4755-33-3

Basic information

• Product Name: (1S)-(-)-CIS-PINAME
• Synonyms: [1S-(1α,2β,5α)]-2,6,6-trimethylbicyclo[3.1.1]heptane;bicyclo[3.1.1]heptane,2,6,6-trimethyl-[1S-(1α,2β,5α)]-;pinane,(1S,2R,5S)-(-)-;PINANE, (1S)-(-)-CIS-;(1S)-(-)-CIS-PINAME;(1S)-(-)-CIS PINANE;[1S-(1alpha,2beta,5alpha)]-2,6,6-trimethylbicyclo[3.1.1]heptane;(1S,2R)-2,6,6-Trimethylbicyclo[3.1.1]heptane
• CAS NO: 4755-33-3
• Molecular Formula: C₁₀H₁₈
• Molecular Weight: 138.25
• EINECS: 225-282-4
• Mol File: 4755-33-3.mol
• Article Data: 52

Chemical Properties

• Boiling Point: 169°C
• Flash Point: 48°C
• Appearance: /
• Density: 0.844g/cm³
• Vapor Pressure: 3.626mmHg at 25°C
• Refractive Index: n20/D 1.463
• CAS DataBase Reference: (1S)-(-)-CIS-PINAME(CAS DataBase Reference)
• NIST Chemistry Reference: (1S)-(-)-CIS-PINAME(4755-33-3)
• EPA Substance Registry System: (1S)-(-)-CIS-PINAME(4755-33-3)

Safety Data

• Statements: 10
• Safety Statements: 16
• RIDADR: UN 2319 3/PG 3
• Hazardous Substances Data: 4755-33-3(Hazardous Substances Data)

Usage

General Description

"(1S)-(-)-CIS-PINAME" is a type of pinene, which is a highly aromatic chemical compound found in the essential oils of various plants, including conifers and herbs. It is classified as a bicyclic monoterpene and is known for its strong pine-like odor. The (1S)-(-)-CIS-PINAME form of pinene has a specific stereochemistry, meaning it has a particular arrangement of atoms in its molecule, resulting in distinct chemical and physical properties. (1S)-(-)-CIS-PINAME is commonly used in the fragrance and flavor industry, as well as in the production of solvents, cleaning products, and other commercial applications. Its natural occurrence and pleasant scent make it a popular ingredient in perfumes, air fresheners, and other scented products.

InChI:InChI=1/C10H18/c1-7-4-5-8-6-9(7)10(8,2)3/h7-9H,4-6H2,1-3H3/t7-,8+,9+/m1/s1

Upstream product

• 18492-59-6 (+)-pinocamphone 
• 473-62-1 (1R,2R,5S)-2,6,6-trimethylbicyclo[3.1.1]heptan-3-one 
• 80-56-8 Pinene 
• 80-56-8 rac-α-pinene 
• 473-55-2 2,6,6-trimethylbicyclo[3.1.1]heptane 
• 7785-26-4 (-)-α-pinene 
• 18172-67-3 beta-pinene 
• 177698-19-0 Beta-pinene 
• 7785-26-4 2,6,6-trimethylbicyclo[3.1.1]hept-2-ene 
• 98-86-2 acetophenone 
• 201230-82-2 carbon monoxide 
• 473-66-5 trans-Verbanon 
• 18172-67-3 (?)-β-pinene 
• 203499-04-1 (-)-(1'S,6'R,3R/S,4R/S)-5-(2',6'-dimethylbicyclo[3.1.1]hept-2'-en-6'-yl)-2-methylpentane-2,3,4-triol 

Downstream Products

• 10281-56-8 (R)-3,7-dimethyl-1,6-octadiene 
• 31485-05-9 (1S)-1r-isopropenyl-2c,3c-dimethyl-cyclopentane 
• 6876-05-7 (1R)-1r-isopropenyl-2c,3t-dimethyl-cyclopentane 
• 99-87-6 4-methylisopropylbenzene 
• 61585-35-1 p-menth-1-ene 
• 110-43-0 n-pentyl methyl ketone 
• 590-67-0 1-Methylcyclohexanol 
• 98-55-5 terpineol 
• 473-54-1 pinan-2α-ol 
• 473-54-1 cis-pinane-2-ol 
• 71697-84-2 (-)-trans-sobrerol 
• 18383-51-2 (-)-trans-carveol 
• 10482-56-1 (-)-(S)-α-terpineol 
• 1028464-68-7 (Z)-verbenol 

Relevant articles and documents

Mild Hydrogenation of α-Pinene Catalyzed by Ru Nanoparticles Loaded on Boron-doped Amphiphilic Core-Shell Mesoporous Molecular Sieves

Highly dispersed and stable catalysts comprising Ru nanoparticles supported on boron-doped amphiphilic core-shell mesoporous molecular sieves (MMS?C@MMS?NH2/B/Ru) with alkyl-modified hydrophobic silica core and NH2-functionalized hydrophilic silica shell are successfully prepared for use in hydrogenation of α-pinene for the first time. Dodecyl-modified MMS?C12@MMS?NH2/B/Ru exhibits the best catalytic activity under mild hydrogenation conditions. The abundant ?NH2 functional groups on the molecular sieve surface and their amphipathy allow the sieves to facilitate attachment of more Ru nanoparticles, and to simplify their dispersion in the water-organic reaction medium. Moreover, B-doped molecular sieves may adjust their acidity to meet the needs of α-pinene hydrogenation. Under mild reaction conditions (25 °C, 1 MPa H2, and 1 h), α-pinene can be completely converted with 99 % selectivity to cis-pinane, because every nanocomposite is equivalent to a microreactor. The catalytic activity does not change much over 5 cycles, indicating that Ru nanoparticles are stably loaded on the molecular sieves.

Highly Selective Hydrogenation of C═C Bonds Catalyzed by a Rhodium Hydride

Under mild conditions (room temperature, 80 psi of H2) Cp*Rh(2-(2-pyridyl)phenyl)H catalyzes the selective hydrogenation of the C═C bond in α,β-unsaturated carbonyl compounds, including natural product precursors with bulky substituents in the β position and substrates possessing an array of additional functional groups. It also catalyzes the hydrogenation of many isolated double bonds. Mechanistic studies reveal that no radical intermediates are involved, and the catalyst appears to be homogeneous, thereby affording important complementarity to existing protocols for similar hydrogenation processes.

Hydrogenation of hydrophobic substrates catalyzed by gold nanoparticles embedded in Tetronic/cyclodextrin-based hydrogels

Hydrogenation of alkenes, alkynes and aldehydes was investigated under biphasic conditions using Au nanoparticles (AuNP) embedded into combinations of α-cyclodextrin (α-CD) and a poloxamine (Tetronic90R4). Thermo-responsive AuNP-containing α-CD/Tetronic90R4 hydrogels are formed under well-defined conditions of concentration. The AuNP displayed an average size of ca. 7 nm and a narrow distribution, as determined by TEM. The AuNP/α-CD/Tetronic90R4 system proved to be stable over time. Upon heating above the gel-to-sol transition temperature, the studied catalytic system allowed hydrogenation of a wide range of substrates such as alkenes, alkynes and aldehydes under biphasic conditions. Upon repeated heating/cooling cycles, the Au NP/α-CD/Tetronic90R4 catalytic system could be recycled several times without a significant decline in catalytic activity.