N-(2-hydroxystearoyl)phytosphingosine | 212070-45-6

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 鞘脂
• 英文名称: N-(2-hydroxystearoyl)phytosphingosine
• 英文别名: 2-hydroxy-N-[(2S,3S,4R)-1,3,4-trihydroxyoctadecan-2-yl]octadecanamide；(2S,3S,4R)-2-(2'-hydroxyoctadecanoylamino)-1,3,4-octadecantriol；N-stearoyl-2-hydroxy-D-erythro-phytosphingosine；N-(α-hydroxyoctadecanoyl)phytosphingosine；Cer (t18:0/18:0(OH))；N-(2-hydroxyoctadecanoyl)-hydroxysphinganine
• CAS: 212070-45-6
• 化学式: C₃₆H₇₃NO₅
• 分子量: 599.979
• InChiKey: BBAFBDLICMHBNU-MFZOPHKMSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  12.6
• 重原子数：
  42
• 可旋转键数：
  33
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.97
• 拓扑面积：
  110
• 氢给体数：
  5
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  N-(2-hydroxystearoyl)phytosphingosine 生成 (2S,3S,4R)-2-[(2'R)-2'-hydroxyoctadecanoylamino]-1,3,4-octadecantriol 、 (2S,3S,4R)-2-[(2'S)-2'-hydroxyoctadecanoylamino]-1,3,4-octadecantriol
  参考文献：
  名称：

  Polymorphism of ceramide 6: a vibrational spectroscopic and X-ray powder diffraction investigation of the diastereomers of N-(α-hydroxyoctadecanoyl)-phytosphingosine

  摘要：

  A preparative chromatographic method was developed for the quantitative isolation of the diastereomers of synthetic N-(alpha-hydroxyoctadecanoyl)-phytosphingosine (DL-CER6). The (L)- and the (D)-compound were studied each by means X-ray powder diffraction, FT-Raman and FT-IR spectroscopy. The diastereomers exhibit different thermotropic polymorphism. Three lamellar crystalline and a lamellar liquid crystalline phase were found for L-CER6. The natural occurring D-CER6 forms an La phase with a larger repeating distance than the L-CER6. The two lamellar crystalline phases of the D-compound have a significant larger dimension than those of the L-compound. The addition of water lowers the phase transition temperatures but does not induce structural changes such as incorporation into the lamellar sheets. (C) 2004 Elsevier Ireland Ltd. All rights reserved.

  DOI：

  10.1016/j.chemphyslip.2004.09.015
• 作为产物：
  描述：

  N-(2-acetoxy-octadecanoyl) phytosphingosine 、 sodium hydroxide 以 乙醇 为溶剂， 反应 2.5h， 生成 N-(2-hydroxystearoyl)phytosphingosine
  参考文献：
  名称：

  Selective N-acylation of amino alcohols

  摘要：

  本发明提供了一种高效的制备N-酰基氨基醇的方法，该方法通过将有机酸或其盐与烷基磺酰氯或烷基苯磺酰氯在有机溶剂和有机碱的存在下反应，选择性地酰化氨基醇的游离胺，形成相应的混合酐，然后将混合酐与氨基醇或其盐反应，形成相应的N-酰基氨基醇。

  公开号：

  US05631356A1

文献信息

• OIL-IN-WATER EMULSIFIED COSMETIC COMPOSITION
  申请人：YAMAMOTO Yumiko

  公开号：US20100311836A1

  公开（公告）日：2010-12-09

  The present invention relates to an oil-in-water emulsified cosmetic composition, which contains an emulsion having (A) a sphingosine represented by formula (1), (B) an acid compound selected from inorganic acids and organic acids having 5 or less carbon atoms, and (C) a ceramide represented by formula (2); and another emulsion having (D) an oil component selected from polar oils and hydrocarbon oils, and (E) a surfactant. (wherein, R 1 represents a hydrocarbon group which may have a substituent; Y represents methylene, methine or O; X 1 , X 2 and X 3 each represent H, OH or acetoxy group; X 4 represents H, acetyl group or the like; R 2 and R 3 each represents H, OH or the like; R represents H, amidino group or the like; and a stands for 2 or 3) (wherein, R 7 represents a hydrocarbon group which may have a substituent, or H; Z represents methylene, methine or O; X 5 , X 6 and X 7 each represent H, OH or acetoxy group; X 4 represents H, acetyl group or the like; R 8 and R 9 each represent H, OH or the like; R 10 represents a hydrocarbon group which may have a substituent; and R 11 represents H or a hydrocarbon group which may have a substituent). The oil-in-water emulsified cosmetic composition contains a ceramide and is excellent in emulsion stability.
• EMULSIFIED COMPOSITION
  申请人：Orita Masanori

  公开号：US20120108661A1

  公开（公告）日：2012-05-03

  The emulsion composition of the present invention contains (A) 0.001 to 10 wt. % of an organic compound having two or more hydroxyl groups, an inorganic value of 220 to 450, and an organic value of 300 to 1,000; (B) 0.001 to 10 wt. % of an organic compound having one hydroxyl group, an inorganic value of 100 to 200, and an organic value of 280 to 700; (C) 0.001 to 10 wt. % of a compound represented by formula (2): wherein R 1 is a C4 to C30 hydrocarbon group; Z is a methylene group, a methine group, or an oxygen atom; X 1 , X 2 , X 3 is a hydrogen atom, a hydroxyl group, or an acetoxy group; X 4 is a hydrogen atom, an acetyl group, or a glyceryl group; each of R 2 and R 3 a hydrogen atom, a hydroxyl group, a hydroxymethyl group, or an acetoxymethyl group; R 4 is a C5 to C60 hydrocarbon group; and R 5 is a hydrogen atom or a hydrocarbon group containing 1 to 30 carbon atoms in total; (D) 0.00012 to 10 wt. % of at least one compound selected from the group consisting of a nonionic surfactant having a polyoxyethylene group and an HLB of 10 or higher, an ionic surfactant, and a sphingosine salt; (E) 0.003 to 15 wt. % of at least one compound selected from the group consisting of a sugar alcohol selected from the group consisting of erythritol, threitol, xylitol, and mannitol, a disaccharide, and a trisaccharide; and (F) water.
• COSMETIC
  申请人：Yamamoto Yumiko

  公开号：US20130303483A1

  公开（公告）日：2013-11-14

  A cosmetic comprising the following components (A), (B), (C) and (D): (A) 0.001 to 50% by weight of an organic acid represented by a general formula (1), wherein R 1 denotes a residue derived from a natural sterin having one hydroxy group or a hydrogenated product thereof, or a residue derived from bile acid in which the hydroxyl hydrogen atom is removed; R 2 denotes a divalent hydrocarbon group having 1 to 24 carbon atoms; and M denotes a hydrogen atom, an alkali metal, an alkaline earth metal, ammonium, alkanolammonium having 2 to 9 carbon atoms in total, alkylammonium or alkenylammonium having 1 to 22 carbon atoms in total, a pyridinium substituted with an alkyl group or an alkenyl group having 1 to 18 carbon atoms, or a basic amino acid; (B) 0.001 to 20% by weight of a base; (C) 0.0001 to 50% by weight of a ceramide; and (D) water, and comprising, as a component (E), an acid other than the component (A) in a content satisfying a relationship: 0≦(E)/(A)<0.2, and having pH of 6 to 11.
• VESICLE COMPOSITION
  申请人：Yamamoto Yumiko

  公开号：US20140018443A1

  公开（公告）日：2014-01-16

  The present invention is to provide a vesicle composition comprising the following components (A), (B) and (C): (A) 0.0001 to 20 mass % of an organic acid represented by general formula (1): wherein R 1 represents a natural sterin having a single hydroxy group or a hydrogenated product thereof or a residue which remains after a hydrogen atom is removed from the hydroxy group of bile acid, R 2 represents a divalent hydrocarbon group having 1 to 24 carbon atoms, M represents a hydrogen atom, an alkali metal, an alkali earth metal, ammonium, an alkanolammonium having 2 to 9 carbon atoms in total, an alkylammonium or alkenylammonium having 1 to 22 carbon atoms in total, pyridinium substituted with an alkyl group or alkenyl group having 1 to 18 carbon atoms or a basic amino acid, (B) 0.0001 to 10 mass % of a sphingosine, and (C) water, and having a pH of 2 to 11.
• Emulsion Composition
  申请人：Kaizu Kazuhiro

  公开号：US20140194522A1

  公开（公告）日：2014-07-10

  Provided is an emulsion composition comprising the following ingredients (A), (B), (C), (D), (E), and (F): (A) glyceryl monofatty acid ester derived from a linear-chain fatty acid having 10 to 24 carbon atoms; (B) a higher alcohol having 10 to 24 carbon atoms; (C) a ceramide; (D) an anionic surfactant; (E) a polar oil selected from branched fatty acid esters having an IOB of from 0.2 to 0.85 and having a hydroxyl group or an amino group; and (F) water, wherein the mass ratio of the total content of ingredients (A), (B), and (C) and ingredient (D) in terms of acid to the content of ingredient (E), ((A)+(B)+(C)+(D))/(E), is from 1.2 to 25.