5-keto-L-galactonic acid | 6812-01-7

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 羟基酸及其衍生物
• 英文名称: 5-keto-L-galactonic acid
• 英文别名: D-arabino-[5]hexulosonic acid；D-arabino-[5]Hexulosonsaeure；D-arabino-5-hexulosonic acid；arabino-5-hexulosonic acid；D-tagaturonic acid；(2S,3R,4S)-2,3,4,6-tetrahydroxy-5-oxohexanoic acid
• CAS: 6812-01-7
• 化学式: C₆H₁₀O₇
• 分子量: 194.141
• InChiKey: IZSRJDGCGRAUAR-WDCZJNDASA-N

物化性质

• 沸点：
  650.9±55.0 °C(Predicted)
• 密度：
  1.757±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  -3
• 重原子数：
  13
• 可旋转键数：
  5
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.67
• 拓扑面积：
  135
• 氢给体数：
  5
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  5-keto-L-galactonic acid 在 硫酸 、 丙酮 作用下， 生成 O3,O4;O5,O6-diisopropylidene-ξ-D-arabino-[5]hexulofuranosonic acid
  参考文献：
  名称：

  Ehrlich; Guttmann, Chemische Berichte, 1934, vol. 67, p. 573,586

  摘要：

  DOI：
• 作为产物：
  描述：

  L-galactonic acid 在 Bacteroides vulgatus L-galactonate dehydrogenase 、 β-烟酰胺腺嘌呤二核苷酸 作用下， 以 aq. phosphate buffer 为溶剂， 生成 5-keto-L-galactonic acid
  参考文献：
  名称：

  l-Galactose Metabolism in Bacteroides vulgatus from the Human Gut Microbiota

  摘要：

  A previously unknown metabolic pathway for the utilization of L-galactose was discovered in a prevalent gut bacterium, Bacteroides vulgatus. The new pathway consists of three previously uncharacterized enzymes that were found to be responsible for the conversion of L-galactose to D-tagaturonate. Bvu0219 (L-galactose dehydrogenase) was determined to oxidize L-galactose to L-galactono-1,5-lactone with k(cat) and k(cat)/K-m values of 21 s(-1) and 2.0 x 10(5) M-1 s(-1), respectively. The kinetic product of Bvu0219 is rapidly converted nonenzymatically to the thermodynamically more stable L-galactono-1,4-lactone. Bvu0220 (L-galactono-1,S-lactonase) hydrolyzes both the kinetic and thermodynamic products of Bvu0219 to L-galactonate. However, L-galactono-1,5-lactone is estimated to be hydrolyzed 300-fold faster than its thermodynamically more stable counterpart, L-galactono-1,4-lactone. In the final step of this pathway, Bvu0222 (L-galactonate dehydrogenase) oxidizes L-galactonate to D-tagaturonate with k(cat) and k(cat) /K-m values of 0.6 s(-1) and 1.7 x 10(4) M-1 s(-1), respectively. In the reverse direction, D-tagaturonate is reduced to L-galactonate with values of k(cat) and k(cat)/K-m of 90 s(-1) and 1.6 X 10(5) M-1 s(-1), respectively. D-Tagaturonate is subsequently converted to D-glyceraldehyde and pyruvate through enzymes encoded within the degradation pathway for D-glucuronate and D-galacturonate.

  DOI：

  10.1021/bi500656m

文献信息

• [EN] PROCESS AND INTERMEDIATES FOR THE PRODUCTION OF FURAN-2,5-DICARBOXYLIC ACID OR DERIVATIVES THEREOF<br/>[FR] PROCÉDÉ ET INTERMÉDIAIRES DE PRODUCTION D'ACIDE FURANE-2,5-DICARBOXYLIQUE OU DE SES DÉRIVÉS
  申请人：STICHTING DIENST LANDBOUWKUNDI

  公开号：WO2014182171A1

  公开（公告）日：2014-11-13

  Disclosed is a method of making 5-formyl-2-furoic acid and furan- 2,5-dicarboxylic acid. The method involves the use of 5-keto-aldonic acids as intermediates, as these can be subjected to ring formation by a cyclodehydration reaction under mild conditions. The 5-formyl-2-furoic acid or carboxylic derivative thereof is subjected to oxidation so as to form furan-2,5-dicarboxylic acid. The 5-keto-aldonic acid intermediates can be obtained by isomerization of uronic acids which can be obtained from sugar beet pulp, chicory pulp, fruit peals including orange peels, or non- terrestrial sources like seaweeds. A preferred source is sugar beet pulp.

  揭示了一种制备5-甲酰基-2-呋喃甲酸和呋喃-2,5-二羧酸的方法。该方法涉及使用5-酮-醛酸作为中间体，因为这些中间体可以在温和条件下通过环缩脱水反应进行环形成。5-甲酰基-2-呋喃酸或其羧基衍生物被氧化以形成呋喃-2,5-二羧酸。5-酮-醛酸中间体可以通过异构化获得，而异构化物可以从甜菜根渣、菊苣渣、包括橙皮在内的水果皮或海藻等非陆地来源获得。首选来源是甜菜根渣。
• Bioavailability and improved delivery of alkaline pharmaceutical drugs
  申请人：——

  公开号：US20040214215A1

  公开（公告）日：2004-10-28

  Embodiments of the invention relate to a composition, a process of making the composition, and to the use of the composition. The compositions include a molecular complex formed between an alkaline pharmaceutical drug and at least one selected from a hydroxyacid, a polyhydroxy acid, a related acid, a lactone, or combinations thereof. The compositions provide improved bioavailability and improved delivery of the drug into the cutaneous tissues.

  本发明实施例涉及一种组合物、制备该组合物的过程以及使用该组合物。该组合物包括碱性药物和至少一种选择自羟酸、多羟酸、相关酸、内酯或其组合物的分子复合物。该组合物提供了改善的生物利用度和将药物输送至皮肤组织的改善输送。
• Process for preparing 4-hydroxy-5-methyl-2,3-dihydrofuranone-3 and changing organoleptic properties of foods
  申请人：UNILEVER N.V.

  公开号：EP0058870A1

  公开（公告）日：1982-09-01

  4-Hydroxy-5-methyl-2,3-dihydrofuranone-3 is obtained by heating a solution with pH between 1 and 7 of a 5-ketoaldohexonic acid or a derivative thereof in a polar solvent at a temperature of 70 °C to 150 °C. The 5-keto- aldohexonic acid is preferably 5-ketogluconic acid. Meat flavours are obtained by heating the 5-keto-aidohexonic acid unter the same conditions in the presence of a hydrogen sulphide donor like e.g. cysteine. This reaction product may be incorporated into foodstuffs. Also a process of modifying the organoleptic properties of a foodstuff or an ingredient for a foodstuff having a pH between 5 and 7 before consumption and which has to be heated at least 15 minutes to at least 70 °C by incorporating from 30 to 2000 ppm of a 5-keto-aidohexonic acid is described.

  4-羟基-5-甲基-2,3-二氢呋喃酮-3 是通过在极性溶剂中加热 pH 值介于 1 和 7 之间的 5-酮基-aldohexonic 酸或其衍生物溶液，在 70 °C 至 150 °C 的温度下得到的。5-Keto-aldohexonic acid 最好是 5-Ketogluconic acid。 在有硫化氢供体（如半胱氨酸）存在的情况下，在相同条件下加热 5-酮基-aldohexonic 酸，可获得肉味香精。这种反应产物可以加入食品中。此外，还介绍了一种通过加入 30 至 2000 ppm 的 5-酮-副己酸来改变食品或食品配料的感官特性的工艺，这种食品或食品配料在食用前的 pH 值在 5 至 7 之间，必须加热至少 15 分钟至至少 70 °C。
• Urea composition
  申请人：——

  公开号：US20040033963A1

  公开（公告）日：2004-02-19

  The invention is directed to compositions, methods of making the compositions, and methods of treating cosmetic and dermatological disorders with a composition that includes a molecular complex between urea and a functional substance that has at least one hydroxyl group and one carboxyl group either as a free acid, a salt, an amide or a lactone. The compositions are stable when compared to conventional urea-containing compositions, and provide controlled-release of the urea.

  本发明涉及组合物、组合物的制造方法以及用组合物治疗化妆品和皮肤病的方法，该组合物包括尿素与一种功能物质之间的分子络合物，该功能物质具有至少一个羟基和一个羧基，可以是游离酸、盐、酰胺或内酯。与传统的含尿素组合物相比，这种组合物非常稳定，并能控制尿素的释放。
• Enlargement of mucocutaneous or cutaneous organs and sites with topical compositions
  申请人：Yu J. Ruey

  公开号：US20050171194A1

  公开（公告）日：2005-08-04

  Compositions comprising a hydroxycarboxylic acid, N-acyl-aldosamine, N-acylamino acid or related compound on topical application are beneficial to plump and pout lips, enhance and firm eyelids, enlarge and augment breasts, elongate and expand penis. Because of antioxidant property, certain hydroxycarboxylic acids, N-acyl-aldosamines, N-acylamino acids and related compounds also are useful for topical administration to prevent occurrence of breast cancer or other forms of tumors and cancers.

  由羟基羧酸、N-酰基-醛糖胺、N-酰基氨基酸或相关化合物组成的组合物在局部使用时有利于丰满嘴唇、增强和紧实眼睑、增大和隆起乳房、拉长和扩张阴茎。由于具有抗氧化性，某些羟基羧酸、N-酰基醛胺和 N-酰基氨基酸及相关化合物还可用于局部用药，以预防乳腺癌或其他形式的肿瘤和癌症的发生。