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(12) Patent Application Publication (10) Pub. No.: US 2012/0231140 A1 Hofmann Et Al

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(12) Patent Application Publication (10) Pub. No.: US 2012/0231140 A1 Hofmann Et Al US 201202311 40A1 (19) United States (12) Patent Application Publication (10) Pub. No.: US 2012/0231140 A1 Hofmann et al. (43) Pub. Date: Sep. 13, 2012 (54) ORGANIC COMPOUNDS Publication Classification (51) Int. Cl. A2.3L. I./226 (2006.01) (75) Inventors: Thomas Frank Hofmann, CD7C 69/45 (2006.01) Neufahrn (DE); Andreas A2.3L 2/56 (2006.01) Degenhardt, Erfstadt (DE) (52) U.S. Cl. ......................................... 426/534; 560/262 (57) ABSTRACT (73) Assignee: GIVAUDANSA, Vernier (CH) Provided are umami taste and savoury flavour enhancing compounds of formula (I) (21) Appl. No.: 13/389,020 (I) (22) PCT Filed: Aug. 20, 2010 (86). PCT No.: PCT/EP2010/06216O OH RI S371 (c)(1), (2), (4) Date: May 24, 2012 wherein R' is selected from 0 and OH, the dotted line repre senting a bond present when R' is 0, R’ is a hydrocarbon residue having 6 to 22 carbon atoms, (30) Foreign Application Priority Data comprising from 0-4 unsaturated carbon-carbon bonds. The compounds can be added to food products, beverages and Aug. 20, 2009 (GB) ................................... O914574.9 other consumable products. US 2012/02311 40 A1 Sep. 13, 2012 ORGANIC COMPOUNDS flavour of a composition, comprising at least one umami tastant, by adding to the aforementioned composition at least one compound of formula (I) 0001. This invention relates to compounds that are useful in the enhancement of umami taste and savoury flavour, and (I) to their use in compositions and consumable products that O contain umami tastants. 0002 Umami is one of the basic tastes and has been us R2 described as a savoury or meaty flavour. It is an attribute of O many foods, in particularly savoury foods. OH R 0003 Umami taste and savoury flavour is elicited by the salts of glutamic acid, particularly monosodium glutamate 0015 wherein R' is selected from O and OH, the dotted (MSG), and these compounds may therefore be used to line representing a bond present when R' is O, modify the umami taste and savoury flavour of consumable 10016 R is a hydrocarbon residue having 6 to 22 carbon products. However, some consumers are believed to be atoms, comprising from 0-4 unsaturated carbon-carbon adversely affected by glutamate salts, in particularly MSG, bonds. and consequently there is a need for compounds that are not 0017. In another particular embodiment compounds of based on glutamate to replace or reduce reliance on Such formula (I) are selected from the group consisting of: compounds for modifying the umami taste and savoury fla 0018 1-acetoxy-2-hydroxy-4-oxo-n-heneicosa-5,12,15 Vour of consumable products. trien; 1-acetoxy-2,4-dihydroxy-n-heneicosa-12, 15-dien; 0004. It is known in the art that the umami taste and 1-acetoxy-2,4-dihydroxy-n-heptadeca-16-yne: 1-acetoxy-2- savoury flavour of a consumable product can be enhanced by hydroxy-4-keto-n-octadeca-12-en; 1-acetoxy-2,4-dihy the addition of the naturally-occurring purine nucleotides droxy-n-heptadeca-16-en; 1-acetoxy-2-hydroxy-4-oxo-n- inosine monophosphate (IMP) and guanosine monophos heneicosa-12, 15-dien; 1-acetoxy-2-hydroxy-4-keto-n- phate (GMP). However, these compounds are difficult and heptadeca-16-en; 1-acetoxy-2-hydroxy-4-keto-n- expensive to produce, thus limiting their use in the industry. heptadecane. 0005. There remains a need for compounds that are useful 0019. The compounds according to the present invention in the enhancement of umami taste and savoury flavour which may comprise at least one chiral centre, and as Such may exist do not suffer from the drawbacks of the prior art. as a mixture of stereoisomers. If it is desired to prepare 0006 Through the provision of enhancing compounds individual stereoisomers, this may be achieved according to that are non-glutamate in nature, reliance on compounds, methodology known in the art, e.g. preparative HPLC and GC Such as MSG, for modifying the umami taste and savoury or by stereoselective syntheses. flavour of compositions and consumable products may be 0020. In the present invention the use of the term a com reduced. pound of formula (I) may refer to both a racemic mixture or 0007. The present invention also relates to the use of com the individually isolated isomers. pounds of formula (I) defined hereinbelow to enhance the 0021. The compounds of formula (I) may be added into a umami taste and savoury flavour of consumable products and composition in any Suitable form for example neat form, or in compositions comprising at least one umami tastant. a solvent, or in a modified form for example they may first be 0008. The present invention also relates to methods of entraped with an entrapment material Such as polymers, cap enhancing the umami taste and savoury flavour of composi Sules, microcapsules, nanocapsules, liposomes, precursors, tions and consumable products comprising at least one film formers, absorbants such as by using carbon Zeolites, umami tastant, by adding to said consumable products and cyclic oligosaccharides and mixtures thereof, or they may be compositions at least one compound of formula (I). chemically bound to substrates which are adapted to release 0009. The present invention also relates to compositions the compounds of formula (I) upon application of an exog and consumable products, comprising at least one umami enous stimulus Such as light, enzymes, or the like. tastant, and at least one compound of formula (I). 0022. In another aspect of the present invention there is 0010. The present invention also relates to novel com provided the use of a compound of formula (I) as an umami pounds of formula (I). taste and savoury flavour enhancer. 0023. In a further aspect of the present invention there is 0011. The term “umami tastant, as used herein, refers to provided a composition comprising at least one umami any compound or ingredient able to elicite an umami taste, tastant and at least one compound of formula (I). non limiting examples of which are provided hereinbelow. 0024 Compositions according to the present invention 0012. The term “umami taste and savoury flavour comprise at least one umami tastant and at least one com enhancer, as used herein, refers to any compound or ingre pound of formula (I). Additionally the compositions may dient, that may or may not elicit an umami taste or savoury comprise other ingredients such as other known umami taste flavour itself, that when used in a composition comprising at or savoury flavour enhancers, and other flavourant ingredi least one umami tastant results in an increase in the overall entS. umami taste and savoury flavour perception. 0025. Examples of said umami tastants and/or said umami 0013 The present invention can be understood more taste or savoury flavour enhancers include, but are not limited readily by reference to the following detailed description and to: L-Glu (glutamic acid, glutamate, for example in the form to the examples included herein. of its salts such as monosodium glutamate, monopotassium 0014. In a first aspect of the present invention there is glutamate, monoammonium glutamate, calcium diglutamate, provided a method of enhancing the umami taste and savoury magnesium diglutamate), L-Asp (L-asparagine, or a salt US 2012/02311 40 A1 Sep. 13, 2012 thereof), 5'-ribonucleotides or their salts including, without 0033. In a more particular embodiment compositions of limitation, calcium 5'-ribonucleotides, disodium 5'-ribo the present invention contain at least one salt of glutamate, in nucleotides, and dipotassium 5'-ribonucleotides (e.g. inosinic particularly MSG, at least one compound of formula (I) and at acid, guanylic acid, adenosinic acid, inosinates, guanylates, least one purine nucleotide, in particularly inosine mono and adenylates, including guanosine 5'-monophosphate, phosphate (IMP) and guanosine monophosphate (GMP). inosine 5'-monophosphate, and 5'-adenylate and their salts 0034 Compounds of formula (I) may be used in compo Such as disodium guanylate, disodium inosinate, disodium sitions at a concentration of up to 99.9%, particularly 1.0- adenylate; dipotassium guanylate, dipotassium inosinate, 99%, and more particularly 5%-99%. dipotassium adenylate, calcium guanylate, calcium inosinate, 0035. In yet a further aspect of the present invention there calcium adenylate), maltol, ethyl maltol, glycine, L-leucine, is provided a method of enhancing or modifying the umami autolyzed or hydrolyzed proteins (e.g. autolyzed yeast, taste and savoury flavour of a consumable product, compris hydrolyzed yeast, hydrolyzed vegetable proteins), Koji-Aji (a ing at least one umami tastant, comprising the step of adding nucleotide-rich yeast extract, with fermented wheat gluten to the said consumable product a compound of formula (I). and maltodextrin also containing glutamates produced by 0036 Consumable products as used herein means any Ajinomoto Food Ingredients), and natural preparations or product that is intended to be placed in the mouth and extracts containing one or more of the above, for example ingested, or used in the mouth and then discarded. Suitable including extracts, purees or concentrates of vegetables (in consumable products include, but are not limited to, food cluding mushrooms, Shiitake, Soy, tomato, potato, whey, kelpf products, beverage products, nutraceutical products, and den seaweeds), cereals, meat, fish (e.g. shellfish, masago), milk, tal care products including mouth wash. cheese, and egg yolks, derived from the relevant ingredient in 0037. In yet another aspect of the present invention there is fresh or infermented, partially or fully hydrolyzed form (e.g. provided a consumable product comprising at least one various hydrolysed proteins). umami tastant and a compound of formula (I). 0026. Examples of said other flavourant ingredients 0038. In a particular embodiment the consumable product include, but are not limited to, natural flavours, artificial fla is a food or beverage product.
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