4176-04-9

Basic information

• Product Name: (1R,4S,6S)-4,7,7-trimethylnorcaran-3-one
• Synonyms: (-)-trans-Caranon-(4);(-)(1R:4S:6S)-trans-Caran-3-on;(-)-trans-Caran-4-one;trans-4-caranone;(-)-trans-Caran-4-on;(-)-trans-caranone-(4)
• CAS NO: 4176-04-9
• Molecular Formula: C₁₀H₁₆O
• Molecular Weight: 152.236
• Mol File: 4176-04-9.mol
• Article Data: 10

Chemical Properties

• Boiling Point: 208.5°Cat760mmHg
• Flash Point: 72.8°C
• Density: 0.95g/cm³
• CAS DataBase Reference: (1R,4S,6S)-4,7,7-trimethylnorcaran-3-one(CAS DataBase Reference)
• NIST Chemistry Reference: (1R,4S,6S)-4,7,7-trimethylnorcaran-3-one(4176-04-9)
• EPA Substance Registry System: (1R,4S,6S)-4,7,7-trimethylnorcaran-3-one(4176-04-9)

Safety Data

• Hazardous Substances Data: 4176-04-9(Hazardous Substances Data)

Usage

Description

(1R,4S,6S)-4,7,7-trimethylnorcaran-3-one, a colorless liquid with a floral, woody odor, is a chemical compound with the molecular formula C10H18O. It is classified as a ketone and is commonly used in various industries due to its versatile nature and desirable properties.

Uses

Used in Fragrance and Flavoring Industry:
(1R,4S,6S)-4,7,7-trimethylnorcaran-3-one is used as a fragrance and flavoring agent for its pleasant scent, enhancing the aroma and taste of various products.
Used in Cosmetics and Toiletries Industry:
(1R,4S,6S)-4,7,7-trimethylnorcaran-3-one is used as an ingredient in cosmetics and toiletries, contributing to their pleasant scent and improving the overall sensory experience for consumers.
Used in Household Products Industry:
(1R,4S,6S)-4,7,7-trimethylnorcaran-3-one is used in the manufacturing of household products, such as cleaning agents and air fresheners, to provide a fresh and appealing scent.
Used as a Flavor Modifier:
(1R,4S,6S)-4,7,7-trimethylnorcaran-3-one is used as a flavor modifier in the food industry, enhancing the taste of certain food products and improving their overall flavor profile.

Upstream product

• 64-17-5 ethanol 
• 10395-49-0 (1S,4R,6R)-4-Methoxy-4,7,7-trimethyl-bicyclo[4.1.0]heptan-3-one 
• 13466-78-9 3-carene 
• 4017-88-3 cis-carane-4-ol 
• 4017-88-3 (+/-)-cis-caran-trans-4-ol 
• 936-91-4 3-carene epoxide 
• 498-15-7 (+)-Δ³-carene 
• 4089-03-6 (1S,3S,4S)-caran-4-ol 
• 4017-89-4 (1S,3S,4R)-caran-4-ol 
• 936-92-5 (1S,3R,4S,6R)-3,4-epoxy-3,7,7-trimethylbicyclo[4.1.0]heptane 
• 1779-49-3 Methyltriphenylphosphonium bromide 
• 4176-01-6 cis-carane-4-one 
• 936-91-4 α-3,4-Epoxycarane 
• 4017-83-8 (-)-(1R,3R,6S)-4-methylene-7,7-dimethylbicyclo[4.1.0]heptan-3-ol 

Downstream Products

• 23733-65-5 (S)-3-isopropyl-6-methylcyclohex-2-enone 
• 4176-01-6 trans-4-caranone 
• 130467-35-5 (+)-trans-caran-cis-4-methanol 
• 99341-58-9 (-)-cis-caran-trans-4-methanol 
• 131566-05-7 cis-caran-cis-4-methanol 
• 4175-95-5 (-)-4-Caranon-semicarbazon 
• 4176-01-6 (-)-isocaranone 

Relevant articles and documents

Molecular rearrangements of α-(trans)- and β-(cis)-3,4-epoxycaranes in acid media

Configuration of the oxirane ring in stereoisomeric 3,4-epoxycaranes affects the direction of their skeletal rearrangements in liquid (HSO3F-SO2FCl) and over solid (TiO2/SO42-) superacids; in the latter case, compounds postulated as intermediates in the liquid-phase process have been isolated.

Catalytic transformations of 3-carene oxide over alumina-rare earth oxide catalysts

Isomerization of 3-carene oxide over binary oxide catalysts like Al2O3-Y2O3, Al2O3-Sm2O3, Al2O3-Eu2O3, Al2O3-Pr6O11 and Al2O3-Nd2O3 at 80 deg C and 110 deg C has been studied. 3,6,6-Trimethylbicyclohexane-3-carboxaldehyde and caranone are the major products formed at 80 deg C.Rise in reaction temperature results in an increase in epoxide transformation and an irregular variation in the yield of products.

Oxygen-containing Bicyclic Monoterpenes. 1H, 13C and 17O NMR Spectroscopic and X-Ray Diffraction Studies of Seven Oxidation Products of (+)-3-Carene

Seven oxidation products of (1S,6R)-(+)-3,7,7-trimethylbicyclohept-3-ene 1; (1S,6R)-3,7,7-trimethylbicyclohept-3-en-2-one (3-caren-2-one) 2, (1S,6R)-3,7,7-trimethylbicyclohept-3-en-5-one (3-caren-5-one) 3, (1S,6R)-3,7,7-trimethylbicyclohept-3-ene-2,5-dione (3-carene-2,5-dione) 4, (1S,3S,4R,6R)-(+)-3,7,7-trimethylbicycloheptene 3,4-trans-oxide (trans-3,4-epoxy-3-carene) 5, (1S,3R,4R,6R)-3,7,7-trimethylbicycloheptane-3-exo-4-endo-diol (carane-3-exo-4-endo-diol) 6 and (1S,2R,4R,5R)-1-methyl-4-exo-(1-hydroxy-1-methylethyl)bicyclohexan-2-endo-ol 7 and (1S,6R)-3-endo-7,7-trimethylbicycloheptan-4-one (trans-4-caranone) 8 have been obtained by oxidation with tert-butylchromate, selenium dioxide, hydrogen peroxide and peracetic acid.The 1H, 13C and 17O NMR spectra of the purified oxidation products have been recorded and assigned.In addition to C,H-COSY spectra, the 1J(C,H) coupling constants were especially useful in 13C NMR spectral assignment.The differentiation between isomeric ketones 2 and 3 is based on a clear difference in the 13C NMR shifts of the double bond methyl.The stereochemical structure elucidation of oxide 5 is based on lanthanide shift reagent induced effects.For ketone 8, molecular mechanics (MM) calculations and comparison of experimental and theoretical 3J(H,H) coupling constants are needed for a final structure elucidation.The assignment of 17O NMR lines of diols 6 and 7 is based on literature values.The crystal structures and absolute configurations of pure enantiomers of diols 6 and 7 have been determined by X-ray diffraction.Crystal data: a = 7.659(2), b = 10.804(3), c = 25.509(4) Angstroem, orthorhombic, space group C2221, Z = 8 (6) and a = 8.076(4), b = 8.836(2), c = 12.487(3) Angstroem, orthorhombic, space group P212121, Z = 4 (7).