中草酸 | 473-90-5

• 物质功能分类: 有机原料 - 羧酸类化合物及衍生物
• 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: 中草酸
• 中文别名: 氧代丙二酸；羰基丙二酸
• 英文名称: Ketomalonic acid
• 英文别名: Mesoxalic acid；2-oxopropanedioic acid
• CAS: 473-90-5
• 化学式: C₃H₂O₅
• mdl: MFCD00002578
• 分子量: 118.046
• InChiKey: XEEVLJKYYUVTRC-UHFFFAOYSA-N

物化性质

• 熔点：
  178 °C
• 沸点：
  405.2±28.0 °C(Predicted)
• 密度：
  1.832

计算性质

• 辛醇/水分配系数(LogP)：
  0.7
• 重原子数：
  8
• 可旋转键数：
  2
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  91.7
• 氢给体数：
  2
• 氢受体数：
  5

安全信息

• 海关编码：
  2918300090

SDS

Name:	Ketomalonic Acid Monohydrate 99% Material Safety Data Sheet
Synonym:	Mesoxalate, Oxomalonic Acid
CAS:	473-90-5

Section 1 - Chemical Product MSDS Name:Ketomalonic Acid Monohydrate 99% Material Safety Data Sheet
Synonym:Mesoxalate, Oxomalonic Acid

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Section 2 - COMPOSITION, INFORMATION ON INGREDIENTS

CAS#	Chemical Name	content	EINECS#
473-90-5	Ketomalonic Acid Monohydrate	99	207-473-4

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. The toxicological properties of this material have not been fully investigated.
Skin:
May cause skin irritation. The toxicological properties of this material have not been fully investigated.
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.
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:
Never give anything by mouth to an unconscious person. Get medical aid. Do NOT induce vomiting. If conscious and alert, rinse mouth and drink 2-4 cupfuls of milk or water.
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:

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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. Dusts may be combustible when exposed to heat, flame, or oxidizing agents.
Extinguishing Media:
Use agent most appropriate to extinguish fire. 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:
Vacuum or sweep up material and place into a suitable disposal container. Clean up spills immediately, observing precautions in the Protective Equipment section. Avoid generating dusty conditions.
Remove all sources of ignition. 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:
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# 473-90-5: 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: Crystals
Color: white to pale yellow
Odor: Not available.
pH: Not available.
Vapor Pressure: Not available.
Viscosity: Not available.
Boiling Point: Decomposes
Freezing/Melting Point: 121 deg C
Autoignition Temperature: Not available.
Flash Point: 121 deg C ( 249.80 deg F)
Explosion Limits, lower: Not available.
Explosion Limits, upper: Not available.
Decomposition Temperature: 121 deg C
Solubility in water: soluble in alcohol and ether
Specific Gravity/Density:
Molecular Formula: C3H4O6
Molecular Weight: 136.06

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

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Section 11 - TOXICOLOGICAL INFORMATION
RTECS#:
CAS# 473-90-5: OX7480000 LD50/LC50:
CAS# 473-90-5: Oral, mouse: LD50 = 5 gm/kg.
Carcinogenicity:
Ketomalonic Acid Monohydrate - Not listed by ACGIH, IARC, or NTP.
Other:
See actual entry in RTECS for complete information.

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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# 473-90-5: No information available.
Canada
None of the chemicals in this product are listed on the DSL/NDSL list.
CAS# 473-90-5 is not listed on Canada's Ingredient Disclosure List.
US FEDERAL
TSCA
CAS# 473-90-5 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

mesoxalate（酮基琥珀酸）是一种二羧酸兼酮酸，能够阻断HIV-1反转录酶，其IC50值为2.2μM。

反应信息

• 作为反应物：
  描述：

  中草酸 在 iron sulfide 、 碳酸氢铵 作用下， 以 水 为溶剂， 反应 144.0h， 以86%的产率得到聚甘氨酸
  参考文献：
  名称：

  Primordial Amino Acids by Reductive Amination of α-Oxo Acids in Conjunction with the Oxidative Formation of Pyrite

  摘要：

  DOI：

  10.1016/00404-0399(50)10086-
• 作为产物：
  描述：

  三醋精 在 硝酸 作用下， 生成 中草酸
  参考文献：
  名称：

  Seelig, Chemische Berichte, 1891, vol. 24, p. 3466

  摘要：

  DOI：

文献信息

• Effects of Gln102Arg and Cys97Gly mutations on the structural specificity and stereospecificity of the L-lactate dehydrogenase from Bacillus stearothermophilus
  作者：Helmut K. W. Kallwass、Marcel A. Luyten、Wendy Parris、Marvin Gold、Cyril M. Kay、J. Bryan Jones

  DOI：10.1021/ja00038a016

  日期：1992.6

  The L-lactate dehydrogenase of Bacillus stearothermophilus (BSLDH) is a thermostable enzyme with considerable potential for applications in asymmetric synthesis. An understanding of the factors controlling its structural specificity and stereospecificity is therefore of interest. In this paper the effects of GIn 102→Arg and Cys97→Gly mutations have been evaluated. In a survey of thirteen 2-keto acids

  嗜热脂肪芽孢杆菌 (BSLDH) 的 L-乳酸脱氢酶是一种热稳定酶，在不对称合成中具有相当大的应用潜力。因此，了解控制其结构特异性和立体特异性的因素是很有意义的。本文评估了 GIn 102→Arg 和 Cys97→Gly 突变的影响。在对 13 种 2-酮酸的调查中，发现 Q102R 突变降低了 BSLDH 还原具有小或亲水 R 基团的 RCOCOOH 底物的活性，而不影响其对具有较大疏水性 R 取代基的那些的活性
• Chemoselective and Highly Sensitive Quantification of Gut Microbiome and Human Metabolites
  作者：Weifeng Lin、Louis P. Conway、Miroslav Vujasinovic、J.‐Matthias Löhr、Daniel Globisch

  DOI：10.1002/anie.202107101

  日期：2021.10.18

  The microbiome has a fundamental impact on the human host's physiology through the production of highly reactive compounds that can lead to disease development. One class of such compounds are carbonyl-containing metabolites, which are involved in diverse biochemical processes. Mass spectrometry is the method of choice for analysis of metabolites but carbonyls are analytically challenging. Herein,

  微生物组通过产生可导致疾病发展的高活性化合物，对人类宿主的生理机能产生根本性影响。一类此类化合物是含羰基的代谢物，它们参与多种生化过程。质谱法是分析代谢物的首选方法，但羰基化合物在分析上具有挑战性。在这里，我们开发了一种新的化学生物学工具，利用化学选择性修饰来克服分析限制。两种同位素探针可实现飞摩尔水平的同步半定量分析以及阿托摩尔数量的定性分析，从而检测人类粪便、尿液和血浆样本中的 200 多种代谢物。这种全面的质谱分析扩大了代谢组学驱动的生物标志物发现的范围。我们预计我们的化学生物学工具将广泛用于代谢组学分析，以便更好地了解微生物与人类宿主的相互作用和疾病的发展。
• Tropane derivatives useful in therapy
  申请人：Pfizer Inc.

  公开号：US20040014742A1

  公开（公告）日：2004-01-22

  The present invention provides compounds of formula (I) 1 wherein X, Y, R 1 , R 2 and R 3 are as defined hereinabove. The compounds of the present invention are modulators, especially antagonists, of the activity of chemokine CCR5 receptors. Modulators of the CCR5 receptor may be useful in the treatment of various inflammatory diseases and conditions, and in the treatment of infection by HIV and genetically related retroviruses.

  本发明提供了式(I)中的化合物，其中X、Y、R1、R2和R3如上文所定义。本发明的化合物是化学趋化因子CCR5受体的调节剂，特别是拮抗剂。CCR5受体的调节剂可能在治疗各种炎症性疾病和症状以及治疗HIV和遗传相关逆转录病毒感染方面有用。
• X=Y-ZH systems as potential 1,3-dipoles
  作者：Moustafa F. Aly、Ronald Grigg

  DOI：10.1016/s0040-4020(01)86099-3

  日期：1988.1

  α-Imino acids, prepared from α-keto acids and primary amines, undergo facile decarboxylation to the corresponding imines on heating at ⩽,80°C in benzene or methylene chloride. Decarboxylation proceeds via a 1,2-ylide which can be trapped by sulphur to give the corresponding secondary thioamides in good yield. 1,2-Ylides from secondary amines and ∞-keto acids can be generated in situ and trapped with

  由α-酮酸和伯胺制得的α-氨基酸在⩽80℃下于苯或二氯甲烷中加热时，容易脱羧成相应的亚胺。脱羧反应通过1,2-ylide进行，可以被硫捕获，从而以高收率得到相应的仲硫代酰胺。来自仲胺和∞-酮酸的1,2-内酯可以原位生成并用硫捕获，从而以优异的收率得到叔硫酰胺。
• Novel Benzodiazepine Photoaffinity Probe Stereoselectively Labels a Site Deep within the Membrane-Spanning Domain of the Cholecystokinin Receptor
  作者：Elizabeth M. Hadac、Eric S. Dawson、James W. Darrow、Elizabeth E. Sugg、Terry P. Lybrand、Laurence J. Miller

  DOI：10.1021/jm049072h

  日期：2006.2.1

  representing both antagonist and agonist ligands of the type A cholecystokinin receptor. The parent compounds of the 1,5-benzodiazepine CCK receptor photoaffinity ligands were originally prepared in an effort to develop orally active drugs. The enantiomeric compounds reported in this study selectively photoaffinity-labeled the CCK receptor, resulting in the identification of a site of attachment for the photolabile

  对药物作用的分子基础的理解为改善药物性质和开发作用于相同生物学靶标的更有效和选择性的分子提供了机会。在这项工作中，我们已经确定了结构相关的1,5-苯并二氮杂二苯甲酮衍生物的外消旋混合物中的活性对映体，它们代表A型胆囊收缩素受体的拮抗剂和激动剂配体。1,5-苯并二氮杂pineCCK受体光亲和配体的母体化合物最初是为了开发口服活性药物而制备的。这项研究中报道的对映体化合物选择性地用光亲和标记了CCK受体，从而确定了受体探针深处的拮抗剂探针的光不稳定部分的附着位点。在Leu（88）的跨膜区域，这是跨膜片段2内的残基。相反，激动剂探针标记包括细胞外环一和跨膜片段三的一部分的区域。拮抗剂与受体的共价连接位点在构建拮抗剂-受体复合物的理论三维分子模型中起指导作用。这些模型提供了一种手段，可以在所有当前可利用的生物学数据的背景下可视化物理上合理的配体-受体相互作用，该生物学数据解决了与CCK受体的小分子