113757-64-5

Basic information

• Product Name: 2,4-Pyrrolidinedione, 3-(1-hydroxyethylidene)-5-methyl-, [S-(Z)]- (9CI)
• Synonyms: 2,4-Pyrrolidinedione, 3-(1-hydroxyethylidene)-5-methyl-, [S-(Z)]- (9CI)
• CAS NO: 113757-64-5
• Molecular Formula: C7H9NO3
• Molecular Weight: 155.15126
• Product Categories: ACETYLGROUP
• Mol File: 113757-64-5.mol

Chemical Properties

• Appearance: /
• CAS DataBase Reference: 2,4-Pyrrolidinedione, 3-(1-hydroxyethylidene)-5-methyl-, [S-(Z)]- (9CI)(CAS DataBase Reference)
• NIST Chemistry Reference: 2,4-Pyrrolidinedione, 3-(1-hydroxyethylidene)-5-methyl-, [S-(Z)]- (9CI)(113757-64-5)
• EPA Substance Registry System: 2,4-Pyrrolidinedione, 3-(1-hydroxyethylidene)-5-methyl-, [S-(Z)]- (9CI)(113757-64-5)

Safety Data

• Hazardous Substances Data: 113757-64-5(Hazardous Substances Data)

Usage

Also known as

L-erythrulose

Common uses

Tanning products, cosmetics, sunless tanning lotions and sprays

Chemical classification

Ketose sugar

Skin reaction

Reacts with amino acids in the stratum corneum, producing melanoidins, a brown pigment

Tanning alternative

Considered a safe alternative to traditional tanning methods

Other uses

Flavor enhancer and sweetener in the food industry

Upstream product

• 64401-29-2 (3-oxobutyryl)alanine methyl ester 
• 1048681-14-6 S-phenyl (S)-2-(3-oxobutanamido)propanethioate 
• 1048681-17-9 (S)-S-(2-acetamidoethyl) 2-(3-oxobutanamido)propanethioate 
• 3103-37-5 (S)-2-(3-oxobutanamido)propanoic acid 

Relevant articles and documents

Insights into pyrroindomycin biosynthesis reveal a uniform paradigm for tetramate/tetronate formation

The natural products pyrroindomycins (PYRs), active against various drug-resistant pathogens, possess a characteristic, cyclohexene ring spiro-linked tetramate moiety. In this study, investigation into PYR biosynthesis revealed two new proteins, both of which, phylogenetically distinct from but functionally substitutable to each other in vivo, individually catalyze a Dieckmann cyclization in vitro for converting an N-acetoacetyl-l- alanyl thioester into a tetramate. Their counterparts are commonly present in the biosynthetic pathways of spiro and polyether tetronates, supporting a uniform paradigm for tetronate/tetramate formation, which features an enzymatic way to generate the C-X (X = O or N) bond first and the C-C bond next in building of the 5-membered heterocycle.

Discovery of a new family of dieckmann cyclases essential to tetramic acid and pyridone-based natural products biosynthesis

Bioinformatic analyses indicate that TrdC, SlgL, LipX2, KirHI, and FacHI belong to a group of highly homologous proteins involved in biosynthesis of actinomycete-derived tirandamycin B, streptolydigin, ?±-lipomycin, kirromycin, and factumycin, respectively. However, assignment of their biosynthetic roles has remained elusive. Gene inactivation and complementation, in vitro biochemical assays with synthetic analogues, point mutations, and phylogenetic tree analyses reveal that these proteins represent a new family of Dieckmann cyclases that drive tetramic acid and pyridone scaffold biosynthesis.

RELATIONSHIPS BETWEEN THE STRUCTURE AND THE PHYTOTOXICITY OF THE FUNGAL TOXIN TENUAZONIC ACID

Tenuazonic acid (3-acetyl 5-sec-butyl pyrrolidine-2,4-dione) is a metabolite produced by the fungal pathogen of rice Pyricularia oryzae.It inhibits growth of plants by interferring with protein synthesis at the ribosome level.We have synthesized analogues of tenuazonic acid with various substituents at C-3 and C-5.Substituents at C-5 other than sec-butyl or n-propyl, decrease the phytotoxicity of the analogues.But substitutions at C-3 abolish the toxicity.Thus, tenuazonic acid seems to have the optimal structure for phytotoxicity.Tenuazonic acid induces rice leaf defence reactions (browning) of reactive varieties which are resistant to P. oryzae.Some of the analogues synthesized have a low level of phytotoxicity and are able to induce this leaf browning of the reactive rice varieties.Thus different structural features are required for phytotoxicity and for leaf browning.Key Word Index - Tenuazonic acid; pyrrolidine-2,4-diones; rice; phytotoxicity; Pyricularia oryzae; structure-activity.