Flavorant compositions

Details Flavorant compositions Flavorant compositions

2000-08-08

2002-11-05

Killos, Paul J. (Department: 1623)

Organic compounds -- part of the class 532-570 series

Organic compounds

Carboxylic acid esters

Reexamination Certificate

active

06476252

ABSTRACT:

FIELD OF THE INVENTION
The present invention relates to a flavorant composition exhibiting warm/hot, spicy and pungent sensations related to Galangal. More particularly, it relates to a flavorant composition comprising at least one 1′-acetoxychavicol acetate or 1′-acetoxyeugenol acetate derivative. The present invention also relates to food, beverages or healthcare products containing a flavorant composition of the present invention as well as a method of flavoring food, beverages or healthcare products using the flavorant composition.
BACKGROUND
Hot peppers like red pepper (
Capsicum annuum L.
)—in Europe also known as Paprika—and chili pepper (
Capsicum frutescens L.
) comprise an essential ingredient in a number of Asian and European cuisines. It is well known from Thresh et al.,
Pharm. J. and Trans.
(1876), 7, 21; Micko et al., Z.
Nahr. Genussm.
(1898), 1, 818 or A. Szallasi, P. M. Blumberg,
Adv. Pharmacol.
(1993), 24, 123 that Capsaicin is the active ingredient in hot peppers of the plant genus Capsicum. As mentioned in A. Szallasi,
Gen. Pharmac.
(1994), 25, 223 the oral consumption of hot peppers leads to profuse perspiration which ultimately leads to heat loss. This well established effect, which is known as gustatory sweating, is most probably the reason for the high popularity of hot peppers in countries in hot climates, as well as the flavoring of food.
Capsaicin is one of the most active members of a class of compounds commonly referred to as capsaicinoids, see J. Szolcsanyi in,
Handbook of Experimental Pharmacology,
A. S. Milton, Ed., Vol. 60, pp. 437-478, Springer, Berlin, (1982). Other well known compounds of this class are Piperine, the active ingredient in black pepper (
Piper nigrum L.
), see Cazeneuve et al.,
Bull. Soc. Chim. France.
(1877), 27, 291, and Gingerol, the active ingredient in ginger (
Zingiber officinale R.
).
Galangal (also called galanga, galingale, galangale, calangall) is the name for a member of the monocotyledonus family
Zingiberacea. Alpinia officinarium,
the smaller Galangal, is native to southern China, while the greater Galangal,
Alpinia galanga
or
Languas galanga,
is a larger plant native to Java and Malaya.
Alpinia galanga
is a stemless perennial herb with fragrant short living flowers. The reddish-brown rhizomes of this plant, having a spicy aroma and a pungent taste somewhere in between pepper and ginger, are used as a spice and especially as a ginger substitute for flavoring foods, e.g. meat, rice or curry. Galangal oleoresin is used as a modifier for ginger, cardamom, allspice, nutmeg etc. with which it blends favorably. The oleoresin remains, however, a rarity and specialty, which is offered by flavor supply houses.
The compounds 1′-acetoxychavicol acetate and 1′-acetoxyeugenol acetate are known compounds. They have been isolated from
Alpinia galanga
and are described to have anti-tumor activity (see H. Itokawa et al.,
Planta Medica
((1987), 32-33), to inhibit xanthin oxidase (see T. Noro et al.,
Chem. Pharm. Bull.
(1988), 36, 244) and to have anti-fungal activity (see A. M. Janssen et al.,
Planta Medica
1985, 507). Furthermore, 1′-acetoxychavicol acetate is described to have anti-ulcer activity (see S. Mitsui et al.,
Chem. Pharm. Bull.
(1976), 24, 2377) and to be a potent inhibitor of the tumor promoter-induced Epstein-Barr virus activation (see A. Kondo et al.,
Biosci. Biotech. Biochem.
(1993), 57,1344). H. Mori et al.,
Nippon Shokuhin Kagaku Kogaku Kaishi
(1995), 42, 989. 1-acetoxychavicol acetate is an aroma constituent of Galanga as determined by GC olfactometry, i.e. they determined only the retronasal aroma by GC sniffing without having tested the trigeminal effect of this constituent.
SUMMARY OF THE INVENTION
The present invention provides 1′-acetoxychavicol acetate and 1′-acetoxyeugenol acetate and derivatives thereof which exhibit a strong trigeminal effect which causes a warm/hot, spicy and pungent sensation perceived upon tasting any form of spice which is related to Galangal.
The present invention also provides a method of flavoring food, beverage or healthcare products using the flavorant composition of the present invention as well as the flavored food, beverage or healthcare products.
DETAILED DESCRIPTION OF THE INVENTION
According to the invention at least one compound selected from the group consisting of 1′-acetoxychavicol acetate, 1′-acetoxyeugenol acetate and related compounds of formula I
wherein
A=H, OR
4
X=OH, OCOR
1
Y=H, OCOR
3
and
R
1
, R
3
=H, branched or unbranched C
1-6
alkyl, C
2-6
alkenyl, C
2-6
alkinyl,
R
2
=H, branched or unbranched, substituted or unsubstituted C
1-6
alkyl, C
2-6
alkenyl, C
2-6
alkinyl, C
3
-C
6
C
6
carbocycle,
R
4
=branched or unbranched C
1-6
alkyl, C
2-6
alkenyl, C
2-6
alkinyl,
is added to a flavorant acceptable carrier to produce a flavorant composition exhibiting warm/hot, spicy and pungent sensations related to Galangal.
The effect is somewhat similar to those elicited by capsaicin and other capsaicinoids derived from hot peppers, by piperine derived from black pepper, by gingerols derived from ginger and by isothiocyanates derived from mustard. However, all of the latter compounds impart usually long-lasting sensations which are very often undesirable, especially if spicy foods are consumed with more delicately flavored food and/or drink, e.g. with red wine. In contrast, the flavorant composition according to the invention surprisingly produce a pungency of relatively short duration, which makes them ideal for flavoring foods where a lingering effect is undesirable.
In addition, the flavorant compositions of the invention have a warming, alcohol-boosting effect in alcoholic beverages, e.g. making a beverage containing about 15% alcohol taste like one containing about 30% alcohol.
The flavorant composition comprising the compounds of formula I may be used in either enantiomeric form, in any ratio of enantiomers or in racemic form.
The flavorant composition of the invention exhibits Galangal related effects of warm/hot, spicy and pungent sensations to food products, beverages and consumer healthcare products, e.g. mayonnaise, sour cream, onion dip, vegetable dip, potato chip snack, chewing gum, hard candy, mouthwash, toothpaste, etc.
The novel compounds of the flavorant compositions are listed in Table I.
TABLE I




















wherein R is H, CH
3
, CH
2
CH
3
, or CH(CH
3
)
2
.
All these compounds exhibit the above mentioned warm/hot, spicy and pungent sensations and are preferred. The most preferred compounds for use in flavorant compositions are listed in Table II.
TABLE II









Thus, according to the invention a flavorant composition contains at least one synthetically prepared compound of formula I and a flavorant acceptable carrier and exhibits warm/hot, spicy and pungent sensations related to Galangal. The flavorant compositions may be naturally occurring and are therefore preferred. The compounds of formula I, preferably those of Table I, more preferably those of Table II, might be used to generate the above mentioned effects in a variety of food, beverages or consumer healthcare products, e.g. in hard candy, chewing gum, mayonnaise, sour cream, onion and other vegetable dips, potato chip snack, alcoholic cordial, mouthwash and toothpaste. The compounds of formula I do not suffer the serious disadvantage of lingering hotness nor do they exhibit other negative effects characteristic of lingering food ingredients like capsaicin, gingerol and piperine.
Further, the appropriate compounds for the flavorant composition may be readily prepared by methods known to those skilled in the art. The preferred method for the preparation of compounds of formula I involves the following steps a) to c):
a) A halo-alkane-, alkene-, or alkine of type R
2
X, where X is a halogen atom and R
2
has the above defined meaning, is reacted with magnesium to form a Grignard reagent of type R
2
MgX. The reaction wi

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