10136-65-9

Usage

Uses

Used in Cosmetics and Perfumery Industry:
Isobornyl ketone is used as a fragrance ingredient and flavoring agent for its pleasant scent and taste, enhancing the sensory experience of cosmetics and perfumes.
Used in Food Products Industry:
In the food industry, isobornyl ketone serves as a flavoring agent, adding a desirable taste to various food products while maintaining the quality and stability of the products over time.
Used as a Chemical Intermediate:
Isobornyl ketone is utilized as a chemical intermediate in the synthesis of other compounds, contributing to the production of a range of chemical products.

InChI:InChI=1/C10H16O2/c1-9(2)6-4-7(9)10(3,12)8(11)5-6/h6-7,12H,4-5H2,1-3H3

Upstream product

• 473-62-1 (1S,5R)-2,6,6-Trimethyl-bicyclo[3.1.1]heptan-3-one 
• 14575-93-0 isopinocamphone 
• 7785-70-8 (+)-α-pinene 
• 7785-26-4 (-)-α-pinene 
• 80-56-8 Pinene 
• 276253-82-8 tert-butyl 2-[(E)-((1R,2R,5R)-2-hydroxy-2,6,6-trimethylbicyclo-[3.1.1]heptan-3-ylidene)amino]acetate 
• 126003-99-4 (1R,2R,5R)-3-[(E)-(S)-1,2-Diphenyl-ethylimino]-2,6,6-trimethyl-bicyclo[3.1.1]heptan-2-ol 
• 126003-97-2 (1R,2R,5R)-3-(benzylimino)-2,6,6-trimethylbicyclo[3.1.1]heptan-2-ol 
• 22422-34-0 (1R,2R,3S,5R)-2,3-pinane diol 
• 329710-76-1 2-(trifluoromethoxy)ethyl trifluoromethanesulphonate 
• 138175-23-2 (1R,2R,5R)-2,6,6-Trimethyl-3-[(E)-pyridin-2-ylmethylimino]-bicyclo[3.1.1]heptan-2-ol 
• 80-56-8 rac-α-pinene 
• 53404-49-2 2,3-trans-pinanediol 

Downstream Products

• 918625-33-9 2,6,6-Trimethyl-3-(pyridin-3-ylmethylimino)bicyclo[3.1.1]heptan-2-ol 
• 125423-98-5 [(1R,2R,5R)-2-Hydroxy-2,6,6-trimethyl-bicyclo[3.1.1]hept-(3E)-ylideneamino]-acetic acid (1S,2R,5S)-2-isopropyl-5-methyl-cyclohexyl ester 
• 125423-98-5 [(1R,2R,5R)-2-Hydroxy-2,6,6-trimethyl-bicyclo[3.1.1]hept-(3E)-ylideneamino]-acetic acid (1R,2S,5R)-2-isopropyl-5-methyl-cyclohexyl ester 
• 22422-34-0 (1R,2R,3S,5R)-2,3-pinane diol 
• 328000-60-8 (1R,2R,5R)-3-(4,5-Diphenyl-1,3-oxazol-2-ylmethylimino)-2,6,6-trimethylbicyclo[3.1.1]heptan-2-ol 
• 126003-99-4 (1R,2R,5R)-3-[(E)-(S)-1,2-Diphenyl-ethylimino]-2,6,6-trimethyl-bicyclo[3.1.1]heptan-2-ol 
• 1027313-50-3 (1R,2R,5R)-3-[(E)-(R)-1-Furan-2-yl-2-(4-methoxy-phenyl)-ethylimino]-2,6,6-trimethyl-bicyclo[3.1.1]heptan-2-ol 
• 90473-01-1 (1R,2R,5R)-ethyl-((2-hydroxypinan-3-ylene)amino)acetate 

Relevant academic research and scientific papers

ASYMMETRIC SYNTHESIS OF (+)-PHOSPHINOTHRICIN and (+)-2-AMINO-4-PHOSPHONOBUTYRIC ACID

Asymmetric synthesis of (+)-phosphinothricin, (+)-2-amino-4-phosphono-butyric acid, and their enantiomers has been achieved by the Michael addition of chiral glycine Schiff bases to vinyl phosphorus compounds.

Synthesis and physical chemical properties of 2-amino-4-(trifluoromethoxy)butanoic acid-a CF3O-containing analogue of natural lipophilic amino acids

2-Amino-2-(trifluoromethoxy)butanoic acid (O-trifluoromethyl homoserine) was synthesized as a racemate and in both enantiomeric forms. The measured pKa and log D values establish the compound as a promising analogue of natural aliphatic amino acids.

Chiral Titanium(IV) Complexes Containing Polydentate Ligands Based on α-Pinene. Catalytic Activity in Sulfoxidation with Hydrogen Peroxide

The reaction of TiCl4-n(OiPr)n (n = 0, 2, 4) with various terpenoid preligands based on α-pinene, C7H6Me3(OH)(NCH2CH2G) (G = NH2, I; NHMe, II; OH, III), stereoselectively affords a series of new chiral titanium(IV) complexes. Such complexes are either octahedral, [TiCl2X(OC7H6Me3NCH2CH2G-κ3N,N,O)] (X = Cl, G = NH2, 1; X = OiPr, G = NH2, 2; G = NHMe, 3), or trigonal bipyramidal, [Ti(OiPr)3(OC7H6Me3NCH2CH2G-κ2N,O)] (G = NH2, 4; NHMe, 5) and [TiX(OiPr)(OC7H6Me3NCH2CH2O-κ3N,O,O?)] (X = Cl, 6; OiPr, 8), depending on the acidity of titanium, the reaction conditions and the nature of the pendant ending group of the terpenoid ligand. Density functional theory (DFT) calculations have been carried out to assess the stability of the multiple possible diastereoisomers allowing us to propose structural suggestions. The new titanium complexes efficiently catalyze the selective oxidation of various types of sulfides to either sulfoxides or sulfones using aqueous hydrogen peroxide, under mild conditions. All compounds have been characterized by multinuclear NMR spectroscopy and the molecular structure for some of them has been determined by X-ray diffraction.

Novel access to verbenone via ruthenium nanoparticles-catalyzed oxidation of Α-pinene in neat water

Aqueous suspensions of Ru(0) nanoparticles, stabilized with hydroxyethylammonium salts and possessing sizes around 2 nm, proved to be active and selective in the mild oxidation of α-pinene in the presence of tert-butylhydroperoxide, in neat water. Verbenone, a product of great interest for fine chemistry, was obtained as major product with yield up to 41% under optimized conditions. 2-hydroxy-3-pinanone was identified as a co-product of the reaction, but with very low amount (7%). Kinetic investigations allowed determining the potential reaction intermediates and by-products. Moreover, mechanistic studies with radical scavengers confirmed that α-pinene oxidation mainly implies both carbon- and oxygen-centered radicals.

Synthesis of chiral 1,2-diamines from α-pinene and their use in asymmetric nitroaldol reaction

Abstract Chiral diamines with C 1 and C 2 symmetry have been synthesized from 2-hydroxypinan-3-one and tested as ligands in Cu-catalyzed asymmetric nitroaldol reaction of nitromethane with 4-nitrobenzaldehyde.

A practical method for preparation of optically pure oxazaborolidines from α-pinene

(1S,2S,3R,5S)- and (1S,2S,3R,5S)-3-amino-2-hydroxypinane (1 and 2) were prepared from the corresponding α-pinene in optically pure form. They and their derivatives reacted with various organoborane compounds. A variety of chiral oxazaborolidines 3a-e and 4 were obtained in high yield.

New chiral ligands derived from (+) and (-)-α-pinene for the enantioselective addition of diethylzinc to aldehydes

In this study, we synthesized five new chiral ligands from (+) and (-)-α-pinene, which were successfully employed in the stereoselective addition of diethylzinc to aldehydes, leading to secondary chiral alcohols in up to 99% yield and 94% e.e.

Evidence for the existence of a cyclic ruthenium (VI) diester as an intermediate in the oxidative scission of (-)-α-pinene with RuO4

The reaction of (-)-α-pinene (1) with RuO4 in CCl4 at room temperature affords the ketoaldehyde 3 as the sole product. Evidence is reported that the oxidative scission of the olefinic substrate to 3 proceeds through a ruthenium (VI) diester intermediate for which we propose structure 2 on the basis of spectral evidence and comparison with the osmium-containing analogue of 2, synthesised by reaction of (-)-α-pinene with OsO4 in dioxane and whose structure has been determinated by single crystal X-ray diffraction analysis. Compound 2 was also shown to be an intermediate compound in the RuO4 oxidation of (-)-α-pinene performed in acetone-water (2:1) which gives α-ketol 4 as the sole oxidation product.

Metabolism and mode of action of cis- and trans-3-pinanones (the active ingredients of hyssop oil)

1. Hyssop oil is an important food additive and herbal medicine and the principal active ingredients are (-)-cis- and (-)-trans-3-pinanones. No information is available on their metabolism or specific mode of action. 2. The metabolites of cis- and trans-3-pinanones were examined from mouse and human liver microsomes and human recombinant P4503A4 with NADPH and on administration to mouse by gas chromatography/chemical ionization mass spectrometry comparison with standards from synthesis. 3. The major metabolite of cis-3-pinanone in each P450 system and in brain of the i.p.-treated mouse in quantitative studies was 2-hydroxy-cis-3-pinanone, and two minor metabolites were hydroxypinanones other than 2-hydroxy-trans-3-pinanone and 4S-hydroxy-cfs-3-pinanone. The urine from oral cis-3-pinanone treatment examined on a qualitative basis contained conjugates of metabolites observed in the microsomal systems plus 2,10-dehydro-3-pinanone. 4. Trans-3-pinanone was metabolized more slowly than the cis-isomer in each system to give hydroxy derivatives different than those derived from cis-3-pinanone. 5. Cis- and trans-3-pinanones and hyssop oil act as γ-aminobutyric acid type A (GABAA) receptor antagonists based on inhibition of 4′-ethynyl-4-n-[2,3-3H2] propylbicycloorthobenzoate ([3H]EBOB) binding in mouse brain membranes (IC50 of 35-64μM) and supported by tonic/clonic convulsions in mouse (i.p. LD50 175 to >250 mg kg-1) alleviated by diazepam. The cis-3-pinanone metabolites 2-hydroxy-cis-3-pinanone and 2,10-dehydro-3-pinanone exhibit reduced toxicity and potency for inhibition of [3H]EBOB binding.

Synthesis and characterization of new palladium complexes based on polydentate chiral Schiff base and amines ligands derived from (+)-2-hydroxypinan-3-one

Seven novel palladium complexes of the type [Pd(HL)Cl2] and [Pd(L)Cl] containing chiral pinane ligands (HL = 3-[(2-aminoethyl)imino]-pinane-2-ol; 3,3′-(ethylenediimino)bis-pinane-2-ol; cis-3-(2-aminoethylamino)-pinane-2-ol; cis-3,3′(ethylenediamino)bis-pinane-2-ol; trans-3,3′(ethylenediamino)bis-pinane-2-ol; 3-[2-(2-hydroxybenzylamino)ethylamino]-pinane-2-ol; L = 3-[2-(3,5-di-tert-butyl-2-hydroxybenzylidene)aminoethylimino]pinane-2-ol) were synthesized in good yields from the direct reaction of chiral nitrogen ligands with Li2PdCl4 in MeOH. These synthesized complexes were characterized by means of elemental analysis, FT-IR, multidimensional and multinuclear NMR spectroscopic methods.