Lauric acid

"Laurate" redirects here. For the honorary title, see Laureate.

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.

Lauric acid

Skeletal formula of lauric acid
Names
Preferred 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	C02679 N
PubChem CID	3893
UNII	1160N9NU9U Y
CompTox Dashboard (EPA)	DTXSID5021590
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	200.322 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, 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]
Refractive index (nD)	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 (ΔfH⦵298)	−775.6 kJ/mol[6]
Std enthalpy of combustion (ΔcH⦵298)	7377 kJ/mol 7425.8 kJ/mol (292 K)[4]
Hazards
GHS labelling:
Pictograms
Signal word	Danger
Hazard statements	H318[7]
Precautionary statements	P280, P305+P351+P338[7]
NFPA 704 (fire diamond)	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 Dodecanol Dodecanal Sodium lauryl sulfate
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

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

• 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%^[14]
• Citrullus lanatus (egusi melon)
• Pumpkin flower 205 ppm, pumpkin seed 472 ppm

Insect

• Black soldier fly Hermetia illucens 30–50 mg/100 mg fat.^[15]

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 (O=C(C₁₁H₂₃)₂).^[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]