(R)-(-)-2-Butanol
(Synonyms: (R)-丁烷-2-醇) 目录号 : GC61694
(R)-(-)-2-Butanol是由雌性白色甲虫(Dasylepidaishigakiensis)释放的，用来吸引雄性。(R)-(-)-2-Butanol是药物合成的中间体。
Cas No.:14898-79-4
Sample solution is provided at 25 µL, 10mM.
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Quality Control & SDS
- View current batch:
- Purity: >98.00%
- COA (Certificate Of Analysis)
- SDS (Safety Data Sheet)
- Datasheet
(R)-(-)-2-Butanol is released by the females of the white grub beetle, Dasylepida ishigakiensis, to attract males. (R)-(-)-2-Butanol is an intermediate of pharmaceutical synthesis by coupling[1][2].
[1]. N Fujiwara-Tsujii, et al. Age-dependent changes in the ratio of (R)- and (S)-2-butanol released by virgin females of Dasylepida ishigakiensis (Coleoptera: Scarabaeidae). Bull Entomol Res. 2012 Dec;102(6):730-6. [2]. Aram Hong, et al. Induced Circular Dichroism of Jet-Cooled Phenol Complexes with ( R)-(-)-2-Butanol. J Phys Chem A. 2019 Oct 17;123(41):8913-8920.
| Cas No. | 14898-79-4 | SDF | |
| 别名 | (R)-丁烷-2-醇 | ||
| Canonical SMILES | C[C@@H](O)CC | ||
| 分子式 | C4H10O | 分子量 | 74.12 |
| 溶解度 | DMSO : 100 mg/mL (1349.16 mM; Need ultrasonic) | 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。 |
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| 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 | |||
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1 mg | 5 mg | 10 mg |
| 1 mM | 13.4916 mL | 67.4582 mL | 134.9164 mL |
| 5 mM | 2.6983 mL | 13.4916 mL | 26.9833 mL |
| 10 mM | 1.3492 mL | 6.7458 mL | 13.4916 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。
Stereo-Divergent Enzyme Cascades to Convert Racemic 4-Phenyl-2-Butanol into either (S)- or (R)-Corresponding Chiral Amine
Chembiochem 2022 Apr 20;23(8):e202200108.PMID:35189014DOI:10.1002/cbic.202200108.
The synthesis of enantiopure chiral amines from racemic alcohols is a key transformation in the chemical industry, e. g., in the production of active pharmaceutical ingredients (APIs). However, this reaction remains challenging. In this work, we propose a one-pot enzymatic cascade for the direct conversion of a racemic alcohol into either (S)- or (R)-enantiomers of the corresponding amine, with in-situ cofactor recycling. This enzymatic cascade consists of two enantio-complementary alcohol dehydrogenases, both NADH and NADPH oxidase for in-situ recycling of NAD(P)+ cofactors, and either (S)- or (R)-enantioselective transaminase. This cell-free biocatalytic system has been successfully applied to the conversion of racemic 4-phenyl-2-butanol into the high value (S)- or (R)-enantiomers of the amine reaching good (73 % (S)) and excellent (>99 % (R)) enantioselectivities.
Kinetic resolution of (R,S)-2-butanol using enzymatic synthesis of esters
Appl Biochem Biotechnol 2011 Nov;165(5-6):1129-40.PMID:21837379DOI:10.1007/s12010-011-9330-z.
Kinetic resolution of (R,S)-2-butanol using enzymatic synthesis of esters has been studied. (R,S)-2-Butanol is commonly found as a racemic mixture, and the products of its esterification are racemic mixtures too. This work is of great significance in the field of the enzymatic kinetic resolution due to the little information found in literature about the resolution of (R,S)-2-butanol as pure compound. So, this article is a contribution about the enzymatic resolution of (R,S)-2-butanol. The reaction here studied is the esterification/transesterification of (R,S)-2-butanol in organic media (n-hexane) using as biocatalyst the lipase Novozym 435®. The main target of this study is to analyze the influence of certain variables in this reaction. Some of these variables are acyl donor (acids and esters), concentration of substrates, enzyme/substrate ratio, and temperature. The main conclusions of this study are the positive effect of higher substrates concentration (1.5 M) and larger amount of enzyme (13.8 g mol(-1) substrate) on kinetic resolution rate but not a very noticeable effect on enantiomeric excesses. The longer the carboxylic acid chain is, the better results are obtained. Besides to achieve a satisfactory kinetic resolution, it is recommendable to select reaction times (180 min) at which the highest substrate enantiomeric excess is reached (~60%). The temperature has not an appreciable influence on the resolution in the range studied (40-60 °C). When an ester (vinyl acetate) is used as acyl donor, the resolution shows better results than when using a carboxylic acid as acyl donor (ee(s) ~90% at 90 min). Moreover, Michaelis-Menten parameters, v(max) and K(M), were determined, 0.04 mol l(-1) min(-1) and 0.41 mol l(-1), respectively.
Intermolecular chiral assemblies in R(-) and S(+) 2-butanol detected by microcalorimetry measurements
Chirality 2012 Jul;24(7):500-5.PMID:22570171DOI:10.1002/chir.22033.
Supramolecular chiral assemblies of R(-) and S(+) 2-butanol, in their neat form or when dissolved in their nonchiral isomer isobutanol, were evaluated by isothermal titration calorimetry (ITC) ensuing mixing. Dilution of 0.5 M solution of R(-) 2-butanol in isobutanol into the latter liberated heat of several calories per mole, which was approximately double than that obtained in parallel dilutions of S(+) 2-butanol in isobutanol. The ITC dilution profiles indicated an estimate of about 100 isobutanol solvent molecules surrounding each of the 2-butanol enantiomers, presumably arranged in chiral configurations, with different adopted order between the isomers. Mixings of neat R and S 2-butanol were followed by endothermic ITC profiles, indicating that, in racemic 2-butanol, both the supramolecular order and the intermolecular binding energies are lower than in each of the neat chiral isomers. The diversion from symmetrical ITC patterns in these mixings indicated again a subtle difference in molecular organization between the neat enantiomers. It should be noted that the presence of impurities, α-pinene and teterhydrofuran, at a level totaling 0.5%, did not influence the ITC heat flow profiles. The findings of this study demonstrate for the first time that chiral solutes in organic solvents are expected to acquire asymmetric solvent envelopes that may be different between the enantiomers, thus broadening this phenomenon beyond the previously demonstrated cases in aqueous solutions.
Enantioselective, continuous (R)- and (S)-2-butanol synthesis: achieving high space-time yields with recombinant E. coli cells in a micro-aqueous, solvent-free reaction system
J Biotechnol 2014 Dec 10;191:106-12.PMID:25036751DOI:10.1016/j.jbiotec.2014.06.032.
The stereoselective production of (R)- or (S)-2-butanol is highly challenging. A potent synthesis strategy is the biocatalytic asymmetric reduction of 2-butanone applying alcohol dehydrogenases. However, due to a time-dependent racemisation process, high stereoselectivity is only obtained at incomplete conversion after short reaction times. Here, we present a solution to this problem: by using a continuous process, high biocatalytic selectivity can be achieved while racemisation is suppressed successfully. Furthermore, high conversion was achieved by applying recombinant, lyophilised E. coli cells hosting Lactobacillus brevis alcohol dehydrogenase in a micro-aqueous solvent-free continuous reaction system. The optimisation of residence time (τ) and 2-butanone concentration boosted both conversion (>99%) and enantiomeric excess (ee) of (R)-2-butanol (>96%). When a residence time of only τ=3.1 min was applied, productivity was extraordinary with a space-time yield of 2278±29g/(L×d), thus exceeding the highest values reported to date by a factor of more than eight. The use of E. coli cells overexpressing an ADH of complementary stereoselectivity yielded a synthesis strategy for (S)-2-butanol with an excellent ee (>98%). Although conversion was only moderate (up to 46%), excellent space-time yields of up to 461g/(L×d) were achieved. The investigated concept represents a synthesis strategy that can also be applied to other biocatalytic processes where racemisation poses a challenge.
Age-dependent changes in the ratio of (R)- and (S)-2-butanol released by virgin females of Dasylepida ishigakiensis (Coleoptera: Scarabaeidae)
Bull Entomol Res 2012 Dec;102(6):730-6.PMID:23146160DOI:10.1017/S0007485312000363.
The females of the white grub beetle, Dasylepida ishigakiensis, release two enantiomers of 2-butanol, (R)-2-butanol and (S)-2-butanol. The ratio describing the relative proportions of these two enantiomers (R/S ratio) has not yet been investigated. (R)-2-Butanol has been shown to attract males in laboratory and field experiments, whereas (S)-2-butanol tends to inhibit them. To determine the R/S ratio of the 2-butanol emitted by virgin females, we collected 2-butanol from young (53 days old), mature (63 days old) and old females (73 days old) using water, extracted with an SPME fibre and subsequently injected into GC-MS. The major component of the 2-butanol emitted by the young females was (R)-2-butanol, but as the females aged, the component ratio favoured (S)-2-butanol. Young females released an 80:20 mixture of (R)- and (S)-2-butanol, whereas old females released a 45:55 mixture. The EAG response of male antennae to a 50:50 ratio (racemic mixture) showed a similar dose-response curve to that of (R)-2-butanol. The male orientation responses to (R)-2-butanol decreased when the relative proportion of (S)-2-butanol increased. An inhibitory and/or masking effect of (S)-2-butanol on male orientation behaviour was also observed in the flight tunnel assay. These results suggest that males are more strongly attracted to young females than to old females. We also discuss the possibility of using 2-butanol isomers as a control or monitoring agent for this insect.