2-O-(β-D-galactopyranosyl)-glycerol | 3879-81-0

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 甘油脂
• 英文名称: 2-O-(β-D-galactopyranosyl)-glycerol
• 英文别名: 2-O-β-D-(galactopyranosyl)glycerol；2-O-β-D-galactosyl-glycerol；2-O-β-d-galactosylglycerol；(β,β'-dihydroxy-isopropyl)-β-D-galactopyranoside；(β,β'-Dihydroxy-isopropyl)-β-D-galactopyranosid；(2R,3R,4S,5R,6R)-2-[(1,3-dihydroxypropan-2-yl)oxy]-6-(hydroxymethyl)oxane-3,4,5-triol；(2R,3R,4S,5R,6R)-2-(1,3-dihydroxypropan-2-yloxy)-6-(hydroxymethyl)oxane-3,4,5-triol
• CAS: 3879-81-0
• 化学式: C₉H₁₈O₈
• 分子量: 254.237
• InChiKey: AQTKXCPRNZDOJU-QMGXLNLGSA-N

物化性质

• 熔点：
  126-127 °C(Solv: ethanol (64-17-5); methanol (67-56-1))
• 沸点：
  606.1±55.0 °C(Predicted)
• 密度：
  1.58±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  -3.5
• 重原子数：
  17
• 可旋转键数：
  5
• 环数：
  1.0
• sp3杂化的碳原子比例：
  1.0
• 拓扑面积：
  140
• 氢给体数：
  6
• 氢受体数：
  8

反应信息

• 作为反应物：
  描述：

  2-O-(β-D-galactopyranosyl)-glycerol 在 吡啶 、 Pseudomonas cepacia lipase 作用下， 反应 4.0h， 生成
  参考文献：
  名称：

  Bioactive glycoglycerolipid analogues: an expeditious enzymatic approach to mono- and diesters of 2-O-β-d-galactosylglycerol

  摘要：

  2-O-beta-D-Galactosylglycerol 1 was submitted to acylation using Pseudomonas cepacia or Candida antarctica lipases as catalysts and 2,2,2-trifluoroethyl esters of butanoic, hexanoic, octanoic or decanoic acid as acyl carriers. Taking advantage of the high diastereoselectivity and regioselectivity of the two enzymes, the 1-O-, 3-O-, 6'-O-acyl and the 1,6'-di-O-acylderivatives of 1 were obtained pure or in an appreciably enriched form. (C) 1998 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0957-4166(98)00207-9
• 作为产物：
  描述：

  beta-D-半乳糖五乙酸酯 在 palladium on activated charcoal 三氟化硼乙醚 、 氢气 、 sodium methylate 作用下， 以 甲醇 、 二氯甲烷 、 溶剂黄146 为溶剂， 反应 4.0h， 生成 2-O-(β-D-galactopyranosyl)-glycerol
  参考文献：
  名称：

  Synthesis of Glycosyl Glycerols and Related Glycolipids

  摘要：

  Several isomeric glycosyl glycerols were synthesized. Acetylated allyl glycosides of D-glucose and D-galactose were transformed into 1-O-(glycopyranosyl)-rac-glycerols in a three step procedure via the corresponding 2,3-epoxypropyl glycosides and the peracetylated glycosyl glycerols. Tetra-O-benzyl-D-glucose was glycosylated with 1,3-di-O-benzylglycerol to give the alpha-anomer preferentially. The 2-O-(tetra-O-acetyl-beta-glycopyranosyl)-sn-glycerols and 2-O-(beta-glycopyranosyl)-sn-glycerols of D-glucose, D-galactose and N-acetyl-D-glucosamine and the corresponding alpha-derivatives of D-mannose were synthesized by selective glycosylation methods from 1,3-di-O-benzylglycerol and 1,3-O-benzylideneglycerol, respectively, and activated sugar compounds followed by hydrogenolysis. After long chain acylation and selective deacetylation the 1,3-di-O-acyl-2-O-(beta-glycopyranosyl)-sn-glycerols of D-glucose, D-galactose and N-acetyl-D-glucosamine and the corresponding a-derivative of D-mannose were synthesized.

  DOI：

  10.1080/07328309808007465

文献信息

• THE CONFIGURATION OF GLYCOSIDIC LINKAGES IN OLIGOSACCHARIDES: II. BY DEGRADATION OF REDUCING DISACCHARIDES TO 2-<i>O</i>-GLYCOSYL-GLYCEROLS
  作者：A. J. Charlson、P. A. J. Gorin、A. S. Perlin

  DOI：10.1139/v56-234

  日期：1956.12.1

  degraded by employing a series of oxidations and reductions to yield 2-O-glycosyl-glycerols, configurations of which are assigned according to Hudson's definition. Maltose, for example, treated with 2 moles of lead tetraacetate gives 2-O-α-D-glucopyranosyl-D-erythrose; the latter is reduced to the corresponding alcohol, which is oxidized in turn with 1 mole of lead tetraacetate to give 2-O-α-D-gluco

  还原性吡喃己糖二糖通过一系列氧化和还原作用降解，产生 2-O-糖基-甘油，其构型根据 Hudson 的定义进行分配。例如，麦芽糖用 2 摩尔四乙酸铅处理得到 2-O-α-D-吡喃葡萄糖基-D-赤藓糖；后者被还原为相应的醇，依次用 1 摩尔四乙酸铅氧化生成 2-O-α-D-吡喃葡萄糖基-L-甘油醛，第二次还原生成 2-O-α-D-吡喃葡萄糖基-甘油。纤维二糖通过相同的反应序列转化为 2-O-β-D-吡喃葡萄糖基甘油。其他含有 D-吡喃葡萄糖非还原性末端单元的还原性二糖也可以被降解以得到这些异头甘油衍生物中的一种或另一种，其身份确定了原始二糖中糖苷键的构型。这对异头 2-OD-吡喃半乳糖基甘油由天然存在的 α-异头物提供，产物 o...
• Anti-tumor-promoting activity of simple models of galactoglycerolipids with branched and unsaturated acyl chains
  作者：Diego Colombo、Laura Franchini、Lucio Toma、Fiamma Ronchetti、Nami Nakabe、Takako Konoshima、Hoyoku Nishino、Harukuni Tokuda

  DOI：10.1016/j.ejmech.2004.09.021

  日期：2005.1

  l skeleton, were tested for their anti-tumor-promoting activity using a short-term in vitro assay for Epstein-Barr virus early antigen (EBV-EA) activation. All these compounds were more active than their linear or saturated reference compounds in inhibiting the EBV activation promoted by the tumor promoter 12-O-tetradecanoylphorbol-13-acetate (TPA), the diester 1-O-(4-methylpentanoyl)-2-O-[6-O-(4-

  测试了六个新的半乳糖甘油类似物，其中一个或两个4-甲基戊酰基或反-2-丁烯酰基与2-O-β-D-半乳糖基甘油骨架相连，并通过短期测试了它们的抗肿瘤活性EB病毒早期抗原（EBV-EA）激活的体外测定。所有这些化合物在抑制肿瘤启动子12-O-十四烷酰phorbol-13-乙酸酯（TPA），二酯1-O-（4-甲基戊酰）-2-促进的EBV活化方面均比其线性或饱和参照化合物更有活性。直到现在测试的O- [6-O-（4-甲基戊酰基）-β-D-吡喃半乳糖基] -sn-甘油产生最活跃的糖脂类类似物。在体内两阶段致癌性试验中测试时，四种化合物（三种丁烯酸酯和一种4-甲基戊酸酯）还表现出对小鼠皮肤肿瘤促进作用的抑制作用。
• THE CONFIGURATION OF GLYCOSIDIC LINKAGES IN OLIGOSACCHARIDES: IV. FURTHER DEGRADATIONS OF REDUCING DISACCHARIDES TO 2-<i>O</i>-GLYCOSYL-GLYCEROLS
  作者：A. J. Charlson、P. A. J. Gorin、A. S. Perlin

  DOI：10.1139/v57-054

  日期：1957.4.1

  The configuration of glycosidic linkages in a number of reducing disaccharides has been determined by converting each compound to the corresponding 2-O-glycosyl-glycerol, the configuration of which was readily established. Compounds examined include 3-O-β-D-galactopyranosyl-D-galactose, 3-O-α-D-galactopyranosyl-L-arabinose, 3-O-β-D-arabopyranosyl-L-arabinose, 2-O-β-D-xylopyranosyl-L-arabinose, 3-O-α-D-xylopyranosyl-L-arabinose, and 4-O-β-D-xylopyranosyl-D-xylose, all of which were derived by partial hydrolysis of polysaccharides. 2-O-α-L-Arabopyranosyl-glycerol has been synthesized via the Koenigs-Knorr condensation.

  一些还原二糖的糖苷键的构型已经通过将每个化合物转化为相应的2-O-糖基-甘油醇来确定，其构型很容易确定。检查的化合物包括3-O-β-D-半乳糖苷-D-半乳糖、3-O-α-D-半乳糖苷-L-阿拉伯糖、3-O-β-D-阿拉伯糖苷-L-阿拉伯糖、2-O-β-D-木糖苷-L-阿拉伯糖、3-O-α-D-木糖苷-L-阿拉伯糖和4-O-β-D-木糖苷-D-木糖，所有这些化合物都是通过部分水解多糖得到的。2-O-α-L-阿拉伯糖苷基-甘油醇已通过Koenigs-Knorr缩合合成。
• Nouvelles utilisations de derivés du glycerol, notamment dans le domaine cosmétique
  申请人：AGRO INDUSTRIE RECHERCHES ET DEVELOPPEMENTS (A.R.D.)

  公开号：EP1733731A1

  公开（公告）日：2006-12-20

  La présente invention concerne l'utilisation d'au moins un composé répondant à la formule (I) suivante : dans laquelle R1 représente H ou un groupe acyle, R2 représente notamment H ou un groupe acyle, et R3 représente H ou un groupe de formule suivante (C) : dans laquelle R6 représente notamment un atome d'hydrogène ou un groupe acyle, et R7 représente notamment un atome d'hydrogène ou un groupe acyle, pour la préparation d'une composition cosmétique, d'une composition pharmaceutique destinée au traitement des cancers n'impliquant pas le virus EBV, notamment destinée au traitement des mélanomes, ou destinée au traitement des processus inflammatoires de la sphère buccale, ou d'une composition nutraceutique,

  本发明涉及至少一种与下式（I）相对应的化合物的用途： 其中 R1 代表 H 或酰基，R2 尤其代表 H 或酰基，R3 代表 H 或下式（C）的基团： 其中 R6 特别代表氢原子或酰基，R7 特别代表氢原子或酰基、 用于制备化妆品组合物、用于治疗不涉及 EBV 病毒的癌症（尤其是用于治疗黑 色素瘤）或用于治疗口腔炎症过程的药物组合物或营养保健组合物、
• Probiotic treatment of skin diseases, disorders, and infections: formulations, methods and systems
  申请人：Baum Marc M.

  公开号：US10238597B2

  公开（公告）日：2019-03-26

  The present invention teaches compositions, methods and kits for treating skin conditions, including dandruff. In various embodiments, the compositions include an effective amount of one or more probiotic microorganism of vaginal origin and/or a fraction thereof and/or a component of the metabolome for preventing and/or treating skin disorders of the scalp.

  本发明教导用于治疗包括头皮屑在内的皮肤病的组合物、方法和试剂盒。在各种实施方案中，组合物包括有效量的一种或多种阴道源益生菌微生物和/或其组分和/或代谢组成分，用于预防和/或治疗头皮的皮肤疾病。