Vanillyl butyl ether Chemical Properties

Boiling point:

241 °C(lit.)

Density 

1.057 g/mL at 25 °C(lit.)

vapor pressure 

0.42-2000Pa at 20-25℃

refractive index 

n20/D 1.516(lit.)

FEMA 

3796 | VANILLYL BUTYL ETHER

Flash point:

>230 °F

storage temp. 

Sealed in dry,Room Temperature

solubility 

soluble (Insoluble in water. Soluble in organic solvents, oils.)

form 

Oil

color 

Colourless

Specific Gravity

1.057

Odor

at 100.00 %. vanilla fruity

Odor Type

vanilla

Water Solubility 

1.79-1690mg/L at 20℃

JECFA Number

888

InChIKey

VLDFMKOUUQYFGF-UHFFFAOYSA-N

LogP

2.2-2.4 at 23-25℃

EPA Substance Registry System

Phenol, 4-(butoxymethyl)-2-methoxy- (82654-98-6)

Safety Information

WGK Germany 

3

HS Code 

2909.50.4050

MSDS

• Language:English Provider:SigmaAldrich

Vanillyl butyl ether Usage And Synthesis

Description

Vanillyl butyl ether is an ether of monohydroxybenzoic acid. It is added to food products as a flavoring agent. It is also present in cosmetics and personal care products. It has a characteristic trigeminal, burning, hot pepper nature and can be used in spice flavors like pepper, cinnamon and ginger, as well as blends for some baked applications, including cookies. It has some other applications include flavoring for alcoholic and non-alcoholic beverages with herbal, berry, vanilla, cola, ginger ale, root beer, hot chocolate, chai, ice tea and mints. It can also be used as a warming agent.

Chemical Properties

Vanillyl butyl ether has a weak, vanillic, acidic odor.

Uses

Vanillyl butyl ether is a compound hypothesized to have warming and vasodilation mechanisms when applied on the skin as a cream.

General Description

Vanillyl butyl ether is an alkoxy-substituted benzyl derivative mainly used as a flavoring agent.

Biochem/physiol Actions

Taste at 10-15%

Side effects

Vanilloids contain vanillyl groups that bind to the transient receptor potential type V1 channel (Vanilloid receptor-1, TRPV1) that respond to noxious stimuli such as high temperatures and acidic pH. This causes neurons to release glutamate, adenosine triphosphate (ATP) and a variety of neuropeptides, resulting in the warming sensation. Vanillyl butyl ether causes serious eye irritation and may cause an allergic skin reaction.

Synthesis

At present, the synthesis of vanillyl butyl ether is mainly obtained by dehydrating and condensing vanillyl alcohol and n-butyl alcohol under an acid catalyst. However, the yield of the method is low mainly because water generated by the reaction can inhibit the etherification reaction. The common acid catalyst such as AlCl is used3、FeCl3It is easy to hydrolyze in the presence of water and lose its catalytic action. A new synthesis method comprises the following steps: dissolving vanillin in a solvent, adding a metal complex hydride and an alkylating reagent after uniformly stirring, reacting for 3-4 hours at 30-40 ℃ to obtain a vanillin alcohol ether solution, and separating and purifying the vanillin alcohol ether solution to obtain vanillin alcohol ether.

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