(2E,6E)-2,6-dimethylocta-2,6-dienedial

Base Information

• Chemical Name: (2E,6E)-2,6-dimethylocta-2,6-dienedial
• CAS No.: 80054-40-6
• Molecular Formula: C10H14O2
• Molecular Weight: 166.22
• DSSTox Substance ID: DTXSID901032253
• Nikkaji Number: J1.586.658F,J1.854.696E
• Wikipedia: 8-Oxogeranial
• Wikidata: Q19598317
• Metabolomics Workbench ID: 63263
• Mol file: 80054-40-6.mol

Synonyms:(2E,6E)-2,6-dimethylocta-2,6-dienedial;8-Oxogeranial;(6E)-8-oxogeranial;80054-40-6;10-oxogeranial;(E,E)-2,6-Dimethyl-2,6-octadienedial;(E,E)-2,6-dimethylocta-2,6-dienedial;trans,trans-2,6-dimethylocta-2,6-dienedial;2,6-Octadienedial, 2,6-dimethyl-, (E,E)-;8-oxocitral;starbld0033087;CHEBI:64239;2,6-Dimethyl-2,6-octadienedial;DTXSID901032253;C17622;Q19598317

Chemical Property of (2E,6E)-2,6-dimethylocta-2,6-dienedial

Chemical Property:

• Boiling Point: 307.7±30.0 °C(Predicted)
• PSA: 34.14000
• Density: 0.949±0.06 g/cm3(Predicted)
• LogP: 2.05700
• Storage Temp.: Hygroscopic, -20°C Freezer, Under inert atmosphere
• Solubility.: Chloroform (Slightly), Ethyl Acetate (Slightly), Methanol (Slightly)
• XLogP3: 1.7
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 2
• Rotatable Bond Count: 5
• Exact Mass: 166.099379685
• Heavy Atom Count: 12
• Complexity: 212

Purity/Quality:

99%, ^*data from raw suppliers

(E,E)-2,6-Dimethyl-2,6-octadienedial ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CC(=CC=O)CCC=C(C)C=O
• Isomeric SMILES: C/C(=C\C=O)/CC/C=C(\C)/C=O
• Uses: (E,E)-2,6-Dimethyl-2,6-octadienedial is a defensive allomone in leaf beetle larvae.

Technology Process of (2E,6E)-2,6-dimethylocta-2,6-dienedial

There total 11 articles about (2E,6E)-2,6-dimethylocta-2,6-dienedial 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: 88.0%

(2E,6E)-8-hydroxy-2,6-dimethylocta-2,6-dienal (38290-51-6) → (2E,6E)-3,7-dimethyl-2,6-octadiene-1,8-dial (80054-40-6)

Guidance literature:

With manganese(IV) oxide; In chloroform; for 48h;

DOI:10.1016/0968-0896(96)00012-0

Reference yield: 70.0%

8-hydroxygeraniol (26488-97-1) → (2E,6E)-3,7-dimethyl-2,6-octadiene-1,8-dial (80054-40-6)

Guidance literature:

With pyridinium chlorochromate; In dichloromethane; for 3h; Ambient temperature;

DOI:10.1016/0040-4020(96)00298-0

Reference yield: 19.0%

3,7-dimethyl-2,6-octadienal (141-27-5,96680-15-8) → (2E,6E)-3,7-dimethyl-2,6-octadiene-1,8-dial (80054-40-6)

Guidance literature:

With selenium(IV) oxide; In dichloromethane; at 20 ℃; for 72h; Inert atmosphere;

DOI:10.1002/anie.201508310

upstream raw materials:

(E/Z)-3,7-dimethyl-2,6-octadienal

<1-(3)H>-10-hydroxygeraniol

2,6-dimethylocta-2E/Z,6E-dienediol

8-hydroxygeraniol

Downstream raw materials:

dl-dehydroiridodial

dl-chrysomelidial

isodehydroiridodiol (3R^*,8R^*)

(+/-)-dehydroiridodiol

Refernces

• 1、 Santangelo,Rotticci,Liblikas,Norin,Unelius. "Resolution of an iridoid synthon, gastrolactol, by means of dynamic acetylation and lipase-catalyzed alcoholysis". . p. 5384 - 5387. Retrieved 2001.
• 2、 Veith,Oldham,Dettner,Pasteels,Boland. "Biosynthesis of defensive allomones in leaf beetle larvae: Stereochemistry of salicylalcohol oxidation in Phratora vitellinae and comparison of enzyme substrate and stereospecificity with alcohol oxidases from several iridoid producing leaf beetles". . p. 429 - 443. Retrieved 2007/10/03.