![2-[(1E)-2-(3,5-Dihydroxyphenyl)ethenyl]-1,3-benzenediol structure, CAS 86361-55-9](/structures/210000/188138_1_86361_55_9.png)
CAS Number86361-55-9
Synonyms2-[(E)-2-(3,5-Dihydroxyphenyl)vinyl]-1,3-benzenediol; Thieno[3,4-b]-1,4,7-trioxonin,2,3,5,6-tetrahydro; 2,3',5',6-tetrahydroxy-trans-stilbene; 2,3,5,6-tetrahydrothieno[3,4-b][1,4,7]trioxonin
Molecular FormulaC14H12O4
Molecular Weight244.25
Density1.5±0.1 g/cm3
Boiling Point540.8±30.0 °C at 760 mmHg
Melting Point87 - 90ºC
AppearanceSolid;White to Light yellow to Light orange powder to crystal
| Chemical & Physical Properties | |
|---|---|
| CAS Number | 86361-55-9 |
| Catalog No. | 2A-3186808 |
| Chinese Name | 买麻藤醇 |
| Synonyms | 2-[(E)-2-(3,5-Dihydroxyphenyl)vinyl]-1,3-benzenediol; Thieno[3,4-b]-1,4,7-trioxonin,2,3,5,6-tetrahydro; 2,3',5',6-tetrahydroxy-trans-stilbene; 2,3,5,6-tetrahydrothieno[3,4-b][1,4,7]trioxonin |
| Molecular Formula | C14H12O4 |
| Molecular Weight | 244.25 |
| Density | 1.5±0.1 g/cm3 |
| Boiling Point | 540.8±30.0 °C at 760 mmHg |
| Melting Point | 87 - 90ºC |
| Appearance | Solid;White to Light yellow to Light orange powder to crystal |
| Storage Condition | Store under inert gas; avoid air |
| Application | Gnetol is a phenolic compound isolated from the roots of Gnetum ula Brongn. Gnetol potently inhibits COX-1 (IC50 of 0.78 μM) and HDAC. Gnetol is a potent tyrosinase inhibitor with an IC50 of 4.5 μM fo |
| HTC | 2907299090 |
| PubChem ID | 93375065 |
| MDL Number | MFCD12405548 |
| SMILES | Oc1cc(O)cc(C=Cc2c(O)cccc2O)c1 |
| InChI | 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+ |
| InChI Key | DQULNTWGBBNZSC-SNAWJCMRSA-N |
| Bioactivity | Gnetol is a phenolic compound isolated from the root of Gnetum ula Brongn. Gnetol potently inhibits COX-1 (IC50 of 0.78 μM) and HDAC. Gnetol is a potent tyrosinase inhibitor with an IC50 of 4.5 μM for murine tyrosinase and suppresses melanin biosynthesis. Gnetol has antioxidant, antiproliferative, anticancer and hepatoprotective activity. Gnetol also possesses concentration-dependent α-Amylase, α-glucosidase, and adipogenesis activities[1][2][3]. Related Catalog Research Areas >> Cancer Signaling Pathways >> Immunology/Inflammation >> COX Signaling Pathways >> Metabolic Enzyme/Protease >> Tyrosinase Research Areas >> Metabolic Disease Signaling Pathways >> Cell Cycle/DNA Damage >> HDAC Signaling Pathways >> Epigenetics >> HDAC Target COX-1:0.78 μM (IC50) Tyrosinase:4.5 μM (IC50) HDAC In Vitro The antiproliferative activities of Gnetol are tested in HCT-116, Hep-G2, MDA-MB-231, and PC-3 cell lines by measuring cell viability after treatment with 4.1 μM, 40.9 μM, 204.7 μM, 409.4 μM, and 1023.6 μM. Gnetol shows concentration-dependent reductions in cell viability in cancer cell lines with greatest activity in colorectal cancer[1]. Gnetol at 200 µg/mL significantly offers the highest protection of 54.3% against the toxicant. A lower dose of Gnetol (50 µg/mL) also shields the cell line from the toxic effects of CCl4[3]. The ligand molecule TGF-β and PPARα protein show that Gnetol has the binding affinity of 7.0 and 8.4, respectively[3]. In Vivo Male Sprague-Dawley rats were cannulated and dosed either intravenously with Gnetol (10 μg/kg) or orally (100 mg/kg). After oral and intravenous administration, Gnetol is detected in both serum and urine as the parent compound and as a glucuronidated metabolite. The bioavailability of Gnetol is determined to be 6%. Gnetol is rapidly glucuronidated and is excreted in urine and via nonrenal routes[1]. Pretreatment of Male NIH Swiss mice (20-35 g) with Gnetol (50mg/kg, SC) is able to increase the latency period to response in analgesia models[1]. References [1]. Remsberg CM, et al. Preclinical Pharmacokinetics and Pharmacodynamics and Content Analysis of Gnetol in Foodstuffs. Phytother Res. 2015 Aug;29(8):1168-79. [2]. Ohguchi K, et al. Gnetol as a potent tyrosinase inhibitor from genus Gnetum. Biosci Biotechnol Biochem. 2003 Mar;67(3):663-5. [3]. Jinadatta P, et al. In silico, in vitro: antioxidant and antihepatotoxic activity of gnetol from Gnetum ula Brongn. Bioimpacts. 2019;9(4):239-249. Chemical & Physical Properties Density 1.5±0.1 g/cm3 Boiling Point 540.8±30.0 °C at 760 mmHg Melting Point 87 - 90ºC Molecular Formula C14H12O4 Molecular Weight 244.243 Flash Point 269.7±19.2 °C Exact Mass 244.073563 PSA 80.92000 LogP 3.73 Vapour Pressure 0.0±1.5 mmHg at 25°C Index of Refraction 1.801 InChIKey DQULNTWGBBNZSC-SNAWJCMRSA-N SMILES Oc1cc(O)cc(C=Cc2c(O)cccc2O)c1 |
| Use of | Gnetol is a phenolic compound isolated from the root of Gnetum ula Brongn. Gnetol potently inhibits COX-1 (IC50 of 0.78 μM) and HDAC. Gnetol is a potent tyrosinase inhibitor with an IC50 of 4.5 μM for murine tyrosinase and suppresses melanin biosynthesis. Gnetol has antioxidant, antiproliferative, anticancer and hepatoprotective activity. Gnetol also possesses concentration-dependent α-Amylase, α-glucosidase, and adipogenesis activities[1][2][3]. Properties Name 2-[(1E)-2-(3,5-Dihydroxyphenyl)ethenyl]-1,3-benzenediol Synonym More Synonyms Gnetol Biological Activity Description Gnetol is a phenolic compound isolated from the root of Gnetum ula Brongn. Gnetol potently inhibits COX-1 (IC50 of 0.78 μM) and HDAC. Gnetol is a potent tyrosinase inhibitor with an IC50 of 4.5 μM for murine tyrosinase and suppresses melanin biosynthesis. Gnetol has antioxidant, antiproliferative, anticancer and hepatoprotective activity. Gnetol also possesses concentration-dependent α-Amylase, α-glucosidase, and adipogenesis activities[1][2][3]. Related Catalog Research Areas >> Cancer Signaling Pathways >> Immunology/Inflammation >> COX Signaling Pathways >> Metabolic Enzyme/Protease >> Tyrosinase Research Areas >> Metabolic Disease Signaling Pathways >> Cell Cycle/DNA Damage >> HDAC Signaling Pathways >> Epigenetics >> HDAC COX-1:0.78 μM (IC50) Tyrosinase:4.5 μM (IC50) References [1]. Remsberg CM, et al. Preclinical Pharmacokinetics and Pharmacodynamics and Content Analysis of Gnetol in Foodstuffs. Phytother Res. 2015 Aug;29(8):1168-79. [2]. Ohguchi K, et al. Gnetol as a potent tyrosinase inhibitor from genus Gnetum. Biosci Biotechnol Biochem. 2003 Mar;67(3):663-5. [3]. Jinadatta P, et al. In silico, in vitro: antioxidant and antihepatotoxic activity of gnetol from Gnetum ula Brongn. Bioimpacts. 2019;9(4):239-249. Chemical & Physical Properties Molecular Formula C14H12O4 Exact Mass 244.073563 PSA 80.92000 Index of Refraction 1.801 InChIKey DQULNTWGBBNZSC-SNAWJCMRSA-N |
| Tax Rebate | 9.0% |
| Supervision | A. Customs clearance form for inbound goods B. Customs clearance form for outbound goods |
| Inspection | R. Imported food hygiene supervision and inspection S. Export food hygiene supervision and inspection M. Imported commodity inspection N. Exported commodity inspection |
| Transport Info | Product name: Purity: 98.0% |
| MSDS Transport Info | Module 14. Shipping information United Nations classification: inconsistent with United Nations classification standards UN number: not specified |
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