ミリスチン酸、ミリスチン酸エステル
- 関
- myristic acid
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出典(authority):フリー百科事典『ウィキペディア（Wikipedia）』「2015/07/22 18:42:38」(JST)
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Myristic acid[1]
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| Names |
| IUPAC name
Tetradecanoic acid
|
| Other names
C14:0 (Lipid numbers)
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| Identifiers |
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CAS Registry Number
|
544-63-8 Y |
| ChEBI |
CHEBI:28875 N |
| ChEMBL |
ChEMBL111077 N |
| ChemSpider |
10539 N |
| EC number |
208-875-2 |
InChI
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InChI=1S/C14H28O2/c1-2-3-4-5-6-7-8-9-10-11-12-13-14(15)16/h2-13H2,1H3,(H,15,16) N
Key: TUNFSRHWOTWDNC-UHFFFAOYSA-N N
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InChI=1/C14H28O2/c1-2-3-4-5-6-7-8-9-10-11-12-13-14(15)16/h2-13H2,1H3,(H,15,16)
Key: TUNFSRHWOTWDNC-UHFFFAOYAZ
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IUPHAR/BPS
|
2806 |
| Jmol-3D images |
Image |
| PubChem |
11005 |
| RTECS number |
QH4375000 |
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| UNII |
0I3V7S25AW N |
| Properties |
|
Chemical formula
|
C14H28O2 |
| Molar mass |
228.38 g·mol−1 |
| Density |
1.03 g/cm3 (−3 °C)[2]
0.99 g/cm3 (24 °C)[3]
0.8622 g/cm3 (54 °C)[4] |
| Melting point |
54.4 °C (129.9 °F; 327.5 K) [9] |
| Boiling point |
326.2 °C (619.2 °F; 599.3 K) at 760 mmHg
250 °C (482 °F; 523 K)
at 100 mmHg[4]
218.3 °C (424.9 °F; 491.4 K)
at 32 mmHg[3] |
|
Solubility in water
|
13 mg/L (0 °C)
20 mg/L (20 °C)
24 mg/L (30 °C)
33 mg/L (60 °C)[5] |
| Solubility |
Soluble in alcohol, acetates, C6H6, haloalkanes, phenyls, nitros[5] |
| Solubility in acetone |
2.75 g/100 g (0 °C)
15.9 g/100 g (20 °C)
42.5 g/100 g (30 °C)
149 g/100 g (40 °C)[5] |
| Solubility in benzene |
6.95 g/100 g (10 °C)
29.2 g/100 g (20 °C)
87.4 g/100 g (30 °C)
1.29 kg/100 g (50 °C)[5] |
| Solubility in methanol |
2.8 g/100 g (0 °C)
17.3 g/100 g (20 °C)
75 g/100 g (30 °C)
2.67 kg/100 g (50 °C)[5] |
| Solubility in ethyl acetate |
3.4 g/100 g (0 °C)
15.3 g/100 g (20 °C)
44.7 g/100 g (30 °C)
1.35 kg/100 g (40 °C)[5] |
| Solubility in toluene |
0.6 g/100 g (−10 °C)
3.2 g/100 g (0 °C)
30.4 g/100 g (20 °C)
1.35 kg/100 g (50 °C)[5] |
| log P |
6.1[4] |
| Vapor pressure |
0.01 kPa (118 °C)
0.27 kPa (160 °C)[6]
1 kPa (186 °C)[4] |
| Thermal conductivity |
0.159 W/m·K (70 °C)
0.151 W/m·K (100 °C)
0.138 W/m·K (160 °C)[7] |
|
Refractive index (nD)
|
1.4723 (70 °C)[4] |
| Viscosity |
7.2161 cP (60 °C)
3.2173 cP (100 °C)
0.8525 cP (200 °C)
0.3164 cP (300 °C)[8] |
| Structure |
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Crystal structure
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Monoclinic (−3 °C)[2] |
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Space group
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P21/c[2] |
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Lattice constant
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a = 31.559 Å, b = 4.9652 Å, c = 9.426 Å[2]
α = 90°, β = 94.432°, γ = 90°
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| Thermochemistry |
|
Specific
heat capacity (C)
|
432.01 J/mol·K[4][6] |
|
Std enthalpy of
formation (ΔfHo298)
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−833.5 kJ/mol[4][6] |
|
Std enthalpy of
combustion (ΔcHo298)
|
8675.9 kJ/mol[6] |
| Hazards |
| GHS pictograms |
[10] |
| GHS signal word |
Warning |
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GHS hazard statements
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H315[10] |
| EU classification |
Xi |
| R-phrases |
R36/37/38 |
| NFPA 704 |
|
| Flash point |
> 110 °C (230 °F; 383 K) [11] |
| Lethal dose or concentration (LD, LC): |
|
LD50 (Median dose)
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10 mg/kg (rats, oral)[11] |
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
|
| N verify (what is: Y/N?) |
| Infobox references |
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|
Myristic acid, also called tetradecanoic acid, is a common saturated fatty acid with the molecular formula CH3(CH2)12COOH. A myristate is a salt or ester of myristic acid. Myristic acid is named after the nutmeg Myristica fragrans.
Contents
- 1 Occurrence
- 2 Uses
- 3 References
- 4 External links
Occurrence
Myristica fragrans fruit contains myristic acid
Nutmeg butter has 75% trimyristin, the triglyceride of myristic acid. Besides nutmeg, myristic acid is also found in palm kernel oil, coconut oil, butter fat and is a minor component of many other animal fats.[9] It is also found in spermaceti, the crystallized fraction of oil from the sperm whale.
Uses
Myristic acid is commonly added co-translationally to the penultimate, nitrogen-terminus, glycine in receptor-associated kinases to confer the membrane localisation of the enzyme.[citation needed] The myristic acid has a sufficiently high hydrophobicity to become incorporated into the fatty acyl core of the phospholipid bilayer of the plasma membrane of the eukaryotic cell. In this way, myristic acid acts as a lipid anchor in biomembranes.[citation needed]
The ester isopropyl myristate is used in cosmetic and topical medicinal preparations where good absorption through the skin is desired[citation needed].
Reduction of myristic acid yields myristyl aldehyde and myristyl alcohol.
References
- ^ Merck Index, 11th Edition, 6246
- ^ a b c d Bond, Andrew D. (2003). "On the crystal structures and melting point alternation of the n-alkyl carboxylic acids" (PDF). http://www.rsc.org. Royal Society of Chemistry. Retrieved 2014-06-17.
- ^ a b 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. Retrieved 2014-06-17.
- ^ a b c d e f g Lide, David R., ed. (2009). CRC Handbook of Chemistry and Physics (90th ed.). Boca Raton, Florida: CRC Press. ISBN 978-1-4200-9084-0.
- ^ a b c d e f g Seidell, Atherton; Linke, William F. (1940). Solubilities of Inorganic and Organic Compounds (3rd ed.). New York: D. Van Nostrand Company. pp. 762–763.
- ^ a b c d Tetradecanoic acid in Linstrom, P.J.; Mallard, W.G. (eds.) NIST Chemistry WebBook, NIST Standard Reference Database Number 69. National Institute of Standards and Technology, Gaithersburg MD. http://webbook.nist.gov (retrieved 2014-06-17)
- ^ Vargaftik, Natan B.; et al. (1993). Handbook of Thermal Conductivity of Liquids and Gases (illustrated ed.). CRC Press. p. 305. ISBN 0-8493-9345-0.
- ^ Yaws, Carl L. (2009). Transport Properties of Chemicals and Hydrocarbons. New York: William Andrew Inc. p. 177. ISBN 978-0-8155-2039-9.
- ^ a b "Lexicon of lipid nutrition (IUPAC Technical Report)". Pure and Applied Chemistry 73 (4): 685–744. 2001. doi:10.1351/pac200173040685.
- ^ a b Sigma-Aldrich Co., Myristic acid. Retrieved on 2014-06-17.
- ^ a b c "MYRISTIC ACID". https://www.chemicalland21.com. AroKor Holdings Inc. Retrieved 2014-06-17.
External links
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Wikimedia Commons has media related to Myristic acid. |
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Lipids: fatty acids
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| Saturated |
- Acetic (C2)
- Propionic (C3)
- Butyric (C4)
- Valeric (C5)
- Caproic (C6)
- Enanthic (C7)
- Caprylic (C8)
- Pelargonic (C9)
- Capric (C10)
- Undecylic (C11)
- Lauric (C12)
- Tridecylic (C13)
- Myristic (C14)
- Pentadecanoic (C15)
- Palmitic (C16)
- Margaric (C17)
- Stearic (C18)
- Nonadecylic (C19)
- Arachidic (C20)
- Heneicosylic (C21)
- Behenic (C22)
- Tricosylic (C23)
- Lignoceric (C24)
- Pentacosylic (C25)
- Cerotic (C26)
- Heptacosylic (C27)
- Montanic (C28)
- Nonacosylic (C29)
- Melissic (C30)
- Hentriacontylic (C31)
- Lacceroic (C32)
- Psyllic (C33)
- Geddic (C34)
- Ceroplastic (C35)
- Hexatriacontylic (C36)
- Heptatriacontanoic (C37)
- Octatriacontanoic (C38)
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| ω−3 Unsaturated |
- α-Linolenic (18:3)
- Stearidonic (18:4)
- Eicosapentaenoic (20:5)
- Docosahexaenoic (22:6)
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|
| ω−6 Unsaturated |
- Linoleic (18:2)
- γ-Linolenic (18:3)
- Dihomo-γ-linolenic (20:3)
- Arachidonic (20:4)
- Adrenic (22:4)
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| ω-7 Unsaturated |
- Palmitoleic (16:1)
- Vaccenic (18:1)
- Paullinic (20:1)
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| ω−9 Unsaturated |
- Oleic (18:1)
- Elaidic (trans-18:1)
- Gondoic (20:1)
- Erucic (22:1)
- Nervonic (24:1)
- Mead (20:3)
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Index of biochemical families
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| Carbohydrates |
- Alcohols
- Glycoproteins
- Glycosides
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| Lipids |
- Eicosanoids
- Fatty acids
- Glycerides
- Phospholipids
- Sphingolipids
- Steroids
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| Nucleic acids |
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| Proteins |
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| Other |
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UpToDate Contents
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English Journal
- Development of innovative oil-core self-organized nanovesicles prepared with chitosan and lecithin using a 2(3) full-factorial design.
- Haas SE1, de Andrade C, Sansone PE, Guterres S, Dalla Costa T.
- Pharmaceutical development and technology.Pharm Dev Technol.2014 Nov;19(7):769-78. doi: 10.3109/10837450.2013.829094. Epub 2013 Sep 2.
- The aim of this study was to develop innovative nanosystems with isopropyl myristate as the oil core of self-assembly nanovesicles constituted of chitosan and lecithin using a 2(3) factorial design. The factors analyzed were chitosan (X1, levels 4 and 8 mg/ml), oil (X2, levels 10 and 20 mg/ml)
- PMID 23998248
- Peroxisomal membrane channel Pxmp2 in the mammary fat pad is essential for stromal lipid homeostasis and for development of mammary gland epithelium in mice.
- Vapola MH1, Rokka A1, Sormunen RT2, Alhonen L3, Schmitz W4, Conzelmann E4, Wärri A5, Grunau S1, Antonenkov VD6, Hiltunen JK7.
- Developmental biology.Dev Biol.2014 Jul 1;391(1):66-80. doi: 10.1016/j.ydbio.2014.03.022. Epub 2014 Apr 12.
- To understand the functional role of the peroxisomal membrane channel Pxmp2, mice with a targeted disruption of the Pxmp2 gene were generated. These mice were viable, grew and bred normally. However, Pxmp2(-/-) female mice were unable to nurse their pups. Lactating mammary gland epithelium displayed
- PMID 24726525
- Shikonin blocks migration and invasion of human breast cancer cells through inhibition of matrix metalloproteinase-9 activation.
- Jang SY1, Lee JK1, Jang EH1, Jeong SY2, Kim JH1.
- Oncology reports.Oncol Rep.2014 Jun;31(6):2827-33. doi: 10.3892/or.2014.3159. Epub 2014 Apr 25.
- Shikonin, a natural naphthoquinone isolated from a traditional Chinese medicinal herb, has been reported to promote tumor cell death. However, there are few reports concerning its effect on metastasis-related cell invasion and migration behavior. In the present study, we investigated the effect of s
- PMID 24789371
Japanese Journal
- Inhibitory effects of azole-type fungicides on interleukin-17 gene expression via retinoic acid receptor-related orphan receptors α and γ
- Kojima Hiroyuki,Muromoto Ryuta,Takahashi Miki,Takeuchi Shinji,Takeda Yukimasa,Jetten Anton M.,Matsuda Tadashi
- Toxicology and Applied Pharmacology 259(3), 338-345, 2012-03-15
- … Next, five azole-type fungicides, showing ROR inverse agonist activity, were tested on IL-17 mRNA expression in mouse T lymphoma EL4 cells treated with phorbol myristate acetate and ionomycin. …
- NAID 120004027239
- Interferon regulatory factor-4 activates IL-2 and IL-4 promoters in cooperation with c-Rel.
- Shindo Hisakazu,Yasui Kiyoshi,Yamamoto Kazuo,Honma Kiri,Yui Katsuyuki,Kohno Tomoko,Ma Yuhua,Chua Koon Jiew,Kubo Yoshinao,Aihara Hitoshi,Ito Takashi,Nagayasu Takeshi,Matsuyama Toshifumi,Hayashi Hideki
- Cytokine 56(3), 564-572, 2011-12
- … In T-cells, IRF-4 expression is induced by T-cell receptor (TCR) cross-linking or treatment with phorbol-12-myristate-13-acetate (PMA)/Ionomycin, and IRF-4 is thought to be a critical factor for various functions of T-cells. …
- NAID 120003659758
Related Links
- Isopropyl myristate is a synthetic oil widely used in the cosmetics and pharmaceutical industries as a lubricant, emollient, and as a non-toxic alternative for ...
- Isopropyl myristate is a chemical compound found in many skin care products that enhances their properties but also has potential side effects every ...
Related Pictures
★リンクテーブル★
[★]
- 英
- [[]]
- 同
- myristate
- 関
- [[]]
- 同
- myristate
[★]
- 英
- myristate
- 関
- ミリスチン酸
[★]
ホルボールミリステートアセテート、酢酸ミリスチン酸ホルボール
- 関
- phorbol 12-myristate 13-acetate、PMA、tetradecanoylphorbol acetate
[★]
ホルボールミリステートアセテート、酢酸ミリスチン酸ホルボール
- 関
- phorbol myristate acetate、PMA
[★]
ホルボールミリステイトアセテート
[★]