| Size | Price | |
|---|---|---|
| 500mg | ||
| 1g | ||
| Other Sizes |
| Targets |
Based on available literature, the enantiomer 8(S)-HETE has been demonstrated to be a selective activator of peroxisome proliferator-activated receptor alpha (PPARα) and activates mouse skin protein kinase C (PKC) at concentrations as low as 0.3 µM. Based on structure-activity relationships among lipid mediators, 8(R)-HETE may exhibit similar receptor binding properties. Furthermore, 8(R)-HETE has been identified as a key signaling molecule in the induction of starfish oocyte maturation.
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|---|---|
| ln Vitro |
In vitro studies demonstrate that 8(R)-HETE effectively induces starfish oocyte maturation at concentrations as low as 0.071 μM. Notably, this bioactivity exhibits significant stereospecificity—8(S)-HETE shows negligible activity in this assay. The compound acts through 8(R)-HETE-dependent signaling pathways, with its precursor 8(R)-HpETE (8(R)-hydroperoxyeicosatetraenoic acid) identified as a putative intermediate in the biosynthesis of prostaglandins via the allene oxide synthase pathway in marine organisms. Additional studies suggest that 8(R)-HETE may share functional relevance with other HETE compounds such as 20-HETE, which has been shown to increase reactive oxygen species production in cardiomyocytes and stimulate L-type calcium channels through a protein kinase C-dependent mechanism.
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| ln Vivo |
Research on the in vivo activity of 8(R)-HETE primarily comes from marine biology studies. In the starfish oocyte maturation model, this compound exhibits significant in vivo bioactivity at sub-micromolar concentrations. As 8(R)-HETE is primarily produced in marine invertebrates, its in vivo pharmacological effects may differ across species. Related studies also indicate that HETE family members are involved in various cardiovascular functions including blood pressure regulation and vascular tone control, suggesting that 8(R)-HETE may play roles in similar physiological processes.
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| Enzyme Assay |
Cell-free assays for 8(R)-HETE can employ multiple analytical methods. A standard protocol includes: 1) Stereochemical assignment by chiral high-performance liquid chromatography (HPLC) coupled with UV detection, comparing retention times to published results for enantiomer configuration determination; 2) UV spectrophotometric detection at 237 nm wavelength, corresponding to the characteristic absorption maximum of its conjugated diene chromophore (molar extinction coefficient ε ≈ 27,000); 3) Quantitative analysis using liquid chromatography-tandem mass spectrometry (LC-MS/MS) with deuterated internal standards (e.g., d8-8-HETE); 4) For receptor binding studies, surface plasmon resonance or fluorescence polarization techniques can be used to evaluate interactions with nuclear receptors such as PPARα.
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| Cell Assay |
The in vitro cell assay protocol for 8(R)-HETE can be performed as follows: 1) Seed target cells (such as starfish oocytes, cardiomyocytes, or keratinocytes) in culture plates and culture at appropriate temperature; 2) Treat cells with various concentrations of 8(R)-HETE (typically ranging from 0.01-10 µM) for time periods determined by experimental objectives; 3) For starfish oocyte maturation assays, observe germinal vesicle breakdown as a marker of oocyte maturation; 4) For cell signaling studies, detect phosphorylation levels of signaling molecules including PKC, MAPK, and NF-κB by Western blot; 5) Observe cellular morphological changes and cell migration by fluorescence microscopy; 6) Detect intracellular reactive oxygen species levels using specific fluorescent probes. Include enantiomer controls such as 8(S)-HETE to assess stereospecificity.
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| Animal Protocol |
Published in vivo animal data for 8(R)-HETE are currently limited. Based on its characteristics as a bioactive marine lipid, potential research protocols could include: 1) Select appropriate model organisms (such as starfish, mice, or rats); 2) Administer 8(R)-HETE via intraperitoneal or intravenous injection at doses to be determined through preliminary experiments (reference concentrations 0.1-10 µM); 3) For starfish models, observe morphological indicators of oocyte maturation; 4) For mammalian models, measure cardiovascular parameters including blood pressure and heart rate, and detect plasma levels of inflammatory cytokines; 5) At study termination, euthanize animals and collect target tissues for histopathological examination; 6) Quantify 8(R)-HETE and its metabolite levels in tissues by LC-MS/MS.
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| ADME/Pharmacokinetics |
Systematic pharmacokinetic data for 8(R)-HETE are extremely limited in publicly available literature. This compound is typically supplied as a solution in ethanol and should be stored at -20°C to maintain stability. As an endogenous lipid mediator, its in vivo concentrations are regulated by multiple factors including substrate (arachidonic acid) availability and metabolic enzyme activities. 8(R)-HETE can be extracted and quantified from biological matrices (plasma, tissue homogenates, cell culture supernatants) using solid-phase extraction coupled with LC-MS/MS. This compound is classified as a dangerous good for transport and requires shipping on dry ice.
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| Toxicity/Toxicokinetics |
According to supplier Material Safety Data Sheets, 8(R)-HETE is classified as a dangerous good for transport, requiring additional shipping charges. This product is for research use only and is not intended for diagnostic, therapeutic, or human use. Systematic toxicological data for 8(R)-HETE, including acute toxicity, genotoxicity, and reproductive toxicity, have not been fully reported in publicly available literature. As an endogenous lipid mediator, it generally does not exhibit obvious cytotoxicity at physiological concentrations. However, at high concentrations, HETE family members may affect cellular function by inducing oxidative stress. Appropriate personal protective equipment should be used during handling and storage, following standard chemical safety practices.
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| References | |
| Additional Infomation |
8(R)-Hete is a HETE containing an (8R)-hydroxyl group and (5Z)-, (9E)-, (11Z)-, and (14Z)- double bonds. Functionally, it is associated with icosanoic acid (EPA)-5,9,11,14-tetraenoic acid. It is an enantiomer of 8(S)-HETE. 8(R)-HETE has been reported to be detected in Gersemia fruticosa, and relevant data are available.
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| Molecular Formula |
C20H32O3
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|---|---|
| Molecular Weight |
320.466286659241
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| Exact Mass |
320.235
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| CAS # |
105500-09-2
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| Related CAS # |
98462-03-4; 79495-84-4; 70968-93-3; 105500-09-2
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| PubChem CID |
5283163
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| Appearance |
Typically exists as solids at room temperature
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| Density |
1.0±0.1 g/cm3
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| Boiling Point |
471.1±45.0 °C at 760 mmHg
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| Flash Point |
252.8±25.2 °C
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| Vapour Pressure |
0.0±2.7 mmHg at 25°C
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| Index of Refraction |
1.514
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| LogP |
5.45
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| Hydrogen Bond Donor Count |
2
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| Hydrogen Bond Acceptor Count |
3
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| Rotatable Bond Count |
14
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| Heavy Atom Count |
23
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| Complexity |
392
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| Defined Atom Stereocenter Count |
1
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| SMILES |
O[C@@H](/C=C/C=C\C/C=C\CCCCC)C/C=C\CCCC(=O)O
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| InChi Key |
NLUNAYAEIJYXRB-GTYUHVKWSA-N
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| InChi Code |
InChI=1S/C20H32O3/c1-2-3-4-5-6-7-8-9-10-13-16-19(21)17-14-11-12-15-18-20(22)23/h6-7,9-11,13-14,16,19,21H,2-5,8,12,15,17-18H2,1H3,(H,22,23)/b7-6-,10-9-,14-11-,16-13+/t19-/m0/s1
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| Chemical Name |
(5Z,8R,9E,11Z,14Z)-8-hydroxyicosa-5,9,11,14-tetraenoic acid
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| Synonyms |
8(R)-HETE; 8R-HETE; 105500-09-2; (5Z,8R,9E,11Z,14Z)-8-hydroxyicosa-5,9,11,14-tetraenoic acid; CHEBI:34484; 8(R)-Hydroxyeicosatetraenoic acid
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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 | 3.1204 mL | 15.6021 mL | 31.2042 mL | |
| 5 mM | 0.6241 mL | 3.1204 mL | 6.2408 mL | |
| 10 mM | 0.3120 mL | 1.5602 mL | 3.1204 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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