Zingerone

Product Name:

Zingerone

Synonyms:

(0)-paradol;[0]-Paradol;3-Methoxy-4-hydroxybenzylacetone;3-methoxy-4-hydroxy-benzylacetone;4-(3-methoxy-4-hydroxyphenyl)-2-butanone;4-(4-hydroxy-3;Gingerone;zingerone [3-(4-hydroxy-3-methoxyphenyl)butan-2-one]

CAS:

122-48-5

MF:

C11H14O3

MW:

194.23

EINECS:

204-548-3

Product Categories:

Miscellaneous Natural Products;chemical reagent;pharmaceutical intermediate;phytochemical;reference standards from Chinese medicinal herbs (TCM).;standardized herbal extract;Inhibitors

Mol File:

122-48-5.mol

Melting point 

40-41 °C(lit.)

Boiling point 

141 °C0.5 mm Hg(lit.)

density 

1.14 g/mL at 25 °C(lit.)

FEMA 

3124 | ZINGERONE

refractive index 

n20/D 1.541(lit.)

Fp 

>230 °F

storage temp. 

2-8°C

pka

10.03±0.20(Predicted)

JECFA Number

730

Merck 

14,10166

InChIKey

OJYLAHXKWMRDGS-UHFFFAOYSA-N

CAS DataBase Reference

122-48-5(CAS DataBase Reference)

NIST Chemistry Reference

2-Butanone, 4-(4-hydroxy-3-methoxyphenyl)-(122-48-5)

EPA Substance Registry System

2-Butanone, 4-(4-hydroxy-3-methoxyphenyl)- (122-48-5)

Risk Statements 

36/37/38

Safety Statements 

26-36

WGK Germany 

2

RTECS 

EL8900000

TSCA 

Yes

HS Code 

29333999

Hazardous Substances Data

122-48-5(Hazardous Substances Data)

Food flavorings

Vanillylacetone also called zingerone , is a food spice which is allowed to be prepared   appropriately according to production needs by Chinese "Sanitary Standards of Using Food Additives" (GB 2760-1996),its chemical name is 4-(4-hydroxy 3-methoxyphenyl)-2-butanone. Yellow or light amber crystal (acetone, petroleum ether or ethyl ether-petroleum ether), at room temperature, after long time ,it becomes to a viscous liquid.It  has a strong irritating odor like spicy ginger and ginger-like pungent taste,it has a sweet, spicy, full-bodied and deep floral aroma, fragrance lasts for a long time. The relative density is 1.138~1.139 (25 ℃), melting point 40~41 ℃, boiling point 290 ℃ (102 ℃), refractive index 1.544~1.545. It  can be dissolved in 50% ethanol in 1:1 ratio , slightly soluble in water and petroleum ether, soluble in dilute alkali. In the steam it slowly evaporates. When heated ,it can deoxidate silver nitrate ammonia solution; and it can react with an alcohol solution of ferric chloride to turn to green. It is derived from the Zingiber officinale essential oils , Vanillylacetone is the main constituent of ginger oil . After the condensation reaction of vanillin and acetone,it is obtained through hydrogenation .it is used as a full-bodied flavor sweeteners and edible flavorings. In the perfumed products ,it can have a "leather", "tobacco" flavor. It is not easy to change color.
Vanillylacetone can be used in the formulation of flavors, it is mainly used as sweeteners for rich aromas and flavors , in very small quantities, the application range is very small. IFRA has no restrictions.
Vanillylacetone is recognized as GRAS by FEMA , FEMA number is 3124, and it is  approved by the FDA for human consumption,it is included in the artificial flavor table by the Council of Europe in the level of 15mg/kg dosage which can be used in foods and is not harmful to human health . Vanillylacetone can be used for food flavor and seasoning product formulations.
FEMA provides: Vanillylacetone highest reference amount is  soft drinks, 6.9mg/kg; ice cream, ices, 7.8mg/kg; candy, 11mg/kg; baked goods, 11mg/kg; chewing gum, 15mg/kg.

Content Analysis

Use gas chromatography (GT-10-4) nonpolar column method for the determination.

Toxicity

GRAS (FEMA).
LD502.58g/kg (rat, dictation).

Limited use

FEMA (mg/kg): Soft drinks 6.9; cold:7.8 ; confectionery, bakery products, 11.0; Chewing Gum:15.0 
FDA, §172.515: the right amount limit.

Chemical Properties

White solid. Soluble in ether; sparingly soluble in water and petroleum ether.

Chemical Properties

Zingerone has a strong, pungent odor reminiscent of ginger. It has a sharp taste, similar to ginger.

Uses

Vanillylacetone is a phenolic compound that naturally occurs in cranberry and ginger. Studies shows that Vanillylacetone exhibits variable cytotoxic, cytoprotective and antioxidant activity against li ver and human tumor cells. Vanillylacetone is also used in herbal medicine for various purposes.

Uses

In fragrances, flavors and cosmetics; in artificial spice oils.

Definition

ChEBI: A ketone that is 4-phenylbutan-2-one in which the phenyl ring is substituted at positions 3 and 4 by methoxy and hydroxy groups respectively. The major pungent component in ginger.

Preparation

By condensation of vanillin with acetone followed by hydrogenation.

Aroma threshold values

Aroma characteristics at 10.0%: low impacting, creamy, spicy eugenol clove-like with a slight balsamic vanilla-like note.

Taste threshold values

Taste characteristics at 80 ppm: spicy with a biting, lingering heat. Taste characteristics at 20 ppm in 5% sugar solution: smooth, sweet, creamy and warm, spicy clove with a slight lingering burning bite.

Safety Profile

Moderately toxic by ingestion. A skin irritant. A flammable liquid. When heated to decomposition it emits acrid smoke and irritating fumes.