Basic information
- Standard SMILES
CC(C(=O)O)C(=O)O- InChIKey
ZIYVHBGGAOATLY-UHFFFAOYSA-N- Molecular formula
- C4H6O4
- Average molar mass
- 118.09 g/mol
- Monoisotopic mass
- 118.02660867
Names & identifiers
- Preferred name
- Methylmalonic Acid
- IUPAC
- 2-methylpropanedioic acid
- English name
- 2-Methylpropanedioic acid
- Molecular formula
- C4H6O4
- Molecular weight
- 118.09
Names & synonyms
Show more names
Database identifiers
- CAS
1215348-94-9、516-05-2- PubChem CID
- 487
- DTXSID
DTXSID00199549- ChEMBL
CHEMBL1232416- ChEBI
CHEBI:30860- UNII
- 8LL8S712J7
- EC Number
- 208-219-5、693-939-6
- Nikkaji
- J6.302I
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
- 8
- Formal charge
- 0
- Complexity
- 103
Experimental & physicochemical properties
Solubility
679000
679.0 mg/mL
Melting Point
135
135 °C
Physicochemical properties
- Melting point
- 128 · 128-130 °C (lit.)
- Boiling point
- 272.71 °C · 272.71°C (rough estimate)
- Density
- 1.45 · 1.45
- refractive index
- 1.4304 · 1.4304 (estimate)
- Flash point
- 2 ℃ · 2℃
- storage temp.
- Sealed in dry,Room Temperature
- solubility
- DMSO (Slightly), Methanol (Slightly)
- form
- Crystalline Powder
- pka
- 3.07 · 3.07, 5.76(at 25℃)
- color
- White
- Specific Gravity
- 1.455 · 1.455
- PH
- 3.23 · 3.23(1 mM solution);2.6(10 mM solution);2.05(100 mM solution)
- Water Solubility
- soluble
- BRN
- 1756084 · 1756084
- InChI
- 1S/C4H6O4/c1-2(3(5)6)4(7)8/h2H,1H3,(H,5,6)(H,7,8)
- InChIKey
- ZIYVHBGGAOATLY-UHFFFAOYSA-N
- SMILES
- CC(C(O)=O)C(O)=O
- CAS DataBase Reference
- 516 · 516-05-2(CAS DataBase Reference)
- EWG's Food Scores
- 1 · 1
- FDA UNII
- 8 LL8S712J7 · 8LL8S712J7
- NIST Chemistry Reference
- Methylmalonic acid(516-05-2)
- UNSPSC Code
- 41116107 · 41116107
- NACRES
- 24 · NA.24
- Symbol(GHS)
- 7 · GHS07
- Signal word
- Warning
- Hazard statements
- 315 · H315-H319-H335
- Precautionary statements
- 302 · P302+P352-P305+P351+P338
- target organs
- Respiratory system
- Hazard Codes
- Xi,Xn,F
- Risk Statements
- 36 · 36/37/38-36-20/21/22-11
- Safety Statements
- 26 · 26-36/37-16
- RIDADR
- 1648 · UN 1648 3 / PGII
- WGK Germany
- 3 · 3
- RTECS
- 1400000 · OO1400000
- HS Code
- 29171900 · 29171900
- Storage Class
- 11 · 11 - Combustible Solids
- Hazard Classifications
- 2 Skin · Eye Irrit. 2Skin Irrit. 2STOT SE 3
Safety & regulation
GHS classification
GHS Classification
This chemical does not meet GHS hazard criteria for 5.4% (3 of 56) of reports.
Warning
H315 (94.6%): Causes skin irritation [Warning Skin corrosion/irritation];H319 (94.6%): Causes serious eye irritation [Warning Serious eye damage/eye irritation];H335 (92.9%): May cause respiratory irritation [Warning Specific target organ toxicity, single exposure; Respiratory tract 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 56 reports by companies from 6 notifications to the ECHA C&L Inventory. Each notification may be associated with multiple companies.;Reported as not meeting GHS hazard criteria per 3 of 56 reports by companies.;There are 5 notifications provided by 53 of 56 reports by companies with hazard statement code(s).;Information may vary between notifications depending on impurities, additives, and other factors. The percentage value in parenthesis indicates the notified classification ratio from companies that provide hazard codes. Only hazard codes with percentage values above 10% are shown. For more detailed information, please visit ECHA C&L website.
Hazard information
Hazard Classes and Categories
Skin Irrit. 2 (94.6%);Eye Irrit. 2 (94.6%);STOT SE 3 (92.9%)
Skin Irrit. 2 (100%);Eye Irrit. 2 (100%);STOT SE 3 (100%)
Toxicology
Health Effects
Chronically high levels of methylmalonic acid are associated with at least 5 inborn errors of metabolism including: Malonyl CoA decarboxylase deficiency, Malonic Aciduria, Methylmalonate Semialdehyde Dehydrogenase Deficiency, Methylmalonic Aciduria and Methylmalonic Aciduria Due to Cobalamin-Related Disorders.
Toxicity Summary
Methylmalonic acid is a vital intermediate in the metabolism of fat and protein. Abnormalities in methylmalonic acid metabolism lead to methylmalonic aciduria. This metabolic disease is attributed to a block in the enzymatic conversion of methylmalonyl CoA to succinyl CoA. Accumulation of Methylmalonic acid in the body has been shown to be toxic.
Safety data
- wgk
- 3
- rtecs
- OO1400000
- ridadr
- UN 1648 3 / PGII
- hs_code
- 29171900
- risk_code
- 36/37/38-36-20/21/22-11
- Signal word
- Warning
- Symbol(GHS)
- GHS07
- hazard_code
- Xi,Xn,F
- safety_code
- 26-36/37-16
- Storage Class
- 11 - Combustible Solids
- target organs
- Respiratory system
- Hazard statements
- H315-H319-H335
- Hazard Classifications
- Eye Irrit. 2Skin Irrit. 2STOT SE 3
- Precautionary statements
- P302+P352-P305+P351+P338
Chemistry & industry
Pharmacology
Metabolite Pathways
2-Methyl-3-Hydroxybutryl CoA Dehydrogenase Deficiency;3-Hydroxy-3-Methylglutaryl-CoA Lyase Deficiency;3-hydroxyisobutyric acid dehydrogenase deficiency;3-hydroxyisobutyric aciduria;3-Methylcrotonyl Coa Carboxylase Deficiency Type I;3-Methylglutaconic Aciduria Type I;3-Methylglutaconic Aciduria Type III;3-Methylglutaconic Aciduria Type IV;Beta-Ketothiolase Deficiency;Isobutyryl-coa dehydrogenase deficiency;Total 22 pathways, visit the HMDB page for details
Uses & manufacturing
Applications
UsesMethylmalonic acid can be used as a substrate in:Esterification reactions by various catalysts.Synthesis of pyrimidinium betaines with formamidine.Synthesis of malonic acid half thioester (MAHT).
Uses2-Methylpropanedioic acid binds with coenzyme A to form methylmalonyl-CoA, also a metabolic intermediate transformed to succinic acid (SA) by a vitamin B12-dependent catalytic step, and is broadly used as a clinical biomarker of functional vitamin B12 status.
General DescriptionMethylmalonic acid is an indicator of vitamin B12 deficiency and methylmalonic acidemia. This Certified Spiking Solution is suitable for use in preparation of calibrators or controls in clinical and diagnostic testing using GC/MS or LC/MS.
Upstream & downstream products
Upstream raw materials
Downstream products
Suppliers50 total
Additional notes
DefinitionChEBI: Methylmalonic acid is a dicarboxylic acid that is malonic acid in which one of the methylene hydrogens is substituted by a methyl group. It has a role as a human metabolite. It is functionally related to a malonic acid. It is a conjugate acid of a methylmalonate(1-).
Related reactions
Linked notes
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