乳清酸甲酯 | 6153-44-2

• 物质功能分类: 化学试剂 - 有机试剂 - 酯类
• 分子结构分类: 有机化合物 - 有机杂环化合物 - 二嗪类
• 中文名称: 乳清酸甲酯
• 中文别名: 甲基乳清酸；2,6-二氧代-1,2,3,6-四氢嘧啶-4-甲酸甲酯
• 英文名称: methyl orotate
• 英文别名: orotic acid methyl ester；Methyl-orotat；6-carbomethoxy-uracil；methyl 2,4-dioxo-1H-pyrimidine-6-carboxylate
• CAS: 6153-44-2
• 化学式: C₆H₆N₂O₄
• mdl: MFCD00010564
• 分子量: 170.125
• InChiKey: UUTDWTOZAWFKFW-UHFFFAOYSA-N

物化性质

• 熔点：
  244 °C
• 沸点：
  299.73°C (rough estimate)
• 密度：
  1.5523 (rough estimate)
• 稳定性/保质期：

  在常温常压下保持稳定，应避免与不相容的材料接触。

计算性质

• 辛醇/水分配系数(LogP)：
  -0.9
• 重原子数：
  12
• 可旋转键数：
  2
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.17
• 拓扑面积：
  84.5
• 氢给体数：
  2
• 氢受体数：
  4

安全信息

• 危险品标志：
  Xi
• 安全说明：
  S26,S37,S39
• 危险类别码：
  R36/37/38
• 海关编码：
  2933599090
• 危险性防范说明：
  P261,P305+P351+P338
• 危险性描述：
  H315,H319,H335
• 储存条件：
  密封储存，应存放在阴凉、干燥的仓库中。

SDS

Name:	Methyl orotate 99% Material Safety Data Sheet
Synonym:	Orotic acid methyl ester; Methyl 1,2,3,6-tetrahydro-2,6-dioxopyrimidine-4-carboxylat
CAS:	6153-44-2

Section 1 - Chemical Product MSDS Name:Methyl orotate 99% Material Safety Data Sheet
Synonym:Orotic acid methyl ester; Methyl 1,2,3,6-tetrahydro-2,6-dioxopyrimidine-4-carboxylat

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Section 2 - COMPOSITION, INFORMATION ON INGREDIENTS

CAS#	Chemical Name	content	EINECS#
6153-44-2	Methyl orotate	99	228-171-9

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: Immediately 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.
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:
Sweep up, then place into a suitable 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. 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# 6153-44-2: 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: yellow
Odor: None reported.
pH: Not available.
Vapor Pressure: Not available.
Viscosity: Not available.
Boiling Point: Not available.
Freezing/Melting Point: 244 deg C
Autoignition Temperature: Not applicable.
Flash Point: Not applicable.
Explosion Limits, lower: Not available.
Explosion Limits, upper: Not available.
Decomposition Temperature: > 244 deg C
Solubility in water: Not available.
Specific Gravity/Density: Not available.
Molecular Formula: C6H6N2O4
Molecular Weight: 170.12

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Section 10 - STABILITY AND REACTIVITY
Chemical Stability:
Stable under normal temperatures and pressures.
Conditions to Avoid:
Incompatible materials, strong oxidants.
Incompatibilities with Other Materials:
Oxidizing agents.
Hazardous Decomposition Products:
Nitrogen oxides, carbon monoxide, irritating and toxic fumes and gases, carbon dioxide, nitrogen.
Hazardous Polymerization: Will not occur.

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Section 11 - TOXICOLOGICAL INFORMATION
RTECS#:
CAS# 6153-44-2 unlisted.
LD50/LC50:
Not available.
Carcinogenicity:
Methyl orotate - 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.
WGK (Water Danger/Protection)
CAS# 6153-44-2: No information available.
Canada
None of the chemicals in this product are listed on the DSL/NDSL list.
CAS# 6153-44-2 is not listed on Canada's Ingredient Disclosure List.
US FEDERAL
TSCA
CAS# 6153-44-2 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

乳清酸甲酯主要用于合成用于肽识别的嘧啶联氨酸，同时也用于制备含有无环部分的嘧啶。

反应信息

• 作为反应物：
  描述：

  乳清酸甲酯 在 硫酸 、 硝酸 、 sodium hydride 、 溶剂黄146 、 锌 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 生成
  参考文献：
  名称：

  Efficient and regioselective synthesis of pyrimido[5,4-d]pyrimidine-2,4,6,8(1H,3H,5H,7H)-tetraones with diversified substitutions

  摘要：

  A highly regioselective synthesis of N3-, N5-, and N7-substituted pyrimidopyrimidinetetraones is reported. The synthesis of N5-monosubstituted and N5-, N7-disubstituted compounds was achieved through selective alkylation and urea mediated pyrimidinedione formation reactions. For the more synthetically challenging N3-, N5-, and N7-trisubstituted structures, in combination with computational studies, a palladium catalyzed cascade reaction was successfully employed for the simultaneous formation of the pyrimidinedione ring and functionalization of the N3 position, which provided the trisubstituted products in high yields with full control of regioselectivity. By applying this methodology, key intermediate 26 was prepared in a few synthetic steps in good overall yield for further functionalization and quick SAR development. (C) 2012 Published by Elsevier Ltd.

  DOI：

  10.1016/j.tetlet.2012.10.109
• 作为产物：
  描述：

  乳清酸 在 氯化亚砜 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 生成 乳清酸甲酯
  参考文献：
  名称：

  Synthesis of Substituted Pyrimidine Hydrazine Acids (PHA) and Their Use in Peptide Recognition

  摘要：

  DOI：

  10.3987/com-05-s(t)6

文献信息

• The [2+2] Photocycloaddition of Uracil Derivatives with Ethylene as a General Route to <i>cis</i>-Cyclobutane β-Amino Acids
  作者：David Aitken、Christine Gauzy、Bertrand Saby、Elisabeth Pereira、Sophie Faure

  DOI：10.1055/s-2006-941571

  日期：2006.6

  A three-step procedure, based on the [2+2]-photochemical reaction of uracils with ethylene followed by controlled degradation of the heterocyclic ring, has been developed for the synthesis of a range of C1- and C2-substituted cis-cyclobutane β-amino acids, in good overall yield.

  基于尿嘧啶与乙烯的[2+2]光化学反应，随后通过控制杂环的降解，已开发出一种三步法程序，用于合成一系列C1和C2取代的顺式环丁烷β-氨基酸，总体产率良好。
• Synthesis of New Polyamine Derivatives for Cancer Chemotherapeutic Studies
  作者：Louis T. Weinstock、William J. Rost、C.C. Cheng

  DOI：10.1002/jps.2600700835

  日期：1981.8

  Selected homologs, analogs, and acylated derivatives of spermine and spermidine, together with several heterocyclic and aromatic compounds containing a novoldiamine side chain, were prepared and evaluated biologically. Several compounds possessed activity against B-16 melanoma and human epidermoid carcinoma of the nasopharynx.

  制备了精胺和亚精胺的选定同系物，类似物和酰化衍生物，以及几种含有酚醛二胺侧链的杂环和芳族化合物，并进行了生物学评估。几种化合物具有对抗B-16黑色素瘤和人鼻咽表皮样癌的活性。
• [EN] PYRIMIDINE DERIVATIVES AND THEIR USE AS HERBICIDES<br/>[FR] DÉRIVÉS DE PYRIMIDINE ET LEUR UTILISATION EN TANT QU'HERBICIDES
  申请人：SYNGENTA LTD

  公开号：WO2010092339A1

  公开（公告）日：2010-08-19

  The present invention relates to substituted pyrimidine derivatives, as well as N- oxides thereof and agriculturally acceptable salts thereof, and their use to control undesired plant growth, in particular in crops of useful plants. The invention extends to herbicidal compositions comprising such compounds, N-oxides and/or salts as well as mixtures of the same with one or more further active ingredient (such as, for example, an herbicide, fungicide, insecticide and/or plant growth regulator) and/or a safener. The invention further relates to intermediates useful in the preparation of such compounds, and to processes for their preparation.

  本发明涉及取代嘧啶衍生物，以及其N-氧化物和农业上可接受的盐，以及它们在控制不受欢迎的植物生长方面的用途，特别是在有用植物的作物中。该发明涉及包括这些化合物、N-氧化物和/或盐以及与一种或多种进一步活性成分（例如除草剂、杀菌剂、杀虫剂和/或植物生长调节剂）和/或安全剂的混合物在内的除草剂组合物。该发明还涉及在制备这些化合物中有用的中间体，以及它们的制备方法。
• 一种5-三氟甲基尿嘧啶的合成方法
  申请人：遵义医科大学

  公开号：CN108484508B

  公开（公告）日：2019-07-23

  本申请公开了一种简便条件下制备一种5‑三氟甲基尿嘧啶的合成方法，该方法由尿嘧啶和三氟碘甲烷出发，加入碱后，在可见光照射下，高效率地得到5‑三氟甲基尿嘧啶的结构。得到的部分产物是上市的药物分子或者重要的药物中间体。该方法使用廉价易得的尿嘧啶和三氟碘甲烷为原料，反应过程中仅仅需要光照以及加入廉价的碱而无需使用催化剂，大量生产时，溶剂可以通过减压蒸馏的方法回收。整个生产过程绿色、经济、高效，和以往的生产工艺相比，具有十分显著的优势。
• 2-SUBSTITUTED-6-AMINO-5-ALKYL, ALKENYL OR ALKYNYL-4-PYRIMIDINECARBOXYLIC ACIDS AND 6-SUBSTITUTED-4-AMINO-3- ALKYL, ALKENYL OR ALKYNYL PICOLINIC ACIDS AND THEIR USE AS HERBICIDES
  申请人：Epp Jeffrey B.

  公开号：US20090088322A1

  公开（公告）日：2009-04-02

  6-Amino-4-pyrimidinecarboxylic acids having alkyl, alkenyl or alkynyl substituents in the 5-position and 4-aminopicolinic acids having alkyl, alkenyl or alkynyl substituents in the 3-position, and their amine and acid derivatives, are potent herbicides demonstrating a broad spectrum of weed control.

  在5位上具有烷基、烯基或炔基取代基的6-氨基-4-嘧啶羧酸，以及在3位上具有烷基、烯基或炔基取代基的4-氨基吡啶羧酸，以及它们的胺和酸衍生物，是表现出广谱除草作用的有效除草剂。

表征谱图