(2R,3S,4R,5S)-2,3,4,5-Tetrahydroxy-hexanedioic acid diethyl ester | 15909-67-8

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: (2R,3S,4R,5S)-2,3,4,5-Tetrahydroxy-hexanedioic acid diethyl ester
• 英文别名: diethyl mucate；diethyl (2S,3R,4S,5R)-2,3,4,5-tetrahydroxyhexanedioate
• CAS: 15909-67-8
• 化学式: C₁₀H₁₈O₈
• 分子量: 266.248
• InChiKey: VYFOOXBIRRKSIH-SOSBWXJGSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -1.7
• 重原子数：
  18
• 可旋转键数：
  9
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.8
• 拓扑面积：
  134
• 氢给体数：
  4
• 氢受体数：
  8

安全信息

• 海关编码：
  2918199090

反应信息

• 作为反应物：
  描述：

  (2R,3S,4R,5S)-2,3,4,5-Tetrahydroxy-hexanedioic acid diethyl ester 在 乙醇 、 亚硝酸 、 一水合肼 作用下， 生成 dimethyl galactarate
  参考文献：
  名称：

  Curtius, Journal fur praktische Chemie (Leipzig 1954), 1917, vol. <2> 95, p. 211

  摘要：

  DOI：
• 作为产物：
  描述：

  乙醇 、 alkaline earth salt of/the/ methylsulfuric acid 在 盐酸 作用下， 生成 (2R,3S,4R,5S)-2,3,4,5-Tetrahydroxy-hexanedioic acid diethyl ester
  参考文献：
  名称：

  Skraup, Monatshefte fur Chemie, 1893, vol. 14, p. 475

  摘要：

  DOI：

文献信息

• H ₂ ‐Free Re‐Based Catalytic Dehydroxylation of Aldaric Acid to Muconic and Adipic Acid Esters
  作者：Brigita Hočevar、Anže Prašnikar、Matej Huš、Miha Grilc、Blaž Likozar

  DOI：10.1002/anie.202010035

  日期：2021.1.18

  As one of the most demanded dicarboxylic acids, adipic acid can be directly produced from renewable sources. Hexoses from (hemi)cellulose are oxidized to aldaric acids and subsequently catalytically dehydroxylated. Hitherto performed homogeneously, we present the first heterogeneous catalytic process for converting an aldaric acid into muconic and adipic acid. The contribution of leached Re from the

  作为最需要的二元羧酸之一，己二酸可以直接由可再生资源生产。来自（半）纤维素的己糖被氧化成醛酸，随后被催化脱羟基。迄今为止，均相地进行，我们提出了将醛酸转化成粘康酸和己二酸的第一个非均相催化方法。还通过热过滤试验研究了固体预还原催化剂中浸出的稀土元素的贡献，发现其对脱羟基没有活性。腐蚀性或危险性（HBr / H 2）避免使用试剂，并在惰性气氛中使用简单的醇和固体Re / C催化剂。在120°C下，羧基被酯化保护，这可防止在没有水或酸性位点的情况下内酯化。脱羟基和部分氢化产生单己酸（93％）。为了使己二酸完全氢化，需要高出16％的活化势垒。
• Effects of a New Selective Estrogen Receptor Modulator (MDL 103,323) on Cancellous and Cortical Bone in Ovariectomized Ewes: A Biochemical, Histomorphometric, and Densitometric Study
  作者：Pascale Chavassieux、Patrick Garnero、Francois Duboeuf、Philippe Vergnaud、Francoise Brunner-Ferber、Pierre D. Delmas、Pierre J. Meunier

  DOI：10.1359/jbmr.2001.16.1.89

  日期：——

  The aims of this study performed in ewes were: (1) to confirm in this animal model the effects on bone of ovariectomy (OVX) alone or associated with Lentaron (L), a potent peripheral aromatase inhibitor, used to amplify the effects of OVX and (2) to evaluate the effects of a new selective estrogen receptor modulator (SERM; MDL 103,323) on bone remodeling. Thirty‐nine old ewes were divided into five groups: sham (n = 7); OVX (n = 8); OVX + L (n = 8); OVX + L + MDL; 0.1 mg/kg per day (n = 8); and OVX + L + MDL 1 mg/kg per day (n = 8). The animals were treated for 6 months. Biochemical markers of bone turnover (urinary excretion of type 1 collagen C‐telopeptide [CTX], serum osteocalcin [OC], and bone alkaline phosphatase [BAP]) were measured each month. Bone biopsy specimens were taken at the beginning and after death at the end of the experiment. Bone mineral density (BMD) was measured by dual‐energy X‐ray absorptiometry (DXA) on the lumbar spine and femur. OVX induced a significant increase in biochemical markers. This effect was the highest after 3 months for CTX (+156% vs. sham) and after 4 months for OC and BAP (+74% and +53% vs. sham, respectively). L tended to amplify the effect of OVX on OC and BAP. OVX induced significant increases in the porosity, eroded, and osteoid surfaces in cortical bone but no effect was observed in cancellous bone. MDL treatment reduced the bone turnover as assessed by bone markers, which returned to sham levels as well as histomorphometry both in cortical and in cancellous bone. Cancellous osteoid thickness decreased by 27% (p < 0.05), mineralizing perimeter by 81% (p < 0.05), and activation frequency by 84% (p < 0.02) versus OVX + L. Femoral and spinal BMD were increased by MDL and tended to return to the sham values. The effects of OVX on bone turnover were different on cortical and cancellous bone. These effects on cortical bone were reflected by changes in biochemical markers. MDL markedly reduces bone turnover and increases BMD suggesting that this new agent may prevent postmenopausal bone loss.

  本研究在母羊中进行，旨在：(1) 在这一动物模型中确认单独或联合使用强效外周芳香化酶抑制剂Lentaron（L）的卵巢切除术（OVX）对骨骼的影响，以增强OVX的效果；(2) 评估一种新的选择性雌激素受体调节剂（SERM；MDL 103,323）对骨重建的影响。研究共纳入39只老母羊，分为五组：假手术组（n = 7）；OVX组（n = 8）；OVX + L组（n = 8）；OVX + L + MDL 0.1 mg/kg每日至（n = 8）；OVX + L + MDL 1 mg/kg每日至（n = 8）。动物治疗持续了6个月。每月测量骨代谢的生化标记物（尿中1型胶原C末端肽[CTX]、血清骨钙素[OC]和骨碱性磷酸酶[BAP]）。在实验开始时及结束时对死亡后的骨活检标本进行取样。通过双能X射线吸收法（DXA）测量腰椎和股骨的骨矿密度（BMD）。OVX显著提高了生化标记物的水平。这一效应在3个月后CTX达到最高值（+156%对比假手术组），在4个月后OC和BAP分别增加了74%和53%。L倾向于增强OVX对OC和BAP的影响。OVX使皮质骨的孔隙度、侵蚀面和骨样面显著增加，但海绵骨未观察到影响。MDL治疗降低了骨代谢，生化标记物恢复至假手术组水平，组织形态学分析显示皮质和海绵骨均如此。海绵骨骨样厚度减少了27%（p < 0.05），矿化边缘减少了81%（p < 0.05），激活频率减少了84%（p < 0.02），相较于OVX + L组。MDL使股骨和脊柱的BMD增加，并趋向恢复至假手术组水平。OVX对骨代谢的影响在皮质骨和海绵骨上有所不同。这些对皮质骨的影响体现在生化标记物的变化上。MDL显著降低了骨代谢并增加了BMD，提示该新剂可能预防绝经后骨质流失。
• [EN] CHEMICAL PROCESS TO CONVERT MUCIC ACID TO ADIPIC ACID<br/>[FR] PROCÉDÉ CHIMIQUE POUR CONVERTIR L'ACIDE MUCIQUE EN ACIDE ADIPIQUE
  申请人：AGENCY SCIENCE TECH & RES

  公开号：WO2015084265A1

  公开（公告）日：2015-06-11

  The present invention provides a method of synthesizing an ester of a saturated carboxylic acid from a saturated polyhydroxycarboxylic acid by performing a deoxydehydration reaction and a hydrogen transfer reaction.

  本发明提供了一种从饱和多羟基羧酸通过进行脱氧脱水反应和氢转移反应合成饱和羧酸酯的方法。
• Pyrone Synthesis from Renewable Sources: Easy Preparation of 3-Acetoxy-2-oxo-2<i>H</i>-pyran-6-carboxylic Salts and their Derivatives as 3-Hydroxy-2<i>H</i>-pyran-2-one from C6 Aldaric Acids
  作者：Gabriella Leonardi、Jiemeng Li、Grazia Isa C. Righetti、Ada M. Truscello、Cristian Gambarotti、Giancarlo Terraneo、Attilio Citterio、Roberto Sebastiano

  DOI：10.1002/ejoc.201901427

  日期：2020.1.16

  different pH conditions to convert mucic acid and glucaric acid salts into the 3‐acetoxy‐2‐oxo‐2 H ‐pyran‐6‐carboxylic acid salts and their derivatives. The salts, in the presence of hydrochloric acid, are quantitatively converted to the corresponding 3‐hydroxy‐2‐oxo‐2 H ‐pyran‐6‐carboxylic acid, which afforded 3‐hydroxy‐2 H ‐pyran‐2‐one in very high yield by further thermal decarboxylation. Crystal

  2-吡喃酮是几种天然产物中存在的化合物，是有机合成中间体制备中有趣的组成部分。由于这些原因，已经开发了许多不同的制备方案用于吡喃酮部分的合成。在这项工作中，已经研究了一种从C6醛酸开始合成这些化合物的绿色方法。这些产品是一类有趣且用途广泛的多功能C6单元，来自可再生资源。在本文中，我们报告了一种基于绿色工艺的方法，该方法基于在不同pH条件下与乙酸酐反应，将粘液酸和葡糖二酸盐转化为3-乙酰氧基-2-氧代-2 H-吡喃-6-羧酸盐及其盐类。衍生品。这些盐在盐酸的存在下，将其定量转化为相应的3-羟基-2-氧代-2-H-吡喃-6-羧酸，通过进一步的热脱羧反应，可以非常高的产率获得3-羟基-2H-吡喃-2-一。报道了五元环内酯中间体的晶体结构。
• [EN] ELASTOMER COMPOSITIONS COMPRISING AN ADDUCT BETWEEN AN SP2 HYBRIDIZED CARBON ALLOTROPE AND A DICARBOXYLIC ACID DERIVATIVE<br/>[FR] COMPOSITIONS ÉLASTOMÈRES COMPRENANT UN PRODUIT D'ADDITION ENTRE UN ALLOTROPE CARBONÉ HYBRIDÉ TYPE SP2 ET UN DÉRIVÉ D'ACIDE DICARBOXYLIQUE
  申请人：PIRELLI

  公开号：WO2020222103A1

  公开（公告）日：2020-11-05

  The present invention relates to elastomer compositions comprising adducts between compounds of formula (I) preferably derived from natural sources such as mucic, pyromucic, glucaric, glycaric, galactaric, muconic acid and/or linear derivatives thereof containing ester or amide groups and/or cyclic derivatives thereof with heteroatoms in the ring, such as oxygen or nitrogen, and carbon allotropes in which the carbon is sp2 hybridized, such as for example carbon nanotubes, graphene or nanographites, carbon black.

  本发明涉及弹性体组合物，其中包括化合物的加合物，该化合物的化学式为(I)，最好来源于天然来源，如粘液酸、焦粘液酸、葡萄糖酸、甘氨酸、半乳糖酸、默康酸和/或其含有酯或酰胺基团和/或其环状衍生物的线性衍生物，其中环中含有氧或氮等杂原子，以及碳异构体，其中碳是sp2杂化的，例如碳纳米管、石墨烯或纳米石墨、碳黑。