Cannabisin F is a SIRT1 modulator. Cannabisin F, a hemp seed ligninamide, may be utilized in anti-inflammatory and antioxidant research. Cannabisin F, as a regulator of SIRT1/NF-κB and Nrf2, may be a potential modulator of neurodegenerative diseases.

Physicochemical Properties

Molecular Formula	C36H36N2O8
Molecular Weight	624.67964
Exact Mass	624.247
CAS #	163136-19-4
PubChem CID	71448967
Appearance	Typically exists as solid at room temperature
Density	1.3±0.1 g/cm3
Boiling Point	961.0±65.0 °C at 760 mmHg
Flash Point	535.0±34.3 °C
Vapour Pressure	0.0±0.3 mmHg at 25°C
Index of Refraction	1.659
LogP	4.68
Hydrogen Bond Donor Count	5
Hydrogen Bond Acceptor Count	8
Rotatable Bond Count	14
Heavy Atom Count	46
Complexity	989
Defined Atom Stereocenter Count	0
SMILES	COC1=C(C=CC(=C1)C=CC(=O)NCCC2=CC=C(C=C2)O)OC(=CC3=CC(=C(C=C3)O)OC)C(=O)NCCC4=CC=C(C=C4)O
InChi Key	JCUQMHMUDDMCSX-AADBSILNSA-N
InChi Code	InChI=1S/C36H36N2O8/c1-44-32-22-27(7-14-30(32)41)23-34(36(43)38-20-18-25-5-12-29(40)13-6-25)46-31-15-8-26(21-33(31)45-2)9-16-35(42)37-19-17-24-3-10-28(39)11-4-24/h3-16,21-23,39-41H,17-20H2,1-2H3,(H,37,42)(H,38,43)/b16-9+,34-23-
Chemical Name	(Z)-3-(4-hydroxy-3-methoxyphenyl)-N-[2-(4-hydroxyphenyl)ethyl]-2-[4-[(E)-3-[2-(4-hydroxyphenyl)ethylamino]-3-oxoprop-1-enyl]-2-methoxyphenoxy]prop-2-enamide
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

Targets	SIRT1[1]
ln Vitro	In BV2 microglia cells, Cannabisin F (0~15 μM; 1 hour) suppresses p65 phosphorylation but increases Nrf2 and HO-1 expression[1]. Cannabisin F (0~15 μM; 24 hours; BV2 microglia cells) suppresses the formation of ROS, enhances the expression of SIRT1, and has no discernible effect on cell survival[1]. It also decreases the synthesis of IL-6 and TNF-α and their mRNA expression.
Cell Assay	Cell Viability Assay[1] Cell Types: BV2 microglia cells Tested Concentrations: 0~15 µM Incubation Duration: 24 hrs (hours) Experimental Results: Had no significant effect on cell survival. Western Blot Analysis[1] Cell Types: BV2 microglia cells Tested Concentrations: 0~15 µM Incubation Duration: 1 hour Experimental Results: Inhibited the phosphorylation of IκBα, p65, but enhanced the expression of Nrf2 and HO-1.
References	[1]. Cannabisin F from Hemp (Cannabis sativa) Seed Suppresses Lipopolysaccharide-Induced Inflammatory Responses in BV2 Microglia as SIRT1 Modulator. Int J Mol Sci. 2019;20(3):507. Published 2019 Jan 25.
Additional Infomation	Cannabisin F has been reported in Mitrephora thorelii, Mitrephora tomentosa, and Cannabis sativa with data available.

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	1.6008 mL	8.0041 mL	16.0082 mL
	5 mM	0.3202 mL	1.6008 mL	3.2016 mL
	10 mM	0.1601 mL	0.8004 mL	1.6008 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.