Lauric acid

From Wikipedia, the free encyclopedia
(Redirected from Laurate)
Jump to navigation Jump to search

Script error: No such module "redirect hatnote". <templatestyles src="Chembox/styles.css"/>

Template:Chembox image cellTemplate:Chembox image cellTemplate:Chembox AllOtherNamesTemplate:Chembox headerbarTemplate:Chembox IndexlistTemplate:Chembox JmolTemplate:Chembox ChEMBLTemplate:Chembox ECHATemplate:Chembox E numberTemplate:Chembox IUPHAR ligandTemplate:Chembox UNIITemplate:Chembox CompToxTemplate:Chembox headerbarTemplate:Chembox SolubilityInWaterTemplate:Chembox headerbarTemplate:Chembox PointGroupTemplate:Chembox headerbarTemplate:Chembox headerbarTemplate:Chembox GHS (set)Template:Chembox headerbarTemplate:Chembox headerbarTemplate:Chembox Datapage checkTemplate:Chembox Footer
Lauric acid
Template:Longitem Template:Unbulleted list
ChEBI Template:Unbulleted list
ChemSpider Template:Unbulleted list
DrugBank Template:Unbulleted list
EC Number Template:Unbulleted list
KEGG Template:Unbulleted list
Template:Longitem Template:Unbulleted list
RTECS number Template:Unbulleted list
Script error: No such module "collapsible list".
Script error: No such module "collapsible list".
Template:Longitem Template:Chembox Elements/molecular formula
Molar mass Template:Chem molar mass
Appearance White powder
Odor Slight odor of bay oil
Density 1.007 g/cm3 (24 °C)[1]
0.8744 g/cm3 (41.5 °C)[2]
0.8679 g/cm3 (50 °C)[3]
Melting point Template:Chembox CalcTemperatures
Boiling point Template:Chembox CalcTemperatures
Solubility Soluble in alcohols, diethyl ether, phenyls, haloalkanes, acetates[5]
Solubility in methanol 12.7 g/100 g (0 °C)
120 g/100 g (20 °C)
2250 g/100 g (40 °C)[5]
Solubility in acetone 8.95 g/100 g (0 °C)
60.5 g/100 g (20 °C)
1590 g/100 g (40 °C)[5]
Solubility in ethyl acetate 9.4 g/100 g (0 °C)
52 g/100 g (20°C)
1250 g/100 g (40°C)[5]
Solubility in toluene 15.3 g/100 g (0 °C)
97 g/100 g (20°C)
1410 g/100 g (40°C)[5]
log P 4.6[6]
Vapor pressure 2.13·10−6 kPa (25 °C)[6]
0.42 kPa (150 °C)[4]
6.67 kPa (210 °C)[7]
Acidity (pKa) 5.3 (20 °C)[6]
Thermal conductivity 0.442 W/m·K (solid)[2]
0.1921 W/m·K (72.5 °C)
0.1748 W/m·K (106 °C)[1]
Template:Longitem 1.423 (70 °C)[1]
1.4183 (82 °C)[3]
Viscosity 6.88 cP (50 °C)
5.37 cP (60 °C)[2]
Template:Longitem Monoclinic (α-form)[8]
Triclinic, aP228 (γ-form)[9]
Template:Longitem P21/a, No. 14 (α-form)[8]
P1, No. 2 (γ-form)[9]
Template:Longitem
a = 9.524 Å, b = 4.965 Å, c = 35.39 Å (α-form)[8]
α = 90°, β = 129.22°, γ = 90°
Template:Longitem 404.28 J/mol·K[4]
Template:Longitem −775.6 kJ/mol[6]
Template:Longitem 7377 kJ/mol
7425.8 kJ/mol (292 K)[4]
NFPA 704 (fire diamond) Template:NFPA 704 diamond
Flash point Template:Chembox CalcTemperatures
Template:Longitem Glyceryl laurate
Template:Longitem Undecanoic acid
Tridecanoic acid
Dodecanol
Dodecanal
Sodium lauryl sulfate

Template:Chembox Footer/trackingScript error: No such module "TemplatePar".Template:Short description

Lauric acid, systematically dodecanoic acid, is a saturated fatty acid with a 12-carbon atom chain, thus having many properties of medium-chain fatty acids.[6] It is a bright white, powdery solid with a faint odor of bay oil or soap. The salts and esters of lauric acid are known as laurates.

Occurrence

Lauric acid, as a component of triglycerides, comprises about half of the fatty-acid content in coconut milk, coconut oil, laurel oil, and palm kernel oil (not to be confused with palm oil).[10][11] Oils with high levels of lauric acid are known as lauric oils.[12][13] Otherwise, it is relatively uncommon. It is also found in human breast milk (6.2% of total fat), cow's milk (2.9%), and goat's milk (3.1%).[10]

In various plants

Insect

Uses

Like many other fatty acids, lauric acid is inexpensive, has a long shelf-life, is nontoxic, and is safe to handle. It is used mainly for the production of soaps and cosmetics. For these purposes, lauric acid is reacted with sodium hydroxide to give sodium laurate, which is a soap. Most commonly, sodium laurate is obtained by saponification of various oils, such as coconut oil. These precursors give mixtures of sodium laurate and other soaps.[11]

Lauric acid is a precursor to dilauroyl peroxide, a commercial initiator of polymerizations.[6]

Production and reactions

Lauric acid is mainly isolated from natural sources.[11] Its reactions are representative of those of similar long chain, saturated fatty acids. It can be converted to the symmetrical fatty ketone called laurone (Template:Chem2).[16] It transesterifies with vinyl acetate.[17] Treatment with sulfur trioxide gives the α-sulfonic acid.[18]

Nutritional and medical aspects

Although 95% of medium-chain triglycerides are absorbed through the portal vein, only 25–30% of lauric acid is absorbed through it.[19][20] Lauric acid induces apoptosis in cancer and promotes the proliferation of normal cells by maintaining cellular redox homeostasis.[21]

Lauric acid increases total serum lipoproteins more than many other fatty acids, but mostly high-density lipoprotein (HDL). As a result, lauric acid has been characterized as having "a more favorable effect on total HDL than any other fatty acid [examined], either saturated or unsaturated".[22] In general, a lower total/HDL serum lipoprotein ratio correlates with a decrease in atherosclerotic incidence.[23] Nonetheless, an extensive meta-analysis on foods affecting the total LDL/serum lipoprotein ratio found in 2003 that the net effects of lauric acid on coronary artery disease outcomes remained uncertain.[24] A 2016 review of coconut oil (which is nearly half lauric acid) was similarly inconclusive about the effects on cardiovascular disease incidence.[20]

References

<templatestyles src="Reflist/styles.css" />

  1. ↑ a b c d Script error: No such module "citation/CS1".
  2. ↑ a b c Script error: No such module "citation/CS1".
  3. ↑ a b c Cite error: Script error: No such module "Namespace detect".Script error: No such module "Namespace detect".
  4. ↑ a b c d Dodecanoic acid in Linstrom, Peter J.; Mallard, William G. (eds.); NIST Chemistry WebBook, NIST Standard Reference Database Number 69, National Institute of Standards and Technology, Gaithersburg (MD) (retrieved 2014-06-14)
  5. ↑ a b c d e f Script error: No such module "citation/CS1".
  6. ↑ a b c d e f CID 3893 from PubChemTemplate:EditAtWikidataTemplate:WikidataCheck
  7. ↑ a b c Cite error: Script error: No such module "Namespace detect".Script error: No such module "Namespace detect".
  8. ↑ a b c d Script error: No such module "Citation/CS1".
  9. ↑ a b c Script error: No such module "citation/CS1".
  10. ↑ a b Script error: No such module "Citation/CS1".
  11. ↑ a b c David J. Anneken, Sabine Both, Ralf Christoph, Georg Fieg, Udo Steinberner, Alfred Westfechtel "Fatty Acids" in Ullmann's Encyclopedia of Industrial Chemistry 2006, Wiley-VCH, Weinheim. Script error: No such module "CS1 identifiers".
  12. ↑ Script error: No such module "citation/CS1".
  13. ↑ Script error: No such module "citation/CS1".
  14. ↑ Script error: No such module "Citation/CS1".
  15. ↑ Script error: No such module "Citation/CS1".
  16. ↑ Script error: No such module "Citation/CS1".
  17. ↑ Script error: No such module "Citation/CS1".
  18. ↑ Script error: No such module "Citation/CS1".
  19. ↑ Script error: No such module "Citation/CS1".
  20. ↑ a b Script error: No such module "Citation/CS1".
  21. ↑ Script error: No such module "Citation/CS1".
  22. ↑ Script error: No such module "Citation/CS1".
  23. ↑ Thijssen, M.A. and R.P. Mensink. (2005). Fatty Acids and Atherosclerotic Risk. In Arnold von Eckardstein (Ed.) Atherosclerosis: Diet and Drugs. Springer. pp. 171–172. Template:ISBN.
  24. ↑ Effects of dietary fatty acids and carbohydrates on the ratio of serum total to HDL cholesterol and on serum lipids and apolipoproteins: a meta-analysis of 60 controlled trials

Script error: No such module "Check for unknown parameters".

Further reading

  • Berner, Louise A. (1993). Defining the Role of Milkfat in Balanced Diets. In John E. Kinsella (Ed.) Advances in Food and Nutrition Research – Volume 37. Academic Press. pp. 159–166. Template:ISBN.

External links

Script error: No such module "Side box".

Script error: No such module "Navbox". Script error: No such module "Navbox". Template:Palm oil

Template:Authority control

Retrieved from "http://debianws.lexgopc.com/wiki143/index.php?title=Lauric_acid&oldid=2052059"