-91-2 SDS

63-91-2Synthetic route

methyl (2S)-2-amino-3-phenylpropanoate
2577-90-4

methyl (2S)-2-amino-3-phenylpropanoate

L-phenylalanine
63-91-2

L-phenylalanine

Conditions
ConditionsYield
With ammonium bicarbonate; water In dichloromethane for 48h; α-chymotrypsin;100%
With sodium hydroxide In water; ethyl acetate pH=9 - 10;93%
at 25℃; for 0.833333h; enzyme alcalase from Bacillus licheniforms; pH 8.2;
N-Cbz-L-Phe
1161-13-3

N-Cbz-L-Phe

L-phenylalanine
63-91-2

L-phenylalanine

Conditions
ConditionsYield
With cell extract of Sphingomonas paucimobilis SC 16113 In water at 42℃; for 20h; Enzymatic reaction;100%
With hydrogen In ethanol for 0.5h;100%
With palladium on activated charcoal In methanol; ethyl acetate99%
H-Phe-OEt
3081-24-1

H-Phe-OEt

L-phenylalanine
63-91-2

L-phenylalanine

Conditions
ConditionsYield
With ammonium bicarbonate; water In dichloromethane for 36h; α-chymotrypsin;100%
With Tris buffer; water at 50℃; Rate constant;
With human valacyclovirase; water at 37℃; pH=7.4; Kinetics; Time; HEPES buffer; Enzymatic reaction;
((prop-2-yn-1-yloxy)carbonyl)-L-phenylalanine
439912-45-5

((prop-2-yn-1-yloxy)carbonyl)-L-phenylalanine

L-phenylalanine
63-91-2

L-phenylalanine

Conditions
ConditionsYield
With resin bound tetrathiomolybdate In methanol at 28℃; for 1.5h; ultrasonic bath;100%
2-oxo-3-(phenyl)propionic acid
156-06-9

2-oxo-3-(phenyl)propionic acid

L-phenylalanine
63-91-2

L-phenylalanine

Conditions
ConditionsYield
With formate dehydrogenase; NAD; ammonium formate at 30℃; for 24h; PheDH;99%
With A-(modified B6)-B-<ω-amino(ethylamino)>-β-cyclodextrin In water at 30℃; for 5h; pH 8.0 (phosphate buffer); Yield given;
With formate dehydrogenase; NAD; ammonium formate at 30℃; for 24h; Mechanism; buffer (pH 8.5); other oxo-acids; PheDH;
phenylalanine amide hydrochloride
108321-83-1

phenylalanine amide hydrochloride

L-phenylalanine
63-91-2

L-phenylalanine

Conditions
ConditionsYield
With pyridoxal 5'-phosphate monohydrate; cobalt(II) chloride In aq. buffer at 40℃; for 4h; pH=7.0; Enzymatic reaction;99%
(S)-2-acetylamino-3-phenylpropanoic acid
2018-61-3

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

L-phenylalanine
63-91-2

L-phenylalanine

Conditions
ConditionsYield
With pepsin immobilized on terephthalaldehyde functionalized chitosan magnetic nanoparticle In acetonitrile at 20℃; for 48h; pH=2;98%
With hydrogenchloride
With hydrogen bromide
phenylpyruvate-
620-76-8

phenylpyruvate-

L-phenylalanine
63-91-2

L-phenylalanine

Conditions
ConditionsYield
With ammonium formate; tris hydrochloride; nicotinamide adenine dinucleotide; formate dehydrogenase; phenylalanine dehydrogenase In water at 30℃; for 24h;98%
With ammonium formate; tris hydrochloride; nicotinamide adenine dinucleotide; phenylalanine and formate dehydrogenase In water at 30℃; for 24h; Equilibrium constant; pH = 8.5;98%
With L-glutamic acid; pyridoxal 5'-phosphate In water at 40℃; for 12h; E.coli Aspartate transaminase, pH 8;84%
With L-glutamic acid; E.coli Aspartate transaminase; pyridoxal 5'-phosphate at 40℃; for 12h; enzyme kinetics; pH 8; Miachaelis constant (Km); maximum velocity constant (vmax); further α-keto acids;84%
With L-glutamine; human glutamine transaminase K at 37℃; pH=7.4; aq. phosphate buffer; Enzymatic reaction;
((S)-1-Cyano-2-phenyl-ethyl)-carbamic acid methyl ester
631921-67-0

((S)-1-Cyano-2-phenyl-ethyl)-carbamic acid methyl ester

L-phenylalanine
63-91-2

L-phenylalanine

Conditions
ConditionsYield
With hydrogenchloride In water for 7h; Heating;98%
(S)-2-hydrazinyl-3-phenylpropanoic acid
1202-31-9

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

L-phenylalanine
63-91-2

L-phenylalanine

Conditions
ConditionsYield
With hydrogen; nickel In water; acetic acid under 25857.4 Torr;97%
(S)-2-{1-[4-Nitro-1,3-dioxo-indan-(2E)-ylidene]-ethylamino}-3-phenyl-propionic acid

(S)-2-{1-[4-Nitro-1,3-dioxo-indan-(2E)-ylidene]-ethylamino}-3-phenyl-propionic acid

A

L-phenylalanine
63-91-2

L-phenylalanine

B

2-[1-Hydrazino-eth-(E)-ylidene]-4-nitro-indan-1,3-dione

2-[1-Hydrazino-eth-(E)-ylidene]-4-nitro-indan-1,3-dione

Conditions
ConditionsYield
With hydrazine hydrate In ethanol for 3h; Ambient temperature;A n/a
B 97%
Phenylalanine
150-30-1

Phenylalanine

L-phenylalanine
63-91-2

L-phenylalanine

Conditions
ConditionsYield
With D-amino acid oxidase; E. coli branched-chain amino acid aminotransferase In water at 37℃; for 72h; Tris buffer, pH 8.5, 1mM EDTA, monosodium glutamate, bovine serum albumin, catalase, pyridoxal 5'-phosphate;96%
With porcine kidney D-amino acid oxidase (EC 1.4.3.3.); sodium cyanoborohydride; flavin adenine dinucleotide In phosphate buffer at 37℃;82%
With sodium hydroxide; oxygen at 30℃; for 24h; pH=7.3; aq. buffer; Enzymatic reaction; optical yield given as %ee; enantioselective reaction;44%
N-allyloxycarbonyl-(S)-phenylalanate
90508-20-6

N-allyloxycarbonyl-(S)-phenylalanate

L-phenylalanine
63-91-2

L-phenylalanine

Conditions
ConditionsYield
With tri-n-butyl-tin hydride; bis-triphenylphosphine-palladium(II) chloride In dichloromethane Ambient temperature;95%
N-tert-butoxycarbonyl-L-phenylalanine
13734-34-4

N-tert-butoxycarbonyl-L-phenylalanine

L-phenylalanine
63-91-2

L-phenylalanine

Conditions
ConditionsYield
With tetradecyl(trihexyl)phosphonium bistriflamide; trifluoroacetic acid at 130℃; for 0.166667h; Ionic liquid;95%
With methanol; tetrachloromethane at 20℃; for 12h; UV-irradiation;91%
With trifluoroacetic acid
With ethylenediaminetetraacetic acid; phenylmethylsulphonyl fluoride; water In aq. phosphate buffer at 30℃; Kinetics; Reagent/catalyst; Microbiological reaction; Enzymatic reaction;
With trifluoroacetic acid at 20℃; for 0.25h;
benzyl bromide
100-39-0

benzyl bromide

L-phenylalanine
63-91-2

L-phenylalanine

Conditions
ConditionsYield
95%
Multi-step reaction with 2 steps
1: 1.) LDA / 1.) THF, hexane, from -78 deg C to -20 deg C; 2.) THF, from -78 deg C to -20 deg C, 24 h
2: 92 percent / 1 N aq. HCl / 4 h / Heating
View Scheme
Multi-step reaction with 3 steps
1: 1.) sodium bis(trimethylsilyl)amide / 1.) THF, -82 deg C, 40 min, 2.) THF, -82 deg C, 1.5 h
2: 80 percent / trifluoroacetic acid / CH2Cl2 / 4 h
3: 76 percent / H2 / PdCl2 / tetrahydrofuran; ethanol / 29 h / 2172.02 Torr
View Scheme
Multi-step reaction with 2 steps
1: 1.) LDA / 1.) THF, -78 deg C, 2.) THF, -78 deg C
2: 85 percent / 6N HCl / 6 h / Heating
View Scheme
Multi-step reaction with 2 steps
1: 77 percent / NaN(Si(CH3)3)2 / tetrahydrofuran / 0.67 h / -100 °C
2: 1) TFA; 2) H2 / 2) Pd / 1) CH2Cl2
View Scheme
N-Fmoc L-Phe
35661-40-6

N-Fmoc L-Phe

L-phenylalanine
63-91-2

L-phenylalanine

Conditions
ConditionsYield
With sodium azide In N,N-dimethyl-formamide at 50℃; for 1h; Temperature; Time; Solvent;95%
Stage #1: N-Fmoc L-Phe With N-ethyl-N,N-diisopropylamine In dichloromethane for 1h; 2-chlorotrityl chloride resin;
Stage #2: With piperidine In N,N-dimethyl-formamide for 0.166667h; 2-chlorotrityl chloride resin;
Stage #3: With trifluoroacetic acid In dichloromethane for 0.166667h;
With piperidine In N,N-dimethyl-formamide for 0.0333333h; Solvent;
C34H29Cl2N3NiO3

C34H29Cl2N3NiO3

A

L-phenylalanine
63-91-2

L-phenylalanine

B

(S)-1-benzyl-N-[4-chloro-2-(2-chlorobenzoyl)phenyl]pyrrolidine-2-carboxamide
1616841-99-6

(S)-1-benzyl-N-[4-chloro-2-(2-chlorobenzoyl)phenyl]pyrrolidine-2-carboxamide

Conditions
ConditionsYield
Stage #1: C34H29Cl2N3NiO3 With hydrogenchloride In 1,4-dioxane; methanol; water at 60℃;
Stage #2: In 1,4-dioxane; methanol; water enantioselective reaction;
A 72%
B 95%
butan-1-ol
71-36-3

butan-1-ol

L-phenylalanine
63-91-2

L-phenylalanine

Conditions
ConditionsYield
94%
(3S,6S,8S,8aS)-3-benzyl-7,7,8a-trimethyl-3,5,6,7,8,8a-hexahydro-2H-6,8-methanobenzo[b][1,4]oxazin-2-one
141895-40-1

(3S,6S,8S,8aS)-3-benzyl-7,7,8a-trimethyl-3,5,6,7,8,8a-hexahydro-2H-6,8-methanobenzo[b][1,4]oxazin-2-one

L-phenylalanine
63-91-2

L-phenylalanine

Conditions
ConditionsYield
With hydrogenchloride In tetrahydrofuran at 70℃; for 3h;93%
(S)-4'-benzyl-9λ4-boraspiro[bicyclo[3.3.1]nonane-9,2'-[1,3,2]oxazaborolidin]-5'-one

(S)-4'-benzyl-9λ4-boraspiro[bicyclo[3.3.1]nonane-9,2'-[1,3,2]oxazaborolidin]-5'-one

L-phenylalanine
63-91-2

L-phenylalanine

Conditions
ConditionsYield
With tetrabutyl ammonium fluoride In tetrahydrofuran; water at 20℃; for 1h; Reagent/catalyst; Temperature; Solvent;93%
With peracetic acid; disodium hydrogenphosphate In dichloromethane at 20℃; Reagent/catalyst;
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