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Lauric acid
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 Yes check.svgY
PubChem 3893
Properties
Molecular formula C12H24O2
Molar mass 200.31776
Appearance white powder
Odor slight odor of bay oil
Density 0.880 g/cm3
Melting point

44.2 °C[1]
Boiling point

298.9 °C
Solubility in water insoluble
Refractive index (nD) 1.423
Viscosity 7.30 mPa·s at 323 K
Hazards
Flash point ≥ 110 °C
Related compounds
Related compounds Glyceryl laurate
 Yes check.svgY (what is this?)  (verify)
Except where noted otherwise, data are given for materials in their standard state (at 25 °C, 100 kPa)
Infobox references

Lauric acid (systematically: dodecanoic acid), a saturated fatty acid, is a white, powdery solid with a faint odor of bay oil or soap.

Contents

Occurrence

Lauric acid is the main acid in coconut oil and in palm kernel oil (not to be confused with palm oil),[1] and is believed to have antimicrobial properties.[2][3][4] It is also found in human milk (6.2% of total fat), cow's milk (2.9%), and goat's milk (3.1%).[1]

Uses

Lauric acid is inexpensive, has a long shelf-life, and is non-toxic and safe to handle. Thus, it is often used in laboratory investigations of freezing-point depression. Lauric acid is a solid at room temperature but melts easily in boiling water, so liquid lauric acid can be treated with various solutes and used to determine their molecular masses.[citation needed]

References

  1. ^ a b c 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. http://iupac.org/publications/pac/73/4/0685/. 
  2. ^ Hoffman KL, Han IY, Dawson PL (2001). "Antimicrobial effects of corn zein films impregnated with nisin, lauric acid, and EDTA". J. Food Prot. 64 (6): 885–9. PMID 11403145. 
  3. ^ Ouattar B, Simard RE, Piett G, Bégin A, Holley RA (2000). "Inhibition of surface spoilage bacteria in processed meats by application of antimicrobial films prepared with chitosan". Int. J. Food Microbiol. 62 (1-2): 139–48. doi:10.1016/S0168-1605(00)00407-4. PMID 11139014. 
  4. ^ PL Dawson, GD Carl, JC Acton, and IY Han (1 May 2002). "Effect of lauric acid and nisin-impregnated soy-based films on the growth of Listeria monocytogenes on turkey bologna" (Free full text). Poultry Science 81 (5): 721–726. PMID 12033424. http://ps.fass.org/cgi/content/abstract/81/5/721. 

Further reading

Lipids: fatty acids
Saturated
Acetic (C2) • Propionic (C3) • Butyric (C4) • Valeric (C5) • Hexanoic (C6) • Heptanoic (C7) • Caprylic (C8) • Nonanoic (C9) • Decanoic (C10) • Lauric (C12) • Myristic (C14) • Palmitic (C16) • Heptadecanoic (C17) • Stearic (C18) • Arachidic (C20) • Behenic (C22) • Lignoceric (C24)
n−3 Unsaturated
n−6 Unsaturated
n−9 Unsaturated

Lauric acid
File:Lauric
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
PubChem 3893
Properties
Molecular formula C12H24O2
Molar mass 200.31776
Appearance white powder
Odor slight odor of bay oil
Density 0.880 g/cm3
Melting point

43.2 °C[1]

Boiling point

298.9 °C

Solubility in water insoluble
Refractive index (nD) 1.423
Viscosity 7.30 mPa·s at 323 K
Hazards
NFPA 704
1
1
1
Flash point ≥ 110 °C
Related compounds
Related compounds Glyceryl laurate
 Y (what is this?)  (verify)
Except where noted otherwise, data are given for materials in their standard state (at 25 °C, 100 kPa)
Infobox references

Lauric acid (systematically: dodecanoic acid), a saturated fatty acid, is a white, powdery solid with a faint odor of bay oil or soap.

Occurrence

Lauric acid is the main acid in coconut oil and in palm kernel oil (not to be confused with palm oil),[2] and is believed to have antimicrobial properties.[3][4][5][6] It is also found in human milk (6.2% of total fat), cow's milk (2.9%), and goat's milk (3.1%).[2]

Uses

Lauric acid is inexpensive, has a long shelf-life, and is non-toxic and safe to handle. Thus, it is often used in laboratory investigations of freezing-point depression. Lauric acid is a solid at room temperature but melts easily in boiling water, so liquid lauric acid can be treated with various solutes and used to determine their molecular masses. 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.[7]

References

  1. ^ Lide, D. R., ed. (2005), [Expression error: Unexpected < operator CRC Handbook of Chemistry and Physics] (86th ed.), Boca Raton (FL): CRC Press, ISBN 0-8493-0486-5 
  2. ^ 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. http://iupac.org/publications/pac/73/4/0685/. 
  3. ^ Hoffman KL, Han IY, Dawson PL (2001). [Expression error: Unexpected < operator "Antimicrobial effects of corn zein films impregnated with nisin, lauric acid, and EDTA"]. J. Food Prot. 64 (6): 885–9. PMID 11403145. 
  4. ^ Ouattar B, Simard RE, Piett G, Bégin A, Holley RA (2000). [Expression error: Unexpected < operator "Inhibition of surface spoilage bacteria in processed meats by application of antimicrobial films prepared with chitosan"]. Int. J. Food Microbiol. 62 (1-2): 139–48. doi:10.1016/S0168-1605(00)00407-4. PMID 11139014. 
  5. ^ PL Dawson, GD Carl, JC Acton, and IY Han (1 May 2002). "Effect of lauric acid and nisin-impregnated soy-based films on the growth of Listeria monocytogenes on turkey bologna" (Free full text). Poultry Science 81 (5): 721–726. PMID 12033424. http://ps.fass.org/cgi/content/abstract/81/5/721. 
  6. ^ Alexey Ruzin and Richard P. Novick (2000 May). "Equivalence of Lauric Acid and Glycerol Monolaurate as Inhibitors of Signal Transduction in Staphylococcus aureus" (Free full text). J Bacteriol 182 (9): 2668–2671. doi:10.1128/JB.182.9.2668-2671.2000. PMID 10762277. PMC 111339. http://www.pubmedcentral.nih.gov/articlerender.fcgi?artid=111339. 
  7. ^ Yang, D; Pornpattananangkul, D; Nakatsuji, T; Chan, M; Carson, D; Huang, CM; Zhang, L (2009). [Expression error: Unexpected < operator "The antimicrobial activity of liposomal lauric acids against Propionibacterium acnes."]. Biomaterials 30 (30): 6035–40. doi:10.1016/j.biomaterials.2009.07.033. PMID 19665786. 
[[Template:FULLPAGENAME: Fatty acids|v]] • [[{{TALKPAGENAME:Template:FULLPAGENAME: Fatty acids}}|d]] • [{{fullurl:Template:FULLPAGENAME: Fatty acids|action=edit}}e]
Lipids: fatty acids
Saturated
VFA: Acetic (C2)Template:· Propionic (C3)Template:· Butyric (C4)Template:· Valeric (C5)Template:· Caproic (C6)Template:· Enanthic (C7)Template:· Caprylic (C8)Template:· Pelargonic (C9)Template:· Capric (C10)Template:· Undecylic (C11)Template:· Lauric (C12)Template:· Tridecylic (C13)Template:· Myristic (C14)Template:· Pentadecylic (C15)Template:· Palmitic (C16)Template:· Margaric (C17)Template:· Stearic (C18)Template:· Nonadecylic (C19)Template:· Arachidic (C20)Template:· Heneicosylic (C21)Template:· Behenic (C22)Template:· Tricosylic (C23)Template:· Lignoceric (C24)Template:· Pentacosylic (C25)Template:· Cerotic (C26)Template:· Heptacosylic (C27)Template:· Montanic (C28)Template:· Nonacosylic (C29)Template:· Melissic (C30)Template:· Hentriacontylic (C31)Template:· Lacceroic (C32)Template:· Psyllic (C33)Template:· Geddic (C34)Template:· Ceroplastic (C35)Template:· Hexatriacontylic (C36)
n−3 Unsaturated
n−6 Unsaturated
n−9 Unsaturated
biochemical families: Carbohydrates (Glycosides, Alcohols)Template:· Lipids (Steroids, Phospholipids, Glycolipids, Fatty acids, Tetrapyrroles)Template:· Proteins (Amino acids, Peptides, Glycoproteins)Template:· Nucleobases/Nucleic acids

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