Piperonyl acetone Property

Melting point:

49-54 °C(lit.)

Boiling point:

176 °C17 mm Hg(lit.)

Density 

1.175±0.06 g/cm3(Predicted)

FEMA 

2701 | 4-(3,4-METHYLENEDIOXYPHENYL)-2-BUTANONE

refractive index 

1.52-1.522

Flash point:

>230 °F

storage temp. 

4°C

solubility 

Chloroform (Slightly), DMSO (Slightly)

form 

Solid

color 

Colourless crystals.

Odor

at 10.00 % in dipropylene glycol. sweet raspberry heliotrope powdery cotton candy

Odor Type

floral

JECFA Number

2048

BRN 

169843

InChIKey

TZJLGGWGVLADDN-UHFFFAOYSA-N

LogP

1.53

CAS DataBase Reference

55418-52-5(CAS DataBase Reference)

NIST Chemistry Reference

4-(3,4-Methylenedioxyphenyl)-2-butanone(55418-52-5)

EPA Substance Registry System

2-Butanone, 4-(1,3-benzodioxol-5-yl)- (55418-52-5)

Safety

Safety Statements 

22-24/25

WGK Germany 

2

TSCA 

Yes

HS Code 

2914.19.0000

Toxicity

The acute oral LD₅₀ value in rats was reported as 4Og/kg and the acute dermal LD₅₀ value in rabbits exceeded 5 g/kg (Wohl, 1974).

Hazard and Precautionary Statements (GHS)

Symbol(GHS)

Signal word

Warning

Hazard statements

H315Causes skin irritation

H319Causes serious eye irritation

Precautionary statements

P264Wash hands thoroughly after handling.

P264Wash skin thouroughly after handling.

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.

P321Specific treatment (see … on this label).

P332+P313IF SKIN irritation occurs: Get medical advice/attention.

P362Take off contaminated clothing and wash before reuse.

Piperonyl acetone Chemical Properties,Usage,Production

Aroma

Intensely sweet, floral and very slightly woody-powdery odor reminiscent of the sweetfloral notes in Mimosa and Cassie. Also remotely reminiscent of Heliotrope.
The taste in dilutions below 50 ppm is sweet, somewhat fruity and "Cherry-pit"-like. Higher concentrations tend to show a somewhat bitter taste.

Uses in Perfume

For several decades well kept as a "secret" chemical this ketone is one of the most interest ing and successful condensation products from a perfumery point of view. Piperonyl acetone finds application in Lilac, Lily, Sweet Pea, Appleblossom, Mimosa, Cassie, Ylang-Ylang, Heliotrope, Carnation, etc. and is particularly interesting in lipstick perfumes, also because it blends well with lonones.
Piperonyl acetone finds use in flavor compositions for imitation Cherry ("pit flavor") in various fruit complexes. Occasionally as a modifier in Vanilla imitation. The concentration is about 8 to 45 ppm in finished products. The highest figures are usually in icecream, about 50 ppm.

Description

4-(3,4-Methylenedioxyphenyl)-2-butanone has an intensely sweet, floral, slightly woody odor. May be prepared by condensation of heliotropin with acetone, followed by hydrogenation in the presence of a palladium catalyst.

Chemical Properties

4-(3,4-Methylenedioxyphenyl)-2-butanone has an intensely sweet, floral, slightly woody odor reminiscent of raspberry, cotton candy (i.e., candy floss) with a cassie, heliotrope association.

Occurrence

Has apparently not been reported to occur in nature.

Definition

ChEBI: 4-(3,4-Methylenedioxyphenyl)-2-butanone is a member of benzodioxoles.

Preparation

By condensation of heliotropin with acetone, followed by hydrogenation in the presence of a palladium catalyst

Taste threshold values

Taste characteristics at 40 ppm: sweet, berry-like with spicy, jamy nuances

Metabolism

The oxygen-aromatic carbon link of aromatic ethers is generally biologically stable, and possible metabolites include the p-hydroxy derivative of the ether, the phenol or the p-hydroxyphenol (Williams, 1959). Ketones are not readily metabolized in the body. As a derivative of 2-butanone, piperonyl acetone might be expected to be partially reduced to the secondary alcohol and excreted as the glucuronide (Williams, 1959), since Saneyoshi (1911) isolated the glucuronide of 2-butanol from the urine of rabbits receiving methyl ethyl ketone.