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Ceramides (hydroxy)


  • Catalog #:1323

  • Scientific Name:Ceramides (hydroxy)

  • Common Name:Ceramides, mostly with hydroxy acyl groups

  • Empirical Formula:C36H71NO4 (2-hydroxystearoyl)
    Typical fatty acid content

  • SDS:View Safety Data Sheet

  • Data Sheet:View Data Sheet

  • Formula Weight:582 (2-hydroxystearoyl)

  • Unit:10 mg

  • Solvent:none

  • Source:natural

  • Purity:98+%

  • Analytical Methods:TLC, identity confirmed by MS

  • Natural Source:bovine spinal cord

  • Solubility:chloroform/methanol, 2:1; methanol

  • Physical Appearance:solid

  • Storage:-20℃

  • Composition:mostly hydroxy fatty acid side chain

  • Dry Ice:No

  • Hazardous:No


Application Notes:

神经酰胺是一种鞘氨醇的脂肪酸酰胺。本品含有以2-羟基脂肪酸(α -羟基脂肪酸)为主的神经酰胺。2-羟基脂肪酸神经酰胺在神经细胞和表皮细胞中尤为丰富。这些神经酰胺对表皮的渗透屏障功能和膜中的脂质组织很重要。2-羟化作用由脂肪酸2-羟化酶(FA2H或脂肪酸α -羟化酶)催化。神经酰胺是神经鞘磷脂、鞘糖脂、游离鞘糖苷和脂肪酸合成的前体。鞘氨醇可被磷酸化形成鞘氨醇-1-磷酸。神经酰胺的两种代谢物,磷酸鞘氨酸和葡萄糖酰神经酰胺,产生细胞增殖和其他细胞功能神经酰胺具有多种生物学效应,包括诱导细胞成熟、细胞周期阻滞、细胞晚期分化、细胞衰老和细胞死亡由于这些作用,神经酰胺已被研究用于癌症治疗,并提出了许多潜在的癌症治疗方法其他作用包括在线粒体中产生活性氧(随后是凋亡)和刺激某些蛋白的磷酸化(特别是丝裂原活化蛋白)。它还刺激一些蛋白质磷酸酶(特别是蛋白质磷酸酶2A),使其成为蛋白质活性的重要控制器。具有短侧链的神经酰胺很容易进入具有生物活性的细胞。侧链较长的神经酰胺如果先溶解在十二烷-异丙醇中,也会进入细胞。

Ceramide is a fatty acid amide of sphingosine. This product contains ceramides with mostly 2-hydroxy fatty acids (alphahydroxy fatty acids). 2-hydroxy fatty acid ceramides are especially abundant in nervous and epidermal cells. These ceramides are important for the permeability barrier function of epidermis and the lipid organization in membranes. The 2- hydroxylation is catalyzed by fatty acid 2-hydroxylase (FA2H or fatty acid alpha-hydroxylase). Ceramide functions as a precursor in the synthesis of sphingomyelin, glycosphingolipids, and of free sphingosine and fatty acids. The sphingosine can be phosphorylated to form sphingosine-1-phosphate. Two of ceramide’s metabolites, sphingosine-1-phosphate and glucosylceramide, produce cell proliferation and other cellular functions.1 Ceramide exerts numerous biological effects, including induction of cell maturation, cell cycle arrest, terminal cell differentiation, cell senescence, and cell death.2 Because of these effects ceramide has been investigated for its use in cancer treatment and many potential approaches to cancer therapy have been presented.3 Other effects include producing reactive oxygen in mitochondria (followed by apoptosis) and stimulating phosphorylation of certain proteins (especially mitogen activated protein). It also stimulates some protein phosphatases (especially protein phosphatase 2A) making it an important controller of protein activity. Ceramides with short side chains have been shown to enter easily into cells where they are biologically active. Ceramides with longer side chains also enter cells if dissolved in dodecane-isopropanol first.

1. J. M. Hauser, B. M. Buehrer, and R. M. Bell, Journal of Biological Chemistry  Vol. 269 pp. 6803, 1994
2. N. S. Radin, Biochemical Journal, Vol. 371 pp. 243-256, 2003
3. N. S. Radin, Bioorganic and Medicinal Chemistry, Vol. 11(10) pp. 2123-2142, 2003
4. Midori Yano, Etsu Kishida, Yuka Muneyuki, and Yasuo Masuzawa,  Journal of Lipid Research, Vol. 39 pp. 2091-2098, 1998