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S3674

Sigma-Aldrich

Succinic acid

greener alternative

BioXtra, BioRenewable, ≥99.0%

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Synonym(s):
Butanedioic acid
Linear Formula:
HOOCCH2CH2COOH
CAS Number:
110-15-6
Molecular Weight:
118.09
Beilstein:
1754069
EC Number:
203-740-4
MDL number:
MFCD00002789
PubChem Substance ID:
24899568
NACRES:
NA.25

Quality Level

200

product line

BioXtra

Assay

≥99.0%

greener alternative product characteristics

Use of Renewable Feedstocks
Learn more about the Principles of Green Chemistry.

impurities

≤0.01% Insoluble matter

ign. residue

≤0.02%

bp

235 °C (lit.)

mp

184-186 °C (lit.)

solubility

H2O: 0.5 M, clear, colorless

anion traces

chloride (Cl-): ≤0.001%
sulfate (SO42-): ≤0.003%

cation traces

Al: ≤0.0005%
Ca: ≤0.001%
Cu: ≤0.0005%
Fe: ≤0.0005%
K: ≤0.005%
Mg: ≤0.0005%
NH4+: ≤0.05%
Na: ≤0.005%
Pb: ≤0.001%
Zn: ≤0.0005%

greener alternative category

, Aligned

SMILES string

OC(=O)CCC(O)=O

InChI

1S/C4H6O4/c5-3(6)1-2-4(7)8/h1-2H2,(H,5,6)(H,7,8)

InChI key

KDYFGRWQOYBRFD-UHFFFAOYSA-N

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General description

We are committed to bringing you Greener Alternative Products, which adhere to one or more of The 12 Principles of Greener Chemistry. This product is biobased and thus aligns with "Use of Renewable Feedstocks". Click here for more information.

Application

Succinic acid has been used:
  • in succinate dehydrogenase mitochondrial assay.
  • as an internal standard in mass spectroscopy.
  • as succinate dehydrogenase substrate in oxygraph analysis to measure respiration rates.

Biochem/physiol Actions

Succinic acid is a byproduct of anaerobic fermentation in microbes. It is a dicarboxylic acid and an intermediate in Kreb′s cycle. Polymorphism in succinate dehydrogenase leads to succinate accumulation. High levels of succinate impairs 2-oxoglutarate epigenetic signalling. Succinate levels may modulate tumor progression. Succinate inhibits histone demethylation and may contribute to epigenetic changes. Succinate is crucial for interleukin-1 β (IL-1β) synthesis during inflammation and immune signalling.

Other Notes

Succinic Acid: A New Platform Chemical for Biobased Polymers from Renewable Resources

Pictograms

Corrosion
GHS05

Signal Word

Danger

Hazard Statements

H318

Precautionary Statements

P280 - P305 + P351 + P338

Hazard Classifications

Eye Dam. 1

Storage Class Code

11 - Combustible Solids

WGK

WGK 1

Flash Point(F)

Not applicable

Flash Point(C)

Not applicable

Personal Protective Equipment

dust mask type N95 (US), Eyeshields, Gloves

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Hyperactivation of oxidative mitochondrial metabolism in epithelial cancer cells in situ: visualizing the therapeutic effects of metformin in tumor tissue
Whitaker-Menezes D, et al.
Cell Cycle, 10(23), 4047-4064 (2011)
Screening For Isolation of Succinic Acid Producing Microbes
Hema N and Sreenath KP
Biosciences, Biotechnology Research Asia, 15(2), 327-333 (2018)
Succinate: a new epigenetic hacker
Yang M and Pollard PJ
Cancer Cell, 23(6), 709-711 (2013)
Cardiomyocyte differentiation: Experience and observations from 2 laboratories
Patten VA, et al.
SA heart journal, 14(2), 96-107 (2017)
Oncometabolites: Unconventional triggers of oncogenic signalling cascades
Sciacovelli M and Frezza C
Free Radical Biology & Medicine, 100(9), 175-181 (2016)
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