谷氨酸一铵 | 7558-63-6

• 物质功能分类: 生物化工 - 常见氨基酸及蛋白质类
• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 羧酸及其衍生物
• 中文名称: 谷氨酸一铵
• 中文别名: 谷氨酸铵；L-谷氨酸胺；L-谷氨酸-铵
• 英文名称: L-glutamate
• 英文别名: L-glutamic acid ; monoammonium salt；L-Glutaminsaeure; Monoammoniumsalz；azanium;(4S)-4-amino-5-hydroxy-5-oxopentanoate
• CAS: 7558-63-6
• 化学式: C₅H₉NO₄*H₃N
• mdl: MFCD00039098
• 分子量: 164.161
• InChiKey: PHKGGXPMPXXISP-DFWYDOINSA-N

物化性质

• 熔点：
  169 - 173°C
• 溶解度：
  可溶于酸水溶液（轻微）、甲醇（非常轻微）、水（轻微）
• LogP：
  -1.435 (est)
• 物理描述：
  White, practically odourless crystals or crystalline powder
• 旋光度：
  [α]D/20 between + 25,4° and + 26,4°; (10 % solution (anhydrous basis) in 2N HCl, 200 mm tube)

计算性质

• 辛醇/水分配系数(LogP)：
  -3.24
• 重原子数：
  11
• 可旋转键数：
  3
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.6
• 拓扑面积：
  104
• 氢给体数：
  3
• 氢受体数：
  5

安全信息

• 危险品标志：
  Xi
• 安全说明：
  S26,S36
• 危险类别码：
  R36/37/38
• WGK Germany：
  3
• RTECS号：
  MA1400000
• 海关编码：
  2923900090
• 危险性防范说明：
  P264,P280,P302+P352,P337+P313,P305+P351+P338,P362+P364,P332+P313
• 危险性描述：
  H315,H319
• 储存条件：
  -20°C

SDS

Version 1.2
Regulation (EC) No 1907/2006

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1 - Product and Company Information

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Product Name L-GLUTAMIC ACID MONOAMMONIUM

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2 - Hazards Identification

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3 - Composition/Information on Ingredients

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Product Name CAS # EC no Annex I
Index Number
L-GLUTAMIC ACID MONOAMMONIUM 7558-63-6 231-447-1 None
Formula C5H9NO4.H3N
Molecular Weight 164,2000 AMU
Synonyms Ammoniumglutaminat (German) * MAG * Monoammonium
glutamate

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4 - First Aid Measures

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AFTER INHALATION
If inhaled, remove to fresh air. If breathing becomes difficult,
call a physician.
AFTER SKIN CONTACT
In case of skin contact, flush with copious amounts of water for
at least 15 minutes. Remove contaminated clothing and shoes.
Call a physician.
AFTER EYE CONTACT
In case of contact with eyes, flush with copious amounts of
water for at least 15 minutes. Assure adequate flushing by
separating the eyelids with fingers. Call a physician.
AFTER INGESTION
If swallowed, wash out mouth with water provided person is
conscious. Call a physician.

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5 - Fire Fighting Measures

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SIGMA www.molbase.com
EXTINGUISHING MEDIA
Suitable: Water spray. Carbon dioxide, dry chemical powder, or
appropriate foam.
SPECIAL PROTECTIVE EQUIPMENT FOR FIREFIGHTERS
Wear self-contained breathing apparatus and protective clothing
to prevent contact with skin and eyes.

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6 - Accidental Release Measures

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PROCEDURE(S) OF PERSONAL PRECAUTION(S)
Wear protective equipment.
METHODS FOR CLEANING UP
Sweep up, place in a bag and hold for waste disposal. Avoid
raising dust. Ventilate area and wash spill site after material
pickup is complete.

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7 - Handling and Storage

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8 - Exposure Controls / Personal Protection

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ENGINEERING CONTROLS
Mechanical exhaust required.
PERSONAL PROTECTIVE EQUIPMENT
Special Protective Measures: Wear appropriate government approved
respirator, chemical-resistant gloves, safety goggles, other
protective clothing.

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9 - Physical and Chemical Properties

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Appearance Physical State: Solid
Property Value At Temperature or Pressure
pH N/A
BP/BP Range N/A
MP/MP Range N/A
Flash Point N/A
Flammability N/A
Autoignition Temp N/A
Oxidizing Properties N/A
Explosive Properties N/A
Explosion Limits N/A
Vapor Pressure N/A
Partition Coefficient N/A
Viscosity N/A
Vapor Density N/A
Saturated Vapor Conc. N/A
Evaporation Rate N/A
Bulk Density N/A
Decomposition Temp. N/A
Solvent Content N/A
Water Content N/A
Surface Tension N/A
Conductivity N/A
Miscellaneous Data N/A
Solubility N/A
SIGMA www.molbase.com

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10 - Stability and Reactivity

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STABILITY
Stable: Stable.
HAZARDOUS POLYMERIZATION
Hazardous Polymerization: Will not occur

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11 - Toxicological Information

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RTECS NUMBER: MA1400000
ACUTE TOXICITY
LD50
Intraperitoneal
Rat
1 GM/KG
Remarks: Behavioral:Muscle contraction or spasticity.
Behavioral:Coma. Behavioral:Convulsions or effect on seizure
threshold.
ROUTE OF EXPOSURE
Multiple Routes: May be harmful by inhalation, ingestion, or
skin absorption. May cause irritation.
CONDITIONS AGGRAVATED BY EXPOSURE
The toxicological properties have not been thoroughly
investigated.

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12 - Ecological Information

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No data available.

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13 - Disposal Considerations

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SUBSTANCE DISPOSAL
Dissolve or mix the material with a combustible solvent and burn
in a chemical incinerator equipped with an afterburner and
scrubber. Observe all federal, state, and local environmental
regulations.

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14 - Transport Information

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RID/ADR
Non-hazardous for road transport.
IMDG
Non-hazardous for sea transport.
IATA
Non-hazardous for air transport.

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15 - Regulatory Information

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COUNTRY SPECIFIC INFORMATION
Germany
WGK: 3
SIGMA www.molbase.com
Self-Classification

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16 - Other Information

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WARRANTY
The above information is believed to be correct but does not
purport to be all inclusive and shall be used only as a guide. The
information in this document is based on the present state of our
knowledge and is applicable to the product with regard to
appropriate safety precautions. It does not represent any
guarantee of the properties of the product. Inc.,
shall not be held liable for any damage resulting from handling or
from contact with the above product. See reverse side of invoice
or packing slip for additional terms and conditions of sale.
Copyright 2010 Co. License granted to make
unlimitedpaper copies for internal use only.
DISCLAIMER
For R&D use only. Not for drug, household or other uses.
SIGMA www.molbase.com

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SECTION 16 - ADDITIONAL INFORMATION
N/A

制备方法与用途

鉴别试验

此试验参考“02020，L-谷氨酸一钠”的标准。取10%试样液10毫升，加入1摩尔/升盐酸5.6毫升。静置后应产生白色谷氨酸结晶沉淀。摇匀后继续加入1摩尔/升盐酸至总量为6毫升，搅拌后谷氨酸应当溶解。

10%试样液的铵盐试验（IT-3）结果呈阳性。

含量分析

准确称取约250毫克试样，溶于100毫升冰醋酸中。若先在醋酸中加入数滴水，则能加速试样的溶解。使用0.1摩尔/升高氯酸进行滴定，终点由电位差测定。每1毫升0.1摩尔/升高氯酸相当于L-谷氨酸一铵（C5H12N2O4·H2O）9.109毫克。

毒性

此物质被认为是GRAS（一般认为安全，FDA编号：§182．1500，2000）。FAO/WHO（2001年）未对ADI进行限定。

化学性质

L-谷氨酸一铵为白色、基本无臭的易流动结晶性粉末，具有特殊的滋味。该物质极易溶于水，几乎不溶于普通有机溶剂。其5%水溶液的pH值范围为6.0～7.0。

用途

作为调味剂和代盐剂使用。

生产方法

通过发酵法获得L-谷氨酸后，与氢氧化铵或碳酸铵中和并进行脱色结晶精制而成。

反应信息

• 作为反应物：
  描述：

  谷氨酸一铵 在 乙酰氯 作用下， 反应 2.33h， 生成 dipropyl (2S)-2-(2,2,3,3,4,4,4-heptafluorobutanoylamino)pentanedioate
  参考文献：
  名称：

  Use of L ‐[ ¹⁵ N] glutamic acid and homoglutathione to determine both glutathione synthesis and concentration by gas chromatography‐mass spectrometry (GCMS)

  摘要：

  描述了一种使用气相色谱质谱法同时测量生物样品中谷胱甘肽富集和浓度的方法。该方法基于谷胱甘肽 N,S-乙氧基羰基甲酯衍生物的制备，并使用高谷胱甘肽（谷氨酰-半胱氨酰-丙氨酸）作为内标。还报道了测定谷氨酸浓度和富集的程序。两种方法的日内和日间分析间变异系数均小于 5%，已知添加量的谷胱甘肽和谷氨酸的回收率接近 100%。总而言之，这些方法允许使用 L-[15N] 谷氨酸输注测定红细胞中的谷胱甘肽浓度和分数合成率。该方法应用于体内，以研究与对照过夜禁食相比，72 小时禁食对单只狗红细胞谷胱甘肽的影响。 72 小时禁食与红细胞谷胱甘肽水平下降 39% 相关（2.9 ± 0.4 与 4.7 ± 0.5 mmol l−1，禁食与对照），而谷胱甘肽合成分数没有变化（67.4% 与 71.3% d−1，禁食）与对照）。版权所有 © 2001 约翰威利父子有限公司

  DOI：

  10.1002/jms.185
• 作为产物：
  描述：

  L-谷氨酰胺 在 L-glutamate dehydrogenase 作用下， 反应 0.17h， 生成 谷氨酸一铵
  参考文献：
  名称：

  Crystal structure of salt-tolerant glutaminase from Micrococcus luteus K-3 in the presence and absence of its product l-glutamate and its activator Tris

  摘要：

  Glutaminase from Micrococcus luteus K‐3 [Micrococcus glutaminase (Mglu); 456 amino acid residues (aa); 48 kDa] is a salt‐tolerant enzyme. Our previous study determined the structure of its major 42‐kDa fragment. Here, using new crystallization conditions, we determined the structures of the intact enzyme in the presence and absence of its product l‐glutamate and its activator Tris, which activates the enzyme by sixfold. With the exception of a ‘lid’ part (26‐29 aa) and a few other short stretches, the structures were all very similar over the entire polypeptide chain. However, the presence of the ligands significantly reduced the length of the disordered regions: 41 aa in the unliganded structure (N), 21 aa for l‐glutamate (G), 8 aa for Tris (T) and 6 aa for both l‐glutamate and Tris (TG). l‐Glutamate was identified in both the G and TG structures, whereas Tris was only identified in the TG structure. Comparison of the glutamate‐binding site between Mglu and salt‐labile glutaminase (YbgJ) from Bacillus subtilis showed significantly smaller structural changes of the protein part in Mglu. A comparison of the substrate‐binding pocket of Mglu, which is highly specific for l‐glutamine, with that of Erwinia carotovora asparaginase, which has substrates other than l‐glutamine, shows that Mglu has a larger substrate‐binding pocket that prevents the binding of l‐asparagine with proper interactions.Structured digital abstract MINT‐7305730: Mglu (uniprotkb:Q4U1A6) and Mglu (uniprotkb:Q4U1A6) bind (MI:0407) by x‐ray crystallography (MI:0114)

  DOI：

  10.1111/j.1742-4658.2009.07523.x

文献信息

• Voss; Guttmann, Chemische Berichte, 1930, vol. 63, p. 1731
  作者：Voss、Guttmann

  DOI：——

  日期：——
• An exceptionally mild deprotection of phthalimides
  作者：John O. Osby、Michael G. Martin、Bruce Ganem

  DOI：10.1016/s0040-4039(01)81169-2

  日期：1984.1
• Crystal structure of salt-tolerant glutaminase from Micrococcus luteus K-3 in the presence and absence of its product l-glutamate and its activator Tris
  作者：Kazuaki Yoshimune、Yasuo Shirakihara、Mamoru Wakayama、Isao Yumoto

  DOI：10.1111/j.1742-4658.2009.07523.x

  日期：2010.2

  Glutaminase from Micrococcus luteus K‐3 [Micrococcus glutaminase (Mglu); 456 amino acid residues (aa); 48 kDa] is a salt‐tolerant enzyme. Our previous study determined the structure of its major 42‐kDa fragment. Here, using new crystallization conditions, we determined the structures of the intact enzyme in the presence and absence of its product l‐glutamate and its activator Tris, which activates the enzyme by sixfold. With the exception of a ‘lid’ part (26‐29 aa) and a few other short stretches, the structures were all very similar over the entire polypeptide chain. However, the presence of the ligands significantly reduced the length of the disordered regions: 41 aa in the unliganded structure (N), 21 aa for l‐glutamate (G), 8 aa for Tris (T) and 6 aa for both l‐glutamate and Tris (TG). l‐Glutamate was identified in both the G and TG structures, whereas Tris was only identified in the TG structure. Comparison of the glutamate‐binding site between Mglu and salt‐labile glutaminase (YbgJ) from Bacillus subtilis showed significantly smaller structural changes of the protein part in Mglu. A comparison of the substrate‐binding pocket of Mglu, which is highly specific for l‐glutamine, with that of Erwinia carotovora asparaginase, which has substrates other than l‐glutamine, shows that Mglu has a larger substrate‐binding pocket that prevents the binding of l‐asparagine with proper interactions.Structured digital abstract MINT‐7305730: Mglu (uniprotkb:Q4U1A6) and Mglu (uniprotkb:Q4U1A6) bind (MI:0407) by x‐ray crystallography (MI:0114)
• Use of <scp>L</scp> ‐[ ¹⁵ N] glutamic acid and homoglutathione to determine both glutathione synthesis and concentration by gas chromatography‐mass spectrometry (GCMS)
  作者：Bernard Humbert、Patrick Nguyen、Christiane Obled、Christine Bobin、Anne Vaslin、Shawn Sweeten、Dominique Darmaun

  DOI：10.1002/jms.185

  日期：2001.7

  A method for simultaneous measurement of both glutathione enrichment and concentration in a biological sample using gas chromatography mass spectrometry is described. The method is based on the preparation of N,S-ethoxycarbonylmethyl ester derivatives of glutathione, and the use of homoglutathione (glutamyl–cysteinyl–alanine) as an internal standard. A procedure for determination of glutamate concentration and enrichment is also reported. Both methods have within-day and day-to-day inter-assay coefficients of variation less than 5%, and recoveries of known added amounts of glutathione and glutamate are close to 100%. Taken together, these methods allowed determination of glutathione concentration and fractional synthesis rate in red blood cells using L-[15N] glutamic acid infusion. This approach was applied in vivo to investigate the effects of a 72 h fast, compared with a control overnight fast, on erythrocyte glutathione in a single dog. The 72 h fast was associated with a 39% decline in erythrocyte glutathione level, (2.9 ± 0.4 versus 4.7 ± 0.5 mmol l−1, fasting versus control) with no change in glutathione fractional synthesis (67.4 versus 71.3% d−1, fasting versus control). Copyright © 2001 John Wiley & Sons, Ltd.

  描述了一种使用气相色谱质谱法同时测量生物样品中谷胱甘肽富集和浓度的方法。该方法基于谷胱甘肽 N,S-乙氧基羰基甲酯衍生物的制备，并使用高谷胱甘肽（谷氨酰-半胱氨酰-丙氨酸）作为内标。还报道了测定谷氨酸浓度和富集的程序。两种方法的日内和日间分析间变异系数均小于 5%，已知添加量的谷胱甘肽和谷氨酸的回收率接近 100%。总而言之，这些方法允许使用 L-[15N] 谷氨酸输注测定红细胞中的谷胱甘肽浓度和分数合成率。该方法应用于体内，以研究与对照过夜禁食相比，72 小时禁食对单只狗红细胞谷胱甘肽的影响。 72 小时禁食与红细胞谷胱甘肽水平下降 39% 相关（2.9 ± 0.4 与 4.7 ± 0.5 mmol l−1，禁食与对照），而谷胱甘肽合成分数没有变化（67.4% 与 71.3% d−1，禁食）与对照）。版权所有 © 2001 约翰威利父子有限公司