DIMETHYL SUCCINATE

Details

Stereochemistry	ACHIRAL
Molecular Formula	C6H10O4
Molecular Weight	146.1412
Optical Activity	NONE
Defined Stereocenters	0 / 0
E/Z Centers	0
Charge	0

SHOW SMILES / InChI

Structure Search

SMILES

COC(=O)CCC(=O)OC

InChI

InChIKey=MUXOBHXGJLMRAB-UHFFFAOYSA-N

InChI=1S/C6H10O4/c1-9-5(7)3-4-6(8)10-2/h3-4H2,1-2H3

HIDE SMILES / InChI

Molecular Formula	C6H10O4
Molecular Weight	146.1412
Charge	0
Count

Stereochemistry	ACHIRAL
Additional Stereochemistry	No
Defined Stereocenters	0 / 0
E/Z Centers	0
Optical Activity	NONE

Description
Sources: https://www.ncbi.nlm.nih.gov/pubmed/22364569 | https://www.ncbi.nlm.nih.gov/pubmed/26683377 | https://www.ncbi.nlm.nih.gov/pubmed/10934297 | https://www.ncbi.nlm.nih.gov/pubmed/9178284 | Burdock, G. A. (1997) Encyclopedia of Food and Color Additives, v.1 page 878, retrieved from: https://books.google.ru/books?id=vxtxWneRBN4C

Dimethyl succinate is the inactive analog of dimethyl fumarate. Dimethyl succinate has a pleasant, ethereal, winey odor and a fruity, winey, and burning flavor. It is used in foods as a flavoring ingredient. Dimethyl succinate was found at increased concentrations in the culture medium of the lung cancer cell line A549 and in the urine of mice implanted with A549 cells. Dimethyl succinate could be used to prolong the insulinotropic action of GLP-1 in the treatment of type-2 diabetes and it may represent a novel therapeutic approach in endotoxemia and multiple-organ failure.

Approval Year

Targets

Primary Target	Pharmacology	Condition	Potency
glucose metabolic process 4 Target ID: GO:0006006 Sources: https://www.ncbi.nlm.nih.gov/pubmed/7944393	Inhibitor 8504
insulin secretion 8 Target ID: GO:0030073 Sources: https://www.ncbi.nlm.nih.gov/pubmed/10075107	Activator 1447
Nasal mucosal carboxylesterase (Rat) 1 Target ID: Nasal mucosal carboxylesterase (Rat) Sources: https://www.ncbi.nlm.nih.gov/pubmed/1673384	Substrate 661

Conditions

Condition	Modality	Highest Phase	Product
Lung cancer 70 Sources: https://www.ncbi.nlm.nih.gov/pubmed/22364569	Diagnostic	Preclinical	Unknown Approved Use Unknown
Type 2 diabetes mellitus 262 Sources: https://www.ncbi.nlm.nih.gov/pubmed/10934297 https://www.ncbi.nlm.nih.gov/pubmed/10983625 https://www.ncbi.nlm.nih.gov/pubmed/11494054	Primary	Preclinical	Unknown Approved Use Unknown
Endotoxemia 3 Sources: https://www.ncbi.nlm.nih.gov/pubmed/9178284	Preventing	Preclinical	Unknown Approved Use Unknown

PubMed

Title	Date	PubMed
Chemical synthesis of fully biomass-based poly(butylene succinate) from inedible-biomass-based furfural and evaluation of its biomass carbon ratio.	2010-10-11	20815381
Glucose sensing in the pancreatic beta cell: a computational systems analysis.	2010-05-24	20497556
Mechanism of neurodegeneration of neurons with mitochondrial DNA mutations.	2010-03	20157008
Complete genome sequence of Gordonia bronchialis type strain (3410).	2010-01-28	21304674
Solvation of dimethyl succinate in a sodium hydroxide aqueous solution. A computational study.	2009-05-07	19402729
PINK1-associated Parkinson's disease is caused by neuronal vulnerability to calcium-induced cell death.	2009-03-13	19285945
Influence of Honey on the Suppression of Human Low Density Lipoprotein (LDL) Peroxidation (In vitro).	2009-03	18955249
Impaired anaplerosis and insulin secretion in insulinoma cells caused by small interfering RNA-mediated suppression of pyruvate carboxylase.	2008-10-17	18697738
Metabolomic and mass isotopomer analysis of liver gluconeogenesis and citric acid cycle. I. Interrelation between gluconeogenesis and cataplerosis; formation of methoxamates from aminooxyacetate and ketoacids.	2008-08-08	18544527
Mechanisms underlying the loss of mitochondrial membrane potential in glutamate excitotoxicity.	2007-12-20	18471431
Hypoxia stabilizes type 2 deiodinase activity in rat astrocytes.	2007-10	17615150
Ca2+, NAD(P)H and membrane potential changes in pancreatic beta-cells by methyl succinate: comparison with glucose.	2007-04-01	17181533
Methyl succinate antagonises biguanide-induced AMPK-activation and death of pancreatic beta-cells through restoration of mitochondrial electron transfer.	2007-04	17339833
Synthesis of 1,4-diphenylbutadiene derivatives: novel inducer of tissue-type plasminogen activator (t-PA) in cultured bovine endothelial cells.	2006-12	17139104
A Kir6.2 mutation causing neonatal diabetes impairs electrical activity and insulin secretion from INS-1 beta-cells.	2006-11	17065345
Process model and economic analysis of itaconic acid production from dimethyl succinate and formaldehyde.	2006-01	16171691
Bench-to-bedside review: potential strategies to protect or reverse mitochondrial dysfunction in sepsis-induced organ failure.	2006	16953900
The role of an astrocytic NADPH oxidase in the neurotoxicity of amyloid beta peptides.	2005-12-29	16321801
Degradation of malathion, in aqueous extracts of asparagus (Asparagus officinalis).	2004-09-22	15366843
Similar effects of succinic acid dimethyl ester and glucose on islet calcium oscillations and insulin release.	2004-03-01	15104252
Synthesis and characterization of poly(butylene succinate-co-butylene malate): a new biodegradable copolyester bearing hydroxyl pendant groups.	2003-03-11	12625743
(E)-2-(2-adamantylidene)-3-(1-ferrocenylethylidene)succinic anhydride.	2003-02	12574642
Differences between mouse and rat pancreatic islets: succinate responsiveness, malic enzyme, and anaplerosis.	2002-08	12110535
Resistance of succinic acid dimethyl ester insulinotropic action to exendin (9-39) amide.	2002-01	11832995
Synergistic insulinotropic effects of succinic acid dimethyl ester and exendin-4 in anaesthetized rats.	2001-09	11494054
Isolation of high-malate-producing sake yeasts from low-maltose-assimilating mutants.	2001	16233123

Patents

Sample Use Guides

In Vivo Use Guide

Rat: 5.0 uM/g body weight

Route of Administration: Intraperitoneal

In Vitro Use Guide

alpha- and beta-D-glucose pentaacetate (1.7 mM each) augmented, to almost the same extent, insulin release caused by succinic acid dimethyl ester (10.0 mM) in rat pancreatic islets. The release of insulin provoked by succinic acid dimethyl ester was inhibited, however, by alpha-D-galactose pentaacetate, whilst being unaffected by beta-D-galactose pentaacetate (each also 1.7 mM).

Substance Class	Chemical Created by `admin` on `Mon Mar 31 18:45:27 GMT 2025` Edited by `admin` on `Mon Mar 31 18:45:27 GMT 2025`
Record UNII	914I2127JR
Record Status	`Validated (UNII)`
Record Version

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Name

Type

Language

DIMETHYL SUCCINATE

Official Name

English

SUCCINIC ACID DIMETHYL ESTER

Preferred Name

English

DIMETHYL BUTANEDIOATE

Systematic Name

English

BUTANEDIOIC ACID, DIMETHYL ESTER

Common Name

English

SUCCINIC ACID, DIMETHYL ESTER

Common Name

English

DIMETHYL SUCCINATE [FHFI]

Common Name

English

BUTANEDIOIC ACID, 1,4-DIMETHYL ESTER

Common Name

English

FEMA NO. 2396

Code

English

SUCCINIC ACID DIMETHYL ESTER [MI]

Common Name

English

NSC-52209

Code

English

DIMETHYL SUCCINATE [FCC]

Common Name

English

DIMETHYL SUCCINATE [HSDB]

Common Name

English

Classification Tree Code System Code

Food Contact Sustance Notif, (FCN No.)

FCN NO. 625