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Zingerone

Zingerone structure

Zingerone 

structure
  • CAS No:

    122-48-5

  • Formula:

    C11H14O3

  • Chemical Name:

    Zingerone

  • Synonyms:

    2-Butanone,4-(4-hydroxy-3-methoxyphenyl)-;4-(4-Hydroxy-3-methoxyphenyl)-2-butanone;4-Hydroxy-3-methoxybenzylacetone;(4-Hydroxy-3-methoxyphenyl)ethyl methyl ketone;3-Methoxy-4-hydroxybenzylacetone;Vanillylacetone;Zingiberone;Zingerone;[0]-Paradol;Gingerone;NSC 15335

  • Categories:

    Cosmetic Ingredient  >  Perfuming

Description

White solid. Soluble in ether; sparingly soluble in water and petroleum ether. Zingerone has a strong, pungent odor reminiscent of ginger. It has a sharp taste, similar to ginger.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.


Solid|Yellowish to yellow-brown crystalline mass, sweet, spicy, warm, heavy floral, mildly animal balsamic, vanilla like odour


Zingerone is a methyl 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. It has a role as an antioxidant, an anti-inflammatory agent, a radiation protective agent, an antiemetic, a flavouring agent, a fragrance and a plant metabolite. It is a member of phenols, a monomethoxybenzene and a methyl ketone.|Zingerone is a pungent component of ginger.

Zingerone Basic Attributes

194.23

194.23

204-548-3

4MMW850892

15335

DTXSID8047420

Crystals from acetone, petroleum ether, ether plus petroleum ether

29333999

Characteristics

46.5

1.92240

Solid

1.138-1.139 g/cm3 @ Temp: 25 °C

40.5 °C

187-188 °C @ Press: 14 Torr

>230 °F

n 20/D 1.541(lit.)

Sparingly sol in water, petroleum ether; sol in ether, dil alkalies

2-8°C

0.000143mmHg at 25°C

STRONG, PUNGENT ODOR REMINISCENT OF GINGER

SHARP TASTE SIMILAR TO GINGER

YELLOWISH LIQUID /COMMERCIAL PRODUCT/

Safety Information

II; III

4.1

NONH for all modes of transport

2

36/37/38

26-36

EL8900000

SRP: At the time of review, criteria for land treatment or burial (sanitary landfill) disposal practices are subject to significant revision. Prior to implementing land disposal of waste residue (including waste sludge), consult with environmental regulatory agencies for guidance on acceptable disposal practices.

Zingerone is a food additive permitted for direct addition to food for human consumption as a synthetic flavoring substance and adjuvant in accordance with the following conditions: a) they are used in the minimum quantity required to produce their intended effect, and otherwise in accordance with all the principles of good manufacturing practice, and 2) they consist of one or more of the following, used alone or in combination with flavoring substances and adjuvants generally recognized as safe in food, prior-sanctioned for such use, or regulated by an appropriate section in this part.|OF DIRECT FOOD ADDITIVES- LIMITATIONS: SYNTHETIC FLAVOR.

Not Classified

Toxicity

REPORTED FOUND IN ESSENTIAL OIL OF ZINGIBER OFFICINALE.|Isolated from ginger root...

Drug Information

ORAL OR IP ADMIN OF 100 MG/KG /TO RATS/ RESULTED IN URINARY EXCRETION...MAINLY AS GLUCURONIDE AND/OR SULFATE CONJUGATES. WHILST UNCHANGED ZINGERONE ACCOUNTED FOR 50-55% OF DOSE, REDN TO CARBINOL (11-13%) ALSO OCCURRED.|/AFTER ORAL OR IP ADMIN OF 100 MG/KG ZINGERONE TO RATS/ SIDE CHAIN OXIDN TOOK PLACE AT THE 3 FEASIBLE SITES, AND OXIDN IN 3-POSITION PREDOMINATED TO YIELD C-6--C-2 METABOLITES. IDENTIFIED METABOLITES ACCOUNTED FOR 95-97% OF DOSE.|BILIARY STUDIES AND INVESTIGATIONS WITH CECAL MICRO-ORGANISMS IN VITRO /IN RATS/ INDICATED THAT SEVERAL OF THE URINARY O-DEMETHYLATED METABOLITES /OF ZINGERONE/ WERE OF BACTERIAL ORIGIN.

0 paradol

Zingerone Use and Manufacturing

Methods of Manufacturing

Isolated from ginger root or prepared from vanillin and acetone followed by catalytic hydrogenation: Nomura, J Chem Soc 111, 769 (1917); Nomura, US patents 1,263,796 (1918), 1,306,710 (1919); Cotton, US patent 2,381,210 (1945 to Penn Coal Prod Co).

Uses

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

COMMERCIAL PRODUCT CONTAINS A MINIMUM OF 93% ZINGERONE.

2-Butanone, 4-(4-hydroxy-3-methoxyphenyl)-: ACTIVE|FEMA NUMBER 3124; IT IS USED IN NON-ALCOHOLIC BEVERAGES (6.9 PPM); ICE CREAM, ICES, ETC (7.8 PPM); CANDY (11 PPM); BAKED GOODS (11 PPM); CHEWING GUM (15 PPM).

EPA Safer Chemical Functional Use Classes -> Fragrances|Safer Chemical Classes -> Yellow triangle - The chemical has met Safer Choice Criteria for its functional ingredient-class, but has some hazard profile issues|Food additives -> Flavoring Agents|Flavoring Agents -> JECFA Flavorings Index

Flavoring Agents

Computed Properties

Molecular Weight:194.23
XLogP3:0.8
Hydrogen Bond Donor Count:1
Hydrogen Bond Acceptor Count:3
Rotatable Bond Count:4
Exact Mass:194.094294304
Monoisotopic Mass:194.094294304
Topological Polar Surface Area:46.5
Heavy Atom Count:14
Complexity:191
Covalently-Bonded Unit Count:1
Compound Is Canonicalized:Yes

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