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M54058

Sigma-Aldrich

Methylmalonic acid

99%

Synonym(s):

2-Methylpropanedioic acid

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About This Item

Linear Formula:
CH3CH(CO2H)2
CAS Number:
516-05-2
Molecular Weight:
118.09
Beilstein:
1756084
EC Number:
208-219-5
MDL number:
MFCD00002656
UNSPSC Code:
12352100
PubChem Substance ID:
24896996
NACRES:
NA.22

Assay

99%

mp

128-130 °C (lit.)

SMILES string

CC(C(O)=O)C(O)=O

InChI

1S/C4H6O4/c1-2(3(5)6)4(7)8/h2H,1H3,(H,5,6)(H,7,8)

InChI key

ZIYVHBGGAOATLY-UHFFFAOYSA-N

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Application

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).

Pictograms

Exclamation mark
GHS07

Signal Word

Warning

Hazard Statements

H315,H319,H335

Hazard Classifications

Eye Irrit. 2 - Skin Irrit. 2 - STOT SE 3

Target Organs

Respiratory system

Storage Class Code

11 - Combustible Solids

WGK

WGK 3

Flash Point(F)

Not applicable

Flash Point(C)

Not applicable

Personal Protective Equipment

dust mask type N95 (US), Eyeshields, Gloves

Certificates of Analysis (COA)

Search for Certificates of Analysis (COA) by entering the products Lot/Batch Number. Lot and Batch Numbers can be found on a product’s label following the words ‘Lot’ or ‘Batch’.

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L S Kornerup et al.
Clinical nutrition (Edinburgh, Scotland), 38(2), 906-911 (2018-03-07)
Bariatric surgery increases the risk of micronutrient deficiencies, including vitamin B12 (B12) deficiency. We analysed early changes in biomarkers of B12 status following bariatric surgery. We prospectively included adult patients (n = 27) referred for either Roux-en-Y Gastric Bypass (RYGB) (n = 19) or
Georg Staubli et al.
Pediatric emergency care, 32(12), 827-829 (2015-11-17)
The efficiency of nitrous oxide in an equimolar mixture with oxygen or in concentrations up to 70% is approved for short painful procedures. Evaluation of the vitamin B12 levels in anesthetic staff applying nitrous oxide showed reduced vitamin B12 plasma
A Stable anionic N-heterocyclic carbene and its zwitterionic complexes.
Cesar V, et al.
Journal of the American Chemical Society, 130(34), 11286-11287 (2008)
Novel Bronsted acidic ionic liquid as efficient and reusable catalyst system for esterification.
Gui J, et al.
Catalysis Communications, 5(9), 473-477 (2004)
Wendy Schijns et al.
The American journal of clinical nutrition, 108(1), 6-12 (2018-06-23)
After Roux-en-Y gastric bypass (RYGB), patients often develop a vitamin B-12 deficiency. Our objective was to investigate whether oral supplementation increases and normalizes low vitamin B-12 concentrations (vitamin B-12 > 200 pmol/L) in RYGB patients as compared to intramuscular injections. A randomized
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