96503-56-9

Basic information

• Product Name: (2E)-
• Synonyms: FuMaric Acid-1,4-13C2;2,3-D2, 98%);FUMARIC ACID (1-13C, 99%;L-THREONINE (4-13C, 97%;DL-Phenylalanine(1,2-13C2,99%;DL-Phenylalanine(2-13C,99%;DL-Tyrosine(1,2-13C2,99%;Ring-3,5-D2,98%)
• CAS NO: 96503-56-9
• Molecular Formula: C₄H₄O₄
• Molecular Weight: 144.12532
• Product Categories: Aliphatics;Isotope Labelled Compounds
• Mol File: 96503-56-9.mol

Chemical Properties

• Melting Point: 298-300 (subl)(lit.)
• Flash Point: 230 °C
• Appearance: /
• CAS DataBase Reference: (2E)-(CAS DataBase Reference)
• NIST Chemistry Reference: (2E)-(96503-56-9)
• EPA Substance Registry System: (2E)-(96503-56-9)

Safety Data

• Hazard Codes: Xi
• Statements: 36
• Safety Statements: 26
• Hazardous Substances Data: 96503-56-9(Hazardous Substances Data)

Usage

Uses

Used in Plant Respiration:
(2E)-Fumaric acid-1,4-13C2 is used as a vital component in the respiration process of plants, contributing to their overall growth and development. Its presence in many plants highlights its importance in the natural ecosystem.
Used as an Antioxidant:
(2E)-Fumaric acid-1,4-13C2 is utilized as an antioxidant, which helps in protecting cells from damage caused by reactive oxygen species. Its antioxidant properties make it a valuable compound in various applications, including food preservation, cosmetics, and pharmaceuticals, where it can prevent oxidation and extend shelf life.
Used in Research and Analysis:
The stable isotope labeling of (2E)-Fumaric acid-1,4-13C2 with 13C2 makes it an ideal compound for use in research and analytical applications. It can be employed as a tracer to study metabolic pathways, enzymatic reactions, and other biochemical processes, providing valuable insights into the underlying mechanisms.
Used in Pharmaceutical Industry:
(2E)-Fumaric acid-1,4-13C2 can be used in the pharmaceutical industry for the development of drugs targeting specific metabolic pathways. Its unique configuration and stable isotope labeling make it a promising candidate for drug discovery and design.
Used in Food Industry:
In the food industry, (2E)-Fumaric acid-1,4-13C2 can be used as a natural preservative and antioxidant, helping to maintain the quality and freshness of food products. Its ability to prevent oxidation can extend the shelf life of various food items, ensuring their safety and nutritional value.
Used in Cosmetics Industry:
(2E)-Fumaric acid-1,4-13C2 can be incorporated into cosmetics products for its antioxidant properties. It can help protect the skin from oxidative stress and environmental damage, promoting healthier and more youthful-looking skin.

Upstream product

• 100858-50-2 <1,4-13C2>maleic acid 
• 25909-68-6 [¹³C]-potassium cyanide 
• 107-06-2 1,2-dichloro-ethane 

Relevant articles and documents

Mechanistic and stereochemical investigation of fatty acid and polyketide biosynthesis using chiral malonates

Chiral malonates, (R)-[1-13C;2-2H]malonate and (S)-[1-13C;2-2H]malonate, were synthesised and characterised as malonyl-CoA derivatives with yeast fatty acid synthase using mass spectrometric analysis of the palmitic acid produced. The chiral malonates were used to investigate the steric course of fatty acid synthase from rat liver and the fatty acid synthase and 6-methylsalicylic acid synthase from Penicillium patulum. Malonic acid, activated in the form malonyl-CoA, is a key building block for the biosynthesis of many naturally occurring compounds including fatty acids, flavanones and polyketides. The methylene carbon atom of the malonyl-CoA, with its two hydrogen atoms, is of particular interest since it is at this position that many of the crucial mechanistic events occur during the assembly of these compounds. Detailed stereochemical information about the fate of the hydrogen atoms at this position during the incorporation of malonyl-CoA into these natural products is thus an essential requirement for the understanding of the mechanism and steric course of the enzymic steps involved. This problem was originally addressed by elegant studies in which the tritiated enantiomers of malonyl-CoA were synthesised and used to elucidate the mechanism of yeast fatty acid synthase. Difficulties encountered in this work with the extreme lability of the methylene protons suggested that the use of malonyl-CoA derivatives had severe limitations. This prompted us to devise an alternative strategy based on the synthesis of the more stable chiral malonates although this approach, as will be clear, introduces cryptic stereochemistry which complicates the analytical methodology. This stems from the fact that malonic acid exhibits pro-pro-chiral stereochemistry, having the structure Ca2b2. Thus even if the malonic acid is made chiral, by labeling the paired constituents isotopically with 13C and 2H in the same molecule, the labeled groups will remain essentially indistinguishable to an enzyme. Therefore each chiral malonate will yield a unique pair of malonyl-CoA derivatives, even when activated enzymically. Once formed, each of the malonyl-CoA derivatives will be recognised as a pro-chiral molecule by an enzyme and the labeled substituents will be manipulated stereospecifically. Such aspects have been discussed thoughtfully elsewhere. This paper discusses the synthesis of (R)-[1-13C;2-2H]malonate and (S)-[1-13C;2-2H]malonate and their use to study the mechanism and stereochemistry of fatty acid synthases and the polyketide synthase 6-methylsalicylic acid synthase.

The Synthesis of Chiral Malonates and the Determination of their Chirality using Fatty Acid Synthase and Mass Spectrometry

The chiral malonates, (R)-malonate and (S)-malonate, have been synthesised and their absolute configuration confirmed using fatty acid synthase and a novel procedure on mass spectrometry.