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C8 Ceramide

Alias: N-Octanoyl-D-erythro-Sphingosine; C8-Ceramide; C8 Ceramide
Cat No.:V15936 Purity: ≥98%
C8-Ceramide (N-Octanoyl-D-erythro-sphingosine) is a cell-penetrating/penetrable endogenous ceramide analog.
C8 Ceramide
C8 Ceramide Chemical Structure CAS No.: 74713-59-0
Product category: New1
This product is for research use only, not for human use. We do not sell to patients.
Size Price Stock Qty
5mg
10mg
50mg
Other Sizes
Official Supplier of:
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Product Description
C8-Ceramide (N-Octanoyl-D-erythro-sphingosine) is a cell-penetrating/penetrable endogenous ceramide analog. C8-Ceramide has anti-proliferation properties and can be used as a chemotherapeutic agent. C8-Ceramide can stimulate dendritic cells to promote T cell response to viral infection. C8-Ceramide slightly induces PKC activation in vitro.
Biological Activity I Assay Protocols (From Reference)
ln Vitro
Tumor cell growth is irreversibly reduced and morphological alterations are induced by C8-ceramide (3 μM; 48 hours) [1]. In human cervical carcinoma cells, C8-ceramide can cause necrosis-like cell death, but it does not cause the molecular marker of apoptosis, PARP, to be cleaved in a caspase-dependent manner [1]. In NSCLC H1299 cells, C8-ceramide may elevate endogenous ROS levels (10-30 µM; 24 hours), inhibit proliferation (10-50 µM; 24 hours), and therefore induce apoptosis (10-50 µM; 48 hours) [2].
ln Vivo
In mice infected with a virus, C8-ceramide (0.1 mg/kg; administered intravenously) increases CD8+ and CD4+ T cell responses to infection [3].
Cell Assay
Cell viability assay [1]
Cell Types: CALO cells, INBL cells, HeLa cells
Tested Concentrations: 3 μM
Incubation Duration: 48 hrs (hours)
Experimental Results: The number of tumor cells was Dramatically diminished.

Cell proliferation assay[2]
Cell Types: H1299 Cell
Tested Concentrations: 10 µM, 20 µM, 30 µM, 40 µM, 50 µM
Incubation Duration: 24 hrs (hours)
Experimental Results: diminished cell proliferation rate in a dose-dependent manner, IC50 22.9 µM.

Cell cycle analysis[2]
Cell Types: H1299 Cell
Tested Concentrations: 10 µM, 20 µM, 30 µM, 40 µM, 50 µM
Incubation Duration: 24 hrs (hours)
Experimental Results: Causes G1 arrest.

Apoptosis analysis[2]
Cell Types: H1299 Cell
Tested Concentrations: 10 µM, 20 µM, 30 µM
Incubation Duration: 24 hrs (hours), 48 hrs (hours)
Experimental Results: Increased levels of cleaved caspase-3.
Animal Protocol
Animal/Disease Models: C57BL/6 mice, lymphocytic choriomeningitis virus infection [3]
Doses: 0.1 mg/kg
Route of Administration: Intranasal administration
Experimental Results: Enhanced lung CD8+ T cell response to influenza.
References

[1]. Ceramide promotes the death of human cervical tumor cells in the absence of biochemical and morphological markers of apoptosis. Biochem Biophys Res Commun. 2002 May 10;293(3):1028-36.

[2]. Exogenous C8-Ceramide Induces Apoptosis by Overproduction of ROS and the Switch of Superoxide Dismutases SOD1 to SOD2 in Human Lung Cancer Cells. Int J Mol Sci. 2018 Oct; 19(10): 3010.

[3]. A ceramide analogue stimulates dendritic cells to promote T cell responses upon virus infections. J Immunol. 2015 May 1; 194(9): 4339-4349.

[4]. Ceramides modulate protein kinase C activity and perturb the structure of Phosphatidylcholine/Phosphatidylserine bilayers. Biophys J. 1999 Sep; 77(3): 1489-1497.

[5]. Ceramide contributes to pathogenesis and may be targeted for therapy in VCP inclusion body myopathy. Hum Mol Genet. 2021 Jan 7;ddaa248.

Additional Infomation
N-octanoylsphingosine is an N-acylsphingosine in which the ceramide N-acyl group is specified as octanoyl. It is functionally related to an octanoic acid.
These protocols are for reference only. InvivoChem does not independently validate these methods.
Physicochemical Properties
Molecular Formula
C26H51NO3
Molecular Weight
425.69
Exact Mass
425.386
CAS #
74713-59-0
PubChem CID
5702614
Appearance
White to off-white solid powder
Density
0.9±0.1 g/cm3
Boiling Point
595.5±50.0 °C at 760 mmHg
Melting Point
68-70°C
Flash Point
313.9±30.1 °C
Vapour Pressure
0.0±3.8 mmHg at 25°C
Index of Refraction
1.482
LogP
9.09
Hydrogen Bond Donor Count
3
Hydrogen Bond Acceptor Count
3
Rotatable Bond Count
22
Heavy Atom Count
30
Complexity
398
Defined Atom Stereocenter Count
2
SMILES
CCCCCCCCCCCCC/C=C/[C@H]([C@H](CO)NC(=O)CCCCCCC)O
InChi Key
APDLCSPGWPLYEQ-WRBRXSDHSA-N
InChi Code
InChI=1S/C26H51NO3/c1-3-5-7-9-10-11-12-13-14-15-16-18-19-21-25(29)24(23-28)27-26(30)22-20-17-8-6-4-2/h19,21,24-25,28-29H,3-18,20,22-23H2,1-2H3,(H,27,30)/b21-19+/t24-,25+/m0/s1
Chemical Name
N-[(E,2S,3R)-1,3-dihydroxyoctadec-4-en-2-yl]octanamide
Synonyms
N-Octanoyl-D-erythro-Sphingosine; C8-Ceramide; C8 Ceramide
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

Note: Please store this product in a sealed and protected environment (e.g. under nitrogen), avoid exposure to moisture.
Shipping Condition
Room temperature (This product is stable at ambient temperature for a few days during ordinary shipping and time spent in Customs)
Solubility Data
Solubility (In Vitro)
DMSO : ≥ 100 mg/mL (~234.91 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 : PEG300Tween 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).
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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 : PEG300Tween 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).
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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 2.3491 mL 11.7456 mL 23.4913 mL
5 mM 0.4698 mL 2.3491 mL 4.6983 mL
10 mM 0.2349 mL 1.1746 mL 2.3491 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.

Calculator

Molarity Calculator allows you to calculate the mass, volume, and/or concentration required for a solution, as detailed below:

  • Calculate the Mass of a compound required to prepare a solution of known volume and concentration
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An example of molarity calculation using the molarity calculator is shown below:
What is the mass of compound required to make a 10 mM stock solution in 5 ml of DMSO given that the molecular weight of the compound is 350.26 g/mol?
  • Enter 350.26 in the Molecular Weight (MW) box
  • Enter 10 in the Concentration box and choose the correct unit (mM)
  • Enter 5 in the Volume box and choose the correct unit (mL)
  • Click the “Calculate” button
  • The answer of 17.513 mg appears in the Mass box. In a similar way, you may calculate the volume and concentration.

Dilution Calculator allows you to calculate how to dilute a stock solution of known concentrations. For example, you may Enter C1, C2 & V2 to calculate V1, as detailed below:

What volume of a given 10 mM stock solution is required to make 25 ml of a 25 μM solution?
Using the equation C1V1 = C2V2, where C1=10 mM, C2=25 μM, V2=25 ml and V1 is the unknown:
  • Enter 10 into the Concentration (Start) box and choose the correct unit (mM)
  • Enter 25 into the Concentration (End) box and select the correct unit (mM)
  • Enter 25 into the Volume (End) box and choose the correct unit (mL)
  • Click the “Calculate” button
  • The answer of 62.5 μL (0.1 ml) appears in the Volume (Start) box
g/mol

Molecular Weight Calculator allows you to calculate the molar mass and elemental composition of a compound, as detailed below:

Note: Chemical formula is case sensitive: C12H18N3O4  c12h18n3o4
Instructions to calculate molar mass (molecular weight) of a chemical compound:
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Definitions of molecular mass, molecular weight, molar mass and molar weight:
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  • Molar mass (molar weight) is the mass of one mole of a substance and is expressed in g/mol.
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Reconstitution Calculator allows you to calculate the volume of solvent required to reconstitute your vial.

  • Enter the mass of the reagent and the desired reconstitution concentration as well as the correct units
  • Click the “Calculate” button
  • The answer appears in the Volume (to add to vial) box
In vivo Formulation Calculator (Clear solution)
Step 1: Enter information below (Recommended: An additional animal to make allowance for loss during the experiment)
Step 2: Enter in vivo formulation (This is only a calculator, not the exact formulation for a specific product. Please contact us first if there is no in vivo formulation in the solubility section.)
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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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