Rhynchophylline

Iupac Name：methyl (Z)-2-(6'-ethyl-2-oxospiro[1H-indole-3,1'-3,5,6,7,8,8a-hexahydro-2H-indolizine]-7'-yl)-3-methoxyprop-2-enoate

CAS No.: 76-66-4

Molecular Weight：384.476

Modify Date.: 2023-02-13 10:32

Introduction:

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 N

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1. Names and Identifiers

1.1 Name: Rhynchophylline
1.2 Synonyms: 16e,20-alpha)-(7-bet Hook vine extract Methyl (16E)-16-(methoxymethylene)-2-oxocorynoxan-17-oate Methyl (2E)-2-[(3R,6'R,7'S,8a'S)-6'-ethyl-2-oxo-1,2,2',3',6',7',8',8a'-octahydro-5'H-spiro[indole-3,1'-indolizin]-7'-yl]-3-methoxyacrylate Methyl (7Β,16E,20α)-16-(methoxymethylene)-2-oxocorynoxan-17-oate methyl (7Β,16E,20α)-16-(methoxymethylidene)-2-oxocorynoxan-17-oate Methyl (7Β,16E,20α)-2-hydroxy-17-methoxy-1,2-didehydrocorynox-16-en-16-carboxylate Methyl (7β,20α)-16-(methoxymethylene)-2-oxocorynoxan-17-oate Methyl 2-[(3R,6'R,7'S,8'aS)-6'-ethyl-2-oxospiro[1H-indole-3,1'-3,5,6,7,8,8a-hexahydro-2H-indolizine]-7'-yl]-3-methoxyprop-2-enoate Methyl-(7Β,16E,20α)-16-(methoxymethyliden)-2-oxocorynoxan-17-oat mitrinermin MITRINERMINE RHYNCHOLPHYLLINE rhynchophyllin Rhynchophylline 76-66-4 Rhyncophylline Spiro[3H-indole-3,1'(5'H)-indolizine]-7'-acetic acid, 6'-ethyl-1,2,2',3',6',7',8',8'a-octahydro-α-(methoxymethylene)-2-oxo-, methyl ester, (3R,6'R,7'S,8'aS)- Spiro[3H-indole-3,1'(5'H)-indolizine]-7'-acetic acid, 6'-ethyl-1,2,2',3',6',7',8',8'a-octahydro-α-(methoxymethylene)-2-oxo-, methyl ester, (αE,3R,6'R,7'S,8'aS)- Spiro[3H-indole-3,1'(5'H)-indolizine]-7'-acetic acid, 6'-ethyl-1,2,2',3',6',7',8',8'a-octahydro-α-(methoxymethylene)-2-oxo-, methyl ester, (αE,3S,6'S,7'S,8'aS)- Spiro[3H-indole-3,1'(5'H)-indolizine]-7'-acetic acid, 6'-ethyl-2',3',6',7',8',8'a-hexahydro-2-hydroxy-α-(methoxymethylene)-, methyl ester, (αE,3R,6'R,7'S,8'aS)-

1.3 CAS No.: 76-66-4

1.4 CID: 5281408

1.5 Molecular Formula: C22H28N2O4 (isomer)

1.6 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

1.7 InChkey: DAXYUDFNWXHGBE-KAXDATADSA-N

1.8 Canonical Smiles: CCC1CN2CCC3(C2CC1C(=COC)C(=O)OC)C4=CC=CC=C4NC3=O

1.9 Isomers Smiles: CC[C@H]1CN2CC[C@]3([C@@H]2C[C@@H]1/C(=C\OC)/C(=O)OC)C4=CC=CC=C4NC3=O

2. Properties

2.1 Density: 1.23

2.1 Melting point: 216°; mp 197-199° (Ban et al., loc. cit.)

2.1 Boiling point: 560.8 °C at 760 mmHg

2.1 Refractive index: 1.596

2.1 Flash Point: 293 °C

2.1 Precise Quality: 384.204895

2.1 PSA: 67.87000

2.1 logP: 2.77610

2.1 Λmax: 247nm(lit.)

2.2 Appearance: Red brown or white fine powder

2.3 Color/Form: Powder

2.4 pKa: 6.4(at 25℃)

2.5 StorageTemp: Sealed in dry,Store in freezer, under -20°C

3. Use and Manufacturing

3.1 Definition: ChEBI: A natural product found in Uncaria macrophylla. RhynchophyllineSupplier

4. Safety and Handling

4.1 Risk Statements: S24/25

4.1 Safety Statements: S24/25

4.1 RTECS: GN1600000

5. MSDS

2.Hazard identification

2.1 Classification of the substance or mixture

Acute toxicity - Oral, Category 2

2.2 GHS label elements, including precautionary statements

Pictogram(s)
Signal word	Danger
Hazard statement(s)	H300 Fatal if swallowed
Precautionary statement(s)
Prevention	P264 Wash ... thoroughly after handling. P270 Do not eat, drink or smoke when using this product.
Response	P301+P310 IF SWALLOWED: Immediately call a POISON CENTER/doctor/\u2026 P321 Specific treatment (see ... on this label). P330 Rinse mouth.
Storage	P405 Store locked up.
Disposal	P501 Dispose of contents/container to ...

2.3 Other hazards which do not result in classification

none

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6. Synthesis Route

76-66-4Total: 5 Synthesis Route

61-54-1 226 Suppliers

76-66-4 108 Suppliers

Literatures:
European Journal of Organic Chemistry, , # 6 p. 1100 - 1106
Yield: null

630-94-4 38 Suppliers

76-66-4 108 Suppliers

Literatures:
Wanner, Martin J.; Ingemann, Steen; Van Maarseveen, Jan H.; Hiemstra, Henk European Journal of Organic Chemistry, 2013 , # 6 p. 1100 - 1106
Yield: ~97%

1443767-64-3

76-66-4 108 Suppliers

Literatures:
European Journal of Organic Chemistry, , # 6 p. 1100 - 1106
Yield: null

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7. Precursor and Product

precursor:

61-54-1

630-94-4

1443767-64-3

1218815-98-5

1443767-65-4

8. Other Information

8.0 Merck: 14,8197

8.1 Definition: ChEBI: A natural product found in Uncaria macrophylla.

8.2 Mesh Entry Terms: isorhynchophylline

8.3 Uses: Rhynchophylline is a novel erythropoietin-producing hepatocellular A4 (EphA4) inhibitor.

8.4 References: See Rhyncophylline

9. Computational chemical data

Molecular Weight: 384.476g/mol
Molecular Formula: C₂₂H₂₈N₂O₄
Compound Is Canonicalized: True
XLogP3-AA: 2.3
Exact Mass: 384.20490738
Monoisotopic Mass: 384.20490738
Complexity: 663
Rotatable Bond Count: 5
Hydrogen Bond Donor Count: 1
Hydrogen Bond Acceptor Count: 5
Topological Polar Surface Area: 67.9
Heavy Atom Count: 28
Defined Atom Stereocenter Count: 4
Undefined Atom Stereocenter Count: 0
Defined Bond Stereocenter Count: 1
Undefined Bond Stereocenter Count: 0
Isotope Atom Count: 0
Covalently-Bonded Unit Count: 1
CACTVS Substructure Key Fingerprint: AAADceB7OAAAAAAAAAAAAAAAAAAAAWLAAAA8QAAAAAAAAFgBAAAAHgAQAAAADyjhmAYyyIPABACIAiXSWACCCAAhIgAIiAEIZMgIJDrA9ZGEIAhklADI6Iec2eOfgAAAAAACAAAAAAAAAAQAAAAAAAAAAA==

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