494210-18-3

Basic information

• Product Name: 7-Oxabicyclo[2.2.1]heptan-2-ol,4-methyl-1-(1-methylethyl)-,(1S,2S,4S)-(9CI)
• Synonyms: 7-Oxabicyclo[2.2.1]heptan-2-ol,4-methyl-1-(1-methylethyl)-,(1S,2S,4S)-(9CI)
• CAS NO: 494210-18-3
• Molecular Formula: C10H18O2
• Molecular Weight: 170.25
• Product Categories: ISOPROPYL
• Mol File: 494210-18-3.mol
• Article Data: 3

Chemical Properties

• Appearance: /
• CAS DataBase Reference: 7-Oxabicyclo[2.2.1]heptan-2-ol,4-methyl-1-(1-methylethyl)-,(1S,2S,4S)-(9CI)(CAS DataBase Reference)
• NIST Chemistry Reference: 7-Oxabicyclo[2.2.1]heptan-2-ol,4-methyl-1-(1-methylethyl)-,(1S,2S,4S)-(9CI)(494210-18-3)
• EPA Substance Registry System: 7-Oxabicyclo[2.2.1]heptan-2-ol,4-methyl-1-(1-methylethyl)-,(1S,2S,4S)-(9CI)(494210-18-3)

Safety Data

• Hazardous Substances Data: 494210-18-3(Hazardous Substances Data)

Upstream product

• 470-67-7 1,4-cineole 
• 15249-34-0 Linalool oxide 
• 78-70-6 3,7-dimethylocta-1,6-dien-3-ol 
• 470-67-7 4-methyl-1-propan-2-yl-7-oxabicyclo[2.2.1]heptane 

Relevant articles and documents

Selective hydroxylation of 1,8- and 1,4-cineole using bacterial P450 variants

This study has evaluated the use of the P450 metalloenzymes CYP176A1, CYP101A1 and CYP102A1, together with engineered protein variants of CYP101A1 and CYP102A1, to alter the regioselectivity of 1,8- and 1,4-cineole hydroxylation. CYP176A1 was less selective for 1,4-cineole oxidation when compared to its preferred substrate, 1,8-cineole. The CYP102A1 variants significantly improved the activity over the WT enzyme for oxidation of 1,4- and 1,8-cineole. The CYP102A1 R47L/Y51F/A74G/F87V/L188Q mutant generated predominantly (1S)-6α-hydroxy-1,8-cineole (78% e.e.) from 1,8-cineole. Oxidation of 1,4-cineole by the CYP102A1 R47L/Y51F/F87A/I401P variant generated the 3α product in >90% yield. WT CYP101A1 formed a mixture metabolites with 1,8-cineole and very little product was generated with 1,4-cineole. In contrast the F87W/Y96F/L244A/V247L and F87W/Y96F/L244A variants of CYP101A1 favoured formation of 5α-hydroxy-1,8-cineole (>88%, 1S 86% e.e.) while the F87V/Y96F/L244A variant generated (1S)-6α-hydroxy-1,8-cineole in excess (90% regioselective, >99% e.e.). The CYP101A1 F87W/Y96F/L244A/V247L and F87W/Y96F/L244A mutants improved the oxidation of 1,4-cineole generating an excess of the 3α metabolite (1S > 99% e.e. with the latter). The CYP101A1 F87L/Y96F variant also improved the oxidation of this substrate but shifted the site of oxidation to the isopropyl group, (8-hydroxy-1,4-cineole). When this 8-hydroxy metabolite was generated in significant quantities desaturation of C8–C9 to the corresponding alkene was also detected.

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.