Jalapinolic acid is a novel and potent hydroxypalmitic acid
Physicochemical Properties
| Molecular Formula | C16H32O3 |
| Molecular Weight | 272.420 |
| Exact Mass | 272.235 |
| Elemental Analysis | C, 70.54; H, 11.84; O, 17.62 |
| CAS # | 502-75-0 |
| PubChem CID | 3013895 |
| Appearance | Typically exists as solid at room temperature |
| Density | 0.955g/cm3 |
| Boiling Point | 409.4ºC at 760 mmHg |
| Flash Point | 215.6ºC |
| Index of Refraction | 1.467 |
| LogP | 4.523 |
| Hydrogen Bond Donor Count | 2 |
| Hydrogen Bond Acceptor Count | 3 |
| Rotatable Bond Count | 14 |
| Heavy Atom Count | 19 |
| Complexity | 204 |
| Defined Atom Stereocenter Count | 0 |
| SMILES | CCCCCC(CCCCCCCCCC(=O)O)O |
| InChi Key | YNQGVRJFSHTULP-UHFFFAOYSA-N |
| InChi Code | InChI=1S/C16H32O3/c1-2-3-9-12-15(17)13-10-7-5-4-6-8-11-14-16(18)19/h15,17H,2-14H2,1H3,(H,18,19) |
| Chemical Name | 11-hydroxyhexadecanoic acid |
| Synonyms | Jalapinolic acid; 11-Hydroxyhexadecanoic acid; Jalapinolic acid; 11-Hydroxyhexadecanoic acid; 502-75-0; Hexadecanoic acid, 11-hydroxy-; Jalapinoic acid; Builic acid; 11-hydroxy palmitic acid; 11-hydroxy-hexadecanoic acid; Hexadecanoic acid, 11-hydroxy- |
| 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
| Targets | Natural product |
| ln Vitro | Three new phenolic compounds, acutacoside C (1), acutacoside D (2) and acutacoside E (3) were isolated from the aerial part of Argyreia acuta. The oligosaccharide chain was composed of two glucoses and three rhamnoses, and the aglycone was (11S)-hydroxyhexadecanoic acid (jalapinolic acid). The core of the three compounds was operculinic acid B, which was rare in resin glycosides. Their structures were established by a combination of spectroscopic and chemical methods. Compounds 1-3 have been evaluated for inhibitory activity against α-glucosidase, which all showed weak inhibitory activities. [1] |
| References |
[1]. Three new resin glycosides compounds from Argyreia acuta and their α-glucosidase inhibitory activity. Nat Prod Res. 2017 Mar;31(5):537-542. [2]. https://pubmed.ncbi.nlm.nih.gov/?term=Jalapinolic+acid&sort=date [3]. The structures of convolvulinolic and jalapinolic acids. Synthesis of 11-hydroxypentadecanoic and 11-hydroxyhexadecanoic acids[J]. Journal of the American Chemical Society, 1928, 50(6): 1749-1755. |
| Additional Infomation |
11-hydroxy palmitic acid is a long-chain fatty acid.
1. 11-Hydroxyhexadecanoic acid and 11-hydroxypentadecanoic acid have been synthesized by the condensation of methyl 10-aldehydodecanoate with n-amyl magnesium bromide and n-butyl magnesium bromide, respectively, and subsequent saponification of the esters obtained. 2. Jalapinolic acid has been shown to be the d-form of 11-hydroxy - hexadecanoic acid. This has been accomplished through oxidation of both substances to the same keto acid, and also by the reduction of the keto acid derived from jalapinolic acid to a substance identical with the synthetic 11-hydroxyhexadecanoic acid. 3. Convolvulinolic acid has been shown to have a structure different from that of 11-hydroxypentadecanoic acid. The procedure used in investigating this substance was identical with that used in the study of jalapinolic acid.[3] |
Solubility Data
| 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 (e.g. IP/IV/IM/SC) Injection Formulation 1: DMSO : Tween 80： Saline = 10 : 5 : 85 (i.e. 100 μL DMSO stock solution → 50 μL Tween 80 → 850 μL Saline) *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). 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)] *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. Injection Formulation 5: 2-Hydroxypropyl-β-cyclodextrin : Saline = 50 : 50 (i.e. 500 μL 2-Hydroxypropyl-β-cyclodextrin → 500 μL Saline) Injection Formulation 6: DMSO : PEG300 : castor oil : Saline = 5 : 10 : 20 : 65 (i.e. 50 μL DMSO → 100 μLPEG300 → 200 μL castor oil → 650 μL Saline) Injection Formulation 7: Ethanol : Cremophor : Saline = 10： 10 : 80 (i.e. 100 μL Ethanol → 100 μL Cremophor → 800 μL Saline) Injection Formulation 8: Dissolve in Cremophor/Ethanol (50 : 50), then diluted by Saline Injection Formulation 9: EtOH : Corn oil = 10 : 90 (i.e. 100 μL EtOH → 900 μL Corn oil) Injection Formulation 10: EtOH : PEG300：Tween 80 : Saline = 10 : 40 : 5 : 45 (i.e. 100 μL EtOH → 400 μLPEG300 → 50 μL Tween 80 → 450 μL 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). Oral Formulation 3: Dissolved in PEG400 Oral Formulation 4: Suspend in 0.2% Carboxymethyl cellulose Oral Formulation 5: Dissolve in 0.25% Tween 80 and 0.5% Carboxymethyl cellulose Oral Formulation 6: Mixing with food powders Note: Please be aware that the above formulations are for reference only. InvivoChem strongly recommends customers to read literature methods/protocols carefully before determining which formulation you should use for in vivo studies, as different compounds have different solubility properties and have to be formulated differently. (Please use freshly prepared in vivo formulations for optimal results.) |
| Preparing Stock Solutions | 1 mg | 5 mg | 10 mg | |
| 1 mM | 3.6708 mL | 18.3540 mL | 36.7080 mL | |
| 5 mM | 0.7342 mL | 3.6708 mL | 7.3416 mL | |
| 10 mM | 0.3671 mL | 1.8354 mL | 3.6708 mL |