氯苯甘醚 | 104-29-0

• 物质功能分类: 原料药 - 人工合成抗感染类药 - 抗真菌类药
• 分子结构分类: 有机化合物 - 苯类化合物 - 苯酚醚
• 中文名称: 氯苯甘醚
• 中文别名: 3-对氯苯氧基-1,2-丙二醇；3-(4-氯苯氧基)-1,2-丙二醇；氯苯、一氯代苯；氯酚醚；氯苯甘油醚
• 英文名称: chlorphenesin
• 英文别名: 3-(4-chlorophenoxy)-1,2-propanediol；3-(4-chlorophenoxy)propane-1,2-diol
• CAS: 104-29-0
• 化学式: C₉H₁₁ClO₃
• mdl: MFCD00021990
• 分子量: 202.638
• InChiKey: MXOAEAUPQDYUQM-UHFFFAOYSA-N

物化性质

• 熔点：
  77-79°C
• 沸点：
  290.96°C (rough estimate)
• 密度：
  1.2411 (rough estimate)
• 溶解度：
  可溶于DMSO（轻微）、乙醇（轻微）、甲醇（轻微、超声处理）
• LogP：
  1.23 at 23℃
• 物理描述：
  Solid
• 稳定性/保质期：
  避免与氧化物接触。

计算性质

• 辛醇/水分配系数(LogP)：
  1.2
• 重原子数：
  13
• 可旋转键数：
  4
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.333
• 拓扑面积：
  49.7
• 氢给体数：
  2
• 氢受体数：
  3

ADMET

代谢

肝脏的。85%的剂量在24小时内以葡萄糖醛酸代谢物的形式排出。

Hepatic. 85% of a dose excreted within 24 hours as the glucuronide metabolite.

来源:DrugBank

吸收、分配和排泄

• 吸收

快速而完整。

Rapid and complete.

来源:DrugBank

安全信息

• 安全说明：
  S26,S36
• 危险类别码：
  R20/21/22
• 海关编码：
  2909499000
• 危险品运输编号：
  OTH
• 危险性防范说明：
  P261,P280,P305+P351+P338
• 危险性描述：
  H302,H312,H315,H319,H332,H335
• 储存条件：
  储存于阴凉、通风的库房中。远离火种、热源和水源，并保持容器密封。应与氧化剂和还原剂分开存放，切忌混储。配备相应品种和数量的消防器材。储区应备有合适的材料以收容泄漏物。

SDS

Material Safety Data Sheet

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Section 1. Identification of the substance
Chlorphenesin
Product Name:
Synonyms: 3-(4-Chlorophenoxy)-1,2-Propanediol

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Section 2. Hazards identification
Harmful by inhalation, in contact with skin, and if swallowed.
H315: Causes skin irritation
H319: Causes serious eye irritation
H335: May cause respiratory irritation
P261: Avoid breathing dust/fume/gas/mist/vapours/spray
Wear protective gloves/protective clothing/eye protection/face protection
P280:
P305+P351+P338: IF IN EYES: Rinse cautiously with water for several minutes. Remove contact lenses if present
and easy to do – continue rinsing
P304+P340: IF INHALED: Remove victim to fresh air and keep at rest in a position comfortable for breathing
P405: Store locked up

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Section 3. Composition/information on ingredients.
Chlorphenesin
Ingredient name:
CAS number: 104-29-0

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Section 4. First aid measures
Immediately wash skin with copious amounts of water for at least 15 minutes while removing
Skin contact:
contaminated clothing and shoes. If irritation persists, seek medical attention.
Eye contact: Immediately wash skin with copious amounts of water for at least 15 minutes. Assure adequate
flushing of the eyes by separating the eyelids with fingers. If irritation persists, seek medical
attention.
Inhalation: Remove to fresh air. In severe cases or if symptoms persist, seek medical attention.
Wash out mouth with copious amounts of water for at least 15 minutes. Seek medical attention.
Ingestion:

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Section 5. Fire fighting measures
In the event of a fire involving this material, alone or in combination with other materials, use dry
powder or carbon dioxide extinguishers. Protective clothing and self-contained breathing apparatus
should be worn.

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Section 6. Accidental release measures
Personal precautions: Wear suitable personal protective equipment which performs satisfactorily and meets local/state/national
standards.
Respiratory precaution: Wear approved mask/respirator
Hand precaution: Wear suitable gloves/gauntlets
Skin protection: Wear suitable protective clothing
Eye protection: Wear suitable eye protection
Methods for cleaning up: Mix with sand or similar inert absorbent material, sweep up and keep in a tightly closed container
for disposal. See section 12.
Environmental precautions: Do not allow material to enter drains or water courses.

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Section 7. Handling and storage
Handling: This product should be handled only by, or under the close supervision of, those properly qualified
in the handling and use of potentially hazardous chemicals, who should take into account the fire,
health and chemical hazard data given on this sheet.
Storage: Store in closed vessels.

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Section 8. Exposure Controls / Personal protection
Engineering Controls: Use only in a chemical fume hood.
Personal protective equipment: Wear laboratory clothing, chemical-resistant gloves and safety goggles.
General hydiene measures: Wash thoroughly after handling. Wash contaminated clothing before reuse.

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Section 9. Physical and chemical properties
Not specified
Appearance:
Boiling point: No data
Melting point: No data
Flash point: No data
Density: No data
Molecular formula: C9H11ClO3
Molecular weight: 202.6

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Section 10. Stability and reactivity
Conditions to avoid: Heat, flames and sparks.
Materials to avoid: Oxidizing agents.
Possible hazardous combustion products: Carbon monoxide, hydrogen chloride.

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Section 11. Toxicological information
No data.

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Section 12. Ecological information
No data.

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Section 13. Disposal consideration
Arrange disposal as special waste, by licensed disposal company, in consultation with local waste
disposal authority, in accordance with national and regional regulations.

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Section 14. Transportation information
Non-harzardous for air and ground transportation.

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Section 15. Regulatory information
No chemicals in this material are subject to the reporting requirements of SARA Title III, Section
302, or have known CAS numbers that exceed the threshold reporting levels established by SARA
Title III, Section 313.

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SECTION 16 - ADDITIONAL INFORMATION
N/A

制备方法与用途

氯苯甘醚简介

氯苯甘醚是一种防腐剂，广泛应用于化妆品中。它与大多数防腐剂兼容，如山梨酸钾、苯甲酸钠、甲基异噻唑啉酮等。这种白色晶体通常具有轻微的特征性气味，熔点在77.0-80.5℃之间。氯苯甘醚微溶于水（约0.5%），在95%乙醇中的溶解度为5%，并能溶解于醚类中。它微溶于不挥发油，而不溶于白矿油。

微生物控制性能

这种防腐剂能够提供出色的广谱抗菌活性，对革兰氏阳性菌（G+）、革兰氏阴性菌（G-）、黑曲霉菌、嗜松青霉、白色念珠菌以及酿酒酵母均有抑制和杀灭能力。

用途 欧洲

欧洲自1996年起允许将氯苯甘醚作为防腐剂用于化妆品中。

日本与美国

日本和美国也批准了这种成分的使用。

复合应用

氯苯甘醚对真菌更为有效，与其他防腐剂配合使用时能显著增强防腐效果。

应用领域 化妆品

氯苯甘醚作为防腐剂主要用于化妆品中。它能够防止各种问题，如粘度改变、pH变化、乳化不稳定、微生物生长、颜色变化和难闻气味的产生。此外，它还常用于面部保湿霜、抗衰老精华液、防晒霜、粉底液、眼霜、洁面乳、睫毛膏以及遮瑕膏中。

医药

氯苯甘醚相关制剂为抑制IgE介导的组胺释放的免疫抑制剂，同时也是一种抗真菌药物。它适用于治疗抗真菌、细菌、阴道霉菌和毛滴虫病症，并具有多种剂型。

抗微生物活性

在化妆品方面，氯苯甘醚被用作杀菌剂。这种防腐剂对革兰氏阳性菌及阴性菌表现出较强的杀菌作用，特别是对黑曲霉IML149007和嗜松青霉IMI87160（真菌）有显著效果，并且能够有效抑制白色念珠菌NCPF3179和酿酒酵母NCPF3275（酵母）的生长。

生物活性

体外研究 氯苯甘醚在不同浓度下对人类泪腺上皮细胞系(HMGECs)的作用表现出剂量依赖性。具体表现在：

• 0.01%，0.1%和0.3%的浓度暴露30分钟后，显著降低了Akt信号通路的活性。
• 在24小时培养后，0.1%和0.3%的浓度导致IHMGECs（人永生化泪腺上皮细胞）出现皱缩、萎缩、黏附不良以及脱落，并且减少了IHMGEC的数量。

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
  4-氯苯基缩水甘油醚	4-chlorophenyl 2,3-epoxypropyl ether	2212-05-7	C9H9ClO2	184.622
  氯苯氨酸甘油酯	chlorphenesin carbamate	886-74-8	C10H12ClNO4	245.663
  ——	3-(p-chlorophenoxy)-1,2-propanediol-2-carbamate	61514-96-3	C10H12ClNO4	245.663
  ——	4-((4-chlorophenoxy)methyl)-2,2-dimethyl-1,3-dioxolane	——	C12H15ClO3	242.702

• 下游产品

  中文名称	英文名称	CAS号	化学式	分子量
  1,2-丙二醇,3-(4-氯苯氧基)-,(2R)-	(R)-3-(4-chlorophenoxy)propane-1,2-diol	112652-61-6	C9H11ClO3	202.638
  ——	(S)-3-(4-chlorophenoxy)propane-1,2-diol	80117-05-1	C9H11ClO3	202.638
  1-氯-3-(4-氯苯氧基)丙-2-醇	1-chloro-3-(4-chloro-phenoxy)-propan-2-ol	39735-79-0	C9H10Cl2O2	221.083
  1-苯氧基-丙醇	1-phenoxy-2-propanol	770-35-4	C9H12O2	152.193
  ——	3-(4-chloro-2-hydroxyphenoxy)propane-1,2-diol	——	C9H11ClO4	218.637
  ——	p-chlorophenoxyacetaldehyde	43018-72-0	C8H7ClO2	170.595
  ——	4-((4-chlorophenoxy)methyl)-1,3-dioxolan-2-one	40492-32-8	C10H9ClO4	228.632
  ——	1-O-vinylsuccinyl-chlorphenesin	935477-90-0	C15H17ClO6	328.749
  ——	1-O-vinyladipoyl-chlorphenesin	——	C17H21ClO6	356.803
  ——	1-O-vinylazeloyl-chlorphenesin	——	C20H27ClO6	398.884

反应信息

• 作为反应物：
  描述：

  氯苯甘醚 在 sodium periodate 、 silica gel 作用下， 以 二氯甲烷 为溶剂， 反应 0.25h， 以90%的产率得到p-chlorophenoxyacetaldehyde
  参考文献：
  名称：

  A New and Efficient Heterogeneous System for the Oxidative Cleavage of 1,2-Diols and the Oxidation of Hydroquinones

  摘要：

  碘酸钠/湿硅胶在二氯甲烷存在下是一种有效的试剂，用于1,2-二醇的氧化裂解和对苯二酚的氧化。该试剂易于制备，是经典亚碘酸氧化的良好替代品，特别适用于易形成水合物的醛类化合物的制备。

  DOI：

  10.1055/s-1989-27155
• 作为产物：
  描述：

  4-氯苯酚钾 在 palladium on activated charcoal 盐酸 、 氢气 作用下， 以 异丙醇 、 苯 为溶剂， 生成 氯苯甘醚
  参考文献：
  名称：

  环状亚硫酸盐和磷酸盐通过弱酸盐发生的置换反应，适用于磷脂和其他天然物质的合成。

  摘要：

  DOI：

  10.1021/jo00433a016

文献信息

• Naphthyloxy acetic acid derivatives and a pharmaceutical composition comprising them as an active ingredient
  申请人：Ono Pharmaceutical Co., Ltd.

  公开号：US06335366B2

  公开（公告）日：2002-01-01

  The naphthyloxyacetic acid derivatives of the formula (I) wherein A is H, -(alkylene)COOR1, -(alkylene)CONR2R3, -(alkylene)OH, -(alkylene)tetrazole, -(alkylene)CN; E is single bond or alkylene; G is —S—, —SO—, —SO2—, —O— or —NR4—; L is alkylene, —(CH2)m—CH═CH—(CH2)n— or —(CH2)x—CH(OH)—(CH2)y—; M is phenyl, phenyl(thio, oxy, amino), diphenylmethyl, diphenylmethyl(thio, oxy, amino), and pharmaceutical composition comprising them as an active ingradient. The compounds of the formula (I) can combine PGE2 receptor and exhibit the activity to antagonize or agonize for PGE2 receptor. Therefore, they are useful as anti-hyperlipemia, for the prevention of abortion, for analgesics, as antidiarrheals, sleep inducer, diuretic, anti-diabetes, abortient, cathartics, antiulcer, anti-gastritis or antihypertensive etc.

  式(I)的萘氧乙酸衍生物 其中A为H，-(烷基)COOR1，-(烷基)CONR2R3，-(烷基)OH，-(烷基)四唑，-(烷基)CN；E为单键或烷基；G为—S—，—SO—，—SO2—，—O—或—NR4—；L为烷基，—(CH2)m—CH═CH—(CH2)n—或—(CH2)x—CH(OH)—(CH2)y—；M为苯基，苯基(硫、氧、氨基)，二苯甲基，二苯甲基(硫、氧、氨基)，以及包含它们作为活性成分的药物组合物。式(I)的化合物可以结合PGE2受体，并表现出对PGE2受体的拮抗或激动活性。因此，它们可用作抗高脂血症、预防流产、镇痛剂、止泻药、催眠剂、利尿剂、抗糖尿病药、引产剂、泻药、抗溃疡药、抗胃炎药或降压药等。
• [EN] ANTIBACTERIAL COMPOUNDS<br/>[FR] COMPOSÉS ANTIBACTÉRIENS
  申请人：MASSACHUSETTS GEN HOSPITAL

  公开号：WO2019199979A1

  公开（公告）日：2019-10-17

  The present application provides compounds of formula: Methods of using these compounds for killing bacterial growth and treating bacterial infections are also provided.

  本申请提供了以下化合物的公式：还提供了使用这些化合物杀灭细菌生长和治疗细菌感染的方法。
• Sulfamates as antiglaucoma agents
  申请人：A. H. Robins Company, Incorporated

  公开号：US05192785A1

  公开（公告）日：1993-03-09

  Sulfamate esters of the formula (HO).sub.p --A--[OSO.sub.2 NR.sup.1 R.sup.2 ].sub.z where A is aryloxyalkyl, p is the number of unreacted hydroxy groups present on the alkyl moiety and may be zero, z is the number of --OS(O).sub.2 NR.sup.1 R.sup.2 groups attached to carbons of the alkyl moiety and is always at least one; R.sup.1 and R.sup.2 are selected from hydrogen, loweralkyl, carboxy, and the like are useful in treating glaucoma.

  Sulfamate酯的化学式为(HO).sub.p --A--[OSO.sub.2 NR.sup.1 R.sup.2 ].sub.z，其中A为芳基氧烷基，p为烷基部分上存在的未反应羟基的数量，可以为零，z为连接到烷基部分碳上的--OS(O).sub.2 NR.sup.1 R.sup.2基团的数量，始终至少为一；R.sup.1和R.sup.2从氢、低烷基、羧基等中选择，在治疗青光眼方面是有用的。
• Nickel-Catalyzed Alkyl–Alkyl Cross-Electrophile Coupling Reaction of 1,3-Dimesylates for the Synthesis of Alkylcyclopropanes
  作者：Amberly B. Sanford、Taylor A. Thane、Tristan M. McGinnis、Pan-Pan Chen、Xin Hong、Elizabeth R. Jarvo

  DOI：10.1021/jacs.0c01330

  日期：2020.3.18

  3-diol derivatives. Notably, this transformation is utilized to synthesize a range of mono- and 1,2-disubstituted alkylcyclopropanes, including those derived from terpenes, steroids, and aldol products. Additionally, enantioenriched cyclopropanes are synthesized from the products of proline-catalyzed and Evans aldol reactions. A procedure for direct transformation of 1,3-diols to cyclopropanes is also

  两个 Csp3-X 键的交叉亲电偶联反应仍然具有挑战性。在此，我们报告了分子内镍催化的 1,3-二醇衍生物的交叉亲电偶联反应。值得注意的是，这种转化用于合成一系列单和 1,2-二取代的烷基环丙烷，包括衍生自萜烯、类固醇和醛醇产品的那些。此外，对映体富集的环丙烷是由脯氨酸催化和埃文斯羟醛反应的产物合成的。还描述了将 1,3-二醇直接转化为环丙烷的过程。计算和实验数据与镍催化机制一致，该机制始于二级中心的立体氧化加成。
• An Unusual (R)-Selective Epoxide Hydrolase with High Activity for Facile Preparation of Enantiopure Glycidyl Ethers
  作者：Jing Zhao、Yan-Yan Chu、Ai-Tao Li、Xin Ju、Xu-Dong Kong、Jiang Pan、Yun Tang、Jian-He Xu

  DOI：10.1002/adsc.201100031

  日期：2011.6

  ortho‐substituted phenyl glycidyl ethers and para‐nitrostyrene oxide. Worthy of note is that the substrate structure remarkably affected the enantioselectivities of the enzyme, as a reversed (S)‐enantiopreference was unexpectedly observed for the ortho‐nitrophenyl glycidyl ether. As a proof‐of‐concept, five enantiopure epoxides (>99% ee) were obtained in high yields, and a gram‐scale preparation of

  从巨大芽孢杆菌ECU1001中克隆了一种新的环氧水解酶（BMEH），该酶具有异常的（R）-对映体选择性和很高的活性。在对位取代的苯基缩水甘油醚和对硝基苯乙烯氧化物的生物拆分中，实现了最高的对映选择性（E > 200）。值得一提的是，底物结构显着影响了酶的对映选择性，因为人们意外地观察到邻硝基硝基苯缩水甘油醚的反向（S）-对映体选择性。作为概念验证，以高收率获得了五种对映纯环氧化合物（> 99％ee），并以克级制备了（S） -邻甲基苯基缩水甘油基醚，然后成功地在几个小时内完成，这表明BMEH为光学活性的环氧化物的高效制备有吸引力的生物催化剂。

表征谱图