CAS Number76-66-4
SynonymsMethyl-(7β,16E,20α)-16-(methoxymethyliden)-2-oxocorynoxan-17-oat; Methyl (7β,16E,20α)-16-(methoxymethylene)-2-oxocorynoxan-17-oate; Methyl (16E)-16-(methoxymethylene)-2-oxocorynoxan-17-oate; Mitrinermine; Rhyncophylline; mitrinermin; Methyl (7β,16E,20α)-2-hydroxy-17-methoxy-1,2-didehydrocorynox-16-en-16-carboxylate; methyl (7β,16E,20α)-16-(methoxymethylidene)-2-oxocorynoxan-17-oate; rhynchophyllin; RHYNCHOLPHYLLINE
Molecular FormulaC22H28N2O4
Molecular Weight384.48
Purity98.00%
Density1.2±0.1 g/cm3
Boiling Point560.8±50.0 °C at 760 mmHg
Melting Point216°; mp 197-199° (Ban et al., loc. cit.)
| Chemical & Physical Properties | |
|---|---|
| CAS Number | 76-66-4 |
| Catalog No. | 2A-9017148 |
| Chinese Name | 钩藤碱 |
| Synonyms | Methyl-(7β,16E,20α)-16-(methoxymethyliden)-2-oxocorynoxan-17-oat; Methyl (7β,16E,20α)-16-(methoxymethylene)-2-oxocorynoxan-17-oate; Methyl (16E)-16-(methoxymethylene)-2-oxocorynoxan-17-oate; Mitrinermine; Rhyncophylline; mitrinermin; Methyl (7β,16E,20α)-2-hydroxy-17-methoxy-1,2-didehydrocorynox-16-en-16-carboxylate; methyl (7β,16E,20α)-16-(methoxymethylidene)-2-oxocorynoxan-17-oate; rhynchophyllin; RHYNCHOLPHYLLINE |
| Molecular Formula | C22H28N2O4 |
| Molecular Weight | 384.48 |
| Purity | 98.00 |
| Density | 1.2±0.1 g/cm3 |
| Boiling Point | 560.8±50.0 °C at 760 mmHg |
| Melting Point | 216°; mp 197-199° (Ban et al., loc. cit.) |
| Storage Condition | Keep sealed. |
| Application | Rhyncholphylline is an alkaloid compound isolated from Uncaria rhynchophyllum. It has high biological activity and is widely used in anti-inflammatory, neuroprotective and other research. |
| HTC | 29399990 |
| MDL Number | C22H28N2O4 |
| SMILES | CCC1CN2CCC3(C(=O)Nc4ccccc43)C2CC1C(=COC)C(=O)OC |
| InChI | InChI=1S/C22H28N2O4/c1-4-14-12-24-10-9-22(17-7-5-6-8-18(17)23-21(22)26)19(24)11-15(14)16(13-27-2)20(25)28-3/h5-8,13-15,19H,4,9-12H2,1-3H3,(H,23,26)/b16-13+/t14-,15-,19-,22+/m0/s1 |
| InChI Key | DAXYUDFNWXHGBE-UHFFFAOYSA-N |
| MSDS | msds/17148_1_76_66_4.pdf |
| Bioactivity | Rhyncholphylline, an alkaloid isolated from Uncaria, shows potent inhibition of lipopolysaccharide (LPS)-induced NO production in rat primary microglial cells.IC50 value:Target:In vitro: Rhyncholphylline effectively suppresses release of proinflammatory cytokines in LPS-activated microglial cells and the underling molecular mechanism for the inhibition of microglial activation; Attenuated LPS-induced production of proinflammatory cytokines such as TNF-α and IL-1β as well as NO in mouse N9 microglial cells [1]. Rhynchophylline exerts it protective action against ischemia-induced neuronal damage by preventing NMDA, muscarinic M1, and 5-HT2 receptors-mediated neurotoxicity during ischemia [3].In vivo: The neuroprotective effect of rhynchophylline was investigated in a stroke model. Following pMCAO, rhynchophylline treatment not only ameliorated neurological deficits, infarct volume and brain edema, but also increased claudin-5 and BDNF expressions (p < 0.05). Moreover, rhynchophylline could activate PI3K/Akt/mTOR signaling while inhibiting TLRs/NF-κB pathway [2]. Related Catalog Signaling Pathways >> Others >> Others Natural Products >> Alkaloid Research Areas >> Others References [1]. Dan Yuan, et al. Anti-inflammatory effects of rhynchophylline and isorhynchophylline in mouse N9 microglial cells and the molecular mechanism. International Immunopharmacology Volume 9, Issues 13-14, December 2009, Pages 1549-1554 [2]. Houcai Huang, et al. Neuroprotective Effects of Rhynchophylline Against Ischemic Brain Injury via Regulation of the Akt/mTOR and TLRs Signaling Pathways. Molecules 2014, 19 (8): 11196-11210; doi:10.3390/molecules190811196 [3]. Tai-Hyun Kang, et al. Protective effect of rhynchophylline and isorhynchophylline on in vitro ischemia-induced neuronal damage in the hippocampus: putative neurotransmitter receptors involved in their action. Life Sciences Volume 76, Issue 3, 3 December [4]. Kinzo Matsumoto, et al. Suppressive effects of isorhynchophylline on 5-HT2A receptor function in the brain: Behavioural and electrophysiological studies. European Journal of Pharmacology Volume 517, Issue 3, 11 July 2005, Pages 191-199 Chemical & Physical Properties Density 1.2±0.1 g/cm3 Boiling Point 560.8±50.0 °C at 760 mmHg Melting Point 216°; mp 197-199° (Ban et al., loc. cit.) Molecular Formula C22H28N2O4 Molecular Weight 384.469 Flash Point 293.0±30.1 °C Exact Mass 384.204895 PSA 67.87000 LogP 3.31 Vapour Pressure 0.0±1.5 mmHg at 25°C Index of Refraction 1.596 InChIKey DAXYUDFNWXHGBE-UHFFFAOYSA-N SMILES CCC1CN2CCC3(C(=O)Nc4ccccc43)C2CC1C(=COC)C(=O)OC |
| Use of | Properties Name Rhynchophylline Synonym More Synonyms Rhynchophylline Biological Activity Related Catalog Signaling Pathways >> Others >> Others Natural Products >> Alkaloid Research Areas >> Others References [3]. Tai-Hyun Kang, et al. Protective effect of rhynchophylline and isorhynchophylline on in vitro ischemia-induced neuronal damage in the hippocampus: putative neurotransmitter receptors involved in their action. Life Sciences Volume 76, Issue 3, 3 December [4]. Kinzo Matsumoto, et al. Suppressive effects of isorhynchophylline on 5-HT2A receptor function in the brain: Behavioural and electrophysiological studies. European Journal of Pharmacology Volume 517, Issue 3, 11 July 2005, Pages 191-199 Chemical & Physical Properties Molecular Formula C22H28N2O4 Exact Mass 384.204895 PSA 67.87000 Index of Refraction 1.596 InChIKey DAXYUDFNWXHGBE-UHFFFAOYSA-N |
| 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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