Basic information
- Standard SMILES
C/C(=C\C(=O)O)C(=O)O- InChIKey
HNEGQIOMVPPMNR-NSCUHMNNSA-N- Molecular formula
- C5H6O4
- Average molar mass
- 130.1 g/mol
- Monoisotopic mass
- 130.02660867
Overview
Mesaconic acid is a dicarboxylic acid consisting of fumaric acid having a methyl substituent at the 2-position. It has a role as a plant metabolite and a human metabolite. It is a dicarboxylic fatty acid and a dicarboxylic acid. It is functionally related to a fumaric acid. It is a conjugate acid of a mesaconate(2-).
Names & identifiers
- Preferred name
- Mesaconic acid
- IUPAC
- (E)-2-methylbut-2-enedioic acid
- English name
- Mesaconic acid
- Molecular formula
- C5H6O4
- Molecular weight
- 130.1
Names & synonyms
mesaconic acid498-24-82-Methylfumaric acid2-Butenedioic acid, 2-methyl-, (2E)-Fumaric acid, methyl-(2E)-2-METHYLBUT-2-ENEDIOIC ACIDCitronic acid(E)-2-methylbut-2-enedioic acidtrans-2-Methyl-2-butenedioic acidtrans-1-Propene-1,2-dicarboxylic acidKyselina mesakonovaButenedioic acid, methyl-, (E)-
Show more names
Mesaconate2-methylfumarateMesaconicAcid>methyl-fumaricaciMESACONIC ACID 99%METHYLFUMARIC ACIDkyselinamesakonova
2-Butenedioic acid, 2-methyl-, (E)-Kyselina mesakonova [Czech](E)-Citraconic acid2-methyl-2E-butenedioic acidNSC 65438BRN 1722680(2E)-2-Methyl-2-butenedioic acidEINECS 207-859-2
Database identifiers
- CAS
498-23-7、498-24-8- PubChem CID
- 638129
- DTXSID
DTXSID10883407- ChEBI
CHEBI:16600- UNII
- 90UTM639KK
- EC Number
- 207-859-2
- Nikkaji
- J278.813F、J6.107G
Properties
Computed structural properties
- XLogP
- -0.1
- Topological polar surface area
- 74.6 Ų
- Hydrogen bond donors
- 2
- Hydrogen bond acceptors
- 4
- Rotatable bonds
- 2
- Heavy atoms
- 9
- Formal charge
- 0
- Complexity
- 168
Experimental & physicochemical properties
LipidsFatty Acyls [FA] -> Fatty Acids and Conjugates [FA01] -> Dicarboxylic acids [FA0117]
SpringerMaterials PropertiesCrystal structure
Solubility26.3 mg/mL at 18 °C
Melting Point200 - 202 °C
Physical DescriptionSolid
Physicochemical properties
- Melting point
- 200 · 200-202 °C(lit.)
- Boiling point
- 250 ° · bp 250° (decompn)
- Density
- 1.466 · 1.466
- refractive index
- 1.424 · 1.4240 (estimate)
- storage temp.
- 2 · 2-8°C
- solubility
- DMSO (Slightly), Methanol (Slightly)
- form
- Solid
- pka
- 3.09 · 3.09(at 25℃)
- color
- White to Off-White
- PH
- 3.23 · 3.23(1 mM solution);2.61(10 mM solution);2.06(100 mM solution)
- Water Solubility
- 26.3 g/L · 26.3g/L(18 ºC)
- Merck
- 5903 · 5903
- BRN
- 1722680 · 1722680
- InChI
- 1S/C5H6O4/c1-3(5(8)9)2-4(6)7/h2H,1H3,(H,6,7)(H,8,9)/b3-2+
- InChIKey
- HNEGQIOMVPPMNR-NSCUHMNNSA-N
- SMILES
- C\C(=C/C(O)=O)C(O)=O
- LogP
- 0.54 · 0.540 (est)
- CAS DataBase Reference
- 498 · 498-24-8(CAS DataBase Reference)
- EWG's Food Scores
- 1 · 1
- FDA UNII
- 90 UTM639KK · 90UTM639KK
- NIST Chemistry Reference
- 2 · 2-Butenedioic acid, 2-methyl-, (E)-(498-24-8)
- EPA Substance Registry System
- 2 · 2-Butenedioic acid, 2-methyl-, (2E)- (498-24-8)
- UNSPSC Code
- 12162002 · 12162002
- NACRES
- 23 · NA.23
- Symbol(GHS)
- 7 · GHS07
- Signal word
- Warning
- Hazard statements
- 335 · H335-H315-H319
- Precautionary statements
- 264 · P264-P280-P305+P351+P338-P337+P313P-P264-P280-P302+P352-P321-P332+P313-P362
- 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
- 3 · 3
- RTECS
- 5075000 · OX5075000
- TSCA
- TSCA listed
- Storage Class
- 11 · 11 - Combustible Solids
Safety & regulation
GHS classification
GHS Classification
Warning
H315 (100%): 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 39 reports by companies from 2 notifications to the ECHA C&L Inventory. Each notification may be associated with multiple companies.
Hazard information
Hazard Classes and CategoriesSkin Irrit. 2 (100%)
Safety data
- PPE
- dust mask type N95 (US), Eyeshields, Gloves
- wgk
- 3
- tsca
- TSCA listed
- rtecs
- OX5075000
- risk_code
- 36/37/38
- Signal word
- Warning
- Symbol(GHS)
- GHS07
- hazard_code
- Xi
- safety_code
- 26-36
- Storage Class
- 11 - Combustible Solids
- Hazard statements
- H335-H315-H319
- Precautionary statements
- P264-P280-P305+P351+P338-P337+P313P-P264-P280-P302+P352-P321-P332+P313-P362
Chemistry & industry
Pharmacology
Cellular LocationsExtracellular
Uses & manufacturing
General Manufacturing Information2-Butenedioic acid, 2-methyl-, (2E)-: ACTIVE
Applications
UsesMesaconic acid is used in electropolishing stainless steel and as a laminant for polyethylene.
UsesMesaconic Acid activates dopamine β-mono-oxygenase.
Upstream & downstream products
Upstream raw materials
Downstream products
Suppliers50 total
梯希爱(上海)化成工业发展有限公司021-67121386 · [email protected]
Hangzhou Collab Medicine Co.,Ltd.+86-15936229464 · [email protected]
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Hebei Chuanghai Biotechnology Co., Ltd+86-17732866630 · [email protected]
合肥曼奇诺生物医药技术有限公司19719236623 · [email protected]
广州佳途科技股份有限公司81960175 18933936954 · [email protected]
杭州品高化工有限公司0571-87658025 · [email protected]
上海毕得医药科技股份有限公司400-1647117 13681763483 · [email protected]
Dayang Chem (Hangzhou) Co.,Ltd.+86-0571-88938639 17705817739 · [email protected]
Syntechem Co.,Ltd[email protected]
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Nanjing jinheyou Trading Co., Ltd.15705188088 · [email protected]
BOC Sciences1-631-485-4226; 16314854226 · [email protected]
ChemeGen 中国18818260767 · [email protected]
ZHEJIANG JIUZHOU CHEM CO., LTD+86-0576225566889 +86-13454675544 · [email protected]；[email protected]；[email protected]
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Alfa Chemistry1-516-6625404 · [email protected]
上海陶术生物科技股份有限公司+1-781-999-5354; +1-00000000000 · [email protected]
九鼎化学（上海）科技有限公司4009209199 · [email protected]
Henan Alfa Chemical Co., Ltd+8618339805032 · [email protected]
HANGZHOU LEAP CHEM CO., LTD.+86-571-87711850 +86-15355479329 · [email protected]
艾吉析科技（上海）有限公司17721401538;17717235263 17721401538 · [email protected]
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成都标样生物科技有限公司028-81700200 13308200041 · [email protected]
山东西亚化学有限公司4009903999 13395398332 · [email protected]
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Shanghai Acmec Biochemical Technology Co., Ltd.+86-18621343501 · [email protected]
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杭州洁汉化工有限公司+86-571-86217390; +8618058761490 · [email protected]
江苏艾康生物医药研发有限公司025-58859352 19370895928 · [email protected]
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上海吉至生化科技有限公司021-4009004166/18616739031 18616739031 · [email protected]
北京沃凯生物科技有限公司010-62971590 18548936886 · [email protected]
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深圳利斯康医药科技有限公司+86-755-89396905 +86-15013857715 · [email protected]
Aladdin Scientific[email protected]
上海皓鸿生物医药科技有限公司400-8210725 4008210725 · [email protected]
河南奥创化工有限公司+86-0371-63689365 +8618638391208 · [email protected]
Additional notes
DefinitionChEBI: Mesaconic acid is a dicarboxylic acid consisting of fumaric acid having a methyl substituent at the 2-position. It has a role as a plant metabolite and a human metabolite. It is a dicarboxylic fatty acid and a dicarboxylic acid. It is functionally related to a fumaric acid. It is a conjugate acid of a mesaconate(2-).
Related reactions
3 records
Linked notes
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