氯化十六烷基吡啶 | 123-03-5

• 物质功能分类: 原料药 - 人工合成抗感染类药 - 消毒防腐药
• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吡啶及其衍生物
• 中文名称: 氯化十六烷基吡啶
• 中文别名: 西吡氯铵；盐酸芬司匹利；氯化-N-十六烷基吡啶翁盐；1-十六烷基吡啶氯化物；十六烷基氯化吡啶；氯化十六烷吡啶；氯代十六烷基吡啶
• 英文名称: cetylpyridinium chloride
• 英文别名: CPC；hexadecylpyridinium chloride；N-cetylpyridinium chloride；1-hexadecylpyridinium chloride；cetylpyridine chloride；Pristacin；1-Hexadecylpyridin-1-ium;chloride
• CAS: 123-03-5
• 化学式: C₂₁H₃₈N*Cl
• 分子量: 339.992
• InChiKey: YMKDRGPMQRFJGP-UHFFFAOYSA-M

物化性质

• 熔点：
  77°C
• 沸点：
  496.25°C (rough estimate)
• 密度：
  0.9362 (rough estimate)
• 溶解度：
  Freely soluble in water; very soluble in chloroform; very slightly soluble in ether; insoluble in acetone, acetic acid, and ethanol.
• LogP：
  1.71 at 20℃
• 物理描述：
  DryPowder
• 颜色/状态：
  White powder
• 分解：
  When heated to decomposition it emits very toxic fumes of /nitrogen oxides and hydrogen chloride/.
• 折光率：
  INDEX OF REFRACTION (@ 20 °C): MONOCLINIC 1.509; TRICLINIC 1.566; ORTHORHOMBIC 1.613
• 碰撞截面：
  197.5 Ų [M+H]+ [CCS Type: TW, Method: calibrated with polyalanine and drug standards]
• 稳定性/保质期：
  1%的水溶液pH值在6.0至7.0之间。强烈振荡其水溶液会生成大量泡沫。它具备出色的表面活性和良好的杀菌消毒效果。

计算性质

• 辛醇/水分配系数(LogP)：
  3.46
• 重原子数：
  23
• 可旋转键数：
  15
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.76
• 拓扑面积：
  3.9
• 氢给体数：
  0
• 氢受体数：
  1

ADMET

毒理性

• 副作用

神经毒素 - 其他中枢神经系统神经毒素 职业性肝毒素 - 继发性肝毒素：在职业环境中的毒性效应潜力基于人类摄入或动物实验的中毒案例。 高铁血红蛋白血症 - 血液中高铁血红蛋白含量增加；该化合物被归类为继发性毒性效应 皮肤毒素 - 皮肤烧伤。 皮肤致敏剂 - 能诱导皮肤过敏反应的剂。

Neurotoxin - Other CNS neurotoxin Occupational hepatotoxin - Secondary hepatotoxins: the potential for toxic effect in the occupational setting is based on cases of poisoning by human ingestion or animal experimentation. Methemoglobinemia - The presence of increased methemoglobin in the blood; the compound is classified as secondary toxic effect Dermatotoxin - Skin burns. Skin Sensitizer - An agent that can induce an allergic reaction in the skin.

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

毒理性

• 毒性数据

大鼠LC50 = 90毫克/立方米/4小时

LC50 (rat) = 90 mg/m3/4h

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

毒理性

• 相互作用

避免饮酒，因为这已被证明会增加...氯化十六烷基吡啶...的口腔毒性。

AVOID ALCOHOL, WHICH HAS BEEN SHOWN TO INCREASE THE ORAL TOXICITY OF ... CETYL PYRIDINIUM CHLORIDE ... .

来源:Hazardous Substances Data Bank (HSDB)

毒理性

• 相互作用

筒箭毒碱拮抗剂如新斯的明和艾卓酚（腾喜龙）...可能增强麻痹作用... ./氯化苯佐卡因/

CURARE ANTAGONISTS SUCH AS NEOSTIGMINE AND EDROPHONIUM (TENSILON) ... MAY ENHANCE THE PARALYSIS ... . /BENZALKONIUM CHLORIDE/

来源:Hazardous Substances Data Bank (HSDB)

毒理性

• 相互作用

... 与阴离子表面活性剂发生拮抗作用，包括肥皂 ... .

... ANTAGONIZED BY ANIONIC SURFACTANTS, INCL SOAPS ... .

来源:Hazardous Substances Data Bank (HSDB)

吸收、分配和排泄

口服给予的1分钟10毫升2.2毫摩尔溶液的氯化十六烷基吡啶的保留率为65%。

ORAL RETENTION OF CETYLPYRIDINIUM CHLORIDE GIVEN AS 1 MIN MOUTH RINSE OF 10 ML OF 2.2 MMOL SOLN WAS 65% OF ADMIN DOSE.

来源:Hazardous Substances Data Bank (HSDB)

安全信息

• 危险等级：
  6.1(b)
• 危险品运输编号：
  2811
• 海关编码：
  2933399090
• 危险类别：
  6.1(b)
• RTECS号：
  UU4900000
• 包装等级：
  III
• 危险性防范说明：
  P261,P305+P351+P338
• 危险性描述：
  H302,H315,H319,H335
• 储存条件：
  库房应保持低温、通风和干燥。

SDS

Name:	Cetylpyridinium chloride Material Safety Data Sheet
Synonym:	1-Hexadecylpyridinium chloride; CPC
CAS:	123-03-5

Section 1 - Chemical Product MSDS Name:Cetylpyridinium chloride Material Safety Data Sheet
Synonym:1-Hexadecylpyridinium chloride; CPC

---

Section 2 - COMPOSITION, INFORMATION ON INGREDIENTS

CAS#	Chemical Name	content	EINECS#
123-03-5	Pyridinium, 1-hexadecyl-, chloride	>95	204-593-9

Hazard Symbols: T+ N
Risk Phrases: 25 26 36/37/38 50/53

---

Section 3 - HAZARDS IDENTIFICATION
EMERGENCY OVERVIEW
Toxic if swallowed. Very toxic by inhalation. Irritating to eyes, respiratory system and skin. Very toxic to aquatic organisms, may cause long-term adverse effects in the aquatic environment.
Potential Health Effects
Eye:
Contact with eyes may cause severe irritation, and possible eye burns.
Skin:
Causes skin irritation. May be harmful if absorbed through the skin.
Ingestion:
Harmful if swallowed. May cause irritation of the digestive tract.
Inhalation:
May be fatal if inhaled. Dust is irritating to the respiratory tract.
Chronic:
No information found.

---

Section 4 - FIRST AID MEASURES
Eyes: In case of contact, immediately flush eyes with plenty of water for at least 15 minutes. Get medical aid immediately.
Skin:
In case of contact, immediately flush skin with plenty of water.
Remove contaminated clothing and shoes. Get medical aid. Wash clothing before reuse.
Ingestion:
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:
POISON material. If inhaled, get medical aid immediately. Remove victim to fresh air. If not breathing, give artificial respiration.
If breathing is difficult, give oxygen.
Notes to Physician:

---

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. This material in sufficient quantity and reduced particle size is capable of creating a dust explosion. Runoff from fire control or dilution water may cause pollution.
Extinguishing Media:
Use water spray, dry chemical, carbon dioxide, or appropriate foam.

---

Section 6 - ACCIDENTAL RELEASE MEASURES
General Information: Use proper personal protective equipment as indicated in Section 8.
Spills/Leaks:
Vacuum or sweep up material and place into a suitable disposal container. Avoid runoff into storm sewers and ditches which lead to waterways. Clean up spills immediately, observing precautions in the Protective Equipment section. Avoid generating dusty conditions.
Provide ventilation. Evacuate unnecessary personnel. Approach spill from upwind.

---

Section 7 - HANDLING and STORAGE
Handling:
Wash thoroughly after handling. Remove contaminated clothing and wash before reuse. Do not get in eyes, on skin, or on clothing. Keep container tightly closed. Do not breathe dust. Do not breathe spray or mist. Use only with adequate ventilation or respiratory protection.
Storage:
Keep container closed when not in use. Store in a tightly closed container. Store in a cool, dry, well-ventilated area away from incompatible substances.

---

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# 123-03-5: 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.

---

Section 9 - PHYSICAL AND CHEMICAL PROPERTIES

Physical State: Powder
Color: white
Odor: characteristic odor
pH: 5.2 (10g/l H2O)
Vapor Pressure: Not available.
Viscosity: Not available.
Boiling Point: Not available.
Freezing/Melting Point: 77 deg C
Autoignition Temperature: Not available.
Flash Point: Not available.
Explosion Limits, lower: Not available.
Explosion Limits, upper: Not available.
Decomposition Temperature: 234 deg C
Solubility in water: Soluble.
Specific Gravity/Density:
Molecular Formula: C21H38ClN
Molecular Weight: 339.98

---

Section 10 - STABILITY AND REACTIVITY
Chemical Stability:
Stable under normal temperatures and pressures.
Conditions to Avoid:
Dust generation, confined spaces.
Incompatibilities with Other Materials:
Strong oxidizing agents.
Hazardous Decomposition Products:
Hydrogen chloride, nitrogen oxides, carbon monoxide, carbon dioxide.
Hazardous Polymerization: Has not been reported

---

Section 11 - TOXICOLOGICAL INFORMATION
RTECS#:
CAS# 123-03-5: UU4900000 LD50/LC50:
CAS# 123-03-5: Draize test, rabbit, eye: 1%; Draize test, rabbit, eye: 100 mg; Draize test, rabbit, skin: 50 mg/24H Moderate; Inhalation, rat: LC50 = 90 mg/m3/4H; Oral, mouse: LD50 = 108 mg/kg; Oral, rabbit: LD50 = 400 mg/kg; Oral, rat: LD50 = 200 mg/kg.
Sensitization test (guinea pig): negative.
Carcinogenicity:
Pyridinium, 1-hexadecyl-, chloride - Not listed by ACGIH, IARC, or NTP.
Other:
See actual entry in RTECS for complete information.

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Section 12 - ECOLOGICAL INFORMATION
Ecotoxicity:
Fish: Carp: 0.01 mg/l; 96 h; LC50

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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: Toxic Solid, Organic, N.O.S.
Hazard Class: 6.1
UN Number: 2811
Packing Group: I
IMO
Shipping Name: Toxic Solid, Organic, N.O.S.
Hazard Class: 6.1
UN Number: 2811
Packing Group: I
RID/ADR
Shipping Name: Toxic Solid, Organic, N.O.S.
Hazard Class: 6.1
UN Number: 2811
Packing group: I

---

Section 15 - REGULATORY INFORMATION

European/International Regulations
European Labeling in Accordance with EC Directives
Hazard Symbols: T+ N
Risk Phrases:
R 25 Toxic if swallowed.
R 26 Very toxic by inhalation.
R 36/37/38 Irritating to eyes, respiratory system
and skin.
R 50/53 Very toxic to aquatic organisms, may cause
long-term adverse effects in the aquatic environment.
Safety Phrases:
S 26 In case of contact with eyes, rinse immediately
with plenty of water and seek medical advice.
S 28A After contact with skin, wash immediately with
plenty of water.
S 36/37 Wear suitable protective clothing and
gloves.
S 45 In case of accident or if you feel unwell, seek
medical advice immediately (show the label where
possible).
S 61 Avoid release to the environment. Refer to
special instructions/safety data sheets.
WGK (Water Danger/Protection)
CAS# 123-03-5: 3
Canada
CAS# 123-03-5 is listed on Canada's DSL List.
CAS# 123-03-5 is not listed on Canada's Ingredient Disclosure List.
US FEDERAL
TSCA
CAS# 123-03-5 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

氯化十六烷基吡啶是一种阳离子季铵化合物，在日常生活中也是一种重要的表面活性剂和杀菌剂。与十二烷基二甲基苄基氯化铵、十二烷基二甲基苄基溴化铵及其他常用的季铵盐杀菌剂相比，它在同等使用条件下对异养菌、铁细菌和硫酸盐还原菌的杀灭率更优。

生物活性

Cetylpyridinium chloride（CPC）作为一种阳离子季铵化合物，可用作口咽消毒剂。作为抗菌漱口水的有效成分，CPC具有广谱抗菌性，并能快速杀死革兰氏阳性菌，特别是对酵母有较好的杀菌作用。使用0.05%的CPC作为漱口水时，细菌数量会立即从2.0 log步骤减少至2.5 log步骤（即99%以上的杀灭）。1小时后，细菌数量恢复到1 log步骤（即约90%），但仍显著低于初始水平。

CPC能够抑制牙菌斑的形成，从而减少牙龈炎的发生。与洗必泰相比，CPC具有较低的残留效应，因此对牙菌斑和牙龈炎的影响也较小。此外，CPC对口咽念珠菌病有确切疗效。在牙科诊所中使用CPC漱口水可以显著减少传染性气雾剂，从而保护工作人员和病人。即使长时间（长达6周）使用CPC也不会干扰口腔内菌群的平衡。

危害

十六烷基氯化吡啶可能在皮肤中诱发过敏反应，并对眼睛具有刺激作用。作为季铵化合物，它在摄入浓缩溶液时可能会表现出类似箭毒的作用；受试患者可能出现高铁血红蛋白血症和溶血症状，并可能在1-3小时内死亡。此外，肝功能检查会升高，浓度过高的溶液可能导致灼伤。

因此，十六烷基氯化吡啶对人体有一定的危害性，必须严格控制剂量以确保安全。作为湿巾抗菌剂（防腐剂）的成分时，需要更加注意用量。台湾的相关标准规定：用于冲洗后的产品中，限量为5.0%；用于接触黏膜部位的产品中，限量为0.01%。这款产品的浓度为0.02%，并不用于清洁口腔内部，因此处于安全范围内。

体内研究

Cetylpyridinium chloride增加了严重的过敏反应风险，如嘴、脸、嘴唇或舌头肿胀、呼吸困难、皮疹和荨麻疹等。摄入高浓度的Cetylpyridinium chloride可能导致肺损伤。如果被吞食或吸入，则具有毒性。

用途

消毒防腐药。

生产方法

在48毫升SOCl₂ 和0.3克HCON(CH₃)₂ 的混合物中，控制温度为30-35℃下搅拌并滴入81克十六醇。滴毕后，将混合物煮沸30分钟，冷却后蒸馏得138-140℃（压力270帕）的馏分，收率为92.2%。

将80克氯代十六烷和32克干吡啶油浴加热至150-160℃反应12-15小时。反应完毕后加入80毫升干丙酮，混合物在水浴中溶解冷却得994%收率的产品。熔点为87-88℃。

类别

农药

毒性分级

高毒

急性毒性

口服 - 大鼠 LD₅₀: 200毫克/公斤；口服 - 小鼠 LD₅₀: 108毫克/公斤

刺激数据

皮肤 - 兔子 50毫克/24小时 中度；眼睛 - 兔子 100毫克 中度

可燃性危险特性

热分解释放有毒氮氧化物和氯化物烟雾

储运特性

低温、通风干燥库房存储

灭火剂

水、二氧化碳、泡沫、干粉

反应信息

• 作为反应物：
  描述：

  氯化十六烷基吡啶 在 碘 作用下， 以 氯仿 为溶剂， 以70%的产率得到
  参考文献：
  名称：

  Shilov; Kazheva; D'yachenko, Russian Journal of Physical Chemistry, 2002, vol. 76, # 8, p. 1295 - 1301

  摘要：

  DOI：
• 作为产物：
  描述：

  4-(4-Dimethylamino-phenylazo)-benzenesulfonate1-hexadecyl-pyridinium; 在 sodium chloride 作用下， 生成 氯化十六烷基吡啶 、 methyl orange
  参考文献：
  名称：

  甲基橙与亚胶束阳离子表面活性剂的相互作用

  摘要：

  已经研究了水性甲基橙 (MO)（一种偶氮染料）与亚胶束浓度范围内的烷基三甲基铵和 N-十六烷基吡啶鎓卤化物表面活性剂的相互作用。相互作用产生了一个新的 MO 吸收带，最大值为约。370 nm，新带的出现归因于水结构中发色团微环境的变化，使染料与亚胶束阳离子表面活性剂紧密堆积离子对。相互作用的强度取决于表面活性剂的烷基链长度、表面活性剂头基和反离子。

  DOI：

  10.1246/bcsj.66.2457
• 作为试剂：
  描述：

  甘露醇 在 cerium(IV) 、 硫酸 、 氯化十六烷基吡啶 作用下， 以 水 为溶剂， 生成 D-甘露糖
  参考文献：
  名称：

  铈(IV)在水胶束硫酸介质中氧化D-山梨醇和D-甘露醇的动力学及机理研究

  摘要：

  己糖醇（即 D-山梨糖醇和 D-甘露糖醇）在硫酸水溶液介质中在存在和不存在表面活性剂的情况下氧化铈 (IV) 的动力学和机制进行了研究。在动力学条件下，[S]T ≫ [Ce(IV)]T，其中 [S]T 是总底物（D-山梨糖醇或 D-甘露醇）浓度，整个过程显示出对 [Ce] 的一级依赖性(IV)]T 和 [S]T。该过程由 [HSO] 酸催化和抑制。根据 [HSO] 依赖性，已经发现 Ce(SO4)2+ 和 Ce(SO4)2 都具有动力学活性。已经用活化参数估计了存在和不存在表面活性剂时的不同速率常数。已发现氯化 N-十六烷基吡啶鎓可延缓己糖醇的氧化过程，而已发现十二烷基硫酸钠可加速该速率过程。所有这些发现（包括胶束效应）都已根据所提出的反应机制和动力学活性不同种类的 Ce(IV) 在水相和假胶束相之间的分配行为进行了解释。© 2008 Wiley Periodicals, Inc. 40:

  DOI：

  10.1002/kin.20332

文献信息

• [EN] PHENOTHIAZINE DERIVATIVES AND USES THEREOF<br/>[FR] DÉRIVÉS DE PHÉNOTHIAZINE ET LEURS UTILISATIONS
  申请人：CAMP4 THERAPEUTICS CORP

  公开号：WO2019195789A1

  公开（公告）日：2019-10-10

  The present invention provides phenothiazine compounds, processes for their preparation, pharmaceutical compositions comprising the compounds, and the use of the compounds or the compositions in the treatment of various diseases or conditions, for example ribosomal disorders and ribosomopathies, e.g. Diamond Blackfan anemia (DBA).

  本发明提供了吩噻嗪化合物，其制备方法，包含该化合物的药物组合物，以及在治疗各种疾病或症状中使用该化合物或组合物，例如核糖体紊乱和核糖体病，例如钻石-布莱克范贫血（DBA）。
• [EN] N-OPTIONALLY SUBSTITUTED ARYL-2-OLIGOMER-3-ALKOXYPROPIONAMIDES<br/>[FR] ARYL-2-OLIGOMÈRE-3-ALCOXYPROPIONAMIDES ÉVENTUELLEMENT SUBSTITUÉS EN N
  申请人：NEKTAR THERAPEUTICS

  公开号：WO2012051551A1

  公开（公告）日：2012-04-19

  The invention relates to (among other things) N-optionally substituted aryl- 2-oligomer-3-alkoxypropionamides and compositions comprising the same. A compound of the invention, when administered by any of a number of administration routes, exhibits one or more advantages over corresponding compounds lacking the oligomer.

  这项发明涉及（其他事项之一）N-选择性取代芳基-2-寡聚体-3-烷氧基丙酰胺和包含其的组合物。根据本发明的化合物，当通过多种给药途径之一给予时，表现出比缺乏寡聚体的相应化合物更多的优点。
• [EN] NEW CATIONIC DYES, KITS AND COMPOSITIONS THEREOF, AND PROCESS FOR DYEING KERATIN FIBERS<br/>[FR] NOUVEAUX COLORANTS CATIONIQUES, KITS ET COMPOSITIONS LES CONTENANT, ET PROCÉDÉ DE TEINTURE DE FIBRES KÉRATINIQUES
  申请人：ALFA PARF GROUP S P A

  公开号：WO2014202150A1

  公开（公告）日：2014-12-24

  The present invention relates to new cationic dyes of general formula (I) and (II): The invention also relates to kits and compositions for dyeing keratin fibers, which contain at least one of these dyes as well as to a process for dyeing keratin fibers using at least one of these dyes.

  本发明涉及一般式(I)和(II)的新阳离子染料：该发明还涉及用于染色角蛋白纤维的套件和组合物，其中至少含有这些染料之一，以及使用至少一种这些染料染色角蛋白纤维的方法。
• [EN] PRMT5 INHIBITORS CONTAINING A DIHYDRO- OR TETRAHYDROISOQUINOLINE AND USES THEREOF<br/>[FR] INHIBITEURS DE LA PRMT5 CONTENANT UNE DIHYDRO- OU TÉTRAHYDRO-ISOQUINOLÉINE ET LEURS UTILISATIONS
  申请人：EPIZYME INC

  公开号：WO2014100730A1

  公开（公告）日：2014-06-26

  Described herein are compounds of Formula (A), pharmaceutically acceptable salts thereof, and pharmaceutical compositions thereof. Compounds of the present invention are useful for inhibiting PRMT5 activity. Methods of using the compounds for treating PRMT5- mediated disorders are also described.

  本文描述了式（A）的化合物，其药学上可接受的盐以及药物组合物。本发明的化合物对抑制PRMT5活性是有用的。还描述了利用这些化合物治疗PRMT5介导的疾病的方法。
• PRMT5 INHIBITORS AND USES THEREOF
  申请人：Duncan Kenneth W.

  公开号：US20190083482A1

  公开（公告）日：2019-03-21

  Described herein are compounds of Formula (I), pharmaceutically acceptable salts thereof, and pharmaceutical compositions thereof. Compounds of the present invention are useful for inhibiting PRMT5 activity. Methods of using the compounds for treating PRMT5-mediated disorders are also described.

  本文描述了式（I）的化合物，其药学上可接受的盐以及药物组合物。本发明的化合物对抑制PRMT5活性是有用的。还描述了利用这些化合物治疗PRMT5介导的疾病的方法。