Phenylalanine L-苯丙氨酸

CAS 63-91-2 MFCD00064227

化学结构图

63-91-2
SMILES: N[C@@H](Cc1ccccc1)C(=O)O

化学属性

Mol. FormulaC9H11NO2
Mol. Weight165.19
Density1.29
Melting Point270-275°C
TSCAYes
Solubility14.11 G/L (25 ºC)
Stability对光敏感
Appearance 必需氨基酸之一。其生理作用与酪氨酸有关。可影响甲状腺激素和毛发、皮肤的黑色素。D-型与L-型的生理效果相同。最低需要量(mg/kg?d):成人男子31;幼儿169。 无色至白色片状晶体或白色结晶性粉末。略有特殊气味和苦味。约于283℃熔化并分解。10%水溶液的pH值为5.4~6.0。在受热、光照、空气中稳定。与葡萄糖一起加热则着色。碱性下不稳定。溶于水(3g/100ml,25℃)。难溶于乙醇、稀无机酸和碱性溶液。 powder
Refractive index-34 ° (C=2, H2O)
Boiling Point307.5°C at 760 mmHg

别名和识别编码

Chemical NameL-Phenylalanine
CAS Number63-91-2
Alfabeta NamePHENYLALANINE L-
MDL NumberMFCD00064227
Synonym L-Phenylalanine {LY} L-Phenylalanine {} {LY} L-Phenylalanine {} {} {LY} L-Phenylalanine {} {} {} {LY} L-Phenylalanine {} {} {} {} {LY} L-Phenylalanine {} {} {} {} {} {LY} L-Phenylalanine {} {} {} {} {} {} {LY} L-Phenylalanine {} {} {} {} {} {} {} {LY} L-Phenylalanine {} {} {} {} {} {} {} {} {LY} L-Phenylalanine {} {} {} {} {} {} {} {} {} {LY} L-Phenylalanine {} {} {} {} {} {} {} {} {} {} {LY} L-Phenylalanine {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {LY} L-Phenylalanine {} {} {} {} {} {} {} {} {} {} {} {} {LY} L-Phenylalanine {} {} {} {} {} {} {} {} {} {} {} {} {} {LY} L-Phenylalanine {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} { {} {} {} {} {} {} {} {} {} {} {} {} {} {} {LY} L-Phenylalanine {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {LY} L-Phenylalanine {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {LY} L-Phenylalanine {} {} {} {} {} {} {} {} {}
EC Number200-568-1
Beilstein Registry Number1910408
PubChem Substance ID6140
Merck Number7271
Chemical Name TranslationL-苯丙氨酸
Reaxys-RN1910408
Wiswesser Line NotationQVYZ1R -L
LabNetwork Molecule IDLN00173955
InChIInChI=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
Canonical SMILESN[C@@H](CC1=CC=CC=C1)C(O)=O
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分类

  • {SNA} Amino Acids, Amino acids, Biochemicals and Reagents, Functional Foods, Nutrition Research, Pharmacopoeia, Pharmacopoeia A-Z, Pharmacopoeial Amino Acids
  • {SNA} Allium cepa (Onion), Allium sativum (Garlic), Aloe Vera, Amino Acid Library, Amino Acids, Amino Acids & Derivatives, Amino Acids & Vitamins, Amino Acids and Vitamins, Amino acids, Chemical Biology, Chemical Synthesis, Cichorium intybus (Chicory), Core Bioreagents, Functional Foods, Ginkgo biloba, Humulus lupulus (Hops), Life Science Reagents for Cell
  • {SNA} Allium cepa (Onion),

产品应用

  • 生化研究。配置培养基。营养学研究。

相关文献及参考

  • [2]. Mortell KH, et al. Structure-activity relationships of alpha-amino acid ligands for the alpha2delta subunit of voltage-gated calcium channels. Bioorg Med Chem Lett. 2006 Mar 1;16(5):1138-41.
  • [3]. Glushakov AV, et al. Specific inhibition of N-methyl-D-aspartate receptor function in rat hippocampal neurons by L-phenylalanine at concentrations observed during phenylketonuria. Mol Psychiatry. 2002;7(4):359-67.
  • [4]. Glushakov AV, et al. L-phenylalanine selectively depresses currents at glutamatergic excitatory synapses. J Neurosci Res. 2003 Apr 1;72(1):116-24.
  • [5]. Glushakov AV, et al. Long-term changes in glutamatergic synaptic transmission in phenylketonuria. Brain. 2005 Feb;128(Pt 2):300-7.
  • 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).
  • Merck:

安全信息

Warnings IRRITANT
Signal word Warning
GHS Symbol
WGK Germany1
Safety Statements
  • S24/25 Avoid contact with skin and eyes 避免皮肤和眼睛接触;
Risk Statements
  • R36/37/38 Irritating to eyes, respiratory system and skin 对眼睛、呼吸系统和皮肤有刺激性
Precautionary statements
  • P261 Avoid breathing dust/fume/gas/mist/vapours/spray. 避免吸入粉尘/烟/气体/烟雾/蒸汽/喷雾。
  • P262 Do not get in eyes, on skin, or on clothing. 不要接触眼睛,皮肤或衣服。
  • P264 Wash hands thoroughly after handling. 处理后要彻底洗净双手。
  • P264+P265
  • P271 Use only outdoors or in a well-ventilated area.? 只能在室外或通风良好的地方使用。
  • P280 Wear protective gloves/protective clothing/eye protection/face protection. 戴防护手套/防护服/眼睛的保护物/面部保护物。
  • P304+P340
  • P305+P351+P338
  • P319
  • P337+P313
  • P337+P317
  • P403+P233
  • P405 Store locked up. 上锁保管。
  • P501 Dispose of contents/container to..… 处理内容物/容器.....
Personal Protective Equipment Eyeshields, Gloves, type N95 (US), type P1 (EN143) respirator filter
RTECSAY7535000
Storage condition 2-8°C {LY} 2-8°C Store at RT. {} {LY} 2-8°C {} {} {LY} 2-8°C {} {} {} {LY} 2-8°C {} {} {} {} {LY} 2-8°C {} {} {} {} {} {LY} 2-8°C {} {} {} {} {} {} {LY} 2-8°C {} {} {} {} {} {} {} {LY} 2-8°C {} {} {} {} {} {} {} {} {LY} 2-8°C {} {} {} {} {} {} {} {} {} {LY} 2-8°C {} {} {} {} {} {} {} {} {} {} {LY} 2-8°C {} {} {} {} {} {} {} {} {} {} {} {LY} 2-8°C {} {} {} {} {} {} {} {} {} {} {} {} {LY} 2-8°C {} {} {} {} {} {} {} {} {} {} {} {} {} {LY} 2-8°C {} {} {} {} {} {} {} {} {} {} {} {} {} {} {LY} 2-8°C {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {LY} 2-8°C {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {LY} 2-8°C {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {LY} 2-8°C {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {LY} 2-8°C {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {LY} 2-8°C {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {LY} 2-8°C {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {LY} 2-8°C
TYPE OF TEST            : LD50 - Lethal dose, 50 percent kill
ROUTE OF EXPOSURE       : Intraperitoneal
SPECIES OBSERVED        : Rodent - rat
DOSE/DURATION           : 5287 mg/kg
TOXIC EFFECTS :
   Lungs, Thorax, or Respiration - dyspnea
   Nutritional and Gross Metabolic - body temperature decrease
REFERENCE :
   ABBIA4 Archives of Biochemistry and Biophysics.  (Academic Press, Inc., 1 E.
   First St., Duluth, MN 55802)  V.31-    1951-  Volume(issue)/page/year:
   58,253,1955

TYPE OF TEST            : LD50 - Lethal dose, 50 percent kill
ROUTE OF EXPOSURE       : Intraperitoneal
SPECIES OBSERVED        : Rodent - mouse
DOSE/DURATION           : >1322 mg/kg
TOXIC EFFECTS :
   Details of toxic effects not reported other than lethal dose value
REFERENCE :
   YKKZAJ Yakugaku Zasshi.  Journal of Pharmacy.  (Nippon Yakugakkai, 2-12-15
   Shibuya, Shibuya-ku, Tokyo 150, Japan)  No.1-    1881-
   Volume(issue)/page/year: 97,1117,1977

TYPE OF TEST            : Sister chromatid exchange
TEST SYSTEM             : Human Lymphocyte
DOSE/DURATION           : 10 mg/L
REFERENCE :
   MUREAV Mutation Research.  (Elsevier Science Pub. B.V., POB 211, 1000 AE
   Amsterdam, Netherlands) V.1-    1964-  Volume(issue)/page/year: 280,279,1992

TYPE OF TEST            : Mutation in microorganisms
TEST SYSTEM             : Bacteria - Escherichia coli
DOSE/DURATION           : 2 mmol/L
REFERENCE :
   MUREAV Mutation Research.  (Elsevier Science Pub. B.V., POB 211, 1000 AE
   Amsterdam, Netherlands) V.1-    1964-  Volume(issue)/page/year: 161,113,1986

TYPE OF TEST            : TDLo - Lowest published toxic dose
ROUTE OF EXPOSURE       : Oral
SPECIES OBSERVED        : Rodent - rat
DOSE                    : 30 gm/kg
SEX/DURATION            : female 10-14 day(s) after conception
TOXIC EFFECTS :
   Reproductive - Specific Developmental Abnormalities - Central Nervous System
   Reproductive - Effects on Newborn - behavioral
REFERENCE :
   TJADAB Teratology, The International Journal of Abnormal Development. (Alan
   R. Liss, Inc., 41 E. 11th St., New York, NY 10003)  V.1-    1968-
   Volume(issue)/page/year: 36,470,1987

TYPE OF TEST            : TDLo - Lowest published toxic dose
ROUTE OF EXPOSURE       : Oral
SPECIES OBSERVED        : Rodent - rat
DOSE                    : 220 gm/kg
SEX/DURATION            : male 2 week(s) pre-mating
                          female 2 week(s) pre-mating  - 3 week(s) post-birth
TOXIC EFFECTS :
   Reproductive - Effects on Newborn - weaning or lactation index (e.g., #
   alive at weaning per # alive at day 4)
   Reproductive - Effects on Newborn - growth statistics (e.g.%, reduced weight
   gain)
REFERENCE :
   NETOD7 Neurobehavioral Toxicology.  (Fayetteville, NY)  V.1-2, 1979-80. For
   publisher information, see NTOTDY.  Volume(issue)/page/year: 1,79,1979

TYPE OF TEST            : TDLo - Lowest published toxic dose
ROUTE OF EXPOSURE       : Intraperitoneal
SPECIES OBSERVED        : Rodent - ra

TYPE OF TEST            : TDLo - Lowest published toxic dose
ROUTE OF EXPOSURE       : Subcutaneous
SPECIES OBSERVED        : Rodent - mouse
DOSE                    : 30 mg/kg
SEX/DURATION            : female 3 day(s) pre-mating
TOXIC EFFECTS :
   Reproductive - Maternal Effects - uterus, cervix, vagina
REFERENCE :
   BIRSB5 Biology of Reproduction, Supplement.  (Champaign, IL)  No.1-4,
   1969-71(?).   Discontinued. For publisher information, see BIREBV.
   Volume(issue)/page/year: 20(Suppl 1),133A,1979

Hazard statements
  • H319 Causes serious eye irritation 严重刺激眼睛
  • H335 May cause respiratory irritation 可能导致呼吸道刺激

其他信息

  • 下游产品:DL-色氨酸 --> DL-苯丙氨酸 --> 阿斯巴甜 --> [MET5]脑啡肽 --> BOC-L-苯丙氨酸 --> BOC-D-苯丙氨酸
  • 方法三:脱脂大豆用盐酸水解后,除去酸性氨基酸,用活性炭或脱色树脂吸附苯丙氨酸、酪氨酸和色素后,溶出苯丙氨酸,分离而得。 从水解液分离时也可采取先形成难溶于水的2,5-二溴苯磺酸盐,利用溶解度的差异,与亮氨酸、精氨酸等分离而得。
  • 图谱信息:L-苯丙氨酸(63-91-2)质谱(MS) L-苯丙氨酸(63-91-2)核磁图( 13 CNMR) L-苯丙氨酸(63-91-2)红外图谱(IR2) L-苯丙氨酸(63-91-2)红外图谱(IR1) L-苯丙氨酸(63-91-2)Raman光谱 L-苯丙氨酸(63-91-2)核磁图( 1 HNMR)
  • Alfa Aesar:L-苯基丙氨酸,99% L-Phenylalanine, 99%(63-91-2)
  • 用途三:营养增补剂。必需氨基酸之一。在大多数食品的蛋白质中几乎非限制氨基酸。可添加于焙烤食品,除强化苯丙氨酸外,与糖类起氨基一羰基反应,可改善食品香味。 也可用于配制氨基酸输液及综合氨基酸制剂。 按我国GB 2760—86规定可用作香料。
  • 在真空中升华。水中溶解度(g/L):27 g/L (20°C);极微溶于乙醇和甲
  • 所属类别一:生物化学品: 生化试剂: 氨基酸及其衍生物
  • 方法四:合成法制备苯丙氨酸的收率低,通常从天然产物中提取。将脱脂大豆用盐酸水解后,除去酸性氨基酸,用活性炭或脱色树脂吸附苯丙氨酸和酪氨酸。然后,用溶剂将苯丙氨酸溶出、分离。也可采用先把水解液中的苯丙氨酸转变为2,5-二溴苯磺酸盐,然后利用溶解度的差异,从亮氨酸、精氨酸等氨基酸中分离出来的方法。
  • FEMA:3585
  • 比旋光度:-34.1 ° (c=2, water, dry basis)
  • 方法二:L-苯丙氨酸的制备方法很多, 有蛋白质水解提取法, 直接发酵法, 化学合成等。 化学合成法有苯甲醛法和苯乙醛法。 苯甲醛法 以苯甲醛和乙酰甘氨酸作用生成乙酰氨基桂皮酸, 然后催化加氢还原, 得乙酰-DL-苯丙氨酸(Ac-DL-phe), 最后经氨基酰化酶水解, 可拆分生成L-苯丙氨酸。 利用氨基酰化酶的专一性, 只水解Ac-L-phe的酰氨键, 生成L-phe, 而不能水解Ac-D-phe的酰胺。 然后根据L-phe和Ac-D-phe在水中的溶解度不同进行分离。而分离出的Ac-D-phe又可经消旋化生成Ac-DL-phe。 再一次重复水解、分离。 依次类推, 可将Ac-DL-phe全部转化为L-phe。 固定化氨基酰化酶的制备 将DEAE-sephadexa-50放入去离子水中充分浸泡后, 再依次用10倍量的0.5mol/L HCl和0.5mol/L NaOH溶液充分搅拌处理30min。 然后用去离子水洗至中性, 最后分别用0.1mol/L及0.01mol/L的pH=7.0的磷酸缓冲液处理1-2h, 滤干, 备用。 取经培养40-50h 的米麯扩大麯, 用其6倍量的支离子水分2次提取, 提取液用2mol/L的NaOH溶液调pH至6.7-7.0。 然后按100L酶液和1kg湿DEAE-sephadex A-50的比例混合, 于0-4℃搅拌吸附4-5h后, 过滤取DEAE-sephadexA-50, 并分别用去离子水0.1mol/L NaAc溶液、0.01mol/L 的pH=7.0的磷酸缓冲液洗涤3-4次。 过滤得固定化氨基酰化酶, 加1%甲苯放入冷库中贮存备用。 酶水解 在1000L水解罐中, 加入700L 0.1mol/L Ac-DL-phe钠盐溶液, 再逐步加入6mol/L的HCl调溶液pH至6.7-7.0, 再加入15-20kg固定化氨基酰化酶, 维持50℃约4h进行酶选择性水解反应后, 过滤取滤液, 得酶水解液(含L-phe和Ac-D-phe混合液)。 分离 将酶水解液用6mol/L的HCl调pH至4.8-5.1, 减压浓缩至35L左右, 并将其放置于0℃结晶过夜, 过滤取结晶, 用10L冷乙醇洗涤, 于80℃烘干3-
  • 用途五:生化研究。配置培养基。营养学研究。
  • 毒性:LD 50 5287mg/kg(大鼠,腹腔注射)。可安全用于食品(FDA,§172.320,2000)。

系列性分类