(R,R)-(+)-Hydrobenzoin
(Synonyms: 氢胺) 目录号 : GC39832
(R,R)-(+)-Hydrobenzoin 是一种有机催化剂。
Cas No.:52340-78-0
Sample solution is provided at 25 µL, 10mM.
;)
,-1-7$$$37316672.jpg');)
;)
;)
$$$36806353.jpg');)
;33(7)%EF%BC%9A546-561$$$37156877.jpg');)
;)
;)
;)
%201124-1138.$$$35908550.jpg');)
%20766-780.$$$37100057.jpg');)
%20418-432.$$$36893736.jpg');)
%EF%BC%9A-240-255.$$$35108512.jpg');)
533-545$$$36543525.jpg');)
%201-13.$$$36600053.jpg');)
;)
Quality Control & SDS
- View current batch:
- Purity: >99.50%
- COA (Certificate Of Analysis)
- SDS (Safety Data Sheet)
- Datasheet
(R,R)-(+)-Hydrobenzoin is a organocatalysts[1].
[1]. Kwan SooKim, et al. Synthesis of enantiopure cyclopentitols and aminocyclopentitols mediated by oxyselenenylation of cyclopentene with (R,R)-hydrobenzoin. Tetrahedron Letters. 1988. [2]. (+)-(1R,2R)-1,2-Diphenylethane-1,2-diol.
| Cas No. | 52340-78-0 | SDF | |
| 别名 | 氢胺 | ||
| Canonical SMILES | O[C@H](C1=CC=CC=C1)[C@@H](C2=CC=CC=C2)O | ||
| 分子式 | C14H14O2 | 分子量 | 214.26 |
| 溶解度 | Soluble in DMSO | 储存条件 | Store at -20°C |
| General tips | 请根据产品在不同溶剂中的溶解度选择合适的溶剂配制储备液；一旦配成溶液，请分装保存，避免反复冻融造成的产品失效。 储备液的保存方式和期限：-80°C 储存时，请在 6 个月内使用，-20°C 储存时，请在 1 个月内使用。 为了提高溶解度，请将管子加热至37℃，然后在超声波浴中震荡一段时间。 |
||
| Shipping Condition | 评估样品解决方案：配备蓝冰进行发货。所有其他可用尺寸：配备RT，或根据请求配备蓝冰。 | ||
| 制备储备液 | |||
 |
1 mg | 5 mg | 10 mg |
| 1 mM | 4.6672 mL | 23.3361 mL | 46.6723 mL |
| 5 mM | 0.9334 mL | 4.6672 mL | 9.3345 mL |
| 10 mM | 0.4667 mL | 2.3336 mL | 4.6672 mL |
| 第一步：请输入基本实验信息（考虑到实验过程中的损耗，建议多配一只动物的药量） | ||||||||||
| 给药剂量 | mg/kg |  |
动物平均体重 | g | |
每只动物给药体积 | ul | |
动物数量 | 只 |
| 第二步：请输入动物体内配方组成（配方适用于不溶于水的药物；不同批次药物配方比例不同，请联系GLPBIO为您提供正确的澄清溶液配方） | ||||||||||
| % DMSO % % Tween 80 % saline | ||||||||||
| 计算重置 | ||||||||||
计算结果:
工作液浓度： mg/ml；
DMSO母液配制方法： mg 药物溶于 μL DMSO溶液（母液浓度 mg/mL，
体内配方配制方法：取 μL DMSO母液，加入 μL PEG300，混匀澄清后加入μL Tween 80，混匀澄清后加入 μL saline，混匀澄清。
1. 首先保证母液是澄清的；
2.
一定要按照顺序依次将溶剂加入，进行下一步操作之前必须保证上一步操作得到的是澄清的溶液，可采用涡旋、超声或水浴加热等物理方法助溶。
3. 以上所有助溶剂都可在 GlpBio 网站选购。
Enantioseparation of benzoins and enantiomer migration reversal of hydrobenzoin in capillary zone electrophoresis with dual cyclodextrin systems and borate complexation
J Chromatogr A 2004 Apr 2;1032(1-2):227-35.PMID:15065800DOI:10.1016/j.chroma.2004.01.011.
Enantioseparations of racemic hydrobenzoin and structurally related compounds, including benzoin and benzoin methyl ether, in capillary zone electrophoresis (CZE) with dual cyclodextrin (CD) systems consisting of S-beta-CD (mixed isomers) and a neutral CD, including beta-CD and hydroxypropyl-beta-CD (HP-beta-CD), as chiral selectors in the presence of borate complexation at pH 9.0 were investigated. Effective enantioseparations of hydrobenzoin were achieved with addition of dual CD systems and also with neutral CDs in a borate buffer. The enantioseparation and migration behavior of hydrobenzoin in such an electrophoretic system are primarily governed by the interaction of the borate complex of hydrobenzoin with beta-CDs. The CD complexations of both hydrobenzoin and the borate complexes of hydrobenzoin with beta-CDs increase in the order S-beta-CD < HP-beta-CD < beta-CD. As a result, enantioseparations of hydrobenzoin with the use of dual CD systems consisting of S-beta-CD/beta-CD and S-beta-CD/HP-beta-CD as chiral selectors are more advantageous than that with the use of S-beta-CD alone. With these dual CD systems in the presence of borate complexation, the enantiomer migration reversal was observed for hydrobenzoin. The interactions of hydrobenzoin with neutral CDs and with S-beta-CD exhibit the same chiral recognition pattern, but opposite effect on the mobility of the enantiomers. The (S,S)-enantiomer of hydrobenzoin was found to interact more strongly than the (R,R)-enantiomer with neutral CDs. For comparison, enantioseparation of hydrobenzoin, together with benzoin and benzoin methyl ether, with dual CD systems in a phosphate background electrolyte at pH 9.0 was also examined. The migration order and enantioselectivity of these three benzoins depend on the degree of CD complexations between benzoins and both S-beta-CD and neutral CD in a phosphate background electrolyte. In addition, effective enantioseparations of hydrobenzoin were also achievable with addition of either beta-CD at concentrations greater than 1.0 mM or HP-beta-CD at concentrations exceeding 2.0 mM in a borate buffer at pH 9.0.
Migration behavior and enantioseparation of hydrobenzoin and structurally related compounds in capillary zone electrophoresis with a dual cyclodextrin system consisting of heptakis-(2,3-dihydroxy-6-O-sulfo)-beta-cyclodextrin and beta-cyclodextrin
Electrophoresis 2005 Nov;26(21):4187-96.PMID:16252333DOI:10.1002/elps.200500294.
Migration behavior and enantioseparation of racemic hydrobenzoin and structurally related compounds, including benzoin and benzoin methyl ether, in CZE with a dual CD system consisting of heptakis-(2,3-dihydroxy-6-O-sulfo)-beta-CD (SI-S-beta-CD) and beta-CD as chiral selectors in the presence and absence of borate complexation at pH 9.0 were investigated. The results indicate that enantioseparation of hydrobenzoin is mainly governed by CD complexation of hydrobenzoin-borate complexes with SI-S-beta-CD when SI-S-beta-CD concentration is relatively high. Whereas CD complexation of hydrobenzoin-borate complexes with beta-CD plays a significant role in enantioseparation when SI-S-beta-CD concentration is comparatively low. The (S,S)-enantiomer of the hydrobenzoin-borate complex was found to interact more strongly than the corresponding (R,R)-enantiomer with both SI-S-beta-CD and beta-CD. These two types of CD show the same chiral recognition pattern, but they exhibit opposite effects on the mobility of the enantiomers of hydrobenzoin-borate complexes. Enantiomer migration reversal of hydrobenzoin occurred in the presence of borate complexation when varying the concentration of beta-CD, while keeping SI-S-beta-CD at a relatively low concentration. Binding constants of the enantiomers of benzoin-related compounds to beta-CD and those of hydrobenzoin-borate complexes to SI-beta-CD were evaluated; the mobility contributions of all complex species to the effective mobility of the enantiomers of hydrobenzoin as a function of beta-CD concentration in a borate buffer were analyzed. In addition, comparative studies on the enantioseparation of benzoin-related compounds with SI-S-beta-CD and with randomly sulfate-substituted beta-CD were made.
Enantioseparations of hydrobenzoin and structurally related compounds in capillary zone electrophoresis using heptakis(2,3-dihydroxy-6-O-sulfo)-beta-cyclodextrin as chiral selector and enantiomer migration reversal of hydrobenzoin with a dual cyclodextrin system in the presence of borate complexation
Electrophoresis 2004 Aug;25(16):2786-94.PMID:15352010DOI:10.1002/elps.200405968.
We investigated the enantioseparations of racemic hydrobenzoin, together with benzoin and benzoin methyl ether, in capillary electrophoresis (CE) using the single-isomer heptakis(2,3-dihydroxy-6-O-sulfo)-beta-cyclodextrin (SI-S-beta-CD) as a chiral selector in the presence and absence of borate complexation and enantiomer migration reversal of hydrobenzoin with a dual CD system consisting of SI-S-beta-CD and beta-CD in the presence of borate complexation at pH 9.0 in a borate buffer. The enantioselectivity of hydrobenzoin increased remarkably with increasing SI-S-beta-CD concentration and the enantioseparation depended on CD complexation between hydrobenzoin-borate and SI-S-beta-CD. The (S,S)-enantiomer of hydrobenzoin-borate complexes interacted more strongly than the (R,R)-enantiomer with SI-S-beta-CD. The enantiomers of hydrobenzoin could be baseline-resolved in the presence of SI-S-beta-CD at a concentration as low as 0.1% w/v, whereas the three test analytes were simultaneously enantioseparated with addition of 0.3% w/v SI-S-beta-CD or at concentrations >2.0% w/v in a borate buffer and 0.5% w/v in a phosphate background electrolyte at pH 9.0. Compared with the results obtained previously using randomly sulfated beta-CD (MI-S-beta-CD) in a borate buffer, enantioseparation of these three benzoin compounds is more advantageously aided by SI-S-beta-CD as the chiral selector. The enantioselectivity of hydrobenzoin depended greatly on the degree of substitution of sulfated beta-CD. Moreover, binding constants of the enantiomers of benzoin compounds to SI-S-beta-CD and those of hydrobenzoin-borate complexes to SI-S-beta-CD were evaluated for a better understanding of the role of CD complexation in the enantioseparation and chiral recognition. Enantiomer migration reversal of hydrobenzoin could be observed by varying the concentration of beta-CD, while keeping SI-S-beta-CD at a relatively low concentration. SI-S-beta-CD and beta-CD showed the same chiral recognition pattern but they exhibited opposite effects on the mobility of the enantiomers.
Synthesis, Biological, and Computational Evaluation of Antagonistic, Chiral Hydrobenzoin Esters of Arecaidine Targeting mAChR M1
Pharmaceuticals (Basel) 2020 Nov 30;13(12):437.PMID:33266067DOI:10.3390/ph13120437.
Muscarinic acetylcholine receptors (mAChRs) are a pivotal constituent of the central and peripheral nervous system. Yet, therapeutic and diagnostic applications thereof are hampered by the lack of subtype selective ligands. Within this work, we synthesized and chemically characterized three different stereoisomers of hydrobenzoin esters of arecaidine by NMR, HR-MS, chiral chromatography, and HPLC-logP. All compounds are structurally eligible for carbon-11 labeling and show appropriate stability in Dulbecco's phosphate-buffered saline (DPBS) and F12 cell culture medium. A competitive radioligand binding assay on Chinese hamster ovary cell membranes comprising the human mAChR subtypes M1-M5 showed the highest orthosteric binding affinity for subtype M1 and a strong influence of stereochemistry on binding affinity, which corresponds to in silico molecular docking experiments. Ki values toward M1 were determined as 99 ± 19 nM, 800 ± 200 nM, and 380 ± 90 nM for the (R,R)-, (S,S)-, and racemic (R,S)-stereoisomer, respectively, highlighting the importance of stereochemical variations in mAChR ligand development. All three stereoisomers were shown to act as antagonists toward mAChR M1 using a Fluo-4 calcium efflux assay. With respect to future positron emission tomography (PET) tracer development, the (R,R)-isomer appears especially promising as a lead structure due to its highest subtype selectivity and lowest Ki value.
Methods for determination of all binding parameters in systems with simultaneous borate and cyclodextrin complexation
J Chromatogr A 2011 Oct 7;1218(40):7211-8.PMID:21871626DOI:10.1016/j.chroma.2011.07.088.
Two novel methods for determination of binding constants in the systems with borate and cyclodextrin complexation were developed. The methods enable to determine all binding parameters in these systems and even the binding constants of interaction of a neutral analyte with a neutral cyclodextrin. The first method is based on nonlinear fitting of experimental data and further evaluation of fitting parameters. The second method requires a multiple regression. The methods provide identical results with low experimental error. Only one set of measurements is required for both methods. Thus the binding parameters can be mutually compared. The binding parameters for neutral analytes ((R,R)-(+)-hydrobenzoin and (S,S)-(-)-hydrobenzoin) and neutral cyclodextrin (heptakis(2,6-di-O-methyl)-β-cyclodextrin) were evaluated and the effect of individual types of interaction was revealed. The interaction of the analytes with cyclodextrin governs the chiral recognition, while the complexation of analyte with borate is responsible for electromigration. Very low values of the binding constants of mixed analyte-cyclodextrin-borate complexes indicate that this type of complexation has negligible effect on enantioseparation.