(-)-ALPHA-CEDRENE

Base Information

• Chemical Name: (-)-ALPHA-CEDRENE
• CAS No.: 469-61-4
• Deprecated CAS: 1224161-35-6
• Molecular Formula: C15H24
• Molecular Weight: 204.356
• European Community (EC) Number: 234-257-7,207-418-4
• UNII: 50D4A81G8T
• DSSTox Substance ID: DTXSID0047032
• Nikkaji Number: J5.927G
• Wikipedia: Cedrene
• Wikidata: Q27108601
• Metabolomics Workbench ID: 28416
• Mol file: 469-61-4.mol

Synonyms:1H-3a,7-Methanoazulene,2,3,4,7,8,8a-hexahydro-3,6,8,8-tetramethyl-, [3R-(3a,3ab,7b,8aa)]-; Cedr-8-ene (8CI); a-Cedrene (6CI,7CI); (-)-Cedrene; (-)-a-Cedrene; Levo-a-cedrene; [3R-(3a,3ab,7b,8aa)]-2,3,4,7,8,8a-Hexahydro-3,6,8,8-tetramethyl-1H-3a,7-methanoazulene

Chemical Property of (-)-ALPHA-CEDRENE

Chemical Property:

• Vapor Pressure: 0.0177mmHg at 25°C
• Melting Point: 261-262°C
• Refractive Index: n20/D 1.498
• Boiling Point: 261-262 ºC
• Flash Point: 110.2°C
• PSA: 0.00000
• Density: 0.932
• LogP: 4.41500
• Storage Temp.: 2-8°C
• XLogP3: 4.6
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 0
• Rotatable Bond Count: 0
• Exact Mass: 204.187800766
• Heavy Atom Count: 15
• Complexity: 323

Purity/Quality:

98%,99%, ^*data from raw suppliers

(-)-α-Cedrene(major,contains(+)-β-cedrene) ^*data from reagent suppliers

Safty Information:

• Hazard Codes: Xi,N
• Statements: 36/38-50/53-50
• Safety Statements: 26-60-61-24/25-23

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CC1CCC2C13CC=C(C(C3)C2(C)C)C
• Isomeric SMILES: C[C@@H]1CC[C@@H]2[C@]13CC=C([C@H](C3)C2(C)C)C

Technology Process of (-)-ALPHA-CEDRENE

There total 89 articles about (-)-ALPHA-CEDRENE 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: 96.0%

cedaranyl alcohol → alpha-cedrene (469-61-4)

Guidance literature:

With toluene-4-sulfonic acid; In acetonitrile; at 50 ℃; for 0.5h;

Reference yield: 93.0%

(+)-cedryl acetate (77-54-3) → alpha-cedrene (469-61-4)

Guidance literature:

With tetrafluoroboric acid; In 1,4-dioxane; at 100 ℃; for 1h;

DOI:10.1016/S0040-4020(01)91010-5

Reference yield: 92.0%

cedrenone (1262998-09-3) → alpha-cedrene (469-61-4)

Guidance literature:

cedrenone; With toluene-4-sulfonic acid hydrazide; In ethanol; for 2.5h; Reflux;

With sodium tetrahydroborate; In tetrahydrofuran; water; for 2h; Reflux;

DOI:10.1055/s-0036-1588602

upstream raw materials:

α-cedrol

8,14-cedranoxide

(+)-cedryl acetate

(+)-cedrol

Downstream raw materials:

4-methylisopropylbenzene

(-)-3,8,8-trimethyl-6-methylen-octahydro-3a,7-methano-azulene; (-)-β-cedrene

(3R,3aS,7R,8aS)-3,8,8-trimethyl-2,3,4,7,8,8a-hexahydro-1H-3a,7-cedarane-6-formaldehyde

(8aS)-3c,6,8,8-tetramethyl-(8arH)-1,2,4,7,8,8a-hexahydro-3H-3at,7t-methano-azulenol-(4ξ)

Refernces

• 1、 Schmidt, Thomas. "Olefins by Transition Metal Catalyzed Elimination Reactions from Tertiary Alcohols and Acetates". . p. 8155 - 8160. Retrieved 1991.
• 2、 Hayward,Seymour. "". . p. 572,573. Retrieved 1948.
• 3、 Wood, Devin P.,Guan, Weiyang,Lin, Song. "Titanium and Cobalt Bimetallic Radical Redox Relay for the Isomerization of N -Bz Aziridines to Allylic Amides". supporting information. p. 4213 - 4220. Retrieved 2021/08/10.
• 4、 Zhang, Qi,Tiefenbacher, Konrad. "Sesquiterpene Cyclizations inside the Hexameric Resorcinarene Capsule: Total Synthesis of δ-Selinene and Mechanistic Studies". supporting information. p. 12688 - 12695. Retrieved 2019/08/12.