Lauric acid

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.

Lauric acid
Skeletal formula of lauric acid
Lauric-acid-3D-balls.png
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 check
3D model (JSmol)
  • Interactive image
ChEBI
  • CHEBI:30805 ☒
ChEMBL
  • ChEMBL108766 ☒
ChemSpider
  • 3756 ☒
ECHA InfoCard100.005.075 Edit this at Wikidata
EC Number
  • 205-582-1
IUPHAR/BPS
  • 5534
KEGG
  • C02679 ☒
PubChem CID
  • 3893
UNII
  • 1160N9NU9U check
CompTox Dashboard (EPA)
  • DTXSID5021590 Edit this at Wikidata
InChI
  • InChI=1S/C12H24O2/c1-2-3-4-5-6-7-8-9-10-11-12(13)14/h2-11H2,1H3,(H,13,14) ☒
    Key: POULHZVOKOAJMA-UHFFFAOYSA-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 mass200.322 g·mol−1
AppearanceWhite powder
OdorSlight odor of bay oil
Density1.007 g/cm3 (24 °C)[1]
0.8744 g/cm3 (41.5 °C)[2]
0.8679 g/cm3 (50 °C)[3]
Melting point43.8 °C (110.8 °F; 316.9 K)[3]
Boiling point297.9 °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]
SolubilitySoluble in alcoholsdiethyl etherphenylshaloalkanesacetates[5]
Solubility in methanol12.7 g/100 g (0 °C)
120 g/100 g (20 °C)
2250 g/100 g (40 °C)[5]
Solubility in acetone8.95 g/100 g (0 °C)
60.5 g/100 g (20 °C)
1590 g/100 g (40 °C)[5]
Solubility in ethyl acetate9.4 g/100 g (0 °C)
52 g/100 g (20°C)
1250 g/100 g (40°C)[5]
Solubility in toluene15.3 g/100 g (0 °C)
97 g/100 g (20°C)
1410 g/100 g (40°C)[5]
log P4.6[6]
Vapor pressure2.13·10−6 kPa (25 °C)[6]
0.42 kPa (150 °C)[4]
6.67 kPa (210 °C)[7]
Acidity (pKa)5.3 (20 °C)[6]
Thermal conductivity0.442 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]
Viscosity6.88 cP (50 °C)
5.37 cP (60 °C)[2]
Structure
Crystal structure
Monoclinic (α-form)[8]
TriclinicaP228 (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 fH298)
−775.6 kJ/mol[6]
Std enthalpy of
combustion cH298)
7377 kJ/mol
7425.8 kJ/mol (292 K)[4]
Hazards
GHS labelling:
Pictograms
GHS05: Corrosive
Signal word
Danger
Hazard statements
H412[7]
Precautionary statements
P273[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).
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Infobox references

Lauric acid was the most requested component for the production of superior quality napalm. With this coming in ~50% in the esterified form in coconut oil fatty acids.[10]

OccurrenceEdit

Lauric acid, as a component of triglycerides, comprises about half of the fatty-acid content in coconut milkcoconut oillaurel oil, and palm kernel oil (not to be confused with palm oil),[11][12] 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%).[11]

In various plantsEdit

  • 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%.[13]
  • 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

In InsectsEdit

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

PropertiesEdit

Although 95% of medium-chain triglycerides are absorbed through the portal vein, only 25–30% of lauric acid is absorbed through it.[16]

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.[12]

Laboratory useEdit

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.[17][citation needed]

Potential medicinal propertiesEdit

Lauric acid increases total serum cholesterol more than many other fatty acids, but mostly 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".[18] In general, a lower total/HDL serum cholesterol ratio correlates with a decrease in atherosclerotic risk.[19] 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.[20] A 2016 review of coconut oil (which is nearly half lauric acid) was similarly inconclusive about the effects on cardiovascular disease risk. 


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