35736-66-4

Upstream product

• 89-82-7 pulegone 
• 74275-57-3 (R)-3,3,6-Trimethyl-3,5,6,7-tetrahydro-benzo[1,2]dioxol-7a-ol 

Downstream Products

• 35837-04-8 (-)-(1R,3R)-Δ⁴⁽⁵⁾-p-Menthen-3,8-diol (4) 

Relevant academic research and scientific papers

Efficient photooxygenation of olefins by a C60 derivative bearing an organofluorine tail

A C60 derivative bearing an organofluorine tail through the dimethylsilyl moiety (1) was proved to be an efficient photosensitizer in C6F6. Photooxygenation of olefins or dienes was accomplished by catalysis of 1 (0.5 - 1.5 mo1%) at room temperature under an oxygen atmosphere.

Transformation of a monoterpene ketone, (R)-(+)-pulegone, a potent hepatotoxin, in Mucor piriformis

Biotransformation of a monoterpene ketone, (R)-(+)-pulegone (I), a potent hepatotoxin, was studied using a fungal strain, Mucor piriformis. Eight metabolites, namely, 5-hydroxypulegone (II), piperitenone (III), 6- hydroxypulegone (IV), 3-hydroxypulegone (V), 5-methyl-2-(1-hydroxy-1- methylethyl)-2-cyclohexene-1-one (VI), 3-hydroxyisopulegone (VII), 7- hydroxypiperitenone (VIII), and 7-hydroxypulegone (IX), have been isolated from the fermentation medium and identified. GC analysis of the metabolites indicated that II was the major metabolite formed. The organism initiates transformation either by hydroxylation at the C-5 position or by hydroxylation of the ring methylenes, the former being the major activity. On the basis of the identification of the metabolites, pathways for the biotransformation of (R)-(+)-pulegone have been proposed. The mode of transformation of (S)-(-)-pulegone by this organism was shown to be similar to that of its (R)-(+)-enantiomer. When isopulegone (X) was used as the substrate, the organism isomerized it to pulegone (I), which was then transformed to metabolites II-IX.

Biotransformation Products of (5R)-(+)-Pulegone and (2S,5R)-(-)-Menthone Produced by Cultured Cells of Catharanthus roseus

Catharanthus roseus cultured cells produce several new oxidized products from (5R)-(+)-pulegone and (2S, 5R)-(-)-menthone, in some of which a double bond migration has occurred. Products were identified using NMR and mass spectrometry. The pleasant fragrances of some of the products suggest possible use as perfumery agents.

Synthetic Chemistry with Fullerenes. Photooxygenation of Olefins

Under irradiation with visible or UV (>290 nm) light in the presence of molecular oxygen and a minute amount of fullerenes, olefins and dienes undergo ene and Diels-Alder reactions with singlet oxygen to give photooxygenation products.The regio- and stereoselectivities of the photooxygenation of β-myrcene, (+)-pulegone, 4-methylpent-3-en-2-ol, and (+)-limonene were very similar to those observed in known singlet oxygen reactions, indicating that the fullerene-sensitized reaction generates free singlet oxygen.The efficiency of fullerenes and conventional sensitizers was qualitatively examined by using the Diels-Alder reaction between 1O2 and furan-2-carboxylic acid as a probe.Among those examined, C70 was found to be the most effective.The reaction was the fastest and completed with as little as 0.0001 equiv of C70.C60 and hematoporphyrin were found to be of similar efficiency.The methanofullerene 13, which lacks one olefinic conjugation in the C60 core, was as good as C60 itself, but the aminofullerene 14, lacking six double bonds, was quite inferior.The fullerene carboxylic acid 15, which was previously shown to show considerable biochemical activity, was found to be capable of generating singlet oxygen in aqueous DMSO.

Biotransformation of terpenic compounds by fungi. I. Metabolism of R-(+)-pulegone

R-(+)-Pulegone 1 is converted by several fungal strains to new regioselectively hydroxylated compounds. Epoxidation of the double bond does not seem to be responsible for the main observed hydroxylation pattern.