57449-30-6

Basic information

• Product Name: (2E)-but-2-en-1-yl (3S,4S,5S)-3,4,5-trihydroxy-6-oxocyclohex-1-ene-1-carboxylate
• Synonyms: CROTONYLOXYMETHYL-4,5,6-TRIHYDRO-OXYCYCLOHEX-2-ENONE ;2-Butenoic acid, [(3R,4R,5R)-3,4,5-trihydroxy-6-oxo-1-cyclohexen-1-yl]methyl ester
• CAS NO: 57449-30-6
• Molecular Formula: C₁₁H₁₄O₆
• Molecular Weight: 242.2253
• Mol File: 57449-30-6.mol
• Article Data: 10

Chemical Properties

• Melting Point: 181°C
• Boiling Point: 432.6°C at 760 mmHg
• Flash Point: 168.6°C
• Density: 1.459g/cm³
• Vapor Pressure: 2.67E-09mmHg at 25°C
• Refractive Index: 1.604
• CAS DataBase Reference: (2E)-but-2-en-1-yl (3S,4S,5S)-3,4,5-trihydroxy-6-oxocyclohex-1-ene-1-carboxylate(CAS DataBase Reference)
• NIST Chemistry Reference: (2E)-but-2-en-1-yl (3S,4S,5S)-3,4,5-trihydroxy-6-oxocyclohex-1-ene-1-carboxylate(57449-30-6)
• EPA Substance Registry System: (2E)-but-2-en-1-yl (3S,4S,5S)-3,4,5-trihydroxy-6-oxocyclohex-1-ene-1-carboxylate(57449-30-6)

Safety Data

• Hazardous Substances Data: 57449-30-6(Hazardous Substances Data)

Usage

Description

(2E)-but-2-en-1-yl (3S,4S,5S)-3,4,5-trihydroxy-6-oxocyclohex-1-ene-1-carboxylate is a complex organic compound featuring a buten-1-yl group attached to a cyclohexene carboxylate moiety. This molecule is characterized by the presence of three hydroxyl groups at positions 3, 4, and 5, and a keto group at position 6 on the cyclohexene ring. Its unique structure suggests potential applications in various chemical and pharmaceutical fields, although further research is necessary to fully explore its properties and uses.

Uses

Used in Chemical Synthesis:
(2E)-but-2-en-1-yl (3S,4S,5S)-3,4,5-trihydroxy-6-oxocyclohex-1-ene-1-carboxylate is used as a key intermediate in the synthesis of various complex organic molecules. Its unique structure allows for versatile chemical reactions, making it a valuable component in the creation of pharmaceuticals, agrochemicals, and other specialty chemicals.
Used in Pharmaceutical Development:
In the pharmaceutical industry, (2E)-but-2-en-1-yl (3S,4S,5S)-3,4,5-trihydroxy-6-oxocyclohex-1-ene-1-carboxylate is used as a potential therapeutic agent. Its specific functional groups and stereochemistry may contribute to its biological activity, offering opportunities for the development of new drugs with novel mechanisms of action.
Used in Material Science:
(2E)-but-2-en-1-yl (3S,4S,5S)-3,4,5-trihydroxy-6-oxocyclohex-1-ene-1-carboxylate may also find applications in material science, where its structural features could be leveraged to create new materials with unique properties. These materials could have uses in coatings, adhesives, or as components in advanced composites.
Further research is essential to determine the full scope of applications for (2E)-but-2-en-1-yl (3S,4S,5S)-3,4,5-trihydroxy-6-oxocyclohex-1-ene-1-carboxylate, as its complex structure and potential reactivity may unlock new possibilities across various industries.

Upstream product

• 128044-87-1 (1R,2R,3S)-3-O-tert-Butyldimethylsilyl-1,2-O-cyclohexylidene-5-methoxycarbonyl-4-cyclohexen-1,2,3-triol 
• 128044-89-3 (1R,2S,3S,4R,5R)-2-O-Acetyl-3-O-tert-butyldimethylsilyl-4,5-O-cyclohexylidene-1-methoxycarbonyl-cyclohexan-1,2,3,4,5-pentaol 
• 128044-90-6 (1R,2R,3S,4R)-4-O-Acetyl-3-O-tert-butyldimethylsilyl-1,2-O-cyclohexylidene-5-methoxycarbonyl-5-cyclohexen-1,2,3,4-tetraol 
• 128044-92-8 (1R,2R,3S,4R)-3-O-tert-Butyldimethylsilyl-5-crotonyloxymethyl-1,2-O-cyclohexylidene-5-cyclohexen-1,2,3,4-tetraol 
• 128044-88-2 (1R,2R,3S,4R,5R)-3-O-tert-Butyldimethylsilyl-1,2-O-cyclohexylidene-5-methoxycarbonyl-cyclohexane-1,2,3,4,5-pentaol 
• 128044-91-7 (1R,2R,3S,4R)-3-O-tert-Butyldimethylsilyl-1,2-O-cyclohexylidene-5-hydroxymethyl-5-cyclohexen-1,2,3,4-tetraol 
• 193888-32-3 3,4-O-cyclohexylidene-5-oxoquinate 
• 123994-31-0 methyl (3S,4R,5R)-3-O-benzoyl-4,5-O-cyclohexylidene-3,4,5-trihydroxycyclohec-1-ene-1-carboxylate 
• 128044-86-0 Methyl 4,5-O-cyclohexylidene-3-didehydro-4-epi-shikimate 
• 35949-53-2 (-)-4,5-cyclohexylidenequinic acid lactone 
• 77-95-2 D-(-)-quinic acid 
• 101246-15-5 4L-(4,5,6/0)-6-O-<(tert-butyl)dimethylsilyl>-4,5,6-trihydroxy-2-hydroxymethyl-4,5-O-isopropylidenecyclohex-2-enone 
• 101246-13-3 4L-(4,5,6/0)-6-O-<(tert-butyl)dimethylsilyl>-4,5,6-trihydroxy-4,5-O-isopropylidene-cyclohex-2-enone 

Downstream Products

• 57449-32-8 (4R,5R,6R)-4,5,6-Trihydroxy-2-(2-hydroxy-ethylsulfanylmethyl)-cyclohex-2-enone 
• 57449-33-9 (4R,5R,6R)-2-(4-Bromo-phenylsulfanylmethyl)-4,5,6-trihydroxy-cyclohex-2-enone 
• 57449-31-7 (E)-But-2-enoic acid 2,3,5-triacetoxy-benzyl ester 
• 40980-53-8 (-)-gabosine C 

Relevant articles and documents

Enantiospecific Synthesis of 2-Crotonyloxy-(4R,5R,6R)-4,5,6-trihydroxycyclohex-2-enone (COTC) from Quinic Acid

A thirteen-step synthesis of the glyoxalase I inhibitor COTC (2-crotonyloxy-(4R,5R,6R)-4,5,6-trihydroxycyclohex-2-enone) from quinic acid is described.

Arene cis-dihydrodiols: Useful precursors for the preparation of analogues of the anti-tumour agent, 2-crotonyloxymethyl-(4R,5R,6R)-4,5,6-trihydroxycyclohex-2-enone (COTC)

The synthesis of 6-epi-COTC, a diastereoisomer of Streptomyces metabolite 2-crotonyloxymethyl-(4R,5R,6R)-4,5,6-trihydroxycyclohex-2-enone (COTC), is described. The anti-cancer activities of the novel analogue, in racemic and enantiomerically pure forms, a

A new synthesis of the Glyoxalase-I inhibitor COTC

A stereoselective, chiral synthesis of the glyoxalase I inhibitor 2- crotonyloxymethyl-(4R,5R,6R)-4,5,6-trihydroxycyclohex-2-enone 1 (COTC) from a simple derivative of (-)-quinic acid is described. (C) 2000 Elsevier Science Ltd.