Lauric acid
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Names | |
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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)
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Identifiers | |
3D model (
JSmol ) |
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ChEBI | |
ChEMBL | |
ChemSpider | |
ECHA InfoCard
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100.005.075 |
EC Number |
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IUPHAR/BPS |
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KEGG | |
PubChem CID
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UNII | |
CompTox Dashboard (EPA)
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Properties | |
C12H24O2 | |
Molar mass | 200.322 g·mol−1 |
Appearance | White powder |
Odor | Slight odor of bay oil
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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] |
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 |
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
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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)
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1.423 (70 °C)[1] 1.4183 (82 °C)[3] |
Viscosity | 6.88 cP (50 °C) 5.37 cP (60 °C)[2] |
Structure | |
Monoclinic (α-form)[8] Triclinic, aP228 (γ-form)[9] | |
P21/a, No. 14 (α-form)[8] P1, No. 2 (γ-form)[9] | |
2/m (α-form)[8] 1 (γ-form)[9] | |
a = 9.524 Å, b = 4.965 Å, c = 35.39 Å (α-form)[8] α = 90°, β = 129.22°, γ = 90°
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Thermochemistry | |
Heat capacity (C)
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404.28 J/mol·K[4] |
Std enthalpy of (ΔfH⦵298)formation |
−775.6 kJ/mol[6] |
Std enthalpy of (ΔcH⦵298)combustion |
7377 kJ/mol 7425.8 kJ/mol (292 K)[4] |
Hazards | |
GHS labelling: | |
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Danger | |
H412[7] | |
P273[7] | |
NFPA 704 (fire diamond) | |
Flash point | > 113 °C (235 °F; 386 K)[7] |
Related compounds | |
Related compounds
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Glyceryl laurate
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Related compounds | |
Related compounds
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Sodium lauryl sulfate
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Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
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Lauric acid, systematically dodecanoic acid, is a
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] 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%[12]
- Citrullus lanatus(egusi melon)
- Pumpkin flower 205 ppm, pumpkin seed 472 ppm
Insect
- Black soldier fly Hermetia illucens 30–50 mg/100 mg fat.[13]
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 common initiator of polymerizations.[6]
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.[14] [15] Lauric acid induces apoptosis in cancer and promotes the proliferation of normal cells by maintaining cellular redox homeostasis. [16]
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".[17] In general, a lower total/HDL serum lipoprotein ratio correlates with a decrease in atherosclerotic incidence.[18] 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.[19] A 2016 review of coconut oil (which is nearly half lauric acid) was similarly inconclusive about the effects on cardiovascular disease incidence.[15]
References
- ^ 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.
- ^ ISBN 0-444-82802-8.
- ^ 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) (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 e f CID 3893 from PubChem
- ^ a b c d Sigma-Aldrich Co., Lauric acid. Retrieved on 2014-06-14.
- ^ .
- ^ 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.
- ^ S2CID 84492006.
- ^
- S2CID 213568257.
- S2CID 208604432.
- PMID 35360165.
- ^ PMID 26946252.
- .
- PMID 12716665.
- 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
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. ISBN 978-0-12-016437-0.
External links
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