Succinic acid (səkˈsɪnᵻk) is a dicarboxylic acid with the chemical formula (CH2)2(CO2H)2. In living organisms, succinic acid takes the form of an anion, succinate, which has multiple biological roles as a metabolic intermediate being converted into fumarate by the enzyme succinate dehydrogenase in complex 2 of the electron transport chain which is involved in making ATP, and as a signaling molecule reflecting the cellular metabolic state. Succinate is generated in mitochondria via the tricarboxylic acid cycle (TCA). Succinate can exit the mitochondrial matrix and function in the cytoplasm as well as the extracellular space, changing gene expression patterns, modulating epigenetic landscape or demonstrating hormone-like signaling. As such, succinate links cellular metabolism, especially ATP formation, to the regulation of cellular function. Dysregulation of succinate synthesis, and therefore ATP synthesis, happens in some genetic mitochondrial diseases, such as Leigh syndrome, and Melas syndrome, and degradation can lead to pathological conditions, such as malignant transformation, inflammation and tissue injury. Succinic acid is marketed as food additive E363. The name derives from Latin succinum, meaning amber. Succinic acid is a white, odorless solid with a highly acidic taste. In an aqueous solution, succinic acid readily ionizes to form its conjugate base, succinate (ˈsʌksᵻneɪt). As a diprotic acid, succinic acid undergoes two successive deprotonation reactions: (CH2)2(CO2H)2 → (CH2)2(CO2H)(CO2)− + H+ (CH2)2(CO2H)(CO2)− → (CH2)2(CO2)22− + H+ The pKa of these processes are 4.3 and 5.6, respectively. Both anions are colorless and can be isolated as the salts, e.g., Na(CH2)2(CO2H)(CO2) and Na2(CH2)2(CO2)2. In living organisms, primarily succinate, not succinic acid, is found. As a radical group it is called a succinyl (ˈsʌksᵻnəl) group. Like most simple mono- and dicarboxylic acids, it is not harmful but can be an irritant to skin and eyes. Historically, succinic acid was obtained from amber by distillation and has thus been known as spirit of amber.

About this result
This page is automatically generated and may contain information that is not correct, complete, up-to-date, or relevant to your search query. The same applies to every other page on this website. Please make sure to verify the information with EPFL's official sources.
Ontological neighbourhood
Related courses (7)
ENV-202: Microbiology for engineers
"Microbiology for engineers" covers the main microbial processes that take place in the environment and in treatment systems. It presents elemental cycles that are catalyzed by microorganisms and that
CH-313: Chemical biology
Closely interfacing with bioengineering and medicine, this course provides foundational concepts in applying small-molecule chemical toolsets to probe the functions of living systems at the mechanisti
FIN-609: Asset Pricing (2011 - 2024)
This course provides an overview of the theory of asset pricing and portfolio choice theory following historical developments in the field and putting emphasis on theoretical models that help our unde
Show more
Related lectures (33)
Microbial Carbon Fixation
Explores microbial pathways for carbon fixation and the production of key metabolites.
Expected Utility and Risk-Aversion: Theoretical Foundations
Explores expected utility, risk-aversion, insurance premiums, and portfolio choice in asset pricing.
Photosynthesis: Anoxygenic Phototrophs and Carbon Fixation
Explores photosynthesis in anoxygenic phototrophs and the mechanisms of carbon fixation.
Show more
Related publications (115)

Influence of Amino Acid Substitutions in Capsid Proteins of Coxsackievirus B5 on Free Chlorine and Thermal Inactivation

Tamar Kohn, Aleksandar Antanasijevic, Kiruthika Kumar, Shotaro Torii

The sensitivity of enteroviruses to disinfectants varies among genetically similar variants and coincides with amino acid changes in capsid proteins, although the effect of individual substitutions remains unknown. Here, we employed reverse genetics to inv ...
2024

Metabolic dependencies of metastasis-initiating cells in female breast cancer

Albert Santamaria Martinez, Pierre Vincent Dessen, Angela Madurga Alonso, Candice Megan T Young, Laurent Nam Ky Beziaud

Understanding the mechanisms that enable cancer cells to metastasize is essential in preventing cancer progression. Here we examine the metabolic adaptations of metastasis-initiating cells (MICs) in female breast cancer and how those shape their metastatic ...
Berlin2023

Controlling the crystal structure of succinic acid via microfluidic spray-drying

Esther Amstad, Aysu Ceren Okur

Many properties of materials, including their dissolution kinetics, hardness, and optical appearance, depend on their structure. Unfortunately, it is often difficult to control the structure of low molecular weight organic compounds that have a high propen ...
ROYAL SOC CHEMISTRY2023
Show more
Related concepts (18)
Malic acid
Malic acid is an organic compound with the molecular formula . It is a dicarboxylic acid that is made by all living organisms, contributes to the sour taste of fruits, and is used as a food additive. Malic acid has two stereoisomeric forms (L- and D-enantiomers), though only the L-isomer exists naturally. The salts and esters of malic acid are known as malates. The malate anion is an intermediate in the citric acid cycle. The word 'malic' is derived from Latin 'mālum', meaning 'apple'.
Oxaloacetic acid
Oxaloacetic acid (also known as oxalacetic acid or OAA) is a crystalline organic compound with the chemical formula HO2CC(O)CH2CO2H. Oxaloacetic acid, in the form of its conjugate base oxaloacetate, is a metabolic intermediate in many processes that occur in animals. It takes part in gluconeogenesis, the urea cycle, the glyoxylate cycle, amino acid synthesis, fatty acid synthesis and the citric acid cycle. Oxaloacetic acid undergoes successive deprotonations to give the dianion: HO2CC(O)CH2CO2H −O2CC(O)CH2CO2H + H+, pKa = 2.
Dicarboxylic acid
In organic chemistry, a dicarboxylic acid is an organic compound containing two carboxyl groups (). The general molecular formula for dicarboxylic acids can be written as , where R can be aliphatic or aromatic. In general, dicarboxylic acids show similar chemical behavior and reactivity to monocarboxylic acids. Dicarboxylic acids are used in the preparation of copolymers such as polyamides and polyesters. The most widely used dicarboxylic acid in the industry is adipic acid, which is a precursor in the production of nylon.
Show more
Related MOOCs (1)
Water quality and the biogeochemical engine
Learn about how the quality of water is a direct result of complex bio-geo-chemical interactions, and about how to use these processes to mitigate water quality issues.

Graph Chatbot

Chat with Graph Search

Ask any question about EPFL courses, lectures, exercises, research, news, etc. or try the example questions below.

DISCLAIMER: The Graph Chatbot is not programmed to provide explicit or categorical answers to your questions. Rather, it transforms your questions into API requests that are distributed across the various IT services officially administered by EPFL. Its purpose is solely to collect and recommend relevant references to content that you can explore to help you answer your questions.