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.
