Basic information
- CAS
2459-05-4- Standard SMILES
CCOC(=O)/C=C/C(=O)O- InChIKey
XLYMOEINVGRTEX-ONEGZZNKSA-N- Molecular formula
- C6H8O4
- Average molar mass
- 144.12 g/mol
- Monoisotopic mass
- 144.04225874
Names & identifiers
- Preferred name
- Monoethyl fumarate
- IUPAC
- (E)-4-ethoxy-4-oxobut-2-enoic acid
- English name
- Monoethyl fumarate
- Molecular formula
- C6H8O4
- Molecular weight
- 144.13
Names & synonyms
Monoethyl fumarate2459-05-4(E)-4-ethoxy-4-oxobut-2-enoic acidEthyl fumarateFumaric acid monoethyl esterFumaric acid, monoethyl esterY3W849NG2N2-Butenedioic acid (E)-, monoethyl esterDTXSID701021503NSC-524101ethylhydrogenfumarateRefChem:138931
Show more names
AKOS BBB/201EthylfumaratMonoethyl FuMeratemonoethyl furmarateETHYL ACID FUMARATERARECHEM AL BE 1505
DTXCID80209897219-544-7mono-Ethyl fumarateEthyl hydrogen fumarate(2E)-4-ethoxy-4-oxobut-2-enoic acidEthylhydrogenfumaratMFCD000026992-Butenedioic acid (2E)-, 1-ethyl ester
Database identifiers
- CAS
2459-05-4- PubChem CID
- 5358902
- DTXSID
DTXSID701021503- ChEMBL
CHEMBL1771637- UNII
- Y3W849NG2N
- EC Number
- 219-544-7
- Nikkaji
- J121.401B、J443.405F
Properties
Computed structural properties
- XLogP
- 0.2
- Topological polar surface area
- 63.6 Ų
- Hydrogen bond donors
- 1
- Hydrogen bond acceptors
- 4
- Rotatable bonds
- 4
- Heavy atoms
- 10
- Formal charge
- 0
- Complexity
- 159
Experimental & physicochemical properties
DrugsPharmaceuticals
Physicochemical properties
- Melting point
- 66 · 66-68 °C (lit.)
- Boiling point
- 147 °C/16 · 147 °C/16 mmHg (lit.)
- Density
- 1.1109 · 1.1109
- refractive index
- 1.45 · 1.4500 (estimate)
- storage temp.
- Refrigerator
- solubility
- Chloroform (Slightly), DMSO (Slightly), Methanol (Slightly)
- form
- Crystalline Powder
- pka
- 3.45 · 3.45±0.10(Predicted)
- color
- Almost white to beige
- Water Solubility
- Soluble in water.
- BRN
- 1723588 · 1723588
- Dielectric constant
- 6.5 · 6.5(23.0℃)
- InChI
- InChI=1S/C6H8O4/c1-2-10-6(9)4-3-5(7)8/h3-4H,2H2,1H3,(H,7,8)/b4-3+
- InChIKey
- XLYMOEINVGRTEX-ONEGZZNKSA-N
- SMILES
- C(OCC)(=O)/C=C/C(O)=O
- CAS DataBase Reference
- 2459 · 2459-05-4(CAS DataBase Reference)
- FDA UNII
- 3 W849NG2N · Y3W849NG2N
- NIST Chemistry Reference
- Ethyl hydrogen fumarate(2459-05-4)
- UNSPSC Code
- 41116107 · 41116107
- NACRES
- 24 · NA.24
- Symbol(GHS)
- 7 · GHS07
- Signal word
- Warning
- Hazard statements
- 315 · H315-H317-H319-H335
- Precautionary statements
- 280 · P280-P302+P352-P305+P351+P338
- target organs
- Respiratory system
- PPE
- 95 · dust mask type N95 (US), Eyeshields, Gloves
- Hazard Codes
- Xi
- Risk Statements
- 36 · 36/37/38
- Safety Statements
- 26 · 26-36
- WGK Germany
- 1 · 1
- HazardClass
- IRRITANT
- HS Code
- 29171900 · 29171900
- Storage Class
- 11 · 11 - Combustible Solids
- Hazard Classifications
- 2 Skin · Eye Irrit. 2Skin Irrit. 2Skin Sens. 1STOT SE 3
Safety & regulation
Safety information is for reference only and does not replace the supplier’s Safety Data Sheet (SDS), applicable regulations, or professional assessment.
GHS classification
GHS Classification
This chemical does not meet GHS hazard criteria for 2.1% (1 of 47) of reports.
Warning
H315 (97.9%): Causes skin irritation [Warning Skin corrosion/irritation]
P261, P264, P264+P265, P271, P280, P302+P352, P304+P340, P305+P351+P338, P319, P321, P332+P317, P337+P317, P362+P364, P403+P233, P405, and P501 (click each P-code to see the statement)
Aggregated GHS information provided per 47 reports by companies from 7 notifications to the ECHA C&L Inventory. Each notification may be associated with multiple companies.
Hazard information
Regulatory Information2-Butenedioic acid (2E)-, monoethyl ester: Does not have an individual approval but may be used as a component in a product covered by a group standard. It is not approved for use as a chemical in its own right.
Hazard Classes and CategoriesSkin Irrit. 2 (97.9%)
Safety data
- PPE
- dust mask type N95 (US), Eyeshields, Gloves
- wgk
- 1
- hs_code
- 29171900
- risk_code
- 36/37/38
- Signal word
- Warning
- Symbol(GHS)
- GHS07
- hazard_code
- Xi
- safety_code
- 26-36
- hazard_class
- IRRITANT
- Storage Class
- 11 - Combustible Solids
- target organs
- Respiratory system
- Hazard statements
- H315-H317-H319-H335
- Hazard Classifications
- Eye Irrit. 2Skin Irrit. 2Skin Sens. 1STOT SE 3
- Precautionary statements
- P280-P302+P352-P305+P351+P338
Chemistry & industry
Pharmacology
MeSH Pharmacological ClassificationDrugs used to treat or prevent skin disorders or for the routine care of skin.
Uses & manufacturing
UsesUse (kg; approx.) in Germany (2009): >1000
Applications
DescriptionMonoethyl fumarate is the Monoethyl ester form of fumarate. It is a kind of effective preservative and polymerization agent for macromolecular material. Monoethyl fumarate is capable of inhibiting the growth of bacteria, yeast and mold and prolonging the storage time of feed can. It can also be used for long-term systemic therapy in the treatment of psoriasis (a chronic hyperproliferative inflammatory skin disorder). It is the most active ingredient in the antipsoriasis drug Fumadem. The mechanism is likely to be related to its effect of improvement of keratinocyte differentiation and inhibition of keratinocyte proliferation. Monomethyl fumarate has beneficial effects on the inflamed blood–brain barrier. It increases levels of endogenous antioxidant proteins in brain endothelial cells and reduces expression of VCAM-1 in inflamed brain endothelial cells. Transendothelial monocyte migration is limited upon MMF treatment.
UsesMonoethyl fumarate is the monoethyl ester form of fumaric acid. Monoethyl fumarate is a kind of effective preservative and polymerization agent for macromolecular material.Monoethyl fumarate (fumaric acid monoethyl ester, monoethyl fumarate) was used in the preparation of photo-crosslinkable macromers. It was also used to synthesize Ugi/intramolecular Diels-Alder (IMDA) cycloaddition products.
Preparation methods
PreparationMonomethyl fumarate was synthesized by maleic anhydride and methanol. It is used to treat relapsing forms of multiple sclerosis in adults (including clinically isolated syndrome, relapsing-remitting disease, and active secondary progressive disease).
Upstream & downstream products
Upstream raw materials
Downstream products
Suppliers100 total
梯希爱(上海)化成工业发展有限公司021-67121386 · [email protected]
上海阿拉丁生化科技股份有限公司400-6206333 13167063860 · [email protected]
广州隽沐生物科技股份有限公司020-36607679; 13502246435 · [email protected]
武汉欣扬瑞和化学科技有限公司153-07155313 15307155313 · [email protected]
河北创海生物科技有限公司+86-86-13131129325 · [email protected]
爱斯特（成都）生物制药股份有限公司+86-28-85122536 85324413 · [email protected]
上海赫文斯化工有限公司15721252604 17321035817 · [email protected]
Dayang Chem (Hangzhou) Co.,Ltd.+86-0571-88938639 17705817739 · [email protected]
南京兰亚化工贸易有限公司+86-25-8331-5620 · [email protected]
Hebei Yanxi Chemical Co., Ltd.+86-17531190177 · [email protected]
上海迈瑞尔生化科技有限公司4006356688 18621169109 · [email protected]
阿法埃莎（中国）化学有限公司400-6106006 · [email protected]
安耐吉化学&3A（安徽泽升科技股份有限公司）400-0056266 · [email protected]
上海瀚鸿科技股份有限公司021-54306202 13764082696 · [email protected]
上海景颜化工科技有限公司13817811078 · [email protected]
嘉兴市艾森化工有限公司0573-85285100 18627885956 · [email protected]
合肥天健化工有限公司551-65418679 15856988503;15837135945 · [email protected]
BOC Sciences1-631-485-4226; 16314854226 · [email protected]
山东西亚化学有限公司13355009207 13355009207 · [email protected]
玛雅试剂+86 (573) 82222445 (0)18006601000 452520369 · [email protected]
四川库利南科技有限公司400-1166-196 18981987031 · [email protected]
天津希恩思生化科技有限公司400 638 7771 · [email protected]
艾科试剂4008-755-333 18080918076 · [email protected]
上海思域化工科技有限公司86-21-34053660 · [email protected]
赛默飞世尔科技（中国）有限公司800-810-5118 · [email protected]
TCI AMERICA800-4238616 · [email protected]
TOKYO CHEMICAL INDUSTRY CO., LTD.03-36680489 · [email protected]
TCI Europe320-37350700 · [email protected]
上海贤鼎生物科技有限公司4009209199 · [email protected]
深圳振强药物研发有限公司0755-66853366 13670046396 · [email protected]
上海睿升化工科技有限公司+86-021-50935922
惠州拓康生物科技有限公司+86 (0752) 222-7171, +86 15815821171
HBCChem, Inc.+1-510-219-6317 · [email protected]
日照力德士化工有限公司010-51268198 · [email protected]
美岚实业（上海）有限公司021-58958189 · [email protected]
成都零六生物科技有限公司400-1166-196 13458535857 · [email protected]
上海有朋化工有限公司021-69005955 13701776567 · [email protected]
北京海力扬化学科技有限公司13718199399 · [email protected]
北京欣赛维化学科技有限公司010-56218822 13717722232 · [email protected]
四川海诺威科技有限公司13708085536 13708085536 · [email protected]
上海凯赛化工有限公司021-33516722 13701817869 · [email protected]
上海彤源化工有限公司021-021-69182866 13701855675 · [email protected]
凯试（上海）科技有限公司021-50135380 · [email protected]
北京华扬致成科技有限公司13716033033 · [email protected]
上海蓝润化学有限公司021-69515658 ; 69515628 13701998368 · [email protected]
上海容立化学科技有限公司021-69992220 13701886816 · [email protected]
上海康拓化工有限公司021-69185552 13701777608 · [email protected]
湖北巨胜科技有限公司027-59599241 18871490274 · [email protected]
池州凯隆进出口贸易有限公司[email protected]
Sigma-Aldrich西格玛奥德里奇(上海)贸易有限公司021-61415566 800-8193336 · [email protected]
Additional notes
DefinitionChEBI: Monomethyl fumarate is a dicarboxylic acid monoester resulting from the formal condensation of one of the carboxy groups of fumaric acid with methanol. Is is a metabolite of dimethyl fumarate and used for the the treatment of patients with relapsing multiple sclerosis (MS). It also induces the NFE2L2 (Nrf2) transcription factor by binding to KEAP1. It has a role as an immunomodulator, an antioxidant and a drug metabolite. It is an enoate ester, a methyl ester and a dicarboxylic acid monoester. It derives from a fumaric acid.
Related reactions
8 records
Compound notes
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