(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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