関: laurate、lauric acid

WordNet

street name for lysergic acid diethylamide (同)back breaker, battery-acid, dose, dot, Elvis, loony toons, Lucy in the sky with diamonds, pane, superman, window pane, Zen
any of various water-soluble compounds having a sour taste and capable of turning litmus red and reacting with a base to form a salt
having the characteristics of an acid; "an acid reaction"

PrepTutorEJDIC

酸性の / 酸味のある,すっぱい(sour) / (言葉・態度などが)厳しい,しんらつな / 酸 / すっぱいもの / 《俗》=LSD

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出典(authority):フリー百科事典『ウィキペディア（Wikipedia）』「2014/05/28 01:05:50」(JST)

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Lauric acid (systematically: dodecanoic acid), the saturated fatty acid with a 12-carbon atom chain, thus falling into the medium chain fatty acids, is a white, powdery solid with a faint odor of bay oil or soap.

Occurrence

Lauric acid, as a component of triglycerides, comprises about half of the fatty acid content in coconut oil, laurel oil, and in palm kernel oil (not to be confused with palm oil),^[2]^[3] 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%).^[2]

Properties

Like many other fatty acids, lauric acid is inexpensive, has a long shelf-life, and is non-toxic and safe to handle. It is mainly used for the production of soaps and cosmetics. For these purposes, lauric acid is neutralized 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.^[3]

Niche uses

In the laboratory, lauric acid is often used to investigate the molar mass of an unknown substance via the freezing-point depression. Lauric acid is convenient because its melting point when pure is relatively high (43.2 °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.^[4]

Potential medicinal properties

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.^[5]^[6]

Lauric acid increases total serum cholesterol the most of any fatty acid. 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, either saturated or unsaturated."^[7] In general, a lower total/HDL serum cholesterol ratio correlates with a decrease in atherosclerotic risk.^[8] 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.^[9]

References

^ Lide, D. R., ed. (2005). CRC Handbook of Chemistry and Physics (86th ed.). Boca Raton (FL): CRC Press. ISBN 0-8493-0486-5.
^ ^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
^ "Using Freezing Point Depression to find Molecular Weight". University of California, Irvine. 2010-04-12.
^ 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 ADM, 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

Lauric acid MS Spectrum

Appendix: occurrence of lauric acid in various foods

The palm tree Orbignya phalerata Mart, 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%
Citrullus lanatus (egusi melon)
Pumpkin flower 205 ppm, pumpkin seed 472 ppm

UpToDate Contents

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1. 尿酸のバランス uric acid balance
2. 出産時の臍帯血酸塩基分析 umbilical cord blood acid base analysis at delivery
3. 妊娠中の葉酸補充 folic acid supplementation in pregnancy
4. ポルフィリン症：概要 porphyrias an overview
5. 疾患予防におけるビタミン補給 vitamin supplementation in disease prevention

English Journal

Chlamydia trachomatis Scavenges Host Fatty Acids for Phospholipid Synthesis via an Acyl-Acyl Carrier Protein Synthetase.

Yao J1, Dodson VJ1, Frank MW1, Rock CO2.
The Journal of biological chemistry.J Biol Chem.2015 Sep 4;290(36):22163-73. doi: 10.1074/jbc.M115.671008. Epub 2015 Jul 20.
The obligate intracellular parasite Chlamydia trachomatis has a reduced genome but relies on de novo fatty acid and phospholipid biosynthesis to produce its membrane phospholipids. Lipidomic analyses showed that 8% of the phospholipid molecular species synthesized by C. trachomatis contained oleic a
PMID 26195634

Stability engineering of the Geobacillus stearothermophilus alcohol dehydrogenase and application for the synthesis of a polyamide 12 precursor.

Kirmair L1, Seiler DL, Skerra A.
Applied microbiology and biotechnology.Appl Microbiol Biotechnol.2015 Sep 2. [Epub ahead of print]
The thermostable NAD+-dependent alcohol dehydrogenase from Geobacillus stearothermophilus (BsADH) was exploited with regard to the biocatalytic synthesis of ω-oxo lauric acid methyl ester (OLAMe), a key intermediate for biobased polyamide 12 production, from the corresponding long-chain alcohol. Re
PMID 26329849

Spectrum of Membrane Morphological Responses to Antibacterial Fatty Acids and Related Surfactants.

Yoon BK, Jackman JA, Kim MC, Cho NJ.
Langmuir : the ACS journal of surfaces and colloids.Langmuir.2015 Sep 1. [Epub ahead of print]
Medium-chain saturated fatty acids and related compounds (e.g., monoglycerides) represent one class of membrane-active surfactants with antimicrobial properties. Most related studies have been in vitro evaluations of bacterial growth inhibition, and there is limited knowledge about how the compounds
PMID 26325618

Japanese Journal

Comparison of Acyl-CoA Synthetic Activities and Enantioselectivity toward 2-Arylpropanoic Acids in Firefly Luciferases

Kato Dai-ichiro,Yokoyama Keisuke,Hiraishi Yoshihiro [他],TAKEO Masahiro,NEGORO Seiji
Bioscience, biotechnology, and biochemistry 75(9), 1758-1762, 2011-09-23
… Measurement of thioesterification activities for dodecanoic acid (C12) and ketoprofen was done using five firefly luciferases, from <I>Pyrocoelia miyako</I> …
NAID 10029757305

Investigation of Koku Impact Compounds in Sweet Cream on the Basis of Sensory Evaluation and Separation Techniques

KOBAYASHI Noriaki,NISHIMURA Osamu
Food science and technology research 17(3), 233-240, 2011-05-01
… selected by sensory evaluation were analyzed by gas chromatography-mass spectroscopy, and 7 long-chain fatty acids (decanoic acid, dodecanoic acid, tetradecanoic acid, hexadecanoic acid, octadecanoic acid, oleic acid, and linoleic acid), 3 long-chain aliphatic delta-lactones (5-dodecanolide, 5-tetradecanolide, and 5-hexadecanolide), and cholesterol were identified …
NAID 10028259633

New Green Synthesis and Formulations of Acyclovir Prodrugs

Regil-Hernandez Ruben de,Martinez-Lagos Fernando,Rodriguez-Bayon Amalia [他],Sinisterra José-Vicente
Chemical and Pharmaceutical Bulletin 59(9), 1089-1093, 2011
… Hexanoic, decanoic, dodecanoic and tetradecanoic acyclovir esters were synthesized reacting acyclovir and the respective acid anhydride in dimethyl sulfoxide (DMSO), in solvents from renewable sources and without solvent (T=30°C). … The biosolvent, N,N-dimethylamide of decanoic acid, let us to obtain >95% yield at 24 h. …
NAID 130001852306

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★リンクテーブル★

リンク元	「ラウリン酸」「lauric acid」

「ラウリン酸」

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
PubChem	3893
ChemSpider	3756
ChEMBL	CHEMBL108766
Jmol-3D images	Image 1
	SMILES O=C(O)CCCCCCCCCCC ;
	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 ;
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
Boiling point	298.9 °C
Solubility in water	0.006 g/100 mL (20 °C)
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
	Except where noted otherwise, data are given for materials in their standard state (at 25 °C (77 °F), 100 kPa)
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	Infobox references

　　[★]

英: laurate, lauric acid
同: ドデカン酸 dodecanoic acid
関: 飽和直鎖脂肪酸

「lauric acid」

　　[★]

ラウリン酸

関: dodecanoic acid、laurate

[1] Lide, D. R., ed. (2005). CRC Handbook of Chemistry and Physics (86th ed.). Boca Raton (FL): CRC Press. ISBN 0-8493-0486-5.

[lexicon-2] 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-3] 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

[4] "Using Freezing Point Depression to find Molecular Weight". University of California, Irvine. 2010-04-12.

[5] 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.

[6] 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.

[Mensink2003-7] Mensink RP, Zock PL, Kester ADM, 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-8] 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.

[9] 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

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dodecanoic acid