(+)-Aristolochene

Base Information

• Chemical Name: (+)-Aristolochene
• CAS No.: 123408-96-8
• Molecular Formula: C15H24
• Molecular Weight: 204.356
• UNII: 459BG6ZY5H
• DSSTox Substance ID: DTXSID90349637
• Nikkaji Number: J790.281F
• Wikipedia: Aristolochene
• Wikidata: Q3622703
• Metabolomics Workbench ID: 28303
• Mol file: 123408-96-8.mol

Synonyms:(+)-Aristolochene;123408-96-8;Aristolochene, (+)-;(1S,7S,8aR)-aristolochene;459BG6ZY5H;UNII-459BG6ZY5H;(1S,7S,8aR)-1,2,3,4,6,7,8,8a-Octahydro-1,8a-dimethyl-7-(1-methylethenyl)naphthalene;(4S,4aR,6S)-4,4a-dimethyl-6-prop-1-en-2-yl-2,3,4,5,6,7-hexahydro-1H-naphthalene;Naphthalene, 1,2,3,4,6,7,8,8a-octahydro-1,8a-dimethyl-7-(1-methylethenyl)-, (1S,7S,8aR)-;(4S,4aR,6S)-4,4a-dimethyl-6-(prop-1-en-2-yl)-1,2,3,4,4a,5,6,7-octahydronaphthalene 7betaH-eremophila-9,11-diene;Naphthalene, 1,2,3,4,6,7,8,8a-octahydro-1,8a-dimethyl-7-(1-methylethenyl)-, (1S-(1alpha,7beta,8aalpha))-;4,5-di-epi-Aristoloshene;7betaH-eremophila-9,11-diene;CHEBI:43445;DTXSID90349637;LMPR0103270003;C02004;Q3622703;(4S,4aR,6S)-4,4a-dimethyl-6-(prop-1-en-2-yl)-1,2,3,4,4a,5,6,7-octahydronaphthalene;NAPHTHALENE, 1,2,3,4,6,7,8,8A-OCTAHYDRO-1,8A-DIMETHYL-7-(1-METHYLETHENYL)-, (1S-(1.ALPHA.,7.BETA.,8A.ALPHA.))-

Chemical Property of (+)-Aristolochene

Chemical Property:

• Vapor Pressure: 0.009mmHg at 25°C
• Boiling Point: 274.248°C at 760 mmHg
• Flash Point: 107.811°C
• Density: 0.894g/cm³
• XLogP3: 5.2
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 0
• Rotatable Bond Count: 1
• Exact Mass: 204.187800766
• Heavy Atom Count: 15
• Complexity: 297

Purity/Quality:

99%, ^*data from raw suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CC1CCCC2=CCC(CC12C)C(=C)C
• Isomeric SMILES: C[C@H]1CCCC2=CC[C@@H](C[C@]12C)C(=C)C

Technology Process of (+)-Aristolochene

There total 17 articles about (+)-Aristolochene 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: 94.0%

farnesyl pyrophosphate (372-97-4,13058-04-3,25744-33-6,27248-37-9,27248-38-0,40716-68-5) → 4,5-di-epi-aristolochene (123408-96-8)

Guidance literature:

With aristolochene synthase from Penicillium roqueforti; In pentane; at 28 ℃; pH=7.5; Temperature; stereoselective reaction; Flow reactor; Enzymatic reaction;

DOI:10.1002/ange.202005183

Reference yield: 73.0%

farnesyl pyrophosphate ammonium salt → 4,5-di-epi-aristolochene (123408-96-8)

Guidance literature:

With aristolochene synthase; for 0.75h; Enzymatic reaction;

DOI:10.1002/ejoc.201601388

Reference yield:

farnesyl pyrophosphate (372-97-4,13058-04-3,25744-33-6,27248-37-9,27248-38-0,40716-68-5) → (S)-(-)-germacrene A (28028-64-0,28387-44-2,69460-21-5,69460-22-6,69609-31-0,69609-33-2,69686-13-1,69686-14-2,75023-40-4,83509-17-5) + 4,5-di-epi-aristolochene (123408-96-8) + (-)-valencene (724783-68-0)

Guidance literature:

With aristolochene synthase from Penicillium roqueforti; magnesium chloride; In various solvent(s); at 30 ℃; for 0.166667h; pH=7.5; Further Variations:; var. reagents; Enzyme kinetics; Product distribution;

DOI:10.1021/ja0499593

upstream raw materials:

farnesyl pyrophosphate

farnesol

1-chloro-3,7,11-trimethyldodeca-2,6,10-triene

Refernces

• 1、 Tang, Xiaoping,Allemann, Rudolf K.,Wirth, Thomas. "Optimising Terpene Synthesis with Flow Biocatalysis". . p. 414 - 418. Retrieved 2017.
• 2、 Faraldos, Juan A.,Gonzalez, Veronica,Senske, Michael,Allemann, Rudolf K.. "Templating effects in aristolochene synthase catalysis: Elimination versus cyclisation". supporting information; experimental part. p. 6920 - 6923. Retrieved 2011/11/04.