4093-49-6

Usage

Uses

Used in Chemical Synthesis:
FUMARALDEHYDE MONO(DIMETHYL ACETAL) is used as an intermediate in the synthesis of various organic compounds, including 4-Hydroxy Nonenal Mercapturic Acid (H296810), a mercapturic acid conjugate of 4-hydroxy nonenal (4-HNE). This synthesis is crucial for the clearance of 4-HNE from plasma via enterohepatic circulation, which is essential for maintaining cellular health and function.
Used in Membrane Technology:
FUMARALDEHYDE MONO(DIMETHYL ACETAL) is utilized in the development of crosslinked polyolefin separation membranes. These membranes are vital in various industrial processes, such as gas separation, water treatment, and chemical purification, due to their enhanced selectivity, permeability, and stability.

Synthesis Reference(s)

Tetrahedron Letters, 27, p. 4983, 1986 DOI: 10.1016/S0040-4039(00)85113-8

InChI:InChI=1/C6H10O3/c1-8-6(9-2)4-3-5-7/h3-6H,1-2H3/b4-3+

Upstream product

• 110-00-9 furan 
• 67-56-1 methanol 
• 6068-62-8 trans-butenedial bis-(dimethyl acetal) 
• 332-77-4 2,5-dihydro-2,5-dimethoxyfuran 

Downstream Products

• 14025-78-6 α-(4,4-Dimethoxy-butylryloxy)-α-phenylacetonitril 
• 19255-60-8 (E)-4,4-dimethoxy-but-2-enoic acid ethyl ester 
• 910662-15-6 (2E,8E,10E)-11-(3,5-dimethoxyphenyl)-1,1-dimethoxyundeca-2,8,10-trien-4-ol 
• 128860-92-4 tert-Butyl-[(R)-1-((E)-3,3-dimethoxy-propenyl)-hexyloxy]-diphenyl-silane 
• 128860-93-5 tert-Butyl-[(S)-1-((E)-3,3-dimethoxy-propenyl)-hexyloxy]-diphenyl-silane 
• 128860-98-0 Benzoic acid (2E,4Z,7Z)-(R)-11-methoxycarbonyl-1-pentyl-undeca-2,4,7-trienyl ester 
• 128860-99-1 Benzoic acid (2E,4E,7Z)-(S)-11-methoxycarbonyl-1-pentyl-undeca-2,4,7-trienyl ester 
• 1403749-15-4 (E)-methyl (4-oxo-1-phenylbut-2-en-1-yl) methyl carbonate 
• 1403749-17-6 (E)-ethyl (4-oxo-1-phenylbut-2-en-1-yl) carbonate 
• 1403749-44-9 (E)-methyl (4-oxo-1-(p-tolyl)but-2-en-1-yl) carbonate 
• 1403749-52-9 (E)-1-(3-methoxyphenyl)-4-oxobut-2-en-1-yl methyl carbonate 
• 1403749-53-0 (E)-1-(3,5-bis(trifluoromethyl)phenyl)-4-oxobut-2-en-1-yl methyl carbonate 
• 1403749-54-1 (E)-1-(4-fluorophenyl)-4-oxobut-2-en-1-yl methyl carbonate 

Relevant academic research and scientific papers

Total Synthesis of a Docosahexaenoic Acid Prostanoid Using an Intramolecular Organocatalytic Michael Reaction of a Formyl-Enal Derivative

The total synthesis of a docosahexaenoic-acid-derived prostaglandin, 4,11-diepi-4-F4t-neuroprostane, featuring a complex lateral chain was achieved for the first time. A novel prostaglandin cyclopentane skeleton obtained via an intramolecular highly selective organocatalytic Michael sequence of a formyl-enal derivative allowed the desired and exclusive thermodynamic trans configuration of the lipidic lateral chains.

BIPOLAR TRANS CAROTENOID SALTS AND USES THEREOF

PROBLEM TO BE SOLVED: To provide compounds useful in improving diffusivity of oxygen between red blood cells and body tissues in mammals including humans. SOLUTION: There is provided a compound which has a structure represented by YZ-TCRO-ZY and is not trans sodium crocetinate [where, Y is a cation; Z is a polar group which is associated with the cation; and TCRO is trans carotenoid skeleton], and preferably, Y is a monovalent metal ion selected from the group consisting of Na+, K+ and Li+, or is an organic cation selected from the group consisting of R4 N+ and R3S+ [R is H, or CnH2n+1(n is 1 to 10)]. SELECTED DRAWING: None COPYRIGHT: (C)2018,JPO&INPIT

Synthesis of a simplified triazole analogue of pateamine A

Pateamine A is a naturally occurring metabolite extracted from the marine sponge Mycale hentscheli. It exhibits potent cytotoxicity towards cancer cell lines and has been shown to target protein translation initiation via inhibition of the function of euk

BIPOLAR TRANS CAROTENOID SALTS AND THEIR USE

PROBLEM TO BE SOLVED: To provide trans carotenoid salt compounds useful for improving the diffusibility of oxygen between red blood cells and a body tissue in mammalian including human being, a method for producing them, a method for solubilizing them, and a method for using them. SOLUTION: There are provided compounds represented by the following formula, and are compounds not being trans sodium crocetinate: YZ-TCRO-ZY[Y denotes a cation; Z denotes a polar group coupled to the cation; TCRO denotes a trans carotenoid skeleton; preferably, as follows; Y denotes the monovalent metal ion of Na+,K+ or Li+ or R4 N+ or R3S+;R denotes H or CnH2n+1;n denotes the integer of 1 to 10;Z denotes a carboxyl group, a sulfuric acid group, a mono-phosphoric acid group, a di-phosphoric acid group, or a tri-phosphoric acid group; and TCRO denotes a group using isopronoid in which the single bond and double bond of straight chain carbon and carbon as exemplified by the following formula is repeated (X respectively independently denotes H, a straight chain/branched carbon chain substituted/non-substituted with 1 to 10C halogen or a halogen)]. SELECTED DRAWING: None COPYRIGHT: (C)2017,JPO&INPIT

Stereoselective synthesis of epoxyisoprostanes: an organocatalytic and "pot-economy" approach

An efficient and direct synthetic route to epoxyisoprostane EC methyl ester has been accomplished in 8 steps (10% overall yield) from readily available starting materials using a series of asymmetric organocatalytic reactions and one-pot operations.

Transition-metal-catalyzed synthesis of aspergillide B: An alkyne addition strategy

A catalytic enantioselective formal total synthesis of aspergillide B is reported. This linchpin synthesis was enabled by the development of new conditions for Zn-ProPhenol catalyzed asymmetric alkyne addition. This reaction was used in conjunction with ruthenium-catalyzed trans-hydrosilylation to affect the rapid construction of a late-stage synthetic intermediate of aspergillide B to complete a formal synthesis of aspergillide B in a highly efficient manner.

Development of Zn-prophenol-catalyzed asymmetric alkyne addition: Synthesis of chiral propargylic alcohols

The development of a general and practical zinc-catalyzed enantioselective alkyne addition methodology is reported. The commercially available ProPhenol ligand (1) has facilitated the addition of a wide range of zinc alkynylides to aryl, aliphatic, and α,β-unsaturated aldehydes in high yield and enantioselectivity. New insights into the mechanism of this reaction have resulted in a significant reduction in reagent stoichiometry, enabling the use of precious alkynes and avoiding the use of excess dimethylzinc. The enantioenriched propargylic alcohols from this reaction serve as versatile synthetic intermediates and have enabled efficient syntheses of several complex natural products. A precious few: A general and practical zinc-catalyzed enantioselective alkyne addition methodology is reported (see scheme). New insights into the mechanism of this reaction have resulted in a significant reduction in reagent stoichiometry, enabling the use of precious alkynes and avoiding the use of excess dimethylzinc. This methodology has enabled the efficient synthesis of several complex natural products.

BIPOLAR TRANS CAROTENOID SALTS AND THEIR USES

The invention relates to trans carotenoid salt compounds, methods for making them, methods for solubilizing them and uses thereof. These compounds are useful in improving diffusivity of oxygen between red blood cells and body tissues in mammals including humans.

Bipolar trans carotenoid salts and their uses

The invention relates to trans carotenoid salt compounds, methods for making them, methods for solubilizing them and uses thereof. These compounds are useful in improving diffusivity of oxygen between red blood cells and body tissues in mammals including humans.

Synthesis of isotopically labelled L-phenylalanine and L-tyrosine

A synthetic route to stable-isotope-substituted L-phenylalanine is presented, which allows the introduction of 13C, 15N, and deuterium labels at any position or combination of positions. For labelling of the aromatic ring, a synthetic route to ethyl benzoate (or benzonitrile) has been developed, based on the electrocyclic ring-closure of a 1,6-disubstituted hexatriene system, with in situ aromatization by elimination of one (amino) substituent. Several important (highly isotopically enriched) synthons have been prepared, namely benzonitrile, benzaldehyde, ethyl benzoate, and ethyl diphenyloxyacetate. Labelled L-phenylalanines have been synthesized from both aromatic precursors by initial conversion into sodium phenylpyruvate and subsequent transformation of this intermediate into the L-α-amino acid by an enzymatic reductive amination reaction. In this manner, highly enriched phenylalanines are obtained on the 10-gram scale and with high enantiomeric purities (≥ 99% ee). The method has been validated by the synthesis of [1'13C]-L-Phe and [2-D]-L-Phe. In addition, two methods are described for the introduction of isotopes into L-tyrosine starting from the isotopically enriched precursors benzonitrile and ethyl benzoate.