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Jalapinolic acid is a novel and potent hydroxypalmitic acid
| Targets |
Natural product
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|---|---|
| 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]
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| 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] |
| Molecular Formula |
C16H32O3
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|---|---|
| Molecular Weight |
272.420
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| Exact Mass |
272.235
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| Elemental Analysis |
C, 70.54; H, 11.84; O, 17.62
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| CAS # |
502-75-0
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| PubChem CID |
3013895
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| Appearance |
Typically exists as solid at room temperature
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| Density |
0.955g/cm3
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| Boiling Point |
409.4ºC at 760 mmHg
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| Flash Point |
215.6ºC
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| Index of Refraction |
1.467
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| LogP |
4.523
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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 |
19
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| Complexity |
204
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| Defined Atom Stereocenter Count |
0
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| SMILES |
CCCCCC(CCCCCCCCCC(=O)O)O
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| InChi Key |
YNQGVRJFSHTULP-UHFFFAOYSA-N
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| 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)
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| Chemical Name |
11-hydroxyhexadecanoic acid
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| 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-
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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 | 3.6708 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 |
*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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