lauric acid

{{chembox

| Verifiedfields = changed

| Watchedfields = changed

| verifiedrevid = 417697408

| ImageFile = Lauric acid.svg

| ImageSize =

| ImageName = Skeletal formula of lauric acid

| ImageFile2 = Lauric-acid-3D-balls.png

| ImageSize1 =

| ImageName1 = Ball-and-stick model of lauric acid

| PIN = Dodecanoic acid

| OtherNames =n-Dodecanoic acid, Dodecylic acid, Dodecoic acid,

Laurostearic acid, Vulvic acid, 1-Undecanecarboxylic acid, Duodecylic acid, C12:0 (Lipid numbers)

|Section1={{Chembox Identifiers

| IUPHAR_ligand = 5534

| CASNo_Ref = {{cascite|correct|CAS}}

| CASNo = 143-07-7

| UNII_Ref = {{fdacite|correct|FDA}}

| UNII = 1160N9NU9U

| ChEBI_Ref = {{ebicite|changed|EBI}}

| ChEBI = 30805

| ChEMBL_Ref = {{ebicite|changed|EBI}}

| ChEMBL = 108766

| PubChem = 3893

| ChemSpiderID_Ref = {{chemspidercite|changed|chemspider}}

| ChemSpiderID = 3756

| KEGG_Ref = {{keggcite|changed|kegg}}

| KEGG = C02679

| SMILES = O=C(O)CCCCCCCCCCC

| InChI = 1/C12H24O2/c1-2-3-4-5-6-7-8-9-10-11-12(13)14/h2-11H2,1H3,(H,13,14)

| InChIKey = POULHZVOKOAJMA-UHFFFAOYAP

| StdInChI_Ref = {{stdinchicite|changed|chemspider}}

| StdInChI = 1S/C12H24O2/c1-2-3-4-5-6-7-8-9-10-11-12(13)14/h2-11H2,1H3,(H,13,14)

| StdInChIKey_Ref = {{stdinchicite|changed|chemspider}}

| StdInChIKey = POULHZVOKOAJMA-UHFFFAOYSA-N

| EINECS = 205-582-1

}}

|Section2={{Chembox Properties

| C=12 | H=24 | O=2

| Appearance= White powder

| Odor = Slight odor of bay oil

| Density = 1.007 g/cm³ (24 °C)
0.8744 g/cm³ (41.5 °C)
0.8679 g/cm³ (50 °C)

| MeltingPtC = 43.8

| MeltingPt_ref = {{CRC90}}

| BoilingPtC = 297.9

| BoilingPt_notes =
{{convert|282.5|C|F K}}
at 512 mmHg{{cite web|url=http://dspace.unimap.edu.my/dspace/bitstream/123456789/14118/1/008_010_012_014-015_fatty%20a.pdf |title=Fatty acids used as phase change materials (PCMs) for thermal energy storage in building material applications |last1=G. |first1=Chuah T. |last2=D. |first2=Rozanna |last3=A. |first3=Salmiah |last4=Y. |first4=Thomas Choong S. |last5=M. |first5=Sa'ari |publisher=University Putra Malaysia |access-date=2014-06-22 |year=2006 |url-status=dead |archive-url=https://web.archive.org/web/20141103225311/http://dspace.unimap.edu.my/dspace/bitstream/123456789/14118/1/008_010_012_014-015_fatty%20a.pdf |archive-date=2014-11-03 }}
{{convert|225.1|C|F K}}
at 100 mmHg

| Viscosity = 6.88 cP (50 °C)
5.37 cP (60 °C)

| RefractIndex = 1.423 (70 °C)
1.4183 (82 °C)

| Solubility= 37 mg/L (0 °C)
55 mg/L (20 °C)
63 mg/L (30 °C)
72 mg/L (45 °C)
83 mg/L (100 °C){{cite book|last1 = Seidell|first1 = Atherton|last2 = Linke|first2 = William F.|year = 1952|title = Solubilities of inorganic and organic compounds|publisher = D. Van Nostrand Company|place = New York|edition = 3rd|pages = 742–743}}

| VaporPressure = 2.13·10⁻⁶ kPa (25 °C)
0.42 kPa (150 °C)
6.67 kPa (210 °C)

| pKa = 5.3 (20 °C){{PubChemLink|3893}}

| LogP = 4.6

| Solubility1 = 12.7 g/100 g (0 °C)
120 g/100 g (20 °C)
2250 g/100 g (40 °C)

| Solvent1 = methanol

| Solubility2 = 8.95 g/100 g (0 °C)
60.5 g/100 g (20 °C)
1590 g/100 g (40 °C)

| Solvent2 = acetone

| Solubility3 = 9.4 g/100 g (0 °C)
52 g/100 g (20°C)
1250 g/100 g (40°C)

| Solvent3 = ethyl acetate

| Solubility4 = 15.3 g/100 g (0 °C)
97 g/100 g (20°C)
1410 g/100 g (40°C)

| Solvent4 = toluene

| SolubleOther = Soluble in alcohols, diethyl ether, phenyls, haloalkanes, acetates

| ThermalConductivity = 0.442 W/m·K (solid){{cite book|last1 = Mezaki|first1 = Reiji|last2 = Mochizuki|first2 = Masafumi|last3 = Ogawa|first3 = Kohei|year = 2000|title = Engineering data on mixing|publisher = Elsevier Science B.V.|isbn = 0-444-82802-8|page = 278|url = https://books.google.com/books?id=6PDnxdmwlKUC&pg=PA278|edition = 1st}}
0.1921 W/m·K (72.5 °C)
0.1748 W/m·K (106 °C)

}}

|Section3={{Chembox Structure

| Dipole =

| CrystalStruct = Monoclinic (α-form)
Triclinic, aP228 (γ-form){{cite web|url = http://actachemscand.org/pdf/acta_vol_10_p0001-0008.pdf|title = On the structure of the crystal form A of lauric acid|last = Sydow|first = Erik von|website = actachemscand.org|publisher = Acta Chemica Scandinavica|access-date = 2014-06-14|year = 1956|volume = 10}}

| SpaceGroup = P2₁/a, No. 14 (α-form)
P{{overline|1}}, No. 2 (γ-form)

| PointGroup = 2/m (α-form)
{{overline|1}} (γ-form)

| LattConst_a = 9.524 Å

| LattConst_b = 4.965 Å

| LattConst_c = 35.39 Å (α-form){{Cite journal | doi = 10.1107/S0365110X51001069| title = The crystal structure of lauric acid| journal = Acta Crystallographica| volume = 4| issue = 4| pages = 324–329| year = 1951| last1 = Vand | first1 = V.| last2 = Morley | first2 = W. M.| last3 = Lomer | first3 = T. R.| doi-access = free| bibcode = 1951AcCry...4..324V}}

| LattConst_alpha =

| LattConst_beta = 129.22

| LattConst_gamma =

}}

|Section4={{Chembox Thermochemistry

| DeltaHc = 7377 kJ/mol
7425.8 kJ/mol (292 K){{nist|name=Dodecanoic acid|id=C143077|accessdate=2014-06-14|mask=FFFF|units=SI}}

| HeatCapacity = 404.28 J/mol·K

| DeltaHf = −775.6 kJ/mol

}}

|Section5={{Chembox Hazards

| MainHazards =

| GHSPictograms = {{GHS05}}

| GHSSignalWord = Danger

| HPhrases = {{H-phrases|318}}

| PPhrases = {{P-phrases|280|305+351+338}}

| FlashPtC = 113

| FlashPt = >

| FlashPt_ref = {{Sigma-Aldrich|id=w261416|name=Lauric acid|accessdate=2014-06-14}}

| AutoignitionPt =

| NFPA-H = 1

| NFPA-F = 1

| NFPA-R = 1

| NFPA-S =

}}

|Section6={{Chembox Related

| OtherCompounds = Glyceryl laurate

}}

|Section8={{Chembox Related

| OtherCompounds = Undecanoic acid
Tridecanoic acid
Dodecanol
Dodecanal
Sodium lauryl sulfate

}}

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. 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).{{cite journal |year=2001 |title=Lexicon of lipid nutrition (IUPAC Technical Report) |journal=Pure and Applied Chemistry |volume=73 |issue=4 |pages=685–744 |doi=10.1351/pac200173040685 |doi-access=free |last1=Beare-Rogers |first1=J. |last2=Dieffenbacher |first2=A. |last3=Holm |first3=J.V. |s2cid=84492006 }}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. {{doi|10.1002/14356007.a10_245.pub2}} Oils with high levels of lauric acid are known as lauric oils.{{cite encyclopedia|encyclopedia=Encyclopedia of Food and Health |last=Dijkstra |first=D.J. |title=Lauric Oils |doi=10.1016/B978-0-12-384947-2.00513-4 |date=2015|pages=517–522 |isbn=978-0-12-384953-3 }}{{cite book |chapter=The Lauric (Coconut and Palm Kernel) Oils |last=Amri |first=Ibrahim Nuzul |editor-last=Gunstone |editor-first=Frank D. |title=Vegetable Oils in Food Technology: Composition, Properties and Uses |edition=2 |date=2011 |pages=169–197 |doi=10.1002/9781444339925.ch6|isbn=978-1-4443-3268-1 }} 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%).

=In various plants=

The palm tree Attalea speciosa, a species popularly known in Brazil as babassu – 50% in babassu oil
Attalea cohune, the cohune palm (also rain tree, American oil palm, corozo palm or manaca palm) – 46.5% in cohune oil
Astrocaryum murumuru (Arecaceae) a palm native to the Amazon – 47.5% in "murumuru butter"
Coconut oil 49%
Pycnanthus kombo (African nutmeg)
Virola surinamensis (wild nutmeg) 7.8–11.5%
Peach palm seed 10.4%
Betel nut 9%
Date palm seed 0.56–5.4%
Macadamia nut 0.072–1.1%
Plum 0.35–0.38%
Watermelon seed 0.33%
Viburnum opulus 0.24-0.33%{{cite journal |title = Variation in volatile and fatty acid contents among Viburnum opulus L. Fruits growing different locations |year = 2019 |last1 = Zarifikhosroshahi |last2 = Tugba Murathan |last3 = Kafkas |last4 = Okatan |journal = Scientia Horticulturae |volume = 264 |page = 109160 |doi = 10.1016/j.scienta.2019.109160|s2cid = 213568257 }}
Citrullus lanatus (egusi melon)
Pumpkin flower 205 ppm, pumpkin seed 472 ppm

=Insect=

Black soldier fly Hermetia illucens 30–50 mg/100 mg fat.{{cite journal |year=2019 |title=Black soldier fly (Hermetia illucens L.): effect on the fat integrity using different approaches to the killing of the prepupae. |journal=Journal of Insects as Food and Feed |url=https://www.wageningenacademic.com/doi/abs/10.3920/JIFF2019.0002 |doi=10.3920/JIFF2019.0002 |last1=Montevecchi |first1=G. |last2=Zanasi |first2=L. |last3=Masino |first3=F. |last4=Maistrello |first4=L. |last5=Antonelli |first5=A.|volume=6 |issue=2 |pages=121–131 |s2cid=208604432 }}

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.

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

Production and reactions

Lauric acid is mainly isolated from natural sources. Its reactions are representative of those of similar long chain, saturated fatty acids. It can be converted to the symmetrical fatty ketone called laurone ({{chem2|O\dC(C_{11}H_{23})2}}).{{cite journal |author=J. C. Sauer|doi=10.15227/orgsyn.031.0068 |title=Laurone |journal=Organic Syntheses |date=1951 |volume=31 |page=68 }} It transesterifies with vinyl acetate.{{cite journal |doi=10.15227/orgsyn.030.0106 |title=Vinyl Laurate and Other Vinyl Esters |journal=Organic Syntheses |date=1950 |volume=30 |page=106|first1=Daniel|last1=Swern|first2=E. F.|last2=Jordan, Jr }} Treatment with sulfur trioxide gives the α-sulfonic acid.{{cite journal |doi=10.15227/orgsyn.036.0083 |title=α-Sulfopalmitic Acid |journal=Organic Syntheses |date=1956 |volume=36 |page=83| first1=J. K.|last1=Weil|first2=R. G.|last2=Bistline, Jr.|first3=A. J.|last3=Stirton }}

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.{{cite journal |title = Dual Roles of Coconut Oil and Its Major Component Lauric Acid on Redox Nexus: Focus on Cytoprotection and Cancer Cell Death |year = 2022 |journal = Frontiers in Neuroscience |volume = 16 |page = 833630 |doi = 10.3389/fnins.2022.833630 |doi-access = free |last1 = Ramya |first1 = Venkatesan |last2 = Shyam |first2 = Karuppiah Prakash |last3 = Kowsalya |first3 = Eshwaran |last4 = Balavigneswaran |first4 = Chelladurai Karthikeyan |last5 = Kadalmani |first5 = Balamuthu |pmid = 35360165 |pmc = 8963114 }}{{cite journal | vauthors=Eyres L, Eyres MF, Chisholm A, Brown RC | title=Coconut oil consumption and cardiovascular risk factors in humans | journal= Nutrition Reviews | volume=74 | issue=4 | pages=267–280 | year=2016 | doi= 10.1093/nutrit/nuw002 | pmc= 4892314 | pmid = 26946252 }} Lauric acid induces apoptosis in cancer and promotes the proliferation of normal cells by maintaining cellular redox homeostasis.{{cite journal |title = Lauric acid epigenetically regulates lncRNA HOTAIR by remodeling chromatin H3K4 tri-methylation and modulates glucose transport in SH-SY5Y human neuroblastoma cells: Lipid switch in macrophage activation |year = 2024 |journal = Biochimica et Biophysica Acta (BBA) - Molecular and Cell Biology of Lipids |volume = 1869 |issue = 1 |page = 159429 |url=https://www.sciencedirect.com/science/article/pii/S1388198123001531 |doi = 10.1016/j.bbalip.2023.159429 |last1 = Ramya |first1 = Venkatesan |last2 = Shyam |first2 = Karuppiah Prakash |last3 = Angelmary |first3 = Arulanandu |last4 = Kadalmani |first4 = Balamuthu |pmid = 37967739 }}

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".{{cite journal | title = 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 | url=http://www.ajcn.org/content/77/5/1146.full?ijkey=846a72387ebc0d82545acd5442a0c3a9e9fc3566 | journal =American Journal of Clinical Nutrition |vauthors=Mensink RP, Zock PL, Kester AD, Katan MB | volume=77 | issue=5 | pages = 1146–1155 |date=May 2003 | issn = 0002-9165 | pmid = 12716665|doi = 10.1093/ajcn/77.5.1146| doi-access =free }} In general, a lower total/HDL serum lipoprotein ratio correlates with a decrease in atherosclerotic incidence.Thijssen, M.A. and R.P. Mensink. (2005). [https://books.google.com/books?id=kvo6BN1AGNAC&pg=PA171 Fatty Acids and Atherosclerotic Risk]. In Arnold von Eckardstein (Ed.) Atherosclerosis: Diet and Drugs. Springer. pp. 171–172. {{ISBN|978-3-540-22569-0}}. 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.[http://ajcn.nutrition.org/content/77/5/1146.full?ijkey=846a72387ebc0d82545acd5442a0c3a9e9fc3566 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] A 2016 review of coconut oil (which is nearly half lauric acid) was similarly inconclusive about the effects on cardiovascular disease incidence.

References

External links

[http://gmd.mpimp-golm.mpg.de/Spectrums/82155059-5257-4809-a5d5-c30751495378.aspx Lauric acid MS Spectrum]

Category:Alkanoic acids