胆碱 | 62-49-7

• 物质功能分类: 原料药 - 神经系统用药 - 拟胆碱药
• 分子结构分类: 有机化合物 - 有机氮化合物
• 中文名称: 胆碱
• 中文别名: L-胆碱；2-羟基-N,N,N-三甲基乙铵
• 英文名称: choline
• 英文别名: 2-hydroxyethyl(trimethyl)azanium
• CAS: 62-49-7
• 化学式: C₅H₁₄NO
• mdl: MFCD00272239
• 分子量: 104.172
• InChiKey: OEYIOHPDSNJKLS-UHFFFAOYSA-N

物化性质

• 熔点：
  232-233 °C (decomp)
• 沸点：
  195.35°C (rough estimate)
• 密度：
  1.09 g/mL at 20 °C
• 溶解度：
  Easily soluble (water), soluble (ethanol), slightly soluble (amyl alcohol), insoluble ((C2H5)2O, CHCl3)
• 物理描述：
  Solid
• 碰撞截面：
  117.8 Ų [M+H]+ [CCS Type: DT, Method: single field calibrated with Agilent tune mix (Agilent)]
• 稳定性/保质期：
  在酸性溶液中对热稳定，但在空气中易吸收二氧化碳且吸水性强，遇热会分解。其味道辛而苦。

计算性质

• 辛醇/水分配系数(LogP)：
  -0.4
• 重原子数：
  7
• 可旋转键数：
  2
• 环数：
  0.0
• sp3杂化的碳原子比例：
  1.0
• 拓扑面积：
  20.2
• 氢给体数：
  1
• 氢受体数：
  1

ADMET

代谢

胆碱已知的人类代谢产物包括乙醛和三甲基铵。

Choline has known human metabolites that include acetaldehyde and Trimethylazanium.

来源:NORMAN Suspect List Exchange

毒理性

• 副作用

Dermatotoxin - 皮肤烧伤。

Dermatotoxin - Skin burns.

来源:Haz-Map, Information on Hazardous Chemicals and Occupational Diseases

安全信息

• 危险等级：
  8
• 危险品标志：
  C
• 安全说明：
  S26,S36/37/39,S45
• 危险类别码：
  R34
• WGK Germany：
  1
• 危险品运输编号：
  UN 3286 3/PG 2
• 包装等级：
  II
• 危险类别：
  8
• 储存条件：
  2-8°C

SDS

Name:	Choline (Pract) (45% in Methanol) Material Safety Data Sheet
Synonym:
CAS:	62-49-7

Section 1 - Chemical Product MSDS Name:Choline (Pract) (45% in Methanol) Material Safety Data Sheet
Synonym:

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Section 2 - COMPOSITION, INFORMATION ON INGREDIENTS

CAS#	Chemical Name	content	EINECS#
62-49-7	Choline	45	200-535-1

Hazard Symbols: T F
Risk Phrases: 11 34

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Section 3 - HAZARDS IDENTIFICATION
EMERGENCY OVERVIEW
Highly flammable. Causes burns.
Potential Health Effects
Eye:
Vapors may cause eye irritation. May cause painful sensitization to light. May cause severe eye irritation and possible injury.
Skin:
May cause skin irritation. May be absorbed through the skin.
Ingestion:
May be fatal or cause blindness if swallowed. May cause irritation of the digestive tract. May cause kidney damage. May cause systemic toxicity with acidosis. May cause central nervous system depression, characterized by excitement, followed by headache, dizziness, drowsiness, and nausea. Advanced stages may cause collapse, unconsciousness, coma and possible death due to respiratory failure.
Inhalation:
Inhalation of high concentrations may cause central nervous system effects characterized by nausea, headache, dizziness, unconsciousness and coma. May cause respiratory tract irritation. May cause visual impairment and possible permanent blindness. May cause effects similar to those described for ingestion. Vapors may cause dizziness or suffocation.
Chronic:
Chronic inhalation and ingestion may cause effects similar to those of acute inhalation and ingestion.

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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. Immediately flush skin with plenty of water for at least 15 minutes while removing contaminated clothing and shoes.
Wash clothing before reuse.
Ingestion:
Call a poison control center. If swallowed, do not induce vomiting unless directed to do so by medical personnel. Never give anything by mouth to an unconscious person. Get medical aid.
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. Vapors may form an explosive mixture with air. Use water spray to keep fire-exposed containers cool. Extremely flammable liquid and vapor. Containers may explode in the heat of a fire. Will be easily ignited by heat, sparks or flame.
Extinguishing Media:
For small fires, use dry chemical, carbon dioxide, water spray or alcohol-resistant foam. For large fires, use water spray, fog, or alcohol-resistant foam. Use water spray to cool fire-exposed containers. Water may be ineffective. Do NOT use straight streams of water.

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Section 6 - ACCIDENTAL RELEASE MEASURES
General Information: Use proper personal protective equipment as indicated in Section 8.
Spills/Leaks:
Absorb spill with inert material (e.g. vermiculite, sand or earth), then place in suitable container. Remove all sources of ignition.
Provide ventilation. A vapor suppressing foam may be used to reduce vapors. Water spray may reduce vapor but may not prevent ignition in closed spaces.

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Section 7 - HANDLING and STORAGE
Handling:
Wash thoroughly after handling. Ground and bond containers when transferring material. Avoid contact with eyes, skin, and clothing.
Empty containers retain product residue, (liquid and/or vapor), and can be dangerous. Keep container tightly closed. Keep away from heat, sparks and flame. Avoid ingestion and inhalation. Use only in a chemical fume hood. Do not pressurize, cut, weld, braze, solder, drill, grind, or expose empty containers to heat, sparks or open flames.
Storage:
Keep away from heat, sparks, and flame. Keep away from sources of ignition. Do not store in direct sunlight. 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. Use only under a chemical fume hood.
Exposure Limits CAS# 62-49-7: CAS# 67-56-1: United Kingdom, WEL - TWA: 200 ppm TWA; 266 mg/m3 TWA United Kingdom, WEL - STEL: 250 ppm STEL; 333 mg/m3 STEL United States OSHA: 200 ppm TWA; 260 mg/m3 TWA Belgium - TWA: 200 ppm VLE; 266 mg/m3 VLE Belgium - STEL: 250 ppm VLE; 333 mg/m3 VLE France - VME: 200 ppm VME; 260 mg/m3 VME France - VLE: 1000 ppm VLE; 1300 mg/m3 VLE Germany: 200 ppm TWA; 270 mg/m3 TWA Germany: Skin absorber Japan: 200 ppm OEL; 260 mg/m3 OEL Malaysia: 200 ppm TWA; 262 mg/m3 TWA Netherlands: 200 ppm MAC; 260 mg/m3 MAC Russia: 5 mg/m3 TWA Spain: 200 ppm VLA-ED; 266 mg/m3 VLA-ED Spain: 250 ppm VLA-EC; 333 mg/m3 VLA-EC 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: Liquid
Color: clear colorless to almost colorless
Odor: Amine-like odor
pH: Not available.
Vapor Pressure: Not available.
Viscosity: Not available.
Boiling Point: 113 deg C @ 760.00mm Hg
Freezing/Melting Point: Not available.
Autoignition Temperature: 349 deg C ( 660.20 deg F)
Flash Point: -33 deg C ( -27.40 deg F)
Explosion Limits, lower: N/A
Explosion Limits, upper: N/A
Decomposition Temperature:
Solubility in water: soluble
Specific Gravity/Density: .9400g/cm3
Molecular Formula: Not applicable.
Molecular Weight:

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Section 10 - STABILITY AND REACTIVITY
Chemical Stability:
Stable under normal temperatures and pressures.
Conditions to Avoid:
Incompatible materials, light, ignition sources, exposure to air, excess heat.
Incompatibilities with Other Materials:
Acids (mineral, non-oxidizing, e.g. hydrochloric acid, hydrofluoric acid, muriatic acid, phosphoric acid), acids (mineral, oxidizing, e.g. chromic acid, hypochlorous acid, nitric acid, sulfuric acid), acids (organic, e.g. acetic acid, benzoic acid, formic acid, methanoic acid, oxalic acid), azo, diazo, and hydrazines (e.g.
dimethyl hydrazine, hydrazine, methyl hydrazine), isocyanates (e.g.
methyl isocyanate), metals (alkali and alkaline, e.g. cesium, potassium, sodium), nitrides (e.g. potassium nitride, sodium nitride), peroxides and hydroperoxides (organic, e.g. acetyl peroxide, benzoyl peroxide, butyl peroxide, methyl ethyl ketone peroxide), epoxides (e.g. butyl glycidyl ether), oxidizing agents (strong, e.g. bromine, hydrogen peroxide, nitrogen dioxide, potassium nitrate), reducing agents (strong, e.g. aluminum carbide, chlorosilane, hydrogen phosphide, lithium hydride), water reactive substances (e.g. acetic anyhdride, alkyl aluminum chloride, calcium carbide, ethyl dichlorosilane).
Hazardous Decomposition Products:
Nitrogen oxides, carbon monoxide, carbon dioxide.
Hazardous Polymerization: Will not occur.

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Section 11 - TOXICOLOGICAL INFORMATION
RTECS#:
CAS# 62-49-7: FZ9625000 CAS# 67-56-1: PC1400000 LD50/LC50:
Not available.
CAS# 67-56-1: Draize test, rabbit, eye: 40 mg Moderate; Draize test, rabbit, eye: 100 mg/24H Moderate; Draize test, rabbit, skin: 20 mg/24H Moderate; Inhalation, rabbit: LC50 = 81000 mg/m3/14H; Inhalation, rat: LC50 = 64000 ppm/4H; Oral, mouse: LD50 = 7300 mg/kg; Oral, rabbit: LD50 = 14200 mg/kg; Oral, rat: LD50 = 5600 mg/kg; Skin, rabbit: LD50 = 15800 mg/kg.
Carcinogenicity:
Choline - Not listed by ACGIH, IARC, or NTP.
Methyl alcohol - 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
Shipping Name: FLAMMABLE LIQUID, CORROSIVE, N.O.S.*
Hazard Class: 3 (8)
UN Number: 2924
Packing Group: II
IMO
Shipping Name: FLAMMABLE LIQUID, CORROSIVE, N.O.S.
Hazard Class: 3.2 (8)
UN Number: 2924
Packing Group: II
RID/ADR
Shipping Name: FLAMMABLE LIQUID, CORROSIVE, N.O.S.
Hazard Class: 3
UN Number: 2924
Packing group: II
USA RQ: CAS# 67-56-1: 5000 lb final RQ; 2270 kg final RQ

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Section 15 - REGULATORY INFORMATION

European/International Regulations
European Labeling in Accordance with EC Directives
Hazard Symbols: T F
Risk Phrases:
R 11 Highly flammable.
R 34 Causes burns.
Safety Phrases:
S 16 Keep away from sources of ignition - No
smoking.
S 28A After contact with skin, wash immediately with
plenty of water.
S 33 Take precautionary measures against static
discharges.
S 36/37/39 Wear suitable protective clothing, gloves
and eye/face protection.
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# 62-49-7: No information available.
CAS# 67-56-1: 1
Canada
CAS# 62-49-7 is listed on Canada's DSL List.
CAS# 67-56-1 is listed on Canada's DSL List.
CAS# 62-49-7 is not listed on Canada's Ingredient Disclosure List.
CAS# 67-56-1 is listed on Canada's Ingredient Disclosure List.
US FEDERAL
TSCA
CAS# 62-49-7 is listed on the TSCA inventory.
CAS# 67-56-1 is listed on the TSCA inventory.

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SECTION 16 - ADDITIONAL INFORMATION
N/A

制备方法与用途

简介

胆碱是一种带正电荷的四价碱基，是所有生物膜的重要组成成分，并且也是乙酰胆碱（一种胆碱能神经元中的重要物质）的前体。在人体内，胆碱主要通过肝脏或卵类食物获取，这些食物中胆碱主要以磷脂酰胆碱（PC）的形式存在；另外，它也可以由内源性合成的磷脂酰乙醇胺（PE）通过连续甲基化过程生成。除了作为大分子PC的一部分而获得外，人体不能直接合成胆碱，但所有细胞都能通过PE甲基化产生PC，并在特定酶的作用下将食物和内源性PC中的胆碱释放出来。

用途

胆碱具有多种生理功能，包括促进脑发育和提高记忆能力、保证信息传递、调控细胞凋亡、构成生物膜的重要组成成分、促进脂肪代谢以及降低血清胆固醇等作用。

毒性

胆碱的半数致死量（LD₅₀）为400 mg/kg（大鼠，腹腔注射）。

使用限量

• GB 14880—94：婴幼儿食品中胆碱含量应在380～790 mg/kg。
• GB 2760 2001：果冻中的胆碱使用限量为50～100 mg/kg。

生产方法

胆碱的生产通常通过以下步骤实现：首先，甲醛经过氯化铵甲基化得到三甲胺；然后，再与环氧乙烷进行加成反应即可获得胆碱。

反应信息

• 作为反应物：
  描述：

  胆碱 生成 N,N-二甲基乙醇胺
  参考文献：
  名称：

  Meyer,K.H.; Hopff, Chemische Berichte, 1921, vol. 54, p. 2279

  摘要：

  DOI：
• 作为产物：
  描述：

  氯化乙酰胆碱 在 水 作用下， 以 aq. phosphate buffer 为溶剂， 生成 胆碱
  参考文献：
  名称：

  Bioactive MIL-88A Framework Hollow Spheres via Interfacial Reaction In-Droplet Microfluidics for Enzyme and Nanoparticle Encapsulation

  摘要：

  利用连续流液滴微流体系统，通过界面反应，成功合成了尺寸在 35-2000 μm 范围内可控的功能性生物-MOF 空心球。MIL-88A 框架的结构从单壳空心球扩展到双壳空心球。此外，在保持货物功能性的前提下，各种功能纳米颗粒（二氧化硅、钴和 UiO-66(Zr) MOF）被直接封装在单壳空心球中。其中，三种酶（甘油脱氢酶、辣根过氧化物酶和乙酰胆碱酯酶）也在温和条件下被封装在单壳空心球内。与游离酶相比，封装酶的催化活性和可回收性更优越。

  DOI：

  10.1021/acs.chemmater.5b02847
• 作为试剂：
  描述：

  哌啶 、 alkaline earth salt of/the/ methylsulfuric acid 在 甲醇 、 胆碱 作用下， 35.0 ℃ 、27.46 MPa 条件下， 生成 哌啶-1-甲醛
  参考文献：
  名称：

  Preparation of formamides

  摘要：

  公开号：

  US02793211A1

文献信息

• Cucurbit[7]urilhost–guest complexes of cholines and phosphonium cholines in aqueous solution
  作者：Ian W. Wyman、Donal H. Macartney

  DOI：10.1039/b917610a

  日期：——

  The neutral host cucurbit[7]uril forms very stable complexes with a series of cationic cholines (R3NCH2CH2OR′+) and their phosphonium analogues (R3PCH2CH2OR′+) (R3 = Me3, Et3, or Me2Bz, or R3N = quinuclidinium, and R′ = H, COCH3, CO(CH2)2CH3, or PO3H), and (±)-carnitine, in aqueous solution. The complexation behaviour has been investigated using 1H and 31P NMR spectroscopies, and ESI mass spectrometry. The complexation-induced chemical shift changes of the guests clearly indicate the effects of replacing the N(CH3)3+ end group by P(CH3)3+, and changing the nature of R on the position of the guest with respect to the CB[7] cavity and its polar portal-lining carbonyl groups. This study demonstrates that molecular recognition of cholines in aqueous solution is achievable with a neutral host without the need for aromatic walls for cation–π interactions.

  中性主体瓜环[7]与一系列阳离子胆碱（R3NCH2CH2OR' +）及其膦鎓类似物（R3PCH2CH2OR' +）（R3 = Me3、Et3、Me2Bz，或R3N =奎宁环鎓，R' = H、COCH3、CO(CH2)2CH3、或PO3H）以及（±）-肉碱在水溶液中形成非常稳定的复合物。利用1H和31P核磁共振波谱学以及ESI质谱法研究了复合行为。客体分子的复合诱导化学位移变化清楚地表明了通过P(CH3)3+取代N(CH3)3+末端基团以及改变R的性质对客体相对于CB[7]腔体及其极性门户面羰基位置的影响。这一研究表明，无需利用芳香壁进行阳离子-π相互作用，即可实现水溶液中对胆碱的分子识别。
• 一种制备 2,4-（1H, 3H）-喹唑啉二酮类化合物的方法
  申请人：浙江外国语学院

  公开号：CN112778219A

  公开（公告）日：2021-05-11

  本发明公开了一种制备2,4‑（1H,3H）‑喹唑啉二酮类化合物的方法，它以式（1）所示的2‑氨基苯甲氰类化合物和二氧化碳为原料，在2‑羟基吡啶型离子液体中反应得到式（II）所示的2,4‑（1H,3H）‑喹唑啉二酮类化合物，其反应式如下：。本发明的离子液体在应用于制备2,4‑（1H,3H）‑喹唑啉二酮类化合物的反应中时，反应条件较为温和，产物的分离纯化过程较为简单，产物产率高，底物适用范围广。
• The Effect of Carbon Source, Temperature and Aeration on the Production of Ascosteroside, a Novel Antifungal Agent, by Ascotricha amphitricha.
  作者：SUSAN E. LOWE、DONALD R. GUSTAVSON、DAVID S. MEYERS、JUDITH A. VEITCH、SALVATORE FORENZA、KIN SING LAM

  DOI：10.7164/antibiotics.50.412

  日期：——

  This paper describes the optimization of production of ascosteroside, a novel antifungal agent with an α-linked glycoside of a lanosterone-type triterpenoid structure. Glucose, sorbose and inositol were determined to be the best carbon sources for the production of ascosteroside. Temperature affected levels of ascosteroside, with production being highest at 16°C with 1% glucose, and lowest at 32°C. Dissolved oxygen levels were found to be critical in the production of ascosteroside in fermenter cultures. In order for production of ascosteroside to occur in fermenter cultures, the threshold level of dissolved oxygen was found to be above 26%.

  本文描述了新型抗真菌剂鳐柱苷（一种具有羊毛甾烷型三萜结构的α-连接的糖苷）生产过程的优化。研究表明，葡萄糖、山梨糖醇和肌醇是生产鳐柱苷的最佳碳源。温度对鳐柱苷的产量有影响，在1%葡萄糖条件下，16°C时产量最高，而32°C时产量最低。在发酵罐培养中，溶解氧水平对鳐柱苷的生产至关重要。为了在发酵罐培养中生产鳐柱苷，发现溶解氧的阈值水平必须高于26%。
• A facile one-step synthesis of 5′-phosphatidylnucleosides by an enzymatic two-phase reaction.
  作者：Satoshi Shuto、Shigeru Ueda、Shigeyuki Imamura、Kiyofumi Fukukawa、Akira Matsuda、Tohru Ueda

  DOI：10.1016/s0040-4039(00)95685-5

  日期：1987.1

  Phospholipase D from effectively catalyzed the transfer reaction of the phosphatidyl residue from phosphatidylcholines to the 5′-hydroxyl group of nucleosides in a two-phase system. A variety of 5′-phosphatidylnucleosides were easily prepared in high yields by this reaction.

  磷脂酶D在两相系统中有效催化了磷脂酰残基从磷脂酰胆碱到核苷的5'-羟基的转移反应。通过该反应，可以容易地以高收率制备各种5'-磷脂酰核苷。
• Hydrogen bonding-catalysed alcoholysis of propylene oxide at room temperature
  作者：Yueting Xu、Yanfei Zhao、Fengtao Zhang、Yuepeng Wang、Ruipeng Li、Junfeng Xiang、Zhimin Liu

  DOI：10.1039/d1cc03602e

  日期：——

  Alcoholysis of propylene oxide (PO) is achieved over azolate ionic liquids (IL, e.g., 1-hydroxyethyl-3-methyl imidazolium imidazolate) at room temperature, accessing glycol ethers in high yields with excellent selectivity (e.g., >99%). Mechanism investigation indicates that cooperation of hydrogen-bonding of the anion with methanol and that of the cation with PO catalyses the reaction.

  环氧丙烷（PO）的醇解是在室温下在唑盐离子液体（IL，例如，1-羟乙基-3-甲基咪唑鎓咪唑盐）上实现的，以高产率和优异的选择性（例如，>99%）获得乙二醇醚。机理研究表明，阴离子与甲醇的氢键和阳离子与 PO 的氢键共同催化了反应。

表征谱图