66432-53-9

Basic information

• Product Name: 2,3,4,6-TETRA-O-ACETYL LINAMARIN
• Synonyms: 2-(2,3,4,6-TETRA-O-ACETYL-BETA-D-GLUCOPYRANOSYLOXY)ISOBUTYRONITRILE;2,3,4,6-TETRA-O-ACETYL LINAMARIN;2-(2,3,4,6-Tetra-O-acetyl-b-D-glucopyranosyloxy)isobutyronitrile;2-(2,3,4,6-Tetra-O-acetyl--D-glucopyranosyloxy)isobutyronitrile;LinaMarin Tetraacetate
• CAS NO: 66432-53-9
• Molecular Formula: C₁₈H₂₅NO₁₀
• Molecular Weight: 415.39
• Product Categories: Carbohydrates & Derivatives
• Mol File: 66432-53-9.mol

Chemical Properties

• Melting Point: 140-141°C
• Boiling Point: 484.4±45.0 °C(Predicted)
• Appearance: /
• Density: 1.26±0.1 g/cm3(Predicted)
• Storage Temp.: Hygroscopic, -20°C Freezer, Under Inert Atmosphere
• Solubility: Chloroform, Ethyl Acetate
• CAS DataBase Reference: 2,3,4,6-TETRA-O-ACETYL LINAMARIN(CAS DataBase Reference)
• NIST Chemistry Reference: 2,3,4,6-TETRA-O-ACETYL LINAMARIN(66432-53-9)
• EPA Substance Registry System: 2,3,4,6-TETRA-O-ACETYL LINAMARIN(66432-53-9)

Safety Data

• Hazardous Substances Data: 66432-53-9(Hazardous Substances Data)

Usage

Uses

Used in Organic Synthesis:
2,3,4,6-TETRA-O-ACETYL LINAMARIN is used as a synthetic intermediate for the development of various organic compounds. Its application in this field is due to its unique chemical structure, which allows for further functionalization and modification to create a wide range of products with diverse properties and applications.
Used in Pharmaceutical Industry:
In the pharmaceutical industry, 2,3,4,6-TETRA-O-ACETYL LINAMARIN is used as a key component in the synthesis of potential drug candidates. Its versatility in organic synthesis enables the development of new molecules with therapeutic properties, contributing to the discovery of novel treatments for various diseases and medical conditions.
Used in Chemical Research:
2,3,4,6-TETRA-O-ACETYL LINAMARIN is also utilized in chemical research as a model compound for studying various reaction mechanisms and exploring new synthetic routes. Its use in this context aids in advancing the understanding of organic chemistry and contributes to the development of innovative synthetic strategies and techniques.
Used in Material Science:
In the field of material science, 2,3,4,6-TETRA-O-ACETYL LINAMARIN may be employed as a precursor for the development of novel materials with specific properties, such as improved stability, reactivity, or selectivity. Its application in this area can lead to the creation of new materials with potential applications in various industries, including electronics, energy, and environmental protection.

Upstream product

• 74808-10-9 O-(2,3,4,6-Tetra-O-acetyl-α-D-glucopyranosyl)trichloroacetimidate 
• 207512-69-4 2-(2,3,4,6-tetra-O-acetyl-β-D-glucopyranosyloxy)isobutyramide 
• 554-35-8 linamarin 
• 108-24-7 acetic anhydride 

Downstream Products

• 554-35-8 linamarin 

Relevant articles and documents

CYANOHYDRIN GLYCOSIDES OF PASSIFLORACEAE

Barterin, a classical cyclopentenoid cyanohydrin glucoside, was shown to be (1S,4S)-1-(β-D-glucopyranosyloxy)-4-hydroxy-2-cyclopentene-1-carbonitrile, being thus identical with tetraphyllin B, contrary to previous statements in the literature.Cyanohydrin glycosides from Adenia dinklagei, A. epigea, A. firingalavensis, A. frutescens, A. hastata, A. letouzeyi, A. spinosa, Passiflora coriacea, P. subpeltata, P. warmingii and Smeathmannia pubescens were isolated and identified.A summary of the present knowledge of distribution of cyanohydrin glycosides in Passifloraceae shows clear differences between the two chief genera, Adenia and Passif lora.Thus, the former genus appears to be dominated by β-D-glucopyranosides of 2-cyclopenten-1-one and 4-hydroxy-2-cyclpenten-1-one cyanohydrin; the glycosides generally occur as pairs having enantiomeric aglycones and the cyclopentene ring is usually trans-1,4-dioxygenated.By contrast, the pattern of cyanohydrin glycosides of Passiflora appears to be highly diversified, comprising valine or isoleucine-derived glycosides as well as cyclopentenoid glycosides, including more elaborate forms than those found in Adenia.The origin of epilotaustralin, possibly arising from the (3R)-epimer of L-isoleucine, is briefly discussed.Key Word Index- Adenia sp.; Passiflora sp.; Smeathmannia sp.; Passifloraceae; barterin; cyclopentenoid cyanohydrin glycosides; linamarin; lotaustralin; epilotaustralin; alloisoleucine.

Cyanogenic and non-cyanogenic glycosides from Manihot esculenta (euphorbiaceae)

A novel cyanogenic glycoside, 2-((6-0-(β-D-apiofuranosyl)-β- D-glucopyranosyloxy)-2-methylbutanenitrile, I, three novel non- cyanogenic glycosides, (2S)-((6-0-(β-D-apiofuranosyI)-β-D-gluco- pyranosyloxy) butane, 2; 2-((6-0-(β-D-apiofuranosyl)-β-D-gluco- pyranosyloxy) propane, 3, ethyl p-D-glucopyranosidc, 4, two known cyanogenic glycosides, (R)-2-(β-D-Glucopyranosyloxy)-2- methyl butanenitrile (lotaustralin), 5, 2-(β-D-Glucopyranosyloxy)- 2-methylpropane nitrile (linamarin), 6 have been isolated from ethanolic extract of the fresh rootcortex of Manihot esculenta. Lotaustralin and linamarin and two flavonoid glycosides, kaempferol-3-O- rutinosidc, 7 and quercctin-3-O-rutinoside, 8 have been isolated from the methanol extract of the fresh leaves of the same plant.

Activated dimethyl sulfoxide dehydration of amide and its application to one-pot preparation of benzyl-type perfluoroimidates

Various types of primary amides were treated under an activated dimethyl sulfoxide (DMSO) species, (COCl)2-DMSO and Et3N, as a dehydrating agent to obtain nitriles in excellent yield. This dehydration system was extended to a one-pot preparation of perfluoroimidates via volatile perfluoronitriles from perfluoroamides. Fifteen benzyl-type perfluoroimidates can be prepared in 70-90% yield as more stable imidates than the trichloro analogue. MPM- and DMPM-perfluoroimidates can be used to protect alcohols in place of the trichloroacetimidate with excellent chemical properties and in comparable yields.

Facile Synthesis of Cyanogen Glycosides (R)-Prunasin, Linamarin and (S)-Heterodendrin

A facile synthetic route is described to cyanogenic glycosides (R)-prunasin, linamarin and (S)-heterodendrin from O-(2,3,4,6-tetra-O-acetyl-α-D-glucopyranosyl)trichloroacetimidate and the corresponding α-hydroxyamides by a 3-step reaction of glycosylation, cyanohydrin formation by dehydration of carboxamides, and deprotection.

CYANOGENIC AND NON-CYANOGENIC GLYCOSIDES FROM MANIHOT ESCULENTA

In addition to lotaustralin and linamarin, a novel cyanogenic glycoside, 2-((6-O-(β-D-apiofuranosyl)-β-D-glucopyranosyl)oxy)-2-methylbutanenitrile, two novel non-cyanogenic glycosides, (2S)-((6-O-(β-D-apiofuranosyl)-β-D-glucopyranosyl)oxy)butane and 2-((6-O-(β-D-apiofuranosyl)-β-D-glucopyranosyl)oxy)propane, and a simple non-cyanogenic glycoside, ethyl β-D-glucopyranoside, were isolated from an ethanolic extract of the fresh root cortex of manihot esculenta.From a methanolic extract of the fresh leaves of this species lotaustralin and linamarin, and two flavonoid glycosides, kaempferol-3-O-rutinoside and quercetin-3-O-rutinoside were isolated. - Keywords: Manihot esculenta; Euphorbiaceae; cassava; roots; leaves; cyanogenic glycosides; non-cyanogenic glycosides; flavonoids.