Lauric acid

Lauric acid
	; ;
	; ;
Names;
	; IUPAC name; Dodecanoic acid;
	Other names; ; n-Dodecanoic acid, Dodecylic acid, Dodecoic acid, ; Laurostearic acid, Vulvic acid, 1-Undecanecarboxylic acid, Duodecylic acid, C12:0 (Lipid numbers);
Identifiers;
; CAS Number;	; ; 143-07-7 Y; ; ;
; 3D model (JSmol);	; Interactive image; ;
; ChEBI;	; ; CHEBI:30805 N; ; ;
; ChEMBL;	; ; ChEMBL108766 N; ; ;
; ChemSpider;	; ; 3756 N; ; ;
; ECHA InfoCard;	; 100.005.075;
; EC Number;	205-582-1;
; IUPHAR/BPS;	; 5534; ;
; KEGG;	; ; D10714 N; ; ;
; ; PubChem CID; ;	; 3893; ;
	; ; InChI; ; ; InChI=1S/C12H24O2/c1-2-3-4-5-6-7-8-9-10-11-12(13)14/h2-11H2,1H3,(H,13,14) N; ; Key: POULHZVOKOAJMA-UHFFFAOYSA-N N; ; ; ; ; InChI=1/C12H24O2/c1-2-3-4-5-6-7-8-9-10-11-12(13)14/h2-11H2,1H3,(H,13,14); Key: POULHZVOKOAJMA-UHFFFAOYAP; ; ; ; ;
	; ; SMILES; O=C(O)CCCCCCCCCCC; ; ;
Properties;
; Chemical formula;	; C12H24O2;
; Molar mass;	200.32 g·mol−1;
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);
; Melting point;	43.8 °C (110.8 °F; 316.9 K);
; Boiling point;	297.9 °C (568.2 °F; 571.0 K) ; 282.5 °C (540.5 °F; 555.6 K); at 512 mmHg; 225.1 °C (437.2 °F; 498.2 K); at 100 mmHg;
; Solubility in water;	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);
; Solubility;	Soluble in alcohols, (C2H5)2O, phenyls, haloalkanes, acetates;
; Solubility in methanol;	12.7 g/100 g (0 °C); 120 g/100 g (20 °C); 2250 g/100 g (40 °C);
; Solubility in acetone;	8.95 g/100 g (0 °C); 60.5 g/100 g (20 °C); 1590 g/100 g (40 °C);
; Solubility in ethyl acetate;	9.4 g/100 g (0 °C); 52 g/100 g (20°C); 1250 g/100 g (40°C);
; Solubility in toluene;	15.3 g/100 g (0 °C); 97 g/100 g (20°C); 1410 g/100 g (40°C);
; log P;	4.6;
; Vapor pressure;	2.13·10−6 kPa (25 °C); 0.42 kPa (150 °C); 6.67 kPa (210 °C);
; Acidity (pKa);	5.3 (20 °C);
; Thermal conductivity;	0.442 W/m·K (solid); 0.1921 W/m·K (72.5 °C); 0.1748 W/m·K (106 °C);
; ; Refractive index (nD);	1.423 (70 °C); 1.4183 (82 °C);
; Viscosity;	6.88 cP (50 °C); 5.37 cP (60 °C);
Structure;
; Crystal structure;	; Monoclinic (α-form); Triclinic, aP228 (γ-form);
; Space group;	P21/a, No. 14 (α-form); P1, No. 2 (γ-form);
; Point group;	2/m (α-form); 1 (γ-form);
; Lattice constant;	; ; a = 9.524 Å, b = 4.965 Å, c = 35.39 Å (α-form); ; α = 90°, β = 129.22°, γ = 90°;
Thermochemistry;
; ; Heat capacity (C);	404.28 J/mol·K;
; ; Std enthalpy of; formation (ΔfHo298);	−775.6 kJ/mol;
; ; Std enthalpy of; combustion (ΔcHo298);	7377 kJ/mol; 7425.8 kJ/mol (292 K);
Hazards;
; GHS pictograms;	; ;
; GHS signal word;	Danger;
; GHS hazard statements;	; H412;
; GHS precautionary statements;	; P273;
; NFPA 704;	; ; ; ; ; ; ; ; ; 1; ; ; 1; ; ; 1; ; ;
; Flash point;	> 113 °C (235 °F; 386 K);
Related compounds;
; Related compounds;	; Glyceryl laurate;
Related compounds;
; Related compounds;	; Undecanoic acid, Tridecanoic acid;
	; Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).;
	; N verify (what is YN ?);
	; Infobox references;
;	;

Lauric acid or systematically, dodecanoic acid, is a saturated fatty acid with a 12-carbon atom chain, thus having many properties of medium-chain fatty acids, 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[edit]

Laurel oil contains lauric acid.

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] 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[edit]

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%

Durio graveolens (a species of durian) 1.31%.^[12]

Macadamia nut 0.072–1.1%

Plum 0.35–0.38%

Watermelon seed 0.33%

Citrullus lanatus (egusi melon)

Pumpkin flower 205 ppm, pumpkin seed 472 ppm

Properties[edit]

Although 95% of medium-chain triglycerides are absorbed through the portal vein, only 25-30% of lauric acid is absorbed through it.^[13]

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]

Laboratory use[edit]

In the laboratory, lauric acid may be used to investigate the molar mass of an unknown substance via the freezing-point depression. The choice of lauric acid is convenient because the melting point of the pure compound is relatively high (43.8°C). Its cryoscopic constant is 3.9°C·kg/mol. By melting lauric acid with the unknown substance, allowing it to cool, and recording the temperature at which the mixture freezes, the molar mass of the unknown compound may be determined.^[14]

Potential medicinal properties[edit]

In vitro experiments have suggested that some fatty acids including lauric acid could be a useful component in a treatment for acne, but no clinical trials have yet been conducted to evaluate this potential benefit in humans.^[15]^[16]

Lauric acid increases total serum cholesterol more than many other fatty acids, but most of the increase is attributable to an increase in high-density lipoprotein (HDL) (the "good" blood cholesterol). As a result, lauric acid has been characterized as having "a more favorable effect on total HDL cholesterol than any other fatty acid [examined], either saturated or unsaturated".^[17] In general, a lower total/HDL serum cholesterol ratio correlates with a decrease in atherosclerotic risk.^[18] Nonetheless, an extensive meta-analysis on foods affecting the total LDL /serum cholesterol ratio found in 2003 that the net effects of lauric acid on coronary artery disease outcomes remained uncertain.^[19] A 2016 review of coconut oil (which is nearly half lauric acid) was similarly inconclusive about the effects on cardiovascular disease risk.^[13]

References[edit]

^ ^a^b^c^d G., Chuah T.; D., Rozanna; A., Salmiah; Y., Thomas Choong S.; M., Sa'ari (2006). "Fatty acids used as phase change materials (PCMs) for thermal energy storage in building material applications" (PDF). University Putra Malaysia. Archived from the original (PDF) on 2014-11-03. Retrieved 2014-06-22..mw-parser-output cite.citation{font-style:inherit}.mw-parser-output q{quotes:"""""""'""'"}.mw-parser-output code.cs1-code{color:inherit;background:inherit;border:inherit;padding:inherit}.mw-parser-output .cs1-lock-free a{background:url("//upload.wikimedia.org/wikipedia/commons/thumb/6/65/Lock-green.svg/9px-Lock-green.svg.png")no-repeat;background-position:right .1em center}.mw-parser-output .cs1-lock-limited a,.mw-parser-output .cs1-lock-registration a{background:url("//upload.wikimedia.org/wikipedia/commons/thumb/d/d6/Lock-gray-alt-2.svg/9px-Lock-gray-alt-2.svg.png")no-repeat;background-position:right .1em center}.mw-parser-output .cs1-lock-subscription a{background:url("//upload.wikimedia.org/wikipedia/commons/thumb/a/aa/Lock-red-alt-2.svg/9px-Lock-red-alt-2.svg.png")no-repeat;background-position:right .1em center}.mw-parser-output .cs1-subscription,.mw-parser-output .cs1-registration{color:#555}.mw-parser-output .cs1-subscription span,.mw-parser-output .cs1-registration span{border-bottom:1px dotted;cursor:help}.mw-parser-output .cs1-hidden-error{display:none;font-size:100%}.mw-parser-output .cs1-visible-error{font-size:100%}.mw-parser-output .cs1-subscription,.mw-parser-output .cs1-registration,.mw-parser-output .cs1-format{font-size:95%}.mw-parser-output .cs1-kern-left,.mw-parser-output .cs1-kern-wl-left{padding-left:0.2em}.mw-parser-output .cs1-kern-right,.mw-parser-output .cs1-kern-wl-right{padding-right:0.2em}

^ ^a^b^c Mezaki, Reiji; Mochizuki, Masafumi; Ogawa, Kohei (2000). Engineering data on mixing (1st ed.). Elsevier Science B.V. p. 278. ISBN 0-444-82802-8.

^ ^a^b^c^d Lide, David R., ed. (2009). CRC Handbook of Chemistry and Physics (90th ed.). Boca Raton, Florida: CRC Press. ISBN 978-1-4200-9084-0.

^ ^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), http://webbook.nist.gov (retrieved 2014-06-14)

^ ^a^b^c^d^e^f Seidell, Atherton; Linke, William F. (1952). Solubilities of inorganic and organic compounds (3rd ed.). New York: D. Van Nostrand Company. pp. 742–743.

^ ^a^b^c^d CID 3893 from PubChem

^ ^a^b^c^d Sigma-Aldrich Co., Lauric acid. Retrieved on 2014-06-14.

^ ^a^b^c^d Vand, V.; Morley, W. M.; Lomer, T. R. (1951). "The crystal structure of lauric acid". Acta Crystallographica. 4 (4): 324–329. doi:10.1107/S0365110X51001069.

^ ^a^b^c Sydow, Erik von (1956). "On the structure of the crystal form A of lauric acid" (PDF). actachemscand.org. Acta Chemica Scandinavica. Retrieved 2014-06-14.

^ ^a^b Beare-Rogers, J.; Dieffenbacher, A.; Holm, J.V. (2001). "Lexicon of lipid nutrition (IUPAC Technical Report)". Pure and Applied Chemistry. 73 (4): 685–744. doi:10.1351/pac200173040685.

^ ^a^b 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

^ Nasaruddin, Mohd hanif; Noor, Noor Qhairul Izzreen Mohd; Mamat, Hasmadi (2013). "Komposisi Proksimat dan Komponen Asid Lemak Durian Kuning (Durio graveolens) Sabah" [Proximate and Fatty Acid Composition of Sabah Yellow Durian (Durio graveolens)] (PDF). Sains Malaysiana (in Malay). 42 (9): 1283–1288. ISSN 0126-6039. OCLC 857479186. Retrieved 28 November 2017.

^ ^a^b Eyres L, Eyres MF, Chisholm A, Brown RC (2016). "Coconut oil consumption and cardiovascular risk factors in humans". Nutrition Reviews. 74 (4): 267–280. doi:10.1093/nutrit/nuw002. PMC 4892314. PMID 26946252.

^ "Using Freezing Point Depression to find Molecular Weight" (PDF). University of California, Irvine. 2010-04-12. Archived from the original (PDF) on 2016-05-23.

^ Nakatsuji, T; Kao, MC; Fang, JY; Zouboulis, CC; Zhang, L; Gallo, RL; Huang, CM (2009). "Antimicrobial Property of Lauric Acid Against Propionibacterium acnes: Its Therapeutic Potential for Inflammatory Acne Vulgaris". The Journal of Investigative Dermatology. 129 (10): 2480–8. doi:10.1038/jid.2009.93. PMC 2772209. PMID 19387482.

^ Yang, D; Pornpattananangkul, D; Nakatsuji, T; Chan, M; Carson, D; Huang, CM; Zhang, L (2009). "The Antimicrobial Activity of Liposomal Lauric Acids Against Propionibacterium acnes". Biomaterials. 30 (30): 6035–40. doi:10.1016/j.biomaterials.2009.07.033. PMC 2735618. PMID 19665786.

^ Mensink RP, Zock PL, Kester AD, Katan MB (May 2003). "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". American Journal of Clinical Nutrition. 77 (5): 1146–1155. ISSN 0002-9165. PMID 12716665.

^ 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.
ISBN 978-3-540-22569-0.

^ 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

External links[edit]

Lauric acid MS Spectrum

[dspace-1] G., Chuah T.; D., Rozanna; A., Salmiah; Y., Thomas Choong S.; M., Sa'ari (2006). "Fatty acids used as phase change materials (PCMs) for thermal energy storage in building material applications" (PDF). University Putra Malaysia. Archived from the original (PDF) on 2014-11-03. Retrieved 2014-06-22..mw-parser-output cite.citation{font-style:inherit}.mw-parser-output q{quotes:"""""""'""'"}.mw-parser-output code.cs1-code{color:inherit;background:inherit;border:inherit;padding:inherit}.mw-parser-output .cs1-lock-free a{background:url("//upload.wikimedia.org/wikipedia/commons/thumb/6/65/Lock-green.svg/9px-Lock-green.svg.png")no-repeat;background-position:right .1em center}.mw-parser-output .cs1-lock-limited a,.mw-parser-output .cs1-lock-registration a{background:url("//upload.wikimedia.org/wikipedia/commons/thumb/d/d6/Lock-gray-alt-2.svg/9px-Lock-gray-alt-2.svg.png")no-repeat;background-position:right .1em center}.mw-parser-output .cs1-lock-subscription a{background:url("//upload.wikimedia.org/wikipedia/commons/thumb/a/aa/Lock-red-alt-2.svg/9px-Lock-red-alt-2.svg.png")no-repeat;background-position:right .1em center}.mw-parser-output .cs1-subscription,.mw-parser-output .cs1-registration{color:#555}.mw-parser-output .cs1-subscription span,.mw-parser-output .cs1-registration span{border-bottom:1px dotted;cursor:help}.mw-parser-output .cs1-hidden-error{display:none;font-size:100%}.mw-parser-output .cs1-visible-error{font-size:100%}.mw-parser-output .cs1-subscription,.mw-parser-output .cs1-registration,.mw-parser-output .cs1-format{font-size:95%}.mw-parser-output .cs1-kern-left,.mw-parser-output .cs1-kern-wl-left{padding-left:0.2em}.mw-parser-output .cs1-kern-right,.mw-parser-output .cs1-kern-wl-right{padding-right:0.2em}

[edm-2] Mezaki, Reiji; Mochizuki, Masafumi; Ogawa, Kohei (2000). Engineering data on mixing (1st ed.). Elsevier Science B.V. p. 278. ISBN 0-444-82802-8.

[crc-3] Lide, David R., ed. (2009). CRC Handbook of Chemistry and Physics (90th ed.). Boca Raton, Florida: CRC Press. ISBN 978-1-4200-9084-0.

[nist-4] 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), http://webbook.nist.gov (retrieved 2014-06-14)

[sioc-5] Seidell, Atherton; Linke, William F. (1952). Solubilities of inorganic and organic compounds (3rd ed.). New York: D. Van Nostrand Company. pp. 742–743.

[pubchem-6] CID 3893 from PubChem

[sigma-7] Sigma-Aldrich Co., Lauric acid. Retrieved on 2014-06-14.

[csba-8] Vand, V.; Morley, W. M.; Lomer, T. R. (1951). "The crystal structure of lauric acid". Acta Crystallographica. 4 (4): 324–329. doi:10.1107/S0365110X51001069.

[acta-9] Sydow, Erik von (1956). "On the structure of the crystal form A of lauric acid" (PDF). actachemscand.org. Acta Chemica Scandinavica. Retrieved 2014-06-14.

[lexicon-10] Beare-Rogers, J.; Dieffenbacher, A.; Holm, J.V. (2001). "Lexicon of lipid nutrition (IUPAC Technical Report)". Pure and Applied Chemistry. 73 (4): 685–744. doi:10.1351/pac200173040685.

[Ullmann-11] 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

[Nasaruddin-12] Nasaruddin, Mohd hanif; Noor, Noor Qhairul Izzreen Mohd; Mamat, Hasmadi (2013). "Komposisi Proksimat dan Komponen Asid Lemak Durian Kuning (Durio graveolens) Sabah" [Proximate and Fatty Acid Composition of Sabah Yellow Durian (Durio graveolens)] (PDF). Sains Malaysiana (in Malay). 42 (9): 1283–1288. ISSN 0126-6039. OCLC 857479186. Retrieved 28 November 2017.

[pmid26946252-13] Eyres L, Eyres MF, Chisholm A, Brown RC (2016). "Coconut oil consumption and cardiovascular risk factors in humans". Nutrition Reviews. 74 (4): 267–280. doi:10.1093/nutrit/nuw002. PMC 4892314. PMID 26946252.

[14] "Using Freezing Point Depression to find Molecular Weight" (PDF). University of California, Irvine. 2010-04-12. Archived from the original (PDF) on 2016-05-23.

[15] Nakatsuji, T; Kao, MC; Fang, JY; Zouboulis, CC; Zhang, L; Gallo, RL; Huang, CM (2009). "Antimicrobial Property of Lauric Acid Against Propionibacterium acnes: Its Therapeutic Potential for Inflammatory Acne Vulgaris". The Journal of Investigative Dermatology. 129 (10): 2480–8. doi:10.1038/jid.2009.93. PMC 2772209. PMID 19387482.

[16] Yang, D; Pornpattananangkul, D; Nakatsuji, T; Chan, M; Carson, D; Huang, CM; Zhang, L (2009). "The Antimicrobial Activity of Liposomal Lauric Acids Against Propionibacterium acnes". Biomaterials. 30 (30): 6035–40. doi:10.1016/j.biomaterials.2009.07.033. PMC 2735618. PMID 19665786.

[Mensink2003-17] Mensink RP, Zock PL, Kester AD, Katan MB (May 2003). "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". American Journal of Clinical Nutrition. 77 (5): 1146–1155. ISSN 0002-9165. PMID 12716665.

[Thijssen-18] 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.
ISBN 978-3-540-22569-0.

[19] 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

v t e Lipids: fatty acids
Saturated	Butyric (C4) Valeric (C5) Caproic (C6) Enanthic (C7) Caprylic (C8) Pelargonic (C9) Capric (C10) Undecylic (C11) Lauric (C12) Tridecylic (C13) Myristic (C14) Pentadecanoic (C15) Palmitic (C16) Margaric (C17) Stearic (C18) Nonadecylic (C19) Arachidic (C20) Heneicosylic (C21) Behenic (C22) Tricosylic (C23) Lignoceric (C24) Pentacosylic (C25) Cerotic (C26) Heptacosylic (C27) Montanic (C28) Nonacosylic (C29) Melissic (C30) Hentriacontylic (C31) Lacceroic (C32) Psyllic (C33) Geddic (C34) Ceroplastic (C35) Hexatriacontylic (C36) Heptatriacontanoic (C37) Octatriacontanoic (C38) Nonatriacontanoic (C39) Tetracontanoic (C40)
ω−3 Unsaturated	Octenoic (8:1) Decenoic (10:1) Decadienoic (10:2) Lauroleic (12:1) Laurolinoleic (12:2) Myristovaccenic (14:1) Myristolinoleic (14:2) Myristolinolenic (14:3) Palmitolinolenic (16:3) Palmitidonic (16:4) α-Linolenic (18:3) Stearidonic (18:4) Dihomo-α-linolenic (20:3) Eicosatetraeonic (20:4) Eicosapentaenoic (20:5) Clupanodonic (22:5) Docosahexaenoic (22:6) 9,12,15,18,21-Tetracosapentaenoic (24:5) 6,9,12,15,18,21-Tetracosahexaenoic (24:6)
ω−5 Unsaturated	Myristoleic (14:1) Palmitovaccenic (16:1) α-Eleostearic (18:3) β-Eleostearic (trans-18:3) Punicic (18:3) 7,10,13-Octadecatrienoic (18:3) 9,12,15-Eicosatrienoic (20:3) β-Eicosatetraenoic (20:4)
ω−6 Unsaturated	8-Tetradecenoic (14:1) 12-Octadecenoic (18:1) Linoleic (18:2) Linolelaidic (trans-18:2) γ-Linolenic (18:3) Calendic (18:3) Pinolenic (18:3) Dihomo-linoleic (20:2) Dihomo-γ-linolenic (20:3) Arachidonic (20:4) Adrenic (22:4) Osbond (22:5)
ω−7 Unsaturated	Palmitoleic (16:1) Vaccenic (18:1) Rumenic (18:2) Paullinic (20:1) 7,10,13-Eicosatrienoic (20:3)
ω−9 Unsaturated	Oleic (18:1) Elaidic (trans-18:1) Gondoic (20:1) Erucic (22:1) Nervonic (24:1) 8,11-Eicosadienoic (20:2) Mead (20:3)
ω−10 Unsaturated	Sapienic (16:1)
ω−11 Unsaturated	Gadoleic (20:1)
ω−12 Unsaturated	4-Hexadecenoic (16:1) Petroselinic (18:1) 8-Eicosenoic (20:1)
Fatty acids portal

v t e Types of lipids
General	Saturation: Saturated fat Unsaturated fat Monounsaturated fat Polyunsaturated fat Essential fatty acid Other: Fat Oil
Geometry	Trans fat Omega-3 fatty acid Omega-6 fatty acid Omega-9 fatty acid
Eicosanoids	Arachidonic acid Prostaglandins Prostacyclin Thromboxane Leukotrienes
Fatty acids	Caprylic acid Capric acid Lauric acid Myristic acid Palmitic acid Stearic acid Arachidic acid Behenic acid Lignoceric acid
Glycerides	Monoglyceride Diglyceride Triglyceride Triheptanoin Trimyristin Tripalmitin Tristearin Trilinolein Triolein
Phospholipids	Phosphatidylserine Phosphatidylinositol Phosphatidyl ethanolamine Cardiolipin Dipalmitoylphosphatidylcholine
Sphingolipids	Ceramide
Steroids	Cholesterol Corticosteroids Sex steroids Secosteroids
Lipids portal

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Lauric acid

Lauric acid

Contents

Occurrence[edit]

In various plants[edit]

Properties[edit]

Laboratory use[edit]

Potential medicinal properties[edit]

References[edit]

Further reading[edit]

External links[edit]

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Names


IUPAC name Dodecanoic acid
Other names n-Dodecanoic acid, Dodecylic acid, Dodecoic acid, Laurostearic acid, Vulvic acid, 1-Undecanecarboxylic acid, Duodecylic acid, C12:0 (Lipid numbers)
Identifiers
CAS Number	143-07-7^Y
3D model (JSmol)	Interactive image
ChEBI	CHEBI:30805^N
ChEMBL	ChEMBL108766^N
ChemSpider	3756^N
ECHA InfoCard	100.005.075
EC Number	205-582-1
IUPHAR/BPS	5534
KEGG	D10714^N
PubChem CID	3893
InChI InChI=1S/C12H24O2/c1-2-3-4-5-6-7-8-9-10-11-12(13)14/h2-11H2,1H3,(H,13,14)^N Key: POULHZVOKOAJMA-UHFFFAOYSA-N^N InChI=1/C12H24O2/c1-2-3-4-5-6-7-8-9-10-11-12(13)14/h2-11H2,1H3,(H,13,14) Key: POULHZVOKOAJMA-UHFFFAOYAP
SMILES O=C(O)CCCCCCCCCCC
Properties
Chemical formula	C₁₂H₂₄O₂
Molar mass	200.32 g·mol⁻¹
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	43.8 °C (110.8 °F; 316.9 K)^[3]
Boiling point	297.9 °C (568.2 °F; 571.0 K) 282.5 °C (540.5 °F; 555.6 K) at 512 mmHg^[1] 225.1 °C (437.2 °F; 498.2 K) at 100 mmHg^[3]^[4]
Solubility in water	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)^[5]
Solubility	Soluble in alcohols, (C₂H₅)₂O, 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 (pK_a)	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]
Refractive index (n_D)	1.423 (70 °C)^[1] 1.4183 (82 °C)^[3]
Viscosity	6.88 cP (50 °C) 5.37 cP (60 °C)^[2]
Structure
Crystal structure	Monoclinic (α-form)^[8] Triclinic, aP228 (γ-form)^[9]
Space group	P2₁/a, No. 14 (α-form)^[8] P1, No. 2 (γ-form)^[9]
Point group	2/m (α-form)^[8] 1 (γ-form)^[9]
Lattice constant	a = 9.524 Å, b = 4.965 Å, c = 35.39 Å (α-form)^[8] α = 90°, β = 129.22°, γ = 90°
Thermochemistry
Heat capacity (C)	404.28 J/mol·K^[4]
Std enthalpy of formation (Δ_fH^o₂₉₈)	−775.6 kJ/mol^[6]
Std enthalpy of combustion (Δ_cH^o₂₉₈)	7377 kJ/mol 7425.8 kJ/mol (292 K)^[4]
Hazards
GHS pictograms
GHS signal word	Danger
GHS hazard statements	H412^[7]
GHS precautionary statements	P273^[7]
NFPA 704	1 1 1
Flash point	> 113 °C (235 °F; 386 K)^[7]
Related compounds
Related compounds	Glyceryl laurate
Related compounds
Related compounds	Undecanoic acid, Tridecanoic acid
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
N verify (what is ^YN ?)
Infobox references