Methylmalonic acid

Structural formula
General
Surname	Methylmalonic acid
other names	Methylpropanedioic acid
Molecular formula	C 4 H 6 O 4
Brief description	pale beige, fine crystals
External identifiers / databases
CAS number 516-05-2 EC number 208-219-5 ECHA InfoCard 100.007.473 PubChem 487 ChemSpider 473 DrugBank DB04183 Wikidata Q239598
properties
Molar mass	118.09 g mol −1
Physical state	firmly
density	1.455 g cm −3 (20 ° C)
Melting point	128-130 ° C
pK s value	pK s 1 = 3.07 pK s 2 = 5.76
solubility	good in water
safety instructions
GHS labeling of hazardous substances Caution H and P phrases H: 315-319-335 P: 261-305 + 351 + 338
Toxicological data	100 mg kg −1 ( LD 50 ,  mouse ,  iv )
As far as possible and customary, SI units are used. Unless otherwise noted, the data given apply to standard conditions .

Methylmalonic acid (MMS) is a chemical compound from the group of dicarboxylic acids . It consists of the basic structure of malonic acid and also carries a methyl group . The salts of methylmalonic acid are called methylmalonates .

Presentation and extraction

Methymalonsäure can be prepared by the oxidation of 2-methyl propane-1,3-diol by means of potassium permanganate or nitric acid are obtained.

Importance in metabolism

One of the consequences of a vitamin B ₁₂ deficiency is an increase in methylmalonyl-CoA , which is metabolized to methylmalonic acid.

It has been shown that 90 to 98% of patients with a proven vitamin B ₁₂ deficiency also have an increased amount of MMS. In this respect, test procedures can be used to prove that the cause of an increased MMS value (as well as an increased homocysteine level ) is often a vitamin B ₁₂ deficiency.

Nevertheless, the examination of the MMS concentration is not sufficient to conclude a vitamin B ₁₂ deficiency. For example, about a quarter of people over the age of 70 have increased MMS levels in their bodies; 24 to 33% of these show no vitamin B ₁₂ deficiency.

The methylmalonic acid concentration in the blood is measured in practice using gas chromatographic mass spectrometry analysis.

Laboratory synthesis

Methylmalonic acid can be produced by malonic ester synthesis from diethyl malonate and bromomethane . The ester produced in the first stage is then saponified and the salt is converted to methylmalonic acid with a strong acid.

Individual evidence

1. ↑ ^{a b c d e} data sheet Methylmalonic acid from Sigma-Aldrich , accessed on October 22, 2016 ( PDF ).
2. ↑ Tanatar; Tschelebiev: in Chemical Reports 24 (1891) 271.
3. ↑ ^{a b} Dissociation Constants Of Organic Acids and Bases (600 compounds)
4. ↑ Data methylmalonic acid from Acros, accessed on 20 February 2010 .
5. ↑ Faworsdi: in Justus Liebigs Annalen der Chemie 354 (1907) 362.
6. ^ Pummerer et al .: in Chemischeberichte 75 (1942) 880.
7. ↑ dizziness-and-balance.com: B12 Deficiiency and Dizziness.
8. ↑ Sonia Isber: The role of poor nutritional status and hyperhomocysteinemia in complicated pregnancy in Syria. (PDF; 763 kB) Dissertation, Saarland University, 2006. urn : nbn: de: bsz: 291-scidok-10769