Gnetol is a phenolic compound extracted from the roots of Gnetum montanum. Gnetol potently inhibits COX-1 (IC50 of 0.78 μM) and HDAC. Gnetol is a potent tyrosinase inhibitor (antagonist) with IC50 of 4.5 μM for mouse tyrosinase and can inhibit melanin biosynthesis. Gnetol has antioxidant, antiproliferation, anticancer and hepatoprotective activities. Gnetol also has concentration-dependent alpha-amylase, alpha-glucosidase, and adipogenic activities.

Physicochemical Properties

Molecular Formula	C14H12O4
Molecular Weight	244.2427
Exact Mass	244.073
CAS #	86361-55-9
PubChem CID	45382232
Appearance	White to off-white solid powder
Density	1.5±0.1 g/cm3
Boiling Point	540.8±30.0 °C at 760 mmHg
Melting Point	87 - 90ºC
Flash Point	269.7±19.2 °C
Vapour Pressure	0.0±1.5 mmHg at 25°C
Index of Refraction	1.801
LogP	3.73
Hydrogen Bond Donor Count	4
Hydrogen Bond Acceptor Count	4
Rotatable Bond Count	2
Heavy Atom Count	18
Complexity	272
Defined Atom Stereocenter Count	0
SMILES	C1=CC(=C(C(=C1)O)/C=C/C2=CC(=CC(=C2)O)O)O
InChi Key	DQULNTWGBBNZSC-SNAWJCMRSA-N
InChi Code	InChI=1S/C14H12O4/c15-10-6-9(7-11(16)8-10)4-5-12-13(17)2-1-3-14(12)18/h1-8,15-18H/b5-4+
Chemical Name	2-[(E)-2-(3,5-dihydroxyphenyl)ethenyl]benzene-1,3-diol
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: This product requires protection from light (avoid light exposure) during transportation and storage.
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	Cell viability was measured in HCT-116, Hep-G2, MDA-MB-231, and PC-3 cell lines following treatment with 4.1 μM, 40.9 μM, 204.7 μM, 409.4 μM, and 1023.6 μM in order to assess the antiproliferative effect of gnetol. ....In the most aggressive cancer cell lines in colorectal cancer, genetol shows a concentration-dependent decrease in cell viability [1]. At 200 µg/mL, gnetol notably offered the maximum level of toxin protection, at 54.3%. Gnetol at lower concentrations (50 µg/mL) also shields cell lines from CCl4's harmful effects [3]. Gnetol's binding affinities are 7.0 and 8.4, respectively, as demonstrated by the ligand molecules TGF-β and PPARα protein [3].
ln Vivo	After intubating male Sprague-Dawley rats, Gnetol was given either intravenously (10 μg/kg) or orally (100 mg/kg). Gnetol has been found in serum and urine as the parent compound and glucuronidated metabolite after oral and intravenous administration. It has been found that gnetol has a bioavailability of 6%. Cannabidiol is rapidly glucuronidated and excreted via urinary and non-renal routes [1]. Pretreatment of male NIH Swiss mice (20-35 g) with Gnetol (50 mg/kg, SC) prolongs the latency of response in an analgesic model [1].
References	[1]. Preclinical Pharmacokinetics and Pharmacodynamics and Content Analysis of Gnetol in Foodstuffs. Phytother Res. 2015 Aug;29(8):1168-79. [2]. Gnetol as a potent tyrosinase inhibitor from genus Gnetum. Biosci Biotechnol Biochem. 2003 Mar;67(3):663-5. [3]. In silico, in vitro: antioxidant and antihepatotoxic activity of gnetol from Gnetum ula Brongn. Bioimpacts. 2019;9(4):239-249.
Additional Infomation	Gnetol has been reported in Gnetum montanum, Gnetum parvifolium, and other organisms with data available.

Solubility Data

Solubility (In Vitro)

DMSO : ~100 mg/mL (~409.43 mM)

Solubility (In Vivo)

Solubility in Formulation 1: ≥ 2.5 mg/mL (10.24 mM) (saturation unknown) in 10% DMSO + 40% PEG300 + 5% Tween80 + 45% Saline (add these co-solvents sequentially from left to right, and one by one), clear solution. For example, if 1 mL of working solution is to be prepared, you can add 100 μL of 25.0 mg/mL clear DMSO stock solution to 400 μL PEG300 and mix evenly; then add 50 μL Tween-80 to the above solution and mix evenly; then add 450 μL normal saline to adjust the volume to 1 mL. Preparation of saline: Dissolve 0.9 g of sodium chloride in 100 mL ddH₂ O to obtain a clear solution. Solubility in Formulation 2: ≥ 2.5 mg/mL (10.24 mM) (saturation unknown) in 10% DMSO + 90% (20% SBE-β-CD in Saline) (add these co-solvents sequentially from left to right, and one by one), clear solution. For example, if 1 mL of working solution is to be prepared, you can add 100 μL of 25.0 mg/mL clear DMSO stock solution to 900 μL of 20% SBE-β-CD physiological saline solution and mix evenly. 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. Solubility in Formulation 3: ≥ 2.5 mg/mL (10.24 mM) (saturation unknown) in 10% DMSO + 90% Corn Oil (add these co-solvents sequentially from left to right, and one by one), clear solution. For example, if 1 mL of working solution is to be prepared, you can add 100 μL of 25.0 mg/mL clear DMSO stock solution to 900 μL of corn oil and mix evenly.  (Please use freshly prepared in vivo formulations for optimal results.)

Preparing Stock Solutions		1 mg	5 mg	10 mg
	1 mM	4.0943 mL	20.4717 mL	40.9433 mL
	5 mM	0.8189 mL	4.0943 mL	8.1887 mL
	10 mM	0.4094 mL	2.0472 mL	4.0943 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.