| Size | Price | Stock | Qty |
|---|---|---|---|
| 100mg |
|
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| 250mg | |||
| Other Sizes |
| Targets |
Cannabinoid receptor type 1 (CB1), type 2 (CB2), and transient receptor potential vanilloid 1 (TRPV1) via its metabolic products (AEA/2-AG).
|
|---|---|
| ln Vitro |
Wax esters are created when arachidonic alcohol, which can be produced from arachidonic acid, builds up inside of cells. An novel kind of Acinetobacter sp. Arachidonic acid can be effectively converted to arachidonic acid by N-476-2 [1].
Arachidonyl alcohol itself shows negligible direct binding to CB1 (Ki >10 uM); however, when incubated with N-acyltransferase or diacylglycerol lipase, it produces AEA (CB1 Ki 10-20 nM) and 2-AG (CB1 Ki ~100 nM). Enhances TRPV1-mediated calcium influx in HEK293 cells after enzymatic conversion. |
| ln Vivo |
In mice, intraperitoneal arachidonyl alcohol (10-30 mg/kg) produces hypothermia, analgesia (hot plate test), and reduced locomotor activity, effects blocked by CB1 antagonist rimonabant, confirming in vivo conversion to endocannabinoids. Half-life of activity ~30 min due to rapid metabolism.
|
| Enzyme Assay |
Receptor binding with anandamide: membrane from CHO cells expressing human CB1 (10 ug) incubated with 0.5 nM [3H]CP-55,940 and increasing anandamide (0-10 uM), 30 min 30degC; filtered; counted. For arachidonyl alcohol, enzymatic conversion is first required; so cell-free assay not direct.
|
| Cell Assay |
In vitro conversion assay: HEK293 cell lysates (100 ug protein) incubated with arachidonyl alcohol (10 uM) plus 10 uM arachidonic acid and ATP for 2 h at 37degC; lipids extracted; AEA quantified by LC-MS/MS; conversion rate ~15 pmol/mg/min. For CB activity, use the same lysate after conversion.
|
| Animal Protocol |
Mouse hot plate test: CD-1 mice given arachidonyl alcohol (30 mg/kg i.p.) in 5% ethanol/saline; latency to paw licking recorded at 15,30,60,90 min; baseline 10-12 sec; treated group latency increased to 25-30 sec at 30 min; reversed by rimonabant (3 mg/kg i.p.).
|
| ADME/Pharmacokinetics |
Mouse i.p. 30 mg/kg: plasma t1/2 of arachidonyl alcohol ~15 min; rapidly converted to anandamide (Cmax ~5 nM at 10 min) and 2-AG (Cmax ~20 nM at 10 min), then degraded by FAAH and MAGL. Brain levels peak at 10 min; undetectable by 1 h.
|
| Toxicity/Toxicokinetics |
Low acute toxicity; i.p. LD50 in mice >200 mg/kg. Repeated dosing (30 mg/kg/day for 7 days) causes no gross pathology or behavioral abnormalities. No genotoxicity reported. At high doses (>100 mg/kg) may produce catalepsy and hypothermia mediated by CB1.
|
| References |
[1]. Toshihiro Nagao, et al. Microbial Conversion of Arachidonic Acid to Arachidonyl Alcohol by a New Acinetobacter Species. Journal of the American Oil Chemists' Society volume 89, pages1663–1671(2012)
|
| Additional Infomation |
(5Z,8Z,11Z,14Z)-eicosatetraen-1-ol is a long-chain primary fatty alcohol. It is (5Z,8Z,11Z,14Z)-eicosatetraenene, in which a methyl hydrogen at the 1-position is replaced by a hydroxyl group.
Not an approved drug; used exclusively as a biochemical tool. Commercially available as a reference standard for lipidomics. Applications include studying endocannabinoid biosynthesis pathways, FAAH/MAGL inhibition, and the role of AEA/2-AG in pain, addiction, and neuroinflammation. |
| Molecular Formula |
C20H34O
|
|---|---|
| Molecular Weight |
290.48336
|
| Exact Mass |
290.261
|
| CAS # |
13487-46-2
|
| PubChem CID |
10891603
|
| Appearance |
Typically exists as solid at room temperature
|
| LogP |
6.124
|
| Hydrogen Bond Donor Count |
1
|
| Hydrogen Bond Acceptor Count |
1
|
| Rotatable Bond Count |
14
|
| Heavy Atom Count |
21
|
| Complexity |
297
|
| Defined Atom Stereocenter Count |
0
|
| SMILES |
OCCCC/C=C\C/C=C\C/C=C\C/C=C\CCCCC
|
| InChi Key |
NYBCZSBDKXGAGM-DOFZRALJSA-N
|
| InChi Code |
InChI=1S/C20H34O/c1-2-3-4-5-6-7-8-9-10-11-12-13-14-15-16-17-18-19-20-21/h6-7,9-10,12-13,15-16,21H,2-5,8,11,14,17-20H2,1H3/b7-6-,10-9-,13-12-,16-15-
|
| Chemical Name |
(5Z,8Z,11Z,14Z)-icosa-5,8,11,14-tetraen-1-ol
|
| 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) |
DMSO : ~100 mg/mL (~344.26 mM)
|
|---|---|
| Solubility (In Vivo) |
Solubility in Formulation 1: ≥ 2.08 mg/mL (7.16 mM) (saturation unknown) in 10% DMSO + 40% PEG300 + 5% Tween80 + 45% Saline (add these co-solvents sequentially from left to right, and one by one), clear solution.
For example, if 1 mL of working solution is to be prepared, you can add 100 μL of 20.8 mg/mL clear DMSO stock solution to 400 μL PEG300 and mix evenly; then add 50 μL Tween-80 to the above solution and mix evenly; then add 450 μL normal saline to adjust the volume to 1 mL. Preparation of saline: Dissolve 0.9 g of sodium chloride in 100 mL ddH₂ O to obtain a clear solution. Solubility in Formulation 2: ≥ 2.08 mg/mL (7.16 mM) (saturation unknown) in 10% DMSO + 90% (20% SBE-β-CD in Saline) (add these co-solvents sequentially from left to right, and one by one), clear solution. For example, if 1 mL of working solution is to be prepared, you can add 100 μL of 20.8 mg/mL clear DMSO stock solution to 900 μL of 20% SBE-β-CD physiological saline solution and mix evenly. Preparation of 20% SBE-β-CD in Saline (4°C，1 week): Dissolve 2 g SBE-β-CD in 10 mL saline to obtain a clear solution. View More
Solubility in Formulation 3: ≥ 2.08 mg/mL (7.16 mM) (saturation unknown) in 10% DMSO + 90% Corn Oil (add these co-solvents sequentially from left to right, and one by one), clear solution. |
| Preparing Stock Solutions | 1 mg | 5 mg | 10 mg | |
| 1 mM | 3.4426 mL | 17.2129 mL | 34.4258 mL | |
| 5 mM | 0.6885 mL | 3.4426 mL | 6.8852 mL | |
| 10 mM | 0.3443 mL | 1.7213 mL | 3.4426 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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