[6]-Shogaol;6-Shogaol

Base Information

• Chemical Name: [6]-Shogaol;6-Shogaol
• CAS No.: 555-66-8
• Molecular Formula: C17H24O3
• Molecular Weight: 276.376
• DSSTox Substance ID: DTXSID10873727
• Wikidata: Q105197280,Q110184380
• Mol file: 555-66-8.mol

Synonyms:[6]-Shogaol;6-Shogaol;trans-6-Shogaol;(E)-[6]-Shogaol;MFCD01736094;(6)-shogaol pound>>Shogaol;DTXSID10873727;HMS3874F13;BCP29765;AKOS028108461;SY231915;FT-0674572

Chemical Property of [6]-Shogaol;6-Shogaol

Chemical Property:

• Vapor Pressure: 6.55E-08mmHg at 25°C
• Refractive Index: 1.521
• Boiling Point: 427.5 °C at 760 mmHg
• PKA: 10.01±0.20(Predicted)
• Flash Point: 150.3 °C
• PSA: 46.53000
• Density: 1.033 g/cm³
• LogP: 4.03900
• Storage Temp.: 2-8°C
• Solubility.: Chloroform (Slightly), Ethyl Acetate (Slightly), Methanol (Slightly)
• XLogP3: 3.7
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 3
• Rotatable Bond Count: 9
• Exact Mass: 276.17254462
• Heavy Atom Count: 20
• Complexity: 299

Purity/Quality:

98% ^*data from raw suppliers

6-Shogaol ^*data from reagent suppliers

Safty Information:

• Pictogram(s): Xn
• Hazard Codes: Xn
• Statements: 22

MSDS Files:

SDS file from LookChem

Total 1 MSDS from other Authors

Useful:

• Canonical SMILES: CCCCCC=CC(=O)CCC1=CC(=C(C=C1)O)OC
• Uses: [6]-Shogaol is an aromatic constituent of ginger and the chain-dehydroxylated analog of [6]-Gingerol. [6]-Shogaol has activity very similar to [6]-Gingerol and produced an inhibition of spontaneous motor activity, antipyretic and analgesic effects, and prolonged hexobarbital-induced sleeping time. [6]-Shogaol also has potent antitussive activity and affected the cortical EEG.

Technology Process of [6]-Shogaol;6-Shogaol

There total 39 articles about [6]-Shogaol;6-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%

(+/-)-[6]-gingerol (23513-14-6,72749-01-0,74027-33-1,39886-76-5,1391-73-7) → [6]-shogaol (23513-13-5,104186-09-6,555-66-8)

Guidance literature:

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

DOI:10.1080/00397919908086182

Reference yield: 83.0%

[6]-shogaol → [6]-shogaol (23513-13-5,104186-09-6,555-66-8)

Guidance literature:

[6]-shogaol; With sodium hydroxide; In DMF (N,N-dimethyl-formamide); water; at 20 ℃; for 2h;

With hydrogenchloride; In DMF (N,N-dimethyl-formamide); water;

Reference yield: 80.0%

4-(4-hydroxy-3-methoxyphenyl)-2-butanone (122-48-5) + hexanal (66-25-1) → [6]-shogaol (23513-13-5,104186-09-6,555-66-8)

Guidance literature:

With DIMCARB; at 25 ℃;

DOI:10.1055/s-0029-1218389

upstream raw materials:

(+/-)-[6]-gingerol

hexanal

Dehydrozingerone

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

Downstream raw materials:

p-hydroxyphenethyl alcohol

homovanillyl alcohol

1-(4-hydroxy-3-methoxyphenyl)decane-3,5-diol

(-)-1-(4-hydroxy-3-methoxyphenyl)-3-oxodecane-5-sulfonic acid

Refernces

• 1、 Adamo, Mauro F. A.,Bencivenni, Grazia,Gillick-Healy, Malachi W.,Kelly, Brian G.,Moccia, Maria,Ravelli, Andrea. "First enantioselective synthesis of gingesulfonic acids and unequivocal determination of their absolute stereochemistry". supporting information. p. 1091 - 1094. Retrieved 2020/02/22.
• 2、 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.