N-甲基-L-脯氨酸 | 475-11-6

• 物质功能分类: 生物化工 - 氨基酸及其衍生物 - 脯氨酸类衍生物
• 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-甲基-L-脯氨酸
• 中文别名: N-甲基L-脯氨酸
• 英文名称: N-methyl-L-proline
• 英文别名: N-methylproline；(S)-1-methylpyrrolidine-2-carboxylic acid；(2S)-1-methylpyrrolidine-2-carboxylic acid；L-N-methylproline；methyl-L-proline；(S)-(-)-N-methylproline；N-Methyl-L-prolin；Monomethyl proline；(2S)-1-methylpyrrolidin-1-ium-2-carboxylate
• CAS: 475-11-6
• 化学式: C₆H₁₁NO₂
• mdl: MFCD01605583
• 分子量: 129.159
• InChiKey: CWLQUGTUXBXTLF-YFKPBYRVSA-N

物化性质

• 熔点：
  114-116 °C(lit.)
• 沸点：
  227℃
• 密度：
  1.153
• 闪点：
  91.1℃
• 溶解度：
  溶于氯仿、二氯甲烷、乙酸乙酯、DMSO、丙酮等。
• 稳定性/保质期：
  按规格使用和贮存，不会发生分解，避免与氧化物接触。

计算性质

• 辛醇/水分配系数(LogP)：
  -1.9
• 重原子数：
  9
• 可旋转键数：
  1
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.83
• 拓扑面积：
  40.5
• 氢给体数：
  1
• 氢受体数：
  3

安全信息

• 危险等级：
  IRRITANT
• WGK Germany：
  3
• 海关编码：
  2933990090
• 危险性防范说明：
  P261,P280,P305+P351+P338
• 危险性描述：
  H302,H315,H319,H332,H335
• 储存条件：
  -20°C密封保存，放置于通风、干燥处，避免与其它氧化物接触。

SDS

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SECTION 1: Identification of the substance/mixture and of the company/undertaking
Product identifiers
Product name : N-Methyl-L-proline
REACH No. : A registration number is not available for this substance as the substance
or its uses are exempted from registration, the annual tonnage does not
require a registration or the registration is envisaged for a later
registration deadline.
CAS-No. : 475-11-6
Relevant identified uses of the substance or mixture and uses advised against
Identified uses : Laboratory chemicals, Manufacture of substances

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SECTION 2: Hazards identification
Classification of the substance or mixture
Not a hazardous substance or mixture according to Regulation (EC) No. 1272/2008.
Not a hazardous substance or mixture according to EC-directives 67/548/EEC or 1999/45/EC.
Label elements
The product does not need to be labelled in accordance with EC directives or respective national laws.
Other hazards - none

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SECTION 3: Composition/information on ingredients
Substances
Chemical characterization : Natural product
Formula : C6H11NO2
Molecular Weight : 129,16 g/mol
CAS-No. : 475-11-6
No components need to be disclosed according to the applicable regulations.

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SECTION 4: First aid measures
Description of first aid measures
If inhaled
If breathed in, move person into fresh air. If not breathing, give artificial respiration.
In case of skin contact
Wash off with soap and plenty of water.
In case of eye contact
Flush eyes with water as a precaution.
If swallowed
Never give anything by mouth to an unconscious person. Rinse mouth with water.
Most important symptoms and effects, both acute and delayed
The most important known symptoms and effects are described in the labelling (see section 2.2) and/or in
section 11
Indication of any immediate medical attention and special treatment needed
no data available

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SECTION 5: Firefighting 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, nitrogen oxides (NOx)
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
Avoid dust formation. Avoid breathing vapours, mist or gas.
For personal protection see section 8.
Environmental precautions
Do not let product enter drains.
Methods and materials for containment and cleaning up
Sweep up and shovel. 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
Provide appropriate exhaust ventilation at places where dust is formed.
For precautions see section 2.2.
Conditions for safe storage, including any incompatibilities
Store in cool place. Keep container tightly closed in a dry and well-ventilated place.
Recommended storage temperature: -20 °C
Specific end use(s)
A part from the uses mentioned in section 1.2 no other specific uses are stipulated

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SECTION 8: Exposure controls/personal protection
Control parameters
Components with workplace control parameters
Exposure controls
Appropriate engineering controls
General industrial hygiene practice.
Personal protective equipment
Eye/face protection
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.
Full contact
Material: Nitrile rubber
Minimum layer thickness: 0,11 mm
Break through time: 480 min
Material tested:Dermatril® (KCL 740 / Z677272, Size M)
Splash contact
Material: Nitrile rubber
Minimum layer thickness: 0,11 mm
Break through time: 480 min
Material tested:Dermatril® (KCL 740 / Z677272, Size M)
data source: KCL GmbH, D-36124 Eichenzell, phone [phone], test method: EN374
If used in solution, or mixed with other substances, and under conditions which differ from EN 374,
contact the supplier of the CE approved gloves. This recommendation is advisory only and must
be evaluated by an industrial hygienist and safety officer familiar with the specific situation of
anticipated use by our customers. It should not be construed as offering an approval for any
specific use scenario.
Body Protection
Choose body protection in relation to its type, to the concentration and amount of dangerous
substances, and to the specific work-place., The type of protective equipment must be selected
according to the concentration and amount of the dangerous substance at the specific workplace.
Respiratory protection
Respiratory protection is not required. Where protection from nuisance levels of dusts are desired,
use type N95 (US) or type P1 (EN 143) dust masks. Use respirators and components tested and
approved under appropriate government standards such as NIOSH (US) or CEN (EU).
Control of environmental exposure
Do not let product enter drains.

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SECTION 9: Physical and chemical properties
Information on basic physical and chemical properties
a) Appearance Form: solid
b) Odour no data available
c) Odour Threshold no data available
d) pH no data available
e) Melting point/freezing Melting point/range: 114 - 116 °C
point
f) Initial boiling point and no data available
boiling range
g) Flash point no data available
h) Evapouration rate no data available
i) Flammability (solid, gas) no data available
j) Upper/lower no data available
flammability or
explosive limits
k) Vapour pressure no data available
l) Vapour density no data available
m) Relative density no data available
n) Water solubility no data available
o) Partition coefficient: n- no data available
octanol/water
p) Auto-ignition 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
Stable under recommended storage conditions.
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
In the event of fire: see section 5

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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 sensitisation
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
Additional Information
RTECS: Not available
To the best of our knowledge, the chemical, physical, and toxicological properties have not been
thoroughly investigated.

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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
PBT/vPvB assessment not available as chemical safety assessment not required/not conducted
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
N/A

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SECTION 16 - ADDITIONAL INFORMATION
N/A

制备方法与用途

合成制备方法： 暂无

用途： 暂无

上下游信息

• 上游原料

  中文名称	英文名称	CAS号	化学式	分子量
  L-脯氨酸	L-proline	147-85-3	C5H9NO2	115.132
  ——	(7aS)-5,6,7,7a-tetrahydro-3H-pyrrolo[1,2-c][1,3]oxazol-1-one	——	C6H9NO2	127.143

• 下游产品

  中文名称	英文名称	CAS号	化学式	分子量
  ——	methyl 1-methylpyrrolidine-2-carboxylate	933-94-8	C7H13NO2	143.186
  N-甲基-L-脯氨酸甲酯	N-Methyl-L-proline Methyl Ester	27957-91-1	C7H13NO2	143.186
  ——	N-methyl-L-proline ethyl ester	936-14-1	C8H15NO2	157.213
  (4S)-4-羟基-1-甲基-L-脯氨酸	N-methyl-cis-4-hydroxy-L-proline	67463-44-9	C6H11NO3	145.158
  ——	(2S,3R)-cis-3-hydroxy-N-methyl-L-proline	——	C6H11NO3	145.158
  N-甲基-L-脯氨醇	(S)-2-hydroxymethyl-1-methylpyrrolidine	34381-71-0	C6H13NO	115.175
  ——	benzyl (2S)-1-methyltetrahydro-1H-pyrrole-2-carboxylate	——	C13H17NO2	219.283

反应信息

• 作为反应物：
  描述：

  N-甲基-L-脯氨酸 在 盐酸 作用下， 以 甲醇 为溶剂， 反应 0.5h， 以94%的产率得到N-methyl-L-proline hydrochloride
  参考文献：
  名称：

  Design, synthesis, and biological evaluation of novel stachydrine derivatives as potent neuroprotective agents for cerebral ischemic stroke

  摘要：

  Stachydrine is a natural product with multiple protective biological activities, including those involved in preventing cancer, ischemia, and cardiovascular disease. However, its use has been limited by low bioavailability and unsatisfactory efficacy. To address this problem, a series of stachydrine derivatives (A1/A2/A3/A4/B1/B2/B3/B4) were designed and synthesized, and biological studies were carried out in vitro and in vivo. When compared with stachydrine, Compound B1 exhibited better neuroprotective effects in vitro, and significantly reduced infarction size in the model of the middle cerebral artery occlusion rat model. Therefore, Compound B1 was selected for further research on ischemic stroke.

  DOI：

  10.1007/s00210-020-01868-4
• 作为产物：
  描述：

  L-脯氨酸 在 palladium-carbon 聚合甲醛 作用下， 以 甲醇 为溶剂， 以90%的产率得到N-甲基-L-脯氨酸
  参考文献：
  名称：

  Method of preparing enantiomerically-pure

  摘要：

  一种新颖的方法，用于高产率制备对映纯的3-甲基-5-(1-(C.sub.1-C.sub.3-烷基)-2-吡咯烷基)异噁唑，其中保护的2-氧代吡咯烷起始物与适当的有机阴离子反应，生成的β-酮肟中间体被环化和脱水。

  公开号：

  US05516912A1
• 作为试剂：
  描述：

  3-(4-(benzyloxy)-3-methoxyphenyl)-prop-2-enal 在 potassium phosphate 、 copper(l) iodide 、 10 wt% Pd(OH)2 on carbon 、 氢气 、 三溴化硼 、 1,8-二氮杂双环[5.4.0]十一碳-7-烯 、 N-甲基-L-脯氨酸 作用下， 以 四氢呋喃 、 1,4-二氧六环 、 二氯甲烷 、 乙酸乙酯 为溶剂， 反应 91.75h， 生成 3',4"-epoxy-1-(4-hydroxyphenyl)-7-(3-hydroxyphenyl)heptan-3-one 、 4-hydroxy-17-methoxy-2-oxatricyclo[13.2.2.1^3,7]icosa-1(17),3(20),4,6,15,18-hexaene-10-one
  参考文献：
  名称：

  Enantioselective Ullmann Ether Couplings: Syntheses of (−)-Myricatomentogenin, (−)-Jugcathanin, (+)-Galeon, and (+)-Pterocarine

  摘要：

  The first enantioselective Ullmann cross-coupling reactions to prepare diaryl ethers are reported. The reactions were used to prepare the diarylether heptanoid natural products (-)-myricatomentogenin, (-)-jugcathanin, (+)-galeon, and (+)-pterocarine.

  DOI：

  10.1021/ol402096k

文献信息

• [EN] METABOLICALLY ROBUST ANALOGS OF CYP-EICOSANOIDS FOR THE TREATMENT OF CARDIAC DISEASE<br/>[FR] ANALOGUES ROBUSTES SUR LE PLAN MÉTABOLIQUE DES CYP-EICOSANOÏDES POUR LE TRAITEMENT DES MALADIES CARDIAQUES
  申请人：OMEICOS THERAPEUTICS GMBH

  公开号：WO2017013265A1

  公开（公告）日：2017-01-26

  The present invention relates to compounds according to general formula (I) which are metabolically robust analogues of bioactive lipid mediators derived from omega-3 polyunsaturated fatty acids (n-3 PUFAs).The present invention further relates to compositions containing one or more of these compounds and to the use of these compounds or compositions for the treatment or prevention of cardiovascular diseases.

  本发明涉及符合一般式（I）的化合物，这些化合物是从ω-3多不饱和脂肪酸（n-3 PUFAs）衍生的生物活性脂质介质的代谢稳健类似物。本发明还涉及含有这些化合物中的一个或多个的组合物，以及利用这些化合物或组合物治疗或预防心血管疾病。
• [EN] COMPOSITIONS AND METHODS FOR THE TREATMENT OF BACTERIAL INFECTIONS<br/>[FR] COMPOSÉS ET MÉTHODES POUR LE TRAITEMENT D'INFECTIONS BACTÉRIENNES
  申请人：CIDARA THERAPEUTICS INC

  公开号：WO2018006063A1

  公开（公告）日：2018-01-04

  Compositions and methods for the treatment of bacterial infections include compounds containing dimers of cyclic heptapeptides conjugated to one or more monosaccharide or oligosaccharide moieties. In particular, compounds can be used in the treatment of bacterial infections caused by Gram-negative bacteria.

  用于治疗细菌感染的组合物和方法包括含有环七肽二聚体与一个或多个单糖或寡糖基团结合的化合物。特别是，这些化合物可用于治疗由革兰氏阴性细菌引起的细菌感染。
• 2-[1H-Benzimidazol-2(3H)-ylidene]-2-(pyrimidin-2-yl)acetamides and 2-[benzothiazol-2(3H)-ylidene]-2-(pyrimidin-2-yl)acetamides as kinase inhibitors
  申请人：Aurrecoechea Natalia

  公开号：US20100081653A1

  公开（公告）日：2010-04-01

  2-[1H-benzimidazol-2(3H)-ylidene]-2-(pyrimidin-2-yl)acetamides and 2-[benzothiazol-2(3H)-ylidene]-2-(pyrimidin-2-yl)acetamides and their salts are kinase inhibitors, useful in the treatment of cancer.

  2-[1H-苯并咪唑-2(3H)-基]-2-(嘧啶-2-基)乙酰胺和2-[苯并噻唑-2(3H)-基]-2-(嘧啶-2-基)乙酰胺及其盐是激酶抑制剂，在癌症治疗中有用。
• Reductive methylation of primary and secondary amines and amino acids by aqueous formaldehyde and zinc
  作者：Renato A. da Silva、Idália H.S. Estevam、Lothar W. Bieber

  DOI：10.1016/j.tetlet.2007.08.092

  日期：2007.10

  Amines can be methylated when treated with formaldehyde and zinc in aqueous medium. Selective mono- or dimethylation can be achieved by proper choice of pH, stoichiometry and reaction time. This method can also be applied for amino acids.

  在水性介质中用甲醛和锌处理时，胺可被甲基化。选择性单或二甲基化可以通过pH值，化学计量和反应时间的适当选择来实现。该方法也可以用于氨基酸。
• [EN] PEPTIDE-BASED MULTIPLE-DRUG DELIVERY VEHICLE<br/>[FR] VÉHICULE D'ADMINISTRATION DE MÉDICAMENTS MULTIPLES À BASE DE PEPTIDES
  申请人：ARIEL-UNIVERSITY RES AND DEV COMPANY LTD

  公开号：WO2017068577A1

  公开（公告）日：2017-04-27

  A molecular structure comprising a targeting moiety, a multi-functional peptide platform and a plurality of controllably released bioactive agents attached thereto is provided herein.

  本文提供了一种包括靶向基团、多功能肽平台和附着在其上的多种可控释放的生物活性剂的分子结构。