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Asem linoléat

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Struktur kimiya asem linoléat
Linoleic acid
Gambar
Gambar
Gambar
Jeneng IUPAC
(9Z,12Z)-octadeca-9,12-dienoic acid
Jeneng liya
cis,cis-9,12-octadecadienoic acid
C18:2 (Lipid numbers)
Identifikasi
Nomor CAS [60-33-3]
PubChem 5280450
KEGG C01595
ChEBI CHEBI:17351
SMILES CCCCC/C=C\C/C=C\CCCCCCCC(=O)O
InChI 1/C18H32O2/c1-2-3-4-5-6-7-8-9-10-11-12-13-14-15-16-17-18(19)20/h6-7,9-10H,2-5,8,11-17H2,1H3,(H,19,20)/b7-6-,10-9-
Réferènsi Baeilstein 1727101
Réferènsi Gmelin 57557
3DMet B00328
Sifat
Rumus kimia C18H32O2
Massa molar 280.45 g mol−1
Panampilan Colorless oil
Densitas 0.9 g/cm3[1]
Titik leleh

−12 °C (10 °F)[1]
−6.9 °C (19.6 °F)[2]
−5 °C (23 °F)[3]

Titik umob

229 °C (444 °F) at 16 mmHg[2]
230 °C (446 °F) at 21 mbar[3]
230 °C (446 °F) at 16 mmHg[1]

Kelarutan dalam air 0.139 mg/L[3]
Penetan uwab 16 Torr at 229 °C[butuh sitiran]
Bahaya
NFPA 704
1
2
0
 
Titik murub 112 °C (234 °F)[3]
Kejaba ditélakaké suwaliké, data ing ndhuwur kanggo
ing suhu lan tekanan standar (25°C, 100 kPa)

Sangkalan lan referensi

Asem linoléat minangka senyawa organik kanthi formula COOH (CH 2 ) 7 CH = CHCH 2 CH = CH (CH 2 ) 4 CH 3. Kaloro klompok alkena yaiku cis . Iki minangka asem lemak sing asring diarani 18: 2 (n-6) utawa 18: 2 cis -9,12 . Linoléat minangka uyah utawa ester saka asem iki. [4] Asem linoléat minangka asem lemak oméga-6 sing dipolietaturasi . Iki minangka lenga tanpa warna utawa putih sing méh ora larut ing banyu nanging larut ing akèh pelarut organik. Biasané kedadeyan ing alam minangka trigliserida (ester gliserin) lan ora kalebu asem lemak . [5] Iki minangka salah siji saka rong asem lemak penting kanggo manungsa, sing kudu ana ing pola mangan. [6] Tembung "linoleic" asalé saka basa Latin "flax" + oleum "linum Latin, nuduhaké kasunyatan manawa zat iki pisanan diisolasi karo lenga wiji rami.

Sejarah asem linoléat

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Ing taun 1844, F. Sacc, makarya ing laboratorium Justus von Liebig, ngisolasi asem linoléat saka lenga wiji rami. [7] [8] Ing taun 1886, K. Peters nemtokaké anané rong obligasi dobel. [9] Peran penting ing panganan manungsa ditemokaké dening GO Burr lan liyané ing taun 1930. [10] Struktur kimia kasebut ditemtokaké dening TP Hilditch lan liyané ing taun 1939, lan disintesis dening RA Raphael lan F. Sondheimer ing taun 1950. [11]

Peran asem linoléat

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Asem linoléat ing telung dhimènsi

Konsumsi asem linoléat iku penting banget kanggo kesehatan, amarga iku asem lemak penting. [12] Ing tikus, panganan sing kurang linoléat ( bentuk uyah asam) wis kabukten nggawé kulit sisik, rambut rontok, [13] lan lelara. [14]

Reaksi asem linoléat lan gunané

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Asem linoléat minangka komponèn lenga sing cepet garing, sing migunani kanggo cèt lenga lan varnis . Iki kerja kanthi ngedhuk labilitas saka kurva kelompok CH (-CH = CH-C H 2 -CH = CH-) menyang oksigén ing udhara. Tambahan oksigén nyebabaké ranté silang lan pembentukan film stabil. Pangurangan klompok asem karboksilat asem linoléat ngasilaké alkohol linoleil.[15] Asem linoléat minangka surfaktan kanthi konsentrasi misèl kritis 1,5 x 10 −4 M @ pH 7,5.

Asem linoléat dadi sansaya populer ing industri produk kecantikan amarga khasiat ing kulit. Panliten nuduhaké asem anti-inflamasi, ngurangi kukul, pancerah kulit lan sifat retènsi kelembapan nalika ditrapaké ing kulit. [16] [17] [18] [19]

Panganan sing ngandhung asem linoléat

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Asem linoléat kasedhiya ana akèh ing kembang saf, lenga kwaci, lenga jagung, lan kalebu luwih saka separo komposisi kanthi bobot. Saiki kasedhiya ing jumlah sedhengan kanggo lenga kedeleé, wijén, lan almon . [20] [21]

Paripustaka

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  1. ↑ a b c The Merck Index, 11th Edition, 5382
  2. ↑ a b William M. Haynes (2016). CRC Handbook of Chemistry and Physics (édhisi ka-97th). Boca Raton: CRC Press. kc. 3–338. ISBN 978-1-4987-5429-3.
  3. ↑ a b c d Cithakan:GESTIS
  4. ↑ "Fatty Acids". Cyber Lipid. Diarsip saka sing asli ing 28 October 2018. Dibukak ing 31 July 2017.
  5. ↑ Mattes, RD (2009). "Is there a fatty acid taste?". Annu. Rev. Nutr. 29: 305–27. doi:10.1146/annurev-nutr-080508-141108. PMC 2843518. PMID 19400700.
  6. ↑ Simopoulos, Artemis P. (2008). "The importance of the omega-6/omega-3 fatty acid ratio in cardiovascular disease and other chronic diseases". Experimental Biology and Medicine. 233 (6): 674–688. doi:10.3181/0711-mr-311. PMID 18408140.
  7. ↑ F. Sacc (1844) "Ueber das Leinöl, seine physicalischen und chemischen Eigenscharften und seine Oxydationsproducte".
  8. ↑ F. Sacc (1845): "Expériences sur les propriétés physiques et chimiques de l'huile de Lin".
  9. ↑ (1886), Monatsch., volume 7, pages 522-
  10. ↑ (1930: J Biol Chem, volume 86, pages 587-
  11. ↑ R. A. Raphael and Franz Sondheimer (1950): "The synthesis of long-chain aliphatic acids from acetylenic compounds.
  12. ↑ Whelan, Jay; Fritsche, Kevin (May 2013). "Linoleic Acid". Advances in Nutrition. 4 (3): 311–312. doi:10.3945/an.113.003772. PMC 3650500. PMID 23674797.
  13. ↑ "Pure linoleate deficiency in the rat: influence on growth, accumulation of n-6 polyunsaturates, and (1-14C) linoleate oxidation". J Lipid Res. 38 (4): 805–12. 1 April 1997. PMID 9144095. Diarsip saka sing asli ing 2007-02-28. Dibukak ing 2007-01-15.
  14. ↑ "Both (n-3) and (n-6) fatty acids stimulate wound healing in the rat intestinal epithelial cell line, IEC-6". Journal of Nutrition. 129 (10): 1791–8. 1 October 1999. doi:10.1093/jn/129.10.1791. PMID 10498749.
  15. ↑ Adkins, Homer; Gillespie, R. H. (1949). "Oleyl Alcohol". Organic Syntheses. 29: 80. doi:10.15227/orgsyn.029.0080.
  16. ↑ Diezel, W.E.; Schulz, E.; Skanks, M.; Heise, H. (1993). "Plant oils: Topical application and anti-inflammatory effects (croton oil test)". Dermatologische Monatsschrift. 179: 173.
  17. ↑ Letawe, C; Boone, M; Pierard, GE (March 1998). "Digital image analysis of the effect of topically applied linoleic acid on acne microcomedones". Clinical and Experimental Dermatology. 23 (2): 56–58. doi:10.1046/j.1365-2230.1998.00315.x. PMID 9692305.
  18. ↑ Ando, H; Ryu, A; Hashimoto, A; Oka, M; Ichihashi, M (March 1998). "Linoleic acid and α-linolenic acid lightens ultraviolet-induced hyperpigmentation of the skin". Archives of Dermatological Research. 290 (7): 375–381. doi:10.1007/s004030050320. PMID 9749992.
  19. ↑ Darmstadt, GL; Mao-Qiang, M; Chi, E; Saha, SK; Ziboh, VA; Black, RE; Santosham, M; Elias, PM (2002). "Impact of topical oils on the skin barrier: possible implications for neonatal health in developing countries". Acta Paediatrica. 91 (5): 546–554. CiteSeerX 10.1.1.475.1064. doi:10.1080/080352502753711678. PMID 12113324.
  20. ↑ "Nutrient Data Laboratory Home Page". USDA National Nutrient Database for Standard Reference, Release 20. U.S. Department of Agriculture, Agricultural Research Service. 2007. Diarsip saka sing asli ing 14 April 2016.
  21. ↑ Kaur, Narinder; Chugh, Vishal; Gupta, Anil K. (October 2014). "Essential fatty acids as functional components of foods- a review". Journal of Food Science and Technology. 51 (10): 2289–2303. doi:10.1007/s13197-012-0677-0. PMC 4190204. PMID 25328170.
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