(8)-Shogaol

Base Information

• Chemical Name: (8)-Shogaol
• CAS No.: 104186-07-4
• Molecular Formula: C₁₉H₂₈O₃
• Molecular Weight: 304.43
• UNII: AV4IK2HCNT
• Nikkaji Number: J506.158J
• Wikidata: Q27274135
• Metabolomics Workbench ID: 44894
• ChEMBL ID: CHEMBL25893
• Mol file: 104186-07-4.mol

Synonyms:(8)-shogaol;8-shogaol

Chemical Property of (8)-Shogaol

Chemical Property:

• PSA: 46.53000
• LogP: 4.81920
• XLogP3: 4.8
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 3
• Rotatable Bond Count: 11
• Exact Mass: 304.20384475
• Heavy Atom Count: 22
• Complexity: 325

Purity/Quality:

98% ^*data from raw suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

• Canonical SMILES: CCCCCCCC=CC(=O)CCC1=CC(=C(C=C1)O)OC
• Isomeric SMILES: CCCCCCC/C=C/C(=O)CCC1=CC(=C(C=C1)O)OC

Technology Process of (8)-Shogaol

There total 10 articles about (8)-Shogaol 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: 95.0%

5-hydroxy-1-(4-hydroxy-3-methoxyphenyl)dodecan-3-one (77398-92-6) → [8]-shogaol (36700-45-5,104186-07-4)

Guidance literature:

With hydrogenchloride; In tetrahydrofuran; for 4h; Heating;

DOI:10.1080/00397919908086182

Reference yield: 57.0%

Octanal (124-13-0) + 4-(4-hydroxy-3-methoxyphenyl)-2-butanone (122-48-5) → [8]-shogaol (36700-45-5,104186-07-4)

Guidance literature:

With DIMCARB; at 20 ℃; for 72h;

DOI:10.1039/c9ob02662b

Reference yield: 47.0%

5-hydroxy-1-(4-hydroxy-3-methoxyphenyl)dodecan-3-one (77398-92-6) → [8]-shogaol (36700-45-5,104186-07-4) + [8]-gingerol (23513-08-8,77398-92-6,107257-17-0,135272-33-2)

Guidance literature:

With potassium fluoride; C₅₀H₃₄F₁₂O₆; In toluene; at 25 ℃; for 192h; enantioselective reaction; Inert atmosphere; Resolution of racemate;

DOI:10.1021/acs.orglett.8b00547

upstream raw materials:

5-hydroxy-1-(4-hydroxy-3-methoxyphenyl)dodecan-3-one

5-hydroxy-1-[3-methoxy-4-(tetrahydro-pyran-2-yloxy)-phenyl]-dodecan-3-one

Dehydrozingerone

4-(4-hydroxy-3-methoxyphenyl)-2-butanone

Refernces

• 1、 Paladhi, Sushovan,Hwang, In-Soo,Yoo, Eun Jeong,Ryu, Do Hyun,Song, Choong Eui. "Kinetic Resolution of β-Hydroxy Carbonyl Compounds via Enantioselective Dehydration Using a Cation-Binding Catalyst: Facile Access to Enantiopure Chiral Aldols". supporting information. p. 2003 - 2006. Retrieved 2018/04/16.
• 2、 Kim, Darrick S. H. L.,Kim, Jin Yung. "Side-chain length is important for shogaols in protecting neuronal cells from β-amyloid insult". . p. 1287 - 1289. Retrieved 2007/10/03.