HuagongsheHuagongshe Chemistry Print Report · For research reference only
Methylmalonic Acid
METHYLMALONIC ACID · 2-Methylmalonic acid · AI315327 · onic acid · NSC 25201 · AI3 15327 · AI3-15327 · Methylmalonic
Identifiers & Physical Properties
| CAS No. | 1215348-94-9 |
|---|---|
| Molecular formula | C4H6O4 |
| Average molar mass | 118.09 g/mol |
| Monoisotopic mass | 118.02660867 g/mol |
| SMILES | CC(C(=O)O)C(=O)O |
| InChIKey | ZIYVHBGGAOATLY-UHFFFAOYSA-N |
| PubChem CID | 487 |
| ChEMBL | CHEMBL1232416 |
| ChEBI | CHEBI:30860 |
| EC No. | 208-219-5 |
| DTXSID | DTXSID00199549 |
Chemical & Physical Properties
| XLogP | 0.1 |
|---|---|
| Topological polar surface area | 74.6 |
| Hydrogen bond donors | 2 |
| Hydrogen bond acceptors | 4 |
| Rotatable bonds | 2 |
| Heavy atoms | 8 |
| Formal charge | 0 |
| Complexity | 103 |
| Solubility | 679000679.0 mg/mLDMSO (Slightly), Methanol (Slightly)soluble |
| Melting point | 135135 °C128-130 °C (lit.) |
| Physical Description | Solid |
| Dissociation Constants | 3.12 (at 20 °C) |
| Boiling point | 272.71°C (rough estimate) |
| Density | 1.45 |
| Refractive index | 1.4304 (estimate) |
| Flash point | 2℃ |
| Storage conditions | Sealed in dry,Room Temperature |
| Physical state | Crystalline Powder |
| pKa (acidity coefficient) | 3.07, 5.76(at 25℃) |
| Color | White |
| Specific gravity | 1.455 |
| pH | 3.23(1 mM solution)2.6(10 mM solution)2.05(100 mM solution) |
| BRN | 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 | 516-05-2(CAS DataBase Reference) |
| EWG's Food Scores | 1 |
| FDA UNII | 8LL8S712J7 |
| NIST Chemistry Reference | Methylmalonic acid(516-05-2) |
| UNSPSC Code | 41116107 |
| NACRES | NA.24 |
| GHS pictogram | GHS07 |
| Signal word | Warning |
| GHS hazard statements | H315-H319-H335 |
| GHS precautionary statements | P302+P352-P305+P351+P338 |
| Target organs | Respiratory system |
| Hazard symbols | Xi,Xn,F |
| Risk statements (R) | 36/37/38-36-20/21/22-11 |
| Safety statements (S) | 26-36/37-16 |
| UN transport number | UN 1648 3 / PGII |
| Water hazard class (WGK) | 3 |
| RTECS number | OO1400000 |
| Customs code | 29171900 |
| Storage class | 11 - Combustible Solids |
| Hazard class | Eye Irrit. 2Skin Irrit. 2STOT SE 3 |
Safety & Regulations
| GHS classification | This chemical does not meet GHS hazard criteria for 5.4% (3 of 56) of reports.WarningH315 (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 exposureRespiratory 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 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%) |
| 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. |
| Carcinogen Classification | No indication of carcinogenicity to humans (not listed by IARC). |
| Water hazard class (WGK) | 3 |
| RTECS number | OO1400000 |
| UN transport number | UN 1648 3 / PGII |
| Customs code | 29171900 |
| Risk statements (R) | 36/37/38-36-20/21/22-11 |
| Signal word | Warning |
| GHS pictogram | GHS07 |
| Hazard symbols | Xi,Xn,F |
| Safety statements (S) | 26-36/37-16 |
| Storage class | 11 - Combustible Solids |
| Target organs | Respiratory system |
| GHS hazard statements | H315-H319-H335 |
| Hazard class | Eye Irrit. 2Skin Irrit. 2STOT SE 3 |
| GHS precautionary statements | P302+P352-P305+P351+P338 |
Applications & Uses
Uses
Methylmalonic 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).
Uses
2-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 Description
Methylmalonic 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.