56031-82-4

Upstream product

• 123-35-3 7-methyl-3-methene-1,6-octadiene 
• 37905-03-6 8-hydroxygeranyl acetate 
• 70238-37-8 (2'Z,6'E)-Essigsaeure-(8'-hydroxy-3',7'-dimethyl-2',6'-octadien-1'-yl)ester 
• 10090-80-9 9-acetoxy-8-hydroxy-p-menth-1-ene 
• 106-25-2 Nerol 
• 141-12-8 neryl acetate 
• 105-87-3 3,7-dimethyl-2E,6-octadien-1-yl acetate 
• 37905-02-5 (2E,6E)-3,7-dimethyl-8-oxoocta-2,6-dien-1-yl acetate 
• 28664-18-8 2-(4-methylcyclohex-3-en-1-yl)propan-2-yl 2,2,2-trifluoroacetate 
• 98-55-5 terpineol 
• 56086-28-3 (4R,8R)-8-hydroxy-p-menth-1-en-9-yl 4'-nitrobenzoate 
• 106113-26-2 (1S,2S,4R,8R)-1,2-dibromo-8-hydroxy-p-menth-9-yl 4'-nitrobenzoate 
• 5989-27-5 D-limonene 
• 10067-30-8 8,9-diacetoxy-p-menth-1-ene 

Downstream Products

• 107090-89-1 Toluene-4-sulfonic acid 2-hydroxy-2-(4-methyl-cyclohex-3-enyl)-propyl ester 
• 14675-11-7 p-menthane-8,9-diol 
• 98-55-5 terpineol 
• 72257-53-5 (-)-α2-acetyloxy-1,8-cineole 
• 72257-53-5 (+)-α2-acetyloxy-1,8-cineole 
• 18679-55-5 (+/-)-2-oxo-1,8-cineole 
• 18679-48-6 (+/-)-β2-hydroxy-1,8-cineole 
• 72257-53-5 cis-2-acetoxy-1,8-cineole 
• 72257-53-5 (+)-β2-acetyloxy-1,8-cineole 
• 72257-53-5 (-)-β2-acetyloxy-1,8-cineole 
• 72447-56-4 9-Hydroxycineole 
• 18679-48-6 2-endo-hydroxy-1,8-cineole ((1R,6R)-1,3,3-trimethyl-2-oxabicyclo-[2.2.2]octan-6-ol) 
• 72257-53-5 (+/-)-1,3,3-trimethyl-2-oxabicyclo[2.2.2]octan-6-ol acetate 
• 107090-89-1 (4R,8R)-8-hydroxy-p-menth-1-en-9-yl p-toluenesulfonate 

Relevant academic research and scientific papers

Traceless Silylation of β-C(sp3)-H Bonds of Alcohols via Perfluorinated Acetals

We report the silylation of primary C-H bonds located β to secondary and tertiary alcohols by exploiting perfluorinated esters as traceless directing groups. The conversion of a secondary or tertiary alcohol to a perfluoroalkyl ester and conversion of the ester to the corresponding silyl acetals by hydrosilylation allows for selective β-C(sp3)-H silylation catalyzed by the combination of [Ir(cod)OMe]2 and Me4Phen (3,4,7,8-tetramethyl-1,10-phenanthroline) to form 6-membered dioxasilinane. Tamao-Fleming oxidation of these dioxasilinane leads to 1,2 diols. The developed sequence was applied to a series of natural products containing hydroxyl groups.

Syntheses of chiral 1,8-cineole metabolites and determination of their enantiomeric composition in human urine after ingestion of 1,8-cineole- containing capsules

The chiral metabolites in human urine were investigated after ingestion of a 1,8-cineole (eucalyptol)-containing enterocoated capsule (Soledum). For identification of the various enantiomers the enantiomerically pure (-/+)-α2-hydroxy-1,8- cineole, (-/+)-β2-hydroxy-1,8-cineole, (-/+)-9-hydroxy-1,8-cineole, and (-/+)-2-oxo-1,8-cineole were prepared. To achievethis aim, after acetylation of the synthesized racemic 2-and 9-hydroxy-1,8-cineoles, pig liver esterase- or yeast-mediated hydrolysis provided the (-)-alcohols with their antipodal(+)-acetates with enantiomeric excess of 33-100 %. Dess-Martin periodinane oxidation of the alcohol (+)-α2-hydroxy-1,8-cineole, obtained by hydrolysis of the resolved acetate, provided the corresponding (+)-2-oxo-1,8-cineole, meanwhile the oxidation of (-)-α2-hydroxy-1,8-cineole gave (-)-2-oxo-1,8-cineole. Using these standards seven metabolites (+/-)-α2-hydroxy-1,8-cineole, (+/-)-β2-hydroxy-1,8-cineole, (+/-)-α3-hydroxycineole,(+/-)-3-oxo-1, 8-cineole, 4-hydroxy-1,8-cineole, 7-hydroxy-1,8-cineole, and (+/-)-9-hydroxy-1,8-cineole, all liberated from their glucuronides, were identified in urine by GCMS on a chiral stationary phase after consumption of 10 mg of 1,8-cineole. Metabolite screening using 2H3-1,8- cineol as the internal standard revealed (+/-)-α2-hydroxy-1,8-cineole as the predominant metabolite followed by (+/-)-9-hydroxy-1,8-cineole. Furthermore, the results showed that one enantiomer is always formed preferentially.

Superacidic cyclization of ω-hydroxygeraniol diacetate and ω-hydroxygeraniol benzyl ether acetate

Low-temperature superacidic cyclization of (E,E)-3,7-dimethylocta-2,6-diene-1,8-diol (ω-hydroxygeraniol) diacetate and (E,E)-8-acetoxy-1-benzyloxy-3,7-dimethylocta-2,6-diene leads to the same mixtures of two diastereomeric 9-acetoxy-8-hydroxy-p-menth-1-enes epimeric at the C(8) atom.

Halogenated Terpenoids. XXII. Uroterpenol. The C8 Stereochemistry

The two diastereoisomeric p-menth-1-ene-8,9-diols (uroterpenols) have been separated and crystallized.A crystallographic analysis of a dibromo derivative enables relative and absolute configurations to be assigned throughout the series.

Chemical Tranformation of Terpenoids. V. Acidic Conversions of 10-Hydroxygeraniol and 10-Hydroxynerol Derivatives Leading to Cyclic Monoterpenoids

Acid treatment of 1-O-acetyl-10-hydroxygeraniol (5a), 1-O-methyl-10-hydroxygeraniol (5b), 1-O-acetyl-10-hydroxynerol (6a), and 1-O-methyl-10-hydroxynerol (6b) was investigated under various conditions.It was found that treatment of 5a and 6a with HCOOH gave menth-1-ene-8,9-diol (7), while treatment of 5a, 5b, 6a, or 6b with BF3-etherate in CH2Cl2 furnished two menthofuran-type compounds (9, 10) and two bicyclooct-2-ene derivatives (17, 24).Both 9 and 10 were successfully converted to menthofuran (16) and 17 was converted to a bicyclooctenone derivative (23) which was a key intermediate for a synthesis of juvabione (27).Keywords - geraniol; nerol; 10-hydroxygeraniol; 10-hydroxynerol; 10-hydroxygeraniol derivative; 10-hydroxynerol derivative; uroterpenol; menthofuran; bicyclooct-2-ene derivative