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 8297
insulin secretion 8 Target ID: GO:0030073 Sources: https://www.ncbi.nlm.nih.gov/pubmed/10075107	Activator 1430
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 69 Sources: https://www.ncbi.nlm.nih.gov/pubmed/22364569	Diagnostic	Preclinical	Unknown Approved Use Unknown
Type 2 diabetes mellitus 259 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
Isolation of high-malate-producing sake yeasts from low-maltose-assimilating mutants.	2001	16233123
Synergistic insulinotropic effects of succinic acid dimethyl ester and exendin-4 in anaesthetized rats.	2001 Sep	11494054
Differences between mouse and rat pancreatic islets: succinate responsiveness, malic enzyme, and anaplerosis.	2002 Aug	12110535
Resistance of succinic acid dimethyl ester insulinotropic action to exendin (9-39) amide.	2002 Jan	11832995
(E)-2-(2-adamantylidene)-3-(1-ferrocenylethylidene)succinic anhydride.	2003 Feb	12574642
Synthesis and characterization of poly(butylene succinate-co-butylene malate): a new biodegradable copolyester bearing hydroxyl pendant groups.	2003 Mar-Apr	12625743
Similar effects of succinic acid dimethyl ester and glucose on islet calcium oscillations and insulin release.	2004 Mar 1	15104252
Degradation of malathion, in aqueous extracts of asparagus (Asparagus officinalis).	2004 Sep 22	15366843
The role of an astrocytic NADPH oxidase in the neurotoxicity of amyloid beta peptides.	2005 Dec 29	16321801
Bench-to-bedside review: potential strategies to protect or reverse mitochondrial dysfunction in sepsis-induced organ failure.	2006	16953900
Synthesis of 1,4-diphenylbutadiene derivatives: novel inducer of tissue-type plasminogen activator (t-PA) in cultured bovine endothelial cells.	2006 Dec	17139104
Process model and economic analysis of itaconic acid production from dimethyl succinate and formaldehyde.	2006 Jan	16171691
A Kir6.2 mutation causing neonatal diabetes impairs electrical activity and insulin secretion from INS-1 beta-cells.	2006 Nov	17065345
Methyl succinate antagonises biguanide-induced AMPK-activation and death of pancreatic beta-cells through restoration of mitochondrial electron transfer.	2007 Apr	17339833
Ca2+, NAD(P)H and membrane potential changes in pancreatic beta-cells by methyl succinate: comparison with glucose.	2007 Apr 1	17181533
Hypoxia stabilizes type 2 deiodinase activity in rat astrocytes.	2007 Oct	17615150
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 Aug 8	18544527
Mechanisms underlying the loss of mitochondrial membrane potential in glutamate excitotoxicity.	2008 Jul-Aug	18471431
Impaired anaplerosis and insulin secretion in insulinoma cells caused by small interfering RNA-mediated suppression of pyruvate carboxylase.	2008 Oct 17	18697738
Influence of Honey on the Suppression of Human Low Density Lipoprotein (LDL) Peroxidation (In vitro).	2009 Mar	18955249
PINK1-associated Parkinson's disease is caused by neuronal vulnerability to calcium-induced cell death.	2009 Mar 13	19285945
Solvation of dimethyl succinate in a sodium hydroxide aqueous solution. A computational study.	2009 May 7	19402729
Complete genome sequence of Gordonia bronchialis type strain (3410).	2010 Jan 28	21304674
Mechanism of neurodegeneration of neurons with mitochondrial DNA mutations.	2010 Mar	20157008
Glucose sensing in the pancreatic beta cell: a computational systems analysis.	2010 May 24	20497556
Chemical synthesis of fully biomass-based poly(butylene succinate) from inedible-biomass-based furfural and evaluation of its biomass carbon ratio.	2010 Oct 11	20815381

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 `Fri Dec 15 17:22:51 GMT 2023` Edited by `admin` on `Fri Dec 15 17:22:51 GMT 2023`
Record UNII	914I2127JR
Record Status	`Validated (UNII)`
Record Version

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Name

Type

Language

DIMETHYL SUCCINATE

Official 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

DIMETHYL SUCCINATE [INCI]

Common Name

English

SUCCINIC ACID DIMETHYL ESTER

Systematic 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

Created by admin on Fri Dec 15 17:22:51 GMT 2023 , Edited by admin on Fri Dec 15 17:22:51 GMT 2023

Food Contact Sustance Notif, (FCN No.)

FCN NO. 670

Created by admin on Fri Dec 15 17:22:51 GMT 2023 , Edited by admin on Fri Dec 15 17:22:51 GMT 2023

Food Contact Sustance Notif, (FCN No.)

FCN NO. 691

Created by admin on Fri Dec 15 17:22:51 GMT 2023 , Edited by admin on Fri Dec 15 17:22:51 GMT 2023

JECFA EVALUATION

DIMETHYL SUCCINATE

Created by admin on Fri Dec 15 17:22:51 GMT 2023 , Edited by admin on Fri Dec 15 17:22:51 GMT 2023

CFR

21 CFR 172.515

Created by admin on Fri Dec 15 17:22:51 GMT 2023 , Edited by admin on Fri Dec 15 17:22:51 GMT 2023

Code System Code Type Description

HSDB

5370

Created by admin on Fri Dec 15 17:22:51 GMT 2023 , Edited by admin on Fri Dec 15 17:22:51 GMT 2023

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DAILYMED

914I2127JR

Created by admin on Fri Dec 15 17:22:51 GMT 2023 , Edited by admin on Fri Dec 15 17:22:51 GMT 2023

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FDA UNII

914I2127JR

Created by admin on Fri Dec 15 17:22:51 GMT 2023 , Edited by admin on Fri Dec 15 17:22:51 GMT 2023

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NSC

52209

Created by admin on Fri Dec 15 17:22:51 GMT 2023 , Edited by admin on Fri Dec 15 17:22:51 GMT 2023

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EPA CompTox

DTXSID5025152

Created by admin on Fri Dec 15 17:22:51 GMT 2023 , Edited by admin on Fri Dec 15 17:22:51 GMT 2023

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MESH

C056451

Created by admin on Fri Dec 15 17:22:51 GMT 2023 , Edited by admin on Fri Dec 15 17:22:51 GMT 2023

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EVMPD

SUB69286

Created by admin on Fri Dec 15 17:22:51 GMT 2023 , Edited by admin on Fri Dec 15 17:22:51 GMT 2023

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JECFA MONOGRAPH

1114

Created by admin on Fri Dec 15 17:22:51 GMT 2023 , Edited by admin on Fri Dec 15 17:22:51 GMT 2023

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ECHA (EC/EINECS)

203-419-9

Created by admin on Fri Dec 15 17:22:51 GMT 2023 , Edited by admin on Fri Dec 15 17:22:51 GMT 2023

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MERCK INDEX

m10269

Created by admin on Fri Dec 15 17:22:51 GMT 2023 , Edited by admin on Fri Dec 15 17:22:51 GMT 2023

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Merck Index

CAS

106-65-0

Created by admin on Fri Dec 15 17:22:51 GMT 2023 , Edited by admin on Fri Dec 15 17:22:51 GMT 2023

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SMS_ID

100000135052

Created by admin on Fri Dec 15 17:22:52 GMT 2023 , Edited by admin on Fri Dec 15 17:22:52 GMT 2023

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RXCUI

2393581

Created by admin on Fri Dec 15 17:22:51 GMT 2023 , Edited by admin on Fri Dec 15 17:22:51 GMT 2023

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PUBCHEM

7820

Created by admin on Fri Dec 15 17:22:51 GMT 2023 , Edited by admin on Fri Dec 15 17:22:51 GMT 2023

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Details

SMILES

InChI

Approval Year

Targets

Conditions

Approved Use

Approved Use

Approved Use

PubMed

Patents

Sample Use Guides