79232-29-4

Basic information

• Product Name: alliacol A
• Synonyms: alliacol A;(1aR,2R,7aS)-2α,9,9-Trimethyl-4aβ-hydroxy-5-methylene-2,3,4,4a,5,6,9,9aα-octahydro-8H-oxireno[1,7a]indeno[3a,4-b]furan-6-one;(1aR,2R,7aS,9aR)-3,4,4a,5,9,9a-Hexahydro-4aβ-hydroxy-2,9,9-trimethyl-5-methylene-2H,8H-oxireno[1,7a]indeno[3a,4-b]furan-6-one;Alliacolide II
• CAS NO: 79232-29-4
• Molecular Formula: C15H20O4
• Molecular Weight: 264.3169
• Mol File: 79232-29-4.mol

Chemical Properties

• Boiling Point: 451.9°C at 760 mmHg
• Flash Point: 171.4°C
• Appearance: /
• Density: 1.28g/cm³
• Vapor Pressure: 4.58E-10mmHg at 25°C
• Refractive Index: 1.574
• CAS DataBase Reference: alliacol A(CAS DataBase Reference)
• NIST Chemistry Reference: alliacol A(79232-29-4)
• EPA Substance Registry System: alliacol A(79232-29-4)

Safety Data

• Hazardous Substances Data: 79232-29-4(Hazardous Substances Data)

Usage

InChI:InChI=1/C15H20O4/c1-8-5-6-13(17)9(2)10(16)18-14(13)7-12(3,4)11-15(8,14)19-11/h8,11,17H,2,5-7H2,1,3-4H3

Upstream product

• 122689-68-3 Methanesulfonic acid (1R,7R)-2,2,7-trimethyl-4-oxo-2,3,4,5,6,7-hexahydro-1H-inden-1-yl ester 
• 79232-32-9 12-hydroxyalliacolide 
• 115025-14-4 (1RS,7RS)-1-Acetoxy-2,3,4,5,6,7-hexahydro-2,2,7-trimethyl-1H-inden-4-one 
• 122689-67-2 (1RS,7RS)-2,3,4,5,6,7-Hexahydro-1-hydroxy-2,2,7-trimethyl-1H-inden-4-one 
• 167101-23-7 3-[2-(2-[1,3]Dioxan-2-yl-ethyl)-[1,3]dithian-2-yl]-cyclopentanone 
• 167101-24-8 1,2,3,3a,5,6-Hexahydro-4,4-(1,3-propanediyldithio)-4H-inden-1-one 

Downstream Products

• 66389-08-0 (+/-)-alliacolide 

Relevant articles and documents

Structures of Some New Sesquiterpenoid Metabolites of Marasmius alliaceus

The sesquiterpenoids, alliacolide II (alliacol A)(2), 12-hydroxydehydroalliacolide (alliacol B) (3), 12-noralliacolide (5), 11- and 12-hydroxyalliacolide (6) and (7), respectively, and alliacolide (8) have been isolated from Marasmius alliaceus and their structures established by a combination of their spectra and chemistry.

A Stereoselective Total Synthesis of (+/-)-Alliacol A and Congeners of Marasmius Alliaceus

Synthesis of alliacolide (1), alliacol A (2), and 12-noralliacolide (4), members of the alliacane family of sesquiterpene lactones, was accomplished through both syn- and anti-modes of intramolecular SN' displacement.Two routes to 12-noralliacolide (4) are presented, which contrast brevity and efficiency in stereoselection (i.e. 14 -> 16/17 versus 37a/b -> 38).Since both routes culminate in C-ring annulation, introduction of the correct stereochemical arrangement relied heavily on the structural features of the hydrindane (AB) precursor(s).Choice of the proper AB system 24 facilitated production of tetrahydrofuran 38.With the full skeleton in place, 38 was efficiently epoxidized and oxidized to 4. 12-Noralliacolide (4) served as an appropriate relay substrate for conversion to alliacol A (2) and several other alliacanes.

TOTAL SYNTHESIS OF (+/-)-12-NORALLIACOLIDE, (+/-)-ALLIACOL A AND (+/-)-ALLIACOLIDE

The title compounds were prepared via a "one-pot" γ-lactone annulation sequence in which dilithium acetate functions as a bis-nucleophile, first at carbonyl and then at hindered allylic sulfonate centers (SN' orientation).