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L-(-)-페닐알라닌

L-(-)-페닐알라닌
L-(-)-페닐알라닌 구조식 이미지
카스 번호:
63-91-2
한글명:
L-(-)-페닐알라닌
동의어(한글):
(S)-알파-아미노벤젠프로피온산;(S)-페닐알라닌;3-페닐알라닌;L-(-)-페닐알라닌;L-페닐알라닌;베타-페닐알라닌;알라닌,페닐-,L-;알파-아미노히드로신남산;페닐알라닌;페닐-알파-알라닌;페닐알라닌ℓ
상품명:
L-Phenylalanine
동의어(영문):
F;PHE;L-PHE;H-PHE-OH;NSC 79477;FEMA 3585;H-L-PHE-OH;Phenylalanin;PHENYLALANINE;Phenylalamine
CBNumber:
CB2488691
분자식:
C9H11NO2
포뮬러 무게:
165.19
MOL 파일:
63-91-2.mol

L-(-)-페닐알라닌 속성

녹는점
270-275 °C (dec.)(lit.)
알파
-34.1 º (c=2, water, dry basis)
끓는 점
293.03°C (rough estimate)
밀도
1.29
증기압
<1 Pa (25 °C)
굴절률
-34 ° (C=2, H2O)
FEMA
3585 | L-PHENYLALANINE
저장 조건
Store at RT.
용해도
H2O: 0.1 M at 20 °C, clear, colorless
물리적 상태
powder
산도 계수 (pKa)
2.2(at 25℃)
색상
White to off-white
수소이온지수(pH)
5.0-7.0 (25℃, 0.1M in H2O)
optical activity
[α]25/D -34.2°, c = 2 in H2O (dried basis)
수용성
1-5 g/100 mL at 25 ºC
Merck
14,7271
JECFA Number
1428
BRN
1910408
안정성
Stable. Incompatible with strong oxidizing agents.
InChIKey
COLNVLDHVKWLRT-QMMMGPOBSA-N
CAS 데이터베이스
63-91-2(CAS DataBase Reference)
NIST
L-Phenylalanine(63-91-2)
EPA
L-Phenylalanine(63-91-2)

안전

위험품 표기 C
위험 카페고리 넘버 36/37/38-34
안전지침서 22-24/25-37/39-45-36/37/39-27-26
WGK 독일 3
RTECS 번호 AY7535000
F 고인화성물질 10
TSCA Yes
HS 번호 29224995
유해 물질 데이터 63-91-2(Hazardous Substances Data)

L-(-)-페닐알라닌 MSDS


L-Phenylalanine

L-(-)-페닐알라닌 C화학적 특성, 용도, 생산

화학적 성질

White crystalline powder

화학적 성질

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.

출처

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.

용도

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

용도

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.

용도

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

정의

ChEBI: The L-enantiomer of phenylalanine.

제조 방법

From PTS-negative Escherichia coli bioengineered strains.

일반 설명

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

공기와 물의 반응

Water soluble. Aqueous solutions are weak acids.

반응 프로필

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

건강위험

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

화재위험

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

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.

효소 저해제

This aromatic amino acid (FW = 165.19 g/mol; CAS 63-91-2; pK = 2.20 1 and pK2 = 9.31 at 25°C; decomposes at 283-284°C), named systematically as (S) -2-amino-3-phenylpropanoic acid and symbolized by Phe and F) is one of the twenty proteogenic amino acids. Phenylalanine is nutritionally essential in the diets of mammals.The L-stereoisomer has a specific rotation of –4.47° at 25°C of the D line for 1.0–2.0 g/100 mL in 5 M HCl (–34.5° in distilled water). It is soluble in water (2.96 g/100 mL at 25°C; 4.46 g/100 mL at 50°C; and 6.62 g/100 mL at 75°C). L-Phenylalanine is very slightly soluble in ethanol and methanol and insoluble in diethyl ether. The solubility of the racemic mixture in water is 1.411 g/100 mL at 25°C (3.708 g/100 mL at 75°C). This aromatic amino acid has both useful absorbance and fluorescent properties. It absorbs light in t–1he u–l1traviolet region of the spectrum (lmax = 257.5 nm with e = 195 Mcm in 0.1 M HCl). DL- Phenylalanine, which has a sweetish taste, is unstable in alkaline solutions. Approximately three-fourths of the amino acid will decompose in five hours at 110–115°C in a sealed ampule in 5 M NaOH. Role in Phenylketonuria: The autosomal recessive disorder Phenylketonuria (PKU) is caused by mutations in the phenylalanine hydroxylase (PAH) gene, leading to childhood mental retardation by exposing neurons to cytotoxic phenylalanine (Phe) levels. Although many of the effects of PKU- associated Phe accumulation are indirect (e.g., decreased creatine kinase activity, deficient myelin production, and reduced dopamine synthesis), high Phe concentrations also trigger apoptosis by activating the mitochondria-initiated intrinsic pathway through the RhoA/Rho-associated kinase pathway and through the Fas receptor (FasR) -mediated cell death receptor pathway. Target (s) : acetylcholinesterase, inhibited by DL- and L-phenylalanine; agaritine g-glutamyltransferase; alkaline phosphatase, also inhibited by DL-phenylalanine; D- amino-acid oxidase; 2-aminohexano-6-lactam racemase, weakly inhibited; aminopeptidase B, weakly inhibited; apyrase; arginase, weakly inhibited; arogenate dehydrogenase, or cyclohexadienyl dehydrogenase; arylformamidase, weakly inhibited ; asparagine:oxo-acid aminotransferase; aspartokinase III, weakly inhibited; benzoate 4-monooxygenase; carboxypeptidase A; carboxypeptidase C, or carboxypeptidase Y; catechol oxidase; chorismate mutase (16-22); cystathionine g-lyase, or cysteine desulfhydrase, mildly inhibited by racemic mixture; cystinyl aminopeptidase, or oxytocinase; cytosol alanyl aminopeptidase ; 3-deoxy-7-phosphoheptulonate synthase, or 3-deoxy-D-arabino- heptulosonate-7-phosphate synthetase; dimethylglycine N- methyltransferase, weakly inhibited; b-glucosidase; hemoglobin S polymerization; (S) -2-hydroxy-acid oxidase; 2- isopropylmalate synthase; kynurenine:oxoglutarate aminotransferase ; lactate 2-monooxygenase; membrane alanyl aminopeptidase, or aminopeptidase N (80-82); Na+/K+-exchanging ATPase ; ornithine (lysine) transaminase, weakly inhibited; pepsin, weakly inhibited; 4-phytase; polyphenol oxidase; prephenate dehydratase; prephenate dehydrogenase ; procollagen-lysine 5-dioxygenase, weakly inhibited; propionyl- CoA carboxylase; pyruvate kinase; sarcosine/ dimethylglycine N-methyltransferase, weakly inhibited; shikimate kinase; starch phosphorylase; thermolysin, Ki = 15.6 mM ; tryptophanase, or tryptophan indole-lyase; tryptophan 5-monooxygenase; tyrosinase, or monophenol monooxygenase; tyrosine 3-monooxygenase (46,47,132,134, 135); tyrosine phenol-lyase; and tyrosine-phosphatase; 3- deoxy-D-arabino-heptulosonate 7-phosphate synthase (DAH7PS), Neisseria meningitidis, allosteric.

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.]

L-(-)-페닐알라닌 준비 용품 및 원자재

원자재

준비 용품


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