L-Valinol
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| Category | Others |
| Catalog number | BBF-05167 |
| CAS | 2026-48-4 |
| Molecular Weight | 103.16 |
| Molecular Formula | C5H13NO |
| Purity | ≥ 98 % |
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Description
L-valinol is used as a reagent for the synthesis of simple 1,3-thiazolidine-2-thione derivatives with fungicidal activity. L-Valinol is also used in clinical trials to synthesize small molecule inhibitors of MDM2-p53 protein-protein interaction (MDM2 inhibitors) for the treatment of cancer.
Specification
| Related CAS | 4276-09-9 (D-configuration) |
| Synonyms | L-2-Amino-3-methyl-1-butanol; (+)-(S)-Valinol; (+)-2-Amino-3-methyl-1-butanol; (+)-Valinol; (2S)-1-Hydroxy-3-methylbutan-2-amine; (2S)-2-Amino-3-methyl-1-butanol; (2S)-Valinol; (S)-(+)-2-Amino-3-methyl-1-butanol; (S)-(+)-Valinol; (S)-2-Amino-3-methyl-1-butanol; (S)-2-Amino-3-methylbutanol; (S)-Valinol; NSC 322922; [(S)-1-(Hydroxymethyl)-2-methylpropyl]amine |
| Storage | Store at 2-8 ℃ |
| IUPAC Name | (2S)-2-amino-3-methylbutan-1-ol |
| Canonical SMILES | CC(C)C(CO)N |
| InChI | InChI=1S/C5H13NO/c1-4(2)5(6)3-7/h4-5,7H,3,6H2,1-2H3/t5-/m1/s1 |
| InChI Key | NWYYWIJOWOLJNR-RXMQYKEDSA-N |
Properties
| Appearance | White low-melting solid |
| Boiling Point | 81 ℃ at 8 mmHg |
| Melting Point | 30-34 ℃ |
| Flash Point | 78ºC |
| Density | 0.926 g/mL at 25 ℃ |
| Solubility | Slightly soluble in DMSO, Methanol |
| LogP | 0.66230 |
Reference Reading
1. Synthesis and application of amino alcohol-derived chiral ionic liquids, as additives for enantioseparation in capillary electrophoresis
Xiaofei Ma, Yingxiang Du, Xiaodong Sun, Jie Liu, Zhifeng Huang J Chromatogr A. 2019 Sep 13;1601:340-349. doi: 10.1016/j.chroma.2019.04.040. Epub 2019 Apr 15.
In this study, three functionalized chiral ionic liquids (CILs) derived from l-valinol, l-prolinol and l-phenylalaninol, namely N,N,N-trimethyl-l-valinol-bis(trifluoromethanesulfon)imide ([TMLV]+[Tf2N]-, CIL1), N,N-dimethyl-l-prolinol-bis(trifluoromethanesulfon)imide ([DMLP]+[Tf2N]-, CIL2) and N,N,N-trimethyl-l-phenylalaninol-bis(trifluoromethanesulfon)imide ([TMLP]+[Tf2N]-, CIL3), were synthesized and subsequently utilized for enantiomeric separation in capillary electrophoresis (CE) with 2-hydroxypropyl-β-cyclodextrin (HP-β-CD) as chiral selector for the first time. Compared with traditional single HP-β-CD separation system, the synergistic system exhibited substantially improved separations of six tested drugs. Using the CIL1/HP-β-CD as a model system, the influence of crucial parameters including the type and proportion of organic modifier, CILs concentration, HP-β-CD concentration and buffer pH was investigated in detail. Additionally, molecular modeling with AutoDock was applied to elucidate the enhanced enantioselectivity in the presence of CILs, which has certain guiding value in predicting the migration order of the enantiomers and studying the interactions important for the chiral recognition.
2. Cations Controlling the Chiral Assembly of Luminescent Atomically Precise Copper(I) Clusters
Yan Jin, Si Li, Zhen Han, Bing-Jie Yan, Hai-Yang Li, Xi-Yan Dong, Shuang-Quan Zang Angew Chem Int Ed Engl. 2019 Aug 26;58(35):12143-12148. doi: 10.1002/anie.201906614. Epub 2019 Jul 25.
Chiral assembly and asymmetric synthesis are critically important for the generation of chiral metal clusters with chiroptical activities. Here, a racemic mixture of [K(CH3 OH)2 (18-crown-6)]+ [Cu5 (St Bu)6 ]- (1⋅CH3 OH) in the chiral space group was prepared, in which the chiral red-emissive anionic [Cu5 (St Bu)6 ]- cluster was arranged along a twofold screw axis. Interestingly, the release of the coordinated CH3 OH of the cationic units turned the chiral 1⋅CH3 OH crystal into a mesomeric crystal [K(18-crown-6)]+ [Cu5 (St Bu)6 ]- (1), which has a centrosymmetric space group, by adding symmetry elements of glide and mirror planes through both disordered [Cu5 (St Bu)6 ]- units. The switchable chiral/achiral rearrangement of [Cu5 (St Bu)6 ]- clusters along with the capture/release of CH3 OH were concomitant with an intense increase/decrease in luminescence. We also used cationic chiral amino alcohols to induce the chiral assembly of a pair of enantiomers, [d/l-valinol(18-crown-6)]+ [Cu5 (St Bu)6 ]- (d/l-Cu5V ), which display impressive circularly polarized luminescence (CPL) in contrast to the CPL-silent racemic mixture of 1⋅CH3 OH and mesomeric 1.
3. Quantification of structurally related aliphatic amino alcohols in l-valinol by hydrophilic interaction liquid chromatography separation combined with postcolumn derivatization and fluorescence detection
Michal Douša, Jan Stach, Petr Gibala, Karel Lemr J Sep Sci. 2016 Mar;39(5):851-6. doi: 10.1002/jssc.201501302. Epub 2016 Jan 28.
The amino alcohols in l-valinol were effectively separated and quantified using hydrophilic interaction chromatography with fluorescence detection. The influence of the mobile phase (salt type, buffer concentration, and pH) on retention was studied. A column TSKgel amide and mobile phase consisting of 10 mM acetate buffer pH 4.0 and acetonitrile (20:80, v/v) provided well-separated symmetric peaks of analytes. Fluorescence detection was performed using postcolumn derivatization with o-phtaldialdehyde/2-mercaptoethanol at an excitation and emission wavelength of 345 and 450 nm, respectively. Simple sample pretreatment and very high sensitivity represent the main advantages of the developed method. After validation, the method was successfully applied to the analysis of commercial samples of l-valinol.
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Bio Calculators
* Our calculator is based on the following equation:
Concentration (start) x Volume (start) = Concentration (final) x Volume (final)
It is commonly abbreviated as: C1V1 = C2V2
* Total Molecular Weight:
g/mol
Tip: Chemical formula is case sensitive. C22H30N4O √ c22h30n40 ╳
