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Encyclopedia > Sweetness
Sweet foods, such as this strawberry shortcake, are often eaten for dessert.
Sweet foods, such as this strawberry shortcake, are often eaten for dessert.

Sweetness is one of the five basic tastes, and is almost universally regarded as a pleasurable experience. Foods rich in simple carbohydrates such as sugar are those most commonly associated with sweetness, although there are other natural and artificial compounds that are much sweeter, some of which have been used as sugar substitutes for those with a sweet tooth. Other compounds may alter perception of sweetness itself. Look up sweetness in Wiktionary, the free dictionary. ... Look up Sweet (disambiguation) in Wiktionary, the free dictionary. ... Image File history File links Strawberry_Shortcake. ... Image File history File links Strawberry_Shortcake. ... Not to be confused with Desert. ... Sour redirects here. ... Look up Pleasure in Wiktionary, the free dictionary. ... Lactose is a disaccharide found in milk. ... This article is about sugar as food and as an important and widely traded commodity. ... This article needs additional references or sources for verification. ...


The chemosensory basis for detecting sweetness, which varies among both individuals and species, has only been teased apart in recent years. The current theoretical model is the multipoint attachment theory, which involves multiple binding sites between sweetness receptor and the sweet substance itself. A chemosensor, also known as chemoreceptor, is a cell or group of cells that transduce a chemical signal into an action potential. ... The word theory has a number of distinct meanings in different fields of knowledge, depending on their methodologies and the context of discussion. ...

Contents

Examples of sweet substances

Further information: Sugar substitute
Sugar crystals.
Sugar crystals.

A great diversity of chemical compounds, such as aldehydes and ketones are sweet. Among common biological substances, all of the simple carbohydrates are sweet to at least some degree. Sucrose (table sugar) is the prototypical example of a sweet substance, although another sugar, fructose, is somewhat sweeter. Some of the amino acids are mildly sweet: alanine, glycine, and serine are the sweetest. Some other amino acids are perceived as both sweet and bitter. This article needs additional references or sources for verification. ... Image File history File linksMetadata Download high resolution version (3456x2304, 1476 KB) Summary The sugar was on a ruler, and the black marks are 1mm apart. ... Image File history File linksMetadata Download high resolution version (3456x2304, 1476 KB) Summary The sugar was on a ruler, and the black marks are 1mm apart. ... Look up chemical compound in Wiktionary, the free dictionary. ... An aldehyde is either a functional group consisting of a terminal carbonyl group, or a compound containing a terminal carbonyl group. ... A ketone is either the functional group characterized by a carbonyl group linked to two other carbon atoms or a compound that contains this functional group. ... Lactose is a disaccharide found in milk. ... Flash point N/A Except where noted otherwise, data are given for materials in their standard state (at 25 Â°C, 100 kPa) Infobox disclaimer and references Sucrose (common name: table sugar, also called saccharose) is a disaccharide (glucose + fructose) with the molecular formula C12H22O11. ... Fructose (or levulose) is a simple sugar (monosaccharide) found in many foods and is one of the three most important blood sugars along with glucose and galactose. ... This article is about the class of chemicals. ... Alanine (Ala, A) also 2-aminopropanoic acid is a non-essential α-amino acid. ... For the plant, see Glycine (plant). ... Serine (IPA ), organic compound, one of the 20 amino acids commonly found in animal proteins. ... Human taste sensory organs, called taste buds or gustatory calyculi, and concentrated on the upper surface of the tongue, appear to be receptive to relatively few chemical species as tastes. ...


A number of plant species produce glycosides that are many times sweeter than sugar. The most well-known example is glycyrrhizin, the sweet component of licorice root, which is about 30 times sweeter than sucrose. Another commercially important example is stevioside, from the South American shrub Stevia rebaudiana. It is roughly 250 times sweeter than sucrose. Another class of potent natural sweeteners are the sweet proteins such as thaumatin, found in the West African katemfe fruit. Hen egg lysozyme, an antibiotic protein found in chicken eggs, is also sweet. A glycoside is a molecule where a sugar group is bonded through its anomeric carbon to a nonsugar group by either an oxygen or a nitrogen atom. ... This article is about sugar as food and as an important and widely traded commodity. ... Glycyrrhizin, glycyrrhizinic acid or glycyrrhizic acid, is the active principle of liquorice root. ... Species Glycyrrhiza acanthocarpa Glycyrrhiza aspera Glycyrrhiza astragalina Glycyrrhiza bucharica Glycyrrhiza echinata Glycyrrhiza eurycarpa Glycyrrhiza foetida Glycyrrhiza glabra Glycyrrhiza iconica Glycyrrhiza korshinskyi Glycyrrhiza lepidota Glycyrrhiza pallidiflora Glycyrrhiza triphylla Glycyrrhiza uralensis Glycyrrhiza yunnanensis Ref: ILDIS Version 6. ... Stevioside is a glycoside derived from the stevia plant, which can be used as a sweetener. ... South America South America is a continent crossed by the equator, with most of its area in the Southern Hemisphere. ... Species About 150 species, including: Stevia eupatoria Stevia ovata Stevia plummerae Stevia rebaudiana Stevia salicifolia Stevia serrata Stevia is a genus of about 150 species of herbs and shrubs in the sunflower family (Asteraceae), native to subtropical and tropical South America and Central America. ... Thaumatin is a mixture of proteins isolated from the katemfe fruit (Thaumatococcus daniellii Bennett) of west Africa. ...  Western Africa (UN subregion)  Maghreb[1] West Africa or Western Africa is the westernmost region of the African continent. ... Lysozyme single crystal. ... Staphylococcus aureus - Antibiotics test plate. ... Alternate uses: Chicken (disambiguation) Binomial name Gallus gallus (Linnaeus, 1758) A chicken is a type of domesticated bird which is usually raised as a type of poultry. ...

Sweetness of various compounds[1][2]
Name Type of compound Sweetness
Lactose Disaccharide 0.16
Glucose Monosaccharide 0.75
Sucrose Disaccharide 1.00 (reference)
Fructose Monosaccharide 1.75
Sodium cyclamate Sulfonate 26
Aspartame Dipeptide methyl ester 250
Sodium saccharin Sulfonyl compound 510

Even some inorganic compounds are sweet, including beryllium chloride and lead acetate. The latter may have contributed to lead poisoning among the ancient Roman aristocracy: the Roman delicacy sapa was prepared by boiling soured wine (containing acetic acid) in lead pots. Lactose is a disaccharide that consists of β-D-galactose and β-D-glucose molecules bonded through a β1-4 glycosidic linkage. ... Sucrose, a common disaccharide A disaccharide is a sugar (a carbohydrate) composed of two monosaccharides. ... Glucose (Glc), a monosaccharide (or simple sugar), is an important carbohydrate in biology. ... Monosaccharides are the simplest form of carbohydrates. ... Flash point N/A Except where noted otherwise, data are given for materials in their standard state (at 25 Â°C, 100 kPa) Infobox disclaimer and references Sucrose (common name: table sugar, also called saccharose) is a disaccharide (glucose + fructose) with the molecular formula C12H22O11. ... Fructose (or levulose) is a simple sugar (monosaccharide) found in many foods and is one of the three most important blood sugars along with glucose and galactose. ... Cyclamate is an artificial sweetener that was discovered in 1937 at the University of Illinois by graduate student Michael Sveda. ... The structure of a typical sulfonate group. ... Except where noted otherwise, data are given for materials in their standard state (at 25 Â°C, 100 kPa) Infobox disclaimer and references Aspartame (or APM) (IPA: ) is the name for an artificial, non-saccharide sweetener, aspartyl-phenylalanine-1-methyl ester; i. ... Saccharin[2] is the oldest artificial sweetener. ... Sulfonyl is an organic radical (or functional group) obtained from an sulfonic acid by the removal of the hydroxyl group. ... Traditionally, inorganic compounds are considered to be of mineral, not biological, origin. ... Beryllium Chloride is a chemical compound of beryllium and chloride, with the chemical formula (BeCl2) Attempts to isolate the new element finally succeeded in 1828 when two chemists, Friedrich Wölhler of Germany and A. Bussy of France, independently produced beryllium by reducing beryllium chloride (BeCl2) with potassium in a... Lead acetate (Trihydrate Pb(CH3COO)2·3H2O) is a white crystalline substance made by dissolving lead in acetic acid. ... Lead poisoning is a medical condition, also known as saturnism, plumbism or painters colic, caused by increased blood lead levels. ... Ancient Rome was a civilization that grew from a small agricultural community founded on the Italian Peninsula circa the 9th century BC to a massive empire straddling the Mediterranean Sea. ... For other uses, see Wine (disambiguation). ... R-phrases , S-phrases , , , Flash point 43 °C Related Compounds Related carboxylic; acids Formic acid; Propionic acid; Butyric acid Related compounds acetamide; ethyl acetate; acetyl chloride; acetic anhydride; acetonitrile; acetaldehyde; ethanol; thioacetic acid; acetylcholine; acetylcholinesterase Supplementary data page Structure and properties n, εr, etc. ...


Hundreds of synthetic organic compounds are known to be sweet. The number of these that are legally permitted as food additives is, however, much smaller. For example, chloroform, nitrobenzene, and Ethylene glycol are sweet, but also toxic. As of 2005, seven artificial sweeteners are in widespread use: saccharin, cyclamate, aspartame, acesulfame potassium, sucralose, alitame, and neotame. Cyclamate was banned for a short period in the US, and a similar situation occurred in Canada with saccharin.[1] R-phrases , , , S-phrases , Flash point Non-flammable U.S. Permissible exposure limit (PEL) 50 ppm (240 mg/m3) (OSHA) Supplementary data page Structure and properties n, εr, etc. ... Nitrobenzene, also known as nitrobenzol or oil of mirbane, is a poisonous organic compound with an almond odor and chemical formula C6H5NO2. ... Ethylene glycol (monoethylene glycol (MEG), IUPAC name: ethane-1,2-diol) is an alcohol with two -OH groups (a diol), a chemical compound widely used as an automotive antifreeze. ... 2005 is a common year starting on Saturday of the Gregorian calendar. ... Saccharin[2] is the oldest artificial sweetener. ... Cyclamate is an artificial sweetener that was discovered in 1937 at the University of Illinois by graduate student Michael Sveda. ... Except where noted otherwise, data are given for materials in their standard state (at 25 Â°C, 100 kPa) Infobox disclaimer and references Aspartame (or APM) (IPA: ) is the name for an artificial, non-saccharide sweetener, aspartyl-phenylalanine-1-methyl ester; i. ... Chemical structure of Acesulfame potassium Acesulfame potassium is a calorie-free artificial sweetener, also known as Acesulfame K or Ace K, and marketed under the trade names Sunett and Sweet One. ... Sucralose is an artificial sweetener. ... Alitame is an artifical sweetener developed by Pfizer in the early 1980s and currently marketed in some countries under the brand name Aclame. ... Chemical structure of neotame. ...


Sweetness modifiers

The Miracle fruit, origin of Miraculin
The Miracle fruit, origin of Miraculin

A few substances alter the way sweet taste is perceived. One class of these inhibits the perception of sweet tastes, whether from sugars or from highly potent sweeteners. Commercially, the most important of these is lactisole[3], a compound produced by Domino Sugar. It is used in some jellies and other fruit preserves to bring out their fruit flavors by suppressing their otherwise strong sweetness. Portrait File history Legend: (cur) = this is the current file, (del) = delete this old version, (rev) = revert to this old version. ... Portrait File history Legend: (cur) = this is the current file, (del) = delete this old version, (rev) = revert to this old version. ... Binomial name A.DC. The Miracle Fruit Plant, sometimes known as Miraculous Berry, or Magic Berry (Sideroxylon dulcificum/Synsepalum dulcificum) is a plant first documented by an explorer named Des Marchais during a 1725 excursion to its native West Africa. ... Lactisole is a flavor modifier manufactured and sold by Domino Sugar. ... Domino Foods, Inc. ... Jam from berries Fruit preserves refers to fruit, or vegetables, that have been prepared and canned for long term storage. ...


Two natural products have been documented to have similar sweetness-inhibiting properties: gymnemic acid, extracted from the leaves of the Indian vine Gymnema sylvestre and ziziphin, from the leaves of the Chinese jujube (Ziziphus jujuba).[4] Gymnemic acid has been widely promoted within herbal medicine as a treatment for sugar cravings and diabetes mellitus. Gymnemic acids are glycosides isolated from the leaves of Gymnema sylvestre (Asclepiadaceae). ... Gymnema Sylvestre (latin for destroyer of sugar) is a herb known for helping people overcome sugar cravings by blocking the taste receptors from tasting the sugar. ... Ziziphin, a triterpene glycoside which exhibits taste-modifying property, has been isolated from the leaves of Ziziphus jujuba (Rhamnaceae). ... Binomial name (L.) H. Karst. ... The term Herbalism refers to folk and traditional medicinal practice based on the use of plants and plant extracts. ... For the disease characterized by excretion of large amounts of very dilute urine, see diabetes insipidus. ...


On the other hand, two plant proteins, miraculin[5] and curculin[6], cause sour foods to taste sweet. Once the tongue has been exposed to either of these proteins, sourness is perceived as sweetness for up to an hour afterwards. While curculin has some innate sweet taste of its own, miraculin is by itself quite tasteless. The Miracle Fruit, origin of Miraculin Miraculin is a glycoprotein extracted from the miracle fruit plant, a shrub native to West Africa (Synsepalum dulcificum or Richadella dulcifica). ... Curculin Curculin which is extracted from Curculigo latifolia acts as a good low calorie sweetener. ... Human taste sensory organs, called taste buds or gustatory calyculi, are concentrated on the upper surface of the tongue. ...


The sweetness receptor

Sweetness is perceived by the taste buds.
Sweetness is perceived by the taste buds.

Despite the wide variety of chemical substances known to be sweet, and knowledge that the ability to perceive sweet taste must reside in taste buds on the tongue, the biomolecular mechanism of sweet taste was sufficiently elusive that as recently as the 1990s, there was some doubt whether any single "sweetness receptor" actually exists. Image File history File links Gray1018. ... Image File history File links Gray1018. ... Taste buds are small structures on the upper surface of the tongue, soft palate, and epiglottis that provide information about the taste of food being eaten. ... For other uses, see Tongue (disambiguation). ...


The breakthrough for the present understanding of sweetness occurred in 2001, when experiments with laboratory mice showed that mice possessing different versions of the gene T1R3 prefer sweet foods to different extents. Subsequent research has shown that the T1R3 protein forms a complex with a related protein, called T1R2, to form a G-protein coupled receptor that is the sweetness receptor in mammals.[7] ... For other uses, see Gene (disambiguation). ... In cell biology, G-protein-coupled receptors, also known as GPCR, seven transmembrane receptors, heptahelical receptors, or 7TM receptors, are a class of transmembrane receptors. ...


Sweetness perception may differ between species significantly, for example even amongst the primates sweetness is quite variable. New World monkeys do not find aspartame sweet, while Old World monkeys, apes and humans all do.[8] Families 15, See classification A primate is any member of the biological order Primates, the group that contains all the species commonly related to the lemurs, monkeys, and apes, with the latter category including humans. ... Families Cebidae Aotidae Pitheciidae Atelidae The New World monkeys are the four families of primates that are found in Central and South America: the Cebidae, Aotidae, Pitheciidae and Atelidae. ... Subfamilies Cercopithecinae - 11 genera Colobinae - 10 genera The Old World monkeys or Cercopithecidae are a group of primates, falling in the superfamily Cercopithecoidea in the clade Catarrhini. ... This article is about the biological superfamily. ...


Historical theories of sweetness

Lugduname is the sweetest chemical known.
Lugduname is the sweetest chemical known.

The development of organic chemistry in the 19th century introduced many new chemical compounds and the means to determine their molecular structures. Early organic chemists tasted many of their products, either intentionally (as a means of characterization) or accidentally (due to poor laboratory hygiene). One of the first attempts to draw systematic correlations between molecules' structures and their tastes was made by a German chemist, Georg Cohn, in 1914. He advanced the hypothesis that in order to evoke a certain taste, a molecule must contain some structural motif (called a sapophore) that produced that taste. With regard to sweetness, he noted that molecules containing multiple hydroxyl groups and those containing chlorine atoms are often sweet, and that among a series of structurally similar compounds, those with smaller molecular weights were often sweeter than the larger compounds. Image File history File links No higher resolution available. ... Image File history File links No higher resolution available. ... Organic chemistry is a specific discipline within chemistry which involves the scientific study of the structure, properties, composition, reactions, and preparation (by synthesis or by other means) of chemical compounds consisting primarily of carbon and hydrogen, which may contain any number of other elements, including nitrogen, oxygen, halogens as well... Geometry of the water molecule Molecules have fixed equilibrium geometries--bond lengths and angles--that are dictated by the laws of quantum mechanics. ... Hygiene refers to practices associated with ensuring good health and cleanliness. ... // Hydroxyl group The term hydroxyl group is used to describe the functional group -OH when it is a substituent in an organic compound. ... General Name, symbol, number chlorine, Cl, 17 Chemical series halogens Group, period, block 17, 3, p Appearance yellowish green Standard atomic weight 35. ... The molecular mass of a substance (less accurately called molecular weight and abbreviated as MW) is the mass of one molecule of that substance, relative to the unified atomic mass unit u (equal to 1/12 the mass of one atom of carbon-12). ...


In 1919, Oertly and Myers proposed a more elaborate theory based on a then-current theory of color in synthetic dyes. They hypothesized that in order to be sweet, a compound must contain one each of two classes of structural motif, a glucophore and an auxogluc. Based on those compounds known to be sweet at the time, they proposed a list of six candidate glucophores and nine auxoglucs. Color is an important part of the visual arts. ... Look up dye in Wiktionary, the free dictionary. ...


From these beginnings in the early 20th century, the theory of sweetness enjoyed little further academic attention until 1963, when Robert Shallenberger and Terry Acree proposed the AH-B theory of sweetness. Simply put, they proposed that in order to be sweet, a compound must contain a hydrogen bond donor (AH) and a Lewis base (B) separated by about 0.3 nanometres. According to this theory, the AH-B unit of a sweetener binds with a corresponding AH-B unit on the biological sweetness receptor to produce the sensation of sweetness. An example of a quadruple hydrogen bond between a self-assembled dimer complex reported by Meijer and coworkers. ... An electron donor is a compound that gives up or donates an electron during cellular respiration, resulting in the release of energy. ... A Lewis base is any molecule or ion that can form a new covalent bond by donating a pair of electrons. ... A nanometre (American spelling: nanometer, symbol nm) (Greek: νάνος, nanos, dwarf; μετρώ, metrό, count) is a unit of length in the metric system, equal to one billionth of a metre (or one millionth of a millimetre), which is the current SI base unit of length. ...


A later refinement of this theory was the AH-B-X theory proposed by Lemont Kier in 1972. While previous researchers had noted that among some groups of compounds, there seemed to be a correlation between hydrophobicity and sweetness, this theory formalized these observations by proposing that in order to be sweet, a compound must have a third binding site (labeled X) that could interact with a hydrophobic site on the sweetness receptor via London dispersion forces. Later researchers have statistically analyzed the distances between the presumed AH, B, and X sites in several families of sweet substances to estimate the distances between these interaction sites on the sweetness receptor. In chemistry, hydrophobic or lipophilic species, or hydrophobes, tend to be electrically neutral and nonpolar, and thus prefer other neutral and nonpolar solvents or molecular environments. ... The title given to this article is incorrect due to technical limitations. ...


The most elaborate theory of sweetness to date is the multipoint attachment theory (MPA) proposed by Jean-Marie Tinti and Claude Nofre in 1991. This theory involves a total of eight interaction sites between a sweetener and the sweetness receptor, although not all sweeteners interact with all eight sites.[citation needed] This model has successfully directed efforts aimed at finding highly potent sweeteners, including the most potent family of sweeteners known to date, the guanidine sweeteners. The most potent of these, lugduname, is about 225,000 times sweeter than sucrose. Guanidine is a crystalline compound of strong alkalinity formed by the oxidation of guanine. ... Currently, Lugduname is the most potent sweetening agent known for humans. ...


References

Cited

  1. ^ a b John McMurry (1998). Organic Chemistry, 4th edition, Brooks/Cole, 468. 
  2. ^ Susan S. Schiffman (2000) "Synergism among Ternary Mixtures of Fourteen Sweeteners" in Chemical Senses Volume 25 (2), pages 131-140. Entrez PubMed ISSN [http://dispatch.opac.ddb.de/DB=1.1/LNG=EN/CMD?ACT=SRCHA&IKT=8&TRM=1464-3553 1464-3553 ISSN 1464-3553]. Retrieved on 2007-09-02
  3. ^ Kinghorn, A.D. and Compadre, C.M. Alernative Sweeteners: Third Edition, Revised and Expanded, Marcel Dekker ed., New York, 2001. ISBN 0-8247-0437-1
  4. ^ Kurihara, Y. 1992. Characteristics of antisweet substances, sweet proteins, and sweetness-inducing proteins. Crit. Rev. Food Sci. Nutr. 32:231-252.
  5. ^ K Kurihara and LM Beidler. Taste-Modifying Protein from Miracle Fruit. Sience 1968, Vol. 161. no. 3847, pp. 1241-1243.
  6. ^ Yamashita, H., T. Akabane, and Y. Kurihara. 1995. Activity and stability of a new sweet protein with taste-modifying action, curculin. Chem. Senses 20:239-243.
  7. ^ Li X, Staszewski L, Xu H, Durick K, Zoller M et al. (2002) Human receptors for sweet and umami taste. Proc Natl Acad Sci USA 99, 4692–4696 http://www.pnas.org/cgi/content/abstract/99/7/4692
  8. ^ Nofre, C., J. M. Tinti and D. Glaser (1995) Evolution of the Sweetness Receptor in Primates. I. Why Does Alitame Taste Sweet in all Prosimians and Simians, and Aspartame only in Old World Simians? Chemical Senses 20: 573-584.

The Entrez logo The Entrez Global Query Cross-Database Search System allows access to databases at the National Center for Biotechnology Information (NCBI) website. ... ISSN, or International Standard Serial Number, is the unique eight-digit number applied to a periodical publication including electronic serials. ... Year 2007 (MMVII) is the current year, a common year starting on Monday of the Gregorian calendar and the AD/CE era in the 21st century. ... is the 245th day of the year (246th in leap years) in the Gregorian calendar. ...

General

  • Cohn, Georg (1914). Die Organischen Geschmackstoffe. Berlin: F. Siemenroth.
  • Kier L (1972). "". Journal of Pharmaceutical Science 61: 1394. 
  • Kitagawa M, Kusakabe Y, Miura H, Ninomiya Y, Hino A (2001). "Molecular genetic identification of a candidate receptor gene for sweet taste". Biochemical and Biophysical Research Communications 283: 236–242. 
  • Li XD, Staszewski L, Xu H, Durick K, Zoller M, Adler E (2002). "Human receptors for sweet and umami taste". Proceedings of the National Academy of Sciences of the United States of America 99: 4692–4696. 
  • Max M, Shanker YG, Huang LQ, Rong M, Liu Z, Campagne F, Weinstein H, Damak S, Margolskee RF (2001). "Tas1r3, encoding a new candidate taste receptor, is allelic to the sweet responsiveness locus Sac". Nature Genetics 28: 58–63. 
  • Montmayeur JP, Liberles SD, Matsunami H, Buck LB (2001). "A candidate taste receptor gene near a sweet taste locus". Nature Neuroscience 4: 492–498. 
  • Nelson G, Hoon MA, Chandrashekar J, Zhang YF, Ryba NJP, Zuker CS (2001). "Mammalian sweet taste receptors". Cell 106: 381–390. 
  • Nofre C, Tinti JM (1996). "Sweetness reception in man: the multipoint attachment theory". Food Chemistry 56: 263–274. 
  • Sainz E, Korley JN, Battey JF, Sullivan SL (2001). "Identification of a novel member of the T1R family of putative taste receptors". Journal of Neurochemistry 77: 896–903. 
  • Shallenberger RS (1963). "Hydrogen bonding and the varying sweetness of the sugars". Journal of Food Science 28: 584–589. 
  • Tinti, Jean-Marie & Nofre, Claude (1991). Why does a sweetener taste sweet? A new model. In D.E. Walters, F.T Orthoefer & G.E. DuBois (Eds.), Sweeteners: Discovery, Molecular Design, and Chemoreception, ACS Symposium Series 450, pp. 209–213. Washington, DC: American Chemical Society.

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