(6E)-8-oxogeraniol

Base Information

• Chemical Name: (6E)-8-oxogeraniol
• CAS No.: 38290-51-6
• Molecular Formula: C10H16O2
• Molecular Weight: 168.236
• DSSTox Substance ID: DTXSID501254819
• Metabolomics Workbench ID: 3526
• Nikkaji Number: J410.203G,J1.521.200D,J2.181.330C
• Wikidata: Q27133145
• Mol file: 38290-51-6.mol

Synonyms:(6E)-8-oxogeraniol;10-oxogeraniol;38290-51-6;(2E,6E)-8-hydroxy-2,6-dimethylocta-2,6-dienal;2,6-Dimethyl-8-hydroxy-2E,6E-octadienal;starbld0001411;(2E,6E)-8-Hydroxy-2,6-dimethyl-2,6-octadienal;SCHEMBL1300611;SCHEMBL1300612;SCHEMBL22134472;CHEBI:64236;DTXSID501254819;LMFA06000130;C20223;(E,E)-8-hydroxy-2,6-dimethylocta-2,6-dienal;trans,trans-8-hydroxy-2,6-dimethylocta-2,6-dienal;Q27133145

Chemical Property of (6E)-8-oxogeraniol

Chemical Property:

• PSA: 37.30000
• LogP: 1.85040
• XLogP3: 1.5
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 2
• Rotatable Bond Count: 5
• Exact Mass: 168.115029749
• Heavy Atom Count: 12
• Complexity: 190

Purity/Quality:

8-Oxogeraniol ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

• Canonical SMILES: CC(=CCO)CCC=C(C)C=O
• Isomeric SMILES: C/C(=C\CO)/CC/C=C(\C)/C=O
• Uses: 8-Oxogeraniol is a derivative of Geraniol (G367000), which is used in the synthesis of insect repellant. It is also used in the synthesis of Angelicoin A and Herecinone J, which inhibit collagen-induced platelet aggregation.

Technology Process of (6E)-8-oxogeraniol

There total 9 articles about (6E)-8-oxogeraniol 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: 100.0%

(2E,6E)-3,7-dimethyl-8-oxoocta-2,6-dien-1-yl acetate (37905-02-5) → (2E,6E)-8-hydroxy-2,6-dimethylocta-2,6-dienal (38290-51-6)

Guidance literature:

With potassium hydroxide; water; In ethanol; at -10 ℃; for 1h;

DOI:10.1021/ja0119144

Reference yield: 49.0%

(2E/Z,6E)-3,7-dimethyl-2,6-octadiene-1,8-dial (156155-54-3) → 2,6-dimethylocta-2E/Z,6E-dienediol (156155-53-2) + hydroxy-8 dimethyl-2,6 octadiene-2 (E), 6 al-1 (38290-51-6,77878-85-4,80054-42-8,88524-78-1,88524-79-2)

Guidance literature:

With potassium borohydride; Amberlit IR C-50; lithium chloride; In 1,4-dioxane; isopropyl alcohol; at 20 ℃; for 10h;

Reference yield: 12.4%

Geraniol (106-24-1) → (2E,6E)-8-hydroxy-2,6-dimethylocta-2,6-dienal (38290-51-6)

Guidance literature:

With selenium(IV) oxide; In 1,4-dioxane; ethanol; at 80 ℃; for 5h; Inert atmosphere;

DOI:10.1021/acs.jafc.6b04534

upstream raw materials:

(2E,6E)-3,7-dimethyl-8-oxoocta-2,6-dien-1-yl acetate

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

Geraniol

3,7-dimethyl-2E,6-octadien-1-yl acetate

Downstream raw materials:

(E)-3,7-dimethyl-oct-2-ene-1,8-diol

(2E)-8-aniline-3,7-dimethyl-2,6-octadien-1-ol

Refernces

• 1、 -. "ISOPRENE OLIGOMER, POLYISOPRENE, PROCESSES FOR PRODUCING THESE MATERIALS, RUBBER COMPOSITION, AND PNEUMATIC TIRE". Paragraph 197-198. . Retrieved 2014/06/25.
• 2、 Labadie, Guillermo R.,Viswanathan, Rajesh,Poulter, C. Dale. "Farnesyl diphosphate analogues with ω-bioorthogonal azide and alkyne functional groups for protein farnesyl transferase-catalyzed ligation reactions". . p. 9291 - 9297. Retrieved 2008/03/14.