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| Targets |
(S)-1,1'-Bi-2,2'-naphthol (BINOL) is a chiral ligand and biochemical reagent rather than a direct pharmacological agent. As a ligand, it does not have specific biological receptors as its primary targets. Its mechanism of action in asymmetric synthesis involves coordination to metal centers (e.g., aluminum, titanium, boron) to form chiral catalysts that induce enantioselectivity in various organic transformations, including asymmetric hydrogenation, epoxidation, and allylation. The compound's axial chirality and C2 symmetry are essential for its enantioselective induction properties.
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| ln Vitro |
In vitro, (S)-1,1'-bi-2,2'-naphthol is used as a chiral ligand in asymmetric synthesis for the preparation of enantiomerically pure compounds. It is a valuable biochemical reagent for life science research, including pharmaceutical synthesis. Cellular assays are not typically performed with this compound as a direct cell-modulating agent, as its primary applications are in asymmetric catalysis and organic synthesis. The compound's ability to induce enantioselectivity makes it valuable for synthesizing chiral pharmaceutical intermediates.
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| ln Vivo |
In vivo data for (S)-1,1'-bi-2,2'-naphthol is limited, as it is primarily a research reagent and chiral ligand. The compound is classified for research use only and is not intended for human or veterinary therapeutic applications. Its primary applications are in asymmetric synthesis and pharmaceutical research rather than as a therapeutic agent. The compound's phenolic structure suggests potential for metabolic conjugation if administered systemically. Specific in vivo data for the parent compound is not available in the public literature.
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| Enzyme Assay |
In vitro enzyme/receptor binding assays for (S)-1,1'-bi-2,2'-naphthol are not typically performed, as it is primarily a chiral ligand. The compound is used in asymmetric synthesis to prepare enantiomerically pure compounds. A typical assay involves using the compound as a chiral ligand in metal-catalyzed reactions. The compound is dissolved in organic solvents such as THF or dichloromethane. Reaction progress is monitored by TLC, GC, or HPLC. Enantioselectivity is evaluated by chiral HPLC or polarimetry. The compound's ability to induce enantioselectivity is assessed by the enantiomeric excess of the product.
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| Cell Assay |
Cellular assays for (S)-1,1'-bi-2,2'-naphthol are not standard, as the compound is primarily used as a chiral ligand in asymmetric synthesis rather than as a cell-modulating agent. The compound's phenolic structure suggests potential for cytotoxicity at high concentrations. Any cellular studies would focus on evaluating the compound's cytotoxicity. A typical protocol would involve culturing appropriate cell lines in growth medium at 37°C with 5% CO₂. Cells would be treated with varying concentrations of the compound. Cell viability would be assessed using MTT or similar assays.
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| Animal Protocol |
In vivo animal studies for (S)-1,1'-bi-2,2'-naphthol are not standard, as it is a research reagent and chiral ligand rather than a therapeutic candidate. The compound is classified for research use only and is not intended for human or veterinary applications. Any animal studies would be limited to toxicological evaluations of the compound as an industrial chemical. The compound's phenolic structure suggests potential for toxicity. Specific in vivo protocols are not available in the public literature.
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| ADME/Pharmacokinetics |
Pharmacokinetic data for (S)-1,1'-bi-2,2'-naphthol is limited, as it is primarily a research reagent. The compound has a molecular weight of 286.32 g/mol and a molecular formula of C₂₀H₁₄O₂. It is a solid at room temperature with a melting point of 208°C. It is stored at 2-8°C. As a phenolic compound, it may undergo metabolic conjugation (glucuronidation, sulfation) and oxidation. Specific ADME data is not available. The compound is soluble in dioxane (50 mg/mL).
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| Toxicity/Toxicokinetics |
(S)-1,1'-Bi-2,2'-naphthol is classified for research use only and is not intended for human or veterinary applications. Standard safety precautions include handling with appropriate personal protective equipment (gloves, lab coat, safety goggles) in a well-ventilated area. The compound should be stored at 2-8°C away from incompatible materials. Acute toxicity data is not readily available in the public literature. As with all research chemicals, appropriate laboratory safety practices should be followed. No specific LD₅₀ values are available in the public domain.
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| Additional Infomation |
(S)-(-)-1,1'-bi-2-naphthol is a member of the naphthol family.
(S)-1,1'-Bi-2,2'-naphthol (S-(-)-2,2'-Dihydroxy-1,1'-binaphthyl, CAS 18531-99-2) is a chiral biochemical reagent with the molecular formula C₂₀H₁₄O₂. It is a chiral ligand widely used in asymmetric synthesis for the preparation of enantiomerically pure compounds. The compound has a specific rotation of -36.7° (c=1.00g/100ml THF) and a melting point of 208°C. It is classified as a research-use-only compound and is available from multiple commercial suppliers. |
| Molecular Formula |
C20H14O2
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|---|---|
| Molecular Weight |
286.32
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| Exact Mass |
286.099
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| CAS # |
18531-99-2
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| PubChem CID |
11762
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| Appearance |
White to off-white solid powder
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| Density |
1 g/cm3
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| Melting Point |
215-218 °C
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| Index of Refraction |
-36.0 ° (C=1， THF)
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| LogP |
5.071
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| Hydrogen Bond Donor Count |
2
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| Hydrogen Bond Acceptor Count |
2
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| Rotatable Bond Count |
1
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| Heavy Atom Count |
22
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| Complexity |
346
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| Defined Atom Stereocenter Count |
0
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| SMILES |
O([H])C1C([H])=C([H])C2=C([H])C([H])=C([H])C([H])=C2C=1C1=C(C([H])=C([H])C2=C([H])C([H])=C([H])C([H])=C12)O[H]
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| InChi Key |
PPTXVXKCQZKFBN-UHFFFAOYSA-N
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| InChi Code |
InChI=1S/C20H14O2/c21-17-11-9-13-5-1-3-7-15(13)19(17)20-16-8-4-2-6-14(16)10-12-18(20)22/h1-12,21-22H
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| Chemical Name |
1-(2-hydroxynaphthalen-1-yl)naphthalen-2-ol
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| HS Tariff Code |
2934.99.9001
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| Storage |
Powder -20°C 3 years 4°C 2 years In solvent -80°C 6 months -20°C 1 month |
| Shipping Condition |
Room temperature (This product is stable at ambient temperature for a few days during ordinary shipping and time spent in Customs)
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| Solubility (In Vitro) |
May dissolve in DMSO (in most cases), if not, try other solvents such as H2O, Ethanol, or DMF with a minute amount of products to avoid loss of samples
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| Solubility (In Vivo) |
Note: Listed below are some common formulations that may be used to formulate products with low water solubility (e.g. < 1 mg/mL), you may test these formulations using a minute amount of products to avoid loss of samples.
Injection Formulations
Injection Formulation 1: DMSO : Tween 80： Saline = 10 : 5 : 85 (i.e. 100 μL DMSO stock solution → 50 μL Tween 80 → 850 μL Saline)(e.g. IP/IV/IM/SC) *Preparation of saline: Dissolve 0.9 g of sodium chloride in 100 mL ddH ₂ O to obtain a clear solution. Injection Formulation 2: DMSO : PEG300 ：Tween 80 : Saline = 10 : 40 : 5 : 45 (i.e. 100 μL DMSO → 400 μLPEG300 → 50 μL Tween 80 → 450 μL Saline) Injection Formulation 3: DMSO : Corn oil = 10 : 90 (i.e. 100 μL DMSO → 900 μL Corn oil) Example: Take the Injection Formulation 3 (DMSO : Corn oil = 10 : 90) as an example, if 1 mL of 2.5 mg/mL working solution is to be prepared, you can take 100 μL 25 mg/mL DMSO stock solution and add to 900 μL corn oil, mix well to obtain a clear or suspension solution (2.5 mg/mL, ready for use in animals). View More
Injection Formulation 4: DMSO : 20% SBE-β-CD in saline = 10 : 90 [i.e. 100 μL DMSO → 900 μL (20% SBE-β-CD in saline)] Oral Formulations
Oral Formulation 1: Suspend in 0.5% CMC Na (carboxymethylcellulose sodium) Oral Formulation 2: Suspend in 0.5% Carboxymethyl cellulose Example: Take the Oral Formulation 1 (Suspend in 0.5% CMC Na) as an example, if 100 mL of 2.5 mg/mL working solution is to be prepared, you can first prepare 0.5% CMC Na solution by measuring 0.5 g CMC Na and dissolve it in 100 mL ddH2O to obtain a clear solution; then add 250 mg of the product to 100 mL 0.5% CMC Na solution, to make the suspension solution (2.5 mg/mL, ready for use in animals). View More
Oral Formulation 3: Dissolved in PEG400 (Please use freshly prepared in vivo formulations for optimal results.) |
| Preparing Stock Solutions | 1 mg | 5 mg | 10 mg | |
| 1 mM | 3.4926 mL | 17.4630 mL | 34.9260 mL | |
| 5 mM | 0.6985 mL | 3.4926 mL | 6.9852 mL | |
| 10 mM | 0.3493 mL | 1.7463 mL | 3.4926 mL |
*Note: Please select an appropriate solvent for the preparation of stock solution based on your experiment needs. For most products, DMSO can be used for preparing stock solutions (e.g. 5 mM, 10 mM, or 20 mM concentration); some products with high aqueous solubility may be dissolved in water directly. Solubility information is available at the above Solubility Data section. Once the stock solution is prepared, aliquot it to routine usage volumes and store at -20°C or -80°C. Avoid repeated freeze and thaw cycles.
Calculation results
Working concentration： mg/mL；
Method for preparing DMSO stock solution： mg drug pre-dissolved in μL DMSO (stock solution concentration mg/mL). Please contact us first if the concentration exceeds the DMSO solubility of the batch of drug.
Method for preparing in vivo formulation:：Take μL DMSO stock solution, next add μL PEG300, mix and clarify, next addμL Tween 80, mix and clarify, next add μL ddH2O，mix and clarify.
(1) Please be sure that the solution is clear before the addition of next solvent. Dissolution methods like vortex, ultrasound or warming and heat may be used to aid dissolving.
(2) Be sure to add the solvent(s) in order.
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