Dimethyl glutaconate - ≥97%(GC) , CAS No.5164-76-1

CAS: 5164-76-1 Cat. No.: D170731 Molecular Weight: 158.15 Beilstein Registry Number: 1724170 EC Number: 684-568-0

GRADE & PURITY ≥97%(GC)

Synonyms

Q63399975 | Dimethyl glutaconate, >=97.0% (GC) | STL146644 | 1,5-DIMETHYL (2E)-PENT-2-ENEDIOATE | AKOS005720779 | Dimethyl (2E)-2-pentenedioate # | EN300-364795 | Glutaconic acid, dimethyl ester | (E)-dimethylpent-2-enedioate | dimethyl (2E)-pent-2-enedio

Storage

Room temperature

Shipped In

Normal

Overview

Dimethyl glutaconate, also known as dimethyl 2-pentenoate, is a diester. It reacts with salicaldehyde in the presence of piperidine to form a coumarin-fused electron deficient diene.
Dimethyl glutaconate may be used in the synthesis of: ? dimethyl 3-[(Z)-1-propenyl]glutarate ? phenanthridinone derivatives ? substituted benzenes

Specifications

Synonyms

Q63399975 | Dimethyl glutaconate, >=97.0% (GC) | STL146644 | 1, 5-DIMETHYL (2E)-PENT-2-ENEDIOATE | AKOS005720779 | Dimethyl (2E)-2-pentenedioate # | EN300-364795 | Glutaconic acid, dimethyl ester | (E)-dimethylpent-2-enedioate | dimethyl (2E)-pent-2-enedio

Specifications & Purity

≥97%(GC)

Storage

Room temperature

Shipped In

Normal

Purity

≥97%(GC)

Names and Identifiers

• Canonical Smiles: COC(=O)CC=CC(=O)OC
• IUPAC Name: dimethyl (E)-pent-2-enedioate
• InChIKey: SKCGFFOFYXLNCG-ONEGZZNKSA-N
• INCHI: 1S/C7H10O4/c1-10-6(8)4-3-5-7(9)11-2/h3-4H,5H2,1-2H3/b4-3+
• Isomeric SMILES: COC(=O)C/C=C/C(=O)OC
• WGK Germany: 3
• Molecular Weight: 158.15
• Beilstein: 1724170
• Reaxy-Rn: 1771713
• Reaxys-RN_link_address: https://www.reaxys.com/reaxys/secured/hopinto.do?context=S&query=IDE.XRN=1771713&ln=

Taxonomic Classification

Taxonomy Tree

• Kingdom Organic compounds
  • Superclass Lipids and lipid-like molecules
    • Class Fatty Acyls
      • Subclass Fatty acid esters

• Kingdom: Organic compounds
• Superclass: Lipids and lipid-like molecules
• Class: Fatty Acyls
• Subclass: Fatty acid esters
• Intermediate Tree Nodes: Not available
• Direct Parent: Fatty acid methyl esters
• Alternative Parents: Dicarboxylic acids and derivatives Methyl esters Enoate esters Organic oxides Hydrocarbon derivatives Carbonyl compounds
• Molecular Framework: Aliphatic acyclic compounds
• Substituents: Fatty acid methyl ester - Dicarboxylic acid or derivatives - Alpha,beta-unsaturated carboxylic ester - Enoate ester - Methyl ester - Carboxylic acid ester - Carboxylic acid derivative - Organic oxygen compound - Organic oxide - Hydrocarbon derivative - Organooxygen compound - Carbonyl group - Aliphatic acyclic compound
• Description: This compound belongs to the class of organic compounds known as fatty acid methyl esters. These are compounds containing a fatty acid that is esterified with a methyl group. They have the general structure RC(=O)OR', where R=fatty aliphatic tail or organyl group and R'=methyl group.
• External Descriptors: Not available

Data sources

1. Djoumbou Feunang Y, Eisner R, Knox C, Chepelev L, Hastings J, Owen G, Fahy E, Steinbeck C, Subramanian S, Bolton E, Greiner R, and Wishart DS. ClassyFire: Automated Chemical Classification With A Comprehensive, Computable Taxonomy. Journal of Cheminformatics, 2016, 8:61.

DOI: 10.1186/s13321-016-0174-y

Associated Targets(non-human)

Aspergillus niger (16508 Activities)

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Candida albicans (78123 Activities)

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Mucor mucedo (338 Activities)

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Mechanisms of Action

Chemical and Physical Properties

• Refractive Index: 1.452
• Flash Point(°F): >212 °F
• Flash Point(°C): >100 °C
• Molecular Weight: 158.150 g/mol
• XLogP3: 0.400
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 4
• Rotatable Bond Count: 5
• Exact Mass: 158.058 Da
• Monoisotopic Mass: 158.058 Da
• Topological Polar Surface Area: 52.600 Ų
• Heavy Atom Count: 11
• Formal Charge: 0
• Complexity: 171.000
• Isotope Atom Count: 0
• Defined Atom Stereocenter Count: 0
• Undefined Atom Stereocenter Count: 0
• Defined Bond Stereocenter Count: 1
• Undefined Bond Stereocenter Count: 0
• The total count of all stereochemical bonds: 1
• Covalently-Bonded Unit Count: 1

References

1. Xiao Tu, Jiaxin Hu, Jinghao Peng, Qihan Chen, Yangle Zhao, Zemao Gu.  (2025)  Discovery of thymoquinone analogues with high anthelmintic activity against monogenean infections in goldfish (Carassius auratus).  VETERINARY PARASITOLOGY,      [PMID:39837239] [10.1016/j.vetpar.2025.110401]