6963-56-0

Basic information

• Product Name: ANISYL BUTYRATE
• Synonyms: ANISYL BUTYRATE;FEMA 2100;4-Methoxybenzyl butyrate;Butanoic acid, (4-methoxyphenyl)methyl ester;Butyric acid, p-methoxybenzyl ester;Anisylbutyrat;ANISYL BUTYRATE, NATURAL;Butanoic acid 4-methoxybenzyl ester
• CAS NO: 6963-56-0
• Molecular Formula: C₁₂H₁₆O₃
• Molecular Weight: 194.23
• EINECS: 230-163-5
• Mol File: 6963-56-0.mol

Chemical Properties

• Boiling Point: 287℃
• Flash Point: 116℃
• Appearance: /
• Density: 1.045
• Vapor Pressure: 0.00264mmHg at 25°C
• Refractive Index: n20/D1.504
• CAS DataBase Reference: ANISYL BUTYRATE(CAS DataBase Reference)
• NIST Chemistry Reference: ANISYL BUTYRATE(6963-56-0)
• EPA Substance Registry System: ANISYL BUTYRATE(6963-56-0)

Safety Data

• WGK Germany: 2
• Hazardous Substances Data: 6963-56-0(Hazardous Substances Data)

Usage

Uses

Used in Flavor Industry:
Anisyl butyrate is used as a flavoring agent for its ability to intensify vanilla flavor and act as a fixative. It is commonly utilized in the production of ice cream, candy, and baked goods, with a recommended usage level of 5–15 ppm.
Anisyl butyrate is used as a synthetic flavoring agent for enhancing the vanilla flavor and providing a fixative effect in the Flavor Industry. It is particularly effective in the production of ice cream, candy, and baked goods, where it is used at a concentration of 5–15 ppm.

Preparation

From anisyl alcohol and n-butyric acid.

Metabolism

Esters of benzyl alcohol, such as the acetate, are rapidly hydrolysed in vivo to benzyl alcohol, which is then oxidized. The expected general reaction of primary aromatic alcohols in the animal body is oxidation to the corresponding aromatic acid, which is usually excreted as a glycine conjugate and to a lesser extent as an ester glucuronide. In rabbits, benzyl alcohol is almost entirely converted to benzoic acid, which is excreted mainly as hippuric acid . In substituted anisoles with a carboxyl group or a potential carboxyl group attached to the aromatic ring, the ether link is relatively stable

InChI:InChI=1/C12H16O3/c1-3-4-12(13)15-9-10-5-7-11(14-2)8-6-10/h5-8H,3-4,9H2,1-2H3

Synthetic route

butanoic acid methyl ester (623-42-7) + 4-Methoxybenzyl alcohol (105-13-5) → p-methoxybenzyl butyrate (6963-56-0)

Conditions	Yield
With basic alumina for 2h; Neat (no solvent); ball-milling;	81%

butyraldehyde (123-72-8) + 4-Methoxybenzyl alcohol (105-13-5) → p-methoxybenzyl butyrate (6963-56-0) + p-Methoxybenzyl bromide (2746-25-0) + 4-methoxy-benzaldehyde (123-11-5)

Conditions	Yield
With N,N,N,N,N,N-hexamethylphosphoric triamide; bromine; sodium hydrogencarbonate In dichloromethane; water	A 50% B 27% C 16%

butanoic acid anhydride (106-31-0) + N,N-dimethyl-4-methoxylbenzylamine (15175-54-9) → p-methoxybenzyl butyrate (6963-56-0)

butanoic acid anhydride (106-31-0) + 4-Methoxybenzyl alcohol (105-13-5) → p-methoxybenzyl butyrate (6963-56-0)

vinyl n-butyrate (123-20-6) + 4-Methoxybenzyl alcohol (105-13-5) → p-methoxybenzyl butyrate (6963-56-0)

Conditions	Yield
With polyvinyl alcohol : chitosan : lipase (Pseudomonas cepacia) 5:5:2.5 at 52℃; for 3h; Sonication; Enzymatic reaction;

Upstream product

• 123-72-8 butyraldehyde 
• 105-13-5 4-Methoxybenzyl alcohol 
• 623-42-7 butanoic acid methyl ester 
• 123-20-6 vinyl n-butyrate 
• 106-31-0 butanoic acid anhydride 
• 15175-54-9 N,N-dimethyl-4-methoxylbenzylamine 

Relevant articles and documents

The combine use of ultrasound and lipase immobilized on co-polymer matrix for efficient biocatalytic application studies

In this work, we have investigated the combine use of ultrasound and lipase (Pseudomonas cepacia: PCL) immobilized on co-polymer of polyvinyl alcohol (PVA) and chitosan (CHI) for biocatalytic applications. Initially, we have screened different free and immobilized biocatalysts to find-out the robust biocatalyst. The immobilized biocatalyst PVA:CHI:PCL (5:5:2.5) worked as a robust biocatalyst to provide superior conversion (99%) for the synthesis of model ultrasound assisted reaction. Subsequently, various reaction parameters were optimized in details to obtain the higher yield. Besides this, developed biocatalytic protocol was used to synthesize various industrially important butyrate compounds which provided excellent conversion of 99% under ultrasonic conditions. The developed biocatalyst showed excellent recyclability upto studied five cycles under ultrasonic condition. The immobilized PVA:CHI:PCL biocatalyst displayed 2.4 folds higher activity as compared to free lipases in ultrasonic condition. Moreover, PVA:CHI:PCL biocatalyst in ultrasound media showed 4.5 folds higher activity as compared to free lipases in conventional media. The energy assessment was performed which demonstrated feasibility of combine use of immobilization and ultrasonication to carry out efficient biocatalytic process.

Solvent-free transesterification in a ball-mill over alumina surface

An efficient procedure for transesterification has been developed in a ball-mill in the absence of any solvent, acid/base or metal catalyst. A variety of methyl, ethyl, allyl esters have been transesterified to higher benzyl and other esters in high yields by this procedure.

NEW OXIDATIVE ESTERIFICATION OF ALCOHOLS WITH ALDEHYDES BY THE Br2-HMPT-NaHCO3.

A new aldehyde-mediated oxidative esterification using a bromine/HMPT complex in the presence of sodium hydrogen carbonate is described.