13835-32-0

Upstream product

• 18479-68-0 menth-1-en-9-ol 
• 99-33-2 3,5-dinitrobenoyl chloride 
• 287720-47-2 (2RS)-2-<(1R)-4-methylcyclohex-3-enyl>propanol 
• 5524-05-0 (2R,5R)-5-isopropenyl-2-methylcyclohexanone 
• 141277-82-9 ethyl (E)-2-[(2R,5R)-2-methyl-5-(prop-1-en-2-yl)cyclohexylidene]acetate 
• 5989-27-5 D-limonene 

Downstream Products

• 13835-75-1 (2R)-2-[(1R)-4-methylcyclohex-3-en-1-yl]propan-1-ol 
• 26462-77-1 (S)-2-Methyl-6-((R)-4-methyl-cyclohex-3-enyl)-heptan-4-one 
• 26462-78-2 (R)-4-((S)-1,5-Dimethyl-3-oxo-hexyl)-cyclohex-1-enecarbaldehyde 
• 17904-27-7 (+)-(4R)-[(S)-1,5-dimethyl-3-oxohexyl]cyclohex-1-enecarboxylic acid methyl ester 
• 26091-09-8 (+)-Epitodomatuic acid 
• 26462-75-9 Toluene-4-sulfonic acid (R)-2-((R)-4-methyl-cyclohex-3-enyl)-propyl ester 
• 26575-87-1 (+)-epijuvabione 
• 26462-76-0 (S)-3-((R)-4-methylcyclohex-3-en-1-yl)butanenitrile 
• 26568-68-3 (+)-(2R)-(4-Methyl-3-cyclohexen-(1R)-yl)-6-methylheptan-4-on 
• 24393-74-6 (+)-(4R.8R)-Δ¹-p-Menthen-9-al 
• 5989-27-5 D-limonene 

Relevant academic research and scientific papers

Photocaged Hydrocarbons, Aldehydes, Ketones, Enones, and Carboxylic Acids and Esters that Release by the Norrish II Cleavage Protocol and Beyond: Controlled Photoinduced Fragrance Release

Five families of caged fragrance compounds that allow the storage and release of the following small volatile organic molecules are described: terpene hydrocarbons, aldehydes, ketones, Michael-type α,β-unsaturated enones, and carboxylic acids and esters. These caged molecules are released by photoexcitation via carbonyl-directed hydrogen-transfer processes and subsequent C-C bond cleavage (Norrish Type II) or by didenitrogenation of diazirines.

A chemoenzymatic, preparative synthesis of the isomeric forms of p-menth-1-en-9-ol: Application to the synthesis of the isomeric forms of the cooling agent 1-hydroxy-2,9-cineole

A preparative-scale synthesis of the four p-menth-1-en-9-ol isomers 2a-5a has been achieved by means of two chemoenzymatic processes. Both synthetic pathways start from the enantiomeric forms of limonene that are converted into p-mentha-1,8-dien-9-al isomers 12 and 15. The baker's yeast mediated reduction of the latter aldehydes afforded compounds 3a and 5a, respectively, with very high enantioselectivity. Moreover, chemical reduction of 12 and 15 gives the mixtures of enantiopure diastereoisomers 2a/3a and 4a/5a, respectively. PPL (Porcine pancreas lipase) mediated resolution of the latter mixtures followed by fractionating crystallization of derivatives 2b-5b allowed the enantio- and diastereoisomerically pure alcohols 2a-5a to be obtained. Compounds 2a-5a have then been used as starting materials for the preparation of four isomers of the cooling agent 1-hydroxy-2,9-cineole (6-9). Wiley-VCH Verlag GmbH & Co. KGaA, 2008.

The Synthesis of Two C4 Epimers of 4,8-Dimethyl-2-oxabicyclononan-8-ol (1-Hydroxy-2,9-cineole)

Chemical syntheses of the two 2,9-cineols (10a) and (11a) confirm the view that such compounds may be formed during various 1,8-cineole syntheses.The n.m.r. spectra and conformations of these bicyclic compounds are discussed.