丙二酸二乙酯-2-13C | 67035-94-3

• 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: 丙二酸二乙酯-2-13C
• 英文名称: diethyl [2-¹³C]malonate
• 英文别名: diethyl malonate-2-¹³C；Diethyl malonate-2-13C；diethyl (213C)propanedioate
• CAS: 67035-94-3
• 化学式: C₇H₁₂O₄
• 分子量: 161.159
• InChiKey: IYXGSMUGOJNHAZ-HOSYLAQJSA-N

物化性质

• 熔点：
  -51--50 °C (lit.)
• 沸点：
  199 °C (lit.)
• 密度：
  1.054 g/mL at 25 °C
• 蒸气密度：
  5.52 (vs air)
• 闪点：
  212 °F
• 溶解度：
  可溶于氯仿、乙酸乙酯（少量）
• 稳定性/保质期：
  遵照规定使用和储存，则不会发生分解。

计算性质

• 辛醇/水分配系数(LogP)：
  1
• 重原子数：
  11
• 可旋转键数：
  6
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.714
• 拓扑面积：
  52.6
• 氢给体数：
  0
• 氢受体数：
  4

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
• 危险品运输编号：
  UN 3464

SDS

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Section 1. IDENTIFICATION OF THE SUBSTANCE/MIXTURE
Product identifiers
Product name : Diethyl malonate-2-13C
CAS-No. : 67035-94-3

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Section 2. HAZARDS IDENTIFICATION
Classification of the substance or mixture
Classification according to Regulation (EC) No 1272/2008 [EU-GHS/CLP]
Skin irritation (Category 2)
Eye irritation (Category 2)
Specific target organ toxicity - single exposure (Category 3)
Classification according to EU Directives 67/548/EEC or 1999/45/EC
Irritating to eyes, respiratory system and skin.
Label elements
Labelling according Regulation (EC) No 1272/2008 [CLP]
Pictogram
Signal word Warning
Hazard statement(s)
Causes skin irritation.
Causes serious eye irritation.
May cause respiratory irritation.
Precautionary statement(s)
Avoid breathing dust/ fume/ gas/ mist/ vapours/ spray.
P305 + P351 + P338 IF IN EYES: Rinse cautiously with water for several minutes. Remove
contact lenses, if present and easy to do. Continue rinsing.
Supplemental Hazard none
Statements
According to European Directive 67/548/EEC as amended.
Hazard symbol(s)
R-phrase(s)
R36/37/38 Irritating to eyes, respiratory system and skin.
S-phrase(s)
S26 In case of contact with eyes, rinse immediately with plenty of water and
seek medical advice.
S36 Wear suitable protective clothing.
Other hazards - none

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Section 3. COMPOSITION/INFORMATION ON INGREDIENTS
Substances
Formula : 13CC6H12O4
Molecular Weight : 161,16 g/mol
Component Concentration
Diethyl malonate-2-13C
CAS-No. 67035-94-3 -

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Section 4. FIRST AID MEASURES
Description of first aid measures
General advice
Consult a physician. Show this safety data sheet to the doctor in attendance.
If inhaled
If breathed in, move person into fresh air. If not breathing, give artificial respiration. Consult a physician.
In case of skin contact
Wash off with soap and plenty of water. Consult a physician.
In case of eye contact
Rinse thoroughly with plenty of water for at least 15 minutes and consult a physician.
If swallowed
Never give anything by mouth to an unconscious person. Rinse mouth with water. Consult a physician.
Most important symptoms and effects, both acute and delayed
To the best of our knowledge, the chemical, physical, and toxicological properties have not been thoroughly
investigated.
Indication of any immediate medical attention and special treatment needed
no data available

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Section 5. FIRE-FIGHTING MEASURES
Extinguishing media
Suitable extinguishing media
Use water spray, alcohol-resistant foam, dry chemical or carbon dioxide.
Special hazards arising from the substance or mixture
Carbon oxides
Advice for firefighters
Wear self contained breathing apparatus for fire fighting if necessary.
Further information
no data available

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Section 6. ACCIDENTAL RELEASE MEASURES
Personal precautions, protective equipment and emergency procedures
Use personal protective equipment. Avoid breathing vapors, mist or gas. Ensure adequate ventilation.
Evacuate personnel to safe areas.
Environmental precautions
Do not let product enter drains.
Methods and materials for containment and cleaning up
Soak up with inert absorbent material and dispose of as hazardous waste. Keep in suitable, closed
containers for disposal.
Reference to other sections
For disposal see section 13.

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Section 7. HANDLING AND STORAGE
Precautions for safe handling
Avoid contact with skin and eyes. Avoid inhalation of vapour or mist.
Conditions for safe storage, including any incompatibilities
Store in cool place. Keep container tightly closed in a dry and well-ventilated place. Containers which are
opened must be carefully resealed and kept upright to prevent leakage.
Store under inert gas. hygroscopic
Specific end uses
no data available

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Section 8. EXPOSURE CONTROLS/PERSONAL PROTECTION
Control parameters
Components with workplace control parameters
Exposure controls
Appropriate engineering controls
Handle in accordance with good industrial hygiene and safety practice. Wash hands before breaks and at
the end of workday.
Personal protective equipment
Eye/face protection
Safety glasses with side-shields conforming to EN166 Use equipment for eye protection tested and
approved under appropriate government standards such as NIOSH (US) or EN 166(EU).
Skin protection
Handle with gloves. Gloves must be inspected prior to use. Use proper glove removal technique
(without touching glove's outer surface) to avoid skin contact with this product. Dispose of
contaminated gloves after use in accordance with applicable laws and good laboratory practices.
Wash and dry hands.
The selected protective gloves have to satisfy the specifications of EU Directive 89/686/EEC and the
standard EN 374 derived from it.
Body Protection
impervious clothing, The type of protective equipment must be selected according to the
concentration and amount of the dangerous substance at the specific workplace.
Respiratory protection
Where risk assessment shows air-purifying respirators are appropriate use a full-face respirator with
multi-purpose combination (US) or type ABEK (EN 14387) respirator cartridges as a backup to
engineering controls. If the respirator is the sole means of protection, use a full-face supplied air
respirator. Use respirators and components tested and approved under appropriate government
standards such as NIOSH (US) or CEN (EU).

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Section 9. PHYSICAL AND CHEMICAL PROPERTIES
Information on basic physical and chemical properties
a) Appearance Form: liquid
b) Odour no data available
c) Odour Threshold no data available
d) pH no data available
e) Melting point/freezing Melting point/range: -50 °C
point
f) Initial boiling point and 199 °C at 1.013 hPa
boiling range
g) Flash point 100 °C - closed cup
h) Evaporation rate no data available
i) Flammability (solid, gas) no data available
j) Upper/lower no data available
flammability or
explosive limits
k) Vapour pressure 1 hPa at 40 °C
l) Vapour density 5,52 - (Air = 1.0)
m) Relative density 1,054 g/cm3
n) Water solubility no data available
o) Partition coefficient: n- no data available
octanol/water
p) Autoignition no data available
temperature
q) Decomposition no data available
temperature
r) Viscosity no data available
s) Explosive properties no data available
t) Oxidizing properties no data available
Other safety information
no data available

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Section 10. STABILITY AND REACTIVITY
Reactivity
no data available
Chemical stability
no data available
Possibility of hazardous reactions
no data available
Conditions to avoid
no data available
Incompatible materials
Strong oxidizing agents
Hazardous decomposition products
Other decomposition products - no data available

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Section 11. TOXICOLOGICAL INFORMATION
Information on toxicological effects
Acute toxicity
no data available
Skin corrosion/irritation
no data available
Serious eye damage/eye irritation
no data available
Respiratory or skin sensitization
no data available
Germ cell mutagenicity
no data available
Carcinogenicity
IARC: No component of this product present at levels greater than or equal to 0.1% is identified as
probable, possible or confirmed human carcinogen by IARC.
Reproductive toxicity
no data available
Specific target organ toxicity - single exposure
no data available
Specific target organ toxicity - repeated exposure
no data available
Aspiration hazard
no data available
Potential health effects
Inhalation May be harmful if inhaled. Causes respiratory tract irritation.
Ingestion May be harmful if swallowed.
Skin May be harmful if absorbed through skin. Causes skin irritation.
Eyes Causes serious eye irritation.
Signs and Symptoms of Exposure
To the best of our knowledge, the chemical, physical, and toxicological properties have not been thoroughly
investigated.
Additional Information
RTECS: Not available

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Section 12. ECOLOGICAL INFORMATION
Toxicity
no data available
Persistence and degradability
no data available
Bioaccumulative potential
no data available
Mobility in soil
no data available
Results of PBT and vPvB assessment
no data available
Other adverse effects
no data available

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Section 13. DISPOSAL CONSIDERATIONS
Waste treatment methods
Product
Offer surplus and non-recyclable solutions to a licensed disposal company.
Contaminated packaging
Dispose of as unused product.

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Section 14. TRANSPORT INFORMATION
UN number
ADR/RID: - IMDG: - IATA: -
UN proper shipping name
ADR/RID: Not dangerous goods
IMDG: Not dangerous goods
IATA: Not dangerous goods
Transport hazard class(es)
ADR/RID: - IMDG: - IATA: -
Packaging group
ADR/RID: - IMDG: - IATA: -
Environmental hazards
ADR/RID: no IMDG Marine pollutant: no IATA: no
Special precautions for user
no data available

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Section 15. REGULATORY INFORMATION
This safety datasheet complies with the requirements of Regulation (EC) No. 1907/2006.
Safety, health and environmental regulations/legislation specific for the substance or mixture
no data available
Chemical Safety Assessment

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SECTION 16 - ADDITIONAL INFORMATION
N/A

反应信息

• 作为反应物：
  描述：

  丙二酸二乙酯-2-13C 在 ammonium hydroxide 作用下， 以93%的产率得到[2-¹³C]malonodiamide
  参考文献：
  名称：

  轻度，热五氟乙烯对苯的重排

  摘要：

  沿这种方式走：发现富勒烯可以在高温下热重排列为苯40多年后，人们发现在温和的条件下，6,6-二氰基戊烯富勒酸可以定量重排为1,3和1,4-二氰基苯。极性非质子溶剂。提出了一种极性“环游”机制来解释这种空前的反应性。

  DOI：

  10.1002/anie.201304767
• 作为产物：
  描述：

  乙酸乙酯-2-13C 、 氯甲酸乙酯 在 lithium hexamethyldisilazane 作用下， 以 四氢呋喃 为溶剂， 以90%的产率得到丙二酸二乙酯-2-13C
  参考文献：
  名称：

  A Convenient Synthesis of 4-Hydroxy[1-13C]benzoic Acid and Related Ring-Labelled Phenolic Compounds

  摘要：

  DOI：

  10.1055/s-1998-2109

文献信息

• The synthesis of [3,4,1′-13C3]genistein
  作者：Mark F. Oldfield、Lirong Chen、Nigel P. Botting

  DOI：10.1002/jlcr.1460

  日期：2007.12

  A facile synthesis is described for [3,4,1′-13C3]genistein for use as an internal standard in isoflavone analysis by mass spectrometric methods. Ethyl 4-hydroxy[1-13C]benzoate was first prepared from the reaction of diethyl [2-13C]malonate and 4H-pyran-4-one. Two further 13C atoms were incorporated using potassium [13C]cyanide as the source to give 4′-benzyloxy-[1,2,1′-13C3]phenylacetonitrile. [3,4

  描述了 [3,4,1'-13C3] 染料木黄酮的简单合成，用作质谱法分析异黄酮的内标。4-羟基[1-13C]苯甲酸乙酯首先由[2-13C]丙二酸二乙酯和4H-吡喃-4-酮反应制备。使用 [13C] 氰化钾作为来源并入另外两个 13C 原子，得到 4'-苄氧基-[1,2,1'-13C3]苯基乙腈。[3,4,1'-13C3]然后通过在Hoesch条件下将同位素标记的苯乙腈与间苯三酚偶联，然后进行甲酰化和环化来构建染料木黄酮。版权所有 © 2007 John Wiley & Sons, Ltd.
• Site-Selective Synthesis of ¹⁵N- and ¹³C-Enriched Flavin Mononucleotide Coenzyme Isotopologues
  作者：Syam Sundar Neti、C. Dale Poulter

  DOI：10.1021/acs.joc.6b00640

  日期：2016.6.17

  involved in key cellular and physiological processes. Isotopically labeled flavin is a powerful tool for studying the structure and mechanism of flavoenzyme-catalyzed reactions by a variety of techniques, including NMR, IR, Raman, and mass spectrometry. In this report, we describe the preparation of labeled FMN isotopologues enriched with 15N and 13C isotopes at various sites in the pyrazine and pyrimidine

  黄素单核苷酸（FMN）是参与关键细胞和生理过程的众多蛋白质的辅酶。同位素标记的黄素是通过各种技术（包括NMR，IR，拉曼和质谱法）研究黄素酶催化反应的结构和机制的强大工具。在这份报告中，我们描述了通过五步化学酶促合成方法，从易得的前体中制备富集15 N和13 C同位素的，富含15 N和13 C同位素的标记的FMN同位素，辅酶的异四恶嗪核心的吡嗪和嘧啶环。
• Synthesis and spectroscopic characterisation of ¹³ C-labelled ubiquinone-0 and ubiquinone-10
  作者：W.B.S. van Liemt、W.F. Steggerda、R. Esmeijer、J. Lugtenburg

  DOI：10.1002/recl.19941130305

  日期：——

  (3-13C)-, (3-13CH3)-, (4-13C), and (13CH3O)2- ubiquinone-10 and the corresponding (1-13C)-, (6-13C)-, (5-13C)-, (5-13CH3)-, (4-13C)-, and (13CH3O)2-ubiquinone-0 have been synthesised from simple labelled starting materials via a single reaction scheme. The ubiquinones have been characterised using mass spectrometry, 1H NMR and 13C NMR. The spectroscopic results indicate that, within experimental error

  （1- 13 C） - ，（2- 13 C） - ，（3- 13 C） - ，（3- 13 CH 3） - ，（4- 13 C），和（13 CH 3 O）2 -泛醌-10和相应的（1- 13 C） - ，（6- 13 C） - ， - （5- 13 C） - ， - （5- 13 CH 3） - ，（4- 13 C） - ，和（13 CH 3 O）2-泛醌-0已经通过简单的反应方案由简单的标记起始原料合成。泛醌已使用质谱，1 H NMR和13 C NMR。光谱结果表明，在实验误差范围内，已经完成合成，而没有加扰或稀释标记。所有标记的泛醌均已以分贝规模合成。
• Unexpected stereoselective exchange of straight-chain fatty acyl-CoA α-protons by human α-methylacyl-CoA racemase 1A (P504S)
  作者：Fouzia A. Sattar、Daniel J. Darley、Francesco Politano、Timothy J. Woodman、Michael D. Threadgill、Matthew D. Lloyd

  DOI：10.1039/c002509g

  日期：——

  α-Methylacyl-CoA racemase (AMACR; P504S) catalysed exchange of straight-chain fatty acyl-CoA α-protons. One α-proton was removed in each catalytic cycle, with the pro-S proton preferred. This reaction was most efficient for straight-chain substrates with longer side-chains. 2-Methyldecanoyl-CoA underwent α-proton exchange 3× more efficiently (as judged by Kcat/Km) than decanoyl-CoA.

  α-甲基酰基辅酶A外消旋酶（AMACR；P504S）催化直链脂肪酰基辅酶A的α-质子交换。在每个催化循环中移除一个α-质子，且优先移除pro-S质子。这一反应对长侧链的直链底物效率最高。2-甲基癸酰基辅酶A的α-质子交换效率（以Kcat/Km衡量）是癸酰基辅酶A的3倍。
• Synthesis and use of isotope-labelled substrates for a mechanistic study on human α-methylacyl-CoA racemase 1A (AMACR; P504S)
  作者：Daniel J. Darley、Danica S. Butler、Samuel J. Prideaux、Thomas W. Thornton、Abigail D. Wilson、Timothy J. Woodman、Michael D. Threadgill、Matthew D. Lloyd

  DOI：10.1039/b815396e

  日期：——

  α-Methylacyl-CoA racemase (AMACR) is an important enzyme for the metabolism of branched-chain lipids and drugs. The enzyme is over-expressed in prostate and other cancers. AMACR 1A, the major splice variant, was purified from recombinant E. colicells as a His-tag protein. Purified enzyme catalysed chiral inversion of both S- and R-2-methyldecanoyl-CoA, with an equilibrium constant of 1.09 ± 0.14 (2S/2R). Reactions with 2H-labelled substrate showed that loss of the α-proton was a prerequisite for chiral inversion. Reactions conducted in 2H2O indicated that reprotonation was not stereospecific. These results are the first mechanistic study on any recombinant mammalian α-methylacyl-CoA racemase.

  δ-甲基酰-CoA 消旋酶（AMACR）是支链脂质和药物代谢的一种重要酶。该酶在前列腺癌和其他癌症中过度表达。AMACR 1A 是主要的剪接变体，以 His 标记蛋白的形式从重组大肠杆菌中纯化。纯化的酶可催化 S- 和 R-2-methyldecanoyl-CoA 的手性反转，平衡常数为 1.09 ± 0.14 (2S/2R)。与 2H 标记底物的反应表明，δ-质子的损失是手性反转的先决条件。在 2H2O 中进行的反应表明，再质子化不是立体特异性的。这些结果是首次对任何重组哺乳动物δ-甲基酰-CoA 消旋酶进行机理研究。