Vanillyl butyl ether Property

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

WGK Germany 

3

HS Code 

2909.50.4050

Hazard and Precautionary Statements (GHS)

Symbol(GHS)

Signal word

Warning

Hazard statements

H317May cause an allergic skin reaction

H319Causes serious eye irritation

Precautionary statements

P261Avoid breathing dust/fume/gas/mist/vapours/spray.

P264Wash hands thoroughly after handling.

P264Wash skin thouroughly after handling.

P272Contaminated work clothing should not be allowed out of the workplace.

P280Wear protective gloves/protective clothing/eye protection/face protection.

P302+P352IF ON SKIN: wash with plenty of soap and water.

P305+P351+P338IF IN EYES: Rinse cautiously with water for several minutes. Remove contact lenses, if present and easy to do. Continuerinsing.

P333+P313IF SKIN irritation or rash occurs: Get medical advice/attention.

P337+P313IF eye irritation persists: Get medical advice/attention.

P501Dispose of contents/container to..…

Vanillyl butyl ether Chemical Properties,Usage,Production

Description

Vanillyl butyl ether(82654-98-6) 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.

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 as a fragrance ingredient, oral care agent, hair conditioning agent, and warming or cooling 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.

Safety

Vanillyl butyl ether (VBE) is a weak skin sensitizer, which is a substance whose chemical structure indicates that it is expected to react with skin proteins, with a NESIL value of 3500 μg/cm2. VBE is not genotoxic, phototoxic or photosensitizing. In addition, VBE is not persistent, bioaccumulative and toxic (PBT) according to IFRA environmental criteria, and its risk quotient is less than 1 based on its current use in Europe and North America (i.e. PEC/PNEC). The local respiratory toxicity endpoint was evaluated using the Threshold of Toxicological Concern (TTC) for Cramer Class III materials, and exposure to VBE was below the TTC (0.47 mg/day)^[1].

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.

References

[1] A.M. API . RIFM fragrance ingredient safety assessment, vanillyl butyl ether, CAS Registry Number 82654-98-6[J]. Food and Chemical Toxicology, 2021, 153: Article 112361. DOI:10.1016/j.fct.2021.112361.