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Gingerol compounds and their use as flavor modifiers

A kind of technology of compound and mixture, applied in the field of gingerol compounds

Pending Publication Date: 2021-08-06
FIRMENICH SA +1
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

However, potassium chloride tastes salty and bitter, and this bitterness is a problem with the sensory effect of replacing sodium chloride

Method used

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  • Gingerol compounds and their use as flavor modifiers
  • Gingerol compounds and their use as flavor modifiers
  • Gingerol compounds and their use as flavor modifiers

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0243] The separation of embodiment 1.[6]-gingerol, [8]-gingerol or [10]-gingerol

[0244] A plant extract containing [6]-gingerol as a main component such as ginger extract (Layn-CN nominal 75%, NMR: 55%) was dissolved in methanol, followed by washing 3 times with cyclohexane to obtain the product. The product was purified on a RP-18 silica gel column (GraceReveleris, H 2 O / ACN 50:50) on flash chromatography to obtain [6]-gingerol (α D +23.2° (c=1, CHCl 3 )), [8]-gingerol (α D +15.1° (c=1, CHCl 3 )) or [10]-gingerol (α D +16° (c=1, CHCl 3 )).

Embodiment 2

[0245] The synthesis of embodiment 2.[6]-gingerdiol

[0246] Diethyl(methoxy)borane (2.1 mL; 15.98 mmol) was added to [6]-gingerol (4.0 g, 13.32 mmol) in 120 mL THF / MeOH (4:1) at -78 °C in the solution. The reaction mixture was stirred at -78 °C for 30 min, then NaBH was added 4 (0.605 g; 15.98 mmol). The reaction mixture was stirred at -78°C for 3 hours, and 30% H 2 o 2 (48 mL), a mixture of phosphate buffer (pH=7; 96 mL) and MeOH (methanol, 96 mL). Evaporate the solvent and wash with CH 2 Cl 2 The remaining aqueous phase was extracted twice. The combined organic phases were washed with water. use Na 2 SO 4 Dry and evaporate. The residue was treated with 8.0 mL of glacial acetic acid (acetic acid) in 120 mL of EtOAc (ethyl acetate) at room temperature to complete the decomposition of the diol borate. The mixture was stirred at room temperature for 2 h and washed with 40 mL of saturated NaHCO 3 Quenched. Then, it was extracted 2 times with EtOAc. The combined ...

Embodiment 3

[0247] Embodiment 3.[6]-Synthesis of Gingeriol Diacetate

[0248] Triethylamine (5.56g, 4 equivalents), acetic anhydride (4.91g, 3.5 equivalents) and 4-dimethylaminopyridine (DMAP, 67mg, 0.3 equivalents) were continuously added to [6]-gingerdiol (4.2g, 13.7mmol) in a solution in 120mL. The reaction mixture was stirred overnight and worked up. The product was purified by flash chromatography (heptane:EtOAc, 6:4) to yield 3.6 g (61%) of [6]-gingertriacetate. A solution of [6]-ginger triacetate (2.4 g, 5.7 mmol) in pyrrolidine (24 ml) was stirred at room temperature for 1.5 hours. After work-up and flash chromatography (heptane:EtOAc, 6:4), 1.49 g (69%) of [6]-gingeriol diacetate was obtained as off-white oil (α D -1.2° (c=1, CHCl 3 )).

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Abstract

The present disclosure relates to gingerol compounds, whether in their diol form or as a derivative, and their use to enhance the salty taste or the umami taste of a flavored article. The disclosure also provides compositions and flavored products containing such compounds. In some embodiments, the flavored products have reduced amounts of salt or umami-enhancing compounds (glutamates, arginates, purinic ribonucleotides, such as inosine monophosphate (IMP) and guanosine monophosphate (GMP)), relative to comparable flavored products that do not incorporate the gingerol compounds. The disclosure further provides methods of making monoacetate or diacetate derivatives of gingerol diols.

Description

[0001] Cross References to Related Applications [0002] This application claims priority from PCT International Application PCT / CN2019 / 116958, filed 11 November 2019, and European Patent Application 19214925.0, filed 10 December 2019, both of which are incorporated herein by reference in their entirety as if in This statement is the same. technical field [0003] The present disclosure relates to gingerol compounds, whether in diol form or as derivatives thereof, and their use for enhancing the salty or umami taste of flavored products. The present disclosure also provides compositions and flavored products comprising such compounds. In some embodiments, the flavored product has reduced amounts of salt-enhancing or umami-enhancing compounds (glutamate, arginine, purine ribose) relative to comparable flavored products that do not incorporate gingerol compounds. Nucleotides such as inosine monophosphate (IMP) and guanosine monophosphate (GMP)). The present disclosure also pr...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): A23L27/20A23L27/40A23L2/56A61K8/34A61Q11/00
CPCA23L27/204A23L27/40A23L2/56A61K8/347A61Q11/00A23V2002/00A23V2250/2132C07C43/23C07C41/26C07C67/08C07C69/18A23L27/10A23L27/88
Inventor H·芒特E·弗莱罗特M·雷特尔N·杰克勒曼H·帕明格甘贤文
Owner FIRMENICH SA