(6E)-8-hydroxygeranial

Base Information

• Chemical Name: (6E)-8-hydroxygeranial
• CAS No.: 80054-37-1
• Molecular Formula: C₁₀H₁₆O₂
• Molecular Weight: 168.236
• DSSTox Substance ID: DTXSID001240742
• Metabolomics Workbench ID: 63262
• Nikkaji Number: J410.204E,J1.521.199G
• Wikidata: Q27133146
• Mol file: 80054-37-1.mol

Synonyms:(6E)-8-hydroxygeranial;(2E,6E)-8-hydroxy-3,7-dimethylocta-2,6-dienal;(E,E)-8-hydroxy-3,7-dimethylocta-2,6-dienal;trans,trans-8-hydroxy-3,7-dimethylocta-2,6-dienal;10-hydroxygeranial;SCHEMBL16946291;CHEBI:64238;DTXSID001240742;80054-37-1;C20222;2,6-Octadienal, 8-hydroxy-3,7-dimethyl-, (E,E)-;Q27133146

Chemical Property of (6E)-8-hydroxygeranial

Chemical Property:

• XLogP3: 1.8
• 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:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

• Canonical SMILES: CC(=CC=O)CCC=C(C)CO
• Isomeric SMILES: C/C(=C\C=O)/CC/C=C(\C)/CO

Technology Process of (6E)-8-hydroxygeranial

There total 4 articles about (6E)-8-hydroxygeranial 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:

(E/Z)-3,7-dimethyl-2,6-octadienal (5392-40-5,96680-15-8) → (2E,8E)-8-hydroxy-3,7-dimethyl-2,6-octadienal (80054-37-1) + (2E,6E)-3,7-dimethyl-2,6-octadiene-1,8-dial (80054-40-6) + (2Z,6E)-8-hydroxyneral (80054-36-0) + (2Z,6E)-3,7-dimethyl-2,6-octadiene-1,8-dial (80054-41-7)

Guidance literature:

With selenium(IV) oxide; In ethanol; for 0.75h; Yield given. Yields of byproduct given. Title compound not separated from byproducts; Heating;

Reference yield:

<1-(3)H>-10-hydroxygeraniol (108526-78-9) → (2E,6E)-8-hydroxy-2,6-dimethylocta-2,6-dienal (38290-51-6) + (2E,8E)-8-hydroxy-3,7-dimethyl-2,6-octadienal (80054-37-1) + (2E,6E)-3,7-dimethyl-2,6-octadiene-1,8-dial (80054-40-6)

Guidance literature:

With NAD; Rauwolfia serpentina cell suspension cultures, pH 6.5, incubation;

DOI:10.1016/S0040-4039(00)96530-4

Reference yield:

<1-(3)H>-10-hydroxygeraniol (108526-78-9) → (1R,4aS,7S,7aR)-nepetalactone (69252-84-2) + (2E,6E)-8-hydroxy-2,6-dimethylocta-2,6-dienal (38290-51-6) + (2E,8E)-8-hydroxy-3,7-dimethyl-2,6-octadienal (80054-37-1)

Guidance literature:

With 1,4-dihydronicotinamide adenine dinucleotide; NAD; for 2h; Rauwolfia serpentina cell suspension cultures, pH 6.5, incubation;

DOI:10.1016/S0040-4039(00)96530-4

upstream raw materials:

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

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

Downstream raw materials:

(S,E)-1-(6-((methoxymethoxy)methyl)-4-(4-methyl-5-hydroxypent-3-en-1-yl)cyclohexa-1,3-dien-1-yl)-2-(phenylsulfonyl)ethan-1-one

Refernces

• 1、 Battersby, Alan R.,Thompson, Mervyn,Gluesenkamp, Karl-Heinz,Tietze, Lutz-F.. "Investigations of the Biosynthesis of Indole Alkaloids. Feeding Experiments with Synthetic Radioactively Labelled Monoterpene Aldehydes". . p. 3430 - 3438. Retrieved 2007/10/02.