3-Carene

Base Information

• Chemical Name: 3-Carene
• CAS No.: 13466-78-9
• Molecular Formula: C10H16
• Molecular Weight: 136.237
• Hs Code.: 2902199090
• European Community (EC) Number: 236-719-3
• UN Number: 2319
• DSSTox Substance ID: DTXSID4047462
• Nikkaji Number: J275.524F,J8.118C
• Wikipedia: 3-Carene
• Wikidata: Q19414
• Metabolomics Workbench ID: 140413
• ChEMBL ID: CHEMBL506854
• Mol file: 13466-78-9.mol

Synonyms:(+)-3-carene;3-carene;3-carene, (R)-isomer;3-carene, (S)-(cis)-isomer;delta(3)-carene;delta-3-carene;delta3-carene

Chemical Property of 3-Carene

Chemical Property:

• Vapor Pressure: 1.86mmHg at 25°C
• Melting Point: 25°C
• Refractive Index: n20/D 1.474(lit.)
• Boiling Point: 168-169oC705 mm Hg(lit.)
• Flash Point: 115 °F
• PSA: 0.00000
• Density: 0.857 g/mL at 25oC(lit.)
• LogP: 2.99870
• Storage Temp.: Flammables area
• XLogP3: 2.8
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 0
• Rotatable Bond Count: 0
• Exact Mass: 136.125200510
• Heavy Atom Count: 10
• Complexity: 186
• Transport DOT Label: Flammable Liquid

Purity/Quality:

98% ^*data from raw suppliers

3-Carene ^*data from reagent suppliers

Safty Information:

• Pictogram(s): Xi
• Hazard Codes: Xi,N,Xn
• Statements: 10-43-50/53-65-38-52/53
• Safety Statements: 16-26-36/37-60-61-62-37-24

MSDS Files:

SDS file from LookChem

Total 1 MSDS from other Authors

Useful:

• Chemical Classes: Biological Agents -> Terpenes
• Canonical SMILES: CC1=CCC2C(C1)C2(C)C
• Description: Hydroperoxides of Δ-3-carene are allergens contained in turpentine. Occupational exposure occurs in painters, varnishers, or in ceramic decoration. The percentage of Δ-3-Carene is higher in Indonesian turpentine than in Portugese. (±)-3-Carene is a bicyclic monoterpene found in a variety of plants, including Cannabis. It decreases phagocytosis by rat alveolar macrophages when used at a concentration of 0.5 μM and decreases their viability at a concentration of 5 μM. (±)-3-Carene increases the expression and activity of alkaline phosphatase in mouse osteoblastic MC3T3-E1 subclone 4 cells, indicating induction of osteoblastic differentiation. It also induces calcium formation and increases the expression of osteopontin and type I collagen, which are related to osteoblast mineralization. (±)-3-Carene induces bronchoconstriction in isolated guinea pig lungs when exposed at an air concentration of 3,000 mg/m3.
• Uses: Solvent, intermediate. 3-Carene is a mutagenic compound that may be found in the fumes of heating freshly cut spruce and birch chips. 3-Carene is also found i many esential oils and it inhibits acetylcholinesterase activity.

Technology Process of 3-Carene

There total 11 articles about 3-Carene which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield: 76.5%

(+/-)-10-phenylsulfonylcar-3-ene (116872-39-0) → Δ3-carene (498-15-7,13466-78-9,20296-50-8,116783-27-8,19079-29-9)

Guidance literature:

With ammonia; lithium; In diethyl ether; at -50 ℃; for 1h;

DOI:10.1007/BF01455479

Reference yield: 27.1%

3,7,7-trimethyl-cyclohepta-1,3,5-triene (3479-89-8) → 1,4,4-trimethylcycloheptane (2158-55-6) + 2-carene (554-61-0) + 1,5,5-trimethylcycloheptene (7348-54-1) + 1,4,4-trimethylcycloheptene (4755-36-6) + carane (554-59-6) + 3-carene (13466-78-9,19079-29-9)

Guidance literature:

With hydrogen; platinum; In hexane; at 20 - 22 ℃; Product distribution; various amounts of hydrogen;

DOI:10.1007/BF00575696

Reference yield: 25.0%

2-carene (554-61-0) → 1-methyl-4-isopropyl-1,3-cyclohexadiene (99-86-5) + 4-methylisopropylbenzene (99-87-6) + isoterpinolene (586-63-0) + 3-carene (13466-78-9,19079-29-9)

Guidance literature:

thionin-supported zeolite Na-Y; In hexane; at 20 ℃; for 0.5h; Product distribution;

DOI:10.1002/poc.557

upstream raw materials:

(+/-)-10-phenylsulfonylcar-3-ene

3,7,7-trimethyl-cyclohepta-1,3,5-triene

4-hydroxymethyl-2-carene

α-3,4-Epoxycarane

Downstream raw materials:

C₁₆H₂₀N₂O₄S₃

1-methyl-4-isopropenylbenzene

m-cymene

4-methylisopropylbenzene

Refernces

• 1、 Stratakis, Manolis,Stavroulakis, Manolis,Sofikiti, Nikoletta. "Thermal transformation of monoterpenes within thionin-supported zeolite Na-Y. Acid-catalyzed or electron transfer-induced?". . p. 16 - 20. Retrieved 2003.
• 2、 Manukov, E. N.,Chuiko, V. A.. "HETEROGENEOUS HYDROGENATION OF 3,7,7-TRIMETHYLCYCLOHEPTA-1,3,5-TRIENE". . p. 422 - 425. Retrieved 1983.
• 3、 Wheeler,J.W. et al.. "-". . p. 545 - 549. Retrieved 1969.
• 4、 Veselovskii, V. V.,Makarova, Z. G.,Lutsenko, A. I.,Shpiro, N. A.,Zhulin, V. M.,Moiseenkov, A. M.. "2-PHENYLSULFINYLMETHYL-1,3-BUTADIENE IN THE THERMAL DIELS-ALDER REACTION". . p. 692 - 697. Retrieved 2007/10/02.