140860-25-9

Upstream product

• 19246-50-5 9-hydroxycarbotanacetone 
• 5989-27-5 D-limonene 
• 6485-40-1 (R)-Carvone 
• 116499-64-0 (R)-dihydrocarvone 
• 38050-36-1 (1R,8Ξ)-2c,9-methoxyboranediyl-(1rH,4tH)-p-menthane 

Downstream Products

• 38339-60-5 2-((1R,4R)-4-Methyl-3-oxo-cyclohexyl)-propionic acid 
• 140924-70-5 (R)-2-((1R,4R)-4-Methyl-3-oxo-cyclohexyl)-propionaldehyde 
• 140860-27-1 Acetic acid 2-((1R,4R)-4-methyl-3-oxo-cyclohexyl)-propyl ester 
• 140860-29-3 (R)-3,3,3-Trifluoro-2-methoxy-2-phenyl-propionic acid 2-((1R,3S,4R)-3-hydroxy-4-methyl-cyclohexyl)-propyl ester 
• 140860-30-6 (R)-3,3,3-Trifluoro-2-methoxy-2-phenyl-propionic acid 2-((1R,4R)-4-methyl-3-oxo-cyclohexyl)-propyl ester 
• 140860-28-2 (R)-3,3,3-Trifluoro-2-methoxy-2-phenyl-propionic acid 2-((1R,3S,4R)-3-acetoxy-4-methyl-cyclohexyl)-propyl ester 
• 140860-23-7 (1S,2R,5R)-5-((R)-2-Hydroxy-1-methyl-ethyl)-2-methyl-cyclohexanol 
• 140860-17-9 Acetic acid 2-((1R,3S,4R)-3-hydroxy-4-methyl-cyclohexyl)-propyl ester 
• 57685-13-9 9-hydroxycarbotanacetone diacetate 
• 65648-48-8 (2R,5R)-2-Methyl-5-vinyl-cyclohexanone 

Relevant academic research and scientific papers

New renewably-sourced polyesters from limonene-derived monomers

The functionalisation of limonene has enabled the synthesis of two renewably-sourced monomers for the formation of terpene-derived polyesters. Three methods for the synthesis of the novel hydroxy-acid 6 are reported and their green-credentials scrutinised through comparison of their sustainability-metrics. Step-growth homo-polymerisation of 6 is demonstrated to yield a low molecular weight (2.6 kDa) novel polyester with 100% of its carbon content originating from the terpene starting material. The corresponding diol 2 is shown to act as a co-monomer with a renewable diacid. The resultant polyesters display impressive Mns of up to 30 kDa with Tgs between -6 and 24 °C. These materials have been shown to depolymerise under basic conditions for reclamation of the diol monomer 2.

BIOTRANSFORMATION OF MONOTERPENOIDS, (-)- AND (+)-MENTHOLS, TERPINOLENE AND CARBOTANACETONE BY ASPERGILLUS SPECIES

Four monoterpenoids, (-)- and (+)-menthols, terpinolene and carvotanacetone were biotransformed by Aspergillus niger and several related species.Aspergillus niger converted (-)-menthol to 1-, 2-, 6-, 7-, and 9-hydroxymenthols and the mosquito repellent-active 8-hydroxymenthol.On the other hand, (+)-menthol was smoothly biotransformed by A. niger to give 7-hydroxymenthol.Aspergillus cellulosae biotransformed (-)-menthol specifically to 4-hydroxymenthol.Terpinolene and (-)-carvotanacetone were converted by A. niger to two α,β-unsaturated ketones, a fenchane-type compound and diastereoisomeric p-menthane-2,9-diols and 8-hydroxycarvomenthol, respectively.Key Word Index: Aspergillus awamori; A. cellulosae; A. fumigatus; A. niger; A. sojae; A. terreus; A. usami; Aspergillaceae; biotransformation; (-)- and (+)-menthols; terpinolene; (-)-carvotanacetone; mosquito repellent.

Stoichiometric Hydroboration-Oxidation Reaction of Monocyclic Monoterpenoids: A Mechanistic Approach

The stoichiometric studies on hydroboration-oxidation reactions of (-)-carvone have been carried out to gain an insight into the mechanism of formation of unusual products 2-oxo-p-menth-9-ols (IVb,c), p-menth-2,9-diols (Xa,b) and p-menth-1-en-9-ol (VII).Based on high resolution PMR spectral data, the stereochemistry of IVb,c and Xa,b has been deduced.Similiar studies have been extended to (+)-dihydrocarvone and (-)-carveol.