Gingerdiol

Base Information

• Chemical Name: Gingerdiol
• CAS No.: 154905-69-8
• Molecular Formula: C17H28O4
• Molecular Weight: 296.407
• UNII: 4C9F8U79BX
• ChEMBL ID: CHEMBL2071442
• Nikkaji Number: J1.572.527C
• Wikidata: Q27259404
• Mol file: 154905-69-8.mol

Synonyms:Gingerdiol;6-Gingerdiol;(+)-(6)-Gingerdiol;(6)-Gingerdiol, (+)-;(3R,5S)-(6)-Gingerdiol;154905-69-8;UNII-4C9F8U79BX;4C9F8U79BX;3R,5S-Decanediol, 1-(4-hydroxy-3-methoxyphenyl)-;6-Gingerdiol (constituent of ginger) [DSC];3,5-Decanediol, 1-(4-hydroxy-3-methoxyphenyl)-, (3R,5S)-;(3R,5S)-1-(4-hydroxy-3-methoxyphenyl)decane-3,5-diol;CHEMBL2071442;SCHEMBL23370835;6-Gingerdiol (constituent of ginger);AKOS040762919;Q27259404

Chemical Property of Gingerdiol

Chemical Property:

• XLogP3: 3
• Hydrogen Bond Donor Count: 3
• Hydrogen Bond Acceptor Count: 4
• Rotatable Bond Count: 10
• Exact Mass: 296.19875937
• Heavy Atom Count: 21
• Complexity: 259

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

• Canonical SMILES: CCCCCC(CC(CCC1=CC(=C(C=C1)O)OC)O)O
• Isomeric SMILES: CCCCC[C@@H](C[C@@H](CCC1=CC(=C(C=C1)O)OC)O)O

Technology Process of Gingerdiol

There total 22 articles about Gingerdiol 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%

C19H30O5 (371972-57-5) → (3R,5S)-1-(4-hydroxy-3-methoxyphenyl)decane-3,5-diol (154905-69-8)

Guidance literature:

With potassium carbonate; In methanol; at 20 ℃; for 0.666667h;

DOI:10.1002/ejoc.201301727

Reference yield: 98.0%

[6]-gingerol (39886-76-5,72749-01-0,74027-33-1,23513-14-6,1391-73-7) → (3R,5S)-1-(4-hydroxy-3-methoxyphenyl)decane-3,5-diol (154905-69-8)

Guidance literature:

[6]-gingerol; With diethyl methoxy borane; In tetrahydrofuran; methanol; at -78 ℃; for 0.5h;

With sodium tetrahydroborate; In tetrahydrofuran; methanol; at -78 ℃; for 3h; Further stages;

Reference yield: 67.0%

→ (3R,5S)-1-(4-hydroxy-3-methoxyphenyl)decane-3,5-diol (154905-69-8)

Guidance literature:

With ethanol; nickel; at 20 ℃;

DOI:10.1016/S0040-4039(01)01263-1

upstream raw materials:

[6]-gingerol

(S)-1-(4-(benzyloxy)-3-methoxyphenyl)-5-(tert-butyldimethylsilyloxy)dec-1-yn-3-one

C₃₀H₄₄O₄Si

(5S)-5-{[tert-butyl(dimethyl)silyl]oxy}-1-(4-hydroxy-3-methoxyphenyl)decan-3-one

Downstream raw materials:

(3R,5S)-1-(4-(benzyloxy)-3-methoxyphenyl)decane-3,5-diyl diacetate

(3R,5S)-1-(3,4-dimethoxyphenyl)decane-3,5-diyl diacetate

(3R,5S)-1-(4-hydroxy-3-methoxyphenyl)decane-3,5-diyl diacetate

(3R,5S)-3,5-Diacetoxy-1-(3-methoxy-4-acetoxyphenyl)decane

Refernces

• 1、 -. "GINGEROL COMPOUNDS AND THEIR USE AS FLAVOR MODIFIERS". Page/Page column 55. . Retrieved 2021/05/21.
• 2、 Sabitha, Gowravaram,Srinivas, Chitti,Reddy, Teega Rammohan,Yadagiri, Kurra,Yadav, Jhillu Singh. "Synthesis of gingerol and diarylheptanoids". . p. 2124 - 2133. Retrieved 2012/03/27.