Physicochemical Properties
| Molecular Formula | C18H34O2 |
| Exact Mass | 282.255 |
| CAS # | 506-17-2 |
| Related CAS # | trans-Vaccenic acid;693-72-1;cis-Vaccenic acid-d13 |
| PubChem CID | 5282761 |
| Appearance | Colorless to light yellow liquid |
| Density | 0.9±0.1 g/cm3 |
| Boiling Point | 398.2±11.0 °C at 760 mmHg |
| Melting Point | 14-15ºC(lit.) |
| Flash Point | 295.0±14.4 °C |
| Vapour Pressure | 0.0±2.0 mmHg at 25°C |
| Index of Refraction | 1.467 |
| LogP | 7.7 |
| Hydrogen Bond Donor Count | 1 |
| Hydrogen Bond Acceptor Count | 2 |
| Rotatable Bond Count | 15 |
| Heavy Atom Count | 20 |
| Complexity | 234 |
| Defined Atom Stereocenter Count | 0 |
| SMILES | CCCCCC/C=C\CCCCCCCCCC(=O)O |
| InChi Key | UWHZIFQPPBDJPM-FPLPWBNLSA-N |
| InChi Code | InChI=1S/C18H34O2/c1-2-3-4-5-6-7-8-9-10-11-12-13-14-15-16-17-18(19)20/h7-8H,2-6,9-17H2,1H3,(H,19,20)/b8-7- |
| Chemical Name | (Z)-octadec-11-enoic 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 | cis-Vaccenic acid (CVA) at concentrations of 50 μM, 70 μM, and 100 μM stimulates the production of gamma globin and causes differentiation in K562, JK1, and transgenic mouse erythroid progenitor stem cells[2]. Additionally, the proportion of JK-1 cells positive for benzidine was raised by 50 μM of cis-Vaccenic acid[2]. cis-Vaccenic acid |
| Cell Assay |
Cell Differentiation Assay[2] Cell Types: K562 cells Tested Concentrations: 50 μM, 70 μM and 100 μM Incubation Duration: 48 and 120 hrs (hours) Experimental Results: Induced differentiation appeared to be concentration dependent in K562 cells with 50 μM CVA being the most effective concentration with more than 20% of the K562 cells showing positive for Benzidine stain after 48 h of incubation with CVA. |
| References |
[1]. Inactivation of T5 phage by cis-vaccenic acid, an antivirus substance from Rhodopseudomonas capsulata, and by unsaturated fatty acids and related alcohols. FEMS Microbiol Lett. 1991 Jan 1;61(1):13-7. [2]. Cis-vaccenic acid induces differentiation and up-regulates gamma globin synthesis in K562, JK1 and transgenic mice erythroid progenitor stem cells. Eur J Pharmacol. 2016 Apr 5;776:9-18. |
| Additional Infomation |
Cis-vaccenic acid is the cis isomer of vaccenic acid. It is a conjugate acid of a cis-vaccenate(1-). Vaccenic acid is a metabolite found in or produced by Escherichia coli (strain K12, MG1655). cis-Vaccenic acid has been reported in Agaricus blazei, Phormidium tenue, and other organisms with data available. See also: Cod Liver Oil (part of); Krill oil (part of); Oleic Acid (annotation moved to). |
Solubility Data
| Solubility (In Vitro) | DMSO : ≥ 50 mg/mL (177.02 mM) |
| 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.) |