-Coriolic acid (13(S)-HODE) Chemical Structure.png)
Physicochemical Properties
| Molecular Formula | C18H32O3 |
| Molecular Weight | 296.44488 |
| Exact Mass | 296.235 |
| Elemental Analysis | C, 72.93; H, 10.88; O, 16.19 |
| CAS # | 29623-28-7 |
| Related CAS # | 198123-90-9 (ethanolamide); 29623-28-7 |
| PubChem CID | 6443013 |
| Appearance | Colorless to light yellow liquid |
| Density | 1.0±0.1 g/cm3 |
| Boiling Point | 422.7±20.0 °C at 760 mmHg |
| Flash Point | 223.6±18.3 °C |
| Vapour Pressure | 0.0±2.3 mmHg at 25°C |
| Index of Refraction | 1.492 |
| LogP | 5.32 |
| Hydrogen Bond Donor Count | 2 |
| Hydrogen Bond Acceptor Count | 3 |
| Rotatable Bond Count | 14 |
| Heavy Atom Count | 21 |
| Complexity | 295 |
| Defined Atom Stereocenter Count | 1 |
| SMILES | CCCCC[C@@H](/C=C/C=C\CCCCCCCC(=O)O)O |
| InChi Key | HNICUWMFWZBIFP-IRQZEAMPSA-N |
| InChi Code | InChI=1S/C18H32O3/c1-2-3-11-14-17(19)15-12-9-7-5-4-6-8-10-13-16-18(20)21/h7,9,12,15,17,19H,2-6,8,10-11,13-14,16H2,1H3,(H,20,21)/b9-7-,15-12+/t17-/m0/s1 |
| Chemical Name | (9Z,11E,13S)-13-hydroxyoctadeca-9,11-dienoic acid |
| Synonyms | 13S-Hydroxy-9Z,11E-octadecadienoic acid; 13(S)HODE |
| 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 |
(S)-Coriolic acid (25μM) damages bronchial epithelium and modifies the structure of mitochondria[2]. (S)-Coriolic acid (30 nM; 6 hours; keratinocytes with or without E-FABP) activates NF-κB to cause K1 expression. Inducing IκB degradation and activating NF-κB, (S)-Coriolic acid raises the phosphorylation of IκBαat serine 32. The phosphorylation of Ikkinase-bat tyrosine 199 is also increased by (S)-Coriolic acid, and this subsequently promotes the phosphorylation of IκBα and NF-kB activation[3]. |
| ln Vivo | (S)-Coriolic acid (0-0.6 mg per mouse; Intranasally once a day for 3 consecutive days) causes epithelial damage, mitochondrial dysfunction, severe airway dysfunction, and airway neutrophilia[2]. |
| Animal Protocol |
BALB/c mice (6-8 weeks)[2] 0-0.6 mg per mouse Intranasally once a day for 3 consecutive days |
| ADME/Pharmacokinetics |
Metabolism / Metabolites 13-hydroxyoctadecadienoic acid has known human metabolites that include (2S,3S,4S,5R)-3,4,5-trihydroxy-6-[(9Z,11E,13S)-13-hydroxyoctadeca-9,11-dienoyl]oxyoxane-2-carboxylic acid and (2S,3S,4S,5R)-6-[(6S,7E,9Z)-17-carboxyheptadeca-7,9-dien-6-yl]oxy-3,4,5-trihydroxyoxane-2-carboxylic acid. |
| References |
[1]. Linoleic acid metabolite drives severe asthma by causing airway epithelial injury. Sci Rep. 2013;3:1349. [2]. Epidermal FABP (FABP5) regulates keratinocyte differentiation by 13(S)-HODE-mediated activation of the NF-κB signaling pathway. J Invest Dermatol. 2011;131(3):604-612. [3]. 15-Lipoxygenases and its metabolites 15(S)-HETE and 13(S)-HODE in the development of non-small cell lung cancer. Thorax. 2010;65(4):321-326. |
| Additional Infomation |
13(S)-HODE is an HODE (hydroxyoctadecadienoic acid) in which the double bonds are at positions 9 and 11 (E and Z geometry, respectively) and the hydroxy group is at position 13 (with S-configuration). It has a role as a mouse metabolite, a human xenobiotic metabolite and an antineoplastic agent. It is a conjugate acid of a 13(S)-HODE(1-). (9Z,11E,13S)-13-hydroxyoctadeca-9,11-dienoic acid has been reported in Lithothamnion corallioides, Pleurotus pulmonarius, and other organisms with data available. 13-Hydroxyoctadecadienoic Acid is a monohydroxy fatty acid resulting from the oxidation of linoleic acid or 13-hydroperoxy-9,11-octadecadienoic acid (13-HpODE). 13-HODE may mediate physiological and pathological responses and is a potential biomarker of various human diseases, and could contribute to the progression of certain diseases. |
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 | 3.3734 mL | 16.8668 mL | 33.7336 mL | |
| 5 mM | 0.6747 mL | 3.3734 mL | 6.7467 mL | |
| 10 mM | 0.3373 mL | 1.6867 mL | 3.3734 mL |