Physicochemical Properties
| Molecular Formula | C34H66O4 |
| Molecular Weight | 538.89 |
| Exact Mass | 538.496 |
| CAS # | 1481636-41-2 |
| PubChem CID | 72190300 |
| Appearance | Solid powder |
| Density | 0.9±0.1 g/cm3 |
| Boiling Point | 619.2±38.0 °C at 760 mmHg |
| Flash Point | 177.3±20.3 °C |
| Vapour Pressure | 0.0±3.9 mmHg at 25°C |
| Index of Refraction | 1.466 |
| LogP | 14.66 |
| Hydrogen Bond Donor Count | 1 |
| Hydrogen Bond Acceptor Count | 4 |
| Rotatable Bond Count | 32 |
| Heavy Atom Count | 38 |
| Complexity | 505 |
| Defined Atom Stereocenter Count | 0 |
| SMILES | C(O)(=O)CCCC(OC(=O)CCCCCCCCCCCCCCC)CCCCCCCCCCCCC |
| InChi Key | QBGKCWKQYJQHJX-UHFFFAOYSA-N |
| InChi Code | InChI=1S/C34H66O4/c1-3-5-7-9-11-13-15-16-18-20-22-24-26-31-34(37)38-32(29-27-30-33(35)36)28-25-23-21-19-17-14-12-10-8-6-4-2/h32H,3-31H2,1-2H3,(H,35,36) |
| Chemical Name | 5-hexadecanoyloxyoctadecanoic acid |
| 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) |
Biological Activity
| ln Vitro | 5-PAHSA (30 μM, 12 hours) can reduce ROS levels and induce autophagy in PC12 cells[1]. 5-PAHSA (20 μM, 2 days) can reduce insulin resistance induced by high insulin and TNF-α in HepG2 cells and 3T3-L1 cells[3]. |
| ln Vivo | 5-PAHSA (50 and 150 mg/kg, oral gavage, 30 days) inhibits lipid peroxidation in DB/DB mice[1]. 5-PAHSA (45 mg/kg, oral gavage, 3 days) stimulates de novo lipogenesis and lipid remodeling in epididymal WAT (eWAT) during cold exposure in mice[2]. |
| References |
[1]. A novel palmitic acid hydroxy stearic acid (5-PAHSA) plays a neuroprotective role by inhibiting phosphorylation of the m-TOR-ULK1 pathway and regulating autophagy. CNS Neurosci Ther. 2021 Apr;27(4):484-496. [2]. Lipokine 5-PAHSA Is Regulated by Adipose Triglyceride Lipase and Primes Adipocytes for De Novo Lipogenesis in Mice. Diabetes. 2020 Mar;69(3):300-312. [3]. High Glucose Concentration Impairs 5-PAHSA Activity by Inhibiting AMP-Activated Protein Kinase Activation and Promoting Nuclear Factor-Kappa-B-Mediated Inflammation. Front Pharmacol. 2019 Jan 7;9:1491. |
| Additional Infomation | 5-PAHSA is a FAHFA obtained by formal condensation of the carboxy group of palmitic acid with the hydroxy group of 5-hydroxystearic acid. It has a role as a human metabolite, an anti-inflammatory agent and a hypoglycemic agent. It is a FAHFA and a long-chain fatty acid. It is functionally related to a hexadecanoic acid and an octadecanoic acid. It is a conjugate acid of a 5-PAHSA(1-). |
Solubility Data
| Solubility (In Vitro) | DMSO : 16.67 mg/mL (30.93 mM; with sonication (<80°C)) |
| Solubility (In Vivo) |
Solubility in Formulation 1: 1.67 mg/mL (3.10 mM) in 10% DMSO 40% PEG300 5% Tween-80 45% Saline (add these co-solvents sequentially from left to right, and one by one), clear solution; ultrasonic dissolution can obtain a clear solution of 1.67 mg/mL. For example, if 1 mL of working solution, add 100 μL of 16.7 mg/mL clear DMSO stock solution to 400 μL PEG300 and mix well; then add 50 μL Tween-80 to the above system and mix well; then add 450 μL saline to make it 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: 1.67 mg/mL (3.10 mM) in 10% DMSO 90% Corn Oil (add these co-solvents sequentially from left to right, and one by one), clear solution; sonication aided dissolution. For example, if 1 mL of working solution, add 100 μL of 16.7 mg/mL clear DMSO stock solution to 900 μL corn oil and mix well. (Please use freshly prepared in vivo formulations for optimal results.) |
| Preparing Stock Solutions | 1 mg | 5 mg | 10 mg | |
| 1 mM | 1.8557 mL | 9.2783 mL | 18.5567 mL | |
| 5 mM | 0.3711 mL | 1.8557 mL | 3.7113 mL | |
| 10 mM | 0.1856 mL | 0.9278 mL | 1.8557 mL |