Stearidonic acid (6Z,9Z,12Z,15Z-Octadecatetraenoic acid) is an intermediate fatty acid in the biosynthetic pathway from α-linolenic acid to VLC ω-3 PUFA. Stearidonic acid is more efficiently converted than α-linolenic acid, and increasing the intake of stearidonic acid can increase the content of erythrocyte eicosapentaenoic acid (EPA). Stearidonic acid can also be isolated from the methanol extract of the brown alga Cladosporium.

Physicochemical Properties

Molecular Formula	C18H28O2
Molecular Weight	276.41
Exact Mass	276.208
CAS #	20290-75-9
PubChem CID	5312508
Appearance	Colorless to light yellow liquid
Density	0.9±0.1 g/cm3
Boiling Point	412.8±24.0 °C at 760 mmHg
Flash Point	309.6±18.0 °C
Vapour Pressure	0.0±2.1 mmHg at 25°C
Index of Refraction	1.504
LogP	6.09
Hydrogen Bond Donor Count	1
Hydrogen Bond Acceptor Count	2
Rotatable Bond Count	12
Heavy Atom Count	20
Complexity	335
Defined Atom Stereocenter Count	0
SMILES	CC/C=C\C/C=C\C/C=C\C/C=C\CCCCC(=O)O
InChi Key	JIWBIWFOSCKQMA-LTKCOYKYSA-N
InChi Code	InChI=1S/C18H28O2/c1-2-3-4-5-6-7-8-9-10-11-12-13-14-15-16-17-18(19)20/h3-4,6-7,9-10,12-13H,2,5,8,11,14-17H2,1H3,(H,19,20)/b4-3-,7-6-,10-9-,13-12-
Chemical Name	(6Z,9Z,12Z,15Z)-octadeca-6,9,12,15-tetraenoic 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

References

[1].Stearidonic acid as a supplemental source of ω-3 polyunsaturated fatty acids to enhance status for improved human health. Nutrition. 2013 Feb;29(2):363-9. [2].An allelopathic fatty acid from the brown alga Cladosiphon okamuranus[J]. Phytochemistry, 1988, 27(3): 731-735.

Additional Infomation

All-cis-octadeca-6,9,12,15-tetraenoic acid is an octadecatetraenoic acid having four double bonds located at positions 6, 9, 12 and 15 (the all-cis-isomer). It has been isolated from Lithospermum officinale and fish oils. It has a role as a plant metabolite, a Daphnia galeata metabolite and a mouse metabolite. It is an omega-3 fatty acid, a long-chain fatty acid and an octadecatetraenoic acid. It is a conjugate acid of a (6Z,9Z,12Z,15Z)-octadecatetraenoate. Stearidonic acid has been reported in Cladosiphon okamuranus, Mucor javanicus, and other organisms with data available. Parinaric Acid is a polyunsaturated long-chain fatty acid with an 18-carbon backbone and 4 double bonds originating from the 3rd, 5th, 7th and 9th positions from the methyl end.

Solubility Data

Solubility (In Vitro)

Typically soluble in DMSO (e.g. 10 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.)

Preparing Stock Solutions		1 mg	5 mg	10 mg
	1 mM	3.6178 mL	18.0891 mL	36.1781 mL
	5 mM	0.7236 mL	3.6178 mL	7.2356 mL
	10 mM	0.3618 mL	1.8089 mL	3.6178 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.