Lactose

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 lac (gen. lactis), 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.[1]

## Contents

* 1 Structure and reactions
* 2 Occurrence and isolation
* 3 Metabolism
* 4 Biological properties
* 5 Applications
* 6 History
* 7 See also
* 8 References
* 9 External links

## Structure and reactions

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[2] and Fearon tests.[3] 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.[4]

Lactose is hydrolysed to glucose and galactose, isomerised in alkaline solution to lactulose, and catalytically hydrogenated to the corresponding polyhydric alcohol, lactitol.[5] Lactulose is a commercial product, used for treatment of constipation.[6]

## 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.[7] Bovine milk has a concentration of around 4.8%.[8]

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.[9] 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.[10] Lactose can also be isolated by dilution of whey with ethanol.[11]

## Metabolism

See also: Medicine:Lactose intolerance and Lactase persistence

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.[12][13]

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.[14] The genes of adult lactose tolerance have evolved independently in various ethnic groups.[15][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.[16] 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.[17] 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.[17]

When lactose is completely digested in the small intestine, its caloric value is 4 kcal/g, or the same as that of other carbohydrates.[17] 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.[17] Undigested lactose acts as dietary fiber. It also has positive effects on absorption of minerals, such as calcium and magnesium.[17]

The glycemic index of lactose is 46 to 65.[18] 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.[17][18]

Lactose has relatively low cariogenicity among sugars.[19] This is because it is not a substrate for dental plaque formation and it is not rapidly fermented by oral bacteria.[19] The buffering capacity of milk also reduces the cariogenicity of lactose.[17]

## Applications

Its mild flavor and easy handling properties have led to its use as a carrier and stabiliser of aromas and pharmaceutical products.[1] Lactose is not commonly added directly to food, because its low solubility can lead to a gritty mouthfeel.[20] Infant formula is a notable exception, where lactose is added to match the composition of human milk.[21] However, lactose-reduced formulas are increasing in popularity.[22]

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.[5] 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.[23]

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).[1][24] For similar reasons, it can be used to dilute illicit drugs such as cocaine or heroin.[25]

## History

The first crude isolation of lactose, by Italian physician Fabrizio Bartoletti (1576–1630), was published in 1633.[26] In 1700, the Venetian pharmacist Lodovico Testi (1640–1707) published a booklet of testimonials to the power of milk sugar (saccharum lactis) to relieve, among other ailments, the symptoms of arthritis.[27] In 1715, Testi's procedure for making milk sugar was published by Antonio Vallisneri.[28] Lactose was identified as a sugar in 1780 by Carl Wilhelm Scheele.[29][5]

In 1812, Heinrich Vogel (1778–1867) recognized that glucose was a product of hydrolyzing lactose.[30] In 1856, Louis Pasteur crystallized the other component of lactose, galactose.[31] By 1894, Emil Fischer had established the configurations of the component sugars.[32]

Lactose was named by the French chemist Jean Baptiste André Dumas (1800–1884) in 1843.[33] In 1856, Pasteur named galactose "lactose".[34] In 1860, Marcellin Berthelot renamed it "galactose", and transferred the name "lactose" to what is now called lactose.[35] It has a formula of C
12H
22O
11 and the hydrate formula C
12H
22O
11·H
2O, making it an isomer of sucrose.

## See also

* Lac operon
* Lactic acid
* Lactose intolerance
* Nectar
* Sugars in wine

## References

1. ↑ 1.0 1.1 1.2 Gerrit M. Westhoff; Ben F.M. Kuster; Michiel C. Heslinga; Hendrik Pluim; Marinus Verhage (2014). Ullmann's Encyclopedia of Industrial Chemistry. Wiley-VCH. pp. 1–9. doi:10.1002/14356007.a15_107.pub2. ISBN 978-3-527-30673-2.
2. ↑ Ruppersberg, Klaus; Blankenburg, Janet (2018). "150 Years Alfred Wöhlk". ChemViews. doi:10.1002/chemv.201800002. http://www.chemistryviews.org/details/education/10821368/150_Years_Alfred_Wohlk.html.
3. ↑ Fearon, W. R. (1942). "The detection of lactose and maltose by means of methylamine" (in en). The Analyst 67 (793): 130. doi:10.1039/an9426700130. ISSN 0003-2654. Bibcode: 1942Ana....67..130F. http://xlink.rsc.org/?DOI=an9426700130.
4. ↑ 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.
5. ↑ 5.0 5.1 5.2 Linko, P (1982), "Lactose and Lactitol", in Birch, G.G.; Parker, K.J, Natural Sweeteners, London & New Jersey: Applied Science Publishers, pp. 109–132, ISBN 978-0-85334-997-6, https://archive.org/details/nutritivesweeten0000unse
6. ↑ 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, https://linkinghub.elsevier.com/retrieve/pii/B9780323430449001047, retrieved 2025-02-15
7. ↑ Newmark, Lauren (2017). "Milk Lactose From A to Zebra". https://www.milkgenomics.org/?splash=milk-lactose-zebra.
8. ↑ Program, Human Foods (2024-09-05). "Raw Milk Misconceptions and the Danger of Raw Milk Consumption" (in en). FDA. https://www.fda.gov/food/buy-store-serve-safe-food/raw-milk-misconceptions-and-danger-raw-milk-consumption.
9. ↑ Ranken, M. D.; Kill, R. C. (1997), Food industries manual, Springer, p. 125, ISBN 978-0-7514-0404-3, https://archive.org/details/foodindustriesma0000unse
10. ↑ 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
11. ↑ Pavia, Donald L.; Lampman, Gary M.; Kriz, George S. (1990), Introduction to Organic Laboratory Techniques: A Microscale Approach, Saunders, ISBN 0-03-014813-8
12. ↑ Balaresque, P.; King, T. E. (2010). "Nine - Human Phenotypic Diversity: An Evolutionary Perspective". in Orgogozo, Virginie. Current Topics in Developmental Biology. Genes and Evolution. 119. Academic Press. pp. 349–390. ISBN 9780124171947. https://linkinghub.elsevier.com/retrieve/pii/S0070215316300011. Retrieved 2025-02-15.
13. ↑ 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" (in en). Philosophical Transactions of the Royal Society B: Biological Sciences 366 (1566): 863–877. doi:10.1098/rstb.2010.0268. ISSN 0962-8436. PMID 21320900.
14. ↑ 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" (in en). PLOS Computational Biology 5 (8). doi:10.1371/journal.pcbi.1000491. ISSN 1553-7358. PMID 19714206. Bibcode: 2009PLSCB...5E0491I.
15. ↑ Wade, Nicholas (2006-12-10), "Study Detects Recent Instance of Human Evolution", New York Times, https://www.nytimes.com/2006/12/10/science/10cnd-evolve.html?
16. ↑ Ridley, Matt (1999), Genome, HarperCollins, p. 193, ISBN 978-0-06-089408-5 .
17. ↑ 17.0 17.1 17.2 17.3 17.4 17.5 17.6 Schaafsma, Gertjan (2008). "Lactose and lactose derivatives as bioactive ingredients in human nutrition". International Dairy Journal 18 (5): 458–465. doi:10.1016/j.idairyj.2007.11.013. ISSN 0958-6946. http://pdfs.semanticscholar.org/a45b/ce8eb621c78f163ec94f6e2c5add17a624e4.pdf.
18. ↑ 18.0 18.1 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.
19. ↑ 19.0 19.1 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. https://books.google.com/books?id=5tleQ0aLJvoC&pg=PA248.
20. ↑ 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" (in en). Foods 11 (10): 1486. doi:10.3390/foods11101486. ISSN 2304-8158. PMID 35627056.
21. ↑ 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" (in en). Scientific Reports 7 (1): 3640. doi:10.1038/s41598-017-03975-4. ISSN 2045-2322. PMID 28623320. Bibcode: 2017NatSR...7.3640S.
22. ↑ 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" (in en). Journal of Pediatric Gastroenterology and Nutrition 79 (5): 1017–1023. doi:10.1002/jpn3.12292. ISSN 1536-4801. PMID 38934419. https://onlinelibrary.wiley.com/doi/10.1002/jpn3.12292.
23. ↑ Ling, Charles (2008), Whey to Ethanol: A Biofuel Role for Dairy Cooperatives?, United States Department of Agriculture Rural Development, http://www.rd.usda.gov/files/RR214.pdf .
24. ↑ 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. https://pimr.pl/index.php/issues/2018-vol-14-no-3/lactose-in-drugs-and-lactose-intolerance-realities-and-myths.
25. ↑ Rinaldi, R.; Negro, F.; Minutillo, A. (2020-02-20). "The health threat of new synthetic opioids as adulterants of classic drugs of abuse". La Clinica Terapeutica 171 (2): 107–109. doi:10.7417/CT.2020.2198. ISSN 1972-6007. PMID 32141480. http://www.clinicaterapeutica.it/2020/171/2/05_MINUTILLO.pdf.
26. ↑ Fabrizio Bartoletti, Methodus in dyspnoeam ... [Procedure for asthma ... ], (Bologna ("Bononia"), (Italy): Nicolò Tebaldini for the heirs of Evangelista Dozza, 1633), p. 400. From page 400: "Manna seri hæc. Destilla leni balnei calore serum lactis, donec in fundo vasis butyracea fœx subsideat, cui hærebit salina quædam substantia subalbida. Hanc curiose segrega, est enim sal seri essentiale; seu nitrum, cujus causa nitrosum dicitut serum, huicque tota abstergedi vis inest. Solve in aqua propria, & coagula. Opus repete, donec seri cremorem habeas sapore omnino mannam referentem." (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. 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: ... )
27. ↑ Lodovico Testi, De novo Saccharo Lactis [On the new milk sugar] (Venice, (Italy): Hertz, 1700).
28. ↑ 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.
29. ↑ See:
* Carl Wilhelm Scheele (1780) "Om Mjölk och dess syra" (About milk and its acid), Kongliga Vetenskaps Academiens Nya Handlingar (New Proceedings of the Royal Academy of Science), 1 : 116–124. From page 116: "Det år bekant, at Ko-mjölk innehåller Smör, Ost, Mjölk-såcker, ... " (It is known, that cow's milk contains butter, cheese, milk-sugar, ... )
* Carl Wilhelm Scheele (1780) "Om Mjölk-Såcker-Syra" (On milk-sugar acid), Kongliga Vetenskaps Academiens Nya Handlingar (New Proceedings of the Royal Academy of Science), 1 : 269–275. From pages 269–270: "Mjölk-Såcker år et sal essentiale, som uti Mjölken finnes uplöst, och som, för dess sötaktiga smak skull, fått namn af såcker." (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".)
30. ↑ See:
* Vogel (1812) "Sur le sucre liquide d'amidon, et sur la transmutation des matières douces en sucre fermentescible" (On the liquid sugar of starch, and on the transformation of sweet materials into fermentable sugars), Annales de chemie et de physique, series 1, 82 : 148–164; see especially pages 156–158.
* H. A. Vogel (1812) "Ueber die Verwandlung der Stärke und andrer Körper in Zucker" (On the conversion of starches and other substances into sugar), Annalen der Physik, new series, 42 : 123–134; see especially pages 129–131.
31. ↑ Pasteur (1856) "Note sur le sucre de lait" (Note on milk sugar), Comptes rendus, 42 : 347–351.
32. ↑ 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.
33. ↑ Dumas, Traité de Chimie, Appliquée aux Arts, volume 6 (Paris, France: Bechet Jeune, 1843), p. 293.
34. ↑ 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.)
35. ↑ 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.

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