Lactose

From Wikipedia, the free encyclopedia

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Lactose
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Names
IUPAC names
β-Page Template:Smallcaps/styles.css has no content.d-Galactopyranosyl-(1→4)-α-Page Template:Smallcaps/styles.css has no content.d-glucopyranose
4-O-β-Page Template:Smallcaps/styles.css has no content.d-Galactopyranosyl-α-Page Template:Smallcaps/styles.css has no content.d-glucopyranose
Systematic IUPAC name
(2R,3R,4S,5R,6S)-2-(Hydroxymethyl)-6-{[(2R,3S,4R,5R,6R)-4,5,6-trihydroxy-2-(hydroxymethyl)oxan-3-yl]oxy}oxane-3,4,5-triol
Other names
Milk sugar
Lactobiose
4-O-β-D-Galactopyranosyl-D-glucose
Identifiers
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3D model (JSmol)
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90841
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EC Number Page Template:Plainlist/styles.css has no content.
342369
KEGG Page Template:Plainlist/styles.css has no content.
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  • InChI=1S/C12H22O11/c13-1-3-5(15)6(16)9(19)12(22-3)23-10-4(2-14)21-11(20)8(18)7(10)17/h3-20H,1-2H2/t3-,4-,5+,6+,7-,8-,9-,10-,11-,12+/m1/s1 checkY
    Key: GUBGYTABKSRVRQ-DCSYEGIMSA-N checkY
  • InChI=1/C12H22O11/c13-1-3-5(15)6(16)9(19)12(22-3)23-10-4(2-14)21-11(20)8(18)7(10)17/h3-20H,1-2H2/t3-,4-,5+,6+,7-,8-,9-,10-,11-,12+/m1/s1
    Key: GUBGYTABKSRVRQ-DCSYEGIMBP
  • C([C@@H]1[C@@H]([C@@H]([C@H]([C@@H](O1)O[C@@H]2[C@H](O[C@H]([C@@H]([C@H]2O)O)O)CO)O)O)O)O
Properties
C12H22O11
Molar mass 342.297 g·mol−1
Appearance White solid
Density 1.525 g/cm3
Melting point 252 °C (anhydrous)[1]
202 °C (monohydrate)[1]
195 g/L[2][3]
+55.4° (anhydrous)
+52.3° (monohydrate)
Thermochemistry
5652 kJ/mol, 1351 kcal/mol, 16.5 kJ/g, 3.94 kcal/g
Hazards
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NFPA 704 four-colored diamondHealth 0: Exposure under fire conditions would offer no hazard beyond that of ordinary combustible material. E.g. sodium chlorideFlammability 0: Will not burn. E.g. waterInstability 0: Normally stable, even under fire exposure conditions, and is not reactive with water. E.g. liquid nitrogenSpecial hazards (white): no code
0
0
0
Flash point 357.8 °C (676.0 °F; 631.0 K)[4]
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
☒N verify (what is checkY☒N ?)

Template:Chembox Footer/trackingTemplate:Short description

Lactose is a disaccharide composed of galactose and glucose and has the molecular formula C12H22O11. Lactose makes up around 2–8% of milk (by mass). The name comes from Template:Wikt-lang (gen. Template:Wikt-lang), the Latin word for milk, plus the suffix -ose used to name sugars. The compound is a white, water-soluble, non-hygroscopic solid with a mildly sweet taste. It is used in the food industry.[5]

Structure and reactions

File:Alpha-lactose-from-xtal-3D-balls.png
The molecular structure of α-lactose, as determined by X-ray crystallography.

Lactose is a disaccharide composed of galactose and glucose, which form a β-1→4 glycosidic linkage. Its systematic name is β-D-galactopyranosyl-(1→4)-D-glucose. The glucose can be in either the α-pyranose form or the β-pyranose form, whereas the galactose can have only the β-pyranose form: hence α-lactose and β-lactose refer to the anomeric form of the glucopyranose ring alone. Detection reactions for lactose are the Wöhlk[6] and Fearon tests.[7] They can be used to detect the different lactose content of dairy products such as whole milk, lactose free milk, yogurt, buttermilk, coffee creamer, sour cream, kefir, etc.[8]

Lactose is hydrolysed to glucose and galactose, isomerised in alkaline solution to lactulose, and catalytically hydrogenated to the corresponding polyhydric alcohol, lactitol.[9] Lactulose is a commercial product, used for treatment of constipation.[10]

Occurrence and isolation

Lactose appears in the milk of many different mammal species, though not all. Rhesus macaque monkeys have a concentration of lactose of 8%. Many mammals, like bears, produce milk with no lactose.[11] Bovine milk has a concentration of around 4.8%.[12]

Whey or milk plasma is the liquid remaining after milk is curdled and strained, for example in the production of cheese. Whey is made up of 6.5% solids, of which 4.8% is lactose, which is purified by crystallisation.[13] Industrially, lactose is produced from whey permeate – whey filtrated for all major proteins. The protein fraction is used in infant nutrition and sports nutrition while the permeate can be evaporated to 60–65% solids and crystallized while cooling.[14] Lactose can also be isolated by dilution of whey with ethanol.[15]

Metabolism

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Infant mammals nurse on their mothers to drink milk, which is rich in lactose. The intestinal villi secrete the enzyme lactase (β-D-galactosidase) to digest it. This enzyme cleaves the lactose molecule into its two subunits, the simple sugars glucose and galactose, which can be absorbed. Since lactose occurs mostly in milk, in most mammals, the production of lactase gradually decreases with maturity due to weaning; the removal of lactose from the diet removes the metabolic pressure to continue to produce lactase for its digestion.[16][17]

Many people with ancestry in Europe, West Asia, South Asia, the Sahel belt in West Africa, East Africa and a few other parts of Central Africa maintain lactase production into adulthood due to selection for genes that continue lactase production. In many of these areas, milk from mammals such as cattle, goats, and sheep is used as a large source of food. It was in these regions that genes for lifelong lactase production first evolved.[18] The genes of adult lactose tolerance have evolved independently in various ethnic groups.[19][page needed] By descent, more than 70% of western Europeans can digest lactose as adults, compared with less than 30% of people from areas of Africa, eastern and south-eastern Asia and Oceania.[20] In people who are lactose intolerant, lactose is not broken down and provides food for gas-producing gut flora, which can lead to diarrhea, bloating, flatulence, and other gastrointestinal symptoms.

Biological properties

The sweetness of lactose is 0.2 to 0.4, relative to 1.0 for sucrose.[21] For comparison, the sweetness of glucose is 0.6 to 0.7, of fructose is 1.3, of galactose is 0.5 to 0.7, of maltose is 0.4 to 0.5, of sorbose is 0.4, and of xylose is 0.6 to 0.7.[21]

When lactose is completely digested in the small intestine, its caloric value is 4 kcal/g, or the same as that of other carbohydrates.[21] However, lactose is not always fully digested in the small intestine. Depending on ingested dose, combination with meals (either solid or liquid), and lactase activity in the intestines, the caloric value of lactose ranges from 2 to 4 kcal/g.[21] Undigested lactose acts as dietary fiber. It also has positive effects on absorption of minerals, such as calcium and magnesium.[21]

The glycemic index of lactose is 46 to 65.[22] For comparison, the glycemic index of glucose is 100 to 138, of sucrose is 68 to 92, of maltose is 105, and of fructose is 19 to 27.[21][22]

Lactose has relatively low cariogenicity among sugars.[23] This is because it is not a substrate for dental plaque formation and it is not rapidly fermented by oral bacteria.[23] The buffering capacity of milk also reduces the cariogenicity of lactose.[21]

Applications

Its mild flavor and easy handling properties have led to its use as a carrier and stabiliser of aromas and pharmaceutical products.[5] Lactose is not commonly added directly to food, because its low solubility can lead to a gritty mouthfeel.[24] Infant formula is a notable exception, where lactose is added to match the composition of human milk.[25] However, lactose-reduced formulas are increasing in popularity.[26]

One of the undesirable properties of lactose utilization is its low solubility, which can result in crystallization, giving a gritty and sandy mouthfeel in the final product. Usually, in supersaturated solution, sugars tend to crystallize, also forming big agglomerates, depending on the process condition.

Lactose is not fermented by most yeast during brewing, which may be used to advantage.[9] For example, lactose may be used to sweeten stout beer; the resulting beer is usually called a milk stout or a cream stout.

Yeast belonging to the genus Kluyveromyces have a unique industrial application, as they are capable of fermenting lactose for ethanol production. Surplus lactose from the whey by-product of dairy operations is a potential source of alternative energy.[27]

Another significant lactose use is in the pharmaceutical industry. Lactose is added to tablet and capsule drug products as an ingredient because of its physical and functional properties (examples are atorvastatin, levocetirizine or thiamazole among many others).[5][28] For similar reasons, it can be used to dilute illicit drugs such as cocaine or heroin.[29]

History

The first crude isolation of lactose, by Italian physician Fabrizio Bartoletti (1576–1630), was published in 1633.[30] In 1700, the Venetian pharmacist Lodovico Testi (1640–1707) published a booklet of testimonials to the power of milk sugar (Script error: No such module "Lang".) to relieve, among other ailments, the symptoms of arthritis.[31] In 1715, Testi's procedure for making milk sugar was published by Antonio Vallisneri.[32] Lactose was identified as a sugar in 1780 by Carl Wilhelm Scheele.[33][9]

In 1812, Heinrich Vogel (1778–1867) recognized that glucose was a product of hydrolyzing lactose.[34] In 1856, Louis Pasteur crystallized the other component of lactose, galactose.[35] By 1894, Emil Fischer had established the configurations of the component sugars.[36]

Lactose was named by the French chemist Jean Baptiste André Dumas (1800–1884) in 1843.[37] In 1856, Pasteur named galactose "lactose".[38] In 1860, Marcellin Berthelot renamed it "galactose", and transferred the name "lactose" to what is now called lactose.[39] It has a formula of Page Module:Chem2/styles.css has no content.C12H22O11 and the hydrate formula Page Module:Chem2/styles.css has no content.C12H22O11·H2O, making it an isomer of sucrose.

See also

References

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  1. ^ a b Page Module:Citation/CS1/styles.css has no content.Peter M. Collins (2006). Dictionary of Carbohydrates (2nd ed.). Boca Raton: Chapman & Hall/CRC. p. 677. ISBN 978-0-8493-3829-8.
  2. ^ Page Module:Citation/CS1/styles.css has no content."D-Lactose".
  3. ^ The solubility of lactose in water is 189.049 g at 25 °C, 251.484 g at 40 °C and 372.149 g at 60 °C per kg solution. Its solubility in ethanol is 0.111 g at 40 °C and 0.270 g at 60 °C per kg solution.Page Module:Citation/CS1/styles.css has no content.Machado, José J. B.; Coutinho, João A.; Macedo, Eugénia A. (2001), "Solid–liquid equilibrium of α-lactose in ethanol/water", Fluid Phase Equilibria, 173 (1): 121–34, doi:10.1016/S0378-3812(00)00388-5, archived from the original (PDF) on 2020-08-06, retrieved 2007-07-04. ds
  4. ^ Sigma Aldrich
  5. ^ a b c Page Module:Citation/CS1/styles.css has no content.Gerrit M. Westhoff; Ben F.M. Kuster; Michiel C. Heslinga; Hendrik Pluim; Marinus Verhage (2014). "Lactose and Derivatives". Ullmann's Encyclopedia of Industrial Chemistry. Wiley-VCH. pp. 1–9. doi:10.1002/14356007.a15_107.pub2. ISBN 978-3-527-30673-2.
  6. ^ Page Module:Citation/CS1/styles.css has no content.Ruppersberg, Klaus; Blankenburg, Janet (2018). "150 Years Alfred Wöhlk". ChemViews. doi:10.1002/chemv.201800002.
  7. ^ Page Module:Citation/CS1/styles.css has no content.Fearon, W. R. (1942). "The detection of lactose and maltose by means of methylamine". The Analyst. 67 (793): 130. Bibcode:1942Ana....67..130F. doi:10.1039/an9426700130. ISSN 0003-2654.
  8. ^ Page Module:Citation/CS1/styles.css has no content.Ruppersberg, Klaus; Herzog, Stefanie; Kussler, Manfred W.; Parchmann, Ilka (2019-10-17). "How to visualize the different lactose content of dairy products by Fearon's test and Woehlk test in classroom experiments and a new approach to the mechanisms and formulae of the mysterious red dyes". Chemistry Teacher International. 2 (2). doi:10.1515/cti-2019-0008. ISSN 2569-3263. S2CID 208714341.
  9. ^ a b c Page Module:Citation/CS1/styles.css has no content.Linko, P (1982), "Lactose and Lactitol", in Birch, G.G.; Parker, K.J (eds.), Natural Sweeteners, London & New Jersey: Applied Science Publishers, pp. 109–132, ISBN 978-0-85334-997-6
  10. ^ Page Module:Citation/CS1/styles.css has no content.Hawrelak, Jason A. (2020-01-01), Pizzorno, Joseph E.; Murray, Michael T. (eds.), "104 - Prebiotics, Synbiotics, and Colonic Foods", Textbook of Natural Medicine (Fifth Edition), St. Louis (MO): Churchill Livingstone, pp. 797–808.e4, doi:10.1016/b978-0-323-43044-9.00104-7, ISBN 978-0-323-52342-4, retrieved 2025-02-15{{citation}}: CS1 maint: work parameter with ISBN (link)
  11. ^ Page Module:Citation/CS1/styles.css has no content.Newmark, Lauren (2017). "Milk Lactose From A to Zebra". International Milk Genomics Consortium. Retrieved March 10, 2026.
  12. ^ Page Module:Citation/CS1/styles.css has no content.Program, Human Foods (2024-09-05). "Raw Milk Misconceptions and the Danger of Raw Milk Consumption". FDA.
  13. ^ Page Module:Citation/CS1/styles.css has no content.Ranken, M. D.; Kill, R. C. (1997), Food industries manual, Springer, p. 125, ISBN 978-0-7514-0404-3
  14. ^ Page Module:Citation/CS1/styles.css has no content.Wong, S. Y.; Hartel, R. W. (2014), "Crystallization in lactose refining-a review", Journal of Food Science, 79 (3): R257–72, doi:10.1111/1750-3841.12349, PMID 24517206, DOI is open access
  15. ^ Page Module:Citation/CS1/styles.css has no content.Pavia, Donald L.; Lampman, Gary M.; Kriz, George S. (1990), Introduction to Organic Laboratory Techniques: A Microscale Approach, Saunders, ISBN 0-03-014813-8
  16. ^ Page Module:Citation/CS1/styles.css has no content.Balaresque, P.; King, T. E. (2010). "Nine - Human Phenotypic Diversity: An Evolutionary Perspective". In Orgogozo, Virginie (ed.). Current Topics in Developmental Biology. Genes and Evolution. Vol. 119. Academic Press. pp. 349–390. ISBN 9780124171947. Retrieved 2025-02-15.
  17. ^ Page Module:Citation/CS1/styles.css has no content.Gerbault, Pascale; Liebert, Anke; Itan, Yuval; Powell, Adam; Currat, Mathias; Burger, Joachim; Swallow, Dallas M.; Thomas, Mark G. (2011-03-27). "Evolution of lactase persistence: an example of human niche construction". Philosophical Transactions of the Royal Society B: Biological Sciences. 366 (1566): 863–877. doi:10.1098/rstb.2010.0268. ISSN 0962-8436. PMC 3048992. PMID 21320900.
  18. ^ Page Module:Citation/CS1/styles.css has no content.Itan, Yuval; Powell, Adam; Beaumont, Mark A.; Burger, Joachim; Thomas, Mark G. (2009-08-28). Tanaka, Mark M. (ed.). "The Origins of Lactase Persistence in Europe". PLOS Computational Biology. 5 (8) e1000491. Bibcode:2009PLSCB...5E0491I. doi:10.1371/journal.pcbi.1000491. ISSN 1553-7358. PMC 2722739. PMID 19714206.
  19. ^ Page Module:Citation/CS1/styles.css has no content.Wade, Nicholas (2006-12-10), "Study Detects Recent Instance of Human Evolution", New York Times
  20. ^ Page Module:Citation/CS1/styles.css has no content.Ridley, Matt (1999), Genome, HarperCollins, p. 193, ISBN 978-0-06-089408-5.
  21. ^ a b c d e f g Page Module:Citation/CS1/styles.css has no content.Schaafsma, Gertjan (2008). "Lactose and lactose derivatives as bioactive ingredients in human nutrition" (PDF). International Dairy Journal. 18 (5): 458–465. doi:10.1016/j.idairyj.2007.11.013. ISSN 0958-6946. S2CID 10346203. Archived from the original (PDF) on Mar 2, 2019.
  22. ^ a b Page Module:Citation/CS1/styles.css has no content.Björck, Inger; Liljeberg, Helena; Östman, Elin (2000). "Low glycaemic-index foods". British Journal of Nutrition. 83 (S1): S149–S155. doi:10.1017/S0007114500001094. ISSN 0007-1145. PMID 10889806. S2CID 14574754.
  23. ^ a b Page Module:Citation/CS1/styles.css has no content.Gregory D. Miller; Judith K. Jarvis; Lois D. McBean (15 December 2006). Handbook of Dairy Foods and Nutrition. CRC Press. pp. 248–. ISBN 978-1-4200-0431-1.
  24. ^ Page Module:Citation/CS1/styles.css has no content.Dominici, Simona; Marescotti, Francesca; Sanmartin, Chiara; Macaluso, Monica; Taglieri, Isabella; Venturi, Francesca; Zinnai, Angela; Facioni, Maria Sole (2022-05-19). "Lactose: Characteristics, Food and Drug-Related Applications, and Its Possible Substitutions in Meeting the Needs of People with Lactose Intolerance". Foods. 11 (10): 1486. doi:10.3390/foods11101486. ISSN 2304-8158. PMC 9141425. PMID 35627056.
  25. ^ Page Module:Citation/CS1/styles.css has no content.Slupsky, Carolyn M.; He, Xuan; Hernell, Olle; Andersson, Yvonne; Rudolph, Colin; Lönnerdal, Bo; West, Christina E. (2017-06-16). "Postprandial metabolic response of breast-fed infants and infants fed lactose-free vs regular infant formula: A randomized controlled trial". Scientific Reports. 7 (1): 3640. Bibcode:2017NatSR...7.3640S. doi:10.1038/s41598-017-03975-4. ISSN 2045-2322. PMC 5473881. PMID 28623320.
  26. ^ Page Module:Citation/CS1/styles.css has no content.DiMaggio, Dina M.; Abersone, Ilze; Porto, Anthony F. (2024). "Infant consumption of 100% lactose-based and reduced lactose infant formula in the United States: Review of NHANES data from 1999 to 2020". Journal of Pediatric Gastroenterology and Nutrition. 79 (5): 1017–1023. doi:10.1002/jpn3.12292. ISSN 1536-4801. PMID 38934419.
  27. ^ Page Module:Citation/CS1/styles.css has no content.Ling, Charles (2008), Whey to Ethanol: A Biofuel Role for Dairy Cooperatives? (PDF), United States Department of Agriculture Rural Development, archived from the original (PDF) on February 24, 2015.
  28. ^ Page Module:Citation/CS1/styles.css has no content.Zdrojewicz, Z.; Zyskowska, K.; Wasiuk, S. (2018). "Lactose in drugs and lactose intolerance – realities and myths". Paediatrics and Family Medicine. 14 (3): 261–266. doi:10.15557/PiMR.2018.0027.
  29. ^ Page Module:Citation/CS1/styles.css has no content.Rinaldi, R.; Negro, F.; Minutillo, A. (2020-02-20). "The health threat of new synthetic opioids as adulterants of classic drugs of abuse" (PDF). La Clinica Terapeutica. 171 (2): 107–109. doi:10.7417/CT.2020.2198. ISSN 1972-6007. PMID 32141480.
  30. ^ Fabrizio Bartoletti, Script error: No such module "Lang". ... [Procedure for asthma ... ], (Bologna ("Bononia"), (Italy): Nicolò Tebaldini for the heirs of Evangelista Dozza, 1633), p. 400. From page 400: "Script error: No such module "Lang". Script error: No such module "Lang".." (This is the manna of whey. [Note: "Manna" was the dried, sweet sap of the tree Fraxinus ornus.] Gently distill whey via a heat bath until the buttery scum settles to the bottom of the vessel, to which substance some whitish salt [i.e., precipitate] attaches. This curious [substance once] separated, is truly the essential salt of whey; or, on account of which nitre, is called "nitre of whey", and all [life] force is in this that will be expelled. [Note: "Nitre" was an alchemical concept. It was the power of life, which gave life to otherwise inanimate matter. See the philosophy of Sendivogius.] Dissolve it in [its] own water and coagulate. Repeat the operation until you have cream of whey, recalling, by [its] taste, only manna.)
    In 1688, the German physician Michael Ettmüller (1644–1683) reprinted Bartoletti's preparation. See: Ettmüller, Michael, Opera Omnia ... (Frankfurt am Main ("Francofurtum ad Moenum"), [Germany]: Johann David Zunner, 1688), book 2, page 163. Script error: No such module "webarchive". From page 163: "Undd Bertholetus praeparat ex sero lactis remedium, quod vocat mannam S. [alchemical symbol for salt, salem] seri lactis vid. in Encyclopaed. p. 400. Praeparatio est haec: ... " (Whence Bartoletti prepared from milk whey a medicine, which he called manna or salt of milk whey; see in [his] Encyclopedia [note: this is a mistake; the preparation appeared in Bartoletti's Methodus in dyspnoeam ... ], p. 400. This is the preparation: ... )
  31. ^ Lodovico Testi, De novo Saccharo Lactis [On the new milk sugar] (Venice, (Italy): Hertz, 1700).
  32. ^ Ludovico Testi (1715) "Saccharum lactis" (Milk sugar), Academiae Caesareo-Leopoldinae naturae curiosorum ephemerides, ... , 3 : 69–79. The procedure was also published in Giornale de' letterati d'Italia in 1715.
  33. ^ See:
    • Carl Wilhelm Scheele (1780) "Om Mjölk och dess syra" (About milk and its acid), Script error: No such module "Lang". (New Proceedings of the Royal Academy of Science), 1 : 116–124. From page 116: "Script error: No such module "Lang"., ... " (It is known, that cow's milk contains butter, cheese, milk-sugar, ... )
    • Carl Wilhelm Scheele (1780) "Om Mjölk-Såcker-Syra" (On milk-sugar acid), Script error: No such module "Lang". (New Proceedings of the Royal Academy of Science), 1 : 269–275. From pages 269–270: "Script error: No such module "Lang".." (Milk sugar is an essential salt, which is found dissolved in milk, and which, on account of its sweet taste, has the name of "sugar".)
  34. ^ See:
  35. ^ Pasteur (1856) "Note sur le sucre de lait" (Note on milk sugar), Comptes rendus, 42 : 347–351.
  36. ^ Fischer determined the configuration of glucose in:
    • Emil Fischer (1891) "Ueber die Configuration des Traubenzuckers und seiner Isomeren" (On the configuration of grape sugar and its isomers), Berichte der Deutschen Chemischen Gesellschaft, 24 : 1836–1845.
    • Emil Fischer (1891) "Ueber die Configuration des Traubenzuckers und seiner Isomeren. II" (On the configuration of grape sugar and its isomers), Berichte der Deutschen Chemischen Gesellschaft, 24 : 2683–2687.
    Fischer established the configuration of galactose in:
    • Emil Fischer and Robert S. Morrell (1894) "Ueber die Configuration der Rhamnose und Galactose" (On the configuration of rhamnose and galactose), Berichte der Deutschen chemischen Gesellschaft zu Berlin, 27 : 382–394. The configuration of galactose appears on page 385.
  37. ^ Dumas, Traité de Chimie, Appliquée aux Arts, volume 6 (Paris, France: Bechet Jeune, 1843), p. 293.
  38. ^ Pasteur (1856) "Note sur le sucre de lait" (Note on milk sugar), Comptes rendus, 42 : 347–351. From page 348: "Je propose de le nommer lactose." (I propose to name it lactose.)
  39. ^ Marcellin Berthelot, Chimie organique fondée sur la synthèse [Organic chemistry based on synthesis] (Paris, France: Mallet-Bachelier, 1860), vol. 2, pp. 248–249 and pp. 268–270.
  • Page Template:Sister-inline/styles.css has no content.Script error: No such module "Sister project logo". Media related to Script error: No such module "Commons link". at Wikimedia Commons

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