2-methylisoborneol and isoborneol

Spontaneous oxidized flavor (SOF) has been reported over the past 5 decades as a sporadic objectionable flavor problem in bovine milk. Parameters previously reported to influence SOF development in milk have been contradictory, limiting the ability to monitor and develop mitigation strategies. The current paper investigates the causative compounds associated with milk identified as SOF milk in the Midwest dairy region of the United States. Based on GC/MS-olfactometry analysis, endo-borneol, 2-methylisoborneol, and α-terpineol were identified as the off-flavor compounds. Sensory recombination studies further confirmed the sensory contribution of these compounds to the noted off-flavor attributes in the original milk, which were described as "green," "musty," and "unclean." These compounds are known microbial-derived flavor taints, indicating oxidation was not the origin of the objectionable flavor in the milk. This noted misclassification of the milk as SOF indicates the challenge of defining flavor defects without the identification of the active compounds.

Topics: Animals; Camphanes; Cattle; Color; Cyclohexane Monoterpenes; Cyclohexenes; Female; Gas Chromatography-Mass Spectrometry; Milk; Monoterpenes; Olfactometry; Oxidation-Reduction; Taste

TRPA1, one of the transient receptor potential channels, has been reported to be involved in nociception and inflammatory pain, suggesting that this molecule could be a promising target for the development of analgesic agents. We screened several monoterpene analogs of camphor, which is known to inhibit human (h) TRPA1, to identify more effective naturally occurring TRPA1 antagonists. Borneol, 2-methylisoborneol, and fenchyl alcohol exhibited higher inhibitory effects on hTRPA1 activity than either camphor or 1,8-cineole. Our results revealed further that the S873, T874, and Y812 residues of hTRPA1 were involved in the inhibitory effects, suggesting that the hydroxyl group in the six-membered ring of the inhibitors may be interacting with these amino acids. Further research on these identified TRPA1 antagonists could lead to new pain therapeutics.

Topics: Analgesics; Calcium Channels; Camphanes; Camphor; Cells, Cultured; Cyclohexanols; Dose-Response Relationship, Drug; Eucalyptol; HEK293 Cells; Humans; Hydroxides; Monoterpenes; Nerve Tissue Proteins; Norbornanes; Pain; Transient Receptor Potential Channels; TRPA1 Cation Channel

The production of 2-methylisoborneol (MIB) by certain fungi and algae can contribute musty off-flavors to foods and water supplies if uncontrolled. The goal of this research was to develop a nonsensory simple method for the detection of MIB. Anti-MIB monoclonal antibodies were produced by immunizing mice with borneol-conjugated protein and selecting positive clones with an MIB-protein conjugate. An indirect competitive immunoassay developed using this antibody had a detection limit of 0.6 microg L(-)(1) and an I(50) value of 5 microg L(-)(1). Detection was relatively specific for MIB and showed 20% cross-reactivity with borneol or isoborneol and 4-5% cross-reactivity with camphor. No cross-reactivity to geosmin was observed.

Topics: Animals; Antibodies, Monoclonal; Camphanes; Enzyme-Linked Immunosorbent Assay; Female; Hybridomas; Immunization; Mice; Mice, Inbred BALB C; Sensitivity and Specificity