L-Pyroglutamic Acid L-焦谷氨酸

CAS 98-79-3 MFCD00005272

化学结构图

98-79-3
SMILES: O=C1CCC(C(=O)O)N1

化学属性

Mol. FormulaC5H7NO3
Mol. Weight129.11
Density1.38
Melting Point155-162°C
TSCAYes
Solubility10-15 G/100 ML (20 ºC)
Appearance 无色结晶。熔点162-163℃,溶于水、醇、丙酮和冰醋酸,微溶于乙酸乙酯,不溶于醚。
Refractive index-10 ° (C=5, H2O)
Boiling Point239.15 °C at 760 mmHg

别名和识别编码

Chemical NameL-Pyroglutamic Acid
CAS Number98-79-3
Alfabeta NamePYROH -
MDL NumberMFCD00005272
EC Number202-700-3
Beilstein Registry Number22,284
Synonym L-Pyroglutamic acid {LY} L-Pyroglutamic acid {} {LY} L-Pyroglutamic acid {} {} {LY} L-Pyroglutamic acid {} {} {} {LY} L-Pyroglutamic acid {} {} {} {} {LY} L-Pyroglutamic acid {} {} {} {} {} {LY} L-Pyroglutamic acid {} {} {} {} {} {} {LY} L-Pyroglutamic acid {} {} {} {} {} {} {} {LY} L-Pyroglutamic acid {} {} {} {} {} {} {} {} {LY} L-Pyroglutamic acid {} {} {} {} {} {} {} {} {} {LY} L-Pyroglutamic acid {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {LY} L-Pyroglutamic acid {} {} {} {} {} {} {} {} {} {} {} {LY} L-Pyroglutamic acid {} {} {} {} {} {} {} {} {} {} {} {} {LY} L-Pyroglutamic acid {} {} {} {} {} {} {} {} {} {} {} {} {} { {} {} {} {} {} {} {} {} {} {} {} {} {} {LY} L-Pyroglutamic acid {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} { {} {} {} {} {} {} {} {} {} {} {} {} {} {} {LY} L-Pyroglutamic acid {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {LY} L-Pyroglutamic acid {} {} {} {} {} {} {} {} {} {} {} {}
PubChem Substance ID7405
Merck Number8001
Chemical Name TranslationL-焦谷氨酸
Reaxys-RN82132
LabNetwork Molecule IDLN00196118
InChIInChI=1S/C5H7NO3/c7-4-2-1-3(6-4)5(8)9/h3H,1-2H2,(H,6,7)(H,8,9)/t3-/m0/s1
Canonical SMILESO=C(O)[C@H](CC1)NC1=O
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分类

  • {SNA} Analytical Standards, Analytical/Chromatography, Chromatography, EP Standards, EP Standards P - R,
  • {SNA} Analytical Standards,
  • {SNA} Chemical Biology, Chemical Synthesis, Peptide Chemistry, Pyroglutamine Derivatives, Unnatural Amino Acids & Derivatives
  • {SNA} Amino Acids, Asymmetric Synthesis, Chemical Synthesis, Chiral Resolution Reagents, Chiral Resolving Reagents, I - Z, Modified Amino Acids, 生化试剂
  • {SNA} Chemical Biology, Chemical Synthesis, Peptide Chemistry, Pyroglutamine Derivatives, Unnatural Amino Acid Derivatives
  • {SNA} Analytical Standards, Chromatography, EP Standards, EP Standards P - R,

产品应用

  • 非对称合成砌块。

相关文献及参考

  • Resolving agent for chiral bases: Helv. Chim. Acta, 41, 181 (1958). Versatile chiral starting material:
  • Reduction to the alcohol followed by reaction with benzaldehyde gives a bicyclic lactam which is a useful chiral synthon: J. Org. Chem., 51, 3140 (1986); Tetrahedron Lett., 32, 1379 (1991):
  • Short: EINECS
  • For use in an efficient synthesis of quinolizidine and indolizidine alkaloids, see: J. Org. Chem., 60, 717 (1995).
  • Merck: 14,8001
  • Merck: 14,8001 Beilstein:22,284
  • Short: III/5a

安全信息

Warnings IRRITANT
Signal word Warning
GHS Symbol
WGK Germany3
Safety Statements
  • S36 Wear suitable protective clothing 穿戴适当的防护服;
  • S26 In case of contact with eyes, rinse immediately with plenty of water and seek medical advice 眼睛接触后,立即用大量水冲洗并征求医生意见;
  • S60 This material and its container must be disposed of as hazardous waste 该物质及其容器必须作为危险废物处置;
  • S37 Wear suitable gloves 戴适当手套;
  • S36/37/39 Wear suitable protective clothing, gloves and eye/face protection 穿戴适当的防护服、手套和眼睛/面保护;
  • S37/39 Wear suitable gloves and eye/face protection 穿戴适当的手套和眼睛/面保护;
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
  • 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。
  • P362 Take off contaminated clothing and wash before reuse. 脱掉污染的衣服,清洗后方可重新使用
  • P264 Wash hands thoroughly after handling. 处理后要彻底洗净双手。
  • P261 Avoid breathing dust/fume/gas/mist/vapours/spray. 避免吸入粉尘/烟/气体/烟雾/蒸汽/喷雾。
  • P305+P351+P338
  • P332+P313
  • P305+P351+P338+P337+P313
  • P302+P350
  • P337+P313
  • P302+P352+P332+P313+P362+P364
Hazard statements
  • H315 Causes skin irritation 会刺激皮肤
  • 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
Personal Protective Equipment dust mask type N95 (US), Eyeshields, Gloves
RTECSTW3710000
Hazard Codes Xi
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       : Subcutaneous
SPECIES OBSERVED        : Rodent - rat
DOSE/DURATION           : >2 gm/kg
TOXIC EFFECTS :
   Details of toxic effects not reported other than lethal dose value
REFERENCE :
   USXXAM United States Patent Document.  (U.S. Patent Office, Box 9,
   Washington, DC 20231)  Volume(issue)/page/year: #4882359

TYPE OF TEST            : LD50 - Lethal dose, 50 percent kill
ROUTE OF EXPOSURE       : Oral
SPECIES OBSERVED        : Rodent - rat
DOSE/DURATION           : >1 gm/kg
TOXIC EFFECTS :
   Details of toxic effects not reported other than lethal dose value
REFERENCE :
   USXXAM United States Patent Document.  (U.S. Patent Office, Box 9,
   Washington, DC 20231)  Volume(issue)/page/year: #4882359

其他信息

  • 比旋光度:-27.5 ° (c=10, 1 N NaOH)
  • L-焦谷氨酸价格(试剂级):更新日期 产品编号 产品名称 包装 价格 2011/08/23 62020133 L-焦谷氨酸;L-焦性麸质酸; L-焦性胶氨酸; L-2-吡咯烷酮-5-羧酸 10g 59.3元 2011/04/16 P0573 L-焦谷氨酸 L-Pyroglutamic Acid 500G 1890元 2011/04/16 P0573 L-焦谷氨酸 L-Pyroglutamic Acid 25G 189元
  • F:21
  • 下游产品:5-(氨甲基)-1-甲基吡咯烷-2-酮 --> 表面活性剂PCA-N
  • 特点及用途:在人类皮肤中含有一种保湿功能的水溶性物质——天然保湿因子,其组成大致为氨基酸(含40%)、焦谷氨酸(含 12%)、无机盐类(Na、K、Ca、Mg等含18.5%)、其它有机物 (含29.5%)。所以,焦谷氨酸是皮肤天然保湿因子的主要组分之一,其保湿能力远超过甘油及丙二醇等。且无毒、无刺激,是现代护肤、护发化妆品的优良原料。焦谷氨酸还对酪氨酸氧化酶的活性有抑制作用,从而阻止“类黑素”物质在皮肤中沉积,对皮肤具有增白作用。对角质有软化作用,可用于指甲化妆品。除在化妆品中应用外,L-焦谷氨酸还可与其它一些有机化合物生成衍生物,在表面活性、透明光亮作用等方面具有特殊功效。也可用作表面活性剂,用于洗涤剂;化学试剂,用于外消旋胺的拆分;有机中间体。 L-焦谷氨酸又名L-焦性麸质酸、L-焦性胶氨酸。学名为L-2-吡咯烷酮-5-羧酸。从乙醇及石油醚混合液中析出者为无色正交晶系双锥体结晶,熔点162~163℃。能溶于水、醇、丙酮和冰醋酸,微溶于乙酸乙酯,不溶于醚。比旋光度-11.9°(c=2,H2O)。由42%谷氨酸水溶液经加热脱水、浓缩、结晶、洗涤、干燥制得。
  • MOL 文件:98-79-3.mol
  • 制备方法:L-焦谷氨酸是L-谷氨酸分子内脱去一分子水而形成,其制备过程简单,关键步骤是温度及脱水时间的控制。 (1)在500毫升烧杯内加入100克L-谷氨酸,用油浴加热烧杯,待温度升至145~150℃时,保温45分钟进行脱水反应。脱水后的溶液呈棕褐色。 (2)脱水反应结束后,将溶液倾倒入体积约为350毫升的沸水中,溶液全部溶于水中。冷却至40~50℃后,加入适量活性炭进行脱色(重复进行两次)。得到无色透明溶液。 (3)将步骤(2)制得的无色透明溶液直接加热蒸发浓缩到体积减至一半左右时,再转到水浴上继续浓缩至体积为1/3 左右,即可停止加热,并在热水浴中放冷缓慢使之结晶,10~ 20小时后即可制得无色棱形结晶。 L-焦谷氨酸在化妆品中的用量随配方而定。本品也可以50%浓缩液方式用于化妆品上。
  • 水中溶解度: 10-15% (20°C) ,溶于乙醇和丙酮。
  • 焦谷氨酸:焦谷氨酸系5-氧脯氨酸。由谷氨酸的α-NH2基和γ-羟基之间脱水形成分子内酰胺键而成;亦可由谷氨酰胺分子内失去酰氨基而成。如果谷胱甘肽合成酶缺陷,可引起焦谷氨酸血症,出现一系列临床症状。焦谷氨酸血症系由于谷胱甘肽合成酶缺陷而引起的一种有机酸代谢障碍性疾病。临床表现出生12~24小时发病,进行性溶血、黄疸、慢性代谢性酸中毒、智能障碍等;尿中含有焦谷氨酸、乳酸、α-去氧4羟乙酰乙酸内脂。治疗,对症、周岁后注
  • 存储注意事项:湿度敏感
  • 用途一:用于食品、医药、化妆品等行业
  • Acros Organics:L-焦谷氨酸 (S)-(-)-2-Pyrrolidone-5-carboxylicacid,98%(98-79-3)
  • 图谱信息:L-焦谷氨酸(98-79-3)红外图谱(IR1) L-焦谷氨酸(98-79-3)红外图谱(IR2) L-焦谷氨酸(98-79-3)核磁图( 1 HNMR) L-焦谷氨酸(98-79-3)质谱(MS) L-焦谷氨酸(98-79-3)核磁图( 13 CNMR)
  • 海关编码:29337900
  • MSDS 信息:L-5-Pyrrolidone-2-carboxylic acid(98-79-3).msds
  • 上游原料:谷氨酸
  • {Chemi
  • 用途二:用作有机合成中间体,食品添加剂等。

系列性分类


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