1,3-二甲基尿酸 | 944-73-0

• 物质功能分类: 生物化工 - 核苷类药物 - 核苷酸及其类似物
• 分子结构分类: 有机化合物 - 有机杂环化合物 - 咪唑并嘧啶类
• 中文名称: 1,3-二甲基尿酸
• 中文别名: 1,3-二甲基-2,6,8-三羟基嘌呤
• 英文名称: 1,3-dimethyluric acid
• 英文别名: 1,3-Dimethyl-harnsaeure；1,3-DMU；1,3-dimethyl-7,9-dihydropurine-2,6,8-trione
• CAS: 944-73-0
• 化学式: C₇H₈N₄O₃
• 分子量: 196.166
• InChiKey: OTSBKHHWSQYEHK-UHFFFAOYSA-N

物化性质

• 熔点：
  ≥300 °C(lit.)
• 沸点：
  333.04°C (rough estimate)
• 密度：
  1.4375 (rough estimate)
• 溶解度：
  可溶于1MNH4OH：溶解度为50mg/mL，透明至轻微混浊，无色至淡黄色
• 物理描述：
  Solid
• 碰撞截面：
  142.5 Ų [M+H]+ [CCS Type: DT, Method: single field calibrated with Agilent tune mix (Agilent)]
• 保留指数：
  2052
• 稳定性/保质期：

  在常温常压下保持稳定，应避免与氧化物直接接触。

计算性质

• 辛醇/水分配系数(LogP)：
  -0.5
• 重原子数：
  14
• 可旋转键数：
  0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.29
• 拓扑面积：
  81.8
• 氢给体数：
  2
• 氢受体数：
  3

ADMET

代谢

1,3-二甲基尿嘧啶酸是茶碱的人类已知代谢物。

1,3-Dimethyluric acid is a known human metabolite of theophylline.

来源:NORMAN Suspect List Exchange

安全信息

• 安全说明：
  S24/25
• WGK Germany：
  2
• 海关编码：
  2933990090
• 危险性防范说明：
  P261,P305+P351+P338
• 危险性描述：
  H302,H315,H319,H335
• 储存条件：
  请将容器密封保存，并存放在阴凉、干燥处。

SDS

Name:	1 3-Dimethyluric acid 99% Material Safety Data Sheet
Synonym:	7,9-Dihydro-1,3-dimenthyl-1H-purine-2,6,8(3H)-trione; Oxytheophylline; Urinc acid, 1,3-dimethyl
CAS:	944-73-0

Section 1 - Chemical Product MSDS Name:1 3-Dimethyluric acid 99% Material Safety Data Sheet
Synonym:7,9-Dihydro-1,3-dimenthyl-1H-purine-2,6,8(3H)-trione; Oxytheophylline; Urinc acid, 1,3-dimethyl

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Section 2 - COMPOSITION, INFORMATION ON INGREDIENTS

CAS#	Chemical Name	content	EINECS#
944-73-0	1,3-dimethyluric acid	99	213-410-1

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:

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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 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:
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:
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:
Facilities storing or utilizing this material should be equipped with an eyewash facility and a safety shower. Use adequate ventilation to keep airborne concentrations low.
Exposure Limits CAS# 944-73-0: 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:
A respiratory protection program that meets OSHA's 29 CFR 1910.134 and ANSI Z88.2 requirements or European Standard EN 149 must be followed whenever workplace conditions warrant respirator use.

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Section 9 - PHYSICAL AND CHEMICAL PROPERTIES

Physical State: Powder
Color: white
Odor: Not available.
pH: Not available.
Vapor Pressure: Not available.
Viscosity: Not available.
Boiling Point: Not available.
Freezing/Melting Point: 412.00 - 415.00 deg C
Autoignition Temperature: Not available.
Flash Point: Not available.
Explosion Limits, lower: Not available.
Explosion Limits, upper: Not available.
Decomposition Temperature:
Solubility in water:
Specific Gravity/Density:
Molecular Formula: C7H8N4O3
Molecular Weight: 196.17

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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:
Nitrogen oxides, carbon monoxide, carbon dioxide.
Hazardous Polymerization: Has not been reported

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Section 11 - TOXICOLOGICAL INFORMATION
RTECS#:
CAS# 944-73-0: UP0783700 LD50/LC50:
CAS# 944-73-0: Oral, mouse: LD50 = >2 gm/kg; Oral, rat: LD50 = >2 gm/kg.
Carcinogenicity:
1,3-dimethyluric acid - 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# 944-73-0: No information available.
Canada
None of the chemicals in this product are listed on the DSL/NDSL list.
CAS# 944-73-0 is not listed on Canada's Ingredient Disclosure List.
US FEDERAL
TSCA
CAS# 944-73-0 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

生物活性

1,3-二甲基尿酸是人体茶碱代谢的产物，也是尿路结石中的一种嘌呤成分。

人类内源性代谢物

反应信息

• 作为反应物：
  描述：

  1,3-二甲基尿酸 在 potassium permanganate 作用下， 生成 N,N′-二甲基草酰胺
  参考文献：
  名称：

  Biltz; Schauder, Journal fur praktische Chemie (Leipzig 1954), 1923, vol. <2>106, p. 115,136

  摘要：

  DOI：
• 作为产物：
  描述：

  在 水 、 sodium methylate 作用下， 以79.9%的产率得到1,3-二甲基尿酸
  参考文献：
  名称：

  一种1,3-二甲基尿酸的合成方法

  摘要：

  本发明公开了一种1,3‑二甲基尿酸的合成方法，以1,3‑二甲基‑5,6‑二氨基脲嘧啶为原料，先由1,3‑二甲基‑5,6‑二氨基脲嘧啶在缚酸剂的作用下，与酰化试剂进行酰化反应得到中间体1,3‑二甲基‑5‑氨基‑6‑N‑烷氧羰基脲嘧啶；再由中间体1,3‑二甲基‑5‑氨基‑6‑N‑烷氧羰基脲嘧啶在碱的作用下环合反应得到1,3‑二甲基尿酸；所述的酰化反应和环合反应均在溶剂作用下进行。本发明经优化设计和试验研究，采用二步法合成1,3‑二甲基尿酸，工艺流程合理可行，反应温度始适中可控，且收率高，适合大规模工业化生产。

  公开号：

  CN110204547A

文献信息

• 一种1,3,7,9-四甲基尿酸的全合成方法
  申请人：上海佰特因医药科技有限公司

  公开号：CN106046004B

  公开（公告）日：2018-05-15

  本发明涉及一种1,3,7,9‑四甲基尿酸的全合成方法，包括以6‑氨基‑1,3‑二甲基尿嘧啶为原料，经过亚硝基化反应得到中间体6‑氨基‑1,3‑二甲基‑5‑亚硝基尿嘧啶；6‑氨基‑1,3‑二甲基‑5‑亚硝基尿嘧啶经还原反应得到中间体1,3‑二甲基‑5，6‑二氨基尿嘧啶；1,3‑二甲基‑5，6‑二氨基尿嘧啶进行环合反应生成中间体1,3‑二甲基尿酸；1,3‑二甲基尿酸和甲基化试剂进行反应得到产物。采用本发明方法来制备四甲基尿酸，可在工业应用上大量合成，不受原料对其的约束；转化率高，产率高，合成方便，后处理较简单，适合大规模生产，能够广泛的推广应用；无须在高压条件下进行，对设备要求低，同时减少了危险的发生率；利用重结晶放置制备目标产物，产物纯度高。
• Extraction of Radio-Labelled Xanthine Derivatives by Artificial Receptors: Deep Insight into the Association Behaviour
  作者：Martin Bomkamp、Carsten Siering、Karin Landrock、Holger Stephan、Roland Fröhlich、Siegfried R. Waldvogel

  DOI：10.1002/chem.200601231

  日期：2007.4.27

  Association constants for the interaction of almost insoluble substrates with triphenylene ketal-based receptors in toluene have been determined by means of an extraction method employing the corresponding radio-labelled substrates. Flexible and more polar receptors tend to aggregate and exhibit inferior extraction qualities. Binding constants in toluene were found to be in the range 10(5)-10(7) m(-1)

  已经通过采用相应的放射性标记的底物的提取方法确定了几乎不溶的底物与甲苯中基于三亚苯基缩酮的受体相互作用的缔合常数。柔性且极性更大的受体往往会聚集并表现出较差的提取质量。发现在甲苯中的结合常数在10（5）-10（7）m（-1）的范围内，这明显高于在二氯甲烷中的结合常数。X射线分析表明水分子直接参与了结合过程，这可能解释了溶剂中水分对复合物稳定性的出乎意料的小影响。
• Reaction of 5-Nitroso-6-Aminouracils with Glyoxylic Acid – A Simple Synthetic Pathway to Uric Acid Derivatives
  作者：Yu. A. Azev、O. S. Ermakova、V. S. Berseneva

  DOI：10.1007/s10600-017-2065-5

  日期：2017.5

  on cyclization of 4,5-aminopyrimidines with urea, formamide, or formic acid [1]. The reaction of 4,5-aminopyrimidines with C2 cyclizing agents (glyoxal, glyoxylic acid derivatives, etc.) synthesized pteridine derivatives [1, 2]. Heating 5-nitroso-6-aminouracils with aldehydes formed 7-hydroxyxanthine derivatives [3]. Uric acid is the final product from oxidation (metabolism) of purines in living organisms

  嘌呤通常通过 Traube 提出的方法合成，该方法基于 4,5-氨基嘧啶与尿素、甲酰胺或甲酸的环化 [1]。4,5-氨基嘧啶与C2环化剂（乙二醛、乙醛酸衍生物等）反应合成蝶啶衍生物[1, 2]。加热 5-亚硝基-6-氨基尿嘧啶与醛形成 7-羟基黄嘌呤衍生物 [3]。尿酸是生物体内嘌呤氧化（代谢）的最终产物。它的水平表征了代谢状况。如果其体内含量增加，则会出现严重的疾病。因此，监测尿酸及其衍生物的分泌水平尤为重要[4]。实际上，可以从尿酸合成整套天然嘌呤碱基或整合到结构中或由嘌呤代谢产生的核酸 [1]。研究了尿嘧啶胺衍生物与 C2 环化剂的反应，以开发简单方便的嘌呤和蝶啶衍生物合成途径。在工作期间发现了在与乙醛酸反应期间 5-亚硝基-6-氨基尿嘧啶 1a 和 1b 的不寻常转化。因此，在甲酸中短暂加热 1a 和 1b 以及乙醛酸可以顺利形成高产率的尿酸衍生物 2a 和 2b（方案 1）。在工作期间发现了在与乙醛酸反应期间
• Conformational and stereoelectronic control in ring-transformations of<i>cis</i>-4,5-dialkoxytetrahydropurine-2,6,8-triones
  作者：Nevenka Poje、Antun Palković、Mirko Poje

  DOI：10.1002/jhet.5570340220

  日期：1997.3

  transamidation 5 → 4 presumably occurs via a bicyclic acid aminal type intermediate 3, heretofore misassigned as the reaction product. A curious base-catalysed rearrangement was encountered with the 5 (R1 = R3 = Me, R7 = H) cases, which afforded 5-methoxy-1,5-bis(methylaminocarbonyl)hydantoins 7. Remarkable stability of the conformationally rigid propellane type 4,5-ethylenedioxytetrahydropurine-2,6,8-triones

  在位置4的4,5-二甲氧基四氢嘌呤-2,6,8-三酮2的发散酸催化的开环，生成1-（5-甲氧基乙内酰脲-5羰基）脲4（R 7 = Me）或5-甲氧基-5-ureido-2,4,6-嘧啶三酮5（R 7 = H）可以通过假设其优先选择与N-取代作用相关的顺式融合系统的两个构象异构体之一来合理化。分子内酰胺基转移5 → 4大概是通过双环酸氨基型中间体3发生的，迄今被误分配为反应产物。与5（R 1 = R 3 = Me，R 7 = H）的情况下遇到一个好奇的碱催化重排，提供了5-甲氧基-1,5-双（甲基氨基羰基）乙内酰脲7。构象刚性的4,5-亚乙基二氧基四氢嘌呤-2,6,8-三酮9型构型的螺旋桨的显着稳定性表明，位置4处的开环方式受强大的立体电子因子控制。但是，在加热9a（R 7 = H）的水溶液时，在1,6-键上出现了另一种开环。随后发生的脱羧重排导致1,3-二甲基丙氨酸（12）及其前体1-（2-羟基乙氧基）-2
• Synthesis and structure of dehydro-4-iminoallantoin and its covalent adducts
  作者：T. Popović、Lea Sokolić、Nevenka Modrić、A. Palković、M. Poje

  DOI：10.1016/s0040-4020(01)80927-3

  日期：1991.1

  (6) arose on exposure of the primary adduct 4 to dilute acetic acid; a direct route to 6 was provided by oxidation of 1-iminoallantoin (2) with iodine. Both dehydro-allantoin (8) and its 4-imino analogue 6 form covalent adducts (e.g. with MeOH) at the 5-position. A brief rationale which focusses upon the stepwise nature and regiochemical course of the reaction is presented.

  显示两个连续的Denicke反应产物的表示是不正确的。铁氰化物在氨水中氧化尿酸（1a）得到5-氨基-4-亚氨基丙氨酸（4）和1,5-二氨基-3,7-二氧代-2,4,6,8-四氮杂双环[3.3.0]辛烷（5a），而甲基化尿酸1b-g仅提供相应的终产物5。当初级加合物4暴露于稀乙酸中时，产生关键的脱氢-4-亚氨基丙氨酸（6）。通过用碘氧化1-亚氨基丙氨酸（2）提供了一条通往6的直接途径。脱氢丙氨酸（8）及其4-亚氨基类似物6在5位形成共价加合物（例如与MeOH）。简要介绍了反应的逐步性质和区域化学过程的基本原理。

表征谱图