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

• ChemBase编号: 7
• 分子式: C9H11NO2
• 平均质量: 165.18914
• 单一同位素质量: 165.0789786
• SMILES: OC(=O)[C@@H](N)Cc1ccccc1
• Canonical SMILES: N[C@H](C(=O)O)Cc1ccccc1
• 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)/t8-/m0/s1
• InChIKey: COLNVLDHVKWLRT-QMMMGPOBSA-N

名称和登记号

名称

• IUPAC标准名: (2S)-2-amino-3-phenylpropanoic acid
• IUPAC传统名: L-phenylalanine
• 别名: (S)-2-氨基-3-苯丙酸; L-苯基丙氨酸; (2S)-2-Amino-3-phenylpropanoic Acid; (S)-(-)-Phenylalanine; (S)-α-Amino-β-phenylpropionic Acid; (S)-α-Aminohydrocinnamic Acid; (S)-α-Amino-benzenepropanoic Acid; L-2-Amino-3-phenylpropanoic acid; L-PHENYLALANINE, U.S.P.; 2-Amino-3-phenylpropanoic acid; Phenylalanine; (S)-2-Amino-3-phenylpropionic acid; L-Phenylalanine; (S)-alpha-Amino-beta-phenylpropionic acid; L-Phenylalanine; D-Phenylalanine; L-2-Amino-3-phenyl propionic acid; H-Phe-OH

登记号

• CAS号: 150-30-1; 63-91-2
• EC号: 200-568-1
• MDL号: MFCD00004270; MFCD00064227
• Beilstein号: 1910408
• 默克索引号: 147271
• PubChem SID: 24898971; 46505708; 24887247; 24901797; 24898274; 24898657; 160963470
• PubChem CID: 994; 6140
• CHEBI ID: 58095
• CHEMBL: 301523
• Chemspider ID: 5910
• DrugBank ID: DB00120
• FEMA编号: 3585
• KEGG ID: D00021
• 美国药典/FDA物质标识码: 8P946UF12S
• 维基百科标题: Phenylalanine
• 欧洲委员会编号: 10488
• Flavis Number: 17.018

理论计算性质

JChem

• Acid pKa: 2.4692297
• 质子受体: 3
• 质子供体: 2
• LogD (pH = 5.5): -1.1845678
• LogD (pH = 7.4): -1.1878599
• Log P: -1.1844385
• 摩尔折射率: 45.1163 cm^3
• 极化性: 17.887253 Å^3
• 极化表面积: 63.32 Å^2
• 可自由旋转的化学键: 3
• 里宾斯基五规则: true

ALOGPS 2.1

• Log P: -1.35
• LOG S: -1.6
• 溶解度: 4.14e+00 g/l

分子性质

理化性质

• 溶解度: 1 M HCl: soluble50 mg/mL; H2O: soluble0.1 M at 20 °C, clear, colorless; H2O: soluble0.1 M, clear, colorless; Slight (0.1-1%); Water
• 外观: powder; White to Off-White Solid
• 熔点: 227°C dec.; 243-245°C; 270-275 °C (dec.)(lit.); 270-275°C; 273°C; 279-285°C
• 比旋光度: [α]/D -34.0±0.5°, c = 2 in H2O; [α]20/D -34±0.5°, c = 2% in H2O; [α]20/D -34±1°, c = 2% in H2O; [α]25/D -32.7°, c = 2 in H2O; [α]25/D -33.5°, c = 2 in H2O; -34 (c=2 in water)
• 疏水性(logP): -1.4
• pKa: 1.83 (carboxyl), 9.13 (amino)
• pH值: 5.0-7.0 (25 °C, 0.1 M in H2O)

安全信息

• 保存条件: Room Temperature (15-30°C)
• 保存注意事项: IRRITANT; Irritant
• RTECS编号: AY7535000
• 德国WGK号: 1
• TSCA收录: false; 是
• NFPA704:
  

  1

  2

  0
• 个人保护装置: Eyeshields, Gloves, type N95 (US), type P1 (EN143) respirator filter
• Regulation Compliance: FCC; FDA 21 CFR (172.320)

药理学性质

• 相关基因信息: human ... CA1(759), CA14(23632), CA2(760), CA4(762), CA5A(763), CA7(766)

产品相关信息

• 纯度: >99%; ≥98%; ≥98.5%; ≥99.0%; ≥99.0% (NT); 95+%; 97%; 98%; 98.5-101.0%; 99%
• 级别: analytical standard; certified reference material; EP; JP; Kosher; NI; PharmaGrade; reagent grade; SAJ special grade; TraceCERT®; USP
• 光学纯度: ee: 98% (GLC)
• 适用性: meets EP, JP, USP testing specifications; suitable for cell culture; suitable for manufacturing use
• 燃烧残渣: ≤0.1% (as SO4)
• 杂质: ≤0.3% foreign amino acids; 8.5%±0.2% total nitrogen acc. to Kjeldahl; endotoxin, tested; insoluble matter, passes filter test
• 痕量阳离子: Al: ≤5 mg/kg; As: ≤0.1 mg/kg; Ba: ≤5 mg/kg; Bi: ≤5 mg/kg; Ca: ≤10 mg/kg; Cd: ≤5 mg/kg; Co: ≤5 mg/kg; Cr: ≤5 mg/kg; Cu: ≤5 mg/kg; Fe: ≤5 mg/kg; K: ≤50 mg/kg; Li: ≤5 mg/kg; Mg: ≤5 mg/kg; Mn: ≤5 mg/kg; Mo: ≤5 mg/kg; Na: ≤50 mg/kg; NH4+: ≤100 mg/kg; Ni: ≤5 mg/kg; Pb: ≤5 mg/kg; Sr: ≤5 mg/kg; Zn: ≤5 mg/kg
• 痕量阴离子: chloride (Cl-): ≤50 mg/kg; sulfate (SO42-): ≤100 mg/kg; sulfate (SO42-): ≤200 mg/kg
• 生物来源: from non-animal source
• 干燥失重: ≤0.1% loss on drying; ≤0.1% loss on drying, 110°C; ≤0.2% loss on drying, 110 °C
• 产品质量级别: GMP-COMPENDIA; PREMIUM
• 产品线: BioUltra
• abs.: absorption0.1M/274 nm, H2O cut-off
• 线性分子式: C6H5CH2CH(NH2)CO2H

详细说明

MP Biomedicals - 05220616

MP Biomedicals Rare Chemical collection

MP Biomedicals - 02199540

White powder.

MP Biomedicals - 02102623

Crystalline
Purity: >99%

MP Biomedicals - 02194723

Cell Culture Reagent
Purity: >99%

DrugBank - DB00120

• Drug Groups: approved; nutraceutical
• Description: An essential aromatic amino acid that is a precursor of melanin; dopamine; noradrenalin (norepinephrine), and thyroxine. [PubChem]
• Indication: L-phenylalanine may be helpful in some with depression. It may also be useful in the treatment of vitiligo. There is some evidence that L-phenylalanine may exacerbate tardive dyskinesia in some schizophrenic patients and in some who have used neuroleptic drugs.
• Pharmacology: Used by the brain to produce Norepinephrine, a chemical that transmits signals between nerve cells and the brain; keeps you awake and alert; reduces hunger pains; functions as an antidepressant and helps improve memory.
• Toxicity: L-phenylalanine will exacerbate symptoms of phenylketonuria if used by phenylketonurics. L-phenylalanine was reported to exacerbate tardive dyskinesia when used by some with schizophrenia.
• Affected Organisms: Humans and other mammals
• Biotransformation: Hepatic. L-phenylalanine that is not metabolized in the liver is distributed via the systemic circulation to the various tissues of the body, where it undergoes metabolic reactions similar to those that take place in the liver.
• Absorption: Absorbed from the small intestine by a sodium dependent active transport process.
• External Links: Wikipedia; PDRhealth

Sigma Aldrich - P5482

包装
10 mg in autosmp vl

Sigma Aldrich - 78019

Other Notes
Growth requirement of various microorganisms1.

Sigma Aldrich - P8740

包装
按照 cGMP 要求进行制造和包装

Sigma Aldrich - W358509

包装
1 kg in poly bottle
1 sample in glass bottle
5, 10 kg in fiber drum

Sigma Aldrich - P2126

包装
1 kg in poly bottle
100, 500 g in poly bottle

Sigma Aldrich - 40541

Analysis Note
此认证标准物质 (CRM) 是根据 ISO/IEC 17025 和 ISO Guide 34 生产和认证的。该标准物质可溯源到 NIST 标准参考物质。
General description
认证的含量经定量 NMR 确定，并且证书上标明不确定度和有效期。 证书下载：http://www.sigma-aldrich.com。
法律信息
TraceCERT 注册商标 Sigma-Aldrich Co. LLC

Toronto Research Chemicals - P319415

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 converted into dopamine, norepinephrine, and epinephrine. L

参考文献

• Hollunger, G. et al.: Acta Pharmacol. Toxicol., 34, 391 (1974)
• Bagchi, S.P. et al.: Biochem. Pharmacol., 26, 900 (1974)
• Other amino acids have been resolved by crystallization of their complexes with L-phenylalanine, and decomplexation with activated carbon: Chem. Lett., 113 (1984).
• Formation of the N,N-dibenzyl benzyl ester by reaction with benzyl bromide and base, followed by LAH reduction and Swern oxidation, lead to the N,N-dibenzyl (S)-ɑ-amino aldehyde, a useful chiral intermediate: Org. Synth., 76, 110 (1998).