(E)-Dimethyl fumarate 富马酸二甲酯

CAS 624-49-7 MFCD00064438

化学结构图

624-49-7
SMILES: COC(=O)C=CC(=O)OC

化学属性

Mol. FormulaC6H8O4
Mol. Weight144.13
Boiling Point192-193°C at 760 mmHg
Melting Point102-106°C
Density1.124
TSCAYes
Flash Point192-193°C

别名和识别编码

Chemical Name(E)-Dimethyl fumarate
CAS Number624-49-7
PubChem Substance ID87569871
EC Number210-849-0
Beilstein Registry Number2,741
MDL NumberMFCD00064438
Reaxys-RN774590
Merck Number4287
Synonym Dimethyl fumarate {LY} Dimethyl fumarate FUMARIC ACID DIMETHYL ESTER Fumaric Acid Dimethyl Ester Fumaric acid dimethyl ester Fumaric acid, dimethyl ester TIMTEC-BB SBB008222 dimethyl trans-butenedioate dimethyl fumarate dimethylesterkyselinyfumarove dimethyltrans-butenedioate fumaric acid dimethyl ester {} {LY} Dimethyl fumarate {} {} {LY} Dimethyl fumarate {} {} {} {LY} Dimethyl fumarate {} {} {} {} {LY} Dimethyl fumarate {} {} {} {} {} {LY} Dimethyl fumarate {} {} {} {} {} {} {LY} Dimethyl fumarate {} {} {} {} {} {} {} { {} {} {} {} {} {} {} {LY} Dimethyl fumarate {} {} {} {} {} {} {} {} {LY} Dimethyl fumarate {} {} {} {} {} {} {} {} {} { {} {} {} {} {} {} {} {} {} {LY} Dimethyl fumarate {} {} {} {} {} {} {} {} {} {} {LY} Dimethyl fumarate {} {} {} {} {} {} {} {} {} {} {} {LY} Dimethyl fumarate {} {} {} {} {} {} {} {} {}
Chemical Name Translation富马酸二甲酯
Wiswesser Line Notation1OV1U1VO1 -T
LabNetwork Molecule IDLN00239542
InChIInChI=1S/C6H8O4/c1-9-5(7)3-4-6(8)10-2/h3-4H,1-2H3/b4-3+
Canonical SMILESO=C(OC)/C=C/C(OC)=O
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分类

  • {Chemicalbook} 饲料添加剂: 饲料贮存添加剂
  • {SNA} Acids and Esters, Additional Standards, All Fungicides, Analytical Standards,
  • {SNA} Acids and Esters,
  • {uni_hamburg} no charge; ester; 1fragment
  • {SNA} Acids and Esters, Analytical Standards, Analytical/Chromatography, CRM for chromatography, Certified Reference Materials (CRMs), Organic CRMs Alphabetical, Organic CRMs TraceCERT
  • {SNA} Acids and Este
  • {SNA} Acids and Esters, Analytical Standards, Analytical/Chromatography, Certified Reference Materials (CRMs), Fluka CRMs for Chromatography (neats), Organic CRMs Alphabetical, Organic CRMs TraceCERT
  • Building Blocks, C6 to C7, Carbonyl Compounds, Chemical Synthesis, Esters, Organic Building Blocks

产品应用

  • DMF是国外80年代开发的新型防腐防霉剂，具有低毒高效，广谱抗菌、安全、化学稳定性好，作用时间长特点，可用作饲料及食品、饮料、农林产品、防霉剂。

相关文献及参考

  • [2]. Peng H, et al. Dimethyl fumarate inhibits dendritic cell maturation via nuclear factor κB (NF-κB) and extracellular signal-regulated kinase 1 and 2 (ERK1/2) and mitogen stress-activated kinase 1 (MSK1) signaling. J Biol Chem. 2012 Aug 10;287(33):28017-26.
  • [3]. Cross SA, et al. Dimethyl fumarate, an immune modulator and inducer of the antioxidant response, suppresses HIV replication and macrophage-mediated neurotoxicity: a novel candidate for HIV neuroprotection. J Immunol. 2011 Nov 15;187(10):5015-25.
  • [4]. Jing X, et al. Dimethyl fumarate attenuates 6-OHDA-induced neurotoxicity in SH-SY5Y cells and in animal model of Parkinson's disease by enhancing Nrf2 activity. Neuroscience. 2015 Feb 12;286:131-40
  • Beilstein:2,741
  • Short: II/27C
  • Short: III/38B
  • [1]. Xin Xie, et al. Dimethyl fumarate induces necroptosis in colon cancer cells through GSH depletion/ROS increase/MAPKs activation pathway. Br J Pharmacol. 2015 Aug;

安全信息

GHS Symbol
WGK Germany1
Hazard statements
  • H303 May be harmfully swallowed 吞食可能有害
  • H312 Harmful in contact with skin 皮肤接触有害
  • H315 Causes skin irritation 会刺激皮肤
  • H317 May cause an allergic skin reaction 可能导致皮肤过敏
  • H319 Causes serious eye irritation 严重刺激眼睛
  • H411 Toxictoaquaticlifewithlonglastingeffects 对水生生物有毒性并具有长期影响。
Personal Protective Equipment dust mask type N95 (US), Eyeshields, Gloves
Hazard Codes Xn
RTECSEM6125000
Precautionary statements
  • P261 Avoid breathing dust/fume/gas/mist/vapours/spray. 避免吸入粉尘/烟/气体/烟雾/蒸汽/喷雾。
  • P264 Wash hands thoroughly after handling. 处理后要彻底洗净双手。
  • P272 Contaminated work clothing should not be allowed out of the workplace. 污染的工作服不得带出工作场所。
  • P273 Avoid release to the environment. 避免释放到环境中。
  • P280 Wear protective gloves/protective clothing/eye protection/face protection. 戴防护手套/防护服/眼睛的保护物/面部保护物。
  • P302+P350
  • P302+P352
  • P302+P352+P312+P362+P364
  • P305+P351+P338
  • P305+P351+P338+P310
  • P312 Call a POISON CENTER or doctor/physician if you feel unwell. 如果你感觉不适，呼叫解毒中心或医生/医师。
  • P333+P313
  • P363 Wash contaminated clothing before reuse. 被污染的衣服洗净后方可重新使用。
  • P501 Dispose of contents/container to..… 处理内容物/容器.....
Signal word
Safety Statements
  • S36/37/39 Wear suitable protective clothing, gloves and eye/face protection 穿戴适当的防护服、手套和眼睛/面保护；
  • S26 In case of contact with eyes, rinse immediately with plenty of water and seek medical advice 眼睛接触后，立即用大量水冲洗并征求医生意见；
  • S36/37 Wear suitable protective clothing and gloves 穿戴适当的防护服和手套；
  • S60 This material and its container must be disposed of as hazardous waste 该物质及其容器必须作为危险废物处置；
Risk Statements
  • R41 Risk of serious damage to eyes 有严重损伤眼睛的危险
  • R38 Irritating to skin 刺激皮肤
  • R43 May cause sensitisation by skin contact 皮肤接触会产生过敏反应
  • R21 Harmful in contact with skin 与皮肤接触有害
  • R36/37/38 Irritating to eyes, respiratory system and skin 对眼睛、呼吸系统和皮肤有刺激性
  • R36/38 Irritating to eyes and skin 对眼睛和皮肤有刺激性
Storage condition 2-8°C {LY} 2-8°C {} {LY} 2-8°C {} {} {LY} 2-8°C {} {} {} {LY} 2-8°C {} {} {} {} {LY} 2-8°C {} {} {} {} {} {LY} 2-8°C {} {} {} {} {} {} {LY} 2-8°C {} {} {} {} {} {} {} {LY} 2-8°C {} {} {} {} {} {} {} {} {LY} 2-8°C {} {} {} {} {} {} {} {} {} {LY} 2-8°C {} {} {} {} {} {} {} {} {} {} {LY} 2-8°C {} {} {} {} {} {} {} {} {} {} {} {LY} 2-8°C {} {} {} {} {} {} {} {} {} {} {} {} {LY} 2-8°C {} {} {} {} {} {} {} {} {} {} {} {} {} {LY} 2-8°C {} {} {} {} {} {} {} {} {} {} {} {} {} {} {LY} 2-8°C {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {LY} 2-8°C {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {LY} 2-8°C {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {LY} 2-8°C {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {LY} 2-8°C {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} { {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {LY} 2-8°C {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} { 
TYPE OF TEST            : LC - Lethal concentration
ROUTE OF EXPOSURE       : Inhalation
SPECIES OBSERVED        : Rodent - mouse
DOSE/DURATION           : >3100 mg/m3/10M
TOXIC EFFECTS :
   Details of toxic effects not reported other than lethal dose value
REFERENCE :
   NDRC** National Defense Research Committee, Office of Scientific Research
   and Development, Progress Report.  Volume(issue)/page/year:
   NDCrc-132,Dec,1942

TYPE OF TEST            : LD50 - Lethal dose, 50 percent kill
ROUTE OF EXPOSURE       : Administration onto the skin
SPECIES OBSERVED        : Rodent - rabbit
DOSE/DURATION           : 1250 mg/kg
TOXIC EFFECTS :
   Details of toxic effects not reported other than lethal dose value
REFERENCE :
   AIHAAP American Industrial Hygiene Association Journal.  (AIHA, 475 Wolf
   Ledges Pkwy., Akron, OH 44311)  V.19-    1958-  Volume(issue)/page/year:
   30,470,1969

TYPE OF TEST            : LD50 - Lethal dose, 50 percent kill
ROUTE OF EXPOSURE       : Oral
SPECIES OBSERVED        : Rodent - rat
DOSE/DURATION           : 2240 mg/kg
TOXIC EFFECTS :
   Details of toxic effects not reported other than lethal dose value
REFERENCE :
   AIHAAP American Industrial Hygiene Association Journal.  (AIHA, 475 Wolf
   Ledges Pkwy., Akron, OH 44311)  V.19-    1958-  Volume(issue)/page/year:
   30,470,1969

其他信息

  • 富马酸二甲酯价格(试剂级):更新日期 产品编号 产品名称 包装 价格 2011/08/23 LA1040201 反丁烯二酸二甲酯;延胡索酸二甲酯 25g 231元 2011/04/16 F0069 富马酸二甲酯 Dimethyl Fumarate 25G 252元 2011/04/16 F0069 富马酸二甲酯 Dimethyl Fumarate 500G 1020元
  • 图谱信息:富马酸二甲酯(624-49-7)质谱(MS) 富马酸二甲酯(624-49-7)红外图谱(IR3) 富马酸二甲酯(624-49-7)核磁图( 1 HNMR) 富马酸二甲酯(624-49-7)红外图谱(IR1) 富马酸二甲酯(624-49-7)核磁图( 13 CNMR) 富马酸二甲酯(624-49-7)Raman光谱 富马酸二甲酯(624-49-7)红外图谱(IR2)
  • 上游原料:盐酸 --> 甲醇 --> 硫酸 --> 对甲苯磺酸 --> 三氯化铁 --> 马来酸酐 --> 丙酸 --> 浓盐酸 --> 富马酸 --> 马来酸 --> 糖醛 --> 磷钨酸 --> 树脂催化剂 --> 阳离子树脂 --> 富马酸酯
  • 方法一:（1）富马酸酯化法。直接以富马酸为原料，在催化剂存在下与甲醇一步合成DMF。催化剂有三氟化硼、六水氯化铁（FeCl3·6H2O）、硫酸或磷酸，收率高达92%。也可以阳离子树脂催化剂，采用催化精馏技术，于80-85℃下酯化反应5h。 （2）马来酸异构酯化法。马来酸与甲醇在催化剂作用下，异构化、酯化得到DMF，催化剂有HCl-H2SO4和磷钨酸。用HCl-H2SO4作催化剂时，反应实际分两步进行，即HCl催化异构化反应和H2SO4催化酯化反应。马来酸与浓盐酸、水一起回流30min，得到91%的富马酸；富马酸与甲醇、浓硫酸一起回流12h，得到91.9%的产品。磷钨酸时复合催化剂，同时催化异构化和酯化反应。马来酸与甲醇，在磷钨酸存在下，回流4h，得89.4%的产品。(3)糖醛氧化酯化法。以糖醛为原料，合成分两步进行。首先糖醛在V2O5催化下用KClO3氧化成富马酸，反应温度95℃-105℃，反应时间7h，收率81.5%；然后富马酸在浓硫酸存在下，与甲醇一起加热回流，得到DMF，反应时间10h。收率86.0%。（4）马来酸酐水解异构酯化法。以马来酸酐为原料，与甲醇在催化剂作用下生成DMF。催化剂有浓盐酸、盐酸-磷酸、六水氯化铁、对甲基苯磺酸和硫脲。盐酸-磷酸属于复合催化剂，首先发生水解、酯化反应，得到马来酸二甲酯，后者再在溴与光存在下异构化才得到产品；用硫脲做催化剂，马来酸酐首先发生水解异构化反应得到富马酸，后者在硫酸存在下酯化得到产品。 实例：在100mL烧瓶中加入9.8g(0.1mol)马来酸酐、8.1mL（0.2mol）甲醇、0.5mL浓演算，加热回流1.5h。然后滴加12Ml（0.3mol）过量甲醇，0.5h滴完后，继续回流2h。反应结束后蒸出甲醇，稍冷后加入30mL乙醇，加热使固体溶解，冷却后析出晶体。两次产品分别用乙醇、水重结晶一次，得产品12.3g，产率86.2%
  • 防霉剂:富马酸二甲酯是一种新的气氛型防霉剂。常温下为白色粉末状结晶，熔点102～104℃，比重1.37，微溶于水，能溶 于乙酸乙酯、氯仿和醇，具有升华性，低毒，大鼠口服50=2628mg/kg，最大无作用剂量50mg/kg，具有广普、高效、 低毒、价廉等特点，除具有良好的抑菌杀菌作用外还兼有杀虫作用。具有接触杀菌和熏蒸杀菌双重作用。本品使用 安全性极高，人畜代谢后无残留。若干实例证明，富马酸二甲酯能透过皮肤接触，引致人体皮肤灼痛或过敏等严重 反应。此外，本品亦带有刺激性，应避免接触眼睛。 应用范围： 食品防霉。DMF用于面包、月饼、蛋糕等食品防霉、保鲜效果好。用量仅为0.05%。 粮食贮存。将适量的DMF直接加入大米、面粉中，保鲜期达200天以上，还能将粮食中的赤似谷盗、玉米象、谷蠹、 长角谷盗等杀死，保证粮食贮藏质量。 饲料防霉。如以DMF为主配制的降霉王就是高效饲料防霉剂。 水果防腐保鲜，尤其对柑橘效果突出。 蚕茧防霉。 衣物防霉防蛀。
  • 具有酯香味。易升华，微溶于水，溶于乙醇。对光和热稳定,在紫外线和阳光照射下基本上72小时无变化,110℃加热2小时不分解。 作用机理：能顺利穿透微生物的细胞膜，抑制微生物细胞的分裂，并通过对三羧酸循环（TCAC）磷酸己糖途径（HMP）和酵解途径（EMP）的酶活性的抑制来抑制微生物的呼吸作用，从而达到抑菌作用，使微生物的生长繁殖被有效控制。
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系列性分类

  1. Analytical & Chromatography 分析化学与色谱
  2. Analytical Standards
  3. Alphabetic - Analytical Standards
  4. D - Alphabetic
  5. DID - DIN - D
  1. Chemical Synthesis 化学合成
  2. Building Blocks 合成砌块
  3. Organic Building Blocks 有机砌块
  4. Carbonyl Compounds 羰基化合物
  5. Esters - Carbonyl Compounds
  1. Chemical Synthesis 化学合成
  2. Building Blocks 合成砌块
  3. Organic Building Blocks 有机砌块
  4. Carbonyl Compounds 羰基化合物
  5. Esters - Carbonyl Compounds
  6. C6 to C7 - Esters
  1. Analytical & Chromatography 分析化学与色谱
  2. Analytical Standards
  3. Certified Reference Materials (CRMs) - Analytical Standards
  4. Organic CRMs TraceCERT - Certified Reference Materials (CRMs)
  5. CRM for chromatography - Organic CRMs TraceCERT
  6. Organic CRMs Alphabetical - CRM for chromatography
  1. Chemical Synthesis 化学合成
  2. Building Blocks 合成砌块
  3. Organic Building Blocks 有机砌块
  4. Carbonyl Compounds 羰基化合物
  5. Esters
  6. C2 to C5
  1. Medical Research Areas
  2. Metabolism
  3. Reactive Oxygen Species  (活性氧)
  1. Medical Research Areas
  2. Metabolism
  3. Endogenous Metabolite  (内源性代谢物)

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