(+)-osbeckic acid | 112923-64-5

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 呋喃
• 英文名称: (+)-osbeckic acid
• 英文别名: 5-[(S)-carboxy(hydroxy)methyl]furan-2-carboxylic acid
• CAS: 112923-64-5
• 化学式: C₇H₆O₆
• 分子量: 186.121
• InChiKey: UAFTYLJFMASQBP-YFKPBYRVSA-N

物化性质

• 沸点：
  430.4±45.0 °C(Predicted)
• 密度：
  1.685±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  -0.2
• 重原子数：
  13
• 可旋转键数：
  3
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.14
• 拓扑面积：
  108
• 氢给体数：
  3
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  (+)-osbeckic acid 以 吡啶 、 甲醇 为溶剂， 生成 5-((S)-Acetoxy-methoxycarbonyl-methyl)-furan-2-carboxylic acid methyl ester
  参考文献：
  名称：

  Su, Jeng-De; Osawa, Toshihiko; Kawakishi, Shunro, Agricultural and Biological Chemistry, 1987, vol. 51, # 12, p. 3449 - 3450

  摘要：

  DOI：
• 作为产物：
  描述：

  dimethyl 2,6-anhydro-D-glycero-L-manno-heptarate 在 吡啶 、 aluminum oxide 、 Amberlite IR-120 (H⁺-form) 、 lutidine 、 硫酸 、 三氟乙酸 作用下， 以 氯仿 、 水 为溶剂， 反应 13.5h， 生成 (+)-osbeckic acid
  参考文献：
  名称：

  (−)-Daucic acid: Proof of d-lyxo configuration, synthesis of its d-ribo, d-xylo, l-arabino and l-lyxo analogs, and biosynthetic implications

  摘要：

  The dimethyl esters of the 2,6-anhydro-3-deoxy-hept-2-enaric acids with D-xylo, D-lyxo, L-arabino, L-lyxo- and D-ribo-configuration were synthesized from D-galactose and D-mannose, respectively, and further characterized by their di-O-acetyl and di-O-benzoyl derivatives. Comparison of their physical data with those of Daucus carota derived products revealed (-)-daucic acid to have D-lyxo-configuration 46 rather than the previously assigned D-xylo stereochemistry 1. Dimethyl daucate 43 could be converted by acid-induced ring contraction and dehydration into naturally occurring (+)-osbeckic acid 47, thereby proving its (S)-configuration. Configurational identity in the pyranoid rings of (-)-daucic acid and KDO, together with available biosynthetic evidence on chelidonic acid 4, a leaf closing factor, suggests a joint, KDO 8-P-based pathway for their biosynthesis in plants. (C) 2003 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetasy.2003.10.007

文献信息

• (−)-Daucic Acid: Revision of Configuration, Synthesis, and Biosynthetic Implications
  作者：Frieder W. Lichtenthaler、Katsumi Nakamura、Jürgen Klotz

  DOI：10.1002/anie.200352718

  日期：2003.12.8
• Inhibitory Effects of Phenylpropanoid Derivatives from <i>Oenanthe javanica</i> on Antigen-Stimulated Degranulation in RBL-2H3 Cells
  作者：Toshihiro Murata、Tatsuo Katagiri、Yoshinobu Ishikawa、Mizuki Abe、Emi Takahashi、Ruka Iwahana、Yuko Sakamoto、Kenroh Sasaki

  DOI：10.1021/acs.jnatprod.8b01054

  日期：2019.6.28

  Two diacyldaucic acids (1 and 2), an alpha,beta-unsaturated gamma-lactone-type lignan (3) and its derivatives (4-6), and 12 known compounds were isolated from a traditional East Asian vegetable, Oenanthe javanica. The absolute configuration of 1 was validated by obtaining (+)-osbeckic acid through acid hydrolysis. The absolute configurations of 3-5 were determined by comparing their experimental and computed ECD data. The conclusion was supported by applying the phenylglycine methyl ester method to 3. Compound 6 was obtained as an interconverting mixture of isomers in a 3:1 trans-cis ratio. Several water-soluble components (1, 3, and 6) showed concentration-dependent inhibitory effects on antigen-stimulated degranulation in RBL-2H3 cells without producing any direct cytotoxicity against RBL-2H3 or HeLa cells.
• SU, JENG-DE;OSAWA, TOSHIHIKO;KAWAKISHI, SHUNRO;NAMIKI, MITSUO, AGR. AND BIOL. CHEM., 51,(1987) N 12, 3449-3450
  作者：SU, JENG-DE、OSAWA, TOSHIHIKO、KAWAKISHI, SHUNRO、NAMIKI, MITSUO

  DOI：——

  日期：——
• (−)-Daucic acid: Proof of d-lyxo configuration, synthesis of its d-ribo, d-xylo, l-arabino and l-lyxo analogs, and biosynthetic implications
  作者：Frieder W. Lichtenthaler、Jürgen Klotz、Katsumi Nakamura

  DOI：10.1016/j.tetasy.2003.10.007

  日期：2003.12

  The dimethyl esters of the 2,6-anhydro-3-deoxy-hept-2-enaric acids with D-xylo, D-lyxo, L-arabino, L-lyxo- and D-ribo-configuration were synthesized from D-galactose and D-mannose, respectively, and further characterized by their di-O-acetyl and di-O-benzoyl derivatives. Comparison of their physical data with those of Daucus carota derived products revealed (-)-daucic acid to have D-lyxo-configuration 46 rather than the previously assigned D-xylo stereochemistry 1. Dimethyl daucate 43 could be converted by acid-induced ring contraction and dehydration into naturally occurring (+)-osbeckic acid 47, thereby proving its (S)-configuration. Configurational identity in the pyranoid rings of (-)-daucic acid and KDO, together with available biosynthetic evidence on chelidonic acid 4, a leaf closing factor, suggests a joint, KDO 8-P-based pathway for their biosynthesis in plants. (C) 2003 Elsevier Ltd. All rights reserved.
• Su, Jeng-De; Osawa, Toshihiko; Kawakishi, Shunro, Agricultural and Biological Chemistry, 1987, vol. 51, # 12, p. 3449 - 3450
  作者：Su, Jeng-De、Osawa, Toshihiko、Kawakishi, Shunro、Namiki, Mitsuo

  DOI：——

  日期：——