Methylmalonic Acid

HCID 487CAS 1215348-94-9

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

Methylmalonic acid2-Methylmalonic acid516-05-22-Methylpropanedioic acidIsosuccinic acidmethylmalonatePropanedioic acid, methyl-1,1-Ethanedicarboxylic acidmethylpropanedioic acidMalonic acid, methyl-2-methyl-propanedioic acidCHEBI:30860
Show more names
AI315327onic acidNSC 25201AI3 15327AI3-15327Methylmalonicisosuccinicacid
DTXSID001995498LL8S712J7NSC-25201Acid, MethylmalonicRefChem:818643DTXCID10122040208-219-5MFCD00002656

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

Experimental & physicochemical properties

Solubility · 2 items

679000

679.0 mg/mL

Melting Point · 2 items

135

135 °C

Physical DescriptionSolid
Dissociation Constants3.12 (at 20 °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

Safety & regulation

GHS classification

GHS Classification · 6 items

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 · 2 items

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 · 1 item

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 · 1 item

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 ClassificationNo indication of carcinogenicity to humans (not listed by IARC).

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

Chemistry & industry

Pharmacology

Tissue LocationsKidney;Liver;Placenta
Cellular LocationsCytoplasm
Metabolite Pathways · 1 item

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

UsesThis is an endogenously produced metabolite found in the human body. It is used in metabolic reactions, catabolic reactions or waste generation.
Applications · 3 items

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.

Suppliers50 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]
上海策嵘生物科技有限公司[email protected]
广州隽沐生物科技股份有限公司020-36607679; 13502246435 · [email protected]
Dayang Chem (Hangzhou) Co.,Ltd.+86-0571-88938639 17705817739 · [email protected]
Additional notes · 1 item

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

26 records

Linked notes

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