683276-44-0

Basic information

• Product Name: 4H-Cyclopenta-1,3-dioxol-4-ol, 3a,6a-dihydro-2,2-dimethyl-, (3aS,6aR)- (9CI)
• Synonyms: 4H-Cyclopenta-1,3-dioxol-4-ol, 3a,6a-dihydro-2,2-dimethyl-, (3aS,6aR)- (9CI)
• CAS NO: 683276-44-0
• Molecular Formula: C₈H₁₂O₃
• Molecular Weight: 156.17908
• Product Categories: ALCOHOL
• Mol File: 683276-44-0.mol

Chemical Properties

• Appearance: /
• CAS DataBase Reference: 4H-Cyclopenta-1,3-dioxol-4-ol, 3a,6a-dihydro-2,2-dimethyl-, (3aS,6aR)- (9CI)(CAS DataBase Reference)
• NIST Chemistry Reference: 4H-Cyclopenta-1,3-dioxol-4-ol, 3a,6a-dihydro-2,2-dimethyl-, (3aS,6aR)- (9CI)(683276-44-0)
• EPA Substance Registry System: 4H-Cyclopenta-1,3-dioxol-4-ol, 3a,6a-dihydro-2,2-dimethyl-, (3aS,6aR)- (9CI)(683276-44-0)

Safety Data

• Hazardous Substances Data: 683276-44-0(Hazardous Substances Data)

Upstream product

• 369647-25-6 (1S,2S,3R)-(-)-1-(2,2-dimethyl-5-vinyl-1,3-dioxolan-4-yl)-(S)-2-propen-1-ol 
• 141436-58-0 (-)-(1R)-1-[(4R,5S)-5-((1S)-1-hydroxyallyl)-2,2-dimethyl[1,3]dioxolan-4-yl]ethane-1,2-diol 
• 503302-88-3 (1R,4'S,5'R)-1-(2',2'-dimethyl-5'-vinyl[1',3']dioxo-4'-yl)prop-2-en-1-ol 
• 50600-40-3 (3aS,4S,6aR)-4-(iodomethyl)-6-methoxy-2,2-dimethyltetrahydrofuro[3,4-d][1,3]dioxole 
• 4099-85-8 methyl 2,3-O-isopropylidene-D-ribofuranoside 
• 155934-55-7 (4R,5R)-2,2-dimethyl-5-vinyl-[1,3]dioxolane-4-carbaldehyde 
• 67814-68-0 2,3-O-isopropylidene-D-ribofuranose 
• 683276-43-9 (4R,5R)-1-(2,2-dimethyl-5-vinyl-[1,3]dioxolan-4-yl)prop-2-en-1-ol 

Downstream Products

• 132575-63-4 (3aR,6R,6aR)-6-(hydroxymethyl)-2,2-dimethyldihydro-3aH-cyclopenta[d][1,3]dioxol-4(5H)-one 
• 145307-55-7 (2S,3R,4R)-4-t-butyldimethylsiloxymethyl-2,3-isopropylidenedioxycyclopentanone 
• 1053260-67-5 (S)-4-(2-{[(3aR,4R,6R,6aS)-6-(6-Amino-purin-9-yl)-2,2-dimethyl-tetrahydro-cyclopenta[1,3]dioxol-4-ylmethyl]-methyl-amino}-ethyl)-5-oxo-oxazolidine-3-carboxylic acid benzyl ester 
• 698999-19-8 (3aR,6R,6aR)-2,2-dimethyl-6-vinyltetrahydro-4H-cyclopenta[d]-[1,3]-dioxol-4-one 
• 173346-41-3 Toluene-4-sulfonic acid (3aR,4R,6R,6aS)-6-(6-amino-purin-9-yl)-2,2-dimethyl-tetrahydro-cyclopenta[1,3]dioxol-4-ylmethyl ester 
• 19186-33-5 aristeromycin 
• 115509-13-2 (3aR,6aR)-2,2-Dimethyl-3a,6a-dihydro-cyclopenta[1,3]dioxol-4-one 

Relevant articles and documents

A General Biomimetic Hetero-Diels-Alder Approach to the Core Skeletons of Xenovulene A and the Sterhirsutins A and B

A biomimetic, regio- and stereoselective approach to the 5,6,11-tricyclic core skeleton of xenovulene A, as well as sterhirsutins A and B, is described. The key steps are a biomimetic inverse-electron-demand hetero-Diels-Alder cycloaddition of α-humulene and a ribose-derived vinyl ketone, followed by acid-catalyzed rearrangement of the 1,3-dioxolane that neighbors the resultant cyclic enol ether.

Identification of a cytotoxic molecule in heat-modified citrus pectin

Modified forms of citrus pectin possess anticancer properties. However, their mechanism of action and the structural features involved remain unclear. Here, we showed that citrus pectin modified by heat treatment displayed cytotoxic effects in cancer cells. A fractionation approach was used aiming to identify active molecules. Dialysis and ethanol precipitation followed by HPLC analysis evidenced that most of the activity was related to molecules with molecular weight corresponding to low degree of polymerization oligogalacturonic acid. Heat-treatment of galacturonic acid also generated cytotoxic molecules. Furthermore, heat-modified galacturonic acid and heat-fragmented pectin contained the same molecule that induced cell death when isolated by HPLC separation. Mass spectrometry analyses revealed that 4,5-dihydroxy-2-cyclopenten-1-one was one cytotoxic molecule present in heat-treated pectin. Finally, we synthesized the enantiopure (4R,5R)-4,5-dihydroxy-2-cyclopenten-1-one and demonstrated that this molecule was cytotoxic and induced a similar pattern of apoptotic-like features than heat-modified pectin.

USE OF THE IRRITATING PRINCIPAL OLEOCANTHAL IN OLIVE OIL, AS WELL AS STRUCTURALLY AND FUNCTIONALLY SIMILAR COMPOUNDS

The invention provides oleocanthal analogs and methods of using oleocanthals in various formulations including, food additives; pharmaceuticals; cosmetics; animal repellants; and discovery tools for mammalian irritation receptor genes, gene products, alleles, splice variants, alternate transcripts and the like.

Synthesis of the potent anticancer agents ottelione A and ottelione B in both racemic and natural optically pure forms

(Chemical Equation Presented) The powerful antitumor agents ottelione A and B were synthesized in racemic form by a method that relies on selective ring closing metathesis. Optically pure natural (+)-ottelione A was then made from D-ribose, via an α-keto cyclopropane. A key feature of the route is that the cyclopropyl group controls the stereochemistry in the attachment of the ArCH2 unit and is then converted by the action of SmI2 into a vinyl group, so that the substituents on the resulting five-membered ring have the required trans relationship. Epimerization of an intermediate gave access by the same method to the trans ring fused isomer (-)-ottelione B.

Preparation of carbocyclic S-adenosylazamethionine accompanied by a practical synthesis of (-)-aristeromycin

For the preparation of a carbocyclic nitrogen analogue of S-adenosylmethionine (carba-AdoazaMet, 4), a practical synthesis of (-)-aristeromycin (7) has been developed using variations of literature procedures. This approach called for a stereospecific synthesis of (3aR,6aR)-2,2-dimethyl-3a, 6a-dihydrocyclopenta[1,3]dioxol-4-one ((4R, 5R)-4,5-O-isopropylidene-2-cyclopentenone) (8), which was achieved by modifying reported procedures from D-(-)-ribose.