N-对硝基苯甲酰谷氨酸 | 6758-40-3

• 物质功能分类: 生物化工 - 氨基酸及其衍生物 - 谷氨酸类衍生物
• 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: N-对硝基苯甲酰谷氨酸
• 中文别名: N-对硝基苯甲酰-L-谷氨酸半水合物；N-对硝基苯甲酰-L-谷氨酸；N-(4-硝基苯甲酰)谷氨酸
• 英文名称: N-p-nitrobenzoyl-L-glutamic acid
• 英文别名: (S)-2-(4-Nitrobenzamido)pentanedioic acid；(2S)-2-[(4-nitrobenzoyl)amino]pentanedioic acid
• CAS: 6758-40-3
• 化学式: C₁₂H₁₂N₂O₇
• mdl: MFCD00066818
• 分子量: 296.236
• InChiKey: NOJZBJAFCSWMKC-VIFPVBQESA-N

物化性质

• 熔点：
  117-118 °C(lit.)
• 沸点：
  619.9±55.0 °C(Predicted)
• 密度：
  1.501±0.06 g/cm3(Predicted)
• 溶解度：
  乙酸乙酯（微溶）、甲醇（微溶）
• 稳定性/保质期：
  避免与强氧化剂接触。

计算性质

• 辛醇/水分配系数(LogP)：
  0.5
• 重原子数：
  21
• 可旋转键数：
  6
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.25
• 拓扑面积：
  150
• 氢给体数：
  3
• 氢受体数：
  7

安全信息

• WGK Germany：
  3
• 海关编码：
  2924299090
• 危险性防范说明：
  P261,P305+P351+P338
• 危险性描述：
  H302,H315,H319,H335
• 储存条件：
  密封保存，应储存在阴凉干燥的仓库中。

SDS

Name:	N-(p-nitrobenzoyl)-l-glutamic acid hemi- hydrate 98% Material Safety Data Sheet
Synonym:	None
CAS:	6758-40-3

Section 1 - Chemical Product MSDS Name:N-(p-nitrobenzoyl)-l-glutamic acid hemi- hydrate 98% Material Safety Data Sheet
Synonym:None

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Section 2 - COMPOSITION, INFORMATION ON INGREDIENTS

CAS#	Chemical Name	content	EINECS#
6758-40-3	N-(p-nitrobenzoyl)-l-glutamic acid hem	98.0	229-820-9

Hazard Symbols: None Listed.
Risk Phrases: None Listed.

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Section 3 - HAZARDS IDENTIFICATION
EMERGENCY OVERVIEW
The toxicological properties of this material have not been fully investigated.
Potential Health Effects
Eye:
May cause eye irritation.
Skin:
May cause skin irritation.
Ingestion:
May cause irritation of the digestive tract. The toxicological properties of this substance have not been fully investigated.
Inhalation:
May cause respiratory tract irritation. The toxicological properties of this substance have not been fully investigated.
Chronic:
No information found.

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Section 4 - FIRST AID MEASURES
Eyes: Flush eyes with plenty of water for at least 15 minutes, occasionally lifting the upper and lower eyelids. Get medical aid immediately.
Skin:
Get medical aid. Flush skin with plenty of water for at least 15 minutes while removing contaminated clothing and shoes. Wash clothing before reuse.
Ingestion:
If victim is conscious and alert, give 2-4 cupfuls of milk or water.
Never give anything by mouth to an unconscious person. Get medical aid immediately.
Inhalation:
Remove from exposure and move to fresh air immediately. If not breathing, give artificial respiration. If breathing is difficult, give oxygen. Get medical aid.
Notes to Physician:
Antidote: None reported.

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Section 5 - FIRE FIGHTING MEASURES
General Information:
As in any fire, wear a self-contained breathing apparatus in pressure-demand, MSHA/NIOSH (approved or equivalent), and full protective gear. During a fire, irritating and highly toxic gases may be generated by thermal decomposition or combustion.
Extinguishing Media:
Use water spray, dry chemical, carbon dioxide, or appropriate foam.

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Section 6 - ACCIDENTAL RELEASE MEASURES
General Information: Use proper personal protective equipment as indicated in Section 8.
Spills/Leaks:
Clean up spills immediately, observing precautions in the Protective Equipment section. Sweep up or absorb material, then place into a suitable clean, dry, closed container for disposal. Avoid generating dusty conditions. Provide ventilation.

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Section 7 - HANDLING and STORAGE
Handling:
Wash thoroughly after handling. Remove contaminated clothing and wash before reuse. Use with adequate ventilation. Minimize dust generation and accumulation. Avoid contact with eyes, skin, and clothing. Keep container tightly closed. Avoid ingestion and inhalation.
Storage:
Keep container closed when not in use. Store in a tightly closed container. Store in a cool, dry, well-ventilated area away from incompatible substances.

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Section 8 - EXPOSURE CONTROLS, PERSONAL PROTECTION
Engineering Controls:
Use adequate ventilation to keep airborne concentrations low.
Exposure Limits CAS# 6758-40-3: Personal Protective Equipment Eyes: Wear appropriate protective eyeglasses or chemical safety goggles as described by OSHA's eye and face protection regulations in 29 CFR 1910.133 or European Standard EN166.
Skin:
Wear appropriate protective gloves to prevent skin exposure.
Clothing:
Wear appropriate protective clothing to prevent skin exposure.
Respirators:
Follow the OSHA respirator regulations found in 29 CFR 1910.134 or European Standard EN 149. Use a NIOSH/MSHA or European Standard EN 149 approved respirator if exposure limits are exceeded or if irritation or other symptoms are experienced.

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Section 9 - PHYSICAL AND CHEMICAL PROPERTIES

Physical State: Powder
Color: off-white
Odor: Not available.
pH: Not available.
Vapor Pressure: Not available.
Viscosity: Not available.
Boiling Point: @ 760.00mm Hg
Freezing/Melting Point: 117.00 - 118.00 deg C
Autoignition Temperature: Not available.
Flash Point: Not available.
Explosion Limits, lower: N/A
Explosion Limits, upper: N/A
Decomposition Temperature:
Solubility in water:
Specific Gravity/Density:
Molecular Formula: C12H12N2O7.0.5H2O
Molecular Weight: 305.25

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Section 10 - STABILITY AND REACTIVITY
Chemical Stability:
Stable under normal temperatures and pressures.
Conditions to Avoid:
Incompatible materials, dust generation, strong oxidants.
Incompatibilities with Other Materials:
Strong oxidizing agents.
Hazardous Decomposition Products:
Carbon monoxide, oxides of nitrogen, irritating and toxic fumes and gases, carbon dioxide.
Hazardous Polymerization: Has not been reported

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Section 11 - TOXICOLOGICAL INFORMATION
RTECS#:
CAS# 6758-40-3 unlisted.
LD50/LC50:
Not available.
Carcinogenicity:
N-(p-nitrobenzoyl)-l-glutamic acid hemi- hydrate, - Not listed by ACGIH, IARC, or NTP.

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Section 12 - ECOLOGICAL INFORMATION

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Section 13 - DISPOSAL CONSIDERATIONS
Dispose of in a manner consistent with federal, state, and local regulations.

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Section 14 - TRANSPORT INFORMATION

IATA
Not regulated as a hazardous material.
IMO
Not regulated as a hazardous material.
RID/ADR
Not regulated as a hazardous material.

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Section 15 - REGULATORY INFORMATION

European/International Regulations
European Labeling in Accordance with EC Directives
Hazard Symbols: Not available.
Risk Phrases:
Safety Phrases:
S 24/25 Avoid contact with skin and eyes.
S 28A After contact with skin, wash immediately with
plenty of water.
S 37 Wear suitable gloves.
S 45 In case of accident or if you feel unwell, seek
medical advice immediately (show the label where
possible).
WGK (Water Danger/Protection)
CAS# 6758-40-3: No information available.
Canada
None of the chemicals in this product are listed on the DSL/NDSL list.
CAS# 6758-40-3 is not listed on Canada's Ingredient Disclosure List.
US FEDERAL
TSCA
CAS# 6758-40-3 is not listed on the TSCA inventory.
It is for research and development use only.

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SECTION 16 - ADDITIONAL INFORMATION
N/A

制备方法与用途

化学性质：固体结晶，熔点为117-118℃。
用途：该物质是维生素M（叶酸）的中间体。
生产方法：通过将对硝基苯甲酰氯与谷氨酸进行缩合反应制得。

反应信息

• 作为反应物：
  描述：

  N-对硝基苯甲酰谷氨酸 在 乙酸乙酯 、 三乙胺 作用下， 生成 N-(4-nitro-benzoyl)-L-glutamic acid bis-benzylamide
  参考文献：
  名称：

  关于活化的酯。三，氨基酸和肽衍生物的活化酯与胺和氨基酸酯的反应

  摘要：

  使许多氨基酸和肽衍生物的活化酯与各种有机胺，包括氨基酸酯反应。获得的良好收率和温和的反应条件使得活化的酯化酰化方法似乎可以在肽合成中很好地使用。芳香胺和仲胺的氨解仅缓慢进行，但是通过强叔胺和酸的催化作用可大大促进该反应。

  DOI：

  10.1002/hlca.19550380111
• 作为产物：
  描述：

  N-(4-硝基苯甲酰)-L-谷氨酸二乙酯 在 sodium hydroxide 、 丙酮 作用下， 生成 N-对硝基苯甲酰谷氨酸
  参考文献：
  名称：

  吐根糖浆中吐根生物碱头孢烯和依米丁在大鼠体内的生物转化。

  摘要：

  在大鼠中研究了吐根糖浆的主要活性成分头孢喹啉和依米丁的代谢。Cephaeline-6'-O-glucuronide 被发现是 cephaeline 的胆汁代谢物。观察到 Cephaeline (6'-O-demethylemetine) 和 9-O-demethylemetine 是 emetine 的酶水解胆汁代谢物。Cephaeline 与葡糖苷酸结合，而 emetine 去甲基化为 cephaeline 和 9-0-demethylemetine，之后可能与葡糖苷酸结合。在给予含有氚 (3H) 的吐根糖浆后 48 小时内，从大鼠身上收集尿液、粪便和胆汁——标记的头孢烯或依米丁。通过薄层色谱法 (TLC) 或高效液相色谱法 (HPLC) 分离和量化代谢物。3H-头孢烯的胆汁和尿排泄率为 57。分别为剂量的 5% 和 16.5%。Cephaeline-6'-O-glucuronide 占胆道放射性的

  DOI：

  10.1007/bf03190402
• 作为试剂：
  描述：

  异美沙酮 在 N-对硝基苯甲酰谷氨酸 作用下， 生成 (5S)-isomethadone
  参考文献：
  名称：

  Resolution of dl-Methadone and dl-Isomethadone

  摘要：

  DOI：

  10.1021/ja01176a514

文献信息

• Method for producing chiral mercapto amino acids
  申请人：Kotthaus Martina

  公开号：US20070112216A1

  公开（公告）日：2007-05-17

  The invention relates to a method for producing chiral mercapto amino acids of formula (I) wherein R 1 , R 2 and R 3 can represent hydrogen, C 6 -C 12 aryl, C 1 -C 6 -alkyl-C 6 -C 12 -aryl, C 6 -C 12 -aryl-C 1 -C 6 -alkyl, C 1 -C 18 -alkyl or C 2 -C 18 -alkenyl, R 2 and R 3 forming a saturated or unsaturated ring. According to said method, a) an oxo compound of formula (II), wherein X represents a leaving group, is reacted in the presence of ammonia or ammonium hydroxide and a sulfide, optionally under phase transfer catalysis or addition of a solubiliser, with a ketone or an aldehyde of formula (III) wherein R 4 and R 5 can represent a C 1 -C 12 alkyl radical or a C 6 -C 20 aryl radical or one of the two radicals H, or R 4 and R 5 together form a C 4 -C 7 ring, to form the compound of formula (IV), that b) reacts with HCN to form the corresponding nitrile, whereupon c) the crystallised nitrile is converted, by selective hydrolysis by means of a mineral acid, into the corresponding amide of formula (VI), and d) is then converted into the corresponding chiral amide of formula (VI*) by means of an L amidase or a chiral dissociating acid, whereupon by reaction with an acid, the desired chiral mercapto amino acid of formula (I) is obtained, or e) first the reaction with an acid is carried out, and then the conversion into the chiral mercapto amino acid takes place.

  该发明涉及一种生产手性巯基氨基酸的方法，其化学式为(I)，其中R1、R2和R3可以代表氢、C6-C12芳基、C1-C6烷基-C6-C12芳基、C6-C12芳基-C1-C6烷基、C1-C18烷基或C2-C18烯基，R2和R3形成饱和或不饱和环。根据该方法，a）在氨或氢氧化铵存在下，将具有化学式(II)的羰基化合物，其中X代表离去基团，与具有化学式(III)的酮或醛反应，其中R4和R5可以代表C1-C12烷基基团或C6-C20芳基基团或两个基团H中的一个，或者R4和R5一起形成C4-C7环，形成具有化学式(IV)的化合物，然后b）与HCN反应形成相应的腈，随后c）通过矿酸的选择性水解将结晶的腈转化为具有化学式(VI)的相应酰胺，并且d）通过L-酰胺酶或手性分离酸将其转化为具有化学式(VI*)的相应手性酰胺，然后通过与酸的反应得到所需的手性巯基氨基酸，或者e）首先进行与酸的反应，然后进行转化为手性巯基氨基酸。
• Non-Racemic Mixtures of Various Ratios of D- and L-methadone and Methods of Treating Pain Using the Same
  申请人：MIRONER Y. Eugene

  公开号：US20160235691A1

  公开（公告）日：2016-08-18

  Non-racemic mixtures of D- and L-methadone containing a ratio ranging from about 2.5:1 to about 3.5:1 by weight of D-methadone to L-methadone, such as for example about 2.9:1 to about 3.1:1 by weight of D-methadone to L-methadone, or about 3:1 by weight of D-methadone to L-methadone, have been found to exhibit surprising and unexpected beneficial results in the treatment of neuropathic pain. Additionally, non-racemic mixtures of D- and L-methadone containing a ratio ranging from about 2.5:1 to about 3.5:1 by weight of D-methadone to L-methadone, about 2.9:1 to about 3.1:1 by weight of D-methadone to L-methadone, or for example about 3:1 by weight of D-methadone to L-methadone, in combination with other non-methadone opioids have been found to exhibit surprising and unexpected beneficial results in the treatment of mixed pain.

  非外消旋混合物的D-和L-美沙酮，其含有D-美沙酮与L-美沙酮按重量比大约为2.5:1至大约3.5:1，例如大约为2.9:1至大约3.1:1，或者大约为3:1，已被发现在神经痛的治疗中表现出令人惊讶和意想不到的益处。此外，非外消旋混合物的D-和L-美沙酮，其含有D-美沙酮与L-美沙酮按重量比大约为2.5:1至大约3.5:1，大约为2.9:1至大约3.1:1，或者例如大约为3:1，与其他非美沙酮类阿片类药物结合使用，已被发现在混合性疼痛的治疗中表现出令人惊讶和意想不到的益处。
• Resolution of (±)-β-methylphenylethylamine by a novel chiral stationary phase for Pirkle-type column chromatography
  作者：Hayrullah Yilmaz、Giray Topal、Resit Cakmak、Halil Hosgoren

  DOI：10.1002/chir.20736

  日期：——

  study, a new Pirkle‐type chiral column stationary phase for resolution of β‐methylphenylethyl amine was described by using activated Sepharose 4B as a matrix, L‐tyrosine as a spacer arm, and an aromatic amine derivative of L‐glutamic acid as a ligand. The binding capacities of the stationary phase were determined at different pH values (pH = 6, 7, and 8) using buffer solutions as mobile phase, and enantiomeric

  在这项研究中，以活化的琼脂糖凝胶4B为基质，L酪氨酸为间隔臂，L谷氨酸的芳族胺衍生物为基质，描述了一种新的Pirkle型手性色谱柱固定相，用于拆分β-甲基苯基乙胺。配体。使用缓冲溶液作为流动相，在不同的pH值（pH = 6、7和8）下测定固定相的结合能力，并通过配备手性柱的HPLC测定对映体过量（ee）。发现ee为47％。《手性》，2010年。©2009 Wiley-Liss，Inc.。
• 一种N‐对氨基苯甲酰‐L‐谷氨酸的制备方法
  申请人：浙江汇能生物股份有限公司

  公开号：CN105439895B

  公开（公告）日：2018-02-27

  本发明提供了一种N‑对氨基苯甲酰‑L‑谷氨酸的制备方法，是以对硝基苯甲酸为原料、BTC/C2H4Cl2为酰氯化试剂、加入DMF作引发剂，于回流温度反应制得对硝基苯甲酰氯；所得对硝基苯甲酰氯与谷氨酸钠缩合，制得N‑对硝基苯甲酰‑L‑谷氨酸；所得N‑对硝基苯甲酰‑L‑谷氨酸以Pd‑C/HCO2NH4还原，制得N‑对氨基苯甲酰‑L‑谷氨酸。本发明所述制备方法反应条件温和，三废少，工艺简单，易于操作，得到的产品纯度高、收率高，适合工业化生产。
• N-对氨基苯甲酰-L-谷氨酸的制备方法
  申请人：江苏尚莱特医药化工材料有限公司

  公开号：CN108147977B

  公开（公告）日：2020-09-25

  本发明公开了一种N‑对氨基苯甲酰‑L‑谷氨酸的制备方法，具有以下步骤：①以对硝基苯甲酸为起始原料，以草酰氯为酰氯化试剂，以四氢呋喃与DMF为混合溶剂，经酰氯化反应制得对硝基苯甲酰氯；②由步骤①制得的对硝基苯甲酰氯与谷氨酸钠经缩合反应制得N‑对硝基苯甲酰‑L‑谷氨酸；③以水合肼为还原剂，以六水合三氯化铁为催化剂，由步骤②制得的N‑对硝基苯甲酰‑L‑谷氨酸经还原反应制得N‑对氨基苯甲酰‑L‑谷氨酸。本发明的酰氯化反应选择在四氢呋喃和DMF混合溶剂中以草酰氯作为酰氯化试剂，还原反应选择水合肼为还原剂且以六水合三氯化铁为催化剂，最终能够得到纯度≥99.9%的N‑对氨基苯甲酰‑L‑谷氨酸。