6-[3,4,5-Trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxyhexane-1,2,3,4,5-pentol | 850347-32-9

• 物质功能分类: 生物化工 - 糖类化合物 - 单糖
• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 脂肪酰基
• 英文名称: 6-[3,4,5-Trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxyhexane-1,2,3,4,5-pentol
• CAS: 850347-32-9；64519-82-0；20942-99-8
• 化学式: C₁₂H₂₄O₁₁
• 分子量: 344.31
• InChiKey: SERLAGPUMNYUCK-UHFFFAOYSA-N

物化性质

• 熔点：
  162°C
• 比旋光度：
  [α]D20 +88～+94°(c=4,dil.NH4OH)
• 沸点：
  788.5±60.0 °C(Predicted)
• 密度：
  1.69±0.1 g/cm3(Predicted)
• 溶解度：
  DMSO（少许）、甲醇（少许）、水（少许）
• 物理描述：
  Odourless, white, slightly hygroscopic, crystalline mass.
• 味道：
  Pure sweet taste (sweetening power =0.45 relative to sucrose in about a 10% solution)
• 蒸汽压力：
  3.16X10-17 mm Hg at 25 °C (est)
• 稳定性/保质期：
  远离氧化物。
• 旋光度：
  Specific rotation: +89.8 deg to +92.2 deg
• 分解：
  /Isomalt/ exhibits considerable resistance to acids and microbial influences. ... Isomalt does not undrego browning reactions; it has no reducing groups, and therefore it does not react with other ingredients in a formulation.
• 粘度：
  In the melt, has a lower viscosity, higher specific heat capacity, and higher boiling-point elevation than sucrose

计算性质

• 辛醇/水分配系数(LogP)：
  -5.2
• 重原子数：
  23
• 可旋转键数：
  8
• 环数：
  1.0
• sp3杂化的碳原子比例：
  1.0
• 拓扑面积：
  201
• 氢给体数：
  9
• 氢受体数：
  11

ADMET

代谢

大鼠肠道麦芽糖酶对异麦芽、α-O-D-吡喃葡萄糖基-1,6-D-山梨醇和α-O-D-吡喃葡萄糖基-1,6-D-甘露醇具有活性，但水解速率较慢。大鼠肠道α-葡萄糖苷酶对蔗糖、异麦芽糖和异麦芽的水解速率之比为100:30:12。同样，猪小肠的二糖酶对蔗糖的水解速度约比对α-O-D-吡喃葡萄糖基-1,6-D-山梨醇或α-O-D-吡喃葡萄糖基-1,6-D-甘露醇的水解速度快20倍，而人类肠道α-葡萄糖苷酶对麦芽糖、蔗糖、异麦芽糖和异麦芽的水解相对速率为100:25:11:2。

Rat intestinal maltase was shown to be active against isomalt, alpha-O-D-glucopyranosyl-1,6-D-sorbitol, and alpha-O-D-glucopyranosyl-1,6-D-mannitol, but the rates of hydrolysis were slow. The ratio of the rates of hydrolysis of sucrose, isomaltulose, and isomalt by rat intestinal alpha-glucosidases was 100:30:12. Similarly, sucrose was hydrolysed about 20 times faster than alpha-O-D-glucopyranosyl-1,6-D-sorbitol or alpha-O-D-glucopyranosyl-1,6-D-mannitol by disaccharidases from the small intestine of the pig, and the relative rates of hydrolysis of maltose, sucrose, isomaltulose and isomalt by human intestinal alpha-glucosidases were 100:25:11:2.

来源:Hazardous Substances Data Bank (HSDB)

代谢

在3-4周的时间内，将饲料中异麦芽糖的含量从10%增加到34.5%，研究了适应了这种化合物的雌性大鼠胃肠道的命运。在给予5克饲料中含有1.7克异麦芽糖后，每隔6小时检查一次胃、小肠、盲肠和大肠的内容物。从这些器官中发现的α-O-D-葡萄糖吡喃糖基-1,6-D-山梨醇、α-O-D-葡萄糖吡喃糖基-1,6-D-甘露醇、山梨醇、甘露醇和蔗糖的含量来看，作者得出结论，α-O-D-葡萄糖吡喃糖基-1,6-D-山梨醇和α-O-D-葡萄糖吡喃糖基-1,6-D-甘露醇在小肠的 carbohydrases 作用下仅部分水解，而大部分这些化合物到达盲肠，在盲肠中进一步水解糖苷键。释放出的己糖醇在盲肠中进行发酵，盲肠肿大，只有少量α-O-D-葡萄糖吡喃糖基-1,6-D-山梨醇、α-O-D-葡萄糖吡喃糖基-1,6-D-甘露醇和己糖醇到达大肠。

The fate of isomalt in the gastrointestinal tract of female rats that had been adapted to the compound was investigated by increasing its dietary concentration from 10% to 34.5% over a period of 3-4 weeks. After administration of 1.7 g isomalt in 5 g feed, the contents of the stomach, small intestine, cecum, and large intestine were examined at intervals up to 6 hr. From the content of alpha-O-D-glucopyranosyl-1,6-D-sorbitol, alpha-O-D-glucopyranosyl-1,6-D-mannitol, sorbitol, mannitol, and sucrose found in these organs, the authors concluded that alpha-O-D-glucopyranosyl-1,6-D-sorbitol and alpha-O-D-glucopyranosyl-1,6-D-mannitol were only partially hydrolyzed by the carbohydrases in the small intestine, while a substantial proportion of these compounds reached the cecum where further hydrolysis of glycosidic bonds occurred. Fermentation of the liberated hexitols occurred in the cecum, which was enlarged, and only small amounts of alpha-O-D-glucopyranosyl-1,6-D-sorbitol, alpha-O-D-glucopyranosyl-1,6-D-mannitol, and hexitols reached the large intestine.

来源:Hazardous Substances Data Bank (HSDB)

毒理性

• 相互作用

龋齿和牙周病是普遍存在的口腔疾病，其病因与碳水化合物甜味剂的摄入密切相关。人类的临床试验和几项动物实验表明，用某些糖醇（多元醇）替代蔗糖可以获得有希望的临床效果。在糖醇中，迄今为止效果最好的是木糖醇，它是一种含有五个碳原子的戊糖醇。含有木糖醇的口香糖已被证明是针对龋病活跃年龄组和高风险人群的强大工具。需要更多的研究来评估木糖醇与山梨糖醇、异麦芽酮糖、麦芽糖醇、其他糖醇和强力甜味剂混合物预防口腔菌斑疾病的能力。尽管尚未对碳水化合物甜味剂与牙周病之间的关系进行彻底的临床试验，但现有数据表明，饮食中的多元醇可能对牙周和牙龈炎症有一定的抑制效果。

Dental caries and periodontal disease are wide-spread oral illnesses whose etiology is intimately associated with the consumption of carbohydrate sweeteners....Human clinical trials and several animal experiments have shown promising clinical results obtained by replacing sucrose with certain sugar alcohols (polyols). Among the sugar alcohols, the best results so far have been obtained with xylitol, which is chemically a pentitol containing five carbon atoms. Chewing gums containing xylitol have been shown to be strong instruments against caries in caries-active age-groups and in high-risk subjects. More research is needed to assess the ability of mixtures of xylitol with sorbitol, palatinit, maltitol, other sugar alcohols, and intense sweeteners to prevent oral plaque diseases. Although thorough clinical trials on the relationship between carbohydrate sweeteners and periodontal diseases have not been performed, the available data indicate that dietary polyols may have a restricted dampening effect on periodontal and gingival inflammations.

来源:Hazardous Substances Data Bank (HSDB)

毒理性

• 解毒与急救

/SRP:/ 紧急急救：确保已经进行了充分的中和。如果患者停止呼吸，请开始人工呼吸，最好使用需求阀复苏器、袋阀面罩装置或口袋面罩，按训练操作。如有必要，执行心肺复苏。立即用缓慢流动的水冲洗受污染的眼睛。不要催吐。如果发生呕吐，让患者前倾或置于左侧（如果可能的话，头部向下）以保持呼吸道畅通，防止吸入。保持患者安静，维持正常体温。寻求医疗帮助。 /高醇（大于3个碳）及相关化合物/

/SRP:/ Immediate first aid: Ensure that adequate decontamination has been carried out. If patient is not breathing, start artificial respiration, preferably with a demand-valve resuscitator, bag-valve-mask device, or pocket mask, as trained. Perform CPR as necessary. Immediately flush contaminated eyes with gently flowing water. Do not induce vomiting. If vomiting occurs, lean patient forward or place on left side (head-down position, if possible) to maintain an open airway and prevent aspiration. Keep patient quiet and maintain normal body temperature. Obtain medical attention. /Higher alcohols (>3 carbons) and related compounds/

来源:Hazardous Substances Data Bank (HSDB)

毒理性

• 解毒与急救

/SRP:/ 基本治疗：建立专利气道（如有需要，使用口咽或鼻咽气道）。如有必要，进行吸痰。密切观察呼吸不足的迹象，如有必要，进行辅助通气。通过非重复呼吸面罩以10至15升/分钟的速度给予氧气。监测休克迹象并在必要时进行治疗……监测肺水肿迹象并在必要时进行治疗……预期可能出现癫痫并在必要时进行治疗……对于眼睛污染，立即用水冲洗眼睛。在转运过程中，用0.9%的生理盐水（NS）持续冲洗每只眼睛……不要使用催吐剂。对于摄入，如果患者能够吞咽、有强烈的呕吐反射并不流口水，则用水冲洗口腔，并给予5毫升/千克，最多200毫升的水进行稀释。给予活性炭……/高醇（大于3个碳）及相关化合物/

/SRP:/ Basic Treatment: Establish a patent airway (oropharyngeal or nasopharyngeal airway, if needed). Suction if necessary. Watch for signs of respiratory insufficiency and assist ventilations if necessary. Administer oxygen by nonrebreather mask at 10 to 15 L/min. Monitor for shock and treat if necessary ... . Monitor for pulmonary edema and treat if necessary ... . Anticipate seizures and treat if necessary ... . For eye contamination, flush eyes immediately with water. Irrigate each eye continuously with 0.9% saline (NS) during transport ... . Do not use emetics. For ingestion, rinse mouth and administer 5 ml/kg up to 200 ml of water for dilution if the patient can swallow, has a strong gag reflex, and does not drool. Administer activated charcoal ... . /Higher alcohols (>3 carbons) and related compounds/

来源:Hazardous Substances Data Bank (HSDB)

毒理性

• 解毒与急救

/SRP:/ 高级治疗：对于无意识、严重肺水肿或严重呼吸困难的病人，考虑进行口咽或鼻咽气管插管以控制气道。正压通气技术，使用球囊阀面罩装置可能有益。考虑使用药物治疗肺水肿……。监测心率和必要时治疗心律失常……。开始静脉输注D5W /SRP: "保持开放"，最低流量/。如果出现低血容量的迹象，使用0.9%生理盐水（NS）或乳酸钠林格氏液（LR）。对于伴有低血容量迹象的低血压，谨慎给予液体。如果病人在正常血容量下出现低血压，考虑使用血管加压药。注意液体过载的迹象……。监测低血糖的迹象（意识水平下降、心动过速、苍白、瞳孔扩大、出汗和/或葡萄糖试纸或血糖仪读数低于50毫克），必要时给予50%葡萄糖……。用地西泮或劳拉西泮治疗癫痫……。使用丙美卡因盐酸协助眼部冲洗……。/高醇（>3个碳）及相关化合物/

/SRP:/ Advanced Treatment: Consider orotracheal or nasotracheal intubation for airway control in the patient who is unconscious, has severe pulmonary edema, or is in severe respiratory distress. Positive-pressure ventilation techniques, with a bag-valve-mask device, may be beneficial. Consider drug therapy for pulmonary edema ... . Monitor cardiac rhythm and treat arrhythmias as necessary ... . Start IV administration of D5W /SRP: "To keep open", minimal flow rate/. Use 0.9% saline (NS) or lactated Ringer's (LR) if signs of hypovolemia are present. For hypotension with signs of hypovolemia, administer fluid cautiously. Consider vasopressors if patient is hypotensive with a normal fluid volume. Watch for signs of fluid overload ... . Monitor for signs of hypoglycemia (decreased LOC, tachycardia, pallor, dilated pupils, diaphoresis, and/or dextrose strip or glucometer readings below 50 mg) and administer 50% dextrose if necessary ... . Treat seizures with diazepam or lorazepam ... . Use proparacaine hydrochloride to assist eye irrigation ... . /Higher alcohols (>3 carbons) and related compounds/

来源:Hazardous Substances Data Bank (HSDB)

毒理性

• 人类毒性摘录

人类暴露研究/多元醇异麦芽糖（Palatinit）是一种已确立的糖替代品。在十九名健康志愿者中进行了一项随机、双盲、交叉试验，研究了定期摄入异麦芽糖对代谢和肠道功能参数的影响，试验包括两个为期4周的测试期。志愿者作为控制饮食的一部分，每天摄入30克异麦芽糖或30克蔗糖。除了临床标准诊断外，还分析了当前被认为是冠心病、糖尿病或肥胖风险因素的生物标志物和参数。测量了尿液和粪便中的钙和磷酸盐排泄量。此外，还确定了平均转运时间、排便频率、粪便一致性和重量。通过尿液中甘露醇的排泄确认了测试产品的摄入。在两个阶段中，血液脂质相似，特别是在高脂血症的志愿者中，除了所有受试者的apo A-1较低（P=0.03）。残余样颗粒、氧化LDL、游离脂肪酸、果糖胺和瘦素相似，并未受到异麦芽糖的影响。钙和磷酸盐的稳态未受影响。在异麦芽糖阶段，排便频率适度增加（P=0.006），而粪便一致性和粪便水未发生变化。这表明异麦芽糖耐受性良好，摄入异麦芽糖不会损害代谢功能或引起高钙尿症。...

/HUMAN EXPOSURE STUDIES/ The polyol isomalt (Palatinit) is a well established sugar replacer. The impact of regular isomalt consumption on metabolism and parameters of gut function in nineteen healthy volunteers was examined in a randomised, double-blind, cross-over trial with two 4-week test periods. Volunteers received 30 g isomalt or 30 g sucrose daily as part of a controlled diet. In addition to clinical standard diagnostics, biomarkers and parameters currently discussed as risk factors for CHD, diabetes or obesity were analysed. Urine and stool Ca and phosphate excretions were measured. In addition, mean transit time, defecation frequency, stool consistency and weight were determined. Consumption of test products was affirmed by the urinary excretion of mannitol. Blood lipids were comparable in both phases, especially in volunteers with hyperlipidaemia, apart from lower apo A-1 (P=0.03) for all subjects. Remnant-like particles, oxidised LDL, NEFA, fructosamine and leptin were comparable and not influenced by isomalt. Ca and phosphate homeostasis was not affected. Stool frequency was moderately increased in the isomalt phase (P=0.006) without changes in stool consistency and stool water. This suggests that isomalt is well tolerated and that consumption of isomalt does not impair metabolic function or induce hypercalciuria. ...

来源:Hazardous Substances Data Bank (HSDB)

吸收、分配和排泄

在大肠内，异麦芽糖的体内代谢通过体外发酵研究进行了模拟，以调查其在使用猪食糜作为基本底物并额外接种粪便的情况下的降解情况。在第一周，研究了非适应性微生物群对异麦芽糖（3.65%）的发酵情况。在第二周，研究了适应性微生物群对异麦芽糖的发酵情况，这些微生物群来自喂食了添加了异麦芽糖的基础饮食的猪。在第三周，对高浓度异麦芽糖（7.30%）的发酵实验中同时研究了非适应性和适应性微生物群。异麦芽糖被降解为乳酸、挥发性脂肪酸和气体（CO2、CH4和氢气）……

The in vivo metabolism of isomalt in the large intestine was simulated in an in vitro fermentation study to investigate its degradation using chyme from pigs as a basic substrate additionally inoculated with feces. In the first week, the fermentation of isomalt (3.65%) by non-adapted microflora was investigated. In the second week, isomalt fermentation by adapted microflora taken from pigs fed a basic diet supplemented with isomalt was studied. In the third week, both /non-adapted and adapted/ flora were studied in fermentation experiments with a high concentration of isomalt (7.30%). Isomalt was degraded to lactic acid, volatile fatty acids, and gases (CO2, CH4, and hydrogen). ...

来源:Hazardous Substances Data Bank (HSDB)

吸收、分配和排泄

瘘管猪和正常猪在餐间喂食了10%的蔗糖，5%或10%的异麦芽糖，或者与餐食一起喂食了10%的异麦芽糖。这些物质的通过和吸收率在回肠末端（每种处理10头猪）或整个消化道的全程（每种处理4头猪）被确定。10%的蔗糖在小肠中被完全消化和吸收。在3种异麦芽糖处理中，61-64%的摄入化合物以完整的异麦芽糖加上自由的山梨糖、自由的甘露醇和自由的葡萄糖的形式通过了回肠末端。这些糖没有在粪便中排出，表明通过回肠末端的异麦芽糖及其成分在大肠中被完全分解。

Fistulated and normal pigs were fed 10% sucrose between meals, 5 or 10% isomalt between meals, or 10% isomalt with meals. The passage and absorption rate of these substances were determined at the terminal ileum (10 pigs per treatment) or over the whole distance of the digestive tract (4 pigs per treatment). Ten percent sucrose was completely digested and absorbed in the small intestine. In the 3 isomalt treatments, 61-64% of the ingested compound passed the terminal ileum in the form of intact isomalt plus free sorbitol, free mannitol, and free glucose. None of these sugars were excreted in the feces, indicating that isomalt and its constituents passing the terminal ileum are completely broken down in the large intestine.

来源:Hazardous Substances Data Bank (HSDB)

吸收、分配和排泄

肾清除率研究在成年雌性大鼠（体重250克）中进行，这些大鼠在3小时内输注了1.8克的异麦芽糖、α-O-D-葡萄糖苷-1,6-D-山梨糖醇或α-O-D-葡萄糖苷-1,6-D-甘露糖醇。血浆中达到了最大浓度25 mM。这些化合物被迅速清除，尿液中记录到的浓度高达100 mg/mL，这与每天口服5克异麦芽糖的大鼠最大尿液浓度0.6 mg/mL相比。在输注异麦芽糖或α-O-D-葡萄糖苷-1,6-D-山梨糖醇后，血液或尿液中未检测到自由山梨糖，血糖浓度没有变化，这表明这些双糖醇在代谢上是惰性的。根据输注和排泄速率以及观察到的血浆浓度，作者得出结论，α-O-D-葡萄糖苷-1,6-D-山梨糖醇分布在细胞外液中，但不会到达细胞内室。

Renal clearance studies were conducted in adult female rats (250 g b.w.) infused with 1.8 g isomalt, alpha-O-D-glucopyranosyl-1,6-D-sorbitol, or alpha-O-D-glucopyranosyl-1,6-D-mannitol over a period of 3 hours. Maximum plasma concentrations of 25 mM were obtained. These compounds were readily cleared and urinary concentrations of up to 100 mg/mL were recorded, which compares with a maximum urinary concentration of 0.6 mg/mL in rats receiving 5 g isomalt per day orally. After the infusion of either isomalt or alpha-O-D-glucopyranosyl-1,6-D-sorbitol, free sorbitol was not detected in blood or urine, and blood glucose concentrations were unchanged, demonstrating the metabolic inertness of these disaccharide alcohols. From the infusion and excretion rates and the plasma concentrations that were observed, the authors concluded that alpha-O-D-glucopyranosyl-1,6-D-sorbitol is distributed in extracellular water, but does not reach the intracellular compartments.

来源:Hazardous Substances Data Bank (HSDB)

吸收、分配和排泄

当连续几周给大鼠喂食异麦芽糖时，观察到粪便排泄量稳步下降，而盲肠则增大。作者们得出结论，这是由于肠道微生物群的适应和代谢所致。同样地，在为期17天的喂养期间，6只雌性大鼠每天摄入3.5克异麦芽糖，粪便中的含量从开始时的剂量的25%降至结束时的1%。

When isomalt was fed to rats for several weeks it was observed that fecal excretion declined steadily, while the cecum enlarged. The authors concluded that this resulted from adaptation and metabolism by the gut microflora. Similarly, during a 17-day feeding period in which 6 female rats received 3.5 g isomalt daily, the fecal content fell from 25% of the dose at the beginning to 1% at the end.

来源:Hazardous Substances Data Bank (HSDB)

安全信息

• 储存条件：
  存放在密封容器内，并放置在阴凉、干燥的地方。

制备方法与用途

合成方法

1-O-Α-D-吡喃葡萄糖-D-甘露糖醇二水合物（以下简称为1,1-GPM）的合成通常分为两步：首先，通过蔗糖酶作用将蔗糖转化为异麦芽酮糖；其次，在雷尼镍催化剂上对分离出的异麦芽酮糖进行氢化。其中，利用微生物红色原杆菌可以实现蔗糖向异麦芽酮糖的转化。此过程产生的异麦芽酮糖在雷尼镍催化剂的存在下通过氢化反应转化为1,1-GPM和6-O-α-D-吡喃葡萄糖基-D-山梨糖醇（简称1,6-GPS）的混合物，随后通过蒸发与冷却结晶进行浓缩。

应用举例

1. 将1-O-Α-D-吡喃葡萄糖-D-甘露糖醇二水合物（即1,1-GPM）和6-O-α-D-吡喃葡萄糖基-D-山梨糖醇（简称1,6-GPS）的混合物用作益生元和/或丁酸根供体，尤其适用于在人的食物和其他消费品、动物饲料产品以及药物中作为可消化并有益于肠道健康的碳水化合物。
2. 异麦芽酮糖醇（氢化异麦芽酮糖），由于其非致龋性、低热量及对糖尿病患者适宜的特点，作为一种糖替代品具有明显优势。

文献信息

• METHOD FOR STABILIZING HALOGEN-FREE THERMOPLASTIC RECYCLATES, STABILIZED PLASTIC COMPOSITIONS, AND MOLDING COMPOUNDS AND MOLDED PARTS PRODUCED THEREFROM
  申请人：FRAUNHOFER-GESELLSCHAFT ZUR FÖRDERUNG DER ANGEWANDTEN FORSCHUNG E. V.

  公开号：US20200317886A1

  公开（公告）日：2020-10-08

  The invention relates to a method for stabilizing halogen-free thermoplastic recyclates or pre-damaged plastics against oxidative, thermal, and/or actinic degradation. In the method according to the invention, at least one alditol or cyclitol is introduced into a halogen-free thermoplastic recyclate as a component, and optionally in addition thereto, at least one primary antioxidant and/or at least one secondary antioxidant is introduced into a halogen-free thermoplastic recyclate. By virtue of the method according to the invention, plastic recyclates can be stabilized against oxidative, thermal, and/or actinic degradation with a high degree of effectiveness and in a very environmentally friendly and inexpensive manner. The invention additionally relates to corresponding recyclate-based plastic compositions, to molding compound and molded parts produced therefrom, to stabilizer compositions, and to the use thereof for stabilizing halogen-free thermoplastic recyclates against oxidative, thermal, and/or actinic degradation.
• METHOD OF STABILIZING VIRGIN THERMOPLASTIC MATERIAL AND STABILIZED PLASTICS COMPOSITIONS, MOULDING COMPOUNDS AND MOULDINGS PRODUCED THEREFROM, STABILIZER COMPOSITIONS AND USES THEREOF
  申请人：FRAUNHOFER-GESELLSCHAFT ZUR FÖRDERUNG DER ANGEWANDTEN FORSCHUNG E. V.

  公开号：US20210388176A1

  公开（公告）日：2021-12-16

  The present invention relates to a method of stabilizing virgin thermoplastic material against oxidative, thermal and/or actinic degradation. In the method of the invention, at least one polyphenol and at least one alditol and/or cyclitol are introduced into a virgin thermoplastic material. The method of the invention can stabilize virgin thermoplastic material with high efficacy and in a very environmentally friendly and inexpensive manner against oxidative, thermal and/or actinic degradation. The present invention additionally also relates to correspondingly stabilized virgin thermoplastic material and to moulding compounds and mouldings produced therefrom. The present invention also further relates to stabilizer compositions and to the use thereof for stabilization of virgin thermoplastic material against oxidative, thermal and/or actinic degradation.