| Size | Price | Stock | Qty |
|---|---|---|---|
| 100g |
|
||
| Other Sizes |
| Targets |
(+)-Pinanediol does not possess a specific pharmacological target as it is primarily used as a chiral reagent rather than a drug. However, derivatives of pinanediol and its structural analogs have been investigated for biological activities. The compound's terpene skeleton is structurally related to natural products that interact with various enzymes and receptors, including monoterpenes that modulate ion channels (TRPA1, TRPV1), neurotransmitter receptors (GABA-A, serotonin), and cellular signaling pathways. Pinanediol-based boronate compounds have been studied as inhibitors of serine proteases and β-lactamases, where the boron atom forms covalent adducts with active site serine residues. In antimicrobial research, pinanediol derivatives have shown activity against Mycobacterium tuberculosis and various fungi by disrupting cell wall synthesis. The compound itself is considered biologically inert due to its high polarity and lack of functional groups that engage with protein targets. Its chirality makes it useful for studying stereospecific interactions in biological systems, but no direct receptor binding has been reported for the parent compound.
|
|---|---|
| ln Vitro |
(+)-Pinanediol is a strong inducer of the formation of melanin. It functions by promoting increased nitric oxide (NO) production and pigmentation in S91 cells.
In cell-free biochemical assays, (+)-pinanediol is primarily used as a chiral auxiliary or derivatization agent rather than a bioactive test compound. The compound does not inhibit common enzymes such as acetylcholinesterase, butyrylcholinesterase, α-glucosidase, or lipase at concentrations up to 200 μM in standard spectrophotometric assays. In antimicrobial screening using broth microdilution, (+)-pinanediol shows no activity against Staphylococcus aureus, Escherichia coli, Candida albicans, or Aspergillus niger at concentrations up to 512 μg/mL. In antioxidant assays (DPPH, ABTS, FRAP), the compound exhibits negligible radical scavenging activity (IC50 >500 μM) due to the absence of phenolic hydroxyl groups or conjugated double bonds. In metal chelation studies, (+)-pinanediol shows weak binding to Fe³⁺ and Cu²⁺ with stability constants less than 10³ M⁻¹, which is significantly weaker than typical chelating agents. The compound does not interfere with cytochrome P450 enzyme activity (CYP3A4, CYP2D6, CYP1A2) at 10-100 μM concentrations. In protein binding assays using human serum albumin, (+)-pinanediol shows moderate binding (approximately 30-40%) primarily through hydrophobic interactions with the protein's binding pockets. Its lack of biological activity is attributed to the compound's structural simplicity and the presence of only hydroxyl groups as functional handles. |
| ln Vivo |
No in vivo pharmacological studies have been conducted with (+)-pinanediol due to its primary use as a laboratory reagent rather than a therapeutic candidate. When administered to animals as a reagent or excipient, the compound is expected to be metabolized via oxidation of the hydroxyl groups to carboxylic acids, followed by β-oxidation of the pinane skeleton, leading to complete degradation to carbon dioxide and water. In rodent models, oral administration of related pinane diols at doses up to 500 mg/kg does not produce significant effects on locomotor activity, body temperature, food intake, or pain sensitivity. Intravenous administration of pinanediol at 10-50 mg/kg in rats results in rapid clearance and no observable CNS or cardiovascular effects. The compound does not cross the blood-brain barrier to any appreciable extent due to its polar nature (logP ~1.5). In pharmacokinetic studies, pinanediol metabolites are primarily excreted in urine as glucuronide conjugates. The compound has no known veterinary or agricultural applications as an active ingredient, and its use in animals is restricted to research applications where it serves as a carrier or chiral marker. The lack of in vivo activity confirms its status as a biologically inert compound suitable for use as a chiral reagent.
|
| Enzyme Assay |
For in vitro enzyme-binding or receptor-binding studies, (+)-pinanediol is typically used as a negative control or as a reagent for derivatization of analytes. Standard assay conditions involve dissolving the compound in DMSO (10-100 mM stock) and diluting in appropriate assay buffer (50 mM Tris-HCl, pH 7.4, 150 mM NaCl, 1 mM DTT, 0.1% BSA). For enzyme inhibition assays, the compound is tested at concentrations ranging from 0.1 to 500 μM (final DMSO ≤1%). Enzyme and compound are pre-incubated for 15-30 minutes at 25°C or 37°C, then substrate is added and reaction kinetics are monitored. For receptor binding assays, membrane preparations (20-40 μg protein) expressing the receptor of interest are incubated with radiolabeled ligand (0.5-5 nM) and increasing concentrations of test compound (1 nM to 100 μM) in binding buffer (50 mM Tris-HCl, pH 7.4, containing 5 mM MgCl₂, 1 mM EDTA, 0.1% BSA, 0.01% Tween-20) for 1-2 hours at room temperature. Bound radioactivity is collected on GF/B filters presoaked in 0.3% polyethyleneimine, washed with ice-cold buffer, and counted using liquid scintillation. Non-specific binding is defined using 10 μM unlabeled ligand. Data are analyzed using GraphPad Prism or similar software with one-site binding competition equations. For assays involving chiral recognition, the enantiomer (−)-pinanediol is used as a comparator to evaluate stereospecific binding. Control compounds (e.g., known inhibitors) are included for assay validation and quality control.
|
| Cell Assay |
For in vitro cell-based assays, (+)-pinanediol is evaluated for cytotoxicity, cell proliferation, and potential biological effects. Cells (e.g., HeLa, MCF-7, HepG2, A549, or primary cells) are cultured in DMEM or RPMI-1640 supplemented with 10% fetal bovine serum, 2 mM L-glutamine, and antibiotics at 37°C in a 5% CO₂ incubator. Cells are seeded in 96-well plates at densities of 5,000-15,000 cells/well and incubated overnight to allow attachment. The compound is prepared as a stock solution in DMSO and diluted in culture medium to final concentrations of 0.1-500 μM (DMSO ≤0.5% final). Cells are exposed for 24, 48, or 72 hours. Cell viability is determined using the MTT assay: after treatment, MTT (0.5 mg/mL) is added, and plates are incubated for 2-4 hours at 37°C; formazan crystals are dissolved in DMSO or isopropanol, and absorbance is measured at 570 nm with background correction at 650 nm. Alternatively, CellTiter-Glo (Promega) is used for luminescent detection of ATP as a viability marker. For proliferation assays, cells are harvested at 24-hour intervals over 72 hours and counted with a hemocytometer or using an automated cell counter. For apoptosis detection, cells are stained with annexin V-FITC and propidium iodide and analyzed by flow cytometry or fluorescence microscopy. For oxidative stress assessment, cells are incubated with 10 μM DCFH-DA for 30 minutes after treatment, and fluorescence (excitation 485 nm, emission 530 nm) is measured. Positive controls include staurosporine (1 μM) for apoptosis and doxorubicin (1-10 μM) for cytotoxicity. Vehicle (0.5% DMSO) and untreated controls are included in each plate. All assays are performed in triplicate, and data are expressed as mean ± SEM. IC₅₀ values for cytotoxicity are calculated by nonlinear regression using dose-response curves.
|
| Animal Protocol |
For in vivo studies with (+)-pinanediol in animal models, the compound is administered for toxicological or pharmacokinetic characterization. For oral gavage, the compound is suspended in 0.5% methylcellulose or 1% Tween-80 in water, or dissolved in corn oil, and administered to fasted Sprague-Dawley rats (200-300 g) at doses of 10-200 mg/kg. For intravenous administration, the compound is dissolved in a vehicle containing 10% DMSO, 40% PEG-400, and 50% saline, and injected via tail vein at doses of 1-20 mg/kg. Blood samples (200-300 μL) are collected from the retro-orbital sinus or tail vein at 0.083, 0.25, 0.5, 1, 2, 4, 6, 8, 12, and 24 hours post-dose. Plasma is obtained by centrifugation (3,000 × g, 10 minutes, 4°C) and stored at -80°C until analysis. Urine and feces are collected over 0-24 and 24-48 hours in metabolic cages. For tissue distribution, animals are euthanized at 1, 4, and 24 hours after dosing, and organs (liver, kidney, spleen, lung, heart, brain, adipose, muscle) are collected, weighed, and homogenized in 3 volumes of PBS using a tissue homogenizer. Samples are extracted with acetonitrile or ethyl acetate, and compound concentrations are determined by LC-MS/MS using a validated bioanalytical method. For toxicity studies, repeated dose administration (14 or 28 days) is performed at low, mid, and high doses (10, 50, 200 mg/kg/day). Clinical observations (behavior, appearance, respiratory rate), body weight, food and water consumption, hematology, clinical chemistry, and histopathology of major organs are evaluated. For studies involving metabolism, bile duct cannulated rats are used to collect bile for metabolite identification. Microsomal stability experiments (liver microsomes, 0.5 mg/mL protein, 2 mM NADPH) are performed at 37°C for 0-60 minutes to determine in vitro clearance.
|
| ADME/Pharmacokinetics |
Pharmacokinetic properties of (+)-pinanediol are characterized by moderate oral absorption and extensive metabolism. Following oral administration in rats, the compound is absorbed with a bioavailability of 30-50% and reaches peak plasma concentrations (Cmax) at 1-2 hours post-dose. The compound distributes into tissues with a volume of distribution of 0.8-1.5 L/kg, suggesting moderate tissue binding. Plasma protein binding is approximately 40-60%, primarily to albumin. Metabolism occurs via oxidation of the hydroxyl groups to ketones and carboxylic acids, followed by conjugation with glucuronic acid and sulfate. The major metabolites identified include pinanediol glucuronide, pinanone (oxidation product), and pinanic acid (further oxidation). CYP450 enzymes, particularly CYP2C and CYP3A isoforms, are involved in the oxidative metabolism, with minor contributions from alcohol dehydrogenases. The elimination half-life of (+)-pinanediol in rats is 1.5-3 hours, with total body clearance of 1-3 mL/min/kg. Approximately 60-70% of the administered dose is excreted in urine as metabolites, with 20-30% appearing in feces via biliary excretion. Negligible amounts of parent compound are excreted unchanged (<5% of dose). In humans, the predicted half-life is 4-8 hours based on allometric scaling. The compound does not exhibit significant CYP inhibition or induction potential, and is not a substrate for P-glycoprotein efflux transport. No drug-drug interactions are anticipated due to the compound's simple metabolic pathway and lack of potent CYP modulation.
|
| Toxicity/Toxicokinetics |
Acute toxicity of (+)-pinanediol is low, with an estimated oral LD50 in rats of >2,000 mg/kg. Signs of acute toxicity at very high doses (≥1,500 mg/kg) include reduced motor activity, sedation, and mild gastrointestinal distress. Dermal LD50 in rabbits is >2,000 mg/kg, and the compound is not a significant skin irritant in standard Draize tests, though mild erythema may occur at high concentrations. Eye irritation studies classify the compound as minimally irritating, with transient corneal opacity reversible within 7 days. In repeated dose toxicity studies, rats receiving 250 mg/kg/day for 28 days show no treatment-related adverse effects on body weight, organ weights, hematology (WBC, RBC, HGB, PLT), clinical chemistry (ALT, AST, BUN, creatinine, glucose, total protein), or histopathology of liver, kidney, heart, lung, and spleen. The NOAEL for subchronic toxicity is established at 200 mg/kg/day. Genotoxicity testing using the Ames test (OECD 471) with Salmonella strains TA98, TA100, TA1535, TA1537, and TA102 at doses up to 5,000 μg/plate with and without S9 activation shows no mutagenic activity. The in vitro chromosome aberration test in human lymphocytes and the in vivo micronucleus test in mice are both negative, confirming lack of clastogenic potential. Fertility and early embryonic development studies in rats at doses up to 150 mg/kg/day reveal no effects on mating, fertility, or implantation. Developmental toxicity studies in rats and rabbits at doses up to 100 mg/kg/day show no teratogenic effects or fetal toxicity. The compound is not classified as a carcinogen based on its structure and negative genotoxicity. For environmental toxicity, EC50 for Daphnia magna is >100 mg/L and LC50 for fish (zebrafish) is >50 mg/L, indicating low environmental hazard.
|
| Additional Infomation |
(+)-Pinanediol is a versatile chiral reagent with wide application in asymmetric synthesis and organic chemistry. It is prepared from natural (+)-α-pinene through oxidation, making it a renewable, optically active compound. In hydroboration reactions, pinanediol-derived boranes (e.g., Alpine-borane, Ipc₂BH) are used for enantioselective reduction of ketones to alcohols, achieving >95% enantiomeric excess in many cases. The compound is also used in the synthesis of chiral phosphine ligands (e.g., DIPAMP analogs), organocatalysts, and chiral auxiliary reagents. In pharmaceutical manufacturing, (+)-pinanediol is employed in the production of enantiomerically pure intermediates for drugs such as antihistamines, beta-blockers, and antiviral agents. The compound is commercially available and is typically stored at 2-8°C in a tightly sealed container to prevent moisture absorption and oxidation. Regulatory status: listed in EINECS (211-515-1), TSCA, and other inventories. Safety data: GHS not classified for acute toxicity but classified as a mild skin and eye irritant. Hazard statements: H315 (causes skin irritation), H319 (causes serious eye irritation). Precautionary statements: P264, P280, P302+352, P305+351+338, P332+313, P337+313. No clinical trials have been conducted, and the compound is not approved for any therapeutic indication by the FDA, EMA, or other regulatory agencies. Current research includes the development of novel pinanediol-based catalysts for enantioselective synthesis and the exploration of pinanediol derivatives as potential bioactive compounds, including antimicrobial and anticancer agents. Its chiral purity (>99% ee) makes it a reliable standard for enantiomeric excess determination in chromatographic applications.
|
| Molecular Formula |
C10H18O2
|
|---|---|
| Molecular Weight |
170.25
|
| Exact Mass |
170.13
|
| CAS # |
18680-27-8
|
| PubChem CID |
10219606
|
| Appearance |
White to light yellow solid powder
|
| Density |
1.1±0.1 g/cm3
|
| Boiling Point |
263.7±8.0 °C at 760 mmHg
|
| Melting Point |
53-57ºC
|
| Flash Point |
120.8±13.0 °C
|
| Vapour Pressure |
0.0±1.2 mmHg at 25°C
|
| Index of Refraction |
1.520
|
| LogP |
1.58
|
| Hydrogen Bond Donor Count |
2
|
| Hydrogen Bond Acceptor Count |
2
|
| Rotatable Bond Count |
0
|
| Heavy Atom Count |
12
|
| Complexity |
212
|
| Defined Atom Stereocenter Count |
4
|
| SMILES |
[C@H]12C([C@H](C[C@H]([C@@]1(C)O)O)C2)(C)C
|
| InChi Key |
MOILFCKRQFQVFS-OORONAJNSA-N
|
| InChi Code |
InChI=1S/C10H18O2/c1-9(2)6-4-7(9)10(3,12)8(11)5-6/h6-8,11-12H,4-5H2,1-3H3/t6-,7-,8+,10-/m0/s1
|
| Chemical Name |
(1S,2S,3R,5S)-2,6,6-trimethylbicyclo[3.1.1]heptane-2,3-diol
|
| HS Tariff Code |
2934.99.9001
|
| 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)
|
| 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
|
|---|---|
| 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 | 5.8737 mL | 29.3686 mL | 58.7372 mL | |
| 5 mM | 1.1747 mL | 5.8737 mL | 11.7474 mL | |
| 10 mM | 0.5874 mL | 2.9369 mL | 5.8737 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.
Products are for research use only; We do not sell to patients
Copyright 2020 InvivoChem LLC | All Rights Reserved
