23513-08-8

Basic information

• Product Name: 8-GINGEROL
• Synonyms: GINGEROL [8];5-HYDROXY-1-(4-HYDROXY-3-METHOXYPHENYL)-3-DODECANONE;(s)-(+)-3-dodecanon;(s)-(+)-5-hydroxy-1-(4-hydroxy-3-methoxyphenyl)-3-dodecanone;(5S)-1-(3-Methoxy-4-hydroxyphenyl)-5-hydroxydodecane-3-one;(5S)-5-Hydroxy-1-(4-hydroxy-3-methoxyphenyl)-3-dodecanone;(S)-10-Oxo-12-(3-methoxy-4-hydroxyphenyl)dodecane-8-ol;8-Gingerol ,98%
• CAS NO: 23513-08-8
• Molecular Formula: C₁₉H₃₀O₄
• Molecular Weight: 322.44
• Product Categories: Miscellaneous Natural Products
• Mol File: 23513-08-8.mol
• Article Data: 6

Chemical Properties

• Boiling Point: 476.4 °C at 760 mmHg
• Flash Point: 162.6 °C
• Appearance: white to light yellow/
• Density: 1.058 g/cm³
• Vapor Pressure: 6.94E-10mmHg at 25°C
• Refractive Index: 1.517
• Storage Temp.: 2-8°C
• Solubility: methanol: soluble1mg/mL, clear, colorless
• PKA: 10.02±0.20(Predicted)
• BRN: 2059802
• CAS DataBase Reference: 8-GINGEROL(CAS DataBase Reference)
• NIST Chemistry Reference: 8-GINGEROL(23513-08-8)
• EPA Substance Registry System: 8-GINGEROL(23513-08-8)

Safety Data

• Hazard Codes: Xi
• Statements: 43
• Safety Statements: 36/37
• WGK Germany: 3
• RTECS: JR4362000
• Hazardous Substances Data: 23513-08-8(Hazardous Substances Data)

Usage

Uses

8-Gingerol has been observed to exhibit anti-oxidant behaviour towards lipids and is effective in suppressing obesity and adipose tissue inflammation.

InChI:InChI=1/C19H30O4/c1-3-4-5-6-7-8-16(20)14-17(21)11-9-15-10-12-18(22)19(13-15)23-2/h10,12-13,16,20,22H,3-9,11,14H2,1-2H3/t16-/m0/s1

Upstream product

• 1619234-12-6 (S)-3-((tert-butyldimethylsilyl)oxy)decanoic acid 
• 502-44-3 hexahydro-2H-oxepin-2-one 
• 77398-92-6 5-hydroxy-1-(4-hydroxy-3-methoxyphenyl)dodecan-3-one 
• 1186501-40-5 [8]-dehydrogingerol 
• 146830-55-9 (+)<(S)R,2S>-1-(p-Tolylsulfinyl)-7-<(tert-butyldiphenylsilyl)oxy>-2-heptanol 

Relevant articles and documents

METHOD FOR PREPARING HIGHLY ENANTIO-ENRICHED GINGEROLS

Disclosed is a method for preparing a chiral Gingerol compound. To prepare the chiral Gingerol compound, a racemic Gingerol compound is treated with kinetic resolution in the presence of a chiral catalyst compound and an alkali metal fluoride so a chiral Gingerol compound with high optical purity can be prepared. An oligo ethylene glycol-derived compound including an oligo ethylene glycol functional group, a basic part, and a hydroxy functional group of a binol derivative, an acidic part, can be used as a chiral catalyst compound.COPYRIGHT KIPO 2020

Structure-Activity Relationships of 6- and 8-Gingerol Analogs as Anti-Biofilm Agents

Pseudomonas aeruginosa is a causative agent of chronic infections in immunocompromised patients. Disruption of quorum sensing circuits is an attractive strategy for treating diseases associated with P. aeruginosa infection. In this study, we designed and synthesized a series of gingerol analogs targeting LasR, a master regulator of quorum sensing networks in P. aeruginosa. Structure-activity relationship studies showed that a hydrogen-bonding interaction in the head section, stereochemistry and rotational rigidity in the middle section, and optimal alkyl chain length in the tail section are important factors for the enhancement of LasR-binding affinity and for the inhibition of biofilm formation. The most potent compound 41, an analog of (R)-8-gingerol with restricted rotation, showed stronger LasR-binding affinity and inhibition of biofilm formation than the known LasR antagonist (S)-6-gingerol. This new LasR antagonist can be used as an early lead compound for the development of anti-biofilm agents to treat P. aeruginosa infections.

An enantioselective synthesis of (+)-(S)-[n]-gingerols via the l-proline-catalyzed aldol reaction

An enantioselective approach to (+)-(S)-[n]-gingerols (1a-c) has been developed. The requisite stereogenic centers of target molecules are facilely constructed by the proline-catalyzed cross-aldol reaction from readily available achiral starting materials