22555-57-3

Basic information

• Product Name: 2-exo-hydroxy-1-methyl-4-(1-methylethyl)-7-oxabicyclo[2.2.1]heptane
• Synonyms: 2-exo-hydroxy-1-methyl-4-(1-methylethyl)-7-oxabicyclo[2.2.1]heptane
• CAS NO: 22555-57-3
• Molecular Weight: 170.252
• Mol File: 22555-57-3.mol
• Article Data: 4

Chemical Properties

• CAS DataBase Reference: 2-exo-hydroxy-1-methyl-4-(1-methylethyl)-7-oxabicyclo[2.2.1]heptane(CAS DataBase Reference)
• NIST Chemistry Reference: 2-exo-hydroxy-1-methyl-4-(1-methylethyl)-7-oxabicyclo[2.2.1]heptane(22555-57-3)
• EPA Substance Registry System: 2-exo-hydroxy-1-methyl-4-(1-methylethyl)-7-oxabicyclo[2.2.1]heptane(22555-57-3)

Safety Data

• Hazardous Substances Data: 22555-57-3(Hazardous Substances Data)

Upstream product

• 111613-34-4 2-Oxo-(1R,4S)-cineole 
• 470-67-7 1,4-cineole 
• 2438-10-0 (+)-terpinen-4-ol 
• 20126-76-5 (-)-terpinen-4-ol 

Downstream Products

• 22555-57-3 2(R)-endo-hydroxy-1,4-cineole 
• 117306-79-3 2(R)-endo-hydroxy-1(R),4(S)-cineole (R)-(-)-O-acetylmandelate 
• 117306-77-1 2(R)-endo-hydroxy-1(R),4(S)-cineole (S)-(+)-O-acetylmandelate 
• 117306-78-2 2(S)-endo-hydroxy-1(S),4(R)-cineole (S)-(+)-O-acetylmandelate 
• 87818-31-3 2-exo-[(2-methylphenyl)methoxy]-1-methyl-4-(1-methylethyl)-7-oxabicyclo[2.2.1]heptane 
• 117229-40-0 2(S)-exo-hydroxy-1(R),4(S)-cineole (S)-(+)-O-acetylmandelate 

Relevant articles and documents

Hydroxylation of Deuterated 1,4-Cineoles by Bacillus cereus

The stereochemistry and mechanism of 1,4-cineole hydroxylation by the cytochrome P-450-containing strain of Bacillus cereus UI-1477 was examined using specifically deuterated substrates.Stereospecifically deuterated 1,4-cineoles were synthesized by Wolff-Kishner reductions of enantiomeric 2-oxo-1,4-cineoles, and by Barton-McCombie elimination of the alcohol functional group of 2-hydroxy-2-deutero-(1R,4S)-cineole.Products obtained from hydroxylations of 2-deutero-(1R,4S)-cineole and enentiomeric 2,2,3,3-tetradeutero- and 2,2,3-trideutero-1,4-cineoles were isolated and characterized by gas chromatography/mass spectrometry and by 1H- and 2H-NMR spectroscopy.Deuterium at the site which is oxygenated does not change hydroxylation stereospecificity, but it dramatically shifts the relative ratios of 2-endo- and 2-exo-alcohol products formed.Analysis of cineole alcohols obtained by microbial hydroxylation of multiply-deuterated-1,4-cineoles indicated that the starting materials contained deuterium at both the 2- and 6-positions, suggesting that a 2,6-proton migration occurs during the Wolff-Kishner reduction of enantiomerically pure 2-oxo-1,4-cineoles.Ratios of cineole alcohols formed from monodeuterated-1,4-cineoles reveal the likehood of a two-step machanism involving nonspecific hydrogen atom removal followed by stereospecific hydroxylation.

PREPARATION OF BIOLOGICALLY ACTIVE SUBSTANCES AND ANIMAL AND MICROBIAL METABOLITES FROM MENTHOLS, CINEOLES AND KAURANES

Six monoterpenoids, l-menthol, l-menthyl acetate, iso-menthol, neo-menthol, 1,4-cineole and 1,8-cineole and one diterpene hydrocarbon, ent-kaurene were oxidized by meta-chloroperbenzoic acid or dry ozone to give various hydroxylated products and their structures elucidated by NMR spectroscopy.Some hydroxylated menthols showed plant growth inhibitory and strong mosquito repellent activity.Among the hydroxylated cineoles, microbial and animal metabolites of cineoles were included.From ent-kauranes, a plant growth inhibitory diterpene alcohol, (-)-16α-hydroxy kaurane was obtained along with 16α-kauran-13α-ol.